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ANTIBACTERIAL BASIC BIAROMATIC DERIVATIVES WITH AMINOALKOXY SUBSTITUTION

20170305927 · 2017-10-26

    Inventors

    Cpc classification

    International classification

    Abstract

    The invention relates to antibacterial compounds of formula I

    ##STR00001##

    wherein R.sup.1a, R.sup.2a, R.sup.2b, R.sup.3a, R.sup.3b, R.sup.4, R.sup.5, U.sup.l, U.sup.2, U.sup.3, U.sup.4, V.sup.1, V.sup.2, V.sup.3, V.sup.4, X and Q and n are as defined in the specification. It further relates pharmaceutical compositions containing these compounds and the uses of these compounds in the manufacture of medicaments for the treatment of bacterial infections. These compounds are useful antimicrobial agents effective against a variety of human and veterinary pathogens including among others Gram-positive and Gram-negative aerobic and anaerobic bacteria.

    Claims

    1. A compound of formula I ##STR00036## wherein n represents 0, 1, 2 or 3; R.sup.1a represents H or (C.sub.1-C.sub.3)alkyl; R.sup.2a and R.sup.2b each independently from each other represents H or (C.sub.1-C.sub.3)alkyl; Ria and Rab each independently from each other represents H or (C.sub.1-C.sub.3)alkyl; R.sup.4 represents H, (C.sub.1-C.sub.3)alkyl, or (C.sub.2-C.sub.3)alkyl-NR.sup.4aR.sup.4b, wherein R.sup.4a and R.sup.4b are independently from each other H or (C.sub.1-C.sub.3)alkyl; R.sup.5 represents H, (C.sub.1-C.sub.3)alkyl, or (C.sub.2-C.sub.3)alkyl-NR.sup.5aR.sup.5b, wherein R.sup.5a and R.sup.5b are independently from each other H or (C.sub.1-C.sub.3)alkyl; or R.sup.2a and R.sup.2b together with the carbon atom which bears them, form a 3 to 6-membered cycloalkyl ring; or R.sup.4 and R.sup.5 together with the nitrogen atom which bears them, form a 4 to 6-membered heterocycloalkyl ring; or R.sup.4 and R.sup.5 together with the nitrogen atom which bears them, form a 6 to 8-membered bicyclic heterocycloalkyl ring, which bicyclic heterocycloalkyl ring may optionally be substituted by a group NR.sup.6R.sup.7, wherein R.sup.6 and R.sup.7 are independently from each other H or (C.sub.1-C.sub.3)alkyl; or R.sup.4 and R.sup.5 together with the nitrogen atom which bears them and the adjacent CR.sup.2aR.sup.2b or CR.sup.3aR.sup.3b together form an amidine group; or R.sup.1a and R.sup.3a, together with the carbon atoms which bear them and the carbon atom which connects these latter two atoms, form a 4 to 6-membered cycloalkyl ring, whereby R.sup.2a, R.sup.2b and R.sup.3b each represent H, and n represents 1; or R.sup.1a and R.sup.4, together with the carbon and nitrogen atoms which bear them and the carbon atom(s) which connect(s) the latter two atoms, form a 4 to 6-membered heterocycloalkyl ring, whereby R.sup.2a, R.sup.2b, optional R.sup.3a and optional R.sup.3b each represent H, n represents 0 or 1, and said 4 to 6-membered heterocycloalkyl ring optionally comprises contains a substituent selected from OCH.sub.3 and or CH.sub.3; or R.sup.2a and R.sup.4 together with the carbon and nitrogen atoms which bear them and the optional carbon atom(s) which connect the latter two atoms, form a 4 to 6-membered heterocycloalkyl ring, whereby R.sup.1a, optional R.sup.3a and optional R.sup.3b each represent H, R.sup.2b represents H, NH.sub.2 or OH, and n represents 0, 1 or 2; U.sup.1 represents N or CH, U.sup.2 represents N, CH, C—O(C.sub.1-C.sub.3)alkyl, or C—CN, U.sup.3 represents N or CH and U.sup.4 represents N or CH, it being understood that at most three of U.sup.1, U.sup.2, U.sup.3 and U.sup.4 can represent N at the same time; V.sup.1 represents N or CH, V.sup.2 represents N or CH, V.sup.3 represents N or CH and V.sup.4 represents N or CH, it being understood that at most three of V.sup.1, V.sup.2, V.sup.3 and V.sup.4 can represent N at the same time; X represents CH or N; Q represents O or S; or a salt of this compound.

    2. The compound of formula I according to claim 1, which is also a compound of formula I.sub.A ##STR00037## wherein n represents 0, 1, 2 or 3; R.sup.1a represents H or (C.sub.1-C.sub.3)alkyl; R.sup.2a and R.sup.2b each independently from each other represents H or (C.sub.1-C.sub.3)alkyl; R.sup.3a and R.sup.3b each independently from each other represents H or (C.sub.1-C.sub.3)alkyl; R.sup.4 represents H, (C.sub.1-C.sub.3)alkyl, or (C.sub.2-C.sub.3)alkyl-NR.sup.4aR.sup.4b, wherein R.sup.4a and R.sup.4b are independently from each other H or (C.sub.1-C.sub.3)alkyl; R.sup.5 represents H, (C.sub.1-C.sub.3)alkyl, or (C.sub.2-C.sub.3)alkyl-NR.sup.5aR.sup.5b, wherein R.sup.5a and R.sup.5b are independently from each other H or (C.sub.1-C.sub.3)alkyl; or R.sup.2a and R.sup.2b together with the carbon atom which bears them, form a 3 to 6-membered cycloalkyl ring; or R.sup.4 and R.sup.5 together with the nitrogen atom which bears them, form a 4 to 6-membered heterocycloalkyl ring; or R.sup.4 and R.sup.5 together with the nitrogen atom which bears them, form a 6 to 8-membered bicyclic heterocycloalkyl ring, which bicyclic heterocycloalkyl ring may optionally be substituted by a group NR.sup.6R.sup.7, wherein R.sup.6 and R.sup.7 are independently from each other H or (C.sub.1-C.sub.3)alkyl; or R.sup.4 and R.sup.5 together with the nitrogen atom which bears them and the adjacent CR.sup.2aR.sup.2b or CR.sup.3aR.sup.3b together form an amidine group; or R.sup.1a and R.sup.3a, together with the carbon atoms which bear them and the carbon atom which connects these latter two atoms, form a 4 to 6-membered cycloalkyl ring, whereby R.sup.2a, R.sup.2b and R.sup.3b each represent H, and n represents 1; U.sup.1 represents N or CH, U.sup.2 represents N, CH, C—O(C.sub.1-C.sub.3)alkyl, or C—CN, U.sup.3 represents N or CH and U.sup.4 represents N or CH, it being understood that at most three of U.sup.1, U.sup.2, U.sup.3 and U.sup.4 can represent N at the same time; V.sup.1 represents N or CH, V.sup.2 represents N or CH, V.sup.3 represents N or CH and V.sup.4 represents N or CH, it being understood that at most three of V.sup.1, V.sup.2, V.sup.3 and V.sup.4 can represent N at the same time; X represents CH or N; Q represents O or S; or a salt of this compound.

    3. The compound of formula I according to claim 1, which is also a compound of formula I.sub.B ##STR00038## wherein R.sup.1a and R.sup.4, together with the carbon and nitrogen atoms which bear them and the carbon atom(s) which connect(s) the latter two atoms, form a 4 to 6-membered heterocycloalkyl ring, whereby R.sup.2a, R.sup.2b, optional R.sup.3a and optional R.sup.3b each represent H, n represents 0 or 1, and said 4 to 6-membered heterocycloalkyl ring optionally comprises a substituent selected from OCH.sub.3 or CH.sub.3; or R.sup.2a and R.sup.4 together with the carbon and nitrogen atoms which bear them and the optional carbon atom(s) which connect(s) the latter two atoms, form a 4 to 6-membered heterocycloalkyl ring, whereby R.sup.1a, optional R.sup.3a and optional R.sup.3b each represent H, R.sup.2b represents H, NH.sub.2 or OH, and n represents 0, 1 or 2; R.sup.5 represents H, (C.sub.1-C.sub.3)alkyl, or (C.sub.2-C.sub.3)alkyl-NR.sup.5aR.sup.5b, wherein R.sup.5a and R.sup.5b are independently from each other H or (C.sub.1-C.sub.3)alkyl; U.sup.1 represents N or CH, U.sup.2 represents N, CH, C—O(C.sub.1-C.sub.3)alkyl, or C—CN, U.sup.3 represents N or CH and U.sup.4 represents N or CH, it being understood that at most three of U.sup.1, U.sup.2, U.sup.3 and U.sup.4 can represent N at the same time; V.sup.1 represents N or CH, V.sup.2 represents N or CH, V.sup.3 represents N or CH and V.sup.4 represents N or CH, it being understood that at most three of V.sup.1, V.sup.2, V.sup.3 and V.sup.4 can represent N at the same time; X represents CH or N; Q represents O or S; or a salt of this compound.

    4. The compound according to claim 1, wherein R.sup.1a represents H or CH.sub.3; R.sup.2a and R.sup.2b each independently from each other represents H or CH.sub.3; R.sup.3a and R.sup.3b each independently from each other represents H or CH.sub.3; R.sup.4 represents H, CH.sub.3, or CH.sub.2CH.sub.2NH.sub.2; R.sup.5 represents H, CH.sub.3, or CH.sub.2CH.sub.2NH.sub.2; and n represents 0, 1, 2 or 3; or a salt of this compound.

    5. The compound according to claim 1, wherein R.sup.1a, R.sup.2a, R.sup.2b, R.sup.3a and R.sup.3b each represent H; R.sup.4 and R.sup.5 together with the nitrogen atom which bears them, form an azetidinyl, pyrrolidinyl, piperidinyl or morpholinyl ring; and n represents 0, 1, 2 or 3; or a salt of this compound.

    6. The compound according to claim 1, wherein R.sup.1a represents H or CH.sub.3; R.sup.2a and R.sup.2b, each independently from each other represents H or CH.sub.3; R.sup.3a and R.sup.3b each independently from each other represents H or CH.sub.3; R.sup.4 and R.sup.5 together with the nitrogen atom which bears them,. form a 6-amino-3-azabicyclo[3.1.0]hexan-3-yl group; or R.sup.4 and R.sup.5 together with the nitrogen atom which bears them and the adjacent CR.sup.2aR.sup.2b or CR.sup.3aR.sup.3b together form an amidine group; or R.sup.1a and R.sup.3a, together with the carbon atoms which bear them and the carbon atom which connects these latter two atoms, form a cyclobutyl, cyclopentyl or cyclohexyl ring; n represents 0, 1, 2 or 3; or a salt of this compound.

    7. The compound according to claim 1, wherein R.sup.1a and R.sup.4, together with the carbon and nitrogen atoms which bear them and the carbon atom(s) which connect(s) the latter two atoms, form an azetinyl, pyrrolidinyl or piperidinyl ring, and said azetinyl, pyrrolidinyl or piperidinyl ring optionally contains comprises a substituent selected from OCH.sub.3 and or CH.sub.3; R.sup.2a and R.sup.2b represent H; R.sup.3a and R.sup.3b represent H; R.sup.5 represents H or CH.sub.3; and n represents 0 or 1; or a salt of this compound.

    8. The compound according to claim 1, wherein R.sup.1a represents H; R.sup.2a and R.sup.4 together with the carbon and nitrogen atoms which bear them and the optional carbon atom(s) which connect(s) the latter two atoms, form a azetidinyl, pyrrolidinyl or morpholinyl ring; R.sup.2b represents H, NH.sub.2 or OH; R.sup.3a and R.sup.3b represent H; R.sup.5 represents H or CH.sub.3; and n represents 0, 1 or 2; or a salt of this compound.

    9. The compound oaccording to claim 1 , wherein U.sup.1 represents N or CH; U.sup.2 represents N, CH, C—OCH.sub.3 or C—CN; U.sup.3 represents N or CH; and U.sup.4 represents N or CH; it being understood that at most three of U.sup.1, U.sup.2, U.sup.3 and U.sup.4 can represent N at the same time; or a salt of this compound.

    10. The compound according to claim 1, wherein U.sup.1, U.sup.2, U.sup.3, U.sup.4, V.sup.1, V.sup.2, V.sup.3 and V.sup.4 each represent CH; or U.sup.2 represents N; U.sup.1, U.sup.3, U.sup.4, V.sup.1, V.sup.2, V.sup.3 and V.sup.4 each represent CH; or U.sup.2 represents C—OCH.sub.3; U.sup.1, U.sup.3, U.sup.4, V.sup.1, V.sup.2, V.sup.3 and V.sup.4 each represent CH; or U.sup.3 represents N; U.sup.1, U.sup.2, U.sup.4, V.sup.1, V.sup.2, V.sup.3 and V.sup.4 each represent CH; or U.sup.4 represents N; U.sup.1, U.sup.2, U.sup.3, V.sup.1, V.sup.2, V.sup.3 and V.sup.4 each represent CH; or U.sup.2 and U.sup.4 represent N; U.sup.1, U.sup.3, V.sup.1, V.sup.2, V.sup.3 and V.sup.4 each represent CH; or U.sup.4 and V.sup.3 represent N; U.sup.1, U.sup.2, U.sup.3, V.sup.1, V.sup.2 and V.sup.4 each represent CH; or a salt of this compound.

    11. The compound according to claim 1, wherein said compound is: 6-[(S)-5-(2-{[3′-(2-amino-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[3′-(2-dimethylamino-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[3′-(3-amino-propoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[3′-(2-methylamino-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[3′-(4-amino-butoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[3′-(2-amino-1-methyl-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[3′-((1R,3R)-3-amino-cyclopentyloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-(2-amino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-2-oxo-5-(2-{3-[6-(2-pyrrolidin-1-yl-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[5-(2-dimethylamino-ethoxy)-pyridazin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[5-(2-amino-ethoxy)-pyridin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-2-oxo-5-(2-{3-[6-(2-piperidin-1-yl-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-2-oxo-5-(2-{[3′-(2-piperid in-1-yl-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[3′-(1-amino-cyclopropylmethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-(2-amino-ethoxy)-pyrazin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[6-(2-amino-ethoxy)-[2,4′]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-((R)-2-amino-propoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-((S)-2-amino-propoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[2-(2-amino-ethoxy)-pyridin-4-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one, 6-[(S)-5-(2-{[3′-((S)-1-azetidin-2-ylmethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-2-oxo-5-(2-{[3′-((S)-1-pyrrolidin-2-ylmethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-2-oxo-5-(2-{[3′-(pyrrolidin-3-yloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one, 6-[(S)-5-(2-{[3′-((S)-1-methyl-azetidin-2-ylmethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[3′-(azetidin-3-yloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-(azetidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-(azetidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-((S)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-(1-morpholin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-(1-morpholin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-2-oxo-5-(2-{3-[6-(piperidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{[3′-(2-amino-ethoxy)-5′-methoxy-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(R)-5-(2-{3-[6-(2-amino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one; 6-[(S)-5-(2-{3-[6-(5-amino-pentyloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; 6-[(S)-5-(2-{3-[6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one, and or (3S*,4S1-6-[(S)-5-(2-{3-[6-(4-methoxy-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one; or a salt of this compound.

    12. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, formulated as a medicament.

    13. A pharmaceutical composition comprising, as active principle, a the compound according to claim 1, or a pharmaceutically acceptable salt thereof, and at least one therapeutically inert excipient.

    14. A method of preventing or treating a bacterial infection comprising administering to a subject an amount of the compound according to claim 1 or a pharmaceutically acceptable salt thereof.

    15. The compound or pharmaceutically acceptable salt according to claim 14, wherein the bacterial infection is mediated by Staphylococcus aureus bacteria or Acinetobacter baumannii bacteria.

    Description

    EXAMPLES

    [0624] All temperatures are stated in ° C. Unless otherwise indicated, the reactions take place at rt.

    [0625] Analytical TLC characterizations were performed with 0.2 mm plates: Merck, Silica gel 60 F254. Elution is performed with EA, Hept, DCM, MeOH or mixtures thereof. Detection was done with UV or with a solution of KMnO.sub.4 (3 g), K.sub.2CO.sub.3 (20 g), 5% NaOH (3 mL) and H.sub.2O (300 mL) with subsequent heating.

    [0626] CCs were performed using Brunschwig 60A silica gel (0.032-0.63 mm) or using an ISCO CombiFlash system and prepacked SiO.sub.2 cartridges, elution being carried out with either Hept-EA or DCM-MeOH mixtures with an appropriate gradient.

    [0627] The compounds were characterized by .sup.1H-NMR (300 MHz, Varian Oxford; 400 MHz, Bruker Avance 400 or 500 MHz, Bruker Avance 500 Cryoprobe).Chemical shifts 6 are given in ppm relative to the solvent used; multiplicities: s=singlet, d=doublet, t=triplet, q=quadruplet, p=pentuplet, hex=hexet, hep=heptet, m=multiplet, br.=broad; coupling constants J are given in Hz. Alternatively compounds were characterized by LC-MS (Sciex API 2000 with Agilent 1100 Binary Pump with DAD and ELSD or an Agilent quadrupole MS 6140 with Agilent 1200 Binary Pump, DAD and ELSD); by TLC (TLC plates from Merck, Silica gel 60 F.sub.254); or by melting point.

    [0628] The analytical LC-MS data have been obtained using the following respective conditions:

    [0629] MS1 data: [0630] Column: Zorbax SB-Aq, 3.5 μm, 4.6×50 mm; [0631] Injection volume: 1 μL; [0632] Column oven temperature: 40° C.; [0633] Pump: Agilent G4220A; [0634] Makeup pump: Dionex HPG-3200SD; [0635] DAD: Agilent G4212A; [0636] MS: Thermo MSQ Plus; [0637] ELSD: Sedere Sedex 90; [0638] Detection: UV 210 nm, ELSD and MS; [0639] MS ionization mode: ESI+; [0640] Eluents: A: H.sub.2O +0.04% TFA; and B: MeCN; [0641] Flow rate: 4.5 mL/min; [0642] Gradient: 5% B (0.00 min 0.08 min), 5% B to 95% B (0.08 min-1.07 min), 95% B (1.07 min-1.57 min).

    [0643] MS2 data: [0644] Column: Waters X-Bridge C18, 2.5 μm, 4.6×30 mm; [0645] Injection volume: 1 μL; [0646] Column oven temperature: 40° C.; [0647] Pump: Dionex HPG-320016; [0648] Makeup pump: Dionex ISO-31005D; [0649] DAD: Dionex DAD-3000016; [0650] MS: Thermo MSQ Plus; [0651] ELSD: Sedere Sedex 85; [0652] Detection: UV 210 nm, ELSD and MS; [0653] MS ionization mode: ESI+; [0654] Eluents: A: H.sub.2O+0.04% TFA; and B: MeCN; [0655] Eluent flow rate: 4.5 mL/min; [0656] Gradient: 5% B (0.00 min 0.01 min), 5% B to 95% B (0.01 min 1.0 min), 95% B (1.0 min-1.45 min).

    [0657] MS3 data: [0658] Column: Zorbax SB-Aq, 3.5 μm, 4.6×50 mm; [0659] Otherwise same parameters as for obtaining MS2 data.

    [0660] MS4 data: [0661] Column: Phenomex Gemini, C18 110A, 3 μm, 2×50 mm; [0662] Injection volume: 3 μL; [0663] Eluents: A: H.sub.2O (+0.1% HCOOH); and B: MeCN (+0.1% HCOOH); [0664] Eluent flow rate: 0.3 mL/min; [0665] Gradient: from 40% to 95% B in (0.00 min 9.00 min).

    [0666] The number of decimals given for the corresponding [M+H.sup.+] peak(s) of each tested compound depends upon the accuracy of the LC-MS device actually used.

    [0667] The prep-HPLC purifications were performed on a Gilson HPLC system, equipped with a Gilson LH215 autosampler, Gilson 333/334 pumps, Thermo Finnigan MSQ Plus detector system, and a Dionex UVD340U (or Dionex DAD-3000) UV detector, using the following respective conditions:

    [0668] Method 1: [0669] Column: Waters Atlantis T3 OBD, 10 μm, 30×75 mm; [0670] Flow rate: 75 mL/min; [0671] Eluents: A: H.sub.2O +0.5% HCOOH; B: MeCN; [0672] Gradient: 90% A to 5% A (0.0 min 4.0 min), 5% A (4.0 min 6.0 min).

    [0673] Method 2: [0674] Column: Waters)(Bridge C18, 10 μm, 30×75 mm; [0675] Flow rate: 75 mL/min; [0676] Eluents: A: H.sub.2O +0.5% NH.sub.4OH; B: MeCN; [0677] Gradient: 90% A to 5% A (0.0 min 4.0 min), 5% A (4.0 min 6.0 min).

    [0678] Method 3: [0679] Column: Waters)(Bridge C18, 10 μm, 30×75 mm; [0680] Flow rate: 75 mL/min; [0681] Eluents: A: H.sub.2O +0.5% NH.sub.4OH; B: MeCN; [0682] Gradient: 95% A to 50% A (0.0-3.0 min), 50% A to 5% A (3.0-4.0 min), 5% A (4.0-6.0 min).

    [0683] Method 4: [0684] Column: Waters)(Bridge C18, 10 μm, 30×75 mm; [0685] Flow rate: 75 mL/min; [0686] Eluents: A: H.sub.2O+0.5% HCOOH; B: MeCN; [0687] Gradient: 90% A to 5% A (0.0 min 4.0 min), 5% A (4.0 min 6.0 min).

    [0688] The following other purification methods were furthermore used: [0689] Filtration over Si-carbonate: silica bound equivalent of tetramethyl ammonium carbonate, SiliaPrep SPE cartridges Carbonate, 200 mg, 3 mL (Silicycle SPE-R6603 0B-03 G). [0690] Filtration over Alumina cartridges: polar sorbent basic character, SiliaPrep SPE Cartridges Alumina Neutral, 1 g, 6 mL (Silicycle SPE-AUT-0054-065).

    [0691] Preparations:

    [0692] General Building Blocks

    Preparation BB1: 3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-ol

    [0693] 3-bromophenol (400 mg; commercial), 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (638 mg; commercial), Pd(PPh.sub.3).sub.4 (107 mg; commercial) and K.sub.2CO.sub.3 (959 mg) were suspended in water (5 mL) and dioxane (15 mL). Nitrogen was bubbled through the reaction mixture and it was further stirred at 100° C. for 2 h. The reaction mixture was cooled to rt and partitioned between water and EA. The aq. layer was extracted with EA and the combined org. layers were washed with brine and dried over MgSO.sub.4, affording after CC purification (Combiflash; Hept/EA 1:0 to 0:1) 400 mg (71% yield) of a yellow oil. MS3 (ESI, m/z): 243.04 [M+H.sup.+]; t.sub.R=0.77 min.

    Preparation BB2: 6-(3-(1,3-dioxolan-2-yl)phenyl)pyridin-2-ol

    [0694] Starting from 6-chloro-2-hydroxypyridine (383 mg; commercial), 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (801 mg; commercial), Pd(PPh.sub.3).sub.4 (134 mg; commercial) and K.sub.2CO.sub.3 (1.20 g) and proceeding in analogy to Preparation BB1, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a brown oil (303 mg; 43% yield).

    [0695] MS2 (ESI, m/z): 244.07 [M+H.sup.+]; t.sub.R=0.62 min.

    Preparation BB3: 3-(3-(1,3-dioxolan-2-yl)phenyl)-5-chloropyridazine

    [0696] A mixture of 3,5-dichloropyridazine (1.50 g; commercial), 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (2.78 g; commercial), palladium acetate (113 mg; commercial), 1,1-bis(diphenylphosphino)ferrocene (288 mg; commercial) and Cs.sub.2CO.sub.3 (8.20 g) in dioxane (40 mL) and water (10 mL) was degased with nitrogen and stirred at 70° C. for 1 day. The mixture was allowed to reach rt, diluted with EA, filtered and partially concentrated under reduced pressure. The residue was diluted with water and the org. layer was separated, washed with brine, dried over MgSO.sub.4, filtered, evaporated and purified CC (Combiflash; Hept to Hept/EA 1:1), affording an orange solid (2.05 g; 77.5% yield). MS3 (ESI, m/z): 263.00 [M+H.sup.+]; t.sub.R=0.75 min.

    Preparation BB4: 5-(3-(1,3-dioxolan-2-yl)phenyl)pyridin-3-ol

    [0697] Starting from 5-bromo-5-hydroxypyridine (541 mg; commercial), 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (859 mg; commercial), Pd(PPh.sub.3).sub.4 (180 mg; commercial) and Na.sub.2CO.sub.3 (1M; 3.11 mL) and proceeding in analogy to Preparation BB1, but using EtOH and water as solvent, the title compound (540 mg; 71% yield) was obtained after purification by CC (Combiflash; Hept/EA 1:0 to 0:1) as a yellow oil. MS3 (ESI, m/z): 244.07 [M+H.sup.+]; t.sub.R=0.52 min.

    Preparation BBS: 6-(3-[1,3]dioxolan-2-yl-phenyl)-pyrazin-2-ol

    [0698] Starting from 6-bromopyrazin-2-ol (450 mg) and 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (710 mg) and proceeding in analogy to Preparation BB1, but using EtOH, toluene and water as solvent, the title compound was obtained as a yellow solid (466 mg; 74% yield).

    [0699] MS3 (ESI, m/z): 245.04 [M+H.sup.+]; t.sub.R=0.59 min.

    Preparation BBδ: 2′-[1,3]dioxolan-2-yl-[2,4]bipyridinyl-6-ol

    [0700] A mixture of 4-bromo-2-(1,3-dioxolan-2-yl)-pyridine (1500 mg), bis(pinacolato)diboron (1858 mg), potassium acetate (1600 mg) and dichloro[1,1′-bi s(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (626 mg) in dioxane (25 mL) was degassed for 5 min with N.sub.2 and sealed in a Schlenk flask. The resulting dark brown suspension was stirred at 90° C. for 1.5 h. The mixture was cooled down to rt, diluted with EA, filtered through a glass fiber filter and concentrated under reduced pressure and used directly in the next step. The resulting crude 2-(1,3-dioxolan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1028 mg) was mixed with 6-chloro-2-hydroxypyridine (450 mg), palladium(II) acetate (38.2 mg), 1,1′-bis(diphenylphosphino)ferrocene (94.4 mg) and cesium carbonate (2773 mg) in dioxane (10 mL) and water (2.5 mL) and degassed for 5 min with N.sub.2 and sealed in a Schlenk flask. The resulting dark brown suspension was stirred at 70° C. for 4 h.The mixture was cooled down to rt, diluted with EA, filtered through a glass fiber filter and concentrated under reduced pressure. The residue was purified by CC (Combiflash; Hept/EA 7:3 to EA/MeOH 9:1), affording a brown solid (431 mg; 52% yield). MS3 (ESI, m/z): 245.06 [M+H.sup.+]; t.sub.R=0.49 min.

    Preparation BB7: 4-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-ol

    [0701] Starting from 4-bromo-2-hydroxypyridine (400 mg; commercial) and 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (635 mg) and proceeding in analogy to Preparation BB 1, the title compound was obtained as a brown oil (460 mg; 82% yield).

    [0702] MS3 (ESI, m/z): 244.09 [M+H.sup.+]; t.sub.R=0.62 min.

    Preparation BBB: 3′-[1,3]dioxolan-2-yl-5-methoxy-biphenyl-3-ol

    [0703] Starting from 4-bromo-2-hydroxypyridine (467 mg; commercial), 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (635 mg; commercial), Pd(PPh.sub.3).sub.4 (106 mg; commercial) and K.sub.2CO.sub.3 (953 mg) and proceeding in analogy to Preparation BB 1, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 19:1), as a colourless oil (473 mg; 76% yield).

    [0704] MS2 (ESI, m/z): 272.99 [M+H.sup.+]; t.sub.R=0.77 min.

    Preparation BB9: 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carbaldehyde

    [0705] A mixture of 4-bromopyridine-2-carboxaldehyde (1.86 g; commercial), bis(pinacolato)-diboron (2.82 g), potassium acetate (2.48 g) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (408 mg) in dioxane (20 mL) was degassed for 5 min with N.sub.2 and stirred at 90° C. for 2 h. The mixture was cooled down to rt, diluted with EA, filtered through a pad of Celite, concentrated under reduced pressure and used directly in the next step.

    [0706] .sup.1H NMR (CDCl.sub.3) δ: 10.13 (s, 1H); 8.82 (d, J=4.6 Hz, 1H); 8.34 (s, 1H); 7.87 (d, J=4.4 Hz, 1H); 1.33 (m, 12H).

    Preparation BB10: [2-(6-bromo-pyridin-2-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [0707] DIAD (2.14 mL) was added dropwise to a 0° C. solution of 6-bromopyridin-2-ol (2.5 g; commercial), (Boc-amino)ethanolamine (2.32 mL; commercial) and P(Ph).sub.3 (3.94 g) in THF (45 mL). The mixture was stirred at rt for 3 h. The volatiles were removed under reduced pressure. The resulting residue was partitioned between EA and water, the aq. layer was extracted with EA and the combined org. layers were washed with brine and dried over MgSO.sub.4. The title compound was obtained after purification by CC (Combiflash; Hept-EA, 1-0 to 0-1) as an off-white oil (3.6 g; 83% yield). MS3 (ESI, m/z): 316.88 [M+H.sup.+]; t.sub.R=0.88 min.

