Provided is a method for purifying waste N-methyl-2-pyrrolidone, the method comprising the steps of: reacting the waste N-methyl-2-pyrrolidone containing an amine compound with an acid anhydride; converting the amine compound into an amide compound; and removing the amide compound by distillation, thereby manufacturing high-purity N-methyl-2-pyrrolidone that can be reused.

Provided is a method for purifying waste N-methyl-2-pyrrolidone, the method comprising the steps of: reacting the waste N-methyl-2-pyrrolidone containing an amine compound with an acid anhydride; converting the amine compound into an amide compound; and removing the amide compound by distillation, thereby manufacturing high-purity N-methyl-2-pyrrolidone that can be reused.

An electrode current collector including a metal foil wherein a coating layer is formed on one or both surfaces of the metal foil, and a contact angle with pure water of the surface of the coating layer at a side opposite to the metal foil side is 30° or more.

The invention relates to a new process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a γ-amino-δ-biphenyl-α-methylalkanoic acid, or acid ester, backbone, such as N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester or salt thereof.

The invention relates to a new process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a γ-amino-δ-biphenyl-α-methylalkanoic acid, or acid ester, backbone, such as N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester or salt thereof.

This application discloses a novel process to synthesize 8-[{1-(3,5-Bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds, which may be used, for example, as NK-1 inhibitor compounds in pharmaceutical preparations, intermediates useful in said process, and processes for preparing said intermediates; also disclosed is a process for removal of metals from N-heterocyclic carbine metal complexes.

This application discloses a novel process to synthesize 8-[{1-(3,5-Bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds, which may be used, for example, as NK-1 inhibitor compounds in pharmaceutical preparations, intermediates useful in said process, and processes for preparing said intermediates; also disclosed is a process for removal of metals from N-heterocyclic carbine metal complexes.

A paroxetine intermediate, a method for preparing the same, and uses thereof are provided. Specifically, the method includes: reacting a compound of formula I below with a compound of formula II in the presence of air organic base under the catalysis of a complex formed from a chiral amine oxide L and a rare-earth metal compound Ln(OTf).sub.3 to prepare a compound of formula III below: wherein R.sub.1 is alkyl, phenyl or benzyl; R.sub.2, R.sub.3, R.sub.4 are each independently C.sub.1-C.sub.6 alkyl or C.sub.6-C.sub.10 aryl; the chiral amine oxide L has the following structure: wherein n=1, 2; and R=Ph-, 2,6-Me.sub.2C.sub.6H.sub.3-, 2,6-Et.sub.2C.sub.6H.sub.3-, 2,6-iPr.sub.2C.sub.6H.sub.3-, Ph.sub.2CH—.

##STR00001##

The N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein n is 1 or 2; L represents a C.sub.1-3alkyl linker optionally substituted with one or two substituents selected from C.sub.1-4alkyl, C.sub.1-3alkyloxy-C.sub.1-4alkyl-, hydroxy-C.sub.1-4alkyl, hydroxy, C.sub.1-3alkyloxy- or phenyl-C.sub.1-4alkyl; M represents a direct bond or a C.sub.1-3alkyl linker optionally substituted with one or two substituents selected from hydroxy, C.sub.1-4alkyl or C.sub.1-4alkyloxy; R.sup.1 and R.sup.2 each independently represent hydrogen, halo, cyano, hydroxy, C.sub.1-4alkyl optionally substituted with halo, C.sub.1-4alkyloxy- optionally substituted with one or where possible two or three substituents selected from hydroxy, Ar.sup.1 and halo; or R.sup.1 and R.sup.2 taken together with the phenyl ring to which they are attached form naphtyl or 1,3-benzodioxolyl, wherein said naphtyl or 1,3-benzodioxolyl are optionally substituted with halo; R.sup.3 represents hydrogen, halo, C.sub.1-4alkyl, C.sub.1-4alkyloxy-, cyano or hydroxy; R.sup.4 represents hydrogen, halo, C.sub.1-4alkyl, C.sub.1-4alkyloxy-, cyano or hydroxy; R.sup.5 represents hydrogen, C.sub.1-4alkyl or Ar.sup.2—C.sub.1-4alkyl-; R.sup.6 represents hydrogen, halo, C.sub.1-4alkyl or C.sub.1-4alkyoxy-; Ar.sup.1 and Ar.sup.2 each independently represent phenyl or naphtyl wherein said phenyl and naphtyl are optionally substituted with C.sub.1-4alkyl, C.sub.1-4alkyloxy-, or phenyl-C.sub.1-4alkyl;
for use as a medicine. ##STR00001##

The N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein n is 1 or 2; L represents a C.sub.1-3alkyl linker optionally substituted with one or two substituents selected from C.sub.1-4alkyl, C.sub.1-3alkyloxy-C.sub.1-4alkyl-, hydroxy-C.sub.1-4alkyl, hydroxy, C.sub.1-3alkyloxy- or phenyl-C.sub.1-4alkyl; M represents a direct bond or a C.sub.1-3alkyl linker optionally substituted with one or two substituents selected from hydroxy, C.sub.1-4alkyl or C.sub.1-4alkyloxy; R.sup.1 and R.sup.2 each independently represent hydrogen, halo, cyano, hydroxy, C.sub.1-4alkyl optionally substituted with halo, C.sub.1-4alkyloxy- optionally substituted with one or where possible two or three substituents selected from hydroxy, Ar.sup.1 and halo; or R.sup.1 and R.sup.2 taken together with the phenyl ring to which they are attached form naphtyl or 1,3-benzodioxolyl, wherein said naphtyl or 1,3-benzodioxolyl are optionally substituted with halo; R.sup.3 represents hydrogen, halo, C.sub.1-4alkyl, C.sub.1-4alkyloxy-, cyano or hydroxy; R.sup.4 represents hydrogen, halo, C.sub.1-4alkyl, C.sub.1-4alkyloxy-, cyano or hydroxy; R.sup.5 represents hydrogen, C.sub.1-4alkyl or Ar.sup.2—C.sub.1-4alkyl-; R.sup.6 represents hydrogen, halo, C.sub.1-4alkyl or C.sub.1-4alkyoxy-; Ar.sup.1 and Ar.sup.2 each independently represent phenyl or naphtyl wherein said phenyl and naphtyl are optionally substituted with C.sub.1-4alkyl, C.sub.1-4alkyloxy-, or phenyl-C.sub.1-4alkyl;
for use as a medicine. ##STR00001##