Abstract
The invention belongs to the technical field of pesticides, and specifically relates to a 4-pyridinyl formamide compound or a derivative thereof, a preparation method therefor, a herbicidal composition and the use thereof. The 4-pyridinyl formamide compound is as represented by formula (I), wherein, X and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto, etc.; and M represents an unsubstituted or substituted structure (II). The compound, and the derivative and the composition thereof have excellent herbicidal activity and a higher crop safety, and establish good selectivity, especially for key crops such as wheat and rice.
##STR00001##
Claims
1. A 4-pyridinyl formamide compound or derivative thereof, as shown in Formula I: ##STR04414## Wherein, X, and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, which is with or without halogen; OR.sup.1, COR.sup.1, COOR.sup.1, OCOR.sup.1, OCOOR.sup.1, NR.sup.3SO.sub.2R.sup.2, OSO.sub.2R.sup.2, S(O).sub.mR.sup.2, NR.sup.3COR.sup.1, NR.sup.3COOR.sup.1, C(O)NR.sup.3OR.sup.1, SO.sub.2OR.sup.1, C(O)NR.sup.4R.sup.5, NR.sup.3C(O)NR.sup.4R.sup.5, OC(O)NR.sup.4R.sup.5, SO.sub.2NR.sup.4R.sup.5, C(S)R.sup.1, C(S)OR.sup.1, C(S)SR.sup.2, C(O)SR.sup.2, SC(O)R.sup.1, SC(S)R.sup.1, OC(S)R.sup.1, -alkyl-C(S)R.sup.1, -alkyl-C(S)OR.sup.1, -alkyl-C(O)SR.sup.1, -alkyl-C(S)SR.sup.1, -alkyl-SC(O)R.sup.1, -alkyl-OC(S)R.sup.1, -alkyl-SC(S)R.sup.1, —O-alkyl-NR.sup.4R.sup.5, —S-alkyl-NR.sup.4R.sup.5, -alkyl-O-alkyl-NR.sup.4R.sup.5, -alkyl-S-alkyl-NR.sup.4R.sup.5, -alkyl-(C═S)n-NR.sup.4R.sup.5, —NH-alkyl-NR.sup.4R.sup.5, -alkyl-OR.sup.1, -alkyl-COR.sup.1, -alkyl-CO.sub.2R.sup.1, -alkyl-OCOR.sup.1, -alkyl-NR.sup.3COR.sup.1, -alkyl-SO.sub.2OR.sup.1, -alkyl-NR.sup.3SQ.sub.2R.sup.2, -alkyl-OSO.sub.2R.sup.2, -alkyl-S(O).sub.mR.sup.2, -alkyl-CONR.sup.4R.sup.5, -alkyl-SO.sub.2NR.sup.4R.sup.5, NR.sup.4R.sup.5, ##STR04415## P(O)(OR.sup.6).sub.2, CH.sub.2P(O)(OR.sup.6).sub.2, SO.sub.2NR.sup.4R.sup.5-alkyl-S(O).sub.mR.sup.2, -alkyl-CN, -alkylaryl, -alkylheteroaryl, -alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl; R.sup.1, R.sup.3, R.sup.4, and R.sup.5 each independently represent hydrogen, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, halogenated alkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkyl, halogenated cycloalkyl, alkoxyalkyl, or cycloalkylalkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR.sup.7, S(O).sub.mR.sup.9, NR.sup.7R.sup.8, NR.sup.8OR.sup.7, COR.sup.7, OCOR.sup.7, SCOR.sup.7, NR.sup.8COR.sup.7, CO.sub.2R.sup.7, COSR.sup.7, CONR.sup.7R.sup.8, and alkoxyalkoxycarbonyl; R.sup.2 represents aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR.sup.7, S(O).sub.mR.sup.9, NR.sup.7R.sup.8, NR.sup.8OR.sup.7, COR.sup.7, OCOR.sup.7, SCOR.sup.7, NR.sup.8COR.sup.7, CO.sub.2R.sup.7, COSR.sup.7, CONR.sup.7R.sup.8, and alkoxyalkoxycarbonyl; R.sup.6 represents methyl, or ethyl; R.sup.7, and R.sup.8 each independently represent hydrogen, alkyl, alkenyl, or alkynyl; R.sup.9 represents alkyl, alkenyl, or alkynyl; M represents ##STR04416## which is unsubstituted or substituted; R.sub.11 represents hydrogen, halogen, cyano, nitro, alkyl which is unsubstituted or substituted with a substituent selected from R.sub.13, cycloalkyl which is unsubstituted or substituted with a substituent selected from R.sub.14, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, NH.sub.2, aminoacyl, carboxyl, alkoxyalkoxycarbonyl, OR.sub.15, -alkyl-OR.sub.15, C(O)R.sub.16, -alkyl-C(O)R.sub.16, C(O)OR.sub.16, -alkyl-C(O)OR.sub.16, S(O).sub.mR.sub.16, -alkyl-S(O).sub.mR.sub.16, —N(R.sub.16).sub.2, —NHR.sub.16, —C(O)NHR.sub.16, —C(O)N(R.sub.16).sub.2, —NHC(O)R.sub.17, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, arylalkyl, aryloxy, arylcarbonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, or heteroarylcarbonyl; R.sub.12 represents hydrogen, alkyl which is unsubstituted or substituted with a substituent selected from R.sub.18, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylalkyl, aryl, or arylalkyl; when M is ##STR04417## —(CH.sub.2).sub.4— or —CH═CH—CH═CH— formed by R.sub.11 and R.sub.12, the nitrogen atom bound to R.sub.12 and the carbon atom bound to R.sub.11 together form a 6-membered ring; R.sub.15 represents alkyl which is unsubstituted or substituted with a substituent selected from R.sub.21, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, or phenyl; R.sub.16 represents alkyl, halogenated alkyl, cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl; R.sub.21 represents halogen, cyano, cycloalkyl, hydroxy, mercapto, alkoxy, C(O)R.sub.22, carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, —S(O).sub.m-alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with one or more groups selected from R.sub.23; R.sub.17, and R.sub.22 each independently represent hydrogen, alkyl, or N(R.sub.24)R.sub.25; R.sub.23 represents halogen, cyano, nitro, alkyl, alkyl which is unsubstituted or substituted with a substituent selected from R.sub.31, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, alkylcarbonyl, cycloalkylcarbonyl, halogenated alkylcarbonyl, halogenated cycloalkylcarbonyl, alkoxycarbonyl, halogenated alkoxycarbonyl, alkylaminocarbonyl, halogenated alkylaminocarbonyl, bis(alkyl)aminocarbonyl, OR.sub.32, S(O).sub.mR.sub.33, alkylaminosulfonyl, bis(alkyl)aminosulfonyl, NH.sub.2, alkylamino, bis(alkyl)amino, aryl, heteroaryl, or heterocyclyl; R.sub.24, and R.sub.25 each independently represent hydrogen, alkyl, or phenyl; or, alkylidene chain formed by R.sub.24 and R.sub.25, and the nitrogen atom(s) bound to R.sub.24 and R.sub.25 together form a 3-7-membered ring, said alkylidene chain optionally contains one O, S, S(O), S(O).sub.2, NH, or N-alkyl and optionally substituted by oxo or thio group; R.sub.13, R.sub.14, R.sub.18, and R.sub.31 each independently represent halogen, cyano, nitro, carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, S(O).sub.mR.sub.41, OR.sub.42, aryl, heteroaryl, or heterocyclyl; R.sub.32 represents hydrogen, alkyl, halogenated alkyl, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl; R.sub.33 represents alkyl, halogenated alkyl, cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl; R.sub.41, and R.sub.42 each independently represent hydrogen, alkyl, halogenated alkyl, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, or phenyl; r represents 1 or 2; m represents 0, 1 or 2; n represents 0, or 1; s represents 0, 1, 2 or 3.
2. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X, and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C6 alkyl, or C3-C8 cycloalkenyl-C1-C6 alkyl, which is with or without halogen; OR.sup.1, COR.sup.1, COOR.sup.1, OCOR.sup.1, OCOOR.sup.1, NR.sup.3SO.sub.2R.sup.2, OSO.sub.2R.sup.2, S(O).sub.mR.sup.2, NR.sup.3COR.sup.1, NR.sup.3COOR.sup.1, C(O)NR.sup.3OR.sup.1, SO.sub.2OR.sup.1, C(O)NR.sup.4R.sup.5, NR.sup.3C(O)NR.sup.4R.sup.5, OC(O)NR.sup.4R.sup.5, SO.sub.2NR.sup.4R.sup.5, C(S)R.sup.1, C(S)OR.sup.1, C(S)SR.sup.2, C(O)SR.sup.2, SC(O)R.sup.1, SC(S)R.sup.1, OC(S)R.sup.1, —(C1-C6)alkyl-C(S)R.sup.1, —(C1-C6)alkyl-C(S)OR.sup.1, —(C1-C6)alkyl-C(O)SR.sup.1, —(C1-C6)alkyl-C(S)SR.sup.1, —(C1-C6)alkyl-SC(O)R.sup.1, —(C1-C6)alkyl-OC(S)R.sub.1, —(C1-C6)alkyl-SC(S)R.sup.1, —O—(C1-C6)alkyl-NR.sup.4R.sup.5, —S—(C1-C6)alkyl-NR.sup.4R.sup.5, —(C1-C6)alkyl-O—(C1-C6)alkyl-NR.sup.4R.sup.5, —(C1-C6)alkyl-S—(C1-C6)alkyl-NR.sup.4R.sup.5, —(C1-C6)alkyl-(C═S).sub.n—NR.sup.4R.sup.5, —NH—(C1-C6)alkyl-NR.sup.4R.sup.5, —(C1-C6)alkyl-OR.sup.1, —(C1-C6)alkyl-COR.sup.1, —(C1-C6)alkyl-CO.sub.2R.sup.1, —(C1-C6)alkyl-OCOR.sup.1, —(C1-C6)alkyl-NR.sup.3COR.sup.1, —(C1-C6)alkyl-SO.sub.2OR.sup.1, —(C1-C6)alkyl-NR.sup.3SO.sub.2R.sup.2, —(C1-C6)alkyl-OSO.sub.2R.sup.2, -alkyl-S(O).sub.mR.sup.2, —(C1-C6)alkyl-CONR.sup.4R.sup.5, —(C1-C6)alkyl-SO.sub.2NR.sup.4R.sup.5, NR.sup.4R.sup.5, ##STR04418## P(O)(OR.sup.6).sub.2, CH.sub.2P(O)(OR.sup.6).sub.2, SO.sub.2NR.sup.4R.sup.5—(C1-C6)alkyl-S(O).sub.mR.sup.2, —(C1-C6)alkyl-CN, —(C1-C6)alkylaryl, —(C1-C6)alkylheteroaryl, —(C1-C6)alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl; R.sup.1, R.sup.3, R.sup.4, and R.sup.5 each independently represent hydrogen, aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkoxy-C1-C6 alkyl, or C3-C8 cycloalkyl-C1-C6 alkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR.sup.7, S(O).sub.mR.sup.9, NR.sup.7R.sup.8, NR.sup.8OR.sup.7, COR.sup.7, OCOR.sup.7, SCOR.sup.7, NR.sup.8COR.sup.7, CO.sub.2R.sup.7, COSR.sup.7, CONR.sup.7R.sup.8, and C1-C8 alkoxy-C1-C6 alkoxycarbonyl; R.sup.2 represents aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C6 alkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR.sup.7, S(O).sub.mR.sup.9, NR.sup.7R.sup.8, NR.sup.8OR.sup.7, COR.sup.7, OCOR.sup.7, SCOR.sup.7, NR.sup.8COR.sup.7, CO.sub.2R.sup.7, COSR.sup.7, CONR.sup.7R.sup.8, and C1-C8 alkoxy-C1-C6 alkoxycarbonyl; R.sup.6 represents methyl, or ethyl; R.sup.7, and R.sup.8 each independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; R.sup.9 represents C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; M represents ##STR04419## which is unsubstituted or substituted; R.sub.11 represents hydrogen, halogen, cyano, nitro, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R.sub.13, C3-C8 cycloalkyl which is unsubstituted or substituted with a substituent selected from R.sub.14, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, NH.sub.2, aminoacyl, carboxyl, C1-C8 alkoxy-C1-C6 alkoxycarbonyl, OR.sub.15, —(C1-C6)alkyl-OR.sub.15, C(O)R.sub.16, —(C1-C6)alkyl-C(O)R.sub.16, C(O)OR.sub.16, —(C1-C6)alkyl-C(O)OR.sub.16, S(O).sub.mR.sub.16, —(C1-C6)alkyl-S(O).sub.mR.sub.16, —N(R.sub.16).sub.2, —NHR.sub.16, —C(O)NHR.sub.16, —C(O)N(R.sub.16).sub.2, —NHC(O)R.sub.17, heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, aryl-C1-C6 alkyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryl-C1-C6 alkyl, heteroaryloxy, or heteroarylcarbonyl; R.sub.12 represents hydrogen, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R.sub.18, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, C1-C8 alkoxy-C1-C6 alkyl, C1-C8 alkylthio-C1-C6 alkyl, C1-C8 alkoxycarbonyl-C1-C6 alkyl, aryl, or aryl-C1-C6 alkyl; when M is ##STR04420## —(CH.sub.2).sub.4— or —CH═CH—CH═CH— formed by R.sub.11 and R-12, the nitrogen atom bound to R.sub.12 and the carbon atom bound to R.sub.11 together form a 6-membered ring; R.sub.15 represents C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R.sub.21, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or phenyl; R.sub.16 represents C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl; R.sub.21 represents halogen, cyano, C3-C8 cycloalkyl, hydroxy, mercapto, C1-C8 alkoxy, C(O)R.sub.22, carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy-C1-C6 alkoxycarbonyl, —S(O).sub.m—(C1-C8)alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with one or more groups selected from R.sub.23; R.sub.17, and R.sub.22 each independently represent hydrogen, C1-C8 alkyl, or N(R.sub.24)R.sub.25; R.sub.23 represents halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R.sub.31, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, C1-C8 alkylcarbonyl, C3-C8 cycloalkylcarbonyl, halogenated C1-C8 alkylcarbonyl, halogenated C3-C8 cycloalkylcarbonyl, C1-C8 alkoxycarbonyl, halogenated C1-C8 alkoxycarbonyl, C1-C8 alkylaminocarbonyl, halogenated C1-C8 alkylaminocarbonyl, bis(C1-C8 alkyl)aminocarbonyl, OR.sub.32, S(O).sub.mR.sub.33, C1-C8 alkylaminosulfonyl, bis(C1-C8 alkyl)aminosulfonyl, NH.sub.2, C1-C8 alkylamino, bis(C1-C8 alkyl)amino, aryl, heteroaryl, or heterocyclyl; R.sub.24, and R.sub.25 each independently represent hydrogen, C1-C8 alkyl, or phenyl; or, C2-C8 alkylidene chain formed by R.sub.24 and R.sub.25, and the nitrogen atom(s) bound to R.sub.24 and R.sub.25 together form a 3-7-membered ring, said C2-C8 alkylidene chain optionally contains one O, S, S(O), S(O).sub.2, NH, or N-alkyl and optionally substituted by oxo or thio group; R.sub.13, R.sub.14, R.sub.18, and R.sub.31 each independently represent halogen, cyano, nitro, carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy-C1-C8 alkoxycarbonyl, S(O).sub.mR.sub.41, OR.sub.42, aryl, heteroaryl, or heterocyclyl; R.sub.32 represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl; R.sub.33 represents C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl; R.sub.41, and R.sub.42 each independently represent hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or phenyl; r represents 1, or 2; m represents 0, 1, or 2; n represents 0, or 1; s represents 0, 1, 2, or 3; wherein, the “heterocyclyl” is ##STR04421## which has 0, 1, or 2 oxo groups; the “aryl” is phenyl, naphthyl, ##STR04422## the “heteroaryl” is ##STR04423## ##STR04424## the above-mentioned groups are respectively unsubstituted or substituted by at least one group selected from: halogen, nitro, cyano, thiocyano, cyanoalkyl, mercapto, hydroxy, hydroxyalkyl, carboxyl, formyl, trialkylsilyl, dialkylphosphonyl; heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkyl substituted by alkyl, OR″, SR″, -alkyl-OR″, —O— alkyl-OR″, -alkyl-SR″, COR″, -alkyl-COR″, —O-alkyl-COR″, COOR″, -alkyl-COOR″, —O— alkyl-COOR″, COSR″, SOR″, SO.sub.2R″, —O—SO.sub.2R″, -alkyl-SO.sub.2R″, OCOR″, -alkyl-OCOR″, or SCOR″ group, which is with or without halogen; and amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, or aminosulfonyl group which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO.sub.2R″, and OR″, wherein the R″, COR″, COOR″, SO.sub.2R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O— or —CH═CH—CH═CH— group to form a ring, wherein the —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O— or —CH═CH—CH═CH— group is with or without halogen; R″ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl; or heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted.
3. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X represents nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, or C3-C6 cycloalkenyl-C1-C3 alkyl, which is with or without halogen; OR.sup.1, COR.sup.1, COOR.sup.1, OCOR.sup.1, OCOOR.sup.1, NR.sup.3SO.sub.2R.sup.2, OSO.sub.2R.sup.2, S(O).sub.mR.sup.2, NR.sup.3COR.sup.1, NR.sup.3COOR.sup.1, C(O)NR.sup.3OR.sup.1, SO.sub.2OR.sup.1, C(O)NR.sup.4R.sup.5, NR.sup.3C(O)NR.sup.4R.sup.5, OC(O)NR.sup.4R.sup.5, SO.sub.2NR.sup.4R.sup.5, C(S)R.sup.1, C(S)OR.sup.1, C(S)SR.sup.2, C(O)SR.sup.2, SC(O)R.sup.1, SC(S)R.sup.1, OC(S)R.sup.1, —(C1-C3)alkyl-C(S)R.sup.1, —(C1-C3)alkyl-C(S)OR.sup.1, —(C1-C3)alkyl-C(O)SR.sup.1, —(C1-C3)alkyl-C(S)SR.sup.1, —(C1-C3)alkyl-SC(O)R.sup.1, —(C1-C3)alkyl-OC(S)R.sup.1, —(C1-C3)alkyl-SC(S)R.sup.1, —O—(C1-C3)alkyl-NR.sup.4R.sup.5, —S—(C1-C3)alkyl-NR.sup.4R.sup.5, —(C1-C3)alkyl-O—(C1-C3)alkyl-NR.sup.4R.sup.5, —(C1-C3)alkyl-S—(C1-C3)alkyl-NR.sup.4R.sup.5, —(C1-C3)alkyl-(C═S).sub.n—NR.sup.4R.sup.5, —NH—(C1-C3)alkyl-NR.sup.4R.sup.5, —(C1-C3)alkyl-OR.sup.1, —(C1-C3)alkyl-COR.sup.1, —(C1-C3)alkyl-CO.sub.2R.sup.1, —(C1-C3)alkyl-OCOR.sup.1, —(C1-C3)alkyl-NR.sup.3COR.sup.1, —(C1-C3)alkyl-SO.sub.2OR.sup.1, —(C1-C3)alkyl-NR.sup.3SO.sub.2R.sup.2, —(C1-C3)alkyl-OSO.sub.2R.sup.2, -alkyl-S(O).sub.mR.sup.2, —(C1-C3)alkyl-CONR.sup.4R.sup.5, —(C1-C3)alkyl-SO.sub.2NR.sup.4R.sup.5, NR.sup.4R.sup.5, ##STR04425## P(O)(OR.sup.6).sub.2, CH.sub.2P(O)(OR.sup.6).sub.2, SO.sub.2NR.sup.4R.sup.5—(C1-C3)alkyl-S(O).sub.mR.sup.2, —(C1-C3)alkyl-CN, —(C1-C3)alkylaryl, —(C1-C3)alkylheteroaryl, —(C1-C3)alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl; Y represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkenyl, which is with or without halogen; OR.sup.1, S(O).sub.mR.sup.2, NR.sup.4R.sup.5, heterocyclyl, aryl, or heteroaryl; R.sup.1, R.sup.3, R.sup.4, and R.sup.5 each independently represent hydrogen, aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, or C3-C6 cycloalkyl-C1-C3 alkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR.sup.7, S(O).sub.mR.sup.9, NR.sup.7R.sup.8, NR.sup.8OR.sup.7, COR.sup.7, OCOR.sup.7, SCOR.sup.7, NR.sup.8COR.sup.7, CO.sub.2R.sup.7, COSR.sup.7, CONR.sup.7R.sup.8, and C1-C6 alkoxy-C1-C3 alkoxycarbonyl; R.sup.2 represents aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C3 alkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR.sup.7, S(O).sub.mR.sup.9, NR.sup.7R.sup.8, NR.sup.8OR.sup.7, COR.sup.7, OCOR.sup.7, SCOR.sup.7, NR.sup.8COR.sup.7, CO.sub.2R.sup.7, COSR.sup.7, CONR.sup.7R.sup.8, and C1-C6 alkoxy-C1-C3 alkoxycarbonyl; R.sup.6 represents methyl, or ethyl; R.sup.7, and R.sup.8 each independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; R.sup.9 represents C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; M represents ##STR04426## which is unsubstituted or substituted; R.sub.11 represents hydrogen, halogen, cyano, nitro, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R.sub.13, C3-C6 cycloalkyl which is unsubstituted or substituted with a substituent selected from R.sub.14, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, NH.sub.2, aminoacyl, carboxyl, C1-C6 alkoxy-C1-C3 alkoxycarbonyl, OR.sub.15, —(C1-C3)alkyl-OR.sub.15, C(O)R.sub.16, —(C1-C3)alkyl-C(O)R.sub.16, C(O)OR.sub.16, —(C1-C3)alkyl-C(O)OR.sub.16, S(O).sub.mR.sub.16, —(C1-C3)alkyl-S(O).sub.mR.sub.16, —N(R.sub.16).sub.2, —NHR.sub.16, —C(O)NHR.sub.16, —C(O)N(R.sub.16).sub.2, —NHC(O)R.sub.17, heterocyclyl, heterocyclyl-C1-C3 alkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, aryl-C1-C3 alkyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryl-C1-C3 alkyl, heteroaryloxy, or heteroarylcarbonyl; R.sub.12 represents hydrogen, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R.sub.18, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl, aryl, or aryl-C1-C3 alkyl; when M is ##STR04427## —(CH.sub.2).sub.4— or —CH═CH—CH═CH— formed by R.sub.11 and R.sub.12, the nitrogen atom bound to R.sub.12 and the carbon atom bound to R.sub.11 together form a 6-membered ring; R.sub.15 represents C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R.sub.21, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, or phenyl; R.sub.16 represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl; R.sub.21 represents halogen, cyano, C3-C6 cycloalkyl, hydroxy, mercapto, C1-C6 alkoxy, C(O)R.sub.22, carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C3 alkoxycarbonyl, —S(O).sub.m—(C1-C6)alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with 1˜3 groups selected from R.sub.23; R.sub.17, and R.sub.22 each independently represent hydrogen, C1-C6 alkyl, or N(R.sub.24)R.sub.25; R.sub.23 represents halogen, cyano, nitro, C1-C6 alkyl, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R.sub.31, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, C1-C6 alkylcarbonyl, C3-C6 cycloalkylcarbonyl, halogenated C1-C6 alkylcarbonyl, halogenated C3-C6 cycloalkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated C1-C6 alkylaminocarbonyl, bis(C1-C6 alkyl)aminocarbonyl, OR.sub.32, S(O).sub.mR.sub.33, C1-C6 alkylaminosulfonyl, bis(C1-C6 alkyl)aminosulfonyl, NH.sub.2, C1-C6 alkylamino, bis(C1-C6 alkyl)amino, aryl, heteroaryl, or heterocyclyl; R.sub.24, and R.sub.25 each independently represent hydrogen, C1-C6 alkyl, or phenyl; or, C2-C6 alkylidene chain formed by R.sub.24 and R.sub.25, and the nitrogen atom(s) bound to R.sub.24 and R.sub.25 together form a 3-7-membered ring, said C2-C6 alkylidene chain optionally contains one O, S, S(O), S(O).sub.2, NH, or N-alkyl and optionally substituted by oxo or thio group; R.sub.13, R.sub.14, R.sub.18, and R.sub.31 each independently represent halogen, cyano, nitro, carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C6 alkoxycarbonyl, S(O).sub.mR.sub.41, OR.sub.42, aryl, heteroaryl, or heterocyclyl; R.sub.32 represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl; R.sub.33 represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl; R.sub.41, and R.sub.42 each independently represent hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, or phenyl; r represents 1, or 2; m represents 0, 1, or 2; n represents 0, or 1; s represents 0, 1, 2, or 3; wherein, the “heterocyclyl” is ##STR04428## which has 0, 1, or 2 oxo groups; the “aryl” is phenyl, naphthyl, ##STR04429## the “heteroaryl” is ##STR04430## ##STR04431## ##STR04432## the above-mentioned groups are respectively unsubstituted or substituted by 1˜3 groups selected from: halogen, nitro, cyano, thiocyano, cyano C1-C6 alkyl, mercapto, hydroxy, hydroxy C1-C6 alkyl, carboxyl, formyl; ##STR04433## phenyl, or benzyl group, which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxycarbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, OR″, SR″, —(C1-C6) alkyl —OR″, —O—(C1-C6) alkyl —OR″, —(C1-C6) alkyl —SR″, COR″, —(C1-C6) alkyl —COR″, —O—(C1-C6) alkyl —COR″, COOR″, —(C1-C6) alkyl —COOR″, —O—(C1-C6) alkyl —COOR″, COSR″, SOR″, SO.sub.2R″, —O—SO.sub.2R″, —(C1-C6) alkyl —SO.sub.2R″, OCOR″, —(C1-C6) alkyl —OCOR″, or SCOR″ group, which is with or without halogen; and amino, aminoalkyl, aminocarbonyl, or aminosulfonyl group, which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO.sub.2R″, and OR″, wherein the R″, COR″, COOR″, SO.sub.2R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O—, or —CH═CH—CH═CH— group is with or without halogen; R′ each independently represents hydrogen, nitro, hydroxy, amino; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C6 alkyl, ##STR04434## C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl-C1-C6 alkyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, C1-C6 alkylaminocarbonyl, C1-C6 alkoxyaminocarbonyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl, C1-C6 alkylaminocarbonyl-C1-C6 alkyl, tri(C1-C6 alkyl)silyl, or di(C1-C6 alkyl)phosphonyl, which is with or without halogen; or phenyl, or benzyl which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxycarbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen; R″ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl; or ##STR04435## phenyl, or benzyl which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxycarbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen.
4. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X represents halogen, nitro, cyano, OR.sup.1, S(O).sub.mR.sup.2, NR.sup.3COR.sup.1, NR.sup.4R.sup.5, ##STR04436## C1-C6 alkoxy-C1-C3 alkyl; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, which is with or without halogen; ##STR04437## or phenyl which is unsubstituted or substituted with 1,2, or 3 groups selected from halogen, and C1-C6 alkoxy; Y represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkenyl, which is with or without halogen; OR.sup.1, S(O).sub.mR.sup.2, NR.sup.4R.sup.5, heterocyclyl, aryl, or heteroaryl; R.sup.1, R.sup.3, R.sup.4, and R.sup.5 each independently represent hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl; or benzyl which is unsubstituted or substituted with 1, 2, or 3 groups selected from halogen, and C1-C6 alkoxy; R.sup.2 represents C1-C6 alkyl, or halogenated C1-C6 alkyl; M represents ##STR04438## which is unsubstituted or substituted; R.sub.11 represents hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, halogen, C1-C6 alkylamino, bis(C1-C6 alkyl)amino, cyano, nitro, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl, aminocarbonyl, C1-C6 alkylcarbonylamino, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkylsulfinyl-C1-C3 alkyl, C1-C6 alkylsulfonyl-C1-C3 alkyl; or benzyl, phenoxy, benzoyl, pyridyl, ##STR04439## which is unsubstituted or substituted with 1,2, or 3 groups selected from halogen, and C1-C6 alkoxy; R.sub.12 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl; or phenyl, or benzyl which is unsubstituted or substituted with at least one group selected from halogen, and halogenated C1-C6 alkyl; r represents 1, or 2; m represents 0, 1, or 2; wherein, the “heterocyclyl” is ##STR04440## the “aryl” is phenyl, naphthyl, or ##STR04441## which is unsubstituted or substituted; the “heteroaryl” is ##STR04442## ##STR04443## which is unsubstituted or substituted; the aforementioned “substituted” respectively refers to being substituted by 1˜3 groups selected from: halogen, nitro, cyano, thiocyano, cyano C1-C3 alkyl, hydroxy, hydroxy C1-C3 alkyl, mercapto, carboxyl, formyl, ##STR04444## phenyl, phenyl substituted by C1-C6 alkyl, phenoxy, benzyloxy; amino, aminoalkyl, or aminocarbonyl group which is unsubstituted or substituted by one or two groups selected from C1-C6 alkyl, COR″, and COOR″; and C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkylcarbonylthio, C3-C6 cycloalkyl substituted with C1-C6 alkyl, OR″, SR″, SOR″, COR″, COOR″, or SO.sub.2R″, which is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O—, or —CH═CH—CH═CH— group, which is with or without halogen; R′ each independently represents hydrogen, C1-C6 alkyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkyl, ##STR04445## C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C3 alkyl, or benzyl; R″ each independently represents C1-C6 alkyl, or C2-C6 alkenyl; wherein, when X is fluorine, Y is not amino, monomethylamino, monoethylamino and monopropylamino; when M is ##STR04446## X and Y are not methyl at the same time.
5. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X represents chlorine, fluorine, bromine, methyl, ethyl, isopropyl, vinyl, allyl, ethynyl, cyclopropyl, trifluoromethyl, ##STR04447## hydroxy, methoxy, ethyloxy, methylthio, ethylthio, ##STR04448## nitro, cyano, methylsulfinyl, ethylsulfinyl, methylsulfonyl, amino, monomethylamino, dimethylamino, acetamido, ##STR04449## phenyl, phenoxy, or 4-fluorophenyl; Y represents methyl, ethyl, vinyl, methoxy, ##STR04450## phenoxy, benzyloxy, methylthio, propylthio, tert-butylthio, benzylthio, 4-methoxybenzylthiol, propylsulfinyl, amino, monomethylamino, dimethylamino, anilino, p-methoxybenzylamino, tert-butyl, cyclopropyl, cyclohexyl, ##STR04451## heterocyclyl, aryl, or heteroaryl; M represents ##STR04452## which is unsubstituted or substituted; R.sub.11 each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, monochloromethyl, trifluoromethyl, methoxy, isopropyloxy, methylthio, fluorine, chlorine, bromine, iodine, dimethylamino, ethylamino, cyano, nitro, acetyl, methoxycarbonyl; phenyl which is unsubstituted or substituted by 1,2, or 3 groups selected from chlorine, and methoxy; pyridyl, ##STR04453## R.sub.12 each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, allyl, ##STR04454## or phenyl, or benzyl which is unsubstituted or substituted by 1,2, or 3 groups selected from chlorine, and trifluoromethyl; r represents 1, or 2; wherein, the “heterocyclyl” is ##STR04455## the “aryl” is phenyl, naphthyl, or ##STR04456## which is unsubstituted or substituted; the “heteroaryl” ##STR04457## ##STR04458## which is unsubstituted or substituted; the aforementioned “substituted” refers to being substituted by 1,2, or 3 groups selected from: methyl, ethyl, isopropyl, n-butyl, tert-butyl, n-pentyl, vinyl, cyclopropyl, ##STR04459## fluorine, chlorine, bromine, iodine, monobromomethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy, trifluoromethoxy, hydroxyl, hydroxymethyl, amino, cyano, cyanomethyl, thiocyano, mercapto, nitro, carboxy, formyl, acetyl, methoxycarbonyl, tert-butyloxycarbonyl, methylthio, isopropylthio, methylsulfinyl, methylsulfonyl, ##STR04460## dimethylamino, aminocarbonyl, dimethylaminocarbonyl, acetylamino, ##STR04461## phenyl, 4-ethylphenyl, phenoxy, and benzyloxy; or, two adjacent substitutable positions of the above-mentioned “aryl”, “heteroaryl” groups are linked with —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O—, or —CH═CH—CH═CH— group is with or without halogen; R′ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, difluoromethyl, 3,3,3-trifluoroethyl, benzyl, ##STR04462## wherein, when X is fluorine, Y is not amino and monomethylamino; when M is ##STR04463## X and Y are not methyl at the same time.
6.-10. (canceled)
11. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is selected from the compounds of formula I as listed in Table A1.
12. A method for preparing the 4-pyridinyl formamide compound of claim 1, comprising subjecting the compound of formula II and the compound of formula III to an amidation reaction to obtain the compound of formula I as follows: ##STR04464## wherein the reaction is carried out in the presence of a halogenating agent, a catalyst and a solvent; or wherein the reaction is carried out in the presence of a condensing agent and a solvent.
13. The method of claim 12, wherein the reaction is carried out in the presence of SOCl.sub.2 as the halogenating agent, 4-dimethylaminopyridine as the catalyst, and pyridine as the solvent.
14. The method of claim 12, wherein the reaction is carried out in the presence of CDI, DCC, DBU, or a combination thereof as the condensing agent, and methylene chloride as the solvent.
15. A herbicidal composition, comprising (i) the 4-pyridinyl formamide compound or derivative thereof of claim 1; optionally further comprising (ii) at least one additional herbicide and/or safener, and/or (iii) at least one agrochemically acceptable formulation auxiliary.
16. A method for controlling a weed, comprising applying a herbicidally effective amount of at least one 4-pyridinyl formamide compound or derivative thereof of claim 1 on a plant or in a weed area.
17. A method for preventing and/or controlling a weed in a useful crop, comprising applying at least one 4-pyridinyl formamide compound or derivative thereof of claim 1 on the useful crop or in a weed area.
18. The method of claim 17, wherein the useful crop is a transgenic crop, or a crop treated by gene editing technique.
19. A method for controlling a weed, comprising applying a herbicidally effective amount of at least one herbicidal composition of claim 15 on a plant or in a weed area.
20. A method for preventing and/or controlling a weed in a useful crop, comprising applying at least one herbicidal composition of claim 15 on the useful crop or in a weed area.
21. The method of claim 20, wherein the useful crop is a transgenic crop, or a crop treated by gene editing technique.
Description
SPECIFIC MODE FOR CARRYING OUT THE INVENTION
[0175] The following embodiments are used to illustrate the present invention in detail and should not be taken as any limit to the present invention. The scope of the invention would be explained through the Claims.
[0176] In view of economics and variety of a compound, we preferably synthesized several compounds, part of which are listed in the following Table A1. The structure and information of a certain compound are shown in Table A1. The compounds in Table A1 are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.