    Preparation BB11: (3-(1,3-dioxolan-2-yl)phenyl)trihydroxyborate

    BB11.i. 2-bromo-6-(1,3-dioxalan-2-yl)pyridine

    [0708] A mixture of 2-bromo-6-formylpyridine (7.35 g), ethylene glycol (3.57 mL) and a catalytic amount of p-toluene sulfonic acid (0.49 g) in 175 mL benzene was heated at reflux using a Dean Stark trap for 1 day. Dilution with sat. aq. NaHCO.sub.3 (40 mL) and extraction with DCM (2×100 mL), dried over Na.sub.2SO.sub.4 and concentrated under reduced pressure afforded the title compound, after purification by CC (DCM-DCM/EtOH 95:5), as a yellow oil (7.62 g; 84% yield).

    [0709] .sup.1H NMR (CDCl.sub.3) δ: 7.74 (t, J=7.8 Hz, 1H); 7.57 (t, J=7.8 Hz, 2H); 5.72 (s, 1H); 4.13 (m, 2H); 4.04 (m, 2H).

    BB11.ii. Lithium-(3-(1,3-dioxolan-2-yl)phenyl)triisopropoxyborate

    [0710] An oven-dried round-bottomed flask was charged with toluene (83 mL) and THF (20 mL) and placed under argon atmosphere. The flask was charged with intermediate BB11.i (5.0 g) and cooled to −78° C. BuLi (14.25 mL) was added dropwise over 45 min, and the mixture was stirred for 45 min at −78° C. Triisopropylborate (4.27 g) was added dropwise via a syring pump over 70 min, and the mixture was stirred for an additional 2 h at −78° C. The resulting solution was concentrated under reduced pressure. To the dark residue was added Et.sub.2O (60 mL) and the mixture was left in an ultrasonic bath for 10 min. The brown precipitate was filtered, washed with Et.sub.2O (3×15 mL) and dried under high vacuum for 3 h to yield the title compound as a brown solid (4.3 g; 61% yield).

    [0711] .sup.1H NMR (CDCl.sub.3) δ: 7.64 (t, J=7.5 Hz, 1H); 7.52 (dd, J=1.2, 7.5 Hz, 1H); 7.28 (dd, J=1.2, 7.5 Hz, 1H); 5.77 (s, 1H); 4.13-4.02 (m, 4H).

    BB11.iii. Lithium-(3-(1,3-dioxolan-2-yl)phenyl)trihydroxyborate

    [0712] A mixture of intermediate BB11.ii (0.23 g), in 9 mL acetone and 1 mL water was stired at rt for 24 h. The yellow precipitate was filtered, washed with 10 mL of mixture acetone/water (9:1) and dried at rt, to give the title compound as a yellow precipitate (0.11 g; 75% yield).

    [0713] .sup.1H NMR (CDCl.sub.3) δ: 7.64 (t, J=7.5 Hz, 1H); 7.52 (dd, J=1.2, 7.5 Hz, 1H); 7.28 (dd, J=1.2, 7.5 Hz, 1H); 5.77 (s, 1H); 4.13-4.02 (m, 4H); 3.92 (m, 3H); 1.15 (m, 18H).

    [0714] Specific Building Blocks

    Preparation A1: [2-(3′-formyl-biphenyl-3-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [0715] N-(2-(3-bromophenoxy)ethyl)carbamic acid tert-butyl ester (197 mg; prepared according to WO 2009/005794) and 3-formylphenylboronic acid (112 mg; commercial) were added to a mixture of aq. NaHCO.sub.3 (10%; 1.3 mL) and DME (2.9 mL). N.sub.2 was bubbled through the reaction mixture, Pd(PPh.sub.3).sub.4 (29 mg) was added and the reaction mixture was further stirred at 80° C. overnight. The reaction mixture was cooled to rt and partitioned between water and EA. The aq. layer was extracted with EA and the combined org. layers were washed with brine and dried over MgSO.sub.4, affording a brown oil (230 mg; 100% yield) which was further used without any purification.

    [0716] MS1 (ESI, m/z): 342.16 [M+H.sup.+]; t.sub.R=0.94 min.

    Preparation A2: 3′-(2-(dimethylamino)ethoxy)-[1,1′-biphenyl]-3-carbaldehyde

    [0717] DIAD (82 mg) was added dropwise to a solution of the compound of Preparation BB1 (100 mg), dimethylethanolamine (0.04 mL) and PPh.sub.3 (106 mg) in THF (1.2 mL) cooled to 0° C. The solution was allowed to reach rt and was further stirred overnight. The reaction mixture was evaporated under reduced pressure and the residue was partitioned between 1M HCl and EA. The aq. layer was washed with EA and neutralized with sat. NaHCO.sub.3. The aq. layer was extracted with EA and dried over MgSO.sub.4, affording a yellowish oil (44 mg; 44% yield) which was further used without any purification. MS3 (ESI, m/z): 270.09 [M+H.sup.+]; t.sub.R=0.60 min.

    Preparation A3: tert-butyl (2-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)ethyl)(methyl) carbamate

    A3.i. Tert-butyl (2-((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)ethyl)(methyl) carbamate

    [0718] A mixture of the compound of Preparation BB 1 (100 mg), (2-hydroxyethyl)(methyl)carbamic acid tert-butyl ester (commercial; 80 mg) and PPh.sub.3 (162 mg) in THF (4 mL) was treated dropwise with DEAD (40% in toluene; 0.18 mL) and the reaction mixture was further stirred at rt for 1 d. The solution was concentrated under reduced pressure and portioned between EA and water. The aq. layer was extracted with EA and the combined org. layers were washed with brine, dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The residue was purified by CC (Combiflash; Hept/EA 1:0 to 0:1), affording a colourless oil (31 mg; 19% yield).

    [0719] MS2 (ESI, m/z): 300.00 [M+H.sup.+]; t.sub.R=0.96 min.

    A3.ii. Tert-butyl (2-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)ethyl)(methyl)carbamate

    [0720] A solution of intermediate A3.i (25 mg) and PTSA (0.30 mg) in acetone (0.25 mL) was stirred at rt for 4 days. The solution was filtered and evaporated under reduced pressure, affording a brown oil (quant.) which was used without further purification.

    [0721] MS2 (ESI, m/z): 355.91 [M+H.sup.+]; t.sub.R=0.95 min.

    Preparation A4: tert-butyl (4-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)butyl)carbamate

    A4.i. Tert-butyl (4-((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)butyl)carbamate

    [0722] Starting from the compound of Preparation BB1 (300 mg) and 4-(Boc-amino)-1-butanol (commercial; 231 mg), and proceeding in analogy to Preparation A3, step A3.i, the title compound was obtained after purification by CC (Combiflash; Hept/EA 1:0 to 0:1) as an yellow oil (489 mg; contaminated by residual PPh.sub.3O).

    [0723] MS2 (ESI, m/z): 414.03 [M+H.sup.+]; t.sub.R=0.94 min.

    A4.ii. Tert-butyl (4-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)butyl)carbamate

    [0724] Starting from intermediate A4.i (470 mg) and proceeding in analogy to Preparation A3, step A3.ii, the title compound was obtained as a yellow oil (484 mg; 100% yield) and used directly in the subsequent step.

    [0725] MS2 (ESI, m/z): 369.86 [M+H.sup.+]; t.sub.R=0.94 min.

    Preparation A5: tert-butyl (RS)-(2-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)propyl) carbamate

    A5. i. Tert-butyl (RS)-(2-((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)propyl)carbamate

    [0726] Starting from the compound of Preparation BB1 (300 mg) and tert-butyl N-(2-hydroxypropyl)carbamate (commercial; 214 mg), and proceeding in analogy to Preparation A3, step A3.i, the title compound was obtained after purification by CC (Combiflash; Hept/EA 1:0 to 1:0) as a yellow oil (216 mg; 49% yield).

    [0727] MS2 (ESI, m/z): 400.00 [M+H.sup.+]; t.sub.R=0.92 min.

    A5. ii. Tert-butyl (RS)-(2-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)propyl) carbamate

    [0728] Starting from intermediate A5.i (200 mg) and proceeding in analogy to Preparation A3, step A3.ii, the title compound was obtained as a yellow oil (197 mg; 100% yield) and used directly in the subsequent step.

    [0729] MS2 (ESI, m/z): 355.99 [M+H.sup.+]; t.sub.R=0.91 min.

    Preparation A6: tert-butyl ((1R,3R)-3-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy) cyclopentyl)carbamate

    [0730] A6.i. Tert-butyl ((1R,3R)-3-((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy) cyclopentyl)carbamate

    [0731] The title compound can be prepared starting from the compound of Preparation BB1 and tert-butyl N-[(1R,3S)-3-hydroxycyclopentyl]carbamate (commercial), and proceeding in analogy to Preparation A3, step A3.i.

    A6. ii. Tert-butyl ((1R,3R)-3-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy) cyclopentyl)carbamate

    [0732] The title compound can be prepared starting from intermediate A6.i and proceeding in analogy to Preparation A3, step A3.ii.

    Preparation A7: tert-butyl (2-((6-(3-formylphenyl)pyridin-2-yl)oxy)ethyl)carbamate

    A7. i. Tert-butyl (2-((6-(3-(1,3-dioxolan-2-yl)phenyl)pyridin-2-yl)oxy)ethyl)carbamate

    [0733] Starting from the compound of Preparation BB2 (280 mg) and (Boc-amino)ethanolamine (commercial; 204 mg), and proceeding in analogy to Preparation A3, step A3.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 0:1 to 1:0), as a colourless oil (340 mg; 76% yield).

    [0734] MS3 (ESI, m/z): 386.98 [M+H.sup.+]; t.sub.R=0.92 min.

    A 7. ii. Tert-butyl (2-((6-(3-formylphenyl)pyridin-2-yl)oxy)ethyl)carbamate

    [0735] A solution of intermediate A7.i (320 mg) in THF (4.6 mL) was heated at 50° C. for 5 min in presence of 1M HCl (1.55 mL). The reaction mixture was allowed to cool to rt, treated with excess sat. NaHCO.sub.3 solution and extracted 5 times with DCM/MeOH. The combined org. layers were washed with brine, dried over MgSO.sub.4, filtered and concentrated under reduced pressure, affording a yellow oil (300 mg; 100% yield) which was used directly in the subsequent step.

    [0736] MS3 (ESI, m/z): 342.98 [M+H.sup.+]; t.sub.R=0.93 min.

    Preparation A8: 3-(6-(2-(pyrrolidin-1-yl)ethoxy)pyridin-2-yl)benzaldehyde

    A8. i. 2-(3-(1,3-dioxolan-2-yl)phenyl)-6-(2-(pyrrolidin-1-yl)ethoxy)pyridine

    [0737] Starting from 2-chloro-6-[2-(pyrrolidin-1-yl)ethoxy]pyridine (300 mg; commercial), 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (365 mg; commercial), Pd(PPh.sub.3).sub.4 (76 mg; commercial) and Na.sub.2CO.sub.3 (1M, 1.34 mL) and proceeding in analogy to Preparation BB1, but using EtOH and toluene as solvent, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a brown oil (300 mg; 67% yield).

    [0738] .sup.1H NMR (CDCl.sub.3) δ: 8.13 (m, 1H); 8.07 (m, 1H); 7.62-7.66 (m, 1H); 7.48-7.55 (m, 2H); 7.37-7.39 (m, 1H); 6.75 (dd, J=0.5, 8.2 Hz, 1H); 5.93 (s, 1H); 4.60-4.64 (m, 2H); 4.07-4.22 (m, 4H); 2.94-3.01 (m, 2H); 2.63-2.76 (m, 4H); 1.82-1.89 (m, 4H).

    [0739] MS3 (ESI, m/z): 341.01 [M+H.sup.+]; t.sub.R=0.65 min.

    A8.ii. 3-(6-(2-(pyrrolidin-1-yl)ethoxy)pyridin-2-yl)benzaldehyde

    [0740] Starting from intermediate A8.i (280 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless oil (237 mg; 97% yield) and used directly in the subsequent step.

    [0741] .sup.1H NMR (CDCl.sub.3) δ: 10.13 (s, 1H); 8.54 (t, J=1.7 Hz, 1H); 8.35 (ddd, J=1.4, 1.8, 7.8 Hz, 1H); 7.93 (m, 1H); 7.63-7.72 (m, 2H); 7.42-7.44 (m, 1H); 6.80-6.82 (m, 1H); 4.62-4.67 (m, 2H); 2.96-3.03 (m, 2H); 2.63-2.76 (m, 4H); 1.82-1.91 (m, 4H).

    [0742] MS3 (ESI, m/z): 297.02 [M+H.sup.+]; t.sub.R=0.63 min.

    Preparation A9: 3-(5-(2-(dimethylamino)ethoxy)pyridazin-3-yl)benzaldehyde

    A9. i. 2-((6-(3-(1,3-dioxolan-2-yl)phenyl)pyridazin-4-yl)oxy)-N,N-dimethylethan-1-amine

    [0743] Potassium tert-butoxide (61 mg) was added to a solution of dimethylaminoethanol (33 mg) in THF (1.2 mL). The reaction mixture was stirred for 30 min at rt then treated with compound of Preparation BB3 (100 mg) and further stirred at rt for 30 min. The reaction mixture was diluted with EA, washed with water and brine, dried over MgSO.sub.4, filtered, evaporated and purified by CC (Combiflash; DCM to DCM/MeOH 9:1), affording a yellow oil (101 mg; 88% yield).

    [0744] MS3 (ESI, m/z): 316.01 [M+H.sup.+]; t.sub.R=0.47 min.

    A9.ii. 3-(5-(2-(dimethylamino)ethoxy)pyridazin-3-yl)benzaldehyde

    [0745] Starting from intermediate A9.i (70 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as an orange oil (44 mg; 63% yield).

    [0746] .sup.1H NMR (CDCl.sub.3) δ: 10.16 (s, 1H); 8.99 (d, J=2.8 Hz, 1H); 8.54 (t, J=1.6 Hz, 1H); 8.44 (ddd, J=1.3, 1.7, 7.8 Hz, 1H); 8.04 (dt, J=1.3, 7.6 Hz, 1H); 7.74 (t, J=7.7 Hz, 1H); 7.38 (d, J=2.8 Hz, 1H); 4.30 (t, J=5.5 Hz, 2H); 2.85 (t, J=5.5 Hz, 2H); 2.40 (s, 6H).

    [0747] MS3 (ESI, m/z): 272.06 [M+H.sup.+]; t.sub.R=0.46 min.

    Preparation A10: tert-butyl (2-((5-(3-formylphenyl)pyridin-3-yl)oxy)ethyl)carbamate

    A10.i. Tert-butyl (2-((5-(3-(1,3-dioxolan-2-yl)phenyl)pyridin-3-yl)oxy)ethyl)carbamate

    [0748] Starting from the compound of Preparation BB4 (200 mg) and N-Boc-ethanolamine (0.14 mL) and proceeding in analogy to Preparation A2, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:1), as a yellow oil (238 mg; 75% yield).

    [0749] MS3 (ESI, m/z): 386.95 [M+H.sup.+]; t.sub.R=0.72 min.

    A10.ii. Tert-butyl (2-((5-(3-formylphenyl)pyridin-3-yl)oxy)ethyl)carbamate

    [0750] Starting from intermediate A10.i (235 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless solid (211 mg; 100% yield).

    [0751] MS3 (ESI, m/z): 342.96 [M+H.sup.+]; t.sub.R=0.74 min.

    Preparation A11: 3-(6-(2-(piperidin-1-yl)ethoxy)pyridin-2-yl)benzaldehyde

    A11. i. 2-(3-(1,3-dioxolan-2-yl)phenyl)-6-(2-(piperidin-1-yl)ethoxy)pyridine

    [0752] Starting from the compound of Preparation BB2 (100 mg) and 1-(2-hydroxyethyl)piperidine (64 mg) and proceeding in analogy to Preparation A2, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 19:1), as a yellow oil (99 mg; 68% yield).

    [0753] MS1 (ESI, m/z): 355.13 [M+H.sup.+]; t.sub.R=0.67 min.

    A11.ii. 3-(6-(2-(piperidin-1-yl)ethoxy)pyridin-2-yl)benzaldehyde

    [0754] Starting from intermediate A11.i (72 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow oil (72 mg; 91% yield).

    [0755] MS1 (ESI, m/z): 311.12 [M+H.sup.+]; t.sub.R=0.65 min.

    Preparation A12: 3′-(2-(piperidin-1-yl)ethoxy)-[1,1′-biphenyl]-3-carbaldehyde

    A12.i. 1-(2-((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)ethyl)piperidine

    [0756] Starting from 1-[2-(3-bromophenoxy)ethyl]piperidine (150 mg; commercial) and 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (146 mg; commercial), Pd(PPh.sub.3).sub.4 (30 mg; commercial) and Na.sub.2CO.sub.3 (1M; 0.53 mL) and proceeding in analogy to Preparation BB1, but using EtOH, toluene and water as solvent, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 2:1 to 0:1), as a yellow oil (145 mg; 78% yield).

    [0757] MS3 (ESI, m/z): 353.90 [M+H.sup.+]; t.sub.R=0.64 min.

    A12. ii. 3′-(2-(piperidin-1-yl)ethoxy)-[1,1′-biphenyl]-3-carbaldehyde

    [0758] Starting from intermediate A12.i (135 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless solid (109 mg; 92% yield).

    [0759] MS3 (ESI, m/z): 310.03 [M+H.sup.+]; t.sub.R=0.67 min.

    Preparation A13: tert-butyl (1-(((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)methyl) cyclopropyl)carbamate

    [0760] A13. i. Tert-butyl (1-(((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)methyl)cyclopropyl) carbamate

    [0761] Starting from the compound of Preparation BB1 (300 mg) and tert-butyl 1-(hydroxymethyl) cyclopropylcarbamate (commercial; 228 mg), and proceeding in analogy to preparation A3 step A3.i, the title compound was obtained after purification by CC (Combiflash; DCM to DCM/MeOH 4:1) as a yellow oil (131 mg; 29% yield).

    [0762] MS2 (ESI, m/z): 412.00 [M+H.sup.+]; t.sub.R=0.92 min.

    A 13.ii. Tert-butyl (1-(((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)methyl)cyclopropyl)carbamate

    [0763] Starting from intermediate A13.i (120 mg) and proceeding in analogy to Preparation A3, step A3.ii, the title compound was obtained as an yellow oil (123 mg; quant.) which was used directly in the subsequent step.

    [0764] MS2 (ESI, m/z): 367.97 [M+H.sup.+]; t.sub.R=0.91 min.

    Preparation A14: {2-[6-(3-formyl-phenyl)-pyrazin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [0765] A 14.i. {2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyrazin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [0766] Starting from intermediate BB5 (80 mg) and N-Boc-ethanolamine (0.0439 mL) and proceeding in analogy to preparation A3 step A3.i, the title compound was obtained after purification by CC (Combiflash; Hept to Hept/EA 1:1) as a yellow oil (85 mg; 79% yield).

    [0767] MS3 (ESI, m/z): 387.97 [M+H.sup.+]; t.sub.R=0.89 min.

    A14. ii. {2-[6-(3-formyl-phenyl)-pyrazin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [0768] Starting from intermediate A14.i (78 mg) and proceeding in analogy to Preparation A3, step A3.ii, the title compound was obtained as a colourless oil (66 mg; 95% yield) which was used directly in the subsequent step.

    [0769] MS3 (ESI, m/z): 343.95 [M+H.sup.+]; t.sub.R=0.89 min.

    Preparation A15: [2-(2′-formyl-[2,4]bipyridinyl-6-yloxy)-ethyl]-carbamic acid tert-butyl ester

    A15. i. [2-(2′-[1,3]dioxolan-2-yl-[2,4]bipyridinyl-6-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [0770] Starting from intermediate BB6 (100 mg) and N-Boc-ethanolamine (0.0517 mL) and proceeding in analogy to Preparation A3, step A3.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:2), as a colourless oil (136 mg; contaminated by residual PPh.sub.3O).

    [0771] MS3 (ESI, m/z): 387.98 [M+H.sup.+]; t.sub.R=0.75 min.

    A 15.ii. [2-(2′-formyl-[2,4′]bipyridinyl-6-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [0772] A solution of intermediate A15.i (105 mg) in MeCN/MeOH (1:1; 3 mL) was stirred at 80° C. overnight in presence of carbon tetrabromide (90 mg). The reaction mixture was concentrated under reduced pressure and purified by prep-HPLC (method 2), affording a yellow solid (8.5 mg; 18% yield).

    [0773] MS3 (ESI, m/z): 343.96 [M+H.sup.+]; t.sub.R=0.88 min.

    Preparation A16: {(R)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-1-methyl-ethyl}-carbamic acid tert-butyl ester

    A 16.i. {(R)-2-[6-(3-[1, 3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-1-methyl-ethyl}-carbamic acid tert-butyl ester

    [0774] Starting from the compound of Preparation BB2 (280 mg) and Boc-(D)-alaninol (commercial; 223 mg), and proceeding in analogy to Preparation A3, step A3.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 0:1 to 1:0), as a colourless oil (548 mg; contaminated by residual PPh.sub.3O).

    [0775] MS3 (ESI, m/z): 400.98 [M+H.sup.+]; t.sub.R=0.95 min.

    A16. ii. {(R)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-1-methyl-ethyl}-carbamic acid tert-butyl ester

    [0776] Starting from intermediate A16.i (504 mg) and proceeding in analogy to Preparation A3, step A3.ii, the title compound was obtained as a off-white solid (463 mg; 100% yield) which was used directly in the subsequent step.

    [0777] MS3 (ESI, m/z): 356.97 [M+H.sup.+]; t.sub.R=0.94 min.

    Preparation A17: {(S)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-1-methyl-ethyl}-carbamic acid tert-butyl ester

    A17. i. {(S)-2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-1-methyl-ethyl}-carbamic acid tert-butyl ester

    [0778] Starting from the compound of Preparation BB2 (280 mg) and Boc-(L)-alaninol (commercial; 223 mg) and proceeding in analogy to Preparation A3, step A3.i, the title compound was obtained after purification by CC (Combiflash; Hept/EA 0:1 to 1:0) as a colourless oil (590 mg; contaminated by residual PPh.sub.3O).

    [0779] MS3 (ESI, m/z): 400.97 [M+H.sup.+]; t.sub.R=0.95 min.

    A 17.ii. {(S)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-1-methyl-ethyl}-carbamic acid tert-butyl ester

    [0780] Starting from intermediate A17.i (493 mg) and proceeding in analogy to Preparation A3, step A3.ii, the title compound was obtained as an off-white solid (462 mg; 100% yield) which was used directly in the subsequent step.

    [0781] MS3 (ESI, m/z): 356.97 [M+H.sup.+]; t.sub.R=0.95 min.

    Preparation A18: {2-[4-(3-formyl-phenyl)-pyridin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    A 18.i. {2-[4-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [0782] Starting from the compound of Preparation BB7 (280 mg) and N-Boc-ethanolamine (commercial; 208 mg) and proceeding in analogy to Preparation A3, step A3.i, the title compound was obtained after purification by CC (Combiflash; Hept/EA 0:1 to 1:0) as a colourless solid (343 mg; 77% yield).

    [0783] MS3 (ESI, m/z): 386.95 [M+H.sup.+]; t.sub.R=0.85 min.

    A 18.ii. {2-[4-(3-formyl-phenyl)-pyridin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [0784] Starting from intermediate A18.i (324 mg) and proceeding in analogy to Preparation A3, step A3.ii, the title compound was obtained as an off-white solid (338 mg) which was used directly in the subsequent step.

    [0785] MS3 (ESI, m/z): 342.97 [M+H.sup.+]; t.sub.R=0.85 min.

    Preparation A19: {5-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-pentyl}-carbamic acid tert-butyl ester

    A19.i. {5-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-pentyl}-carbamic acid tert-butyl ester

    [0786] Starting from compound of Preparation BB2 (280 mg) and 5-(Boc-amino)-1-pentanol (257 mg) and proceeding in analogy to Preparation A2, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a colourless oil (338 mg; 69% yield).

    [0787] MS3 (ESI, m/z): 429.06 [M+H.sup.+]; t.sub.R=0.99 min.

    A19. ii. {5-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-pentyl}-carbamic acid tert-butyl ester

    [0788] Starting from intermediate A19.i (303 mg) and proceeding in analogy to Preparation A7, step A7.ii the title compound was obtained as a yellow oil (300 mg; quant.).

    [0789] MS3 (ESI, m/z): 384.94 [M+H.sup.+]; t.sub.R=1.00 min.

    Preparation A20: [2-(3′-formyl-5-methoxy-biphenyl-3-yloxy)-ethyl]-carbamic acid tert-butyl ester

    A20. i. [2-(3′-[1,3]dioxolan-2-yl-5-methoxy-biphenyl-3-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [0790] Starting from the compound of preparation BB8 (200 mg) and N-Boc-ethanolamine (133 mg) and proceeding in analogy to Preparation A2, the title compound was obtained after purification by CC (Combiflash; Hept/EA 1:0 to 0:1) as an off-white solid (238 mg; 78% yield).

    [0791] MS3 (ESI, m/z): 416.01 [M+H.sup.+]; t.sub.R=0.94 min.

    A20. ii. [2-(3′-formyl-5-methoxy-biphenyl-3-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [0792] Starting from intermediate A20.i (219 mg) and proceeding in analogy to Preparation A7, step A7.ii the title compound was obtained as a yellow oil (213 mg; quant.).

    [0793] MS3 (ESI, m/z): 371.92 [M+H.sup.+]; t.sub.R=0.94 min.

    Preparation A21: 3-[6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-benzaldehyde

    A21. i. 4-{2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-ethyl}-morpholine

    [0794] Starting from the compound of Preparation BB2 (280 mg) and 4-(2-hydroxyethyl)morpholine (175 mg) and proceeding in analogy to Preparation A2, the title compound was obtained after purification by CC (Combiflash; Hept/EA 1:0 to 0:1) as a colourless oil (243 mg; 59% yield).

    [0795] MS3 (ESI, m/z): 356.96 [M+H.sup.+]; t.sub.R=0.80 min.

    A21. ii. 3-[6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-benzaldehyde

    [0796] Starting from intermediate A21.i (235 mg) and proceeding in analogy to Preparation A7, step A7.ii the title compound was obtained as a yellow oil (180 mg; quant.).

    [0797] MS3 (ESI, m/z): 313.01 [M+H.sup.+]; t.sub.R=0.595 min.

    Preparation A22: tert-butyl ((1R,3S)-3-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy) cyclopentyl)carbamate

    A22. i. Tert-butyl ((1R,3S)-3-((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy) cyclopentyl)carbamate

    [0798] Starting from the compound of Preparation BB1 (300 mg) and tert-butyl N-[(1R,3S)-3-hydroxycyclopentyl]carbamate (commercial; 245 mg), and proceeding in analogy to Preparation A3, step A3.i, the title compound was obtained after purification by CC (Combiflash; DCM to DCM/MeOH 4:1) as a yellow oil (200 mg; 43% yield).

    [0799] MS2 (ESI, m/z): 426.04 [M+H.sup.+]; t.sub.R=0.96 min.

    A22. ii. Tert-butyl ((1R,3S)-3-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy) cyclopentyl)carbamate

    [0800] Starting from intermediate A6.i (190 mg) and proceeding in analogy to Preparation A3, step A3.ii, the title compound was obtained as a yellow oil (185 mg; 100% yield) and used directly in the subsequent step.

    [0801] MS2 (ESI, m/z): 381.99 [M+H.sup.+]; t.sub.R=0.94 min.

    Preparation C1: (S)-2-(3′-formyl-biphenyl-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester

    C1.i. Tert-butyl (S)-2-(((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)methyl)azetidine-1-carboxylate

    [0802] A mixture of the compound of Preparation BB1 (100 mg), (S)-1-Boc-2-azetidinemethanol (commercial; 85 mg) and P(Ph).sub.3 (162 mg) in THF (4 mL) was treated dropwise with DEAD (40% in toluene; 0.18 mL) and the reaction mixture was further stirred at rt for 1 day. The solution was concentrated under reduced pressure and portioned between EA and water. The aq. layer was extracted with EA and the combined org. layers were washed with brine, dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The residue was purified by CC (Combiflash; Hept/EA 1:0 to 0:1) as a colourless oil (112 mg; 66% yield).

    [0803] MS2 (ESI, m/z): 412.02 [M+H.sup.+]; t.sub.R=0.96 min.

    C1.ii. (S)-2-(3′-formyl-biphenyl-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester

    [0804] A solution of intermediate C1.i (100 mg) and PTSA (1.2 mg) in acetone (1 mL) was stirred at rt for 4 days. The solution was filtered and evaporated under reduced pressure, affording a brown oil (quant.) which was used without further purification.

    [0805] MS2 (ESI, m/z): 367.99 [M+H.sup.+]; t.sub.R=0.94 min

    Preparation C2: tert-butyl (S)-2-(((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)methyl)pyrrolidine-1-carboxylate

    C2. i. Tert-butyl (S)-2-(((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)methyppyrrolidine-1-carboxylate

    [0806] Starting from the compound of Preparation BB1 (300 mg) and N-Boc-(S)-prolinol (commercial; 250 mg), and proceeding in analogy to Preparation C1, step C1.i (using however DIAD instead of DEAD), the title compound was obtained after purification by CC (Combiflash; Hept-EA 1:0 to 1:0) as a colourless oil (376 mg; 80% yield).

    [0807] MS2 (ESI, m/z): 426.06 [M+H.sup.+]; t.sub.R=1.02 min.

    C2.ii. Tert-butyl (S)-2-(((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)methyl)pyrrolidine-1-carboxylate

    [0808] Starting from intermediate C2.i (350 mg) and proceeding in analogy to Preparation C1, step C1.ii, the title compound was obtained as a brown oil and used directly in the subsequent step.

    [0809] MS2 (ESI, m/z): 382.00 [M+H.sup.+]; t.sub.R=1.01 min.

    Preparation C3: tert-butyl (RS)-3-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)pyrrolidine-1-carboxylate

    C3. i. Tert-butyl (RS)-3-((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)pyrrolidine-1-carboxylate

    [0810] Starting from the compound of Preparation BB1 (300 mg) and N-Boc-3-hydroxypyrrolidine (commercial; 228 mg), and proceeding in analogy to Preparation C1, step C1.i, the title compound was obtained after purification by CC (Combiflash; Hept/EA 1:0 to 1:0) as a colourless oil (520 mg; contaminated by residual PPh.sub.3O).

    [0811] MS2 (ESI, m/z): 412.03 [M+H.sup.+]; t.sub.R=0.96 min.

    C3. ii. Tert-butyl (RS)-3-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)pyrrolidine-1-carboxylate

    [0812] Starting from intermediate C3.i (500 mg) and proceeding in analogy to Preparation C1, step C1.ii, the title compound was obtained as an orange oil and used directly in the subsequent step.

    [0813] MS2 (ESI, m/z): 368.00 [M+H.sup.+]; t.sub.R=0.95 min.

    Preparation C4: (S)-3′-((1-methylazetidin-2-yl)methoxy)-[1,1′-biphenyl]-3-carbaldehyde

    C4.i. (S)-2-(((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)methyl)-1-methylazetidine

    [0814] Starting from the compound of Preparation BB1 (300 mg) and (5)-1-methyl-2-azetidinemethanol (commercial; 125 mg) and proceeding in analogy to Preparation C1, step C1.i, the title compound was obtained after purification by CC (Combiflash; Hept/EA 0:1 to 1:0) as a brown oil (65 mg; 16% yield).

    [0815] MS1 (ESI, m/z): 326.04 [M+H.sup.+]; t.sub.R=0.66 min.

    C4.ii. (S)-3′-((1-methylazetidin-2-yl)methoxy)-[1,1′-biphenyl]-3-carbaldehyde

    [0816] Starting from intermediate C4.i (57 mg) and proceeding in analogy to Preparation C1, step C1.ii, the title compound was obtained as a colourless oil (42 mg; 85% yield) which was used directly in the subsequent step.

    [0817] MS3 (ESI, m/z): 282.04 [M+H.sup.+]; t.sub.R=0.63 min.

    Preparation C5: tert-butyl 3-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)azetidine-1-carboxylate

    C5. i. Tert-butyl 3-((3′-(1,3-dioxolan-2-yl)-[1,1′-biphenyl]-3-yl)oxy)azetidine-1-carboxylate

    [0818] Starting from 3-(3-bromophenoxy)-1-azetidinecarboxylic acid tert-butyl ester (300 mg; prepared according to WO 2010/059390), 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (252 mg; commercial), Pd(PPh.sub.3).sub.4 (53 mg; commercial) and Na.sub.2CO.sub.3 (1M, 1.01 mL) and proceeding in analogy to Preparation BB1, but using EtOH and toluene as solvent, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a yellow oil (114 mg; 31% yield).

    [0819] MS3 (ESI, m/z): 397.98 [M+H.sup.+]; t.sub.R=0.98 min.

    C5.ii. Tert-butyl 3-((3′-formyl-[1,1′-biphenyl]-3-yl)oxy)azetidine-1-carboxylate

    [0820] A solution of intermediate C5.i (110 mg) in THF (1.5 mL) was heated at 50° C. for 5 min in presence of 1M HCl (0.52 mL). The reaction mixture was allowed to cool to rt, treated with excess sat. NaHCO.sub.3 solution and extracted 5 times with DCM/MeOH. The combined org. layers were washed with brine, dried over MgSO.sub.4, filtered and concentrated under reduced pressure, affording an orange oil (85 mg; 87% yield).

    [0821] MS3(ESI, m/z): 297.96 [M+H].sup.+; t.sub.R=0.97 min.

    Preparation C6: tert-butyl 3-(((6-(3-formylphenyl)pyridin-2-yl)oxy)methyl)azetidine-1-carboxylate

    C6.i. Tert-butyl 3-(((6-(3-(1,3-dioxolan-2-yl)phenyl)pyridin-2-yl)oxy)methyl)azetidine-1-carboxylate

    [0822] Starting from the compound of Preparation BB2 (108 mg) and tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (100 mg; commercial) and proceeding in analogy to Preparation C1, step C1.i, the title compound (182 mg; 99% yield) was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:1), as a colourless oil.

    [0823] MS1 (ESI, m/z): 413.17 [M+H.sup.+]; t.sub.R=0.97 min.

    C6.ii. Tert-butyl 3-(((6-(3-formylphenyl)pyridin-2-yl)oxy)methyl)azetidine-1-carboxylate

    [0824] Starting from intermediate C6.i (170 mg) and proceeding in analogy to Preparation C5, step C5.ii. the title compound was obtained as a colourless solid (152 mg; 100% yield).

    [0825] MS1 (ESI, m/z): 369.07 [M+H.sup.+]; t.sub.R=0.98 min.

    Preparation C7: 3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid tert-butyl ester

    C7. i. 3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid tert-butyl ester

    [0826] Starting from the compound of Preparation BB2 (150 mg) and 1-Boc-3-hydroxyazetidine (107 mg) and proceeding in analogy to Preparation C1, step C1.i, the title compound was obtained after purification by CC (Combiflash; Hept to Hept/EA 1:1) as a yellow oil (186 mg; 76% yield).

    [0827] MS3 (ESI, m/z): 398.96 [M+H.sup.+]; t.sub.R=0.98 min.

    C7. ii. 3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid tert-butyl ester

    [0828] Starting from intermediate C7.i (175 mg) and proceeding in analogy to Preparation C1, step C1.ii, the title compound was obtained as a colourless oil (151 mg; 100% yield) and used directly in the subsequent step.

    [0829] MS3 (ESI, m/z): 354.94 [M+H.sup.+]; t.sub.R=0.89 min.

    Preparation C8: (S)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-azetidine-1-carboxylic acid tert-butyl ester

    C8.i. (S)-2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxymethyl]-azetidine-1-carboxylic acid tert-butyl ester

    [0830] Starting from the compound of Preparation BB2 (280 mg) and (S)-1-Boc-2-azetidinemethanol (237 mg; commercial) and proceeding in analogy to Preparation C1, step C1.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 0:1), as a colourless oil (608 mg; contaminated by some PPh.sub.3O).

    [0831] MS3 (ESI, m/z): 413.01 [M+H.sup.+]; t.sub.R=0.97 min.

    C8.ii. (S)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-azetidine-1-carboxylic acid tert-butyl ester

    [0832] Starting from intermediate C8.i (591 mg) and proceeding in analogy to Preparation C1, step C1 .ii, the title compound was obtained as an off-white solid (584 mg; 100% yield) and used directly in the subsequent step.

    [0833] MS3 (ESI, m/z): 368.93 [M+H.sup.+]; t.sub.R=0.97 min.

    Preparation C9: rac-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester

    C9. i. Rac-2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester

    [0834] Starting from the compound of Preparation BB2 (280 mg) and tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (275 mg; commercial) and proceeding in analogy to Preparation C1, step C1.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 0:1), as a colourless oil (670 mg; contaminated by some PPh.sub.3O).

    [0835] MS3 (ESI, m/z): 443.05 [M+H.sup.+]; t.sub.R=0.96 min.

    C9. ii. Rac-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester

    [0836] Starting from intermediate C9.i (634 mg) and proceeding in analogy to Preparation C1, step C1.ii, the title compound was obtained as an off-white solid (616 mg; 100% yield) which was used directly in the subsequent step.

    [0837] MS3 (ESI, m/z): 398.97 [M+H.sup.+]; t.sub.R=0.97 min.

    Preparation C10: rac-3-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester

    C10. i. Rac-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester

    [0838] Starting from the compound of Preparation BB2 (280 mg) and 4-Boc-(3-hydroxymethyl)morpholine (275 mg; commercial) and proceeding in analogy to Preparation C1, step C1.i, the title compound was obtained after purification by CC (Combiflash; Hept to Hept/EA 0:1) as a colourless oil (533 mg; contaminated by residual PPh.sub.3O).

    [0839] MS3 (ESI, m/z): 443.05 [M+H.sup.+]; t.sub.R=0.94 min.

    C10. ii. Rac-3-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-morpholine-4-carboxylic acid tert-butyl ester

    [0840] Starting from intermediate C10.i (515 mg) and proceeding in analogy to Preparation C1, step C1 .ii, the title compound was obtained as an off-white solid (494 mg; 100% yield) and used directly in the subsequent step.

    [0841] MS3 (ESI, m/z): 398.99 [M+H.sup.+]; t.sub.R=0.95 min.

    Preparation C11: rac-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

    C11. i. Rac-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

    [0842] Starting from the compound of Preparation BB2 (280 mg) and 1-Boc-3-hydroxypiperidine (255 mg; commercial) and proceeding in analogy to Preparation C1, step C1.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 0:1), as a colourless oil (412 mg; 84% yield).

    [0843] MS3 (ESI, m/z): 427.05 [M+H.sup.+]; t.sub.R=0.99 min.

    C11.ii. Rac-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

    [0844] Starting from intermediate C11.i (402 mg) and proceeding in analogy to Preparation C1, step C1.ii, the title compound was obtained as an off-white solid (382 mg; 100% yield) which was used directly in the subsequent step.

    [0845] MS3 (ESI, m/z): 382.96 [M+H.sup.+]; t.sub.R=1.00 min.

    Preparation C12: (3R*,4S*)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

    C12.i. (3S*,4S*)-3-hydroxy-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0846] A solution of trans-4-methoxy-3-pyrrolidinol hydrochloride (256 mg) and TEA (0.58 mL) in water (1.2 mL) and dioxane (3 mL) was treated with di-tert-butyl dicarbonate (436 mg) and further stirred at rt for 2 h. The reaction mixture was diluted with EA and washed with water. The aq. layer was extracted with EA. The combined org. layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure affording a light yellow oil (360 mg; 99% yield).

    [0847] MS3 (ESI, m/z): 218.20 [M+H.sup.+]; t.sub.R=0.59 min.

    C12.ii. (3R*,4S*)-3-(6-chloro-pyridin-2-yloxy)-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0848] Starting from 6-chloro-2-hydroxypyridine (150 mg) and intermediate C12.i (247 mg) and proceeding in analogy to Preparation C1, step C1.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 0:1), as a colourless solid (240 mg; 64% yield).

    [0849] MS3 (ESI, m/z): 328.92 [M+H.sup.+]; t.sub.R=0.90 min.

    C12.iii. (3R*,4S*)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0850] Intermediate C12.ii (215 mg) and 3-formylphenylboronic acid (103 mg; commercial) were added to a mixture of aq. NaHCO.sub.3 (2M; 0.33 mL), toluene (2 mL), EtOH (4 mL) and water (2 mL). N2 was bubbled through the reaction mixture, Pd(PPh.sub.3).sub.4 (38 mg) was added and the reaction mixture was further stirred at 90° C. for 90 min. The reaction mixture was cooled to rt and partitioned between water and EA. The aq. layer was extracted with EA and the combined org. layers were washed with brine and dried over MgSO.sub.4, affording after purification by CC (Combiflash; Hept to Hept/EA 2:1) a light yellow oil (172 mg; 66% yield).

    [0851] MS1 (ESI, m/z): 398.95 [M+H.sup.+]; t.sub.R=0.94 min.

    Preparation C13: 3-[6-(1-methyl-azetidin-3-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    C13.i. 3-(6-chloro-pyridin-2-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester

    [0852] Starting from 6-chloro-2-hydroxypyridine (commercial; 300 mg) and tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (commercial; 425 mg) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 4:1), as a colourless oil (610 mg; 89% yield).

    [0853] MS3 (ESI, m/z): 298.96 [M-41]; t.sub.R=0.92 min.

    C13. ii. 2-(azetidin-3-ylmethoxy)-6-chloro-pyridine

    [0854] A solution of intermediate C13.i (580 mg) in DCM (8 mL) was treated with TFA (3.31 mL) and further stirred at rt for 10 min. Sat. aq. NaHCO.sub.3 was added and the mixture was extracted with DCM. The org. layer was dried over MgSO.sub.4, filtered and concentrated under reduced pressure The residue was purified by prep-HPLC (method 2), affording a colourless foam (218 mg; 51% yield).

    [0855] MS3 (ESI, m/z): 199.16 [M+H.sup.+]; t.sub.R=0.49 min.

    C13.iii. 2-chloro-6-(1-methyl-azetidin-3-ylmethoxy)-pyridine

    [0856] To a solution of intermediate C13.ii (100 mg) and TEA (0.558 mL) in DCM (3 mL) were added 37% aq. formaldehyde (0.511 mL) and NaBH(OAc).sub.3 (480 mg) and further stirred at rt for 2.5 h. The residue was partitioned between sat. aq. NaHCO.sub.3 and DCM/MeOH 9:1. The org. layer was separated and dried over MgSO.sub.4, filtered and concentrated under reduced pressure, affording a light yellow oil (51 mg; 48% yield).

    [0857] MS3 (ESI, m/z): 213.15 [M+H.sup.+]; t.sub.R=0.50 min.

    C13.iv. 3-[6-(1-methyl-azetidin-3-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    [0858] Starting from intermediate C13.iii (48 mg), 3-formylphenylboronic acid (35.5 mg; commercial), Pd(PPh.sub.3).sub.4 (13 mg; commercial) and Na.sub.2CO.sub.3 (1M; 0.226 mL) and proceeding in analogy to Preparation BB1, but using EtOH and water as solvents, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as a yellow oil (37 mg; 58% yield).

    [0859] MS3 (ESI, m/z): 283.02 [M+H.sup.+]; t.sub.R=0.62 min.

    Preparation C14: 3-[6-(3-formyl-phenyl)-pyridazin-4-yloxy]-azetidine-1-carboxylic acid tert-butyl ester

    C14.i. 3-[6-(3-[1 ,3]dioxolan-2-yl-phenyl)-pyridazin-4-yloxy]-azetidine-1-carboxylic acid tert-butyl ester

    [0860] A suspension of NaH (301 mg) in dry THF (3 mL) was cooled to 0° C. A solution of 1-Boc-3-azetidinol (1.33 g; commercial) in dry THF (3 mL) was added and the mixture was stirred at 0° C. for 45 min. THF (3 mL) was added followed by a mixture of the compound of Preparation BB3 (263 mg) dissolved in THF (2 mL) at 0° C. and stirred at rt for 1 day. The mixture was concentrated under reduced pressure and the residue was portioned between EA and water. The layers were separated and the aq. phase was extracted twice with EA. The combined org. layers were dried over MgSO.sub.4, filtered, evaporated and purified by CC (Combiflash; Hept/EA 1:0 to 1:4), affording a yellow sticky oil (144 mg; 36% yield).

    [0861] MS1 (ESI, m/z): 400.14 [M+H.sup.+]; t.sub.R=0.83 min.

    C14.ii. 3-[6-(3-formyl-phenyl)-pyridazin-4-yloxy]-azetidine-1-carboxylic acid tert-butyl ester

    [0862] A solution of intermediate C14.i (72 mg) in MeCN/MeOH (1:1; 2.6 mL) was stirred at 80° C. for 2 h in presence of CBr4 (120 mg). The mixture was cooled to rt, basified with sat. aq. NaHCO.sub.3 and extracted with EA. The org. layer was dried over MgSO.sub.4, filtered and concentrated under reduced pressure, affording a yellow solid (144 mg; crude product) which was not further purified.

    [0863] MS3 (ESI, m/z): 355.92 [M+H.sup.+]; t.sub.R=0.84 min.

    Preparation C15: (R)-3-[2-(3-formyl-phenyl)-pyrimidin-4-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0864] Starting from (R)-3-(2-chloro-pyrimidin-4-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg; commercial), 3-formylphenylboronic acid (250 mg; commercial), Pd(PPh.sub.3).sub.4 (77 mg) and K.sub.2CO.sub.3 (692 mg) and proceeding in analogy to Preparation BB1, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as an orange oil (592 mg; 96% yield).

    [0865] MS3 (ESI, m/z): 369.82 [M+H.sup.+]; t.sub.R=0.89 min.

    Preparation C16: (R)-3-[6-(3-formyl-phenyl)-pyrimidin-4-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0866] Starting from (R)-3-(6-chloro-pyrimidin-4-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg; commercial), 3-formylphenylboronic acid 250 mg; commercial), Pd(PPh.sub.3).sub.4 (77 mg) and K.sub.2CO.sub.3 (692 mg) and proceeding in analogy to Preparation BB1, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a colourless solid (328 mg; 53% yield).

    [0867] MS3 (ESI, m/z): 369.87 [M+H.sup.+]; t.sub.R=0.91 min.

    Preparation C17: {(1R*,5S*)-3-[2-(3′-formyl-biphenyl-3-yloxy)-ethyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-carbamic acid tert-butyl ester

    C17.i. 3′-[1,3]dioxolan-2-yl-biphenyl-3-ol

    [0868] Starting from 3-hydroxyphenylboronic acid (5.00 g; commercial), 2-(3-bromophenyl)-1,3-dioxolane (8.30 g; commercial), Pd(PPh.sub.3).sub.4 (1.68 g) and K.sub.2CO.sub.3 (15.0 g) and proceeding in analogy to Preparation BB1, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a yellow oil (7.05 g; 80% yield).

    [0869] MS3 (ESI, m/z): 243.07 [M+H.sup.+]; t.sub.R=0.78 min.

    C17.ii. 2-[3′-(2-bromo-ethoxy)-biphenyl-3-yl]-[1,3]dioxolane

    [0870] Starting from intermediate C17.i (279 mg) and 2-bromoethanol (0.189 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 0:1 to 1:0), as a colourless oil (146 mg; 36% yield).

    [0871] MS3 (ESI, m/z): 348.72 [M+H+]; t.sub.R=0.94 min.

    C17. iii. {(1R*,5S*)-3-[2-(3′-[1,3]dioxolan-2-yl-biphenyl-3-yloxy)-ethyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-carbamic acid tert-butyl ester

    [0872] Intermediate C17.ii (130 mg) and K.sub.2CO.sub.3 (69 mg) were suspended with DMF. 6-(Boc-amino)-3-azabicyclo[3.1.0]hexane (81 mg; commercial) was added portionwise and the mixture was stirred at rt for 1 day. The mixture was concentrated under reduced pressure and the residue was portioned between EA and water. The aq. layer was extracted with EA and the combined org. layers were washed with water and brine, dried over MgSO.sub.4 and concentrated under reduced pressure. The title compound was obtained, after purification by CC (Combiflash; Hept/EA 0:1 to 1:0), as a yellow oil (108 mg; 62% yield).

    [0873] MS3 (ESI, m/z): 457.10 [M+H+]; t.sub.R=0.73 min.

    C17. iv. {(1R*,5S*)-3-[2-(3′-formyl-biphenyl-3-yloxy)-ethyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-carbamic acid tert-butyl ester

    [0874] Starting from intermediate C17.iii (100 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as an off-white solid (70 mg; 77% yield).

    [0875] MS3 (ESI, m/z): 423.06 [M+H+]; t.sub.R=0.72 min.

    Preparation C18: (R)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    C18. i. (R)-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0876] Starting from the compound of Preparation BB2 (100 mg) and (S)—N-Boc-3-pyrrolidinol (85 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained as a yellow oil (421 mg; crude product) which was used in the next step without further purification.

    [0877] MS3 (ESI, m/z): 413.04 [M+H.sup.+]; t.sub.R=0.98 min.

    C18.ii. (R)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0878] Starting from intermediate C18.i (420 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow oil (396 mg).

    [0879] MS3 (ESI, m/z): 369.04 [M+H.sup.+]; t.sub.R=0.98 min.

    Preparation C19: (S)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    C19. i. (S)-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0880] Starting from the compound of Preparation BB2 (100 mg) and (R)-N-Boc-3-pyrrolidinol (85 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained as a yellow oil (402 mg; quant.).

    [0881] MS3 (ESI, m/z): 413.06 [M+H.sup.+]; t.sub.R=0.98 min.

    C19.ii. (S)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0882] Starting from intermediate C19.i (420 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow oil (396 mg; quant.).

    [0883] MS3 (ESI, m/z): 369.04 [M+H.sup.+]; t.sub.R=0.98 min.

    Preparation C20: 3-[6-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C20. i. 2-(3-[1,3]dioxolan-2-yl-phenyl)-6-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridine

    [0884] Starting from the compound of Preparation BB2 (100 mg) and (S)-(+)-1-methyl-3-pyrrolidinol (0.050 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained as a yellow oil (396 mg; quant.).

    [0885] MS3 (ESI, m/z): 327.04 [M+H.sup.+]; t.sub.R=0.63 min.

    C20.ii. 3-[6-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [0886] Starting from intermediate C20.i (396 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as an orange oil (376 mg; quant.).

    [0887] MS3 (ESI, m/z): 283.02 [M+H+]; t.sub.R=0.61 min.

    Preparation C21: 3-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C21. i. 2-(3-[1,3]dioxolan-2-yl-phenyl)-6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridine

    [0888] Starting from the compound of Preparation BB2 (100 mg) and (R)-(−)-1-methyl-3-pyrrolidinol (0.050 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained as a brown oil (419 mg; quant.).

    [0889] MS3 (ESI, m/z): 327.04 [M+H.sup.+]; t.sub.R=0.63 min.

    C21. ii. 3-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [0890] Starting from intermediate C21.i (419 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as an orange oil (382 mg; quant.).

    [0891] MS3 (ESI, m/z): 283.06 [M+H.sup.+]; t.sub.R=0.61 min.

    Preparation C22: 3-[6-(1-methyl-azetidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C22.i. 2-(3-[1,3]dioxolan-2-yl-phenyl)-6-(1-methyl-azetidin-3-yloxy)-pyridine

    [0892] Starting from the compound of Preparation BB2 (100 mg) and 1-methyl-azetidin-3-ol (39 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as a yellow oil (29 mg; 23% yield).

    [0893] MS3 (ESI, m/z): 313.04 [M+H.sup.+]; t.sub.R=0.63 min.

    C22. ii. 3-[6-(1-methyl-azetidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [0894] Starting from intermediate C22.i (25 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow oil (21 mg; 98% yield).

    [0895] MS3 (ESI, m/z): 269.02 [M+H.sup.+]; t.sub.R=0.61 min.

    Preparation C23: 3-[6-((S)-1-methyl-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    C23.i. 2-(3-[1,3]dioxolan-2-yl-phenyl)-6-((S)-1-methyl-azetidin-2-ylmethoxy)-pyridine

    [0896] Starting from the compound of Preparation BB2 (100 mg) and (5)-1-methyl-2-azetidinemethanol (45 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as a yellow oil (29 mg; 20% yield).

    [0897] MS3 (ESI, m/z): 327.05 [M+H.sup.+]; t.sub.R=0.63 min.

    C23. ii. 3-[6-((S)-1-methyl-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    [0898] Starting from intermediate C23.i (25 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow oil (20 mg; quant.).

    [0899] MS3 (ESI, m/z): 283.04 [M+H.sup.+]; t.sub.R=0.61 min.

    Preparation C24: (R)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-azetidine-1-carboxylic acid tert-butyl ester

    C24. i. (R)-2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxymethyl]-azetidine-1-carboxylic acid tert-butyl ester

    [0900] Starting from the compound of Preparation BB2 (150 mg) and (R)-1-Boc-2-azetidinemethanol (138 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:1), as a yellow oil (247 mg; 90% yield).

    [0901] MS3 (ESI, m/z): 413.05 [M+H.sup.+]; t.sub.R=0.97 min.

    C24. ii. (R)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-azetidine-1-carboxylic acid tert-butyl ester

    [0902] Starting from intermediate C24.i (60 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless oil (56 mg; quant.).

    [0903] MS3 (ESI, m/z): 369.00 [M+H.sup.+]; t.sub.R=0.97 min.

    Preparation C25: 3-[6-((R)-1-methyl-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    C25.i. 3-[6-((R)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]benzaldehyde trifluoroacetate

    [0904] Starting from intermediate C24.i (170 mg) and proceeding in analogy to Preparation C13, step C13.ii, the title compound was obtained without further purification as a yellowish oil (171 mg; quant.).

    [0905] MS3 (ESI, m/z): 269.06 [M+H.sup.+]; t.sub.R=0.61 min.

    C25. ii. 2-((R)-1-azetidin-2-ylmethoxy)-6-(3-dimethoxymethyl-phenyl)-pyridine

    [0906] A solution of intermediate C25.i (165 mg), trimethyl orthoformate (0.63 mL) and PTSA (2.46 mg) in MeOH (5.0 mL) was stirred at 50° C. for 1 day. Sat. aq. NaHCO.sub.3 and EA were added, the layers were separated and the aq. layer was twice extracted with EA, dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The title compound was obtained as a yellow oil (119 mg; 88% yield; 25% pure).

    [0907] MS3 (ESI, m/z): 315.03 [M+H.sup.+]; t.sub.R=0.65 min.

    C25.iii. 2-(3-dimethoxymethyl-phenyl)-6-((R)-1-methyl-azetidin-2-ylmethoxy)-pyridine

    [0908] Starting from intermediate C25.ii (110 mg) and 37% aq. formaldehyde (0.089 mL) and proceeding in analogy to Preparation C13, step C13.iii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless oil (15 mg; 52% yield).

    [0909] MS3 (ESI, m/z): 239.04 [M+H+]; t.sub.R=0.66 min.

    C25. iv. 3-[6-((R)-1-methyl-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    [0910] Starting from intermediate C25.iii (10 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellowish oil (9 mg; quant.).

    [0911] MS3 (ESI, m/z): 283.03 [M+H.sup.+]; t.sub.R=0.62 min.

    Preparation C26: rac-3-[6-(1-ethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C26.i. Rac-2-(3-[1,3]dioxolan-2-yl-phenyl)-6-(1-ethyl-pyrrolidin-3-yloxy)-pyridine

    [0912] Starting from the compound of Preparation BB2 (332 mg) and 1-ethyl-3-pyrrolidinol (0.188 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a brown oil (180 mg; 39% yield).

    [0913] MS3 (ESI, m/z): 341.05 [M+H.sup.+]; t.sub.R=0.66 min.

    C26.ii. Rac-3-[6-(1-ethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [0914] Starting from intermediate C26.i (156 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a reddish solid (116 mg; 85% yield).

    [0915] MS3 (ESI, m/z): 297.04 [M+H.sup.+]; t.sub.R=0.63 min.

    Preparation C27: 3-[6-(1-methyl-piperidin-4-yloxy)-pyridin-2-yl]-benzaldehyde

    C27. i. 2-(3-[1,3]dioxolan-2-yl-phenyl)-6-(1-methyl-piperidin-4-yloxy)-pyridine

    [0916] Starting from the compound of Preparation BB2 (200 mg) and 4-hydroxy-1-methylpiperidine (0.108 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a yellow oil (106 mg; 38% yield).

    [0917] MS3 (ESI, m/z): 341.05 [M+H.sup.+]; t.sub.R=0.65 min.

    C27.ii. 3-[6-(1-methyl-piperidin-4-yloxy)-pyridin-2-yl]-benzaldehyde

    [0918] Starting from intermediate C27.i (97 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a reddish solid (80 mg; 95% yield).

    [0919] MS3 (ESI, m/z): 297.06 [M+H.sup.+]; t.sub.R=0.64 min.

    Preparation C28: 6-((S)-1-methyl-pyrrolidin-3-yloxy)-[2,4]bipyridinyl-2′-carbaldehyde

    C28. i. 2-bromo-6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridine

    [0920] Starting from 6-bromopyridin-2-ol (1.5 g; commercial) and (R)-(−)-1-methyl-3-pyrrolidinol (1.02 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained after purification by CC (Combiflash; DCM to DCM/MeOH 9:1) as a light yellow liquid (1.3 g; 60% yield).

    [0921] MS3 (ESI, m/z): 258.94 [M+H.sup.+]; t.sub.R=0.51 min.

    C28.ii. 2-((S)-1-methyl-pyrrolidin-3-yloxy)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine

    [0922] A mixture of intermediate C28.i (350 mg), bis(pinacolato)diboron (388 mg; commercial), potassium acetate (200 mg), Tris(dibenzylideneacetone)dipalladium(0) (37.4 mg) and tricyclohexylphosphine (45.8 mg) in dioxane (5 mL) was degassed for 5 min with N.sub.2 and sealed in a Schlenk flask. The resulting dark brown suspension was stirred at 100° C. for 1.5 h. The mixture was cooled down to rt, diluted with EA, filtered through a glass fiber filter and concentrated under reduced pressure, the title compound was obtained as a yellow oil (895 mg; quant.) and used in the next step without further purification.

    [0923] MS3 (ESI, m/z): 305.06 [M+H.sup.+]; t.sub.R=0.36 min.

    C28.iii. 6-((S)-1-methyl-pyrrolidin-3-yloxy)-[2,4′]bipyridinyl-2′-carbaldehyde

    [0924] A mixture of intermediate C28.ii (295 mg), 4-bromopyridine-2-carbaldehyde (73.6 mg; commercial), cesium carbonate (511 mg), copper(I) chloride (39.6 mg), palladium(II) acetate (4.44 mg) and 1,1′-bis(diphenylphosphino)ferrocene (22.2 mg) in dioxane (3 mL) was degassed for 10 min with N.sub.2 and sealed in a glass vial. The resulting suspension was stirred at 100° C. for 1 h. The mixture was cooled down to rt suspended with EA and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The title compound was obtained, after purification by CC (Combiflash; DCM; DCM/MeOH 9/1), as an orange oil (56 mg; 51% yield).

    [0925] MS3 (ESI, m/z): 284.02 [M+H.sup.+]; t.sub.R=0.56 min.