TABLE-US-00001 TABLE A1 Structures and .sup.1H NMR data of compounds I [00058]
NO. X Y M .sup.1HNMR 1-1 Cl CH.sub.3 [00059]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.52 (d, J = 5.5 Hz, 1H), 7.49 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 2.50 (s, 3H). 1-2 Cl [00060]
[00061]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.47 (d, J = 5.5 Hz, 1H), 7.50 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 1.54 (s, 9H). 1-3 Cl [00062]
[00063]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.45 (d, J = 5.5 Hz, 1H), 7.48 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 2.62-2.57 (m, 1H), 1.03-0.94 (m, 2H), 0.95-0.85 (m, 2H). 1-4 Cl [00064]
[00065]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.48 ((d, J = 5.5 Hz, 1H), 7.49 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 3.05-3.01 (m, 1H), 1.99-1.95 (m, 2H), 1.73-1.70 (m, 2H), 1.60-1.45 (m, 6H). 1-5 Cl [00066]
[00067]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 11.98 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 6.03 (t, J = 7.0 Hz, 1H), 4.00 (s, 3H), 2.35-2.10 (m, 4H), 1.74 (t, J = 6.0 Hz, 2H), 1.69-1.60 (m, 2H). 1-6 Cl [00068]
[00069]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.23 (d, J = 5.0 Hz, 1H), 6.58- 6.53 (m, 1H), 4.32 (s, 3H), 3.55 (t, J = 5.5 Hz, 2H), 3.33 (dt, J = 6.5, 1.5 Hz, 2H), 3.20 (t, J = 5.5, 1.5 Hz, 2H), 1.47 (s, 9H). 1-7 Cl [00070]
[00071]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 6.12-6.09 (m, 1H), 4.31 (s, 3H), 4.20-4.15 (m, 2H), 3.79 (t, J = 5.5 Hz, 2H), 2.16-2.10 (m, 2H). 1-8 Cl [00072]
[00073]
1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 5.50 Hz, 1H), 7.69-7.63 (m, 2H), 7.55-7.45 (m, 3H), 3.97 (s, 3H). 1-9 Cl [00074]
[00075]
1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.33-7.22 (m, 3H), 7.21 (d, J = 7.5 Hz, 1H), 3.99 (s, 3H), 2.07 (s, 3H). 1-10 Cl [00076]
[00077]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.89-7.83 (m, 1H), 7.81-7.71 (m, 2H), 7.59 (t, J = 7.5 Hz, 1H), 7.32-7.21 (m, 1H), 4.33 (s, 3H), 2.47 (d, J = 1.5 Hz, 3H). 1-11 Cl [00078]
[00079]
1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.57 (d, J = 8.0 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H), 4.00 (s, 3H), 2.37 (s, 3H). 1-12 Cl [00080]
[00081]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.12 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.89-7.75 (m, 1H), 7.46-7.41 (m, 2H), 7.36-7.27 (m, 1H), 7.20 (d, J = 7.5 Hz, 1H), 4.01 (s, 3H), 3.33 (q, J = 7.5 Hz, 2H), 1.01 (t, J = 7.5 Hz, 3H). 1-13 Cl [00082]
[00083]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 8.0 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 3.98 (s, H), 2.62 (t, J = 8.0 Hz, 2H), 1.60-1.29 (m, 6H), 0.85 (t, J = 6.5 Hz, 3H). 1-14 Cl [00084]
[00085]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.74-7.69 (m, 2H), 7.52-7.46 (m, 2H), 4.33 (s, 3H), 2.09-1.98 (m, 2H), 1.81-1.67 (m, 4H), 1.35-1.24 (m, 2H), 1.27-1.13 (m, 6H), 0.83 (t, J = 8.0 Hz, 3H). 1-15 Cl [00086]
[00087]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 8.80 (d, J = 4.5 Hz, 1H), 7.85 (d, J = 4.5 Hz, 1H), 7.63-7.55 (m, 1H), 7.51-7.46 (m, 1H), 7.40-7.31 (m, 2H), 3.99 (s, 3H). 1-16 Cl [00088]
[00089]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.87-7.79 (m, 1H), 7.72 (d, J = 5.0 Hz, 1H), 7.69-7.63 (m, 1H), 7.48-7.46 (m, 1H), 7.32-7.20 (m, 1H), 4.33 (s, 3H). 1-17 Cl [00090]
[00091]
1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.79-7.69 (m, 3H), 7.39-7.26 (m, 2H), 3.99 (s, 3H) 1-18 Cl [00092]
[00093]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 7.85 (dd, J = 7.5, 2.5 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.52-7.43 (m, 2H), 7.41-7.37 (m, 1H), 4.26 (s, 3H). 1-19 Cl [00094]
[00095]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.02 (t, J = 2.0 Hz, 1H), 7.89-7.71 (m 2H), 7.68 (d, J = 5.0 Hz, 1H), 7.45 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-20 Cl [00096]
[00097]
1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 8.0 Hz, 2H), 7.58 (d, J = 8.0 Hz, 2H), 4.00 (s, 3H). 1-21 Cl [00098]
[00099]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.56 (d, J = 5.5 Hz, 1H), 7.96 (t, J = 2.5 Hz, 1H), 7.88-7.86 (m, 1H), 7.61 (d, J = 5.5 Hz, 1H), 7.55-7.52 (m, 1H), 7.45 (t, J = 7.5 Hz, 1H), 4.25 (s, 3H). 1-22 Cl [00100]
[00101]
1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.72 (d, J = 8.0 Hz, 1H), 7.66-7.60 (m, 2H), 7.56-7.45 (m, 1H), 3.99 (s, 3H). 1-23 Cl [00102]
[00103]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.56 (d, J = 5.5 Hz, 1H), 8.06 (dd, J = 7.5, 2.0 Hz, 1H), 7.61 (d, J = 5.5 Hz, 1H), 7.39-7.36 (m, 1H), 7.35-7.29 (m, 2H), 4.73 (s, 2H), 4.25 (s, 3H). 1-24 Cl [00104]
[00105]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 7.96-7.90 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.3-7.26 (m, 2H), 4.40 (s, 2H), 4.25 (s, 3H). 1-25 Cl [00106]
[00107]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.57 (d, J = 5.5 Hz, 1H), 7.89-7.82 (m, 2H), 7.72-7.66 (m, 2H), 7.50 (d, J = 5.5 Hz, 1H), 4.26 (s, 3H). 1-26 Cl [00108]
[00109]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.01 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.06-7.94 (m, 2H), 7.88 (d, J = 8.0 Hz, 1H), 7.84 (s, 1H), 7.80-7.76 (m, 1H), 4.00 (s, 3H). 1-27 Cl [00110]
[00111]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.98-7.79 (m, 5H), 4.07 (s, 3H). 1-28 Cl [00112]
[00113]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.50-7.42 (m, 1H), 7.26-7.19 (m, 1H), 7.14 (d, J = 8.5 Hz, 1H), 7.06 (t, J = 7.5 Hz, 1H), 3.98 (s, 3H), 3.74 (s, 3H). 1-29 Cl [00114]
[00115]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.68-7.57 (m, 1H), 7.33 (t, J = 7.5 Hz, 1H), 7.23 (t, J = 2.0 Hz, 1H), 6.89-6.81 (m, 1H), 4.33 (s, 3H), 3.80 (s, 3H). 1-30 Cl [00116]
[00117]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.02 (s, 1H), 8.73 (d, J = 4.5 Hz, 1H), 7.69 (d, J = 4.5 Hz, 1H), 7.66 (d, J = 8.5 Hz, 2H), 6.88 (d, J = 8.5 Hz, 2H) 3.99 (s, 3H), 3.81 (s, 3H) 1-31 Cl [00118]
[00119]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.13 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.85 (s, 1H), 7.70- 7.65 (m, 1H), 7.58-7.44 (m, 3H), 3.98 (s, 3H). 1-32 Cl [00120]
[00121]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.16 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.77-7.71 (m, 2H), 7.64 (d, J = 8.0 Hz, 1H), 4.11 (s, 3H). 1-33 Cl [00122]
[00123]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.78 (d, J = 4.5 Hz, 1H), 7.82-7.76 (m, 3H), 7.61- 7.35 (m, 2H), 4.00 (s, 3H). 1-34 Cl [00124]
[00125]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 9.74 (s, 1H), 8.54 (d, J = 5.5 Hz, 1H), 8.04 (dd, J = 7.5, 2.0 Hz, 1H), 7.49 (d, J = 5.5 Hz, 1H), 7.32-7.21 (m, 2H), 7.01 (dd, J = 7.5, 2.0 Hz, 1H), 4.25 (s, 3H). 1-35 Cl [00126]
[00127]
1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.63 (s, 1H), 8.71 (d, J = 4.5 Hz, 1H), 7.74-7.64 (m, 3H), 6.79-6.73 (m, 2H), 4.33 (s, 3H). 1-36 Cl [00128]
[00129]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 7.52 (d, J = 7.5 Hz, 1H), 7.48-7.35 (m, 2H), 5.28 (s, 1H), 4.56 (s, 2H), 3.98 (s, 3H). 1-37 Cl [00130]
[00131]
1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.71 (d, J = 4.5 Hz, 1H), 7.88-7.82 (m, 2H), 7.70 (d, J = 4.5 Hz, 1H), 6.58-6.52 (m, 2H), 6.27 (s, 2H), 4.33 (s, 3H). 1-38 Cl [00132]
[00133]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.10 (dd, J = 6.5, 2.5 Hz, 1H), 7.97 (dd, J = 7.0, 2.5 Hz, 1H), 7.66-7.62 (m, 2H), 7.22 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-39 Cl [00134]
[00135]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.56 (s, 1H), 12.06 (s, 1H), 8.57 (d, J = 5.5 Hz, 1H), 8.07- 8.01 (m, 1H), 7.99-7.93 (m, 2H), 7.51 (d, J = 5.5 Hz, 1H), 4.26 (s, 3H). 1-40 Cl [00136]
[00137]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 8.0 Hz, 2H), 7.82 (d, J = 8.0 Hz, 2H), 7.32 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H), 3.88 (s, 3H). 1-41 Cl [00138]
[00139]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 8.03 (d, J = 8.0 Hz, 2H), 7.78 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H), 1.56 (s, 9H). 1-42 Cl [00140]
[00141]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.81 (dd, J =7.5, 2.0 Hz, 1H), 7.45-7.34 (m, 2H), 7.23-7.18 (m, 1H), 7.10 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 2.35 (s, 3H). 1-43 Cl [00142]
[00143]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.57 (d, J = 5.5 Hz, 1H), 7.97-7.91 (m, 2H), 7.54-7.47 (m, 3H), 4.26 (s, 3H), 3.33 (hept, J = 6.5 Hz, 1H), 1.31 (d, J = 6.5 Hz, 6H). 1-44 Cl [00144]
[00145]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 8.39 (t, J = 2.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.63 (t, J = 7.5 Hz, 1H), 7.28 (d, J = 4.5 Hz, 1H), 4.32 (s, 3H), 3.25 (s, 3H). 1-45 Cl [00146]
[00147]
1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.01 (d, J = 8.0 Hz, 2H), 7.93 (d, J = 8.0 Hz, 2H), 7.86 (d, J = 5.0 Hz, 1H), 3.98 (s, 3H), 3.18 (s, 3H). 1-46 Cl [00148]
[00149]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 7.98 (d, J = 8.0 Hz, 2H), 7.91 (d, J = 8.0 Hz, 2H), 7.45 (d, J = 5.0 Hz, 1H), 4.03 (s, 3H), 3.73-3.64 (m, 4H), 2.95 (t, J = 4.5 Hz, 4H). 1-47 Cl [00150]
[00151]
1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 10.14 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.73- 7.67 (m, 3H), 7.66-7.61 (m, 2H), 3.98 (s, 3H), 2.06 (s, 3H). 1-48 Cl [00152]
[00153]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 11.36 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.86- 7.80 (m, 2H), 7.77-7.70 (m, 2H), 7.42 (t, J = 7.0 Hz, 1H), 6.48 (dd, J = 16.5, 10.0 Hz, 1H), 6.29-6.20 (m, 1H), 5.78 (dd, J = 16.5, 10.0 Hz, 1H), 4.33 (s, 3H). 1-49 Cl [00154]
[00155]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.12 (s, 1H), 7.99-7.90 (m, 2H), 7.84 (d, J = 5.0 Hz, 1H), 7.74 (t, J = 7.5 Hz, 1H), 3.99 (s, 3H). 1-50 Cl [00156]
[00157]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.00 (d, J = 8.0 Hz, 2H), 7.86 (d, J = 8.0 Hz, 2H), 7.46 (t, J = 5.0 Hz, 1H), 4.00 (s, 3H). 1-51 Cl [00158]
[00159]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.94 (d, J = 4.5 Hz, 1H), 7.70-7.64 (m, 2H), 7.35 (d, J = 4.5 Hz, 1H), 7.06-6.99 (m, 2H), 5.33 (t, J = 6.5 Hz, 1H), 4.33 (s, 3H), 3.83-3.81 (m, 1H), 3.52-3.49 (m, 1H), 2.11-1.99 (m, 1H), 1.89-1.77 (m, 2H), 1.61-1.40 (m, 3H). 1-52 Cl [00160]
[00161]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.00 (dd, J = 7.5, 2.0 Hz, 1H), 7.68-7.64 (m, 3H), 7.63-7.53 (m, 3H), 7.49-7.41 (m, 2H), 7.40-7.35 (m, 1H), 4.25 (s, 3H). 1-53 Cl [00162]
[00163]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.79 (dd, J = 5.0, 2.5 Hz, 1H), 7.92-7.67 (m, 7H), 7.51-7.47 (m, 2H), 7.42-7.34 (m, 1H), 4.00 (s, 3H). 1-54 Cl [00164]
[00165]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.14-8.08 (m, 2H), 7.90-7.81 (m, 3H), 7.65-7.59 (m, 2H), 7.40- 7.35 (m, 2H), 4.33 (s, 3H), 2.77-2.67 (m, 2H), 1.19 (t, J = 8.0 Hz, 3H). 1-55 Cl [00166]
[00167]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 7.5 Hz, 1H), 7.46 (td, J = 7.5, 2.0 Hz, 1H), 7.38 (td, J = 7.5, 2.0 Hz, 1H), 7.36-7.28 (m, 2H), 4.32 (s, 3H). 1-56 Cl [00168]
[00169]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.02 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.68-7.54 (m, 1H), 7.47-7.43 (m, 2H), 7.41 7.27 (m, 5H), 6.85-6.72 (m, 1H), 5.10 (s, 2H), 4.33 (s, 3H). 1-57 Cl [00170]
[00171]
1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.24 (dd, J = 7.5, 2.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.52-7.48 (m, 1H), 7.43-7.33 (m, 3H), 7.32-7.28 (m, 1H), 7.14-7.10 (m, 1H), 7.09-7.04 (m, 2H), 4.33 (s, 3H). 1-58 Cl [00172]
[00173]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.51 (d, J = 5.5 Hz, 1H), 7.59 (d, J = 5.5 Hz, 1H), 7.31-7.23 (m, 3H), 4.25 (s, 3H), 2.38 (s, 6H). 1-59 Cl [00174]
[00175]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.13-7.05 (m, 2H), 4.33 (s, 3H), 2.43 (d, J = 1.0 Hz, 3H), 2.31 (s, 3H). 1-60 Cl [00176]
[00177]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.01 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.73 (s, 1H), 7.24 (s, 2H), 7.11 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 2.33 (s, 6H). 1-61 Cl [00178]
[00179]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.74 (d, J = 5.5 Hz, 1H), 7.81-7.78 (m, 2H), 7.56 (d, J = 5.5 Hz, 1H), 7.49 (t J = 2.5 Hz, 1H), 4.26 (s, 3H), 1.31 (s, 18H). 1-62 Cl [00180]
[00181]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.50 (d, J = 5.5 Hz, 1H), 7.68-7.65 (m, 1H), 7.59 (d, J = 5.5 Hz, 1H), 7.40-7.27 (m, 2H), 4.26 (s, 3H). 1-63 Cl [00182]
[00183]
.sup.1H NMR (500 MHz, DMSO-d6) δ 11.85 (s, 1H), 8.74 (d, J = 4.5 Hz, 1H), 7.64-7.58 (m, 1H), 7.39- 7.32 (m, 1H), 7.2-7.15 (m, 1H), 7.08 (d, J = 4.5 Hz, 1H), 4.31 (s, 3H). 1-64 Cl [00184]
[00185]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 5.0 Hz, 1H), 7.57-7.52 (m, 1H), 7.44 (t, J = 10.0 Hz, 1H), 7.26 (dd, J = 8.5, 7.0 Hz, 1H), 3.99 (s, 3H). 1-65 Cl [00186]
[00187]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 7.40 (t, J = 9.0 Hz, 2H), 7.25-7.20 (m, 1H), 3.99 (s, 3H). 1-66 Cl [00188]
[00189]
1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.78 (d, J = 5.5 Hz, 1H), 7.86-7.70 (m, 2H), 7.66-7.49 (m, 2H), 4.00 (s, 3H),. 1-67 Cl [00190]
[00191]
1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 7.29-7.19 (m, 3H), 3.99 (s, 3H), 2.34 (s, 3H). 1-68 Cl [00192]
[00193]
.sup.1H NMR (500 MHz, DMSO-d6) δ 11.96 (s, 1H), 8.78 (d, J = 4.5 Hz, 1H), 7.54 (d, J = 8.5, 1H), 7.37 (dd, J = 7.5, 2.0 Hz, 1H), 7.26 (d, J = 4.5 Hz, 1H), 7.20-7.16 (m, 1H), 4.32 (s, 3H), 2.29 (s, 3H). 1-69 Cl [00194]
[00195]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.80 (s, 1H), 7.35 (t, J = 8.0 Hz, 1H), 7.17 (t, J = 10.5 Hz, 2H), 3.98 (s, 3H), 2.39 (s, 3H),. 1-70 Cl [00196]
[00197]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.51 (d, J = 5.5 Hz, 1H), 7.56 (d, J = 5.5 Hz, 1H), 7.42-7.38 (m, 1H), 7.13-7.10 (m, 1H), 6.82-6.80 (m, 1H), 4.26 (s, 3H), 3.85 (s, 3H). 1-71 Cl [00198]
[00199]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.48 (d, J = 5.5 Hz, 1H), 7.56-7.49 (m, 2H), 7.17 (t, J = 2.0 Hz, 1H), 6.80-6.75 (m, 1H), 4.26 (s, 3H), 3.80 (s, 3H). 1-72 Cl [00200]
[00201]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.84 (d, J = 4.5 Hz, 1H), 7.34-7.19 (m, 2H), 6.98-6.95 (m, 1H), 3.99 (s, 3H), 3.88 (s, 3H). 1-73 Cl [00202]
[00203]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.55 (d, J = 5.5 Hz, 1H), 7.80 (dd, J = 8.5, 7.5 Hz, 1H), 7.60-7.50 (m, 2H), 7.23-7.20 (m, 1H), 4.25 (s, 3H). 1-74 Cl [00204]
[00205]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.45-7.39 (m, 1H), 7.33-7.23 (m, 2H), 4.32 (s, 3H). 1-75 Cl [00206]
[00207]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.14 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.94-7.84 (m, 3H), 7.65-7.51 (m, 1H), 3.99 (s, 3H). 1-76 Cl [00208]
[00209]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.55 (d, J = 5.5 Hz, 1H), 8.05 (d, J = 8.5 Hz, 1H), 7.84 (d, J = 2.0 Hz, 1H), 7.74 (dd, J = 8.5, 2.0 Hz, 1H), 7.58 (d, J = 5.5 Hz, 1H), 4.26 (s, 3H). 1-77 Cl [00210]
[00211]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.19 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.49 (s, 2H), 8.42 (s, 1H), 8.02 (d, J = 5.0 Hz, 1H), 4.12 (s, 3H). 1-78 Cl [00212]
[00213]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.05-7.95 (m, 2H), 7.69 (d, J = 5.5 Hz, 1H), 7.51 (dd, J = 13.5, 2.5 Hz, 1H), 4.33 (s, 3H). 1-79 Cl [00214]
[00215]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 8.70 (d, J = 5.5 Hz, 1H), 7.96-7.89 (m, 2H), 7.76 (dd, J = 8.0, 7.0 Hz, 1H), 7.71 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-80 Cl [00216]
[00217]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.12-8.08 (m, 1H), 7.82-7.78 (m, 1H), 7.69 (d, J = 5.5 Hz, 1H), 7.32 (dt, J = 7.5, 2.5 Hz, 1H), 4.33 (s, 3H). 1-81 Cl [00218]
[00219]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.70 (d, J = 5.5 Hz, 1H), 8.06-7.95 (m, 2H), 7.89 (t, J = 2.0 Hz, 1H), 7.70-7.68 (m, 1H), 4.33 (s, 3H). 1-82 Cl [00220]
[00221]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.07 (dd, J = 7.5, 2.0 Hz, 1H), 7.77-7.73 (m, 1H), 7.70 (d, J = 5.5 Hz, 1H), 7.45 (dd, J = 11.5, 7.5 Hz, 1H), 4.33 (s, 3H). 1-83 Cl [00222]
[00223]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.70 (d, J = 5.5 Hz, 1H), 7.99-7.95 (m, 2H), 7.67 (d, J = 5.5 Hz, 1H), 7.49-7.45 (m, 1H), 4.33 (s, 3H). 1-84 Cl [00224]
[00225]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.26-8.21 (m, 1H), 8.16 (dd, J = 8.0, 2.5 Hz, 1H), 7.70 (d, J = 5.5 Hz, 1H), 7.47 (dd, J = 13.5, 7.5 Hz, 1H), 4.33 (s, 3H). 1-85 Cl [00226]
[00227]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.17-8.01 (m, 2H), 7.84 (d, J = 7.5 Hz, 1H), 7.69-7.64 (m, 1H), 4.00 (s, 3H),. 1-86 Cl [00228]
[00229]
1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.90-7.85 (m, 1H), 7.81 (d, J = 2.0 Hz, 1H), 7.58 (dd, J = 8.5, 2.0 Hz, 1H), 7.48 (d, J = 8.5 Hz, 1H), 3.99 (s, 3H). 1-87 Cl [00230]