    Preparation C29: 6′-((S)-1-methyl-pyrrolidin-3-yloxy)-[2,2]bipyridinyl-6-carbaldehyde:

    [0926] Starting from intermediate C28.ii (295 mg) and 6-bromo-2-pyridinecarboxaldehyde (74.4 mg; commercial) and proceeding in analogy to Preparation C28, step C28.iii, the title compound was obtained as a brown oil (61 mg; 56% yield).

    [0927] MS3 (ESI, m/z): 284.04 [M+H.sup.+]; t.sub.R=0.59 min.

    Preparation C30: 3-[4(S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    C30.i. 2-(3-[1,3]dioxolan-2-yl-phenyl)-6-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine

    [0928] Starting from the compound of Preparation BB2 (200 mg) and (S)-(−)-1-methyl-2-pyrrolidinemethanol (62.5 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained after purification by CC (Combiflash; Hept/EA 1:0 to 0:1) as a yellow oil (100 mg; 60% yield).

    [0929] MS3 (ESI, m/z): 341.06 [M+H.sup.+]; t.sub.R=0.65 min.

    C30.ii. 3-[6-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    [0930] Starting from intermediate C30.i (96 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow solid (73 mg; 87% yield).

    [0931] MS3 (ESI, m/z): 297.05 [M+H.sup.+]; t.sub.R=0.64 min.

    Preparation C31: (2S,4S)-4-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    C31.i. (2S,4S)-4-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0932] Starting from the compound of Preparation BB2 (120 mg) and (2S,4R)-4-hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (109 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a yellow oil (242 mg; quant.).

    [0933] MS3 (ESI, m/z): 427.11 [M+H.sup.+]; t.sub.R=1.01 min.

    C31. ii. (2S,4S)-4-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0934] Starting from intermediate C31.i (203 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow solid (217 mg; quant).

    [0935] MS3 (ESI, m/z): 383.04 [M+H.sup.+]; t.sub.R=1.02 min.

    Preparation C32: (R)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    C32.i. (R)-2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0936] Starting from the compound of Preparation BB2 (120 mg) and N-Boc-D-prolinol (110 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a yellow oil (200 mg; 95% yield).

    [0937] MS3 (ESI, m/z): 427.10 [M+H.sup.+]; t.sub.R=1.00 min.

    C32. ii. (R)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0938] Starting from intermediate C32.i (183 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless oil (179 mg; quant).

    [0939] MS3 (ESI, m/z): 383.03 [M+H.sup.+]; t.sub.R=1.01 min.

    Preparation C33: (S)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    C33.i. (S)-2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0940] Starting from the compound of Preparation BB2 (120 mg) and N-Boc-L-prolinol (109 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a yellow oil (238 mg; quant.).

    [0941] MS3 (ESI, m/z): 427.10 [M+H.sup.+]; t.sub.R=1.00 min.

    C33.ii. (S)-2-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0942] Starting from intermediate C33.i (201 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless oil (213 mg; quant.).

    [0943] MS3 (ESI, m/z): 383.01 [M+H.sup.+]; t.sub.R=1.01 min.

    Preparation C34: rac-3-[6-(1-isopropyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C34. i. Rac-2-(3-[1,3]dioxolan-2-yl-phenyl)-6-(1-isopropyl-pyrrolidin-3-yloxy)-pyridine

    [0944] Starting from the compound of Preparation BB2 (120 mg) and 1-isopropyl-3-pyrrolidinol (73.8 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a colourless oil (72 mg; 41% yield).

    [0945] MS3 (ESI, m/z): 355.03 [M+H.sup.+]; t.sub.R=0.67 min.

    C34. ii. Rac-3-[6-(1-isopropyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [0946] Starting from intermediate C34.i (71 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as an off-white solid (54 mg; 87% yield).

    [0947] MS3 (ESI, m/z): 311.05 [M+H.sup.+]; t.sub.R=0.77 min.

    Preparation C35: (RS)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-(RS)-2-methyl-azetidine-1-carboxylic acid tert-butyl ester

    C35.i. (RS)-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-(RS)-2-methyl-azetidine-1-carboxylic acid tert-butyl ester

    [0948] Starting from the compound of Preparation BB2 (120 mg) and tert-butyl 3-hydroxy-2-methylazetidine-1-carboxylate (105 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a colourless oil (56 mg; 28% yield).

    [0949] MS3 (ESI, m/z): 413.08 [M+H.sup.+]; t.sub.R=1.00 min.

    C35. ii. (RS)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-(RS)-2-methyl-azetidine-1-carboxylic acid tert-butyl ester

    [0950] Starting from intermediate C35.i (48 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as an off-white solid (47 mg; quant.).

    [0951] MS3 (ESI, m/z): 369.00 [M+H.sup.+]; t.sub.R=0.67 min.

    Preparation C36: 3-[4-methoxy-6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C36.i. 6-bromo-4-methoxy-pyridin-2-ol

    [0952] A dry tube was filled with (1,5-cyclooctadiene)(methoxy)iridium(I) dimer (18 mg) and 4,4′-di-tert-butyl-2,2′-dipyridyl (14.3 mg) and filled with N.sub.2. 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.232 mL) and 2-bromo-4-methoxypyridine (250 mg; commercial) in Hept (2.6 mL) were added and the brown solution was stirred at rt for 1 day. (1,5-cyclooctadiene)(methoxy)iridium(I) dimer (18 mg) and 4,4′-di-tert-butyl-2,2′-dipyridyl (14.3 mg) were added again and the mixture was stirred at 50-80° C. for 3 days. The mixture was diluted with THF (10 mL) and oxone (monopersulfate compound in 10 mL H.sub.2O; 899 mg) was added within 15 min under vigorous stirring. The reaction mixture was quenched with 40% aq. NaHSO.sub.3 (10 mL), brine (10 mL) and the aq. mixture was extracted twice with EA. The combined org. layers were washed with water, dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 3:1), as a colourless solid (85 mg; 31% yield).

    [0953] MS3 (ESI, m/z): 205.98 [M+H.sup.+]; t.sub.R=0.52 min.

    C36.ii. 2-bromo-4-methoxy-6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridine

    [0954] Starting from intermediate C36.i (60 mg) and (R)-(−)-1-methyl-3-pyrrolidinol (0.036 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as an orange oil (39 mg; 46% yield).

    [0955] MS3 (ESI, m/z): 286.94 [M+H.sup.+]; t.sub.R=0.57 min.

    C36.iii. 3-[4-methoxy-6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [0956] Starting from intermediate C36.ii (35 mg) and 3-formylphenylboronic acid (20 mg; commercial) and proceeding in analogy to Preparation BB1, but irradiate the reaction mixture in the microwave at 110° C. for 45 min, the title compound was obtained as an orange oil (35 mg; 92% yield).

    [0957] MS3 (ESI, m/z): 313.05 [M+H.sup.+]; t.sub.R=0.65 min.

    Preparation C37: 3-[4-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrimidin-2-yl]-benzaldehyde

    C37.i. 2-chloro-4-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrimidine

    [0958] Starting from 2-chloro-4-hydroxypyrimidine (70 mg; commercial) and (R)-(−)-1-methyl-3-pyrrolidinol (0.0628 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as a yellow solid (80 mg; 72% yield).

    [0959] MS3 (ESI, m/z): 214.08 [M+H.sup.+]; t.sub.R=0.38 min.

    C37.ii. 3-[4-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrimidin-2-yl]-benzaldehyde

    [0960] Starting from intermediate C37.i (80 mg), 3-formylphenylboronic acid (30 mg; commercial), Pd(PPh.sub.3).sub.4 (22 mg) and K.sub.2CO.sub.3 (78 mg) and proceeding in analogy to Preparation BB1, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as a yellow oil (11 mg; 10% yield).

    [0961] MS3 (ESI, m/z): 284.02 [M+H.sup.+]; t.sub.R=0.56 min.

    Preparation C38: 6-((S)-1-methyl-pyrrolidin-3-yloxy)-[2,3]bipyridinyl-5′-carbaldehyde

    [0962] Starting from intermediate C28.ii (250 mg) and 5-bromo-3-pyridinecarboxaldehyde (74.5 mg; commercial) and proceeding in analogy to Preparation C28, step C28.iii, the title compound was obtained as a yellow oil (62 mg; 59% yield).

    [0963] MS3 (ESI, m/z): 284.02 [M+H.sup.+]; t.sub.R=0.54 min.

    Preparation C39: 6′-((S)-1-methyl-pyrrolidin-3-yloxy)-[2,2]bipyridinyl-4-carbaldehyde

    [0964] Starting from intermediate C28.ii (250 mg) and 2-bromo-4-formylpyridine (74 mg; commercial) and proceeding in analogy to Preparation C28, step C28.iii, the title compound was obtained as a yellow oil (55 mg; 59% yield).

    [0965] MS3 (ESI, m/z): 284.01 [M+H.sup.+]; t.sub.R=0.57 min.

    Preparation C40: 3-[6-((R)-1-methyl-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    C40.i. 2-(3-[1,3]dioxolan-2-yl-phenyl)-6-((R)-1-methyl-pyrrolidin-3-ylmethoxy)-pyridine

    [0966] Starting from the compound of Preparation BB2 (200 mg) and (R)-(1-methyl-pyrrolidin-3-yl)-methanol (104 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a colourless oil (120 mg; 43% yield).

    [0967] MS3 (ESI, m/z): 341.04 [M+H.sup.+]; t.sub.R=0.63 min.

    C40.ii. 3-[6-((R)-1-methyl-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]benzaldehyde

    [0968] Starting from intermediate C40.i (110 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless oil (82 mg; 85% yield).

    [0969] MS3 (ESI, m/z): 297.02 [M+H.sup.+]; t.sub.R=0.62 min.

    Preparation C41: 3-[6-((S)-1-methyl-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    C41.i. 2-(3-[1,3]dioxolan-2-yl-phenyl)-6-((S)-1-methyl-pyrrolidin-3-ylmethoxy)-pyridine

    [0970] Starting from the compound of Preparation BB2 (200 mg) and (S)-(1-methyl-pyrrolidin-3-yl)-methanol (109 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a colourless oil (180 mg; 64% yield).

    [0971] MS3 (ESI, m/z): 341.07 [M+H.sup.+]; t.sub.R=0.64 min.

    C41.ii. 3-[6-((S)-1-methyl-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]benzaldehyde

    [0972] Starting from intermediate C41.i (177 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless oil (133 mg; 86% yield).

    [0973] MS3 (ESI, m/z): 297.03 [M+H.sup.+]; t.sub.R=0.63 min.

    Preparation C42: rac-3-[6-(1-methyl-piperidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C42.i. Rac-2-(3-[1,3]dioxolan-2-yl-phenyl)-6-(1-methyl-piperidin-3-yloxy)-pyridine

    [0974] Starting from the compound of Preparation BB2 (200 mg) and N-methyl-3-piperidinol (0.106 mL; 98% purity; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as a yellow oil (51 mg; 18% yield).

    [0975] MS3 (ESI, m/z): 341.06 [M+H.sup.+]; t.sub.R=0.64 min.

    C42.ii. Rac-3-[6-(1-methyl-piperidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [0976] Starting from intermediate C42.i (45 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless oil (33 mg; 84% yield).

    [0977] MS3 (ESI, m/z): 297.03 [M+H.sup.+]; t.sub.R=0.62 min.

    Preparation C43: (R)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    C43. i. (R)-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0978] Starting from the compound of Preparation BB2 (200 mg) and (R)-3-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (188 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained after purification by CC (Combiflash; Hept/EA 1:0 to 0:1) as a colourless oil (408 mg; quant.).

    [0979] MS3 (ESI, m/z): 427.12 [M+H.sup.+]; t.sub.R=1.00 min.

    C43. ii. (R)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0980] Starting from intermediate C43.i (384 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow oil (348 mg; quant.).

    [0981] MS3 (ESI, m/z): 383.06 [M+H.sup.+]; t.sub.R=1.01 min.

    Preparation C44:(S)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    C44.i. (S)-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0982] Starting from the compound of Preparation BB2 (200 mg) and (S)-3-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (188 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained after purification by CC (Combiflash; Hept/EA 1:0 to 0:1) as a colourless oil (426 mg; quant.).

    [0983] MS3 (ESI, m/z): 427.11 [M+H.sup.+]; t.sub.R=1.00 min.

    C44.ii. (S)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [0984] Starting from intermediate C44.i (423 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow oil (348 mg; quant.).

    [0985] MS3 (ESI, m/z): 383.04 [M+H.sup.+]; t.sub.R=1.00 min.

    Preparation C45: 6-[64(S)-1-methyl-pyrrolidin-3-yloxy)-pyrazin-2-yl]-pyridine-2-carbaldehyde

    C45.i. 2-bromo-6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrazine

    [0986] Starting from 6-bromopyrazin-2-ol (1.5 g; commercial) and (R)-(−)-1-methyl-3-pyrrolidinol (1.02 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as a yellowish liquid (1.26 g; 57% yield).

    [0987] MS3 (ESI, m/z): 259.95 [M+H.sup.+]; t.sub.R=0.44 min.

    C45.ii. 2-((S)-1-methyl-pyrrolidin-3-yloxy)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazine

    [0988] Starting from intermediate C45.i (1.22 g) and proceeding in analogy to Preparation C28, step C28.ii, the title compound was obtained as an orange solid (3.08 g; quant.).

    [0989] MS3 (ESI, m/z): 306.04 [M+H.sup.+]; t.sub.R=0.35 min.

    C45.iii. 6-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrazin-2-yl]-pyridine-2-carbaldehyde

    [0990] Starting from intermediate C45.ii (250 mg) and 6-bromo-2-pyridinecarboxaldehyde (74.2 mg; commercial) and proceeding in analogy to Preparation C28, step C28.iii, the title compound was obtained as a light orange solid (49 mg; 47% yield).

    [0991] MS3 (ESI, m/z): 285.01 [M+H.sup.+]; t.sub.R=0.53 min.

    Preparation C46: 5-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrazin-2-yl]-pyridine-3-carbaldehyde

    [0992] Starting from intermediate C45.ii (250 mg) and 4-bromopyridine-2-carbaldehyde (73.5 mg; commercial) and proceeding in analogy to Preparation C28, step C28.iii, the title compound was obtained as an orange oil (54 mg; 52% yield).

    [0993] MS3 (ESI, m/z): 285.00 [M+H.sup.+]; t.sub.R=0.50 min.

    Preparation C47: 2-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrazin-2-yl]-pyridine-4-carbaldehyde

    [0994] Starting from intermediate C45.ii (250 mg) and 2-bromo-4-formylpyridine (73.5 mg; commercial) and proceeding in analogy to Preparation C28, step C28.iii, the title compound was obtained as a light orange solid (53 mg; 51% yield).

    [0995] MS3 (ESI, m/z): 282.01 [M+H.sup.+]; t.sub.R=0.53 min.

    Preparation C48: 4-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrazin-2-yl]-pyridine-2-carbaldehyde

    [0996] Starting from intermediate C45.ii (250 mg) and 4-bromopyridine-2-carbaldehyde (73.5 mg; commercial) and proceeding in analogy to Preparation C28, step C28.iii, the title compound was obtained, after purification by CC (Combiflash, DCM to DCM/MeOH 9:1), as an orange oil (54 mg; 52% yield).

    [0997] MS3 (ESI, m/z): 285.00 [M+H.sup.+]; t.sub.R=0.50 min.

    Preparation C49: 3-[5-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzaldehyde

    C49.i. 3-(3-[1,3]dioxolan-2-yl-phenyl)-5-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridazine

    [0998] Starting from the compound of Preparation BB3 (90 mg) and (S)-(+)-1-methyl-3-pyrrolidinol (329 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as a light orange solid (142 mg; quant.).

    [0999] MS3 (ESI, m/z): 328.05 [M+H.sup.+]; t.sub.R=0.49 min.

    C49. ii. 3-[5-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzaldehyde

    [1000] Starting from intermediate C49.i (150 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a brown sticky oil (98 mg; 84% yield).

    [1001] MS3 (ESI, m/z): 284.19 [M+H.sup.+]; t.sub.R=0.47 min.

    Preparation C50: {2-[2-(3-formyl-phenyl)-pyridin-4-yloxy]-ethyl}-carbamic acid tert-butyl ester

    C50.i. [2-(2-chloro-pyridin-4-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [1002] Starting from 2-chloro-2-chloro-4-hydroxypyridine (250 mg; commercial) and N-(tert-butoxycarbonyl)ethanolamine (0.305 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:2), as a colourless oil (560 mg; quant.).

    [1003] MS3 (ESI, m/z): 272.98 [M+H.sup.+]; t.sub.R=0.78 min.

    C50.ii. {2-[2-(3-formyl-phenyl)-pyridin-4-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1004] Starting from intermediate C50.i (535 mg), 3-formylphenylboronic acid (309 mg; commercial), Pd(PPh.sub.3).sub.4 (113 mg) and 2M aq. Na.sub.2CO.sub.3 (0.98 mL) and proceeding in analogy to Preparation BB1, but using EtOH/water/toluene 2:1:1 as solvents, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:1), as a yellow oil (408 mg; 61% yield).

    [1005] MS3 (ESI, m/z): 342.90 [M+H.sup.+]; t.sub.R=0.63 min.

    Preparation C51: (2-{(2-tert-butoxycarbonylamino-ethyl)-[2-(3′-formyl-biphenyl-3-yloxy)-ethyl]-amino}-ethyl)-carbamic acid tert-butyl ester

    C51.i. (2-{(2-tert-butoxycarbonylamino-ethyl)-[2-(3′-[1,3]dioxolan-2-yl-biphenyl-3-yloxy)-ethyl]-amino}-ethyl)-carbamic acid tert-butyl ester

    [1006] Starting from intermediate C17.ii and di-tert-butyl (azanediylbis(ethane-2,1-diyl))dicarbamate (139 mg; commercial) and proceeding in analogy to Preparation C17, step C17.iii, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:2), as a colourless oil (56 mg; 21% yield).

    [1007] MS3 (ESI, m/z): 572.15 [M+H.sup.+]; t.sub.R=0.82 min.

    C51. ii. (2-{(2-tert-butoxycarbonylamino-ethyl)-[2-(3′-formyl-biphenyl-3-yloxy)-ethyl]-amino}-ethyl)-carbamic acid tert-butyl ester

    [1008] Starting from intermediate C51.i (100 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a colourless oil (21 mg; 46% yield).

    [1009] MS3 (ESI, m/z): 528.14 [M+H+]; t.sub.R=0.81 min.

    Preparation C52: (2-tert-butoxycarbonylamino-ethyl)-{2-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    C52.i. (2-tert-butoxycarbonylamino-ethyl)-(2-hydroxy-ethyl)-carbamic acid tert-butyl ester

    [1010] N-(2-Hydroxyethyl)ethylenediamine (2.06 g; commercial) and TEA (13.8 mL) were dissolved in EtOH (30 mL) and THF (30 mL), di-tert-butyl dicarbonate (10.8 g) was added and the mixture was stirred at rt for 1 day. TBME and 2M aq. HCl was added and the org. layer was washed with sat. aq. NaHCO.sub.3 and brine, dried over MgSO.sub.4 and concentrated under reduced pressure. The title compound was obtained as an off-white oil (6.98 g; quant.).

    [1011] MS3 (ESI, m/z): 305.01 [M+H.sup.+]; t.sub.R=0.73 min.

    C52. ii. (2-tert-butoxycarbonylamino-ethyl)-{2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1012] Starting from intermediate C52.i (332 mg) and the compound of Preparation BB2 (457 mg) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 0:1), as an off-white solid (1.1 g; quant.).

    [1013] MS3 (ESI, m/z): 530.03 [M+H.sup.+]; t.sub.R=1.02 min.

    C52. iii. (2-tert-butoxycarbonylamino-ethyl)-{2-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1014] Starting from intermediate C52.ii (341 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as an off-white solid (295 mg; 95% yield).

    [1015] MS3 (ESI, m/z): 486.12 [M+H+]; t.sub.R=1.02 min.

    Preparation C53: [2-(2′-formyl-[2,4′]bipyridinyl-4-yloxy)-ethyl]-carbamic acid tert-butyl ester

    C53.i. [2-(2-chloro-pyridin-4-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [1016] Starting from 2-chloro-4-hydroxypyridine (200 mg; commercial) and (Boc-amino)ethanolamine (0.263 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:1), as a colourless solid (471 mg; quant.).

    [1017] MS3 (ESI, m/z): 273.01 [M+H.sup.+]; t.sub.R=0.79 min.

    C53.ii. [2-(2′-formyl-[2,4′]bipyridinyl-4-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [1018] Starting from intermediate C53.i (200 mg) and the compound of Preparation BB9 (359 mg) and proceeding in analogy to Preparation BB3, the title compound was obtained as a yellow oil (26 mg; 10% yield).

    [1019] MS3 (ESI, m/z): 343.99 [M+H+]; t.sub.R=0.71 min.

    Preparation C54: {2-[6-(2-formyl-pyridin-4-yl)-pyrazin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    C54.i. [2-(6-bromo-pyrazin-2-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [1020] Starting from 6-bromopyrazin-2-ol (250 mg, commercial) and (Boc-amino)ethanolamine (0.243 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:1), as a colourless solid (348 mg; 77% yield).

    [1021] MS3 (ESI, m/z): 319.92 [M+H.sup.+]; t.sub.R=0.84 min.

    C54. ii. {2-[6-(2-formyl-pyridin-4-yl)-pyrazin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1022] Starting from intermediate C54.i (120 mg) and the compound of Preparation BB9 (185 mg) and proceeding in analogy to Preparation BB1, the title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 1:2), as a red foam (68 mg; 52% yield).

    [1023] MS3 (ESI, m/z): 345.00 [M+H.sup.+]; t.sub.R=0.82 min.

    Preparation C55: [2-(2′-formyl-[3,4′]bipyridinyl-5-yloxy)-ethyl]-carbamic acid tert-butyl ester

    C55. i. [2-(5-bromo-pyridin-3-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [1024] Starting from 3-brom o-5-hydroxypyri dine (250 mg; commercial) and (Boc-amino)ethanolamine (0.245 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained after purification by CC (Combiflash; Hept to Hept/EA 1:1) as a colourless solid (512 mg; quant.).

    [1025] MS3 (ESI, m/z): 316.92 [M+H.sup.+]; t.sub.R=0.82 min.

    C55.ii. [2-(2′-formyl-[3,4′]bipyridinyl-5-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [1026] Starting from intermediate C55.i (200 mg) and the compound of Preparation BB9 (257 mg) and proceeding in analogy to Preparation BB1, the title compound was obtained, after purification by CC (Combiflash; DCM/MeOH 1:0 to 19:1), as a brown oil (97 mg; 45% yield).

    [1027] MS3 (ESI, m/z): 344.02 [M+H.sup.+]; t.sub.R=0.74 min.

    Preparation C56: {2-[4-(3-formyl-phenyl)-pyrimidin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    C56. i. 2-chloro-4-(3-[1,3]dioxolan-2-yl-phenyl)-pyrimidine

    [1028] 3-(1,3-dioxolan-2-yl)phenylboronic acid pinacol ester (200 mg; commercial), 2,4-dichloropyrimidine (122 mg; commercial) and Na.sub.2CO.sub.3 (230 mg) were suspended with a mixture of dioxane/water 1:1 (3.6 mL). Pd(PPh.sub.3).sub.4 (83.7 mg) was added and the mixture was degassed with N.sub.2 and stirred in the microwave at 100° C. for 20 min. The mixture was partitioned between EA and water, the aq. layer was extracted with EA and the combined org. layers were washed with brine, dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The title compound was obtained, after purification by CC (Combiflash; Hept/EA 1:0 to 1:1), as a colourless oil (85 mg; 45% yield).

    [1029] MS3 (ESI, m/z): 262.99 [M+H.sup.+]; t.sub.R=0.80 min.

    C56. ii. 2-[4-(3-[1,3]dioxolan-2-yl-phenyl)-pyrimidin-2-yloxy]-ethylamine

    [1030] To a solution of intermediate C56.i (70 mg) and (Boc-amino)ethanolamine (0.084 mL; commercial) in DMF (1.2 mL) at 0° C. was added NaH (32 mg) and the mixture was stirred at rt for 1 day. The title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow oil (49 mg; 64% yield).

    [1031] MS3 (ESI, m/z): 288.00 [M+H.sup.+]; t.sub.R=0.54 min.

    C56. iii. {2-[4-(3-[1,3]dioxolan-2-yl-phenyl)-pyrimidin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1032] Intermediate C56.ii (46 mg) and TEA (0.056 mL) were dissolved in water/dioxane 1:3.5 (0.9 mL). Di-tert-butyl dicarbonate (42 mg) was added and the mixture was stirred at rt for 1 day. EA was added and the mixture was washed with water. The aq. layer was extracted with EA. The combined org. layers were dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The title compound was obtained as a yellowish oil (62 mg; quant.).

    [1033] MS3 (ESI, m/z): 388.04 [M+H.sup.+]; t.sub.R=0.85 min.

    C56. iv. {2-[4-(3-formyl-phenyl)-pyrimidin-2-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1034] Starting from intermediate C56.iii (60 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow oil (53 mg; quant.).

    [1035] MS3 (ESI, m/z): 344.02 [M+H+]; t.sub.R=0.84 min.

    Preparation C57: {2-[2-(3-formyl-phenyl)-6-methoxy-pyridin-4-yloxy]-ethyl}-carbamic acid tert-butyl ester

    C57.i. 2-bromo-6-methoxy-pyridin-4-ol

    [1036] Starting from 2-bromo-6-methoxy-pyridine (0.163 mL; commercial) and proceeding in analogy to Preparation C36, step C36.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 3:1), as a colourless solid (153 mg; 58% yield).

    [1037] MS3 (ESI, m/z): 203.97 [M+H.sup.+]; t.sub.R=0.67 min.

    C57.ii. [2-(2-bromo-6-methoxy-pyridin-4-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [1038] Starting from intermediate C57.i (100 mg) and N-(Boc)-ethanolamine (0.077 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless oil (144 mg; 85% yield).

    [1039] MS3 (ESI, m/z): 346.94 [M+H.sup.+]; t.sub.R=0.89 min.

    C57.iii. {2-[2-(3-formyl-phenyl)-6-methoxy-pyridin-4-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1040] Starting from intermediate C57.ii (70 mg) and 3-formylphenylboronic acid (33 mg; commercial) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in the microwave at 110° C. for 45 min, the title compound was obtained as a yellow foam (68 mg; 91% yield).

    [1041] MS3 (ESI, m/z): 373.02 [M+H.sup.+]; t.sub.R=0.93 min.

    Preparation C58: [2-(2′-formyl-6-methoxy-[2,4′]bipyridinyl-4-yloxy)-ethyl]-carbamic acid tert-butyl ester

    [1042] Starting from intermediate C57.ii (70 mg) and the compound of Preparation BB9 (99 mg; commercial) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in the microwave at 110° C. for 45 min, the title compound was obtained as a yellowish solid (35 mg; 46% yield).

    [1043] MS3 (ESI, m/z): 374.00 [M+H.sup.+]; t.sub.R=0.91 min.

    Preparation C59: {2-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

    C59.i. {2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

    [1044] Starting from the compound of Preparation BB2 (100 mg) and N-Boc-N-methyl-aminoethanol (76 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 0:1), as a colourless solid (227 mg; quant.).

    [1045] MS3 (ESI, m/z): 400.99 [M+H.sup.+]; t.sub.R=0.97 min.

    C59. ii. {2-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

    [1046] Starting from intermediate C59.i (220 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow oil (201 mg; quant.).

    [1047] MS3 (ESI, m/z): 357.03 [M+H.sup.+]; t.sub.R=0.97 min.

    Preparation C60: {2-[6-(3-formyl-phenyl)-pyrazin-2-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

    C60. i. {2-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyrazin-2-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

    [1048] Starting from the compound of Preparation BB5 (100 mg) and N-Boc-N-methyl-aminoethanol (76 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 0:1), as a colourless oil (123 mg; 75% yield).

    [1049] MS3 (ESI, m/z): 401.88 [M+H.sup.+]; t.sub.R=0.94 min.

    C60. ii. {2-[6-(3-formyl-phenyl)-pyrazin-2-yloxy]-ethyl}-methyl-carbamic acid tert-butyl ester

    [1050] Starting from intermediate C60.i (110 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow oil (101 mg; quant.).

    [1051] MS3 (ESI, m/z): 358.02 [M+H.sup.+]; t.sub.R=0.93 min.

    Preparation C61: (2-{6-[2-(formyl)-pyrimidin-4-yl]-pyridin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester:

    C61.i. (E)-2-styrylpyrimidin-4-ol

    [1052] A solution of cinnamyl amidine hydrochloride (9.9 g; commercial) and sodium 3-ethoxy-3-oxoprop-1-en-1-olate (20.1 g, commercial) in water (300 mL) was stirred at rt for 2 days. The mixture was concentrated under reduced pressure to 1/3 of the original volume and acidified to pH 3 with 1N aq. HCl. The formed yellow precipitate was collected by vacuum filtration, washed with water, ether and dried under vacuum (oil pump). The title compound (7.87 g; 73% yield) was obtained as a light yellow solid.

    C61. ii. (E)-4-chloro-2-styrylpyrimidine

    [1053] A solution of intermediate C61.i (7.860 g) in phosphorus oxychloride (110 mL) was stirred for 3 h at 100° C. The reaction mixture was then cooled and concentrated under reduced pressure. The yellow residue was cautiously poured into ice/water and stirred for 30 min. A yellow oily precipitate was extracted several times with EA, the org. layers were combined, washed with water and brine, dried over Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The residue was washed with cold water, then Hex and dried on oil pump. The title compound was obtained as a light yellow solid (5.882 g; 68% yield).

    C61. iii. (E)-4-chloro-2-styrylpyrimidine

    [1054] To a solution of intermediate C61.ii (1.00 g) in dioxane (12.0 mL) under Ar was added Pd(PPh.sub.3).sub.4 (0.096 g). After 5 min, bis(tri-butyltin) (2.700 g) was added portionwise: first 1.34 mL and then, after heating the mixture for 2 h at 100° C., another 1.0 mL dropwise. The reaction mixture was stirred under Ar at 100° C. for 36 h. The mixture was allowed to cool to rt, filtered over Celite and washed with EA .The solution was washed with brine, dried over Na.sub.2SO.sub.4 and evaporated. To the residue was added ether and the precipitate was filtered off. The ether filtrate was evaporated and the residue was purified by prep-HPLC to give the title compound (0.242 g; 11% yield).

    C61.iv. (2-{6-[2-((E)-styryl)-pyrimidin-4-yl]-pyridin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1055] A glass microwave reaction vessel was charged with intermediate C61.iii (64 mg) and the compound of Preparation BB10 (52 mg) in DMF (2 mL). Ar was bubbled through for 45 min. Tetrakis(triphenylphosphine)palladium (12 mg) and LiCl (anhydrous; 14 mg) were added and the reaction mixture was stirred at 115° C. for 1 day. The mixture was cooled to rt. DMF was evaporated, DCM was added and the mixture was filtered over Celite, washed with 10% MeOH in DCM, and the filtrate was concentrated under reduced pressure. The titled compound was obtained, after purification by CC (EA/Hex 1/7, then 1/4), as a colourless oil (34 mg; 61% yield).

    [1056] .sup.1H NMR (300 MHz, CDCl.sub.3) δ: 8.82 (d, J=5.1 Hz, 1H); 8.25 (d, J=7.2 Hz, 1H); 8.11-8.06 (m, 2H); 7.79 (t, J=7.8 Hz, 1H); 7.67 (d, J=6.9 Hz, 2H); 7.44-7.30 (m, 4H); 6.89 (d, J=8.4 Hz, 1H); 4.53-4.05 (m, 2H); 3.63-3.58 (m, 2H); 1.45 (s, 9H).

    [1057] MS4 (ESI, m/z): 419 [M+H.sup.−]; t.sub.R=7.55 min.

    C61.v. (2-{6-[2-(formyl)-pyrimidin-4-yl]-pyridin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1058] Intermediate C61.iv (35 mg) was dissolved in MeOH/DCM-1:1 (6 mL) and NaHCO.sub.3 (32 mg) was added. The reaction mixture was cooled to −78° C. Ozone was passed through for 3 min until a blue solution was produced. Argon was then passed through at −78° C. for 10 min, then Me.sub.2S (0.02 mL) was added at −78° C. The reaction mixture was warmed to rt, the solvent was evaporated, DCM was added, NaHCO.sub.3 was filtered off and the solvent was evaporated. The product was used in the next step without further purification.

    [1059] MS4 (ESI, m/z): 345 [M+H.sup.−]; t.sub.R=2.45 min.

    Preparation C62: 3-[5-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzaldehyde

    C62. i. 3-(3-[1,3]dioxolan-2-yl-phenyl)-5-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridazine

    [1060] Starting from the compound of Preparation BB3 (97 mg) and (R)-(−)-1-methyl-3-pyrrolidinol (322 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as a red oil (199 mg; quant.).

    [1061] MS1 (ESI, m/z): 328.10 [M+H.sup.+]; t.sub.R=0.49 min.

    C62.ii. 3-[5-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzaldehyde

    [1062] Starting from intermediate C62.i (150 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light brown sticky oil (107 mg; 92% yield).

    [1063] MS1 (ESI, m/z): 284.19 [M+H.sup.+]; t.sub.R=0.48 min.

    Preparation C63: 3-[6-methoxy-4-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C63. i. 2-bromo-6-methoxy-4-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridine

    [1064] Starting from intermediate C57.i (220 mg) and (R)-(−)-1-methyl-3-pyrrolidinol (0.13 mL; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as a yellow oil (217 mg; 70% yield).

    [1065] MS3 (ESI, m/z): 288.91 [M+H.sup.+]; t.sub.R=0.53 min.

    C63.ii. 3-[6-methoxy-4-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [1066] Starting from intermediate C63.i (40 mg) and 3-formylphenylboronic acid (22 mg; commercial) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in the microwave at 110° C. for 45 min, the title compound was obtained as an orange oil (34 mg; 78% yield).

    [1067] MS3 (ESI, m/z): 313.02 [M+H.sup.+]; t.sub.R=0.63 min.

    Preparation C64: 3-[6-((R)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    C64.i. 2-(3-[1,3]dioxolan-2-yl-phenyl)-6-((R)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine

    [1068] Starting from the compound of Preparation BB2 (200 mg) and (R)-1-methyl-2-pyrrolidinemethanol (95 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 19:1), as a light yellow oil (241 mg; 86% yield).

    [1069] MS3 (ESI, m/z): 341.05 [M+H.sup.+]; t.sub.R=0.65 min.

    C64.ii. 3-[6-((R)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzaldehyde

    [1070] Starting from intermediate C64.i (180 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow oil (180 mg; 96% yield). MS3 (ESI, m/z): 297.02 [M+H.sup.+]; t.sub.R=0.64 min.

    Preparation C65: rac-(2S*,3S*)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    C65.i. Rac-(2S*,3R*)-3-hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1071] Starting from trans-2-methylpyrrolidin-3-ol HCl (400 mg; commercial) and proceeding in analogy to Preparation C56, step C56.iii, the title compound was obtained as a light yellow oil (552 mg; 99% yield).

    [1072] MS3 (ESI, m/z): 202.15 [M+H.sup.+]; t.sub.R=0.64 min.

    C65.ii. Rac-(2S*,3S*)-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1073] Starting from the compound of Preparation BB2 (200 mg) and intermediate C65.i (182 mg) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:4), as a colourless oil (371 mg; quant.).

    [1074] MS3 (ESI, m/z): 427.10 [M+H.sup.+]; t.sub.R=1.00 min.

    C65.iii. Rac-(2S*,3S*)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1075] Starting from intermediate C65.ii (350 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow oil (247 mg; quant.).

    [1076] MS3 (ESI, m/z): 383.04 [M+H.sup.+]; t.sub.R=1.01 min.

    Preparation C66: rac-(3S*,4R*)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    C66.i. Rac-(3R*,4R*)-3-hydroxy-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1077] Starting from cis-4-methylpyrrolidin-3-ol hydrochloride (400 mg; commercial) and proceeding in analogy to Preparation C56, step C56.iii., the title compound was obtained as a light yellow oil (561 mg; quant.).

    [1078] MS3 (ESI, m/z): 202.14 [M+H.sup.+]; t.sub.R=0.65 min.

    C66. ii. Rac-(3S*,4R*)-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridin-2-yloxy]-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1079] Starting from the compound of Preparation BB2 (200 mg) and intermediate C66.i (200 mg) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:4), as a yellowish oil (327 mg; 93% yield).

    [1080] MS3 (ESI, m/z): 427.11 [M+H.sup.+]; t.sub.R=1.01 min.

    C66. iii. Rac-(3S*,4R*)-3-[6-(3-formyl-phenyl)-pyridin-2-yloxy]-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1081] Starting from intermediate C66.ii (300 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as an orange oil (261 mg; quant.).

    [1082] MS3 (ESI, m/z): 383.03 [M+H.sup.+]; t.sub.R=1.02 min.

    Preparation C67: 3-[5-(1-methyl-azetidin-3-yloxy)-pyridazin-3-yl]-benzaldehyde

    C67.i. 3-(3-[1,3]dioxolan-2-yl-phenyl)-5-(1-methyl-azetidin-3-yloxy)-pyridazine

    [1083] Starting from a compound of Preparation BB3. (108 mg) and 1-methyl-azetidin-3-ol (269 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as an orange sticky oil (166 mg; quant.).

    [1084] MS1 (ESI, m/z): 314.08 [M+H.sup.+]; t.sub.R=0.49 min.

    C67. ii. 3-[5-(1-methyl-azetidin-3-yloxy)-pyridazin-3-yl]-benzaldehyde

    [1085] Starting from intermediate C67.i (129 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light brown sticky oil (117 mg; quant.).

    [1086] MS1 (ESI, m/z): 270.19 [M+H.sup.+]; t.sub.R=0.46 min.

    Preparation C68: 3-[6-((3S,5S)-1,5-dimethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C68.i. (2S,4S)-4-(6-bromo-pyridin-2-yloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1087] Starting from 6-bromopyridin-2-ol (150 mg) and (2S,4R)-4-hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (165 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:4), as a yellowish oil (238 mg; 81% yield).

    [1088] MS3 (ESI, m/z): 356.89 [M+H.sup.+]; t.sub.R=0.98 min.

    C68.ii. 2-bromo-6-((3S,5S)-5-methyl-pyrrolidin-3-yloxy)-pyridine

    [1089] Starting from intermediate C68.i (210 mg) and proceeding in analogy to Preparation C13, step C13.ii, the title compound was obtained without further purification as a yellow oil (146 mg; 97% yield).

    [1090] MS3 (ESI, m/z): 259.90 [M+H.sup.+]; t.sub.R=0.55 min.

    [1091] C68. iii. 2-bromo-6-((3S,5S)-1,5-dimethyl-pyrrolidin-3-yloxy)-pyridine

    [1092] Starting from intermediate C68.ii (130 mg) and 37% aq. formaldehyde (0.513 mL) and proceeding in analogy to Preparation C13, step C13.iii, the title compound was obtained as a yellow oil (123 mg; 90% yield).

    [1093] MS3 (ESI, m/z): 270.93 [M+H+]; t.sub.R=0.55 min.

    [1094] C68. iv. 3-[6-((3S,5S)-1,5-dimethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [1095] Starting from intermediate C68.iii (115 mg) and 3-formylphenylboronic acid (68 mg; commercial) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in the microwave at 110° C. for 45 min, the title compound was obtained as a brown oil (121 mg; 96% yield).

    [1096] MS3 (ESI, m/z): 297.05 [M+H.sup.+]; t.sub.R=0.65 min.

    Preparation C69: rac-3-[6-((2S*,3S*)-1,2-dimethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [1097] C69.i. Rac-(2S*,3S*)-3-(6-Bromo-pyridin-2-yloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1098] Starting from 6-bromopyridin-2-ol (150 mg) and intermediate C65.i (165 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as a yellowish oil (165 mg; 56% yield).

    [1099] MS3 (ESI, m/z): 356.89 [M+H.sup.+]; t.sub.R=0.97 min.

    C69.ii. Rac-2-bromo-6-((2S*,3S*)-2-methyl-pyrrolidin-3-yloxy)-pyridine

    [1100] Starting from intermediate C69.i (150 mg) and proceeding in analogy to Preparation C13, step C13.ii, the title compound was obtained without further purification as a yellow oil (101 mg; 94% yield).

    [1101] MS3 (ESI, m/z): 258.90 [M+H.sup.+]; t.sub.R=0.56 min.

    C69.iii. Rac-2-bromo-6-((2S*,3S*)-1,2-dimethyl-pyrrolidin-3-yloxy)-pyridine

    [1102] Starting from intermediate C69.ii (90 mg) and 37% aq. formaldehyde (0.355 mL) and proceeding in analogy to Preparation C13, step C13.iii, the title compound was obtained as a yellow oil (70 mg; 74% yield).

    [1103] MS3 (ESI, m/z): 270.93 [M+H+]; t.sub.R=0.56 min.

    C69. iv. Rac-3-[6-((2S*,3S*)-1,2-dimethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [1104] Starting from intermediate C69.iii (64 mg) and 3-formylphenylboronic acid (38 mg; commercial) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in the microwave at 110° C. for 45 min, the title compound was obtained as a brown oil (69 mg; 99% yield).

    [1105] MS3 (ESI, m/z): 297.03 [M+H.sup.+]; t.sub.R=0.65 min.

    Preparation C70: rac-3-[6-((3S*,4R*)-1,4-dimethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C70.i. Rac-(3S*,4R*)-3-(6-bromo-pyridin-2-yloxy)-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1106] Starting from 6-bromopyridin-2-ol (150 mg) and intermediate C66.i (165 mg; commercial) and proceeding in analogy to Preparation C2, step C2.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as a yellowish oil (139 mg; 48% yield).

    [1107] MS3 (ESI, m/z): 356.89 [M+H.sup.+]; t.sub.R=0.98 min.

    C70.ii. Rac-2-bromo-6-((3S*,4R*)-4-methyl-pyrrolidin-3-yloxy)-pyridine

    [1108] Starting from intermediate C70.i (120 mg) and proceeding in analogy to Preparation C13, step C13.ii, the title compound was obtained without further purification as a yellow oil (81 mg; 94% yield).

    [1109] MS3 (ESI, m/z): 258.92 [M+H.sup.+]; t.sub.R=0.56 min.

    C70.iii. Rac-2-bromo-6-((3S*,4R*)-1,4-dimethyl-pyrrolidin-3-yloxy)-pyridine

    [1110] Starting from intermediate C70.ii (70 mg) and 37% aq. formaldehyde (0.276 mL) and proceeding in analogy to Preparation C13, step C13.iii, the title compound was obtained as a yellow oil (71 mg; 96% yield).

    [1111] MS3 (ESI, m/z): 270.93 [M+H+]; t.sub.R=0.58 min.

    C70. iv. Rac-3-[6-((3S*,4R*)-1,4-dimethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [1112] Starting from intermediate C70.iii (63 mg) and 3-formylphenylboronic acid (37 mg; commercial) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in the microwave at 110° C. for 45 min, the title compound was obtained as a brown oil (54 mg; 78% yield).

    [1113] MS3 (ESI, m/z): 297.05 [M+H.sup.+]; t.sub.R=0.66 min.

    Preparation C71: (RS)-3-[6-((RS)-1,2-dimethyl-azetidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    C71.i. (RS)-2-((RS)-1,2-dimethyl-azetidin-3-yloxy)-6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridine

    [1114] To a suspension of LiAlH.sub.4 (47.4 mg) in THF (0.5 mL) was added a solution of intermediate C35.i (100 mg) in THF (0.8 mL) and the resulting mixture was stirred at 65° C. for 1 h. After cooling to rt, water (0.25 mL), 2M aq. NaOH (0.250 mL), and water (0.750 mL) were added sequentially. The mixture was stirred at rt for 1 h and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to give the title compound as a light yellow oil (54 mg; 85% yield).

    [1115] MS3 (ESI, m/z): 327.02 [M+H.sup.+]; t.sub.R=0.64 min.

    C71.ii. (RS)-3-[6-((RS)-1,2-dimethyl-azetidin-3-yloxy)-pyridin-2-yl]-benzaldehyde

    [1116] Starting from intermediate C71.i (47 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow oil (34 mg; 84% yield).

    [1117] MS1 (ESI, m/z): 283.02 [M+H.sup.+]; t.sub.R=0.63 min.

    Preparation C72: 6-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridine-2-carbaldehyde

    C72. i. 2-chloro-6-(6-[1,3]dioxolan-2-yl-pyridin-2-yl)-pyrazine

    [1118] To a mixture of 2-bromo-6-chloropyrazine (100 mg) and the compound of Preparation BB11 (113 mg) in dioxane (1.2 mL) was added a solution of K.sub.2CO.sub.3 (143 mg) in water (0.4 mL). The resulting suspension was degassed with N.sub.2 for 10 min, tris(dibenzylideneacetone)-dipalladium(0) (23.7 mg) and PCy3 (17.4 mg) were added, the reaction flask was sealed and heated at 85° C. for 1 day. Water and EA were added, the layers were separated and the aq. layer was extracted twice with EA. The combined org. extracts were dried (MgSO.sub.4), filtered and concentrated under reduced pressure. The title compound was obtained, after purification by CC (Combiflash; Hept to Hept/EA 1:1), as a yellowish oil (29 mg, 21% yield).

    [1119] MS3 (ESI, m/z): 263.97 [M+H.sup.+]; t.sub.R=0.79 min.

    C72.ii. 2-(6-[1,3]dioxolan-2-yl-pyridin-2-yl)-6-(1-methyl-azetidin-3-yloxy)-pyrazine

    [1120] Starting from intermediate C72.i (25 mg) and 1-methyl-azetidin-3-ol (65 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as a yellow oil (28 mg; 94% yield).

    [1121] MS1 (ESI, m/z): 315.01 [M+H.sup.+]; t.sub.R=0.51 min.

    C72. iii. 6-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridine-2-carbaldehyde

    [1122] Starting from intermediate C72.ii (23 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow solid (17 mg; 86% yield).

    [1123] MS1 (ESI, m/z): 271.00 [M+H.sup.+]; t.sub.R=0.51 min.

    Preparation C73: tert-butyl (R)-3-((6-(3-formylphenyl)pyridazin-4-yl)oxy)pyrrolidine-1-carboxylate

    C73.i. (R)-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridazin-4-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1124] Starting from the compound of Preparation BB3 (108 mg) and (R)-N-Boc-3-pyrrolidinol (360 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as a yellow sticky oil (463 mg; quant.).

    [1125] MS1 (ESI, m/z): 414.19 [M+H.sup.+]; t.sub.R=0.84 min.

    C73.ii. Tert-butyl (R)-3-((6-(3-formylphenyl)pyridazin-4-yl)oxy)pyrrolidine-1-carboxylate

    [1126] Starting from intermediate C73.i (170 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow solid (386 mg; quant.).

    [1127] MS1 (ESI, m/z): 370.04 [M+H.sup.+]; t.sub.R=0.86 min.

    Preparation C74: (S)-3-[6-(3-formyl-phenyl)-pyridazin-4-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    C74.i. (S)-3-[6-(3-[1,3]dioxolan-2-yl-phenyl)-pyridazin-4-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1128] Starting from compound of Preparation BB3 (108 mg) and (S)—N-Boc-3-pyrrolidinol (360 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as an orange sticky oil (410 mg; quant.).

    [1129] MS1 (ESI, m/z): 414.18 [M+H.sup.+]; t.sub.R=0.84 min.

    C74.i. (S)-3-[6-(3-formyl-phenyl)-pyridazin-4-yloxy]-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1130] Starting from intermediate C74.i (170 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow sticky oil (363 mg; quant.).

    [1131] MS1 (ESI, m/z): 370.03 [M+H.sup.+]; t.sub.R=0.86 min.

    Preparation C75: tert-butyl (S)-2-(((6-(3-formylphenyl)pyridazin-4-yl)oxy)methyl)azetidine-1-carboxylate

    C75. i. Tert-butyl (S)-2-(((6-(3-(1,3-dioxolan-2-yl)phenyl)pyridazin-4-yl)oxy)methyl)azetidine-1-carboxylate

    [1132] Starting from compound of Preparation BB3 (108 mg) and (S)-1-(tert-butoxycarbonyl)-2-azetidinemethanol (379 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as an orange sticky oil (297 mg; quant.).

    [1133] MS1 (ESI, m/z): 414.19 [M+H.sup.+]; t.sub.R=0.82 min.

    C75.i. Tert-butyl (S)-2-(((6-(3-formylphenyl)pyridazin-4-yl)oxy)methyl)azetidine-1-carboxylate

    [1134] Starting from intermediate C75.i (170 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow sticky oil (258 mg; quant.).

    [1135] MS1 (ESI, m/z): 370.06 [M+H.sup.+]; t.sub.R=0.84 min.

    Preparation C76: 6′-(1-methyl-azetidin-3-yloxy)-[2,2′]bipyridinyl-4-carbaldehyde

    C76.i. 6′-chloro-4-dimethoxymethyl-[2,2′]bipyridinyl

    [1136] Starting from 2-bromo-6-chloropyridine (200 mg) and [4-(dimethoxymethyl)pyridin-2-yl]boronic acid (237 mg; commercial) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in a microwave oven at 110° C. for 45 min, the title compound was obtained as a colourless oil (56 mg; 20% yield).

    [1137] MS3 (ESI, m/z): 264.98 [M+H.sup.+]; t.sub.R=0.81 min.

    C76.ii. 4-dimethoxymethyl-6′-(1-methyl-azetidin-3-yloxy)-[2,2′]bipyridinyl

    [1138] Starting from intermediate C76.i (25 mg) and 1-methyl-azetidin-3-ol (43 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as a yellow oil (29 mg; 97% yield).

    [1139] MS3 (ESI, m/z): 316.05 [M+H.sup.+]; t.sub.R=0.52 min.

    C76.iii. 6′-(1-methyl-azetidin-3-yloxy)-[2,2′]bipyridinyl-4-carbaldehyde

    [1140] Starting from intermediate C76.ii (33 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellowish oil (25 mg; quant.).

    [1141] MS3 (ESI, m/z): 270.01 [M+H.sup.+]; t.sub.R=0.55 min.

    Preparation C77: 6-(1-methyl-azetidin-3-yloxy)-[2,4]bipyridinyl-2′-carbaldehyde

    C77.i. 6-chloro-[2,4′]bipyridinyl-2′-carbaldehyde

    [1142] Starting from 2-bromo-6-chloropyridine (150 mg) and the compound of Preparation BB9 (322 mg) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in a microwave oven at 110° C. for 45 min, the title compound was obtained as an off-white solid (99 mg; 58% yield).

    [1143] MS3 (ESI, m/z): 219.03 [M+H.sup.+]; t.sub.R=0.78 min.

    C77.ii. 6-chloro-2′-[1,3]dioxolan-2-yl-[2,4′]bipyridinyl

    [1144] Starting from intermediate C77.i (85 mg) and ethylene glycol (0.044 mL; commercial) and proceeding in analogy to Preparation BB11, step BB11.i, the title compound was obtained as an orange oil (102 mg; quant.).

    [1145] MS3 (ESI, m/z): 262.99 [M+H.sup.+]; t.sub.R=0.70 min.

    C77.iii. 2′-[1,3]dioxolan-2-yl-6-(1-methyl-azetidin-3-yloxy)-[2,4′]bipyridinyl

    [1146] Starting from 1-methyl-azetidin-3-ol (123 mg) and intermediate C77.ii (95 mg) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as a yellow oil (107 mg; quant.).

    [1147] MS3 (ESI, m/z): 314.03 [M+H.sup.+]; t.sub.R=0.48 min.

    C77.iv. 6-(1-methyl-azetidin-3-yloxy)-[2,4′]bipyridinyl-2′-carbaldehyde

    [1148] Starting from intermediate C77.iii (103 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow oil (66 mg; quant.).

    [1149] MS3 (ESI, m/z): 270.01 [M+H.sup.+]; t.sub.R=0.53 min.

    Preparation C78: 4-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridine-2-carbaldehyde

    C78. i. 4-(6-chloro-pyrazin-2-yl)-pyridine-2-carbaldehyde

    [1150] Starting from 2-bromo-6-chloropyrazine (100 mg) and the compound of Preparation BB9 (214 mg) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in a microwave oven at 110° C. for 45 min, the title compound was obtained as a light yellow solid (51 mg; 45% yield).

    [1151] MS3 (ESI, m/z): 220.01 [M+H.sup.+]; t.sub.R=0.72 min.

    C78. ii. 2-chloro-6-(2-[1,3]dioxolan-2-yl-pyridin-4-yl)-pyrazine

    [1152] Starting from intermediate C78.i (48 mg) and proceeding in analogy to Preparation BB11, step BB11.i, the title compound was obtained as an orange oil (49 mg; quant.).

    [1153] MS3 (ESI, m/z): 264.98 [M+H.sup.+]; t.sub.R=0.68 min.

    C78.iii. 2-(2-[1,3]dioxolan-2-yl-pyridin-4-yl)-6-(1-methyl-azetidin-3-yloxy)-pyrazine

    [1154] Starting from 1-methyl-azetidin-3-ol (47 mg) and intermediate C78.ii (45 mg) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as an orange oil (38 mg; quant.).

    [1155] MS3 (ESI, m/z): 315.01 [M+H.sup.+]; t.sub.R=0.46 min.

    C78.iv. 4-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridine-2-carbaldehyde

    [1156] Starting from intermediate C78.iii (35 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow oil (27 mg; quant.).

    [1157] MS3 (ESI, m/z): 271.01 [M+H.sup.+]; t.sub.R=0.47 min.

    Preparation C79: 6′-(1-methyl-azetidin-3-yloxy)-[2,2′]bipyridinyl-6-carbaldehyde

    C79.i. 6-chloro-6′-[1,3]dioxolan-2-yl-[2,2′]bipyridinyl

    [1158] Starting from 2-bromo-6-chloropyridine (200 mg) and the compound of Preparation BB11 (273 mg) and proceeding in analogy to Preparation C72, step C72.i, the titled compound was obtained as a light yellow solid (119 mg, 44% yield).

    [1159] MS3 (ESI, m/z): 262.97 [M+H.sup.+]; t.sub.R=0.83 min.

    C79.ii. 6′-[1,3]dioxolan-2-yl-6-(1-methyl-azetidin-3-yloxy)-[2,2′]bipyridinyl

    [1160] Starting from intermediate C79.i (105 mg) and 1-methyl-azetidin-3-ol (181 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as a light yellow oil (27 mg; 22% yield).

    [1161] MS3 (ESI, m/z): 314.03 [M+H.sup.+]; t.sub.R=0.57 min.

    C79.iii. 6′-(1-methyl-azetidin-3-yloxy)-[2,2′]bipyridinyl-6-carbaldehyde

    [1162] Starting from intermediate C79.ii (24 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a light yellow oil (19 mg; 92% yield).

    [1163] MS3 (ESI, m/z): 270.00 [M+H.sup.+]; t.sub.R=0.58 min.

    Preparation C80: 2-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridine-4-carbaldehyde

    C80.i. 2-chloro-6-(4-dimethoxymethyl-pyridin-2-yl)-pyrazine

    [1164] Starting from 2-bromo-6-chloropyrazine (200 mg; commercial) and [4-(dimethoxymethyl)pyridin-2-yl]boronic acid (229 mg; commercial) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in a microwave oven at 110° C. for 45 min, the title compound was obtained as a yellow solid (25 mg; 9% yield).

    [1165] MS3 (ESI, m/z): 265.96 [M+H.sup.+]; t.sub.R=0.82 min.

    C80.ii. 2-(4-dimethoxymethyl-pyridin-2-yl)-6-(1-methyl-azetidin-3-yloxy)-pyrazine

    [1166] Starting from intermediate C80.i (23 mg) and 1-methyl-azetidin-3-ol (15 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as a brown oil (19 mg; quant.).

    [1167] MS3 (ESI, m/z): 317.07 [M+H.sup.+]; t.sub.R=0.53 min.

    C80. iii. 2-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridine-4-carbaldehyde

    [1168] Starting from intermediate C80.ii (17 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a brown oil (14 mg; quant.).

    [1169] MS3 (ESI, m/z): 271.01 [M+H.sup.+]; t.sub.R=0.50 min.

    Preparation C81: 5-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridine-3-carbaldehyde

    C81.i. 2-chloro-6-(5-dimethoxymethyl-pyridin-3-yl)-pyrazine

    [1170] Starting from 2-bromo-6-chloropyrazine (200 mg) and 5-(dimethoxymethyl)pyridine-3-boronic acid (208 mg; commercial) and proceeding in analogy to Preparation BB1, irradiating however the reaction mixture in a microwave oven at 110° C. for 45 min, the title compound was obtained as a yellow solid (220 mg; 83% yield).

    [1171] MS3 (ESI, m/z): 265.96 [M+H.sup.+]; t.sub.R=0.71 min.

    C81.ii. 2-(5-dimethoxymethyl-pyridin-3-yl)-6-(1-methyl-azetidin-3-yloxy)-pyrazine

    [1172] Starting from intermediate C81.i (195 mg) and 1-methyl-azetidin-3-ol (200 mg; commercial) and proceeding in analogy to Preparation C14, step C14.i, the title compound was obtained as an orange oil (238 mg; quant.).

    [1173] MS3 (ESI, m/z): 317.04 [M+H.sup.+]; t.sub.R=0.48 min.

    C81.iii. 5-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridine-3-carbaldehyde

    [1174] Starting from intermediate C81.ii (212 mg) and proceeding in analogy to Preparation A7, step A7.ii, the title compound was obtained as a yellow solid (157 mg; 87% yield).

    [1175] MS3 (ESI, m/z): 271.02 [M+H.sup.+]; t.sub.R=0.47 min.

    Preparation D1: 6-[(S)-5-(2-amino-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    D1.i. 3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-propionic acid

    [1176] A solution of 3-[(S)-2-oxo-3-(3-oxo-3 ,4-dihydro-2H-pyri do [3 ,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-propionaldehyde (8.0 g; prepared according to WO 2010/041194) in water (46 mL) and acetone (240 mL) was treated with KMnO.sub.4 (9.8 g) and further stirred at rt for 2 h. The reaction mixture was treated with sodium bisulfite (9.0 g), further stirred for 15 min, filtered through a pad of Celite and the volatiles were removed under reduced pressure. The pH of the aq. layer was adjusted to 5 and the solid was collected by filtration. The crude product was dissolved with EA and extracted twice with 0.1M NaOH. The combined aq. layers were washed with EA, acidified (pH 3) with 1M HCl, the precipitate was filtered off, affording 4 g of title compound as a colourless solid. The aq. phase was extracted three times with DCM/MeOH. The combined org. layers were washed with brine, dried over MgSO.sub.4 and concentrated under reduced pressure, affording another 670 mg of title compound as a colourless solid (total: 4.67 g; 62% yield).

    [1177] MS4 (ESI, m/z): 507.9 [M+H.sup.+]; t.sub.R=0.58 min.