[00231]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.18 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 7.0 Hz, 1H), 7.84-7.77 (m, 1H), 7.58-7.51 (m, 1H), 7.44 (d, J = 7.0 Hz, 1H), 4.02 (s, 3H). 1-88 Cl [00232]
[00233]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 2.0 Hz, 1H), 7.85-7.77 (m, 2H), 7.70-7.67 (m, 1H), 4.00 (s, 3H). 1-89 Cl [00234]
[00235]
1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.84 (d, J = 4.5 Hz, 1H), 7.78 (t, J = 2.0 Hz, 1H), 7.71 (d, J = 2.0 Hz, 2H), 3.99 (s, 3H). 1-90 Cl [00236]
[00237]
1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.84 (d, J = 4.5 Hz, 1H), 7.62 (dt, J = 9.0, 2.0 Hz, 1H), 7.57 (s, 1H), 7.52 (d, J = 9.0 Hz, 1H), 3.99 (s, 3H). 1-91 Cl [00238]
[00239]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.82 (d, J = 9.0 Hz, 1H), 7.76-7.71 (m, 2H), 7.55 (d, J = 8.5 Hz, 1H), 3.99 (s, 3H). 1-92 Cl [00240]
[00241]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.87-7.81 (m, 2H), 7.68 (d, J = 5.0 Hz, 1H), 7.29-7.22 (m, 1H), 4.33 (s, 3H). 1-93 Cl [00242]
[00243]
1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.73-7.66 (m, 1H), 7.54- 7.42 (m, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.18 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-94 Cl [00244]
[00245]
1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 5.0 Hz, 1H), 7.64 (dd, J = 9.0, 2.5 Hz, 1H), 7.51 (dd, J = 8.5, 6.0 Hz, 1H), 7.38-7.30 (m, 1H), 3.98 (s, 3H). 1-95 Cl [00246]
[00247]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.69-7.62 (m, 1H), 7.55 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 8.0, 2.0 Hz, 1H), 3.99 (s, 3H). 1-96 Cl [00248]
[00249]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 8.62 (d, J = 5.5 Hz, 1H), 7.84 (d, J = 2.0 Hz, 1H), 7.71 (d, J = 8.5 Hz, 1H), 7.62 (d, J = 5.5 Hz, 1H), 7.55 (dd, J = 8.5, 2.0 Hz, 1H), 4.26 (s, 3H). 1-97 Cl [00250]
[00251]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.54 (d, J = 5.5 Hz, 1H), 7.84-7.80 (m, 1H), 7.65- 7.56 (m, 2H), 7.28-7.24 (m, 1H), 4.26 (s, 3H). 1-98 Cl [00252]
[00253]
.sup.1H NMR (500 MHz, DMSO-d6) δ 11.99 (s, 1H), 8.75 (d, J = 4.5 Hz, 1H), 8.14 (d, J = 2.0 Hz, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 7.5 Hz, 1H), 7.09 (d, J = 4.5 Hz, 1H), 4.32 (s, 3H), 3.94 (s, 3H). 1-99 Cl [00254]
[00255]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 11.26 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.38 (d, J = 2.0 Hz, 1H), 8.02 (dd, J = 7.5, 2.0 Hz, 1H), 7.68 (d, J = 5.0 Hz, 1H), 7.09 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H), 3.90 (s, 3H). 1-100 Cl [00256]
[00257]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.19 (s, 1H), 12.01 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.70 (s, 1H), 8.66 (s, 1H), 7.88 (s, 1H), 7.63 (d, J = 4.5 Hz, 1H), 4.00 (s, 3H). 1-101 Cl [00258]
[00259]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.76 (d, J = 4.5 Hz, 1H), 7.81 (d, J = 7.5 Hz, 1H), 7.66-7.62 (m, 1H), 7.39 (dd, J = 7.5, 2.0 Hz, 1H), 7.24 (d, J = 4.5 Hz, 1H), 4.33 (s, 3H). 1-102 Cl [00260]
[00261]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 8.75 (d, J = 4.5 Hz, 1H), 7.81 (d, J = 4.5 Hz, 1H), 7.36-7.30 (m, 1H), 7.17 (d, J = 2.5 Hz, 1H), 7.07-7.01 (m, 1H), 3.98 (s, 3H), 3.83 (s, 3H). 1-103 Cl [00262]
[00263]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.20 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 9.0 Hz, 1H), 7.23-7.15 (m, 1H), 7.05 (d, J = 3.0 Hz, 1H), 4.08 (s, 3H), 3.86 (s, 3H). 1-104 Cl [00264]
[00265]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.16 (d, J = 8.5 Hz, 1H), 6.92 (d, J = 2.5 Hz, 1H), 6.88 (d, J = 8.5, 2.5 Hz, 1H), 4.01 (s, 3H), 3.81 (s, 3H), 2.09 (s, 3H). 1-105 Cl [00266]
[00267]
1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.14 (d, J = 8.5 Hz, 1H), 6.70-6.59 (m, 2H), 3.97 (s, 3H), 3.81 (s, 3H), 3.73 (s, 3H). 1-106 Cl [00268]
[00269]
1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.81 (d, J = 5.0 Hz, 1H), 7.41-7.29 (m, 6H), 7.03-6.95 (m, 2H), 5.18 (s, 2H), 3.98 (s, 3H). 1-107 Cl [00270]
[00271]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 7.84-7.75 (m, 2H), 7.70 (dd, J = 7.5, 2.0 Hz, 1H), 7.50-7.44 (m, 2H), 7.42 (d, J = 7.5 Hz, 1H), 7.41-7.34 (m, 2H), 7.32-7.28 (m, 1H), 4.33 (s, 3H). 1-108 Cl [00272]
[00273]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.13 (d, J = 2.0 Hz, 2H), 7.96 (t, J = 2.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.73 (dd, J = 7.5, 2.0 Hz, 4H), 7.49 (t, J = 7.5 Hz, 4H), 7.43-7.35 (m, 2H), 4.33 (s, 3H). 1-109 Cl [00274]
[00275]
1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.67-7.60 (m, 2H), 7.55-7.42 (m, 1H), 3.99 (s, 3H). 1-110 Cl [00276]
[00277]
1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 7.48 (dd, J = 7.5, 1.5 Hz, 1H), 7.26 (t, J = 7.5 Hz, 1H), 4.00 (s, 3H), 3.92 (s, 3H). 1-111 Cl [00278]
[00279]
1H NMR (500 MHz, DMSO-d6) δ 12.19 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.04-7.98 (m, 2H), 7.87 (d, J = 5.0 Hz, 1H), 7.64 (t, J = 7.5 Hz, 1H), 7.53-7.42 (m, 3H), 7.36 (d, J = 8.5 Hz, 1H), 3.98 (s, 3H). 1-112 Cl [00280]
[00281]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.13-8.06 (m, 2H), 7.99 (d, J = 7.5 Hz, 1H), 7.82 (d, J = 5.0 Hz, 1H), 7.79- 7.73 (m, 2H), 7.62-7.56 (m, 2H), 4.01 (s, 3H). 1-113 Cl [00282]
[00283]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.91 (d, J = 5.5 Hz, 1H), 8.33 (dd, J = 7.5, 1.5 Hz, 1H), 8.22 (dd, J = 7.5, 1.5 Hz, 1H), 8.03-7.99 (m, 1H), 7.84 (d, J = 5.5 Hz, 1H), 7.53-7.50 (m, 1H), 7.37 (dd, J = 7.5, 8.0 Hz, 1H), 6.63-6.60 (m, 1H), 4.33 (s, 3H). 1-114 Cl [00284]
[00285]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 9.28 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.60 (d, J = 7.5 Hz, 1H), 8.18-8.10 (m, 2H), 7.88-7.78 (m, 3H), 4.33 (s, 3H). 1-115 Cl [00286]
[00287]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 8.94-8.86 (m, 2H), 8.78 (d, J = 5.5 Hz, 1H), 8.38 (s, 1H), 8.05-7.95 (m, 2H), 7.86 (d, J = 5.0 Hz, 1H), 7.74-7.61 (m, 4H), 4.33 (s, 3H). 1-116 Cl [00288]
[00289]
1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.30 (d d, J = 7.5, 1.5 Hz, 1H), 8.22 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.64-7.58 (m, 1H), 7.59-7.49 (m, 2H), 7.43 (t, J = 7.5 Hz, 1H), 4.01 (s, 3H). 1-117 Cl [00290]
[00291]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.01 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.13 (d, J = 1.5 Hz, 1H), 8.09-8.01 (m, 2H), 7.95 (dd, J = 7.5, 1.5 Hz, 1H), 7.81 (d, J = 5.0 Hz, 1H), 7.54 (dd, J = 7.5, 1.5 Hz, 1H), 7.48-7.41 (m, 1H), 7.37-7.32 (m, 1H), 4.33 (s, 3H). 1-118 Cl [00292]
[00293]
1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.51-8.38 (m, 3H), 7.98 (d, J = 5.0 Hz, 1H), 7.74 (s, 2H), 7.67-7.64 (m, 1H), 7.52 (s, 1H), 3.88 (s, 3H). 1-119 Cl [00294]
[00295]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.63 (d, J = 5.5 Hz, 1H), 8.22 (dd, J = 8.0, 2.0 Hz, 1H), 7.82 (t, J = 8.0 Hz, 1H), 7.69 (d, J = 5.5 Hz, 1H), 7.41-7.38 (m, 1H), 4.25 (s, 3H). 1-120 Cl [00296]
[00297]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.89 (d, J = 7.5, 1H), 8.75 (d, J = 5.5 Hz, 1H), 7.92 (t, J = 7.5 Hz, 1H), 7.82 (d, J = 5.5 Hz, 1H), 7.65 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-121 Cl [00298]
[00299]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 9.11 (s, 1H), 8.75 (d, J = 5.5 Hz, 1H), 8.54 (d, J = 8.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), 7.83 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-122 Cl [00300]
[00301]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.80 (d, J = 5.5 Hz, 1H), 8.71 (d, J = 5.5 Hz, 1H), 8.56 (s, 1H), 7.78 (d, J = 5.5 Hz, 1H), 7.53 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-123 Cl [00302]
[00303]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.76 (d, J = 5.5 Hz, 1H), 8.68 (dd, J = 8.0, 2.5 Hz, 1H), 8.22 (dd, J = 12.5, 2.5 Hz, 1H), 7.80 (d, J = 5.5 Hz, 1H), 7.62-7.58 (m, 1H), 4.33 (s, 3H). 1-124 Cl [00304]
[00305]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.86 (d, J = 2.5 Hz, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.69-8.68 (m, 1H), 8.11 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 7.57-7.55 (m, 1H), 4.00 (s, 3H). 1-125 Cl [00306]
[00307]
1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.56-8.49 (m, 1H), 8.48 (d, J = 5.0 Hz, 1H), 8.35 (s, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.36 (d, J = 5.0 Hz, 1H), 3.68 (s, 3H), 2.10 (s, 3H). 1-126 Cl [00308]
[00309]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 8.65 (s, 1H), 8.52 (s, 1H), 7.90 (s, 1H), 7.81 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 2.38 (s, 3H). 1-127 Cl [00310]
[00311]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.27 (dd, J = 5.5, 1.5 Hz, 1H), 8.18-8.16 (m, 1H), 7.78-7.75 (m, 1H), 7.72 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-128 Cl [00312]
[00313]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.77-8.71 (m, 2H), 8.40-8.36 (m, 2H), 7.88 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-129 Cl [00314]
[00315]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.80 (d, J = 4.5 Hz, 1H), 8.72 (d, J = 2.5 Hz, 1H), 8.20-8.18 (m, 1H), 7.82 (d, J = 4.5 Hz, 1H), 7.69 (d, J = 8.0 Hz, 1H), 3.97 (s, 3H). 1-130 Cl [00316]
[00317]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.35 (dd, J = 5.0, 2.0 Hz, 1H), 8.07-8.02 (m, 1H), 7.92-7.85 (m, 2H), 4.33 (s, 3H). 1-131 Cl [00318]
[00319]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.81 (d, J = 1.5 Hz, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.02 (dd, J = 8.0, 1.5 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H). 1-132 Cl [00320]
[00321]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.83 (d, J = 5.5 Hz, 1H), 8.75 (d, J = 7.5 Hz, 1H), 8.18 (dd, J = 7.5, 7.5 Hz, 1H), 7.98 (d, J = 5.5 Hz, 1H), 7.18 (dd, J = 12.5, 7.5 Hz, 1H), 4.33 (s, 3H). 1-133 Cl [00322]
[00323]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 9.25 (s, 1H), 9.08 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.68 (s, 1H), 8.00 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-134 Cl [00324]
[00325]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.98 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.24 (d, J = 8.0 Hz, 1H), 7.99 (d, J = 5.5 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H). 1-135 Cl [00326]
[00327]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.38-8.33 (m, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.16-7.11 (m, 1H), 4.33 (s, 3H). 1-136 Cl [00328]
[00329]
1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.14 (s, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.26 (d, J = 6.0 Hz, 1H), 3.99 (s, 3H), 2.17 (s, 3H). 1-137 Cl [00330]
[00331]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.85 (d, J = 4.5 Hz, 1H), 8.28 (dd, J = 11.0, 8.0 Hz, 1H), 7.52 (d, J = 4.5 Hz, 1H), 6.88 (dd, J = 8.0, 7.0 Hz, 1H), 4.32 (s, 3H), 2.79 (s, 3H). 1-138 Cl [00332]
[00333]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.88-8.82 (m, 2H), 7.54-7.47 (m, 2H), 4.32 (s, 3H), 2.37 (s, 3H). 1-139 Cl [00334]
[00335]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.84 (d, J = 4.5 Hz, 1H), 8.36 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.33 (d, J = 4.5 Hz, 1H), 4.32 (s, 3H). 1-140 Cl [00336]
[00337]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.18 (dd, J = 8.0, 6.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H). 1-141 Cl [00338]
[00339]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.86 (d, J = 4.5 Hz, 1H), 8.69 (dd, J = 5.0, 1.5 Hz, 1H), 8.26 (dd, J = 8.0, 1.5 Hz, 1H), 7.67 (dd, J = 8.0, 5.0 Hz, 1H), 7.36 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-142 Cl [00340]
[00341]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 9.07 (d, J = 2.0 Hz, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.46-8.38 (m, 1H), 8.09 (d, J = 8.0 Hz, 1H), 7.91 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H). 1-143 Cl [00342]
[00343]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.19 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.63 (d, J = 2.5 Hz, 1H), 8.21-8.08 (m, 1H), 7.88 (d J = 5.0 Hz, 1H), 7.08 (d, J = 8.5 Hz, 1H), 4.11 (s, 3H), 4.03 (s, 3H). 1-144 Cl [00344]
[00345]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.59 (d, J = 1.5 Hz, 1H), 8.03 (dd, J = 8.0, 1.5 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.09 (d, J = 8.0 Hz, 1H), 4.33 (q, J = 8.0 Hz, 2H), 4.33 (s, 3H), 1.28 (t, J = 8.0 Hz, 3H). 1-145 Cl [00346]
[00347]
1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.84 (d, J = 4.5 Hz, 1H), 8.38 (d, J = 1.5 Hz, 1H), 8.04-7.95 (m, 2H), 7.46 (t, J = 1.5 Hz, 1H), 6.18 (s, 2H), 4.33 (s, 3H). 1-146 Cl [00348]
[00349]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.14 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.53 (d, J = 2.5 Hz, 1H), 8.01 (dd, J = 9.0, 2.5 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.03 (d, J = 9.0 Hz, 1H), 4.03 (s, 3H), 3.73 (t, J = 5.0 Hz, 4H), 3.60 (t, J = 5.0 Hz, 4H). 1-147 Cl [00350]
[00351]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.66 (d, J = 5.0 Hz, 2H), 8.04 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-148 Cl [00352]
[00353]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.78 (d, J = 5.5 Hz, 1H), 8.53 (s, 1H), 8.29 (d, J = 5.5 Hz, 1H), 8.00 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-149 Cl [00354]
[00355]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.27 (d, J = 5.0 Hz, 1H), 8.06-7.97 (m, 2H), 7.84 (dd, J = 5.0, 1.0 Hz, 1H), 4.33 (s, 3H). 1-150 Cl [00356]
[00357]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 8.0 Hz, 1H), 8.33 (d, J = 4.5 Hz, 1H), 7.73 (dd, J = 8.0, 4.5 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-151 Cl [00358]
[00359]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.42-8.34 (m, 2H), 8.06-7.96 (m, 2H), 4.33 (s, 3H). 1-152 Cl [00360]
[00361]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.40 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-153 Cl [00362]
[00363]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.49 (s, 2H), 8.11 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-154 Cl [00364]
[00365]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.94 (dd, J = 7.5, 7.5 Hz, 1H), 8.89 (d, J = 5.5 Hz, 1H), 8.01 (d, J = 5.5 Hz, 1H), 7.68 (dd, J = 12.0, 7.5 Hz, 1H), 4.33 (s, 3H). 1-155 Cl [00366]
[00367]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.94 (d, J = 7.5 Hz, 1H), 8.89 (d, J = 5.5 Hz, 1H), 8.34 (d, J = 7.5 Hz, 1H), 8.01 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-156 Cl [00368]
[00369]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 9.40 (s, 2H), 9.35 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-157 Cl [00370]
[00371]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 9.27 (s, 2H), 8.79 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-158 Cl [00372]
[00373]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 9.45 (d, J = 7.5 Hz, 2H), 8.89 (d, J = 5.5 Hz, 1H), 7.98 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-159 Cl [00374]
[00375]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 9.01 (s, 2H), 8.90 (d, J = 5.5 Hz, 1H), 7.96 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-160 Cl [00376]
[00377]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.63 (s, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.11 (s, 2H), 4.00 (s, 3H). 1-161 Cl [00378]
[00379]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 9.50 (s, 2H), 8.89 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.85 (s, 3H). 1-162 Cl [00380]
[00381]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.34 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.74 (s, 1H), 7.31 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 3.98 (s, 3H), 3.84 (s, 3H). 1-163 Cl [00382]
[00383]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 9.25 (s, 2H), 8.86 (d, J = 5.5 Hz, 1H), 8.00 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-164 Cl [00384]
[00385]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.88 (d, J = 5.5 Hz, 1H), 8.84 (d, J = 12.5, 2.5 Hz, 2H), 7.99 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-165 Cl [00386]
[00387]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 9.10 (d, J = 5.0 Hz, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.02 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-166 Cl [00388]
[00389]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H), 7.50 (d, J = 12.5 Hz, 2H), 4.33 (s, 3H). 1-167 Cl [00390]
[00391]
1H NMR (500 MHz, DMSO-d6) δ 13.15 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.22 (s, 2H), 7.16 (d, J = 5.0 Hz, 1H), 3.70 (s, 3H). 1-168 Cl [00392]
[00393]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.63 (s, 1H), 8.25 (s, 1H), 7.68 (d, J = 5.0 Hz, 1H), 4.12 (s, 3H), 4.03 (s, 3H). 1-169 Cl [00394]
[00395]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.01 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.20 (s, 1H), 7.59 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 3.82 (s, 3H), 2.28 (s, 3H). 1-170 Cl [00396]