    D1.ii. {2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethyl}-carbamic acid benzyl ester

    [1178] A solution of intermediate D1.i (1.60 g), benzyl alcohol (5.39 mL) and TEA (3.8 mL) in DMF (4.8 mL) was heated to 100° C. and treated dropwise with DPPA (1.26 mL) and further stirred at 100° C. for 4 h. The reaction mixture was diluted with EA, sequentially washed with sat. aq. NH.sub.4Cl, sat. aq. NaHCO.sub.3 and brine, dried over MgSO.sub.4, filtered and concentrated to dryness. Water was added and the azeotrope was removed under reduced pressure. The crude product was purified by CC (EA/Hept 2:1), affording an off-white solid (0.8 g; 37% yield).

    [1179] MS1 (ESI, m/z): 413.4 [M+H.sup.+]; t.sub.R=0.78 min.

    D1.iii. 6-[(S)-5-(2-amino-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1180] A solution of intermediate D1.ii (750 mg) in MeOH (30 mL) was hydrogenated over Pd(OH).sub.2/C (121 mg) for 1 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure, affording an off-white foam (530 mg; 100% yield).

    [1181] MS1 (ESI, m/z): 279.32 [M+H.sup.+]; t.sub.R=0.45 min.

    Examples of Compounds Sccording to the Invention

    [1182] Example 1

    6-[(S)-5-(2-{[3′-(2-amino-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    1.i. {2-[3′-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-biphenyl-3-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1183] A solution of the compound of Preparation A1 (21.6 mg) and the compound of Preparation D1 (18.5 mg) in DMF/DCM (1:1; 7 mL) was treated with NaBH(OAc).sub.3 (40 mg) and further stirred at rt for 1 day. The residue was partioned between sat. aq. NaHCO.sub.3 and EA. The org. layer was separated, washed with brine dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC (method 1), affording a colourless lyophilisate (22 mg; 58% yield).

    [1184] MS1 (ESI, m/z): 604.16 [M+H.sup.+]; t.sub.R=0.76 min.

    1.ii. 6-[(S)-5-(2-{[3′-(2-amino-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1185] A solution of intermediate 1.i (10 mg) in DCM (0.05 mL) was treated with TFA (0.05 mL) and further stirred at rt for 1 h. The solution was concentrated to dryness and the residue was taken up in DCM and treated with NH.sub.4OH. The aq. layer was extracted twice with DCM. The combined org. layers were washed with brine and dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC (method 1), affording a colourless lyophilisate (5 mg; 66% yield).

    [1186] MS1 (ESI, m/z): 504.06 [M+H.sup.+]; t.sub.R=0.54 min.

    Example 2

    6-[(S)-5-(2-{[3′-(2-dimethylamino-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1187] Starting from the compound of Preparation A2 (40 mg) and the compound of Preparation D1 (44 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as an off-white lyophilisate (9 mg; 12% yield).

    [1188] MS3 (ESI, m/z): 532.12 [M+H.sup.+]; t.sub.R=0.54 min.

    Example 3

    6-[(S)-5-(2-{[3′-(3-amino-propoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    3.i. [3-(3′-[1,3]dioxolan-2-yl-biphenyl-3-yloxy)-propyl]-carbamic acid tert-butyl ester

    [1189] A mixture of the compound of Preparation BB1 (100 mg), 3-(Boc-amino)-1-propanol (commercial; 0.082 mL) and PPh.sub.3 (162 mg) in THF (4 mL) was treated dropwise with DEAD (40% in toluene; 0.18 mL) and the reaction mixture was further stirred at rt for 2 h. The solution was concentrated under reduced pressure and portioned between EA and water. The aq. layer was extracted with EA and the combined org. layers were washed with brine, dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The residue was purified by CC (Combiflash; Hept-EA 1:0 to 0:1), affording a colourless oil (131 mg; 79% yield).

    [1190] MS2 (ESI, m/z): 400.04 [M+H.sup.+]; t.sub.R=0.92 min.

    3.ii. [3-(3′-formyl-biphenyl-3-yloxy)-propyl]-carbamic acid tert-butyl ester

    [1191] A solution of intermediate 3.i (120 mg) and PTSA (1.5 mg) in acetone (1 mL) was stirred at rt for 1 day. The reaction mixture was filtered and evaporated under reduced pressure, affording a brown oil (115 mg; 100% yield).

    [1192] MS2 (ESI, m/z): 355.93 [M+H.sup.+]; t.sub.R=0.91 min.

    3.iii. 6-[(S)-5-(2-{[3′-(3-amino-propoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1193] Intermediate 3.ii (80 mg) and the compound of Preparation D1 (58 mg) were reacted in analogy to Example 1, step 1.i. The resulting crude tert-butyl (S)-(3-((3′-(((2-(2-oxo-3-(3-oxo-3,4-dihydro-2H-pyri do[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)-[1,1′-biphenyl]-3-yl)oxy)propyl)carbamate intermediate (124 mg) was further reacted with TFA (0.6 mL) in analogy to Example 1, step 1.ii, affording after purification an off-white lyophilisate (11 mg; 10% yield).

    [1194] MS2 (ESI, m/z): 518.08 [M+H.sup.+]; t.sub.R=0.46 min.

    Example 4

    6-[(S)-5-(2-{[3′-(2-methylamino-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1195] The compound of Preparation A3 (30 mg) and the compound of Preparation D1 (22 mg) were reacted in analogy to Example 1, step 1.i. The resulting crude tert-butyl (S)-methyl-(2-((3′-(((2-(2-oxo-3-(3-oxo-3,4-dihydro-2H-pyri do[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)-[1,1′-biphenyl]-3-yl)oxy)ethyl)carbamate (46 mg) was further reacted with TFA (0.23 mL) in analogy to Example 1, step 1.ii, affording after purification an off-white solid (3 mg; 8% yield).

    [1196] MS2 (ESI, m/z): 518.08 [M+H.sup.+]; t.sub.R=0.45 min.

    Example 5

    6-[(S)-5-(2-{[3′-(4-amino-butoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    5.i. Tert-butyl (S)-(4-((3′-(((2-(2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)-[1,1′-biphenyl]-3-yl)oxy)butyl)carbamate

    [1197] Starting from the compound of Preparation A4 (177 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as a colourless solid (54 mg; 30% yield).

    [1198] MS3 (ESI, m/z): 632.03 [M+H.sup.+]; t.sub.R=0.79 min.

    5.ii. 6-[(S)-5-(2-{[3′-(4-Amino-butoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1199] Starting from intermediate 5.i (45 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained as a colourless solid (22 mg; 59% yield).

    [1200] MS3 (ESI, m/z): 532.10 [M+H.sup.+]; t.sub.R=0.57 min.

    Example 6

    6-((S)-5-(2-(((3′-(((RS)-1-aminopropan-2-yl)oxy)-[1,1′-biphenyl]-3-yl)methyl)amino)ethyl)-2-oxooxazolidin-3-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

    6.i. Tert-butyl ((RS)-2-((3′-(((2-((S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)-[1,1′-biphenyl]-3-yl)oxy)propyl)carbamate

    [1201] Starting from the compound of Preparation A5 (146 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as an off-white oil (102 mg; 57% yield).

    [1202] MS3 (ESI, m/z): 618.00 [M+H.sup.+]; t.sub.R=0.77 min.

    6.ii. 6-((S)-5-(2-(((3′-(((RS)-1-aminopropan-2-yl)oxy)-[1,1′-biphenyl]-3-yl)methyl)amino)ethyl)-2-oxooxazolidin-3-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

    [1203] Starting from intermediate 6.i (97 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained as a colourless solid (51 mg; 63% yield).

    [1204] MS3 (ESI, m/z): 518.09 [M+H.sup.+]; t.sub.R=0.56 min.

    Example 7

    6-[(S)-5-(2-{[3′-((1R,3R)-3-amino-cyclopentyloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    7.i. Tert-butyl ((1R,3R)-3-((3′-(((2-((S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)-[1,1′-biphenyl]-3-yl)oxy)cyclopentyl)carbamate

    [1205] The title compound can be prepared starting from the compound of Preparation A6 and the compound of Preparation D1 and proceeding in analogy to Example 1, step 1.i.

    [1206] MS3 (ESI, m/z): 644.01 [M+H.sup.+]; t.sub.R=0.79 min.

    7. ii. 6-[(S)-5-(2-{[3′-((1R,3R)-3-amino-cyclopentyloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1207] The title compound can be prepared starting from intermediate 7.i and proceeding in analogy to Example 1, step 1.ii.

    [1208] MS3 (ESI, m/z): 544.09 [M+H.sup.+]; t.sub.R=0.57 min.

    Example 8

    6-[(S)-5-(2-{3-[6-(2-amino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    8.i. Tert-butyl (S)-(2-((6-(3-(((2-(2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)phenyl)pyridin-2-yl)oxy)ethyl)carbamate

    [1209] Starting from the compound of Preparation A7 (98 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound (39 mg; 22% yield) was obtained as a colourless solid.

    [1210] MS3 (ESI, m/z): 604.97 [M+H.sup.+]; t.sub.R=0.74 min.

    8.ii. 6-[(S)-5-(2-{3-[6-(2-amino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1211] Starting from intermediate 8.i. (33 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained as a colourless solid (10 mg; 37% yield).

    [1212] MS3 (ESI, m/z): 505.02 [M+H.sup.+]; t.sub.R=0.52 min.

    Example 9

    6-[(S)-2-oxo-5-(2-{3-[6-(2-pyrrolidin-1-yl-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1213] Starting from the compound of Preparation A8 (85 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as a colourless solid (102 mg; 63% yield).

    [1214] .sup.1H NMR (400 MHz, CDCl.sub.3) δ: 8.49-8.59 (m, 1H); 8.25 (s, 1H); 7.86 (d, J=7.5 Hz, 1H); 7.62-7.68 (m, 2H); 7.37-7.46 (m, 3H); 7.26 (d, J=7.5 Hz, 1H); 6.69 (d, J=8.0 Hz, 1H); 4.84 (t, J=5.3 Hz, 2H); 4.68-4.75 (m, 1H); 4.58 (s, 2H); 4.20 (m, 1H); 4.12 (m, 2H); 3.84 (dd, J.sub.1=7.0 Hz, J.sub.2=10.5 Hz, 1H); 3.45-3.50 (m, 2H); 3.23-3.30 (m, 4H); 3.00-3.12 (m, 2H); 2.18 (m, 2H); 2.04 (m, 4H).

    [1215] MS3 (ESI, m/z): 559.09 [M+H.sup.+]; t.sub.R=0.54 min.

    Example 10

    6-[(S)-5-(2-{3-[5-(2-dimethylamino-ethoxy)-pyridazin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1216] Starting from the compound of Preparation A9 (35 mg) and the compound of Preparation D1 (38 mg) and proceeding in analogy to Example 1, step 1.i, the title compound (24 mg; 35% yield) was obtained as a yellowish foam.

    [1217] .sup.1H NMR (500 MHz, CDCl.sub.3) δ: 9.13 (s, 1H); 8.28 (s, 1H); 7.79 (m, 2H); 7.47 (t, J=7.5 Hz, 1H); 7.41 (m, 1H); 7.34 (s, 1H); 7.27 (s, 1H); 4.78 (m, 1H); 4.64 (s, 2H); 4.39 (t, J=9.4 Hz, 1H); 4.30 (t, J=5.0 Hz, 2H); 3.94 (m, 3H); 2.95 (m, 1H); 2.84 (m, 3H); 2.39 (s, 6H); 2.15 (dd, J.sub.1=6.3 Hz, J.sub.2=13.6 Hz, 1H); 1.96 (m, 1H).

    [1218] MS3 (ESI, m/z): 534.11 [M+H.sup.+]; t.sub.R=0.48 min.

    Example 11

    6-[(S)-5-(2-{3-[5-(2-amino-ethoxy)-pyridin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    11.i. Tert-butyl (S)-(2-((5-(3-(((2-(2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)phenyl)pyridin-3-yl)oxy)ethyl)carbamate

    [1219] Starting from the compound of Preparation A10 (90 mg) and the compound of Preparation D1 (38 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as a yellowish foam (53 mg; 67% yield).

    [1220] MS3 (ESI, m/z): 604.97 [M+H.sup.+]; t.sub.R=0.63 min.

    11.ii. 6-[(S)-5-(2-{3-[5-(2-amino-ethoxy)-pyridin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1221] Starting from intermediate 11.i. (45 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained as a colourless solid (23 mg; 61% yield).

    [1222] MS3 (ESI, m/z): 505.06 [M+H.sup.+]; t.sub.R=0.46 min.

    Example 12

    6-[(S)-2-oxo-5-(2-{3-[6-(2-piperidin-1-yl-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1223] Starting from the compound of Preparation A11 (30 mg) and the compound of Preparation D1 (28 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as a beige foam (19 mg; 34% yield).

    [1224] MS3 (ESI, m/z): 573.05 [M+H.sup.+]; t.sub.R=0.56 min.

    Example 13

    6-[(S)-2-oxo-5-(2-{[3′-(2-piperidin-1-yl-ethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1225] Starting from the compound of Preparation A12 (45 mg) and the compound of Preparation D1 (42 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as an off-white foam (23 mg; 28% yield).

    [1226] .sup.1H NMR (500MHz, CDCl.sub.3) δ: 7.79 (d, J=8.7 Hz, 1H); 7.53 (s, 1H); 7.48 (m, 1H); 7.40 (t, J=7.6 Hz, 1H); 7.33 (t, J=7.9 Hz, 1H); 7.28 (m, 2H); 7.18 (d, J=7.7 Hz, 1H); 7.12 (s, 1H); 6.88 (dd, J.sub.1=2.0 Hz, J.sub.2=8.1 Hz, 1H); 4.77 (m, 1H); 4.60 (s, 2H); 4.20 (m, 3H); 3.88 (s, 2H); 3.77 (dd, J.sub.1=7.4 Hz, J.sub.2=10.2 Hz, 1H); 2.86 (m, 4H); 2.59 (s, 4H); 2.04 (m, 1H); 1.92 (m, 1H); 1.65 (m, 4H); 1.48 (d, J=4.3 Hz, 2H).

    [1227] MS3 (ESI, m/z): 572.06 [M+H.sup.+]; t.sub.R=0.57 min.

    Example 14

    6-[(S)-5-(2-{[3′-(1-amino-cyclopropylmethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    14.i. {1-[3′-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-biphenyl-3-yloxymethyl]-cyclopropyl}-carbamic acid tert-butyl ester

    [1228] Starting from the compound of Preparation A13 (113 mg) and the compound of Preparation D1 (60 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as an off-white oil (42 mg; 41% yield).

    [1229] MS3 (ESI, m/z): 630.01 [M+H.sup.+]; t.sub.R=0.71 min.

    14.ii. 6-[(S)-5-(2-{[3′-(1-amino-cyclopropylmethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1230] Starting from intermediate 14.i (39 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained as a colourless solid (12 mg; 38% yield).

    [1231] MS3 (ESI, m/z): 529.99 [M+H.sup.+]; t.sub.R=0.56 min.

    Example 15

    6-[(S)-5-(2-{3-[6-(2-amino-ethoxy)-pyrazin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    15.i. (2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-phenyl]-pyrazin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1232] Starting from the compound of Preparation A14 (25 mg) and the compound of Preparation D1 (21 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained, after purification by CC (Combiflash; gradient DCM to DCM/MeOH 9:1), as a colourless foam (20 mg; 45% yield).

    [1233] MS3 (ESI, m/z): 606.99 [M+H.sup.+]; t.sub.R=0.71 min.

    15.ii. 6-[(S)-5-(2-{3-[6-(2-amino-ethoxy)-pyrazin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1234] Starting from intermediate 15.i (15 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained, after purification by prep-HPLC (method 1), as a beige solid (7 mg; 60% yield).

    [1235] MS3 (ESI, m/z): 506.03 [M+H+]; t.sub.R=0.50 min.

    Example 16

    6-[(S)-5-(2-{[6-(2-amino-ethoxy)-[2,4′]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one formate

    16.i. 6-[(S)-5-(2-amino-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1236] Starting from the compound of Preparation A15 (8 mg) and the compound of Preparation D1 (7 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (9 mg; 66% yield).

    [1237] MS3 (ESI, m/z): 617.97 [M+H.sup.+]; t.sub.R=0.78 min.

    16.ii. 6-[(S)-5-(2-{[6-(2-amino-ethoxy)-[2,4′]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1238] Starting from intermediate 16.i (9 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained, after purification by prep-HPLC (method 1), as a light yellow foam (6 mg; 74% yield).

    [1239] MS3 (ESI, m/z): 506.02 [M+H+]; t.sub.R=0.50 min.

    Example 17

    6-[(S)-5-(2-{3-[6-((R)-2-amino-propoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    17.i. ((R)-1-methyl-2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1240] Starting from the compound of Preparation A16 (103 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1). as a colourless solid (15 mg; 8% yield).

    [1241] MS3 (ESI, m/z): 618.97 [M+H.sup.+]; t.sub.R=0.75 min.

    17.ii. 6-[(S)-5-(2-{3-[6-((R)-2-amino-propoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1242] Starting from intermediate 17.i (15 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained, after purification by prep-HPLC (method 1), as a colourless solid (3 mg; 21% yield).

    [1243] MS3 (ESI, m/z): 519.05 [M+H+]; t.sub.R=0.53 min.

    Example 18

    6-[(S)-5-(2-{3-[6-((S)-2-amino-propoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    18.i. ((S)-1-methyl-2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1244] Starting from the compound of Preparation A17 (103 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless solid (33 mg; 20% yield).

    [1245] MS3 (ESI, m/z): 618.96 [M+H.sup.+]; t.sub.R=0.75 min.

    18.ii. 6-[(S)-5-(2-{3-[6-((S)-2-amino-propoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1246] Starting from intermediate 18.i (30 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained, after purification by prep-HPLC (method 1), as a colourless solid (37 mg; quant.).

    [1247] MS3 (ESI, m/z): 519.07 [M+H+]; t.sub.R=0.53 min.

    Example 19

    6-[(S)-5-(2-{3-[2-(2-amino-ethoxy)-pyridin-4-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one formate

    19.i. (2-{4-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1248] Starting from the compound of Preparation A18 (112 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound (57 mg; 33% yield) was obtained as a colourless solid after purification by CC (Combiflash; DCM to DCM/MeOH 4:1).

    [1249] MS3 (ESI, m/z): 604.98 [M+H.sup.+]; t.sub.R=0.68 min.

    19.ii. 6-[(S)-5-(2-{3-[2-(2-amino-ethoxy)-pyridin-4-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one formate

    [1250] Starting from intermediate 19.i (57 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained, after purification by prep-HPLC (method 1), as a colourless solid (28 mg; 53% yield).

    [1251] MS3 (ESI, m/z): 505.08 [M+H+]; t.sub.R=0.51 min.

    Example 20

    6-[(S)-5-(2-{3-[6-(5-amino-pentyloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    20.i. (5-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-pentyl)-carbamic acid tert-butyl ester

    [1252] Starting from the compound of Preparation A19 (158 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as an off-white foam (70 mg; 38% yield).

    [1253] MS3 (ESI, m/z): 646.96 [M+H.sup.+]; t.sub.R=0.79 min.

    20.ii. 6-[(S)-5-(2-{3-[6-(5-amino-pentyloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1254] Starting from intermediate 20.i (61 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as an off-white solid (24 mg; 46% yield).

    [1255] MS3 (ESI, m/z): 547.08 [M+H+]; t.sub.R=0.57 min.

    Example 21

    6-[(S)-5-(2-{[3′-(2-amino-ethoxy)-5′-methoxy-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    21.i. {2-[5-methoxy-3′-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-biphenyl-3-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1256] Starting from the compound of Preparation A20 (178 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as an off-white foam (17 mg; 10% yield).

    [1257] MS3 (ESI, m/z): 633.95 [M+H.sup.+]; t.sub.R=0.76 min.

    21.ii. 6-[(S)-5-(2-{[3′-(2-amino-ethoxy)-5′-methoxy-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1258] Starting from intermediate 21.i (15 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as an off-white solid (4 mg; 31% yield).

    [1259] MS3 (ESI, m/z): 534.05 [M+H+]; t.sub.R=0.55 min.

    Example 22

    6-[(R)-5-(2-{3-[6-(2-amino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

    22.i. (2-{6-[3-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1, 4]thiazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1260] Starting from the compound of Preparation A7 (116 mg) and 6-[(5R)-5-(2-aminoethyl)-2-oxo-3-oxazolidinyl]-2H-1,4-benzothiazin-3(4H)-one (84 mg; prepared according to WO 2010/041219) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless oil (41 mg; 23% yield).

    [1261] MS3 (ESI, m/z): 619.92 [M+H.sup.+]; t.sub.R=0.75 min.

    22ii. 6-[(R)-5-(2-{3-[6-(2-amino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1, 4]thiazin-3-one

    [1262] Starting from intermediate 22.i (35 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as an off-white solid (14 mg; 47% yield).

    [1263] MS3 (ESI, m/z): 520.02 [M+H+]; t.sub.R=0.53 min.

    Example 23

    6-[(S)-5-(2-{3-[6-(2-morpholin-4-yl-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1264] Starting from the compound of Preparation A21 (150 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless oil (138 mg; 84% yield).

    [1265] MS3 (ESI, m/z): 575.02 [M+H.sup.+]; t.sub.R=0.52 min.

    Example $101

    6-[(S)-5-(2-{[3′-((S)-1-azetidin-2-ylmethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1266] A solution of the compound of Preparation C1 (80 mg) and the compound of Preparation D1 (56 mg) in DMF/DCM (1:4; 2.5 mL) was treated with NaBH(OAc).sub.3 (125 mg) and further stirred at rt for 1 day. The residue was partioned between sat. aq. NaHCO.sub.3 and EA. The org. layer was separated, washed with brine dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The residue was dissolved in DCM (0.5 mL) and treated with TFA (0.58 mL) and further stirred at rt for 1 h. The solution was concentrated to dryness and the residue was taken up in DCM and treated with NH.sub.4OH. The aq. layer was extracted twice with DCM. The combined org. layers were washed with brine and dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC (method 1), affording a colourless solid (3 mg; 8% yield).

    [1267] MS2 (ESI, m/z): 529.95 [M+H.sup.+]; t.sub.R=0.45 min

    Example $102

    6-((S)-2-oxo-5-(2-(((3′-(((S)-pyrrolidin-2-yl)methoxy)-[1,1′-biphenyl]-3-yl)methyl)amino)ethyl)oxazolidin-3-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

    $102.i. Tert-butyl 2-(((3′-(((2-((S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)-[1,1′-biphenyl]-3-yl)oxy)methyl)pyrrolidine-1-carboxylate

    [1268] A solution of the compound of Preparation C2 (229 mg) and the compound of Preparation D1 (100 mg) in DMF/DCM (1:4; 4.3 mL) was treated with NaBH(OAc).sub.3 (229 mg) and further stirred at rt for 1 day. The residue was diluted with DCM (5 mL), washed several times with water and brine, dried over MgSO.sub.4, filtered, concentrated under reduced pressure and purified by CC (Combiflash; DCM to DCM/MeOH 4:1), affording a colourless solid (65 mg; 28% yield).

    [1269] MS2 (ESI, m/z): 644.02 [M+H.sup.+]; t.sub.R=0.76 min.

    $102.ii. 6-((S)-2-oxo-5-(2-(((3′-(((S)-pyrrolidin-2-yl)methoxy)-[1,1′-biphenyl]-3-yl)methyl)amino)ethyl)oxazolidin-3-yl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

    [1270] A solution of intermediate $102.i (60 mg) in DCM (0.25 mL) was treatd with TFA (0.29 mL) and further stirred at rt for 1 h. The reaction mixture was evaporated to dryness, diluted with DCM and washed with aq sat. NaHCO.sub.3 solution, water and brine, dried over MgSO.sub.4, filtered, concentrated under reduced pressure and purified by prep-HPLC (method 1), affording a colourless solid (24 mg; 47% yield).

    [1271] MS2 (ESI, m/z): 544.09 [M+H.sup.+]; t.sub.R=0.46 min.

    Example $103

    6-[(S)-2-oxo-5-(2-{[3′-((RS)-pyrrolidin-3-yloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $103.i. Tert-butyl (RS)-3-((3′-(((2-((S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)-1-[1,1′-biphenyl]-3-yl)oxy)pyrrolidine-1-carboxylate

    [1272] Starting from the compound of Preparation C3 (176 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained as a colourless solid (39 mg; 22% yield).

    [1273] MS2 (ESI, m/z): 630.01 [M+H.sup.+]; t.sub.R=0.73 min.

    [1274] $103.ii. 6-[(S)-2-oxo-5-(2-{[3′-((RS)-pyrrolidin-3-yloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1275] Starting from intermediate $103.i. (35 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained as a colourless solid (13 mg; 45% yield).

    [1276] MS2 (ESI, m/z): 529.95 [M+H.sup.+]; t.sub.R=0.47 min.

    Example $104

    6-[(S)-5-(2-{[3′-((S)-1-methyl-azetidin-2-ylmethoxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1277] Starting from the compound of Preparation C4 (35 mg) and the compound of Preparation D1 (34 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained as an off-white foam (65 mg; 96% yield).

    [1278] .sup.1H NMR (CDCl.sub.3) δ: 8.49-8.57 (m, 1H); 7.68-7.71 (m, 2H); 7.37-7.46 (m, 3H); 7.21-7.28 (m, 3H); 7.10-7.13 (m, 1H); 6.83-6.86 (m, 1H); 4.63 (m, 1H); 4.56 (m, 2H); 4.50 (m, 1H); 4.29 (m, 1H); 4.18 (m, 2H); 4.06 (m, 3H); 3.57 (m, 1H); 3.45-3.59 (m, 1H); 2.98-3.08 (m, 2H); 2.79-2.81 (m, 3H); 2.56-2.61 (m, 1H); 2.38-2.45 (m, 1H).

    [1279] MS3 (ESI, m/z): 544.07 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $105

    6-[(S)-5-(2-{[3′-(azetidin-3-yloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $105.i. Tert-butyl (S)-3-((3′-(((2-(2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)-[1,1′-biphenyl]-3-yl)oxy)azetidine-1-carboxylate

    [1280] Starting from the compound of Preparation C5 (66 mg) and the compound of Preparation D1 (52 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained as a colourless oil (52 mg; 45% yield).

    [1281] MS3 (ESI, m/z): 616.00 [M+H.sup.+]; t.sub.R=0.78 min.

    $105.ii. 6-[(S)-5-(2-{[3′-(azetidin-3-yloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1282] Starting from intermediate $105.i (48 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained as a colourless solid (10 mg; 25% yield).

    [1283] MS3 (ESI, m/z): 516.09 [M+H.sup.+]; t.sub.R=0.53 min.

    Example $106

    6-[(S)-5-(2-{3-[6-(azetidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $106.i. Tert-butyl (S)-3-(((6-(3-(((2-(2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)phenyl)pyridin-2-yl)oxy)methypazetidine-1-carboxylate

    [1284] Starting from the compound of Preparation C6 (40 mg) and the compound of Preparation D1 (32 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained as a light yellow oil (41 mg; 60% yield).

    [1285] MS3 (ESI, m/z): 630.97 [M+H.sup.+]; t.sub.R=0.77 min.

    $106.ii. 6-[(S)-5-(2-{3-[6-(azetidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1286] Starting from intermediate $106.i (35 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained as a yellow foam (23 mg; 78% yield).

    [1287] MS3 (ESI, m/z): 531.06 [M+H.sup.+]; t.sub.R=0.53 min.

    Example $107

    6-[(S)-5-(2-{3-[6-(azetidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $107. i. 3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-azetidine-1-carboxylic acid tert-butyl ester

    [1288] Starting from the compound of Preparation C7 (35 mg) and the compound of Preparation D1 (29 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained, after purification by CC (Combiflash; gradient DCM to DCM/MeOH 9:1), as a colourless foam (150 mg; 25% yield).

    [1289] MS3 (ESI, m/z): 617.97 [M+H.sup.+]; t.sub.R=0.78 min.

    $107.ii. 6-[(S)-5-(2-{3-[6-(azetidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1290] Starting from intermediate $107.i (12 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as an orange foam (4 mg; 41% yield).

    [1291] MS3 (ESI, m/z): 517.06 [M+H+]; t.sub.R=0.53 min.

    Example $108: 6-[(S)-5-(2-{3-[6-((S)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-oneformate

    $108.i. (S)-2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxymethyl}-azetidine-1-carboxylic acid tert-butyl ester

    [1292] Starting from the compound of Preparation C8 (163 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained, after purification by CC (Combiflash; gradient DCM to DCM/MeOH 4:1), as a colourless foam (115 mg; 63% yield).

    [1293] MS3(ESI, m/z): 630.94 [M+H.sup.+]; t.sub.R=0.77 min.

    $108.ii. 6-[(S)-5-(2-{3-[6-((S)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one formate

    [1294] Starting from intermediate $108.i (114 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 1), as a colourless solid (75 mg; 72% yield).

    [1295] MS3 (ESI, m/z): 531.08 [M+H+]; t.sub.R=0.53 min.

    Example $109

    6-[(S)-5-(2-{3-[6-((RS)-1-morpholin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one formate

    $ 109.i. (RS)-2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxymethyl}-morpholine-4-carboxylic acid tert-butyl ester

    [1296] Starting from the compound of Preparation C9 (153 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained, after purification by CC (Combiflash; gradient DCM to DCM/MeOH 4:1), as a colourless solid (75 mg; 39% yield).

    [1297] MS3 (ESI, m/z): 660.92 [M+H.sup.+]; t.sub.R=0.76 min.

    $109.ii. 6-[(S)-5-(2-{3-[6-((RS)-1-morpholin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one formate

    [1298] Starting from intermediate $109.i (73 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 1), as a colourless solid (46 mg; 68% yield).

    [1299] .sup.1H NMR (500 MHz, CDCl.sub.3) δ: 8.12 (s, 1H); 7.87 (d, J=7.8 Hz, 1H); 7.73 (d, J=8.7 Hz, 1H); 7.65-7.69 (m, 1H); 7.43-7.49 (m, 1H); 7.35-7.39 (m, 2H); 7.26-7.31 (m, 1H); 6.78 (d, J=8.2 Hz, 1H); 4.74-4.79 (m, 1H); 4.57-4.63 (m, 3H); 4.44 (m, 1H); 4.16-4.25 (m, 2H); 3.99-4.11 (m, 3H); 3.82-3.86 (m, 2H); 3.36-3.39 (m, 1H); 2.99-3.08 (m, 4H); 2.83-2.88 (m, 1H); 2.11-2.16 (m, 2H).

    [1300] MS3 (ESI, m/z): 560.93 [M+H+]; t.sub.R=0.53 min.

    Example $110: 6-[(S)-5-(2-{3-[6-((RS)-1-morpholin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one formate

    $110.i. (R)-3-{6-[3-({2-[(RS)-2-Oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxymethyl}-morpholine-4-carboxylic acid tert-butyl ester

    [1301] Starting from the compound of Preparation C10 (133 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained, after purification by CC (Combiflash; gradient DCM to DCM/MeOH 4:1), as a colourless solid (72 mg; 38% yield).

    [1302] MS3 (ESI, m/z): 660.92 [M+H.sup.+]; t.sub.R=0.75 min.

    $110.ii. 6-[(S)-5-(2-{3-[6-((RS)-1-Morpholin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one formate

    [1303] Starting from intermediate $110.i (71 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 1), as a colourless solid (36 mg; 56% yield).

    [1304] MS3 (ESI, m/z): 560.94 [M+H+]; t.sub.R=0.53 min.

    Example $111

    6-[(S)-2-oxo-5-(2-{3-[6-((RS)-piperidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one formate

    $111.i. (RS)-3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-piperidine-1-carboxylic acid tert-butyl ester

    [1305] Starting from the compound of Preparation C11 (183 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained, after purification by CC (Combiflash; gradient DCM to DCM/MeOH 4:1), as a colourless solid (38 mg; 20% yield).

    [1306] MS3 (ESI, m/z): 644.97 [M+H.sup.+]; t.sub.R=0.78 min.

    $111.ii. 6-[(S)-2-oxo-5-(2-{3-[6-((RS)-piperidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one formate

    [1307] Starting from intermediate $111.i (37 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 1), as a colourless solid (17 mg; 50% yield).

    [1308] MS3 (ESI, m/z): 544.99 [M+H+]; t.sub.R=0.54 min.

    Example $112: (3S*,4*)-6-[(S)-5-(2-{3-[6-(4-methoxy-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $112.1. (3S*,4S*)-3-methoxy-4-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1309] This compound can be prepared starting from cis-4-methoxy-3-pyrrolidinol hydrochloride and the compound of Preparation D1 and proceeding successively in analogy to Preparation C12 (all 3 steps) and Example $102, step $102.i.

    $112.ii. (3S*,4S*)-6-[(S)-5-(2-{3-[6-(4-methoxy-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1310] This compound can be prepared starting from intermediate $112.i and proceeding in analogy to Example $102, step $102.ii.

    Example $113

    6-[(S)-5-(2-{3-[6-(1-methyl-azetidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1311] Starting from the compound of Preparation C13 (35 mg) and the compound of Preparation D1 (36 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained as an off-white foam (32 mg; 47% yield).

    [1312] MS3 (ESI, m/z): 544.97 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $114

    6-[(S)-5-(2-{3-[5-(azetidin-3-yloxy)-pyridazin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $ 114.i. 3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-phenyl]-pyridazin-4-yloxy}-azetidine-1-carboxylic acid tert-butyl ester

    [1313] Starting from the compound of Preparation C14 (64 mg) and the compound of Preparation D1 (50 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as a colourless solid (73 mg; 65% yield).

    [1314] MS1 (ESI, m/z): 618.03 [M+H.sup.+]; t.sub.R=0.70 min.

    $114.ii. 6-[(S)-5-(2-{3-[5-(azetidin-3-yloxy)-pyridazin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1315] To a solution of intermediate $114.i (73 mg) in DCM (3.6 mL) was added 4.0M HCl in dioxane (0.29 mL) at 0° C. and further stirred at rt for 1.5 h. The reaction mixture was evaporated to dryness and purified by prep-HPLC (method 3), affording a colourless solid (40 mg; 66% yield).

    [1316] MS1 (ESI, m/z): 517.96 [M+H.sup.+]; t.sub.R=0.48 min.

    Example $115

    6-[(S)-2-oxo-5-(2-{3-[4-((R)-pyrrolidin-3-yloxy)-pyrimidin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $115.i. (R)-3-{2-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-phenyl]-pyrimidin-4-yloxy}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1317] Starting from the compound of Preparation C15 (142 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, however using a 3/1 DCM/MeOH mixture as solvent, the title compound was obtained as a colourless solid (98 mg; 54% yield).

    [1318] MS3 (ESI, m/z): 631.94 [M+H.sup.+]; t.sub.R=0.71 min.

    $115.ii. 6-[(S)-2-oxo-5-(2-{3-[4-((R)-pyrrolidin-3-yloxy)-pyrimidin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1319] Starting from intermediate $115.i (90 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (30 mg; 40% yield).

    [1320] .sup.1H NMR (500 MHz, CDCl.sub.3) δ: 8.54 (m, 1H); 8.06 (m, 1H); 7.94 (m, 1H); 7.75 (m, 1H); 7.47 (m, 2H); 7.39 (m, 1H); 7.28 (m, 1H); 5.62 (m, 1H); 4.78 (m, 1H); 4.61 (m, 2H); 4.24 (m, 1H); 3.90 (m, 2H); 3.79 (m, 1H); 3.24 (m, 3H); 3.01 (m, 1H); 2.86 (m, 2H); 2.20 (m, 3H); 1.99 (m, 2H).

    [1321] MS3 (ESI, m/z): 532.06 [M+H.sup.+]; t.sub.R=0.49 min.

    Example $116

    6-[(S)-2-oxo-5-(2-{3-[6-((R)-pyrrolidin-3-yloxy)-pyrimidin-4-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $116.i. (R)-3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyrimidin-4-yloxy}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1322] Starting from the compound of Preparation C16 (150 mg) and the compound of Preparation D1 (102 mg) and proceeding in analogy to Example 1, step 1.i, however using a 3/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless solid (198 mg; 86% yield).

    [1323] MS3 (ESI, m/z): 631.95 [M+H.sup.+]; t.sub.R=0.72 min.

    $116.ii. 6-[(S)-2-oxo-5-(2-{3-[6-((R)-pyrrolidin-3-yloxy)-pyrimidin-4-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1324] Starting from intermediate $116.i (190 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (77 mg; 48% yield).

    [1325] MS3 (ESI, m/z): 532.02 [M+H.sup.+]; t.sub.R=0.49 min.

    Example $117

    6-{(S)-5-[2-({3′-[2-((1R*,5S*,6RS)-6-amino-3-aza-bicyclo[3.1.0]hex-3-yl)-ethoxy]-biphenyl-3-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $117.i. ((1R*,5S*,6RS)-3-{2-[3′-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-biphenyl-3-yloxy]-ethyl}-3-aza-bicyclo[3.1.0]hex-6-yl)-carbamic acid tert-butyl ester

    [1326] Starting from the compound of Preparation C17 (60 mg) and the compound of Preparation D1 (40 mg) and proceeding in analogy to Example 1, step 1.i, however using a 2/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless oil (54 mg; 56% yield).

    [1327] MS3 (ESI, m/z): 684.99 [M+H.sup.+]; t.sub.R=0.61 min.

    $117. ii. 6-{(S)-5-[2-({3′-[2-((1R*,5S*,6RS)-6-amino-3-aza-bicyclo[3.1.0]hex-3-yl)-ethoxy]-biphenyl-3-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1328] Starting from intermediate $117.i (49 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (14 mg; 33% yield).

    [1329] MS3 (ESI, m/z): 585.05 [M+H.sup.+]; t.sub.R=0.48 min.

    Example $118

    6-[(S)-2-oxo-5-(2-{3-[6-((R)-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $118.i. (R)-3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1330] Starting from the compound of Preparation C18 (396 mg) and the compound of Preparation D1 (94 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained as a light yellow solid (133 mg; 65% yield).

    [1331] MS3 (ESI, m/z): 631.15 [M+H.sup.+]; t.sub.R=0.76 min.

    $118.ii. 6-[(S)-2-oxo-5-(2-{3-[6-((R)-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1332] Starting from intermediate $118.i (115 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (42 mg; 43% yield).

    [1333] MS3 (ESI, m/z): 531.13 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $119

    6-[(S)-2-oxo-5-(2-{3-[6-((S)-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $119.i. (S)-3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1334] Starting from the compound of Preparation C19 (384 mg) and the compound of Preparation D1 (91 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained as a light yellow solid (132 mg; 67% yield).

    [1335] MS3 (ESI, m/z): 631.13 [M+H.sup.+]; t.sub.R=0.76 min.

    $119.ii. 6-[(S)-2-oxo-5-(2-{3-[6-((S)-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1336] Starting from intermediate $119.i (115 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (69 mg; 71% yield).

    [1337] MS3 (ESI, m/z): 531.15 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $120

    6-[(S)-5-(2-{3-[6-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1338] Starting from the compound of Preparation C20 (376 mg) and the compound of Preparation D1 (97 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (26 mg; 14% yield). MS3 (ESI, m/z): 545.07 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $121

    6-[(S)-5-(2-{3-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1339] Starting from the compound of Preparation C21 (382 mg) and the compound of Preparation D1 (79 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (16 mg; 11% yield).

    [1340] MS3 (ESI, m/z): 545.06 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $122

    6-[(S)-5-(2-{3-[6-(1-methyl-azetidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1341] Starting from the compound of Preparation C22 (19 mg) and the compound of Preparation D1 (21 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (6 mg; 16% yield).

    [1342] MS3 (ESI, m/z): 531.11 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $123

    6-[(S)-5-(2-{3-[6-((S)-1-methyl-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1343] Starting from the compound of Preparation C23 (17 mg) and the compound of Preparation D1 (16 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (14 mg; 47% yield).

    [1344] MS3 (ESI, m/z): 545.07 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $124

    6-[(S)-5-(2-{3-[6-((R)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $124.i. (R)-2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxymethyl}-azetidine-1-carboxylic acid tert-butyl ester

    [1345] Starting from the compound of Preparation C24 (50 mg) and the compound of Preparation D1 (40 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained as a light off-white foam (43 mg; 50% yield).

    [1346] MS3 (ESI, m/z): 631.12 [M+H.sup.+]; t.sub.R=0.77 min.

    $124.ii. 6-[(S)-5-(2-{3-[6-((R)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1347] Starting from intermediate $124.i (40 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (21 mg; 62% yield).

    [1348] MS3 (ESI, m/z): 531.10 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $125

    6-[(S)-5-(2-{3-[6-((R)-1-methyl-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1349] Starting from the compound of Preparation C25 (8 mg) and the compound of Preparation D1 (8 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (6 mg; 39% yield).

    [1350] MS3 (ESI, m/z): 545.06 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $126

    6-[(S)-5-(2-{3-[6-((RS)-1-ethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1351] Starting from the compound of Preparation C26 (85 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless solid (39 mg; 24% yield).

    [1352] MS3 (ESI, m/z): 599.13 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $127

    6-[(S)-5-(2-{3-[6-(1-methyl-piperidin-4-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1353] Starting from the compound of Preparation C27 (69 mg) and the compound of Preparation D1 (65 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless solid (19 mg; 14% yield).

    [1354] MS3 (ESI, m/z): 599.13 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $128

    6-[(S)-5-(2-{[6-((S)-1-methyl-pyrrolidin-3-yloxy)-[2,4]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1355] Starting from the compound of Preparation C28 (48 mg) and the compound of Preparation D1 (50 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (34 mg; 37% yield).

    [1356] MS3 (ESI, m/z): 546.13 [M+H.sup.+]; t.sub.R=0.52 min.

    Example $129

    6-[(S)-5-(2-{[6′-((S)-1-methyl-pyrrolidin-3-yloxy)-[2,2]bipyridinyl-6-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1357] Starting from the compound of Preparation C29 (52 mg) and the compound of Preparation D1 (54 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (34 mg; 43% yield).

    [1358] MS3 (ESI, m/z): 546.15 [M+H.sup.+]; t.sub.R=0.52 min.

    Example $130

    6-[(S)-5-(2-{3-[6-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1359] Starting from the compound of Preparation C30 (69 mg) and the compound of Preparation D1 (65 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (12 mg; 9% yield).

    [1360] MS3 (ESI, m/z): 559.16 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $131

    6-[(S)-5-(2-{3-[6-((3S,5S)-5-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $ 131.i. (2S, 4S)-2-methyl-4-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3, 4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1361] Starting from the compound of Preparation C31 (183 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained as a colourless solid (110 mg; 59% yield).

    [1362] MS3 (ESI, m/z): 645.15 [M+H.sup.+]; t.sub.R=0.80 min.

    $131.ii. 6-[(S)-5-(2-{3-[6-((3S,5S)-5-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1363] Starting from intermediate $131.i (106 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as an off-white solid (23 mg; 26% yield).

    [1364] .sup.1H NMR (500 MHz, CDCl.sub.3) δ: 7.99 (m, 1H); 7.88 (m, 1H); 7.75 (m, 1H); 7.61 (m, 1H); 7.41 (m, 1H); 7.33 (d, J=7.5 Hz, 2H); 7.27 (m, 1H); 6.63 (m, 1H); 5.64 (m, 1H); 4.75 (m, 1H); 4.60 (m, 2H); 4.21 (m, 1H); 3.87 (m, 2H); 3.77 (dd, J=7.3, 10.2 Hz, 1H); 3.62 (dd, J=5.7, 12.6 Hz, 1H); 3.54 (m, 1H); 3.12 (dd, J=3.0, 12.6 Hz, 1H); 2.85 (m, 2H); 2.24 (m, 1H); 2.01 (m, 3H); 1.88 (m, 1H); 1.70 (m, 1H); 1.26 (m, 3H).

    [1365] MS3 (ESI, m/z): 545.05 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $132

    6-[(S)-2-oxo-5-(2-{3-[6-((R)-1-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $132.i. (R)-2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxymethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester:

    [1366] Starting from the compound of Preparation C32 (137 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained as a colourless solid (60 mg; 32% yield).

    [1367] MS3 (ESI, m/z): 645.16 [M+H.sup.+]; t.sub.R=0.79 min.

    $132.ii. 6-[(S)-2-oxo-5-(2-{3-[6-((R)-1-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1368] Starting from intermediate $132.i (53 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as an off-white solid (25 mg; 56% yield).

    [1369] MS3 (ESI, m/z): 545.06 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $133

    6-[(S)-2-oxo-5-(2-{3-[6-((S)-1-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $133.i. (S)-2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-pheny]-pyridin-2-yloxymethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1370] Starting from the compound of Preparation C33 (137 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained as a colourless foam (42 mg; 23% yield).

    [1371] MS3 (ESI, m/z): 645.15 [M+H.sup.+]; t.sub.R=0.79 min.

    $133.ii. 6-[(S)-2-oxo-5-(2-{3-[6-((S)-1-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1372] Starting from intermediate $133.i (38 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (22 mg; 68% yield).

    [1373] MS3 (ESI, m/z): 545.05 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $134

    6-[(S)-5-(2-{3-[6-((RS)-1-isopropyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1374] Starting from the compound of Preparation C34 (48 mg) and the compound of Preparation D1 (43 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash, gradient: DCM to DCM/MeOH 4:1), as a colourless solid (25 mg; 28% yield).

    [1375] MS3 (ESI, m/z): 573.18 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $135

    6-[(S)-5-(2-{3-[6-((2RS,3RS)-2-methyl-azetidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1376] $135.i. (2RS,3RS)-2-methyl-3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-azetidine-1-carboxylic acid tert-butyl ester

    [1377] Starting from the compound of Preparation C35 (46 mg) and the compound of Preparation D1 (35 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained as a colourless oil (44 mg; 56% yield).

    [1378] MS1 (ESI, m/z): 631.07 [M+H.sup.+]; t.sub.R=0.78 min.

    $135.ii. 6-[(S)-5-(2-{3-[6-((2RS,3RS)-2-methyl-azetidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1379] Starting from intermediate $135.i (39 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (7 mg; 22% yield).

    [1380] MS3 (ESI, m/z): 531.12 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $136

    6-[(S)-5-(2-{3-[4-methoxy-6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1381] Starting from the compound of Preparation C36 (28 mg) and the compound of Preparation D1 (21 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained after purification by prep-HPLC (method 2 followed by method 1) as a colourless solid (5 mg; 11% yield).

    [1382] MS3 (ESI, m/z): 575.16 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $137

    6-[(S)-5-(2-{3-[4-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrimidin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1383] Starting from the compound of Preparation C37 (10 mg) and the compound of Preparation D1 (7 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained after purification by prep-HPLC (method 2 followed by method 1) as a beige lyophilisate (2 mg; 15% yield).

    [1384] MS3 (ESI, m/z): 546.15 [M+H.sup.+]; t.sub.R=0.51 min.

    Example $138

    6-[(S)-5-(2-{[6-((S)-1-methyl-pyrrolidin-3-yloxy)-[2,3′]bipyridinyl-5′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1385] Starting from the compound of Preparation C38 (55 mg) and the compound of Preparation D1 (57 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained after purification by prep-HPLC (method 2) as an off-white solid (21 mg; 20% yield).

    [1386] MS3 (ESI, m/z): 546.12 [M+H.sup.+]; t.sub.R=0.49 min.

    Example $139

    6-[(S)-5-(2-{[6′-((S)-1-methyl-pyrrolidin-3-yloxy)-[2,2]bipyridinyl-4-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1387] Starting from the compound of Preparation C39 (48 mg) and the compound of Preparation D1 (50 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (34 mg; 37% yield).

    [1388] .sup.1H NMR (500 MHz, DMSO-d6) δ: 11.37-11.10 (m, 1H); 8.58 (d, J=4.9 Hz, 1H); 8.35 (s, 1H); 7.97 (d, J=7.3 Hz, 1H); 7.82 (m, 1H); 7.59 (d, J=8.7 Hz, 1H); 7.42 (d, J=8.7 Hz, 1H); 7.39 (dd, J=4.9, 1.1 Hz, 1H); 6.83 (d, J=8.1 Hz, 1H); 5.51-5.47 (m, 1H); 4.84 (m, 1H); 4.61 (s, 2H); 4.23 (m, 1H); 3.85 (s, 2H); 3.76 (dd, J=10.0, 7.3 Hz, 1H); 2.97-2.84 (m, 1H); 2.77-2.62 (m, 4H); 2.45-2.32 (m, 3H); 2.23 (s, 3H); 2.03-1.91 (m, 2H); 1.90-1.79 (m, 1H).

    [1389] MS3 (ESI, m/z): 546.13 [M+H.sup.+]; t.sub.R=0.50 min.

    Example $140

    6-[(S)-5-(2-{3-[6-((R)-1-methyl-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1390] Starting from the compound of Preparation C40 (77 mg) and the compound of Preparation D1 (72 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless solid (16 mg; 11% yield).

    [1391] MS3 (ESI, m/z): 300.56 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $141

    6-[(S)-5-(2-{3-[6-((S)-1-methyl-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1392] Starting from the compound of Preparation C41 (77 mg) and the compound of Preparation D1 (72 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless solid (42 mg; 29% yield).

    [1393] MS3 (ESI, m/z): 300.71 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $142

    6-[(RS)-5-(2-{3-[6-((S)-1-methyl-piperidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1394] Starting from the compound of Preparation C42 (31 mg) and the compound of Preparation D1 (29 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 4:1), as a colourless solid (16 mg; 28% yield).

    [1395] MS3 (ESI, m/z): 300.70 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $143

    6-[(S)-2-oxo-5-(2-{3-[6-((R)-1-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $143.i. (R)-3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxymethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1396] Starting from the compound of Preparation C43 (110 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained as a colourless solid (113 mg; 61% yield).

    [1397] MS3 (ESI, m/z): 645.14 [M+H.sup.+]; t.sub.R=0.78 min.

    $143.ii. 6-[(S)-2-oxo-5-(2-{3-[6-((R)-1-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1398] Starting from intermediate $143.i (100 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (36 mg; 43% yield).

    [1399] MS3 (ESI, m/z): 545.04 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $144

    6-[(S)-2-oxo-5-(2-{3-[6-((S)-1-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $ 144.i. (S)-3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxymethyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1400] Starting from the compound of Preparation C44 (110 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example $102, step $102.i, however using a 5/3 DCM/MeOH mixture as solvent, the title compound was obtained as a colourless oil (124 mg; 67% yield).

    [1401] MS3 (ESI, m/z): 645.15 [M+H.sup.+]; t.sub.R=0.78 min.

    $144.ii. 6-[(S)-2-oxo-5-(2-{3-[6-((S)-1-pyrrolidin-3-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1402] Starting from intermediate $144.i (100 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (51 mg; 61% yield).

    [1403] MS3 (ESI, m/z): 545.03 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $145

    6-{(S)-5-[2-({6-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrazin-2-yl]-pyridin-2-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1404] Starting from the compound of Preparation C45 (45 mg) and the compound of Preparation D1 (46 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (46 mg; 53% yield).

    [1405] MS3 (ESI, m/z): 547.09 [M+H.sup.+]; t.sub.R=0.50 min.

    Example $146

    6-{(S)-5-[2-({5-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrazin-2-yl]-pyridin-3-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1406] Starting from the compound of Preparation C46 (50 mg) and the compound of Preparation D1 (51 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (41 mg; 43% yield).

    [1407] .sup.1H NMR (500 MHz, DMSO-d6) δ: 11.19-11.24 (m, 1H); 9.18 (d, J=2.1 Hz, 1H); 8.89 (s, 1H); 8.64 (d, J=1.9 Hz, 1H); 8.43 (t, J=2.0 Hz, 1H); 8.29 (s, 1H); 7.58 (d, J=8.7 Hz, 1H); 7.42 (d, J=8.7 Hz, 1H); 5.51-5.49 (m, 1H); 4.83 (m, 1H); 4.61 (s, 2H); 4.22 (m, 1H); 3.94-3.81 (m, 2H); 3.77 (dd, J=10.1, 7.3 Hz, 1H); 2.84 (dd, J=10.7, 6.1 Hz, 1H); 2.70-2.64 (m, 4H); 2.42-2.32 (m, 3H); 2.26 (s, 3H); 2.03-1.83 (m, 3H).

    [1408] MS3 (ESI, m/z): 547.11 [M+H.sup.+]; t.sub.R=0.48 min.

    Example $147

    6-{(S)-5-[2-({2-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrazin-2-yl]-pyridin-4-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1409] Starting from the compound of Preparation C47 (50 mg) and the compound of Preparation D1 (51 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (38 mg; 40% yield).

    [1410] MS3 (ESI, m/z): 547.09 [M+H.sup.+]; t.sub.R=0.49 min.

    Example $148

    6-{(S)-5-[2-({4-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyrazin-2-yl]-pyridin-2-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1411] Starting from the compound of Preparation C48 (48 mg) and the compound of Preparation D1 (49 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (28 mg; 30% yield).

    [1412] MS3 (ESI, m/z): 547.10 [M+H.sup.+]; t.sub.R=0.49 min.

    Example $149

    6-[(R)-5-(2-{3-[6-(1-methyl-azetidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

    [1413] Starting from the compound of Preparation C22 (40 mg) and 6-[(5R)-5-(2-aminoethyl)-2-oxo-3-oxazolidinyl]-2H-1,4-benzothiazin-3(4H)-one (44 mg; prepared according to WO 2010/041219) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (19 mg; 23% yield).

    [1414] MS3 (ESI, m/z): 546.10 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $150

    6-[(R)-5-(2-{3-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

    [1415] Starting from the compound of Preparation C21 (40 mg) and 6-[(5R)-5-(2-aminoethyl)-2-oxo-3-oxazolidinyl]-2H-1,4-benzothiazin-3(4H)-one (42 mg; prepared according to WO 2010/041219) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (36 mg; 45% yield).

    [1416] MS3 (ESI, m/z): 560.15 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $151

    6-[(R)-5-(2-{3-[6-((S)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $ 151.i. (S)-2-{6-[3-({2-[(R)-2-oxo-3-(3-oxo-3, 4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxymethyl}-azetidine-1-carboxylic acid tert-butyl ester

    [1417] Starting from the compound of Preparation C8 (80 mg) and 6-[(R)-5-(2-amino-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one (66 mg; prepared according to WO 2014/170821) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained as a yellow oil (42 mg; 47% yield).

    [1418] MS3 (ESI, m/z): 631.15 [M+H.sup.+]; t.sub.R=0.77 min.

    $151.ii. 6-[(R)-5-(2-{3-[6-((S)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1419] Starting from intermediate $151.i (35 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a yellowish solid (15 mg; 64% yield).

    [1420] MS3 (ESI, m/z): 531.16 [M+H.sup.+]; t.sub.R=0.54 min.

    Example $152

    6-[(R)-5-(2-{3-[6-((S)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

    $152.i. (S)-2-{6-[3-({2-[(R)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxymethyl}-azetidine-1-carboxylic acid tert-butyl ester

    [1421] Starting from the compound of Preparation C8 (60 mg) and 6-[(5R)-5-(2-aminoethyl)-2-oxo-3-oxazolidinyl]-2H-1,4-benzothiazin-3(4H)-one (42 mg; prepared according to WO 2010/041219) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained as a light yellowish oil (32 mg; 47% yield).

    [1422] MS3 (ESI, m/z): 645.99 [M+H.sup.+]; t.sub.R=0.79 min.

    $152.ii. 6-[(R)-5-(2-{3-[6-((S)-1-azetidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

    [1423] Starting from intermediate $152.i (27 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (17 mg; 75% yield).

    [1424] MS3 (ESI, m/z): 546.13 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $153

    6-[(S)-5-(2-{3-[5-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1425] Starting from the compound of Preparation C49 (98 mg) and the compound of Preparation D1 (96 mg) and proceeding in analogy to Example $102, step $102.i, however using a 4/1 DCM/MeOH mixture as solvent and adding AcOH (0.020 mL), the title compound was obtained as a colourless oil (39 mg; 20% yield).

    [1426] MS1 (ESI, m/z): 545.97 [M+H.sup.+]; t.sub.R=0.49 min.

    Example $154

    6-[(S)-5-(2-{3-[4-(2-amino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $154.i. (2-{2-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-phenyl]-pyridin-4-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1427] Starting from the compound of Preparation C50 (80 mg) and the compound of Preparation D1 (68 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained as a yellowish foam (53 mg; 38% yield).

    [1428] MS3 (ESI, m/z): 605.98 [M+H.sup.+]; t.sub.R=0.58 min.

    $154.ii. 6-[(S)-5-(2-{3-[4-(2-amino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1429] Starting from intermediate $154.i (50 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (25 mg; 60% yield).

    [1430] MS3 (ESI, m/z): 505.06 [M+H.sup.+]; t.sub.R=0.42 min.

    Example $155

    6-((S)-5-{2-[(3′-{2-[bis-(2-amino-ethyl)-amino]-ethoxy}-biphenyl-3-ylmethyl)-amino]-ethyl}-2-oxo-oxazolidin-3-yl)-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $155.i. [2-((2-tert-butoxycarbonylamino-ethyl)-{2-[3′-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-biphenyl-3-yloxy]-ethyl}-amino)-ethyl]-carbamic acid tert-butyl ester

    [1431] Starting from the compound of Preparation C51 (15 mg) and the compound of Preparation D1 (8 mg) and proceeding in analogy to Example $102, step $102.i, however using a 2/1 DCM/MeOH mixture as solvent, the title compound was obtained as an off-white solid (11 mg; 48% yield).

    [1432] MS3 (ESI, m/z): 790.01 [M+H.sup.+]; t.sub.R=0.69 min.

    $155.ii. 6-((S)-5-{2-[(3′-{2-[bis-(2-amino-ethyl)-amino]-ethoxy}-biphenyl-3-ylmethyl)-amino]-ethyl}-2-oxo-oxazolidin-3-yl)-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1433] Starting from intermediate $155.i (9 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (1 mg; 13% yield).

    [1434] MS3 (ESI, m/z): 590.13 [M+H.sup.+]; t.sub.R=0.49 min.

    Example $156

    6-{(S)-5-[2-(3-{6-[2-(2-amino-ethylamino)-ethoxy]-pyridin-2-yl}-benzylamino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $156.i. (2-tert-butoxycarbonylamino-ethyl)-(2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1435] Starting from the compound of Preparation C52 (138 mg) and the compound of Preparation D1 (79 mg) and proceeding in analogy to Example $102, step $102.i, however using a 2/1 DCM/MeOH mixture as solvent, the title compound was obtained as a colourless solid (58 mg; 28% yield).

    [1436] MS3 (ESI, m/z): 749.07 [M+H.sup.+]; t.sub.R=0.80 min.

    $156.ii. 6-{(S)-5-[2-(3-{6-[2-(2-amino-ethylamino)-ethoxy]-pyridin-2-yl}-benzylamino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1437] Starting from intermediate $156.i (49 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (23 mg; 64% yield).

    [1438] MS3 (ESI, m/z): 548.16 [M+H.sup.+]; t.sub.R=0.48 min.

    Example $157

    6-[(S)-5-(2-{[4-(2-amino-ethoxy)-[2,4]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $ 157.i. {2-[2′-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3, 2-b][1, 4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-[2,4 ′]bipyridinyl-4-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1439] Starting from the compound of Preparation C53 (50 mg) and the compound of Preparation D1 (41 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained as a beige foam (38 mg; 43% yield).