[00397]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.99 (d, J = 5.0 Hz, 1H), 7.67 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.94 (s, 3H), 2.34 (s, 3H). 1-171 Cl [00398]
[00399]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.53 (s, 1H), 12.03 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H), 7.40 (s, 1H), 4.33 (s, 3H), 2.31 (s, 3H). 1-172 Cl [00400]
[00401]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.02 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.53 (s, 1H), 8.15 (s, 1H), 7.56 (d, J = 5.0 Hz, 1H), 4.21-4.15 (m, 2H), 4.00 (s, 3H), 1.40 (t, J = 7.0 Hz, 3H). 1-173 Cl [00402]
[00403]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 1.5 Hz, 1H), 7.47 (d, J = 5.0 Hz, 1H), 6.91 (d, J = 1.5 Hz, 1H), 4.33 (s, 3H), 4.20 (t, J = 8.0 Hz, 2H), 2.00 (m, 2H), 0.95 (t, J = 8.0 Hz, 3H). 1-174 Cl [00404]
[00405]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.91 (d, J = 5.5 Hz, 1H), 7.95 (t, J = 65.0 Hz, 1H), 7.71 (d, J = 5.5 Hz, 1H), 7.67 (s, 1H), 7.06 (s, 1H)), 4.33 (s, 3H). 1-175 Cl [00406]
[00407]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.13 (s, 1H), 8.95-8.69 (m, 2H), 8.30 (d, J = 5.5 Hz, 1H), 7.68 (s, 1H), 7.42-7.29 (m, 5H), 5.53 (s, 2H), 4.11 (s, 3H). 1-176 Cl [00408]
[00409]
1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.66-8.59 (m, 2H), 8.22 (s, 1H), 7.60 (d, J = 5.5 Hz, 1H), 5.65-5.60 (m, 1H), 4.00 (s, 3H), 3.51- 3.41 (m, 2H), 1.63 (d, J = 6.0 Hz, 3H), 1.06-0.97 (m, 3H). 1-177 Cl [00410]
[00411]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.56 (s, 1H), 12.13 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.30 (d, J = 2.5 Hz, 1H), 7.89 (d, J = 2.5 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H). 1-178 Cl [00412]
[00413]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 2.5 Hz, 1H), 7.61-7.44 (m, 1H), 6.67 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 3.83 (s, 3H). 1-179 Cl [00414]
[00415]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.98 (d, J = 4.5 Hz, 1H), 7.51 (d, J = 4.5 Hz, 1H), 6.55 (s, 1H), 4.33 (s, 3H), 4.00 (s, 3H), 2.35 (s, 3H). 1-180 Cl [00416]
[00417]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 6.68 (s, 1H), 4.33 (s, 3H), 4.02 (s, 3H). 1-181 Cl [00418]
[00419]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.96-7.73 (t, J = 6.5 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 7.64 (d, J = 2.5 Hz, 1H), 6.73 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-182 Cl [00420]
[00421]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.10 (d, J = 5.0 Hz, 1H), 7.61 (d, J = 2.5 Hz, 1H), 6.68 (d, J = 2.5 Hz, 1H), 6.12 (t, J = 6.5 Hz, 1H), 4.33 (s, 3H), 3.90-3.77 (m, 2H), 2.47-2.36 (m, 1H), 2.08- 1.95 (m, 2H), 1.81-1.69 (m, 1H), 1.59-1.55 (m, 2H). 1-183 Cl [00422]
[00423]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.16 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.66 (s, 1H), 7.98-7.88 (m, 1H), 7.78 (d, J = 2.0 Hz, 1H), 7.25 (d, J = 2.0 Hz, 1H), 4.20 (s, 3H). 1-184 Cl [00424]
[00425]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.10-8.04 (m, 2H), 7.25 (d, J = 2.5 Hz, 1H), 6.98 (t, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-185 Cl [00426]
[00427]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 9.25 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 5.0 Hz, 1H), 7.29 (d, J = 2.5 Hz, 1H), 7.22 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-186 Cl [00428]
[00429]
1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.20 (dd, J = 3.0, 1.5 Hz, 1H), 7.74-7.58 (m, 3H), 4.01 (s, 3H). 1-187 Cl [00430]
[00431]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 2.5 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 6.92 (d, J = 2.5 Hz, 1H), 4.00 (s, 3H), 2.38 (s, 3H). 1-188 Cl [00432]
[00433]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.97 (s, 1H), 7.67 (d, J = 5.0 Hz, 1H), 7.42 (s, 1H), 4.03 (s, 3H), 2.29 (s, 3H). 1-189 Cl [00434]
[00435]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.99 (d, J = 5.0 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 7.08 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-190 Cl [00436]
[00437]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 9.87 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 8.10 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 2.5 Hz, 1H), 7.81 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-191 Cl [00438]
[00439]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.11 (d, J = 2.5 Hz, 1H), 7.82 (d, J = 2.5 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.50 (s, 3H). 1-192 Cl [00440]
[00441]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.59-7.51 (m, 2H), 4.33 (s, 3H), 4.26 (s, 1H). 1-193 Cl [00442]
[00443]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.91 (d, J = 5.5 Hz, 1H), 8.45 (s, 1H), 8.09 (s, 1H), 7.91 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-194 CH.sub.3 [00444]
[00445]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.69 (d, J = 4.5 Hz, 1H), 7.60-7.52 (m, 2H), 7.14-7.03 (m, 3H), 4.33 (s, 3H), 2.35 (s, 3H). 1-195 F [00446]
[00447]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.44 (dd, J = 5.0, 1.5 Hz, 1H), 8.08-8.01 (m, 2H), 7.83 (dd, J = 7.5, 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H). 1-196 Br [00448]
[00449]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.80 (d, J = 5.5 Hz, 1H), 7.96 (dd, J = 7.5, 7.0 Hz, 2H), 7.72 (d, J = 5.5 Hz, 1H), 7.33 (dd, J = 12.0, 7.0 Hz, 2H), 4.33 (s, 3H). 1-197 [00450]
[00451]
[00452]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.54-7.45 (m, 2H), 7.11-7.03 (m, 2H), 7.00 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 3.16-3.11 (m, 1H), 1.25 (d, J = 6.5 Hz, 6H). 1-198 CF.sub.3 [00453]
[00454]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.87 (d, J = 4.5 Hz, 1H), 7.64-7.56 (m, 2H), 7.13 (d, J = 4.5 Hz, 1H), 7.11-7.03 (m, 2H), 4.35 (s, 3H). 1-199 [00455]
[00456]
[00457]
.sup.1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.61-7.53 (m, 4H), 7.42 (t, J = 7.5 Hz, 1H), 7.40 (d, J = 7.5 Hz, 1H), 7.37-7.29 (m, 2H), 7.11-7.03 (m, 2H), 4.29 (s, 3H). 1-200 [00458]
[00459]
[00460]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.71-7.63 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H) 4.34 (s, 3H), 3.79 (s, 3H). 1-201 [00461]
[00462]
[00463]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.71-7.64 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.34-4.06 (m, 2H), 4.34 (s, 3H), 1.61 (t, J = 8.0 Hz, 3H). 1-202 [00464]
[00465]
[00466]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 11.93 (s, 1H), 8.67 (d, J = 4.5 Hz, 1H), 7.72-7.64 (m, 2H), 7.42 (d, J = 4.5 Hz, 1H), 7.11-7.03 (m, 2H), 4.46-4.39 (m, 2H), 4.34 (s, 3H). 1-203 [00467]
[00468]
[00469]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.60 (d, J = 5.5 Hz, 1H), 8.02 (dd, J = 7.5, 7.5 Hz, 2H), 7.60 (d, J = 5.5 Hz, 1H), 7.32 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 2.21 (s, 3H). 1-204 [00470]
[00471]
[00472]
.sup.1H NMR (500 MHz, DMSO-d6) δ 11.82 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.64-7.56 (m, 2H), 7.24 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.33 (s, 3H), 2.97-2.89 (m, 2H), 1.28 (t, J = 8.0 Hz, 3H). 1-205 [00473]
[00474]
[00475]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.87 (d, J = 5.5 Hz, 1H), 7.98 (dd, J = 7.5, 7.5 Hz, 2H), 7.65 (d, J = 5.5 Hz, 1H), 7.33 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 2.61 (s, 3H). 1-206 [00476]
[00477]
[00478]
.sup.1H NMR (500 MHz, DMSO-6) δ 12.02 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 7.66-7.59 (m, 2H), 7.28 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.30 (s, 3H), 3.25-3.16 (m, 2H), 1.35 (t, J = 8.0 Hz, 3H). 1-207 [00479]
[00480]
[00481]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 9.02 (d, J = 5.5 Hz, 1H), 8.12 (dd, J = 7.5, 7.5 Hz, 2H), 7.78 (d, J = 5.5 Hz, 1H), 7.31 (dd, J = 12.0, 7.5 Hz, 2H), 4.33 (s, 3H), 2.94 (s, 3H). 1-208 [00482]
[00483]
[00484]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.48 (d, J = 4.5 Hz, 1H), 7.57-7.47 (m, 3H), 7.11-7.03 (m, 2H), 4.33 (s, 3H), 2.89 (s, 6H). 1-209 [00485]
[00486]
[00487]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.49 (d, J = 5.5 Hz, 1H), 8.05 (dd, J = 7.5, 7.5 Hz, 2H), 7.89 (d, J = 5.5 Hz, 1H), 7.27 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 2.35 (s, 6H). 1-210 Et [00488]
[00489]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.58 (d, J = 5.5 Hz, 1H), 7.96-7.88 (m, 2H), 7.40 (d, J = 5.5 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 2.70 (q, J = 8.0 Hz, 2H), 1.07 (t, J = 8.0 Hz, 3H). 1-211 [00490]
[00491]
[00492]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.54 (d, J = 5.5 Hz, 1H), 8.06-7.98 (m, 2H), 7.53 (d, J = 5.5 Hz, 1H), 7.35-7.27 (m, 2H), 5.02 (s, 2H), 4.33 (s, 3H). 1-212 NO.sub.2 [00493]
[00494]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 8.78 (d, J = 5.5 Hz, 1H), 7.92 (dd, J = 7.5, 7.0 Hz, 2H), 7.79 (d, J = 5.5 Hz, 1H), 7.27 (dd, J = 11.0, 7.5 Hz, 2H), 4.33 (s, 3H). 1-213 CN [00495]
[00496]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.80 (d, J = 5.5 Hz, 1H), 7.98 (dd, J = 7.5, 7.0 Hz, 2H), 7.72 (d, J = 5.5 Hz, 1H), 7.31 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H). 1-214 [00497]
[00498]
[00499]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 4.33 (s, 3H), 3.28 (s, 3H). 1-215 [00500]
[00501]
[00502]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.97-7.90 (m, 2H), 7.79 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.64 (q, J = 7.0 Hz, 1H), 4.33 (s, 3H), 3.23 (s, 3H), 1.36 (d, J = 7.0 Hz, 3H). 1-216 [00503]
[00504]
[00505]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.97-7.90 (m, 2H), 7.79 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.36 (t, J = 8.0 Hz, 1H), 4.33 (s, 3H), 3.22 (s, 3H), 1.77-1.62 (m, 2H), 0.85 (t, J = 8.0 Hz, 3H). 1-217 [00506]
[00507]
[00508]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.61 (d, J = 5.0 Hz, 1H), 7.93-7.85 (m, 2H), 7.40 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 3.48 (t, J = 7.5 Hz, 2H), 3.23 (s, 3H), 2.75 (t, J = 7.5 Hz, 2H). 1-218 [00509]
[00510]
[00511]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.0.1 (dd, J = 7.5, 7.0 Hz, 2H), 7.47 (d, J = 5.5 Hz, 1H), 7.27 (dd, J = 12.0, 7.5 Hz, 2H), 6.59 (dd, J = 16.5, 10.5 Hz, 1H), 5.55 (dd, J = 13.5, 10.5 Hz, 1H), 5.36 (dd, J = 16.5, 13.5 Hz, 1H), 4.33 (s, 3H). 1-219 [00512]
[00513]
[00514]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.45 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 5.69-5.65 (m, 1H), 5.06-4.92 (m, 2H), 4.33 (s, 3H), 3.33-3.30 (m, 2H). 1-220 [00515]
[00516]
[00517]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.72 (d, J = 5.5 Hz, 1H), 8.07 (dd, J = 7.5, 7.5 Hz, 2H), 7.57 (d, J = 5.5 Hz, 1H), 7.35 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 4.31 (s, 1H). 1-221 [00518]
[00519]
[00520]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 2.25 (p, J = 7.0 Hz, 1H), 0.91- 0.81 (m, 2H), 0.70-0.66 (m, 2H). 1-222 [00521]
[00522]
[00523]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.00-7.92 (m, 2H), 7.35-7.27 (m, 3H), 4.90 (s, 1H), 4.33 (s, 3H). 1-223 [00524]
[00525]
[00526]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 9.02 (d, J = 5.5 Hz, 1H), 7.99 (dd, J = 7.5, 7.5 Hz, 2H), 7.78 (d, J = 5.5 Hz, 1H), 7.55 (dd, J = 7.5, 7.0 Hz, 2H), 7.35 (dd, J = 11.5, 7.5 Hz, 2H), 7.23 (dd, J = 11.0, 7.5 Hz, 2H), 4.33 (s, 3H). 1-224 Cl [00527]
[00528]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 9.17 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 6.50 (d, J = 2.5 Hz, 1H), 6.10 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H), 3.63 (s, 3H). 1-225 Cl [00529]
[00530]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.82 (d, J = 5.0 Hz, 1H), 7.02 (s, 1H), 6.91 (d, J = 2.0 Hz, 1H), 6.61 (d, J = 2.0 Hz, 1H), 4.37 (q, J = 9.0 Hz, 2H), 4.33 (s, 3H). 1-226 Cl [00531]
[00532]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.09 (s, 1H), 7.93 (d, J = 5.0 Hz, 1H), 7.70 (s, 1H), 4.33 (s, 3H). 1-227 Cl [00533]
[00534]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.13 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 2.5 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.36 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-228 Cl [00535]
[00536]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 9.19 (s, 1H), 8.92 (d, J = 5.5 Hz, 1H), 8.03 (s, 1H), 7.94 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-229 Cl [00537]
[00538]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 9.19 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.12 (s, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-230 Cl [00539]
[00540]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.93 (d, J = 5.5 Hz, 1H), 8.04 (d, J = 2.5 Hz, 1H), 7.96 (d, J = 5.5 Hz, 1H), 7.50 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-231 Cl [00541]
[00542]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.72 (s, 1H), 7.98 (s, 1H), 7.92 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-232 Cl [00543]
[00544]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 2.5 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-233 Cl [00545]
[00546]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.90 (d, J = 5.5 Hz, 1H), 7.95 (d, J = 2.5 Hz, 1H), 7.39 (d, J = 5.5 Hz, 1H), 7.05 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H), 3.92 (s, 3H). 1-234 Cl [00547]
[00548]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 5.0 Hz, 1H), 7.73 (s, 1H), 7.67 (s, 1H), 4.33 (s, 3H), 3.79 (s, 3H). 1-235 Cl [00549]
[00550]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 7.61 (s, 1H), 6.70 (t, J = 65 Hz, 1H), 4.33 (s, 3H), 3.54 (s, 3H). 1-236 Cl [00551]
[00552]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.18 (s, 1H), 7.75 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-237 Cl [00553]
[00554]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.14 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.45 (s, 1H), 7.77 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-238 Cl [00555]
[00556]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 7.69 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-239 Cl [00557]
[00558]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.74 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-240 Cl [00559]
[00560]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.27 (s, 1H), 7.86 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-241 Cl [00561]
[00562]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.18 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.35-4.25 (m, 5H), 2.51 (s, 3H), 1.39 (t, J = 8.0 Hz, 3H). 1-242 Cl [00563]
[00564]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 7.82 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-243 Cl [00565]
[00566]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.19 (s, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H). 1-244 Cl [00567]
[00568]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 9.25 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-245 Cl [00569]
[00570]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.16 (s, 1H), 7.76 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-246 Cl [00571]
[00572]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.36 (s, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.19 (s, 3H). 1-247 Cl [00573]
[00574]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.16 (s, 3H), 3.67 (s, 2H). 1-248 Cl [00575]
[00576]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 7.91 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-249 Cl [00577]
[00578]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.89 (d, J = 5.5 Hz, 1H), 7.93 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H), 2.49 (s, 3H). 1-250 Cl [00579]
[00580]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 9.17 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 1.50 (p, J = 8.0 Hz, 1H), 1.19-1.15 (m, 2H), 1.05-1.01 (m, 2H). 1-251 Cl [00581]
[00582]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.27 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-252 Cl [00583]
[00584]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.20 (s, 3H) 1-253 Cl [00585]
[00586]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 7.96 (s, 1H), 7.72 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-254 Cl [00587]
[00588]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-255 Cl [00589]
[00590]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.30 (s, 1H), 7.67 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.29 (s, 3H). 1-256 Cl [00591]
[00592]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-257 Cl [00593]
[00594]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-258 Cl [00595]
[00596]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-259 Cl [00597]
[00598]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-260 Cl [00599]
[00600]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 10.15 (s, 2H), 8.82 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-261 Cl [00601]
[00602]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 9.87 (d, J = 1.5 Hz, 1H), 9.50 (d, J = 5.0 Hz, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.29 (dd, J = 5.0, 1.5 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-262 Cl [00603]
[00604]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 9.35 (dd, J = 5.0, 1.5 Hz, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.68 (dd, J = 7.5, 1.5 Hz, 1H), 7.99- 7.92 (m, 2H), 4.33 (s, 3H). 1-263 Cl [00605]
[00606]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 9.06 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.78 (d, J = 5.0 Hz, 1H), 8.00 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-264 Cl [00607]
[00608]
1-265 Cl [00609]
[00610]
1-266 Cl [00611]
[00612]
1-267 Cl [00613]
[00614]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.94 (dd, J = 7.5, 1.5 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 7.59 (dd, J = 7.5, 1.5 Hz, 1H), 7.53 (s, 1H), 7.40 (td, J = 7.5, 1.5 Hz, 1H), 7.35 (td, J = 7.5, 1.5 Hz, 1H), 4.33 (s, 3H). 1-268 Cl [00615]
[00616]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 2.0 Hz, 1H), 7.92 (d, J = 1.5 Hz, 1H), 7.81 (dd, J = 7.5, 1.5 Hz, 1H), 7.76-7.69 (m, 2H), 7.04 (d, J = 2.0, 1H), 4.33 (s, 3H). 1-269 Cl [00617]
[00618]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 7.66 (d, J = 2.0 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 7.47 (d, J = 1.5 Hz, 1H), 7.17 (d, J = 1.5 Hz, 1H), 6.91 (d, J = 2.0 Hz, 1H), 4.33 (s, 3H), 3.02 (s, 6H). 1-270 Cl [00619]
[00620]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.03 (s, 1H), 9.32 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.60 (d, J = 1.5 Hz, 1H), 8.08 (d, J = 7.5 Hz, 1H), 7.95 (dd, J = 7.5, 1.5 Hz, 1H), 7.72 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-271 Cl [00621]
[00622]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.18 (dd, J = 7.5, 1.5 Hz, 1H), 8.08 (dd, J = 7.5, 1.5 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.58-7.54 (m, 1H), 7.50-7.46 (m, 1H), 4.33 (s, 3H). 1-272 Cl [00623]
[00624]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 9.46 (s, 1H), 8.99-8.95 (m, 2H), 8.73 (d, J = 5.0 Hz, 1H), 7.62 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-273 Cl [00625]
[00626]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.58 (s, 1H), 8.10 (d, J = 7.5 Hz, 1H), 7.80 (d, J = 7.5 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.84 (s, 3H). 1-274 Cl [00627]
[00628]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.53 (s, 1H), 7.98 (d, J = 1.5 Hz, 1H), 7.73 (d, J = 7.5 Hz, 1H), 7.67 (dd, J = 7.5, 1.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-275 Cl [00629]
[00630]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 7.98-7.89 (m, 2H), 7.87-7.84 (m, 1H), 7.64-7.59 (m, 2H), 4.33 (s, 3H). 1-276 Cl [00631]
[00632]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 1.5 Hz, 1H), 7.37 (d, J = 1.5 Hz, 1H), 5.32 (s, 1H), 4.50 (s, 2H), 4.33 (s, 3H), 4.02 (s, 3H), 2.34 (s, 3H). 1-277 Cl [00633]
[00634]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 8.17 (dd, J = 7.5, 1.5 Hz, 1H), 7.83 (dd, J = 7.5, 1.5 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.37 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H), 3.79 (s, 3H). 1-278 Cl [00635]
[00636]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.28 (d, J = 1.5 Hz, 1H), 8.16 (d, J = 7.5, 1.5 Hz, 1H), 8.05 (s, 1H), 7.80 (d, J = 7.5 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.79 (s, 3H). 1-279 Cl [00637]
[00638]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 5.0 Hz, 1H), 7.64-7.54 (m, 2H), 7.47 (d, J = 1.5 Hz, 1H), 4.33 (s, 3H), 2.51 (s, 3H). 1-280 Cl [00639]
[00640]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.39 (s, 1H), 8.07 (dd, J = 7.5, 1.5 Hz, 1H), 7.64 dd, J = 7.5, 1.5 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.45 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-281 Cl [00641]
[00642]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.39 (d, J = 7.5 Hz, 1H), 7.88-7.79 (m, 2H), 7.64 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-282 Cl [00643]
[00644]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 9.27 (d, J = 1.5 Hz, 1H), 8.96 (d, J = 5.0 Hz, 1H), 8.69 (d, J = 1.5 Hz, 1H), 8.15-8.05 (m, 2H), 7.87 (d, J = 5.0 Hz, 1H), 7.69 (td, J = 7.5, 1.5 Hz, 1H), 7.58 (td, J = 7.5, 1.5 Hz, 1H), 4.33 (s, 3H). 1-283 Cl [00645]
[00646]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.19 (s, 1H), 12.08 (s, 1H), 9.79 (d, J = 1.5 Hz, 1H), 9.21 (d, J = 1.5 Hz, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.44 (dd, J = 7.5, 1.5 Hz, 1H), 8.33 (dd, J = 7.5, 1.5 Hz, 1H), 8.12 (t, J = 7.5 Hz, 1H), 7.85 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-284 Cl [00647]
[00648]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 9.73 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.49-8.41 (m, 2H), 8.35 (dd, J = 7.5, 1.5 Hz, 1H), 7.93 (d, J = 7.5 Hz, 1H), 7.74 (t, J = 7.5 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-285 Cl [00649]
[00650]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 9.69 (s, 1H), 9.04 (d, J = 5.0 Hz, 1H), 8.43 (d, J = 1.5 Hz, 1H), 8.07-7.97 (m, 3H), 4.33 (s, 3H), 3.85 (s, 1H). 1-286 Cl [00651]
[00652]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 9.13 (d, J = 5.5 Hz, 1H), 8.91-8.83 (m, 2H), 8.23 (dd, J = 7.5, 1.5 Hz, 2H), 7.93 (t, J = 7.5 Hz, 1H), 7.65 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-287 Cl [00653]
[00654]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.91-8.86 (m, 3H), 8.74 (d, J = 1.5 Hz, 1H), 8.29-8.21 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-288 Cl [00655]
[00656]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.28 (dd, J = 7.5, 1.5 Hz, 1H), 7.93 (d, J = 7.5 Hz, 1H), 7.80 (d, J = 1.5 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.05 (s, 1H), 4.33 (s, 3H), 3.62 (s, 3H), 3.55 (s, 2H), 2.18 (s, 3H). 1-289 Cl [00657]
[00658]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.77 (d, J = 1.5 Hz, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.24 (dd, J = 7.5, 1.5 Hz, 1H), 7.74-7.68 (m, 2H), 7.17 (d, J = 7.5 Hz, 1H), 6.63 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H), 3.79 (s, 3H). 1-290 Cl [00659]
[00660]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.00-7.92 (m, 2H), 7.73 (dd, J = 7.5, 1.5 Hz, 1H), 7.47 (td, J = 7.5, 1.5 Hz, 1H), 7.31 (td, J = 7.5, 1.5 Hz, 1H), 7.14 (s, 1H), 4.33 (s, 3H), 3.82 (s, 3H). 1-291 Cl [00661]
[00662]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.97 (d, J = 7.5 Hz, 1H), 7.95-7.88 (m, 3H), 7.39 (dd, J = 7.5, 1.5 Hz, 1H), 4.33 (s, 3H). 1-292 Cl [00663]
[00664]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.04 (dd, J = 7.5, 1.5 Hz, 1H), 7.91 (dd, J = 7.5, 1.5 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 7.65 (d, J = 2.5 Hz, 1H), 7.56 (t, J = 7.5 Hz, 1H), 7.44 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-293 Cl [00665]
[00666]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.07-7.97 (m, 2H), 7.75 (d, J = 5.0 Hz, 1H), 7.66-7.56 (m, 2H), 7.50 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-294 Cl [00667]
[00668]
1-295 Cl [00669]
[00670]
1-296 Cl [00671]
[00672]
1-297 Cl [00673]
[00674]
1-298 Cl [00675]
[00676]
1-299 Cl [00677]
[00678]
1-300 Cl [00679]
[00680]
1-301 Cl [00681]
[00682]
1-302 Cl [00683]
[00684]
1-303 Cl [00685]
[00686]
1-304 Cl [00687]
[00688]
1-305 Cl [00689]
[00690]
1-306 Cl [00691]
[00692]
1-307 Cl [00693]
[00694]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.65-7.57 (m, 2H), 7.25 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.40-4.32 (m, 2H), 1.50 (t, J = 8.0 Hz, 3H). 1-308 Cl [00695]
[00696]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.25 (t, J = 5.0 Hz, 2H), 1.74-1.70 (m, 2H), 0.89 (t, J = 8.0 Hz, 3H). 1-309 Cl [00697]
[00698]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.56 (s, 1H), 12.06 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.05- 7.97 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H). 1-310 Cl [00699]
[00700]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.49 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.07-6.04 (m, 1H), 5.41-5.32 (m, 1H), 5.27- 5.16 (m, 1H), 4.43-4.37 (m, 2H). 1-311 Cl [00701]
[00702]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 5.57 (s, 2H), 3.35 (s, 3H). 1-312 Cl [00703]
[00704]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.10 (t, J = 8.0 Hz, 2H), 2.92 (t, J = 8.0 Hz, 2H), 2.09 (s, 3H). 1-313 Cl [00705]
[00706]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 5.05 (s, 2H), 3.78 (s, 3H). 1-314 Cl [00707]
[00708]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.07-7.99 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 7.59-7.53 (m, 4H), 7.52-7.49 (m, 1H), 7.35-7.27 (m, 2H). 1-315 Cl [00709]
[00710]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.06-7.99 (m, 2H), 7.69-7.60 (m, 3H), 7.57-7.54 (m, 2H), 7.35-7.27 (m, 2H). 1-316 Cl [00711]
[00712]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.59 (d, J = 5.0 Hz, 1H), 7.41 (dd, J = 7.5, 1.5 Hz, 2H), 7.35-7.27 (m, 2H), 7.08-7.02 (m, 2H), 5.45 (s, 2H). 1-317 Cl CH.sub.3 [00713]
1-318 Cl [00714]
[00715]
1-319 Cl [00716]
[00717]
1-320 Cl [00718]
[00719]
1-321 Cl [00720]
[00721]
1-322 Cl [00722]
[00723]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 7.64 (d, J = 5.0 Hz, 1H), 6.14-6.07 (m, 1H), 3.91 (s, 3H), 3.36-3.30 (m, 2H), 3.05 (t, J = 7.0, Hz, 2H), 2.60 (t, J = 7.0 Hz, 2H), 2.20 (s, 3H). 1-323 Cl [00724]
[00725]
1-324 Cl [00726]
[00727]
1-325 Cl [00728]
[00729]
1-326 Cl [00730]
[00731]
1-327 Cl [00732]
[00733]
1-328 Cl [00734]
[00735]
1-329 Cl [00736]
[00737]
1-330 Cl [00738]
[00739]
1-331 Cl [00740]
[00741]
1-332 Cl [00742]
[00743]
1-333 Cl [00744]
[00745]
1-334 Cl [00746]
[00747]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.23 (s, 1H), 7.64- 7.57 (m, 2H), 7.25 (d, J = 5.0 Hz, 1H), 7.11- 7.03 (m, 2H), 3.95 (s, 3H). 1-335 Cl [00748]
[00749]
1-336 Cl [00750]
[00751]
1-337 Cl [00752]
[00753]
1-338 Cl [00754]
[00755]
1-339 Cl [00756]
[00757]
1-340 Cl [00758]
[00759]
1-341 Cl [00760]
[00761]
1-342 Cl [00762]
[00763]
1-343 Cl [00764]
[00765]
1-344 Cl [00766]
[00767]
1-345 Cl [00768]
[00769]
1-346 Cl [00770]
[00771]
1-347 Cl [00772]
[00773]
1-348 Cl [00774]
[00775]
1-349 Cl [00776]
[00777]
1-350 Cl [00778]
[00779]
1-351 Cl [00780]
[00781]
1-352 Cl [00782]
[00783]
1-353 Cl [00784]
[00785]
1-354 Cl [00786]
[00787]
1-355 Cl [00788]
[00789]
1-356 Cl [00790]
[00791]
1-357 Cl [00792]
[00793]
1-358 Cl [00794]
[00795]
1-359 Cl [00796]
[00797]
1-360 Cl [00798]
[00799]
1-361 Cl [00800]
[00801]
1-362 Cl [00802]
[00803]
1-363 Cl [00804]
[00805]
1-364 Cl [00806]
[00807]
1-365 Cl [00808]
[00809]
1-366 Cl [00810]
[00811]
1-367 Cl [00812]
[00813]
1-368 Cl [00814]
[00815]
1-369 Cl [00816]
[00817]
1-370 Cl [00818]
[00819]
1-371 Cl [00820]
[00821]
1-372 Cl [00822]
[00823]
1-373 Cl [00824]
[00825]
1-374 Cl [00826]
[00827]
1-375 Cl [00828]
[00829]
1-376 Cl [00830]
[00831]
1-377 Cl [00832]
[00833]
1-378 Cl [00834]
[00835]
1-379 Cl [00836]
[00837]
1-380 Cl [00838]
[00839]
1-381 Cl [00840]
[00841]
1-382 Cl [00842]
[00843]
1-383 Cl [00844]
[00845]
1-384 Cl [00846]
[00847]
1-385 Cl [00848]
[00849]
1-386 Cl [00850]
[00851]
1-387 Cl [00852]
[00853]
1-388 Cl [00854]
[00855]
1-389 Cl [00856]
[00857]
1-390 Cl [00858]
[00859]
1-391 Cl [00860]
[00861]
1-392 Cl [00862]
[00863]
1-393 Cl [00864]
[00865]
1-394 Cl [00866]
[00867]
1-395 Cl [00868]
[00869]
1-396 Cl [00870]
[00871]
1-397 Cl [00872]
[00873]
1-398 Cl [00874]
[00875]
1-399 Cl [00876]
[00877]
1-400 Cl [00878]
[00879]
1-401 Cl [00880]
[00881]
1-402 Cl [00882]
[00883]
1-403 Cl [00884]
[00885]
1-404 Cl [00886]
[00887]
1-405 Cl [00888]
[00889]
1-406 Cl [00890]
[00891]
1-407 Cl [00892]
[00893]
1-408 Cl [00894]
[00895]
1-409 Cl [00896]
[00897]
1-410 Cl [00898]
[00899]
1-411 Cl [00900]
[00901]
1-412 Cl [00902]
[00903]
1-413 Cl [00904]
[00905]
1-414 Cl [00906]
[00907]
1-415 Cl [00908]
[00909]
1-416 Cl [00910]
[00911]
1-417 Cl [00912]
[00913]
1-418 Cl [00914]
[00915]
1-419 Cl [00916]
[00917]
1-420 Cl [00918]
[00919]
1-421 Cl [00920]
[00921]
1-422 Cl [00922]
[00923]
1-423 Cl [00924]
[00925]
1-424 Cl [00926]
[00927]
1-425 Cl [00928]
[00929]
1-426 Cl [00930]
[00931]
1-427 Cl [00932]
[00933]
1-428 Cl [00934]
[00935]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.38-8.35 (m, 2H), 8.18- 8.07 (m, 2H), 8.03-8.00 (m, 1H), 7.90 (t, J = 8.5 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.59-7.56 (m, 1H), 7.52-7.50 (m, 1H), 4.31 (s, 3H). 1-429 Cl [00936]
[00937]
1-430 Cl [00938]
[00939]
1-431 Cl [00940]
[00941]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 9.29 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.59 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.26-8.22 (m, 2H), 8.17-8.14 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 3.92 (s, 3H). 1-432 Cl [00942]
[00943]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.93-8.85 (m, 2H), 8.81-8.74 (m, 1H), 8.43- 8.36 (m, 2H), 8.02-7.99 (m, 2H), 7.74-7.60 (m, 5H), 3.92 (s, 3H). 1-433 Cl [00944]
[00945]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.51 (s, 1H), 8.20 (dd, J = 7.5, 2.0 Hz, 1H), 8.07-8.03 (m, 2H), 7.67 (d, J = 5.0 Hz, 1H), 7.65-7.58 (m, 2H), 7.44-7.41 (m, 1H), 7.35-7.32 (m, 1H), 3.96 (s, 3H). 1-434 Cl [00946]
[00947]
1-435 Cl [00948]
[00949]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 8.55 (d, J = 2.0 Hz, 1H), 8.48 (dd, J = 7.5, 2.0 Hz, 1H), 8.39 (d, J = 7.5 Hz, 1H), 8.32 (s, 1H), 8.11-8.05 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.56 (td, J = 7.5, 2.0 Hz, 1H), 7.48 (td, J = 7.5, 2.0 Hz, 1H), 3.92 (s, 3H). 1-436 Cl [00950]
[00951]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.13 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.58-8.48 (m, 2H), 8.29 (s, 1H), 7.74 (td, J = 7.5, 2.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.24-7.22 (m, 1H), 3.91 (s, 3H). 1-437 Cl [00952]
[00953]
1-438 Cl [00954]
[00955]
1-439 Cl [00956]
[00957]
1-440 Cl [00958]
[00959]
1-441 Cl [00960]
[00961]
1-442 Cl [00962]
[00963]
1-443 Cl [00964]
[00965]
1-444 Cl [00966]
[00967]
1-445 Cl [00968]
[00969]
1-446 Cl [00970]
[00971]
1-447 Cl [00972]
[00973]
1-448 Cl [00974]
[00975]
1-449 Cl [00976]
[00977]
1-450 Cl [00978]
[00979]
1-451 Cl [00980]
[00981]
1-452 Cl [00982]
[00983]
1-453 Cl [00984]
[00985]
1-454 Cl [00986]
[00987]
1-455 Cl [00988]
[00989]
1-456 Cl [00990]
[00991]
1-457 Cl [00992]
[00993]
1-458 Cl [00994]
[00995]
1-459 Cl [00996]
[00997]
1-460 Cl [00998]
[00999]
1-461 Cl [01000]
[01001]
1-462 Cl [01002]
[01003]
1-463 Cl [01004]
[01005]
1-464 Cl [01006]
[01007]
1-465 Cl [01008]
[01009]
1-466 Cl [01010]
[01011]
1-467 Cl [01012]
[01013]
1-468 Cl [01014]
[01015]
1-469 Cl [01016]
[01017]
1-470 Cl [01018]
[01019]
1-471 Cl [01020]
[01021]
1-472 Cl [01022]
[01023]
1-473 Cl [01024]
[01025]
1-474 Cl [01026]
[01027]
1-475 Cl [01028]
[01029]
1-476 Cl [01030]
[01031]
1-477 Cl [01032]
[01033]
1-478 Cl [01034]
[01035]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 9.25 (s, 2H), 8.83 (d, J = 5.0 Hz, 1H), 8.31 (s, 1H), 7.75 (d, J = 5.0 Hz, 1H), 3.91 (s, 3H), 3.85 (s, 3H). 1-479 Cl [01036]
[01037]
1-480 Cl [01038]
[01039]
1-481 Cl [01040]
[01041]
1-482 Cl [01042]
[01043]
1-483 Cl [01044]
[01045]
1-484 Cl [01046]
[01047]
1-485 Cl [01048]
[01049]
1-486 Cl [01050]
[01051]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 6.87 (s, 1H), 3.93 (s, 3H), 3.92 (s, 3H), 2.41 (s, 3H). 1-487 Cl [01052]
[01053]
1-488 Cl [01054]
[01055]
1-489 Cl [01056]
[01057]
1-490 Cl [01058]
[01059]
1-491 Cl [01060]
[01061]
1-492 Cl [01062]
[01063]
1-493 Cl [01064]
[01065]
1-494 Cl [01066]
[01067]
1-495 Cl [01068]
[01069]
1-496 Cl [01070]
[01071]
1-497 Cl [01072]
[01073]
1-498 Cl [01074]
[01075]
1-499 Cl [01076]
[01077]
1-500 Cl [01078]
[01079]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.37 (s, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.67 (s, 1H), 7.49 (d, J = 2.0 Hz, 1H), 6.69 (d, J = 2.0 Hz, 1H), 3.92 (s, 3H). 1-501 Cl [01080]
[01081]
1-502 Cl [01082]
[01083]
1-503 Cl [01084]
[01085]
1-504 Cl [01086]
[01087]
1-505 Cl [01088]
[01089]
1-506 Cl [01090]
[01091]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.37 (s, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.52 (d, J = 2.0 Hz, 1H), 7.13 (d, J = 2.0 Hz, 1H), 3.92 (s, 3H). 1-507 Cl [01092]
[01093]
1-508 Cl [01094]
[01095]
1-509 Cl [01096]
[01097]
1-510 Cl [01098]
[01099]
1-511 Cl [01100]
[01101]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 8.36 (s, 1H), 7.98-7.90 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 2.52 (s, 3H). 1-512 F [01102]
[01103]
1-513 Br [01104]
[01105]
1-514 [01106]
[01107]
[01108]
1-515 CF.sub.3 [01109]