    [1440] MS3 (ESI, m/z): 606.15 [M+H.sup.+]; t.sub.R=0.61 min.

    $157.ii. 6-[(S)-5-(2-{[4-(2-amino-ethoxy)-[2,4′]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1441] Starting from intermediate $157.i (35 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a yellow solid (24 mg; 82% yield).

    [1442] MS3 (ESI, m/z): 506.08 [M+H.sup.+]; t.sub.R=0.45 min.

    Example $158

    6-{(S)-5-[2-({4-[6-(2-amino-ethoxy)-pyrazin-2-yl]-pyridin-2-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $158.i. (2-{6-[2-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-pyridin-4-yl]-pyrazin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1443] Starting from the compound of Preparation C54 (60 mg) and the compound of Preparation D1 (49 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained as a beige foam (74 mg; 70% yield).

    [1444] MS3 (ESI, m/z): 607.14 [M+H.sup.+]; t.sub.R=0.67 min.

    $158.ii. 6-{(S)-5-[2-({4-[6-(2-amino-ethoxy)-pyrazin-2-yl]-pyridin-2-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1445] Starting from intermediate $158.i (65 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a yellow solid (32 mg; 59% yield).

    [1446] .sup.1H NMR (500 MHz, DMSO-d6) δ: 8.93 (s, 1H); 8.66 (d, J=5.1 Hz, 1H); 8.37 (s, 1H); 8.13 (s, 1H); 7.95 (dd, J=1.3, 5.1 Hz, 1H); 7.58 (d, J=8.7 Hz, 1H); 7.42 (d, J=8.7 Hz, 1H); 4.84 (m, 1H); 4.60 (s, 2H); 4.39 (t, J=5.8 Hz, 2H); 4.23 (m, 1H); 3.91 (s, 2H); 3.77 (dd, J=7.4, 10.0 Hz, 1H); 2.95 (t, J=5.0 Hz, 2H); 2.69 (d, J=3.5 Hz, 2H); 2.02-1.85 (m, 2H).

    [1447] MS3 (ESI, m/z): 507.09 [M+H.sup.+]; t.sub.R=0.47 min.

    Example $159

    6-[(S)-5-(2-{[5-(2-amino-ethoxy)-[3,4]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $159.i. {2-[2′-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-[3,4′ ]bipyridinyl-5-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1448] Starting from the compound of Preparation C55 (80 mg) and the compound of Preparation D1 (65 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as an orange solid (58 mg; 41% yield).

    [1449] MS3 (ESI, m/z): 605.15 [M+H.sup.+]; t.sub.R=0.64 min.

    $159.ii. 6-[(S)-5-(2-{[5-(2-amino-ethoxy)-[3,4′]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1450] Starting from intermediate $159.i (51 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained after purification by prep-HPLC (method 2) as an off-white solid (23 mg; 54% yield).

    [1451] MS3 (ESI, m/z): 506.09 [M+H.sup.+]; t.sub.R=0.46 min.

    Example $160

    6-[(S)-5-(2-{3-[2-(2-amino-ethoxy)-pyrimidin-4-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $160.i. (2-{4-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-y]-ethylamino}-methyl)-phenyl]-pyrimidin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1452] Starting from the compound of Preparation C56 (50 mg) and the compound of Preparation D1 (43 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (45 mg; 51% yield).

    [1453] MS3 (ESI, m/z): 606.16 [M+H.sup.+]; t.sub.R=0.69 min.

    $160.ii. 6-[(S)-5-(2-{3-[2-(2-amino-ethoxy)-pyrimidin-4-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1454] Starting from intermediate $160.i (31 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a yellowish solid (31 mg; 93% yield).

    [1455] MS3 (ESI, m/z): 506.11 [M+H.sup.+]; t.sub.R=0.49 min.

    Example $161

    6-[(S)-5-(2-{3-[4-(2-amino-ethoxy)-6-methoxy-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $161.i. (2-{2-methoxy-6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-4-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1456] Starting from the compound of Preparation C57 (55 mg) and the compound of Preparation D1 (35 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 19:1), as a beige foam (29 mg; 39% yield).

    [1457] MS3 (ESI, m/z): 635.16 [M+H.sup.+]; t.sub.R=0.74 min.

    $161.ii. 6-[(S)-5-(2-{3-[4-(2-amino-ethoxy)-6-methoxy-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1458] Starting from intermediate $161.i (25 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (20 mg; 95% yield).

    [1459] MS3 (ESI, m/z): 535.12 [M+H.sup.+]; t.sub.R=0.53 min.

    Example $162

    6-[(S)-5-(2-{[4-(2-amino-ethoxy)-6-methoxy-[2,4]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $162.i. {2-[6-methoxy-2′-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-[2,4′]bipyridinyl-4-yloxy]-ethyl}-carbamic acid tert-butyl ester

    [1460] Starting from the compound of Preparation C58 (25 mg) and the compound of Preparation D1 (20 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 19:1), as an off-white foam (25 mg; 59% yield).

    [1461] MS3 (ESI, m/z): 636.16 [M+H.sup.+]; t.sub.R=0.73 min.

    $162.ii. 6-[(S)-5-(2-{[4-(2-amino-ethoxy)-6-methoxy-[2,4′]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1462] Starting from intermediate $162.i (22 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (13 mg; 70% yield).

    [1463] MS3 (ESI, m/z): 536.16 [M+H.sup.+]; t.sub.R=0.51 min.

    Example $163

    6-[(S)-5-(2-{3-[6-(2-methylamino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $163.i. Methyl-(2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1464] Starting from the compound of Preparation C59 (70 mg) and the compound of Preparation D1 (57 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by CC (Combiflash; DCM to DCM/MeOH 9:1), as an off-white foam (67 mg; 55% yield).

    [1465] MS3 (ESI, m/z): 619.12 [M+H.sup.+]; t.sub.R=0.77 min.

    $163.ii. 6-[(S)-5-(2-{3-[6-(2-methylamino-ethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1466] Starting from intermediate $163.i (60 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (41 mg; 82% yield).

    [1467] MS3 (ESI, m/z): 520.11 [M+H.sup.+]; t.sub.R=0.50 min.

    Example $164

    6-[(S)-5-(2-{3-[6-(2-methylamino-ethoxy)-pyrazin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $164.i. Methyl-(2-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyrazin-2-yloxy}-ethyl)-carbamic acid tert-butyl ester

    [1468] Starting from the compound of Preparation C60 (70 mg) and the compound of Preparation D1 (57 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained after purification by CC (Combiflash; DCM to DCM/MeOH 9:1) as a yellowish oil (69 mg; 57% yield).

    [1469] MS3 (ESI, m/z): 620.11 [M+H.sup.+]; t.sub.R=0.74 min.

    $164.ii. 6-[(S)-5-(2-{3-[6-(2-methylamino-ethoxy)-pyrazin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1470] Starting from intermediate $164.i (60 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (31 mg; 62% yield).

    [1471] MS3 (ESI, m/z): 519.10 [M+H.sup.+]; t.sub.R=0.53 min.

    Example $165

    6-{(S)-5-[2-({4-[6-(2-amino-ethoxy)-pyridin-2-yl]-pyrimidin-2-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $165.i. Tert-butyl (S)-(2-((6-(2-(((2-(2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)pyrimidin-4-yl)pyridin-2-yl)oxy)ethyl)carbamate

    [1472] The compound of Preparation C61 (20 mg) and the compound of Preparation D1 (16 mg) were dissolved in a 1/1 DMF/DCM mixture (2 mL). NaBH(OAc).sub.3 (44 mg) was added. The reaction mixture was stirred at rt for 1 h and the solvents were then evaporated. The residue was dissolved in EA and the mixture was washed with sat. aq. NaHCO.sub.3. The org. layers was separated, dried over Na.sub.2SO.sub.4 and evaporated. The title compound was obtained, after purification by CC (EA, then EA/MeOH 9/1), as a colourless solid (12 mg; 34% yield).

    [1473] .sup.1H NMR (300 MHz, CDCl.sub.3) δ: 1.44 (s, 9H); 1.98-1.86 (m, 2H); 2.18-2.01 (m, 1H); 2.97 (t, J=6.7 Hz, 2H); 3.59 (dd, J=11.1, 5.7 Hz, 2H); 3.81 (dd, J=10.2, 7.5 Hz, 1H); 4.14 (s, 2H); 4.26 (dd, J=10.5, 8.4 Hz, 1H); 4.51 (t, J=5.4 Hz, 1H); 4.63 (s, 2H); 4.88-4.79 (m, 1H); 5.06 (br. s, 1H); 6.87 (d, J=8.4 Hz, 1H); 7.30 (d, J=9.0 Hz, 1H); 7.75 (t, J=7.8 Hz, 1H); 7.82 (d, J=8.7 Hz, 1H); 8.15 (d, J=6.9 Hz, 1H); 8.80 (d, J=5.4 Hz, 1H).

    [1474] MS3 (ESI, m/z): 607.10 [M+H.sup.+]; t.sub.R=0.70 min.

    $165.ii. 6-{(S)-5-[2-({4-[6-(2-amino-ethoxy)-pyridin-2-yl]-pyrimidin-2-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1475] Starting from intermediate $165.i (10 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (31 mg; 62% yield).

    [1476] MS3 (ESI, m/z): 507.03 [M+H.sup.+]; t.sub.R=0.48 min.

    Example $166

    6-[(S)-5-(2-{3-[5-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1477] Starting from the compound of Preparation C62 (107 mg) and the compound of Preparation D1 (105 mg) and proceeding in analogy to Example $102, step $102.i, however using a 4/1 DCM/MeOH mixture as solvent and performing the reaction in the presence of AcOH (0.022 mL), the title compound was obtained, after purification by CC (DCM to DCM/MeOH/NH.sub.4OH 9:1:0.05), as a colourless solid (41 mg; 20% yield).

    [1478] MS1 (ESI, m/z): 545.79 [M+H.sup.+]; t.sub.R=0.48 min.

    Example $167

    6-[(S)-5-(2-{3-[6-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

    [1479] Starting from the compound of Preparation C21 (60 mg) and 6-[(S)-5-(2-amino-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one (62 mg; prepared according to WO 2010/041194) and proceeding in analogy to Example $102, step $102.i, however using a 2/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (3.6 mg; 3% yield).

    [1480] MS3 (ESI, m/z): 560.10 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $168

    6-[(S)-5-(2-{3-[6-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

    [1481] Starting from the compound of Preparation C20 (60 mg) and 6-[(S)-5-(2-amino-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one (62 mg; prepared according to WO 2010/041194) and proceeding in analogy to Example $102, step $102.i, however using a 2/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (16 mg; 14% yield).

    [1482] MS3 (ESI, m/z): 560.11 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $169

    6-[(R)-5-(2-{3-[6-((R)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-benzo[1,4]thiazin-3-one

    [1483] Starting from the compound of Preparation C20 (60 mg) and 6-[(5R)-5-(2-aminoethyl)-2-oxo-3-oxazolidinyl]-2H-1,4-benzothiazin-3(4H)-one (42 mg; prepared according to WO 2010/041219) and proceeding in analogy to Example $102, step $102.i, however using a 2/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (3.3 mg; 3% yield).

    [1484] MS3 (ESI, m/z): 560.12 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $170

    6-[(S)-5-(2-{3-[6-methoxy-4-((S)-1-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1485] Starting from the compound of Preparation C63 (30 mg) and the compound of Preparation D1 (28 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained after purification by prep-HPLC (method 2) as a colourless solid (19 mg; 34% yield).

    [1486] .sup.1H NMR (500 MHz, DMSO-d6) δ: 8.02 (s, 1H); 7.94 (dt, J=6.9, 1.8 Hz, 1H); 7.59 (m, 1H); 7.43-7.37 (m, 3H); 7.08 (d, J=1.9 Hz, 1H); 6.23 (d, J=1.8 Hz, 1H); 5.04-5.01 (m, 1H); 4.81 (m, 1H); 4.61 (s, 2H); 4.22 (m, 1H); 3.93 (s, 3H); 3.78 (s, 2H); 3.76-3.74 (m, 1H); 2.77 (dd, J=10.6, 6.0 Hz, 1H); 2.70-2.62 (m, 4H); 2.36-2.31 (m, 2H); 2.26 (s, 3H); 1.92 (m, 2H); 1.81-1.76 (m, 1H).

    [1487] MS3 (ESI, m/z): 575.14 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $171

    6-[(S)-5-(2-{3-[6-((R)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1488] Starting from the compound of Preparation C.sub.64 (80 mg) and the compound of Preparation D1 (76 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained after purification by prep-HPLC (method 2) as a colourless solid (59 mg; 41% yield).

    [1489] MS3 (ESI, m/z): 559.13 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $172

    6-[(S)-5-(2-{3-[6-((2S*,3S*)-2-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $172.1. Tert-butyl (2S*,3S*)-2-methyl-3-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-pyrrolidine-1-carboxylate

    [1490] Starting from the compound of Preparation C.sub.65 (110 mg) and the compound of Preparation D1 (59 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained after purification by CC (Combiflash; DCM to DCM/MeOH 4:1) as a yellowish oil (88 mg; 68% yield).

    [1491] MS3 (ESI, m/z): 645.13 [M+H.sup.+]; t.sub.R=0.79 min.

    $1 72.ii. 6-[(S)-5-(2-{3-[-6-((2S*,3S*)-2-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1, 4]oxazin-3-one

    [1492] Starting from intermediate $172.i (82 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (21 mg; 40% yield).

    [1493] MS3 (ESI, m/z): 545.03 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $173

    6-[(S)-5-(2-{3-[6-((3S*,4R*)-4-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $1 73.i. (3R*,4S*)-3-methyl-4-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1494] Starting from the compound of Preparation C.sub.66 (100 mg) and the compound of Preparation D1 (74 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained after purification by CC (Combiflash; DCM to DCM/MeOH 4:1) as a yellowish oil (72 mg; 44% yield).

    [1495] MS3 (ESI, m/z): 645.13 [M+H.sup.+]; t.sub.R=0.80 min.

    $173. ii. 6-[(S)-5-(2-{3-[6-((3S*,4R*)-4-methyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1496] Starting from intermediate $173.i (65 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (35 mg; 64% yield).

    [1497] MS3 (ESI, m/z): 545.05 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $174

    6-[(S)-5-(2-{3-[5-(1-methyl-azetidin-3-yloxy)-pyridazin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1498] Starting from the compound of Preparation C.sub.67 (111 mg) and the compound of Preparation D1 (115 mg) and proceeding in analogy to Example $102, step $102.i, however using a 4/1 DCM/MeOH mixture as solvent and performing the reaction in the presence of AcOH (0.024 mL), the title compound was obtained, after purification by CC (DCM to DCM/MeOH/NH.sub.4OH 9:1:0.05), as a colourless solid (41 mg; 19% yield). MS1 (ESI, m/z): 532.07 [M+H.sup.+]; t.sub.R=0.47 min.

    Example $175

    6-[(S)-5-(2-{3-[6-((3S,5S)-1,5-dimethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1499] Starting from the compound of Preparation C.sub.68 (60 mg) and the compound of Preparation D1 (59 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (59 mg; 52% yield).

    [1500] MS3 (ESI, m/z): 559.13 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $176

    6-[(S)-5-(2-{3-[6-((2S*,3S*)-1,2-dimethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1501] Starting from the compound of Preparation C.sub.69 (60 mg) and the compound of Preparation D1 (59 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained after purification by prep-HPLC (method 2) as a light yellow solid (53 mg; 47% yield).

    [1502] MS3 (ESI, m/z): 559.13 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $177

    6-[(S)-5-(2-{3-[6-((3S*,4R*)-1,4-dimethyl-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1503] Starting from the compound of Preparation C.sub.70 (45 mg) and the compound of Preparation D1 (40 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (31 mg; 41% yield).

    [1504] MS3 (ESI, m/z): 559.12 [M+H.sup.+]; t.sub.R=0.56 min.

    Example $178

    6-[(S)-5-(2-{3-[6-((2RS,3RS)-1,2-dimethyl-azetidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1505] Starting from the compound of Preparation C71 (28 mg) and the compound of Preparation D1 (29 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (21 mg; 39% yield).

    [1506] MS3 (ESI, m/z): 545.07 [M+H.sup.+]; t.sub.R=0.55 min.

    Example $179

    6-{(S)-5-[2-({6-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridin-2-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1507] Starting from the compound of Preparation C.sub.72 (13 mg) and the compound of Preparation D1 (14 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (9 mg; 35% yield).

    [1508] MS3 (ESI, m/z): 533.13 [M+H.sup.+]; t.sub.R=0.48 min.

    Example $180

    6-[(S)-2-oxo-5-(2-{3-[54-((R)-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $180.1. Tert-butyl (R)-3-((6-(3-(((2-((S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)phenyl)pyridazin-4-yl)oxy)pyrrolidine-1-carboxylate

    [1509] Starting from the compound of Preparation C.sub.73 (152 mg) and the compound of Preparation D1 (115 mg) and proceeding in analogy to Example $102, step $102.i, however using a 4/1 DCM/MeOH mixture as solvent and performing the reaction in the presence of AcOH (0.024 mL), the title compound was obtained after purification by CC (DCM to DCM/MeOH/NH.sub.4OH 9:1:0.1) as a yellow sticky oil (200 mg; 77% yield).

    [1510] MS1 (ESI, m/z): 632.07 [M+H.sup.+]; t.sub.R=0.69 min.

    $180.ii. 6-[(S)-2-oxo-5-(2-{3-[5-((R)-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1511] Starting from intermediate $180.i (200 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 4), as a colourless solid (35 mg; 64% yield).

    [1512] MS1 (ESI, m/z): 532.08 [M+H.sup.+]; t.sub.R=0.48 min.

    Example $181

    6-[(S)-2-oxo-5-(2-{3-[5-((S)-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $181.i. Tert-butyl (S)-3-((6-(3-(((2-((S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)phenyl)pyridazin-4-ypoxy)pyrrolidine-1-carboxylate

    [1513] Starting from the compound of Preparation C74 (152 mg) and the compound of Preparation D1 (115 mg) and proceeding in analogy to Example $102, step $102.i, however using a 4/1 DCM/MeOH mixture as solvent and performing the reaction in the presence of AcOH (0.024 mL), the title compound was obtained, after purification by CC (DCM to DCM/MeOH/NH.sub.4OH 9:1:0.05), as a brown sticky oil (138 mg; 53% yield).

    [1514] MS1 (ESI, m/z): 632.11 [M+H.sup.+]; t.sub.R=0.70 min.

    $181.ii. 6-[(S)-2-oxo-5-(2-{3-[5-((S)-pyrrolidin-3-yloxy)-pyridazin-3-yl]-benzylamino}-ethyl)-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1515] Starting from intermediate $181.i (138 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 4), as a light brown solid (100 mg; 86% yield).

    [1516] MS1 (ESI, m/z): 532.02 [M+H.sup.+]; t.sub.R=0.48 min.

    Example $182

    6-[(S)-5-(2-{3-[5-((S)-1-azetidin-2-ylmethoxy)-pyridazin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $182.i. Tert-butyl (S)-2-(((6-(3-(((2-((S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)phenyl)pyridazin-4-yl)oxy)methypazetidine-1-carboxylate

    [1517] Starting from the compound of Preparation C.sub.75 (152 mg) and the compound of Preparation D1 (115 mg) and proceeding in analogy to Example $102, step $102.i, however using a 4/1 DCM/MeOH mixture as solvent and performing the reaction in the presence of AcOH (0.024 mL), the title compound was obtained after purification by CC (DCM to DCM/MeOH/NH.sub.4OH 9:1:0.05) as a brown sticky oil (125 mg; 48% yield).

    [1518] MS1 (ESI, m/z): 632.13 [M+H.sup.+]; t.sub.R=0.69 min.

    $182.ii. 6-[(S)-5-(2-{3-[5-((S)-1-azetidin-2-ylmethoxy)-pyridazin-3-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1519] Starting from intermediate $182.i (125 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 4), as a light brown solid (18 mg; 17% yield).

    [1520] MS1 (ESI, m/z): 531.99 [M+H.sup.+]; t.sub.R=0.49 min.

    Example 183

    6-[(S)-5-(2-{[3-((1S,3R)-3-amino-cyclopentyloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $183.i. Tert-butyl ((1S,3R)-3-((3′-(((2-((S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)oxazolidin-5-yl)ethyl)amino)methyl)-[1,1′-biphenyl]-3-ypoxy)cyclopentyl)carbamate

    [1521] Starting from the compound of Preparation A22 (169 mg) and the compound of Preparation D1 (80 mg) and proceeding in analogy to Example 1, step 1.i, the title compound was obtained as an off-white oil (107 mg; 58% yield).

    [1522] MS3 (ESI, m/z): 644.01 [M+H.sup.+]; t.sub.R=0.79 min.

    $183.ii. 6-[(S)-5-(2-{[3′-((1S,3R)-3-amino-cyclopentyloxy)-biphenyl-3-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1523] Starting from intermediate $183.i (101 mg) and proceeding in analogy to Example 1, step 1.ii, the title compound was obtained as a colourless solid (50 mg; 59% yield).

    [1524] MS3 (ESI, m/z): 544.09 [M+H.sup.+]; t.sub.R=0.57 min.

    Example $184

    (3R*,4S*)-6-[(S)-5-(2-{3-[6-(4-methoxy-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    $184.i. (3R*,4S*)-3-methoxy-4-{6-[3-({2-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl) -oxazolidin-5-yl]-ethylamino}-methyl)-phenyl]-pyridin-2-yloxy}-pyrrolidine-1-carboxylic acid tert-butyl ester

    [1525] Starting from the compound of Preparation C.sub.12 (60 mg) and the compound of Preparation D1 (44 mg) and proceeding in analogy to Example $102, step $102.i, the title compound was obtained, after purification by CC (Combiflash; gradient DCM to DCM/MeOH 9:1), as a yellowish oil (65 mg; 65% yield).

    [1526] MS3 (ESI, m/z): 661.99 [M+H.sup.+]; t.sub.R=0.75 min.

    $184.ii. (3R*,4S*)-6-[(S)-5-(2-{3-[6-(4-methoxy-pyrrolidin-3-yloxy)-pyridin-2-yl]-benzylamino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1527] Starting from intermediate $184.i (112 mg) and proceeding in analogy to Example $102, step $102.ii, the title compound was obtained, after purification by prep-HPLC (method 2), as a yellowish solid (31 mg; 61% yield).

    [1528] MS3 (ESI, m/z): 561.04 [M+H+]; t.sub.R=0.52 min.

    Example $185

    6-[(S)-5-(2-{[6′-(1-methyl-azetidin-3-yloxy)-[2,2]bipyridinyl-4-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1529] Starting from the compound of Preparation C.sub.76 (21 mg) and the compound of Preparation D1 (23 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a yellowish solid (11 mg; 27% yield).

    [1530] MS3 (ESI, m/z): 532.15 [M+H+]; t.sub.R=0.51 min.

    Example $186

    6-[(S)-5-(2-{[6-(1-methyl-azetidin-3-yloxy)-[2,4]bipyridinyl-2′-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1531] Starting from the compound of Preparation C.sub.77 (60 mg) and the compound of Preparation D1 (65 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (18 mg; 15% yield).

    [1532] MS3 (ESI, m/z): 532.15 [M+H+]; t.sub.R=0.52 min.

    Example $187

    6-{(S)-5-[2-({4-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridin-2-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1533] Starting from the compound of Preparation C.sub.78 (24 mg) and the compound of Preparation D1 (26 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (14 mg; 30% yield).

    [1534] MS3 (ESI, m/z): 533.15 [M+H+]; t.sub.R=0.48 min.

    Example $188

    6-[(S)-5-(2-{[6′-(1-methyl-azetidin-3-yloxy)-[2,2]bipyridinyl-6-ylmethyl]-amino}-ethyl)-2-oxo-oxazolidin-3-yl]-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1535] Starting from the compound of Preparation C.sub.79 (16 mg) and the compound of Preparation D1 (17 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (9 mg; 29% yield).

    [1536] MS3 (ESI, m/z): 532.13 [M+H+]; t.sub.R=0.52 min.

    Example $189

    6-{(S)-5-[2-({2-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridin-4-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1537] Starting from the compound of Preparation C.sub.80 (11 mg) and the compound of Preparation D1 (12 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a colourless solid (3 mg; 14% yield).

    [1538] MS3 (ESI, m/z): 533.14 [M+H+]; t.sub.R=0.48 min.

    Example $190

    6-{(S)-5-[2-({5-[6-(1-methyl-azetidin-3-yloxy)-pyrazin-2-yl]-pyridin-3-ylmethyl}-amino)-ethyl]-2-oxo-oxazolidin-3-yl}-4H-pyrido[3,2-b][1,4]oxazin-3-one

    [1539] Starting from the compound of Preparation C.sub.81 (80 mg) and the compound of Preparation D1 (87 mg) and proceeding in analogy to Example $102, step $102.i, however using a 1/1 DCM/MeOH mixture as solvent, the title compound was obtained, after purification by prep-HPLC (method 2), as a light yellow solid (41 mg; 26% yield).

    [1540] MS3 (ESI, m/z): 533.14 [M+H+]; t.sub.R=0.47 min.

    [1541] Pharmacological properties of the invention compounds

    [1542] In Vitro Assays

    [1543] Bacterial Growth Minimal Inhibitory Concentrations:

    [1544] Experimental Methods:

    [1545] Minimal Inhibitory Concentrations (MICs; mg/L) were determined in cation-adjusted Mueller-Hinton Broth by a microdilution method following the description given in “Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically”, Approved standard, 7.sup.th ed., Clinical and Laboratory Standards Institute (CLSI) Document M7-A7, Wayne, Pa., USA (2006).

    [1546] Results:

    [1547] All Example compounds were tested against several Gram positive and Gram negative bacteria. Typical antibacterial test results are given in Table 1 hereafter (MICs in mg/L). Staphylococcus aureus A798 is a multiply-resistant strain (methicillin- and quinolone-resistant), Klebsiella pneumoniae T6474 is a multiply-resistant strain (penicillin-, cephalosporin- and in particular quinolone-resistant), while E. coli ATCC.sub.25922 and Pseudomonas aeruginosa ATCC 27853 are quinolone-sensitive strains.

    TABLE-US-00001 TABLE 1 MIC for MIC for MIC for MIC for Example S. aureus E. coli K. pneumoniae P. aeruginosa No. A798 ATCC25922 T6474 ATCC 27853 1 2 1 1 2 2 0.5 2 2 4 3 2 1 2 2 4 2 1 2 2 5 2 4 4 4 6 4 4 4 4 8 0.25 0.5 1 0.25 9 0.125 2 1 2 10 8 2 4 4 11 2 2 4 1 12 0.063 1 2 2 13 0.5 2 2 8 14 1 2 2 8 15 0.5 1 2 1 16 0.5 2 4 0.5 17 0.5 1 2 1 18 0.5 1 2 1 19 8 1 4 1 20 0.5 2 8 2 21 0.5 1 2 1 22 0.5 0.5 2 0.5 23 0.125 4 8 8 $101 2 1 2 1 $102 2 1 2 2 $103 2 1 1 1 $104 1 2 4 4 $105 2 2 2 2 $106 2 2 4 1 $107 1 0.5 2 0.5 $108 2 1 2 0.5 $109 0.5 1 2 1 $110 0.25 1 2 2 $111 1 2 2 2 $113 0.5 2 2 2 $114 16 4 8 1 $115 4 4 16 2 $116 4 2 8 2 $117 1 1 1 4 $118 2 1 2 1 $119 0.5 1 1 0.5 $120 0.5 1 2 2 $121 0.25 0.5 0.5 1 $122 0.25 0.25 0.5 0.5 $123 0.25 1 1 1 $124 1 1 2 0.5 $125 0.5 1 2 4 $126 0.5 1 2 2 $127 1 2 8 4 $128 0.25 0.5 1 1 $129 2 4 4 8 $130 0.25 1 2 4 $131 0.25 0.5 1 0.5 $132 0.25 0.5 1 0.5 $133 1 1 2 0.5 $134 0.5 2 4 4 $135 0.5 0.5 1 0.5 $136 0.25 1 2 2 $137 0.5 1 1 1 $138 2 1 2 2 $139 0.25 1 1 2 $140 0.5 2 2 2 $141 0.5 2 2 2 $142 0.5 2 2 2 $143 2 2 4 1 $144 2 4 4 1 $145 2 4 2 8 $146 4 2 4 4 $147 1 1 1 4 $148 1 1 1 1 $149 0.5 0.5 1 1 $150 2 2 2 2 $151 4 2 2 1 $152 4 2 4 1 $153 4 2 4 4 $154 4 1 4 0.5 $155 1 2 16 2 $156 1 1 2 0.5 $157 8 4 16 1 $158 4 8 16 2 $159 8 16 8 4 $160 4 2 8 1 $161 0.5 0.5 1 1 $162 1 1 1 1 $163 0.5 0.5 2 0.5 $164 0.5 1 1 0.5 $165 8 4 4 2 $166 4 2 4 4 $167 0.25 1 1 1 $168 1 2 2 2 $169 0.25 1 2 2 $170 0.25 2 4 2 $171 0.25 1 1 1 $172 0.5 1 2 0.5 $173 0.5 1 2 1 $174 2 1 2 2 $175 0.25 2 4 4 $176 0.25 2 2 2 $177 0.5 2 4 4 $178 0.125 0.5 1 1 $179 0.5 1 1 2 $180 >16 16 >16 4 $181 16 16 >16 4 $182 8 16 16 16 $183 2 4 4 4 $184 8 4 8 2 $185 0.125 0.5 0.5 1 $186 0.25 0.5 1 0.5 $187 0.5 0.5 1 0.5 $188 1 1 2 4 $189 0.25 1 1 2 $190 4 2 4 4 Cipro >8 ≦0.016 >8 0.25