[01110]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.36 (s, 1H), 8.02- 7.95 (m, 2H), 7.58 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.01 (s, 3H). 1-516 [01111]
[01112]
[01113]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34 (s, 1H), 8.00- 7.93 (m, 2H), 7.69-7.60 (m, 3H), 7.47-7.35 (m, 3H), 7.35-7.27 (m, 2H), 3.83 (s, 3H). 1-517 [01114]
[01115]
[01116]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 8.09- 8.01 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.03 (s, 3H), 3.67 (s, 3H). 1-518 [01117]
[01118]
[01119]
1-519 [01120]
[01121]
[01122]
1-520 [01123]
[01124]
[01125]
1-521 [01126]
[01127]
[01128]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.04- 7.97 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.02 (s, 3H), 3.00 (q, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H). 1-522 [01129]
[01130]
[01131]
1-523 [01132]
[01133]
[01134]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.31 (s, 1H), 8.04- 7.97 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.03 (s, 3H), 2.63-2.61 (m, 1H), 2.58-5.56 (m, 1H), 1.20 (t, J = 8.0 Hz, 3H). 1-524 [01135]
[01136]
[01137]
1-525 [01138]
[01139]
[01140]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.06- 7.98 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.98 (s, 3H), 2.80 (s, 6H). 1-526 [01141]
[01142]
[01143]
1-527 Et [01144]
[01145]
1-528 [01146]
[01147]
[01148]
1-529 NO.sub.2 [01149]
[01150]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 8.35 (s, 1H), 7.98- 7.91 (m, 2H), 7.72 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.26 (s, 3H). 1-530 CN [01151]
[01152]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 9.01 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.05- 7.97 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.92 (s, 3H). 1-531 [01153]
[01154]
[01155]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.37 (s, 1H), 8.03- 7.95 (m, 2H), 7.65 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.68 (s, 2H), 4.33 (s, 3H), 3.28 (s, 3H). 1-532 [01156]
[01157]
[01158]
1-533 [01159]
[01160]
[01161]
1-534 [01162]
[01163]
[01164]
1-535 [01165]
[01166]
[01167]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.61 (d, J = 5.0 Hz, 1H), 8.03-7.96 (m, 2H), 7.35-7.25 (m, 3H), 6.53 (dd, J = 16.5, 10.0 Hz, 1H), 5.60-5.67 (m, 1H), 5.31 5.29 (m, 1H), 4.33 (s, 3H). 1-536 [01168]
[01169]
[01170]
1-537 [01171]
[01172]
[01173]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.15 (s, 1H), 9.01 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.05- 7.97 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.03 (s, 3H), 3.92 (s, 1H). 1-538 [01174]
[01175]
[01176]
1-539 [01177]
[01178]
[01179]
1-540 [01180]
[01181]
[01182]
1-541 Cl [01183]
[01184]
1-542 Cl [01185]
[01186]
1-543 Cl [01187]
[01188]
1-544 Cl [01189]
[01190]
1-545 Cl [01191]
[01192]
1-546 Cl [01193]
[01194]
1-547 Cl [01195]
[01196]
1-548 Cl [01197]
[01198]
1-549 Cl [01199]
[01200]
1-550 Cl [01201]
[01202]
1-551 Cl [01203]
[01204]
1-552 Cl [01205]
[01206]
1-553 Cl [01207]
[01208]
1-554 Cl [01209]
[01210]
1-555 Cl [01211]
[01212]
1-556 Cl [01213]
[01214]
1-557 Cl [01215]
[01216]
1-558 Cl [01217]
[01218]
1-559 Cl [01219]
[01220]
1-560 Cl [01221]
[01222]
1-561 Cl [01223]
[01224]
1-562 Cl [01225]
[01226]
1-563 Cl [01227]
[01228]
1-564 Cl [01229]
[01230]
1-565 Cl [01231]
[01232]
1-566 Cl [01233]
[01234]
1-567 Cl [01235]
[01236]
1-568 Cl [01237]
[01238]
1-569 Cl [01239]
[01240]
1-570 Cl [01241]
[01242]
1-571 Cl [01243]
[01244]
1-572 Cl [01245]
[01246]
1-573 Cl [01247]
[01248]
1-574 Cl [01249]
[01250]
1-575 Cl [01251]
[01252]
1-576 Cl [01253]
[01254]
1-577 Cl [01255]
[01256]
1-578 Cl [01257]
[01258]
1-579 Cl [01259]
[01260]
1-580 Cl [01261]
[01262]
1-581 Cl [01263]
[01264]
1-582 Cl [01265]
[01266]
1-583 Cl [01267]
[01268]
1-584 Cl [01269]
[01270]
1-585 Cl [01271]
[01272]
1-586 Cl [01273]
[01274]
1-587 Cl [01275]
[01276]
1-588 Cl [01277]
[01278]
1-589 Cl [01279]
[01280]
1-590 Cl [01281]
[01282]
1-591 Cl [01283]
[01284]
1-592 Cl [01285]
[01286]
1-593 Cl [01287]
[01288]
1-594 Cl [01289]
[01290]
1-595 Cl [01291]
[01292]
1-596 Cl [01293]
[01294]
1-597 Cl [01295]
[01296]
1-598 Cl [01297]
[01298]
1-599 Cl [01299]
[01300]
1-600 Cl [01301]
[01302]
1-601 Cl [01303]
[01304]
1-602 Cl [01305]
[01306]
1-603 Cl [01307]
[01308]
1-604 Cl [01309]
[01310]
1-605 Cl [01311]
[01312]
1-606 Cl [01313]
[01314]
1-607 Cl [01315]
[01316]
1-608 Cl [01317]
[01318]
1-609 Cl [01319]
[01320]
1-610 Cl [01321]
[01322]
1-611 Cl [01323]
[01324]
1-612 Cl [01325]
[01326]
1-613 Cl [01327]
[01328]
1-614 Cl [01329]
[01330]
1-615 Cl [01331]
[01332]
1-616 Cl [01333]
[01334]
1-617 Cl [01335]
[01336]
1-618 Cl [01337]
[01338]
1-619 Cl [01339]
[01340]
1-620 Cl [01341]
[01342]
1-621 Cl [01343]
[01344]
1-622 Cl [01345]
[01346]
1-623 Cl [01347]
[01348]
1-624 Cl [01349]
[01350]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.16 (s, 1H), 10.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04- 7.96 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 2.45 (s, 3H). 1-625 Cl [01351]
[01352]
1-626 Cl [01353]
[01354]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.61 (s, 3H), 2.18 (p, J = 7.0 Hz, 1H), 1.13 (m, 2H), 0.88 (m, 2H). 1-627 Cl [01355]
[01356]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.46 (hept, J = 8.0 Hz, 1H), 1.65 (d, J = 8.0 Hz, 6H). 1-628 Cl [01357]
[01358]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.03-7.96 (m, 2H), 7.67 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.32 (s, 2H), 3.94 (s, 3H), 2.99 (s, 3H). 1-629 Cl [01359]
[01360]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.08-8.00 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.93 (s, 3H), 3.59 (s, 3H), 3.51 (s, 2H). 1-630 Cl [01361]
[01362]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.11-8.02 (m, 4H), 7.65 (d, J = 5.0 Hz, 1H), 7.54-7.46 (m, 1H), 7.48-7.40 (m, 2H), 7.35-7.27 (m, 2H), 3.97 (s, 3H). 1-631 Cl [01363]
[01364]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.89 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.40 (q, J = 8.0 Hz, 2H), 1.49 (t, J = 8.0 Hz, 3H). 1-632 Cl [01365]
[01366]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.13 (s, 1H), 10.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.70 (dd, J = 5.0, 2.0 Hz, 1H), 8.46-8.44 (m, 2H), 8.11- 8.03 (m, 2H), 7.64 (d, J = 5.0 Hz, 1H), 7.57 (dd, J = 8.0, 2.0 Hz, 1H), 7.35-7.27 (m, 2H), . 1-633 Cl [01367]
[01368]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.08-8.00 (m, 2H), 7.63 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.94 (s, 3H), 3.63 (t, J = 8.0 Hz, 4H), 3.36 (t, J = 8.0 Hz, 4H). 1-634 Cl CH.sub.3 [01369]
1-635 Cl [01370]
[01371]
1-636 Cl [01372]
[01373]
1-637 Cl [01374]
[01375]
1-638 Cl [01376]
[01377]
1-639 Cl [01378]
[01379]
1-640 Cl [01380]
[01381]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.12 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 6.26-6.19 (m, 1H), 4.23-4.17 (m, 2H), 3.86 (s, 3H), 3.79 (t, J = 5.0 Hz, 2H), 2.50 (s, 3H), 2.40 (t, J = 5.0, 2H). 1-641 Cl [01382]
[01383]
1-642 Cl [01384]
[01385]
1-643 Cl [01386]
[01387]
1-644 Cl [01388]
[01389]
1-645 Cl [01390]
[01391]
1-646 Cl [01392]
[01393]
1-647 Cl [01394]
[01395]
1-648 Cl [01396]
[01397]
1-649 Cl [01398]
[01399]
1-650 Cl [01400]
[01401]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.12 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.88 (s, 3H), 2.50 (s, 3H). 1-651 Cl [01402]
[01403]
1-652 Cl [01404]
[01405]
1-653 Cl [01406]
[01407]
1-654 Cl [01408]
[01409]
1-655 Cl [01410]
[01411]
1-656 Cl [01412]
[01413]
1-657 Cl [01414]
[01415]
1-658 Cl [01416]
[01417]
1-659 Cl [01418]
[01419]
1-660 Cl [01420]
[01421]
1-661 Cl [01422]
[01423]
1-662 Cl [01424]
[01425]
1-663 Cl [01426]
[01427]
1-664 Cl [01428]
[01429]
1-665 Cl [01430]
[01431]
1-666 Cl [01432]
[01433]
1-667 Cl [01434]
[01435]
1-668 Cl [01436]
[01437]
1-669 Cl [01438]
[01439]
1-670 Cl [01440]
[01441]
1-671 Cl [01442]
[01443]
1-672 Cl [01444]
[01445]
1-673 Cl [01446]
[01447]
1-674 Cl [01448]
[01449]
1-675 Cl [01450]
[01451]
1-676 Cl [01452]
[01453]
1-677 Cl [01454]
[01455]
1-678 Cl [01456]
[01457]
1-679 Cl [01458]
[01459]
1-680 Cl [01460]
[01461]
1-681 Cl [01462]
[01463]
1-682 Cl [01464]
[01465]
1-683 Cl [01466]
[01467]
1-684 Cl [01468]
[01469]
1-685 Cl [01470]
[01471]
1-686 Cl [01472]
[01473]
1-687 Cl [01474]
[01475]
1-688 Cl [01476]
[01477]
1-689 Cl [01478]
[01479]
1-690 Cl [01480]
[01481]
1-691 Cl [01482]
[01483]
1-692 Cl [01484]
[01485]
1-693 Cl [01486]
[01487]
1-694 Cl [01488]
[01489]
1-695 Cl [01490]
[01491]
1-696 Cl [01492]
[01493]
1-697 Cl [01494]
[01495]
1-698 Cl [01496]
[01497]
1-699 Cl [01498]
[01499]
1-700 Cl [01500]
[01501]
1-701 Cl [01502]
[01503]
1-702 Cl [01504]
[01505]
1-703 Cl [01506]
[01507]
1-704 Cl [01508]
[01509]
1-705 Cl [01510]
[01511]
1-706 Cl [01512]
[01513]
1-707 Cl [01514]
[01515]
1-708 Cl [01516]
[01517]
1-709 Cl [01518]
[01519]
1-710 Cl [01520]
[01521]
1-711 Cl [01522]
[01523]
1-712 Cl [01524]
[01525]
1-713 Cl [01526]
[01527]
1-714 Cl [01528]
[01529]
1-715 Cl [01530]
[01531]
1-716 Cl [01532]
[01533]
1-717 Cl [01534]
[01535]
1-718 Cl [01536]
[01537]
1-719 Cl [01538]
[01539]
1-720 Cl [01540]
[01541]
1-721 Cl [01542]
[01543]
1-722 Cl [01544]
[01545]
1-723 Cl [01546]
[01547]
1-724 Cl [01548]
[01549]
1-725 Cl [01550]
[01551]
1-726 Cl [01552]
[01553]
1-727 Cl [01554]
[01555]
1-728 Cl [01556]
[01557]
1-729 Cl [01558]
[01559]
1-730 Cl [01560]
[01561]
1-731 Cl [01562]
[01563]
1-732 Cl [01564]
[01565]
1-733 Cl [01566]
[01567]
1-734 Cl [01568]
[01569]
1-735 Cl [01570]
[01571]
1-736 Cl [01572]
[01573]
1-737 Cl [01574]
[01575]
1-738 Cl [01576]
[01577]
1-739 Cl [01578]
[01579]
1-740 Cl [01580]
[01581]
1-741 Cl [01582]
[01583]
1-742 Cl [01584]
[01585]
1-743 Cl [01586]
[01587]
1-744 Cl [01588]
[01589]
1-745 Cl [01590]
[01591]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 8.35 (dd, J = 7.5, 2.0 Hz, 1H), 8.13-8.10 (m, 2H), 8.04 (dt, J = 7.5, 2.0 Hz, 1H), 7.94-7.85 (m, 2H), 7.59 (td, J = 7.5, 2.0 Hz, 1H), 7.52 (td, J = 7.5, 2.00 Hz, 1H), 3.88 (s, 3H), 2.51 (s, 3H). 1-746 Cl [01592]
[01593]
1-747 Cl [01594]
[01595]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 9.28 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.60 (d, J = 5.5 Hz, 1H), 8.20-8.17 (m, 2H), 7.89-7.78 (m, 3H), 3.87 (s, 3H), 2.51 (s, 3H). 1-748 Cl [01596]
[01597]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.93-8.86 (m, 2H), 8.78 (dd, J = 8.0, 2.5 Hz, 1H), 8.38 (s, 1H), 8.05-7.94 (m, 2H), 7.83 (d, J = 5.0 Hz, 1H), 7.74-7.60 (m, 4H), 3.88 (s, 3H), 2.51 (s, 3H). 1-749 Cl [01598]
[01599]
1-750 Cl [01600]
[01601]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.21 (dd, J = 7.5, 2.0 Hz, 1H), 8.05-8.03 (m, 2H), 7.85 (d, J = 5.0 Hz, 1H), 7.66-7.58 (m, 2H), 7.44 (td, J = 7.5, 2.0 Hz, 1H), 7.35 (td, J = 7.5, 2.0 Hz, 1H), 3.88 (s, 3H), 2.52 (s, 3H). 1-751 Cl [01602]
[01603]
1-752 Cl [01604]
[01605]
1-753 Cl [01606]
[01607]
1-754 Cl [01608]
[01609]
1-755 Cl [01610]
[01611]
1-756 Cl [01612]
[01613]
1-757 Cl [01614]
[01615]
1-758 Cl [01616]
[01617]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.91 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 5.0 Hz, 1H), 3.87 (s, 3H), 2.50 (s, 3H), 2.48 (s, 3H). 1-759 Cl [01618]
[01619]
1-760 Cl [01620]
[01621]
1-761 Cl [01622]
[01623]
1-762 Cl [01624]
[01625]
1-763 Cl [01626]
[01627]
1-764 Cl [01628]
[01629]
1-765 Cl [01630]
[01631]
1-766 Cl [01632]
[01633]
1-767 Cl [01634]
[01635]
1-768 Cl [01636]
[01637]
1-769 Cl [01638]
[01639]
1-770 Cl [01640]
[01641]
1-771 Cl [01642]
[01643]
1-772 Cl [01644]
[01645]
1-773 Cl [01646]
[01647]
1-774 Cl [01648]
[01649]
1-775 Cl [01650]
[01651]
1-776 Cl [01652]
[01653]
1-777 Cl [01654]
[01655]
1-778 Cl [01656]
[01657]
1-779 Cl [01658]
[01659]
1-780 Cl [01660]
[01661]
1-781 Cl [01662]
[01663]
1-782 Cl [01664]
[01665]
1-783 Cl [01666]
[01667]
1-784 Cl [01668]
[01669]
1-785 Cl [01670]
[01671]
1-786 Cl [01672]
[01673]
1-787 Cl [01674]
[01675]
1-788 Cl [01676]
[01677]
1-789 Cl [01678]
[01679]
1-790 Cl [01680]
[01681]
1-791 Cl [01682]
[01683]
1-792 Cl [01684]
[01685]
1-793 Cl [01686]
[01687]
1-794 Cl [01688]
[01689]
1-795 Cl [01690]
[01691]
1-796 Cl [01692]
[01693]
1-797 Cl [01694]
[01695]
1-798 Cl [01696]
[01697]
1-799 Cl [01698]
[01699]
1-800 Cl [01700]
[01701]
1-801 Cl [01702]
[01703]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.80 (s, 1H), 6.97 (s, 1H), 3.92 (s, 3H), 3.87 (s, 3H), 2.51 (s, 3H). 1-802 Cl [01704]
[01705]
1-803 Cl [01706]
[01707]
1-804 Cl [01708]
[01709]
1-805 Cl [01710]
[01711]
1-806 Cl [01712]
[01713]
1-807 Cl [01714]
[01715]
1-808 Cl [01716]
[01717]
1-809 Cl [01718]
[01719]
1-810 Cl [01720]
[01721]
1-811 Cl [01722]
[01723]
1-812 Cl [01724]
[01725]
1-813 Cl [01726]
[01727]
1-814 Cl [01728]
[01729]
1-815 Cl [01730]
[01731]
1-816 Cl [01732]
[01733]
1-817 Cl [01734]
[01735]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.26 (d, J = 2.0 Hz, 1H), 6.98 (t, J = 2.0 Hz, 1H), 3.86 (s, 3H), 2.51 (s, 3H). 1-818 Cl [01736]
[01737]
1-819 Cl [01738]
[01739]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.98 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 2.0 Hz, 1H), 7.47 (d, J = 2.0 Hz, 1H), 7.15 (t, J = 2.0 Hz, 1H), 3.86 (s, 3H), 2.51 (s, 3H). 1-820 Cl [01740]
[01741]
1-821 Cl [01742]
[01743]
1-822 Cl [01744]
[01745]
1-823 Cl [01746]
[01747]
1-824 Cl [01748]
[01749]
1-825 Cl [01750]
[01751]
1-826 Cl [01752]
[01753]
1-827 CH.sub.3 [01754]
[01755]
1-828 F [01756]
[01757]
1-829 Br [01758]
[01759]
1-830 [01760]
[01761]
[01762]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 7.95-7.87 (m, 2H), 7.37 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.87 (s, 3H), 2.85 (hept, J = 7.0 Hz, 1H), 2.50 (s, 3H), 1.11 (d, J = 7.0 Hz, 6H). 1-831 CF.sub.3 [01763]
[01764]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.58 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.89 (s, 3H), 2.51 (s, 3H). 1-832 [01765]
[01766]
[01767]
1-833 [01768]
[01769]
[01770]
1-834 [01771]
[01772]
[01773]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.33 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 8.10-8.02 (m, 2H), 7.94 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.10 (q, J = 8.0 Hz, 2H), 3.88 (s, 3H), 2.51 (s, 3H), 1.34 (t, J = 8.0 Hz, 3H). 1-835 [01774]
[01775]
[01776]
1-836 [01777]
[01778]
[01779]
1-837 [01780]
[01781]
[01782]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.88 (s, 3H), 3.00 (q, J = 8.0 Hz, 2H), 2.50 (s, 3H), 1.19 (t, J = 8.0 Hz, 3H). 1-838 [01783]
[01784]
[01785]
1-839 [01786]
[01787]
[01788]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.87 (s, 3H), 2.61-2.59 (m, 1H), 2.57-2.55 (m, 1H) 2.50 (s, 3H), 1.20 (t, J = 8.0 Hz, 3H). 1-840 [01789]
[01790]
[01791]
1-841 [01792]
[01793]
[01794]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.07-8.00 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.87 (s, 3H), 2.76 (s, 6H), 2.49 (s, 3H). 1-842 [01795]
[01796]
[01797]
1-843 Et [01798]
[01799]
1-844 [01800]
[01801]
[01802]
1-845 NO.sub.2 [01803]
[01804]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 7.99-7.91 (m, 2H), 7.71 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.89 (s, 3H), 2.52 (s, 3H). 1-846 CN [01805]
[01806]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 9.02 (d, J = 5.0 Hz, 1H), 8.06-7.98 (m, 2H), 7.73 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.89 (s, 3H), 2.51 (s, 3H). 1-847 [01807]
[01808]
[01809]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 3.88 (s, 3H), 3.28 (s, 3H), 2.51 (s, 3H). 1-848 [01810]
[01811]
[01812]
1-849 [01813]
[01814]
[01815]
1-850 [01816]
[01817]
[01818]
1-851 [01819]
[01820]
[01821]
1-852 [01822]
[01823]
[01824]
1-853 [01825]
[01826]
[01827]
1-854 [01828]
[01829]
[01830]
1-855 [01831]
[01832]
[01833]
1-856 [01834]
[01835]
[01836]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.60-7.52 (m, 2H), 7.35-7.27 (m, 2H), 7.23-7.15 (m, 2H), 3.79 (s, 3H), 2.49 (s, 3H). 1-857 Cl [01837]
[01838]
1-858 Cl [01839]
[01840]
1-859 Cl [01841]
[01842]
1-860 Cl [01843]
[01844]
1-861 Cl [01845]
[01846]
1-862 Cl [01847]
[01848]
1-863 Cl [01849]
[01850]
1-864 Cl [01851]
[01852]
1-865 Cl [01853]
[01854]
1-866 Cl [01855]
[01856]
1-867 Cl [01857]
[01858]
1-868 Cl [01859]
[01860]
1-869 Cl [01861]
[01862]
1-870 Cl [01863]
[01864]
1-871 Cl [01865]
[01866]
1-872 Cl [01867]
[01868]
1-873 Cl [01869]
[01870]
1-874 Cl [01871]
[01872]
1-875 Cl [01873]
[01874]
1-876 Cl [01875]
[01876]
1-877 Cl [01877]
[01878]
1-878 Cl [01879]
[01880]
1-879 Cl [01881]
[01882]
1-880 Cl [01883]
[01884]
1-881 Cl [01885]
[01886]
1-882 Cl [01887]
[01888]
1-883 Cl [01889]
[01890]
1-884 Cl [01891]
[01892]
1-885 Cl [01893]
[01894]
1-886 Cl [01895]
[01896]
1-887 Cl [01897]
[01898]
1-888 Cl [01899]
[01900]
1-889 Cl [01901]
[01902]
1-890 Cl [01903]
[01904]
1-891 Cl [01905]
[01906]
1-892 Cl [01907]
[01908]
1-893 Cl [01909]
[01910]
1-894 Cl [01911]
[01912]
1-895 Cl [01913]
[01914]
1-896 Cl [01915]
[01916]
1-897 Cl [01917]
[01918]
1-898 Cl [01919]
[01920]
1-899 Cl [01921]
[01922]
1-900 Cl [01923]
[01924]
1-901 Cl [01925]
[01926]
1-902 Cl [01927]
[01928]
1-903 Cl [01929]
[01930]
1-904 Cl [01931]
[01932]
1-905 Cl [01933]
[01934]
1-906 Cl [01935]
[01936]
1-907 Cl [01937]
[01938]
1-908 Cl [01939]
[01940]
1-909 Cl [01941]
[01942]
1-910 Cl [01943]
[01944]
1-911 Cl [01945]
[01946]
1-912 Cl [01947]
[01948]
1-913 Cl [01949]
[01950]
1-914 Cl [01951]
[01952]
1-915 Cl [01953]
[01954]
1-916 Cl [01955]
[01956]
1-917 Cl [01957]
[01958]
1-918 Cl [01959]
[01960]
1-919 Cl [01961]
[01962]
1-920 Cl [01963]
[01964]
1-921 Cl [01965]
[01966]
1-922 Cl [01967]
[01968]
1-923 Cl [01969]
[01970]
1-924 Cl [01971]
[01972]
1-925 Cl [01973]
[01974]
1-926 Cl [01975]
[01976]
1-927 Cl [01977]
[01978]
1-928 Cl [01979]
[01980]
1-929 Cl [01981]
[01982]
1-930 Cl [01983]
[01984]
1-931 Cl [01985]
[01986]
1-932 Cl [01987]
[01988]
1-933 Cl [01989]
[01990]
1-934 Cl [01991]
[01992]
1-935 Cl [01993]
[01994]
1-936 Cl [01995]
[01996]
1-937 Cl [01997]
[01998]
1-938 Cl [01999]
[02000]
1-939 Cl [02001]
[02002]
1-940 Cl [02003]
[02004]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 9.15 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03- 7.95 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.82 (s, 3H). 1-941 Cl [02005]
[02006]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.02-7.95 (m, 2H), 7.74 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.07 (q, J = 8.0 Hz, 2H), 1.29 (t, J = 8.0 Hz, 3H). 1-942 Cl [02007]
[02008]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.73 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.01 (s, 3H), 3.88 (s, 3H). 1-943 Cl [02009]
[02010]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.68 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.18 (t, J = 8.0 Hz, 2H), 3.96 (t, J = 8.0 Hz, 2H), 3.58 (s, 3H), 2.47 (s, 3H). 1-944 Cl [02011]
[02012]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.10 (s, 1H), 10.40 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.05- 7.97 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.36 (t, J = 5.5 Hz, 4H), 1.62- 1.56 (m, 2H), 1.51 (p, J = 7.0 Hz, 4H). 1-945 Cl [02013]
[02014]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.05-7.93 (m, 4H), 7.83 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.14-7.08 (m, 2H), 3.86 (s, 3H), 3.79 (s, 3H). 1-946 Cl CH.sub.3 [02015]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.94 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 2.59 (s, 3H), 2.46 (s, 3H). 1-947 Cl [02016]
[02017]
1-948 Cl [02018]
[02019]
1-949 Cl [02020]
[02021]
1-950 Cl [02022]
[02023]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.66 (d, J = 5.0 Hz, 1H), 6.18 (t, J = 6.0 Hz, 1H), 2.44 (s, 3H), 2.13-1.92 (m, 4H), 1.76-1.58 (m, 2H), 1.48-1.35 (m, 2H). 1-951 Cl [02024]
[02025]
1-952 Cl [02026]
[02027]
1-953 Cl [02028]
[02029]
1-954 Cl [02030]
[02031]
1-955 Cl [02032]
[02033]
1-956 Cl [02034]
[02035]
1-957 Cl [02036]
[02037]
1-958 Cl [02038]
[02039]
1-959 Cl [02040]
[02041]
1-960 Cl [02042]
[02043]
1-961 Cl [02044]
[02045]
1-962 Cl [02046]
[02047]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.63-7.55 (m, 2H), 7.12-7.03 (m, 3H), 2.38 (s, 3H). 1-963 Cl [02048]
[02049]
1-964 Cl [02050]
[02051]
1-965 Cl [02052]
[02053]
1-966 Cl [02054]
[02055]
1-967 Cl [02056]
[02057]
1-968 Cl [02058]
[02059]
1-969 Cl [02060]
[02061]
1-970 Cl [02062]
[02063]
1-971 Cl [02064]
[02065]
1-972 Cl [02066]
[02067]
1-973 Cl [02068]
[02069]
1-974 Cl [02070]
[02071]
1-975 Cl [02072]
[02073]
1-976 Cl [02074]
[02075]
1-977 Cl [02076]
[02077]
1-978 Cl [02078]
[02079]
1-979 Cl [02080]
[02081]
1-980 Cl [02082]
[02083]
1-981 Cl [02084]
[02085]
1-982 Cl [02086]
[02087]
1-983 Cl [02088]
[02089]
1-984 Cl [02090]
[02091]
1-985 Cl [02092]
[02093]
1-986 Cl [02094]
[02095]
1-987 Cl [02096]
[02097]
1-988 Cl [02098]
[02099]
1-989 Cl [02100]
[02101]
1-990 Cl [02102]
[02103]
1-991 Cl [02104]
[02105]
1-992 Cl [02106]
[02107]
1-993 Cl [02108]
[02109]
1-994 Cl [02110]
[02111]
1-995 Cl [02112]
[02113]
1-996 Cl [02114]
[02115]
1-997 Cl [02116]
[02117]
1-998 Cl [02118]
[02119]
1-999 Cl [02120]
[02121]
1-1000 Cl [02122]
[02123]
1-1001 Cl [02124]
[02125]
1-1002 Cl [02126]
[02127]
1-1003 Cl [02128]
[02129]
1-1004 Cl [02130]
[02131]
1-1005 Cl [02132]
[02133]
1-1006 Cl [02134]
[02135]
1-1007 Cl [02136]
[02137]
1-1008 Cl [02138]
[02139]
1-1009 Cl [02140]
[02141]
1-1010 Cl [02142]
[02143]
1-1011 Cl [02144]
[02145]
1-1012 Cl [02146]
[02147]
1-1013 Cl [02148]
[02149]
1-1014 Cl [02150]
[02151]
1-1015 Cl [02152]
[02153]
1-1016 Cl [02154]
[02155]
1-1017 Cl [02156]
[02157]
1-1018 Cl [02158]
[02159]
1-1019 Cl [02160]
[02161]
1-1020 Cl [02162]
[02163]
1-1021 Cl [02164]
[02165]
1-1022 Cl [02166]
[02167]
1-1023 Cl [02168]
[02169]
1-1024 Cl [02170]
[02171]
1-1025 Cl [02172]
[02173]
1-1026 Cl [02174]
[02175]
1-1027 Cl [02176]
[02177]
1-1028 Cl [02178]
[02179]
1-1029 Cl [02180]
[02181]
1-1030 Cl [02182]
[02183]
1-1031 Cl [02184]
[02185]
1-1032 Cl [02186]
[02187]
1-1033 Cl [02188]
[02189]
1-1034 Cl [02190]
[02191]
1-1035 Cl [02192]
[02193]
1-1036 Cl [02194]
[02195]
1-1037 Cl [02196]
[02197]
1-1038 Cl [02198]
[02199]
1-1039 Cl [02200]
[02201]
1-1040 Cl [02202]
[02203]
1-1041 Cl [02204]
[02205]
1-1042 Cl [02206]
[02207]
1-1043 Cl [02208]
[02209]
1-1044 Cl [02210]
[02211]
1-1045 Cl [02212]
[02213]
1-1046 Cl [02214]
[02215]
1-1047 Cl [02216]
[02217]
1-1048 Cl [02218]
[02219]
1-1049 Cl [02220]
[02221]
1-1050 Cl [02222]
[02223]
1-1051 Cl [02224]
[02225]
1-1052 Cl [02226]
[02227]
1-1053 Cl [02228]
[02229]
1-1054 Cl [02230]
[02231]
1-1055 Cl [02232]
[02233]
1-1056 Cl [02234]
[02235]
1-1057 Cl [02236]
[02237]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.52 (d, J = 1.5 Hz, 1H), 8.17 (dd, J = 7.5, 1.5 Hz, 1H), 8.09-7.99 (m, 3H), 7.67-7.58 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 2.44 (s, 3H). 1-1058 Cl [02238]
[02239]
1-1059 Cl [02240]
[02241]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 9.26 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.59 (d, J = 5.5 Hz, 1H), 8.22-8.13 (m, 2H), 7.86-7.79 (m, 2H), 7.60 (d, J = 5.0 Hz, 1H), 2.46 (s, 3H). 1-1060 Cl [02242]
[02243]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.90 (dd, J = 7.5, 1.5 Hz, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.81-8.73 (m, 1H), 8.38 (d, J = 1.5 Hz, 1H), 8.09-7.97 (m, 2H), 7.74-7.59 (m, 5H), 2.48 (s, 3H). 1-1061 Cl [02244]
[02245]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.20 (dd, J = 7.5, 1.5 Hz, 1H), 8.15-8.01 (m, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.64-7.57 (m, 2H), 7.48-7.41 (m, 1H), 7.39-7.26 (m, 1H), 2.45 (s, 3H). 1-1062 Cl [02246]
[02247]
1-1063 Cl [02248]
[02249]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.52 (d, J = 1.5 Hz, 1H), 8.47 (dd, J = 7.5, 1.5 Hz, 1H), 8.38 (d, J = 7.5 Hz, 1H), 8.16-8.02 (m, 2H), 7.60-7.52 (m, 2H), 7.53-7.42 m, 1H), 2.44 (s, 3H). 1-1064 Cl [02250]
[02251]
1-1065 Cl [02252]
[02253]
1-1066 Cl [02254]
[02255]
1-1067 Cl [02256]
[02257]
1-1068 Cl [02258]
[02259]
1-1069 Cl [02260]
[02261]
1-1070 Cl [02262]
[02263]
1-1071 Cl [02264]
[02265]
1-1072 Cl [02266]
[02267]
1-1073 Cl [02268]
[02269]
1-1074 Cl [02270]
[02271]
1-1075 Cl [02272]
[02273]
1-1076 Cl [02274]
[02275]
1-1077 Cl [02276]
[02277]
1-1078 Cl [02278]
[02279]
1-1079 Cl [02280]
[02281]
1-1080 Cl [02282]
[02283]
1-1081 Cl [02284]
[02285]
1-1082 Cl [02286]
[02287]
1-1083 Cl [02288]
[02289]
1-1084 Cl [02290]
[02291]
1-1085 Cl [02292]
[02293]
1-1086 Cl [02294]
[02295]
1-1087 Cl [02296]
[02297]
1-1088 Cl [02298]
[02299]
1-1089 Cl [02300]
[02301]
1-1090 Cl [02302]
[02303]
1-1091 Cl [02304]
[02305]
1-1092 Cl [02306]
[02307]
1-1093 Cl [02308]
[02309]
1-1094 Cl [02310]
[02311]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.31 (dd, J = 5.5, 5.0 Hz, 1H), 8.16-8.01 (m, 1H), 7.88-7.85 (m, 1H), 7.73 (d, J = 5.0 Hz, 1H), 2.44 (s, 3H). 1-1095 Cl [02312]
[02313]
1-1096 Cl [02314]
[02315]
1-1097 Cl [02316]
[02317]
1-1098 Cl [02318]
[02319]
1-1099 Cl [02320]
[02321]
1-1100 Cl [02322]
[02323]
1-1101 Cl [02324]
[02325]
1-1102 Cl [02326]
[02327]
1-1103 Cl [02328]
[02329]
1-1104 Cl [02330]
[02331]
1-1105 Cl [02332]
[02333]
1-1106 Cl [02334]
[02335]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 9.48 (s, 2H), 8.80 (d, J = 5.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 3.85 (s, 3H), 2.44 (s, 3H). 1-1107 Cl [02336]
[02337]
1-1108 Cl [02338]
[02339]
1-1109 Cl [02340]
[02341]
1-1110 Cl [02342]
[02343]
1-1111 Cl [02344]
[02345]
1-1112 Cl [02346]
[02347]
1-1113 Cl [02348]
[02349]
1-1114 Cl [02350]
[02351]
1-1115 Cl [02352]
[02353]
1-1116 Cl [02354]
[02355]
1-1117 Cl [02356]
[02357]
1-1118 Cl [02358]
[02359]
1-1119 Cl [02360]
[02361]
1-1120 Cl [02362]
[02363]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.84 (t, J = 65.0 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 6.98 (s, 1H), 2.45 (s, 3H), 2.39 (s, 3H). 1-1121 Cl [02364]
[02365]
1-1122 Cl [02366]
[02367]
1-1123 Cl [02368]
[02369]
1-1124 Cl [02370]
[02371]
1-1125 Cl [02372]
[02373]
1-1126 Cl [02374]
[02375]
1-1127 Cl [02376]
[02377]
1-1128 Cl [02378]
[02379]
1-1129 Cl [02380]
[02381]
1-1130 Cl [02382]
[02383]
1-1131 Cl [02384]
[02385]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.17 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 7.49-7.32 (m, 1H), 6.38-6.27 (m, 1H), 2.63 (s, 3H). 1-1132 Cl [02386]
[02387]
1-1133 Cl [02388]
[02389]
1-1134 Cl [02390]
[02391]
1-1135 Cl [02392]
[02393]
1-1136 Cl [02394]
[02395]
1-1137 Cl [02396]
[02397]
1-1138 Cl [02398]
[02399]
1-1139 Cl [02400]
[02401]
1-1140 Cl [02402]
[02403]
1-1141 CH.sub.3 [02404]
[02405]
1-1142 F [02406]
[02407]
1-1143 Br [02408]
[02409]
1-1144 [02410]
[02411]
[02412]
1-1145 CF.sub.3 [02413]
[02414]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.00-7.93 (m, 2H), 7.48 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.45 (s, 3H). 1-1146 [02415]
[02416]
[02417]
1-1147 [02418]
[02419]
[02420]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.53 (d, J = 5.0 Hz, 1H), 8.06-7.98 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.64 (s, 3H), 2.45 (s, 3H). 1-1148 [02421]
[02422]
[02423]
1-1149 [02424]
[02425]
[02426]
1-1150 [02427]
[02428]
[02429]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.60 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.41 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.45 (s, 3H), 2.20 (s, 3H). 1-1151 [02430]
[02431]
[02432]
1-1152 [02433]
[02434]
[02435]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.97-7.89 (m, 2H), 7.40 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.45 (s, 3H), 2.37 (s, 3H). 1-1153 [02436]
[02437]
[02438]
1-1154 [02439]
[02440]
[02441]
1-1155 [02442]
[02443]
[02444]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.35 (d, J = 5.0 Hz, 1H), 7.95-7.88 (m, 1H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.72 (s, 6H), 2.44 (s, 3H). 1-1156 [02445]
[02446]
[02447]
1-1157 Et [02448]
[02449]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.07-7.81 (m, 2H), 7.52-7.20 (m, 3H), 2.70 (q, J = 8.0 Hz, 2H), 2.45 (s, 3H), 1.07 (t, J = 8.0 Hz, 3H). 1-1158 [02450]
[02451]
[02452]
1-1159 NO.sub.2 [02453]
[02454]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.95-7.87 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.47 (s, 3H). 1-1160 CN [02455]
[02456]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 8.02-7.95 (m, 2H), 7.64 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.46 (s, 3H). 1-1161 [02457]
[02458]
[02459]
1-1162 [02460]
[02461]
[02462]
1-1163 [02463]
[02464]
[02465]
1-1164 [02466]
[02467]
[02468]
1-1165 [02469]
[02470]
[02471]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.01-7.94 (m, 2H), 7.40 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 3.58 (q, J = 8.0 Hz, 2H), 2.45 (s, 3H), 1.18 (t, J = 8.0 Hz, 3H). 1-1166 [02472]
[02473]
[02474]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.35-7.27 (m, 2H), 7.19 (d, J = 5.0 Hz, 1H), 6.62-6.48 (m, 1H), 5.48-5.36 (m, 1H), 5.30-5.22 (m, 1H), 2.43 (s, 3H). 1-1167 [02475]
[02476]
[02477]
1-1168 [02478]
[02479]
[02480]
1-1169 [02481]
[02482]
[02483]
1-1170 [02484]
[02485]
[02486]
1-1171 [02487]
[02488]
[02489]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.98-7.91 (m, 2H), 7.57-7.47 (m, 3H), 7.35-7.27 (m, 2H), 7.23- 7.15 (m, 2H), 2.43 (s, 3H). 1-1172 Cl [02490]
[02491]
1-1173 Cl [02492]
[02493]
1-1174 Cl [02494]
[02495]
1-1175 Cl [02496]
[02497]
1-1176 Cl [02498]
[02499]
1-1177 Cl [02500]
[02501]
1-1178 Cl [02502]
[02503]
1-1179 Cl [02504]
[02505]
1-1180 Cl [02506]
[02507]
1-1181 Cl [02508]
[02509]
1-1182 Cl [02510]
[02511]
1-1183 Cl [02512]
[02513]
1-1184 Cl [02514]
[02515]
1-1185 Cl [02516]
[02517]
1-1186 Cl [02518]
[02519]
1-1187 Cl [02520]
[02521]
1-1188 Cl [02522]
[02523]
1-1189 Cl [02524]
[02525]
1-1190 Cl [02526]
[02527]
1-1191 Cl [02528]
[02529]
1-1192 Cl [02530]
[02531]
1-1193 Cl [02532]
[02533]
1-1194 Cl [02534]
[02535]
1-1195 Cl [02536]
[02537]
1-1196 Cl [02538]
[02539]
1-1197 Cl [02540]
[02541]
1-1198 Cl [02542]
[02543]
1-1199 Cl [02544]
[02545]
1-1200 Cl [02546]
[02547]
1-1201 Cl [02548]
[02549]
1-1202 Cl [02550]
[02551]
1-1203 Cl [02552]
[02553]
1-1204 Cl [02554]
[02555]
1-1205 Cl [02556]
[02557]
1-1206 Cl [02558]
[02559]
1-1207 Cl [02560]
[02561]
1-1208 Cl [02562]
[02563]
1-1209 Cl [02564]
[02565]
1-1210 Cl [02566]
[02567]
1-1211 Cl [02568]
[02569]
1-1212 Cl [02570]
[02571]
1-1213 Cl [02572]
[02573]
1-1214 Cl [02574]
[02575]
1-1215 Cl [02576]
[02577]
1-1216 Cl [02578]
[02579]
1-1217 Cl [02580]
[02581]
1-1218 Cl [02582]
[02583]
1-1219 Cl [02584]
[02585]
1-1220 Cl [02586]
[02587]
1-1221 Cl [02588]
[02589]
1-1222 Cl [02590]
[02591]
1-1223 Cl [02592]
[02593]
1-1224 Cl [02594]
[02595]
1-1225 Cl [02596]
[02597]
1-1226 Cl [02598]
[02599]
1-1227 Cl [02600]
[02601]
1-1228 Cl [02602]
[02603]
1-1229 Cl [02604]
[02605]
1-1230 Cl [02606]
[02607]
1-1231 Cl [02608]
[02609]
1-1232 Cl [02610]
[02611]
1-1233 Cl [02612]
[02613]
1-1234 Cl [02614]
[02615]
1-1235 Cl [02616]
[02617]
1-1236 Cl [02618]
[02619]
1-1237 Cl [02620]
[02621]
1-1238 Cl [02622]
[02623]
1-1239 Cl [02624]
[02625]
1-1240 Cl [02626]
[02627]
1-1241 Cl [02628]
[02629]
1-1242 Cl [02630]
[02631]
1-1243 Cl [02632]
[02633]
1-1244 Cl [02634]
[02635]
1-1245 Cl [02636]
[02637]
1-1246 Cl [02638]
[02639]
1-1247 Cl [02640]
[02641]
1-1248 Cl [02642]
[02643]
1-1249 Cl [02644]
[02645]
1-1250 Cl [02646]
[02647]
1-1251 Cl [02648]
[02649]
1-1252 Cl [02650]
[02651]
1-1253 Cl [02652]
[02653]
1-1254 Cl [02654]
[02655]
1-1255 Cl [02656]
[02657]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.01 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.76 (s, 1H), 7.60 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H). 1-1256 Cl [02658]
[02659]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.02 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.78 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.08 (hept, J = 7.0 Hz, 1H), 1.26 (d, J = 7.0 Hz, 6H). 1-1257 Cl [02660]
[02661]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.75 (d, J = 4.5 Hz, 1H), 7.68-7.60 (m, 2H), 7.11-7.03 (m, 2H), 6.79 (d, J = 4.5 Hz, 1H), 1.50-1.35 (m, 1H), 1.02-0.96 (m, 2H), 0.94- 0.88 (m, 2H). 1-1258 Cl [02662]
[02663]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1259 Cl [02664]
[02665]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1260 Cl [02666]
[02667]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.79 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.70 (s, 2H), 2.10 (s, 3H). 1-1261 Cl [02668]
[02669]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.02 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.15 (s, 2H), 8.01- 7.93 (m, 2H), 7.80 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H). 1-1262 Cl [02670]
[02671]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 13.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.81 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.38 (s, 3H). 1-1263 Cl [02672]
[02673]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.78 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.48 (hept, J = 7.0 Hz, 1H), 1.21 (d, J = 7.0 Hz, 6H). 1-1264 Cl [02674]
[02675]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.34 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.89 (d, J = 5.0 Hz, 1H), 7.72 (s, 1H), 7.48 (d, J = 7.5 Hz, 1H), 7.42 (d, J = 7.5 Hz, 1H), 7.35- 7.27 (m, 2H). 1-1265 Cl [02676]
[02677]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.10-7.98 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.37-7.19 (m, 4H), 6.72-6.95 (m, 1H), 6.90-6.80 (m, 2H). 1-1266 Cl [02678]
[02679]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.07-7.92 (m, 2H), 7.74-7.72 (m, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.37- 7.25 (m, 2H), 6.84-6.82 (m, 1H), 6.68 (t, J = 7.5 Hz, 1H). 1-1267 Cl [02680]
[02681]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.08-7.95 (m, 2H), 7.77 (d, J = 2.5, 1H), 7.66 (d, J = 2.5 Hz, 1H), 7.46 (d, J = 5.0 Hz, 1H), 7.37-7.25 (m, 2H), 6.66 (t, J = 2.5 Hz, 1H). 1-1268 Cl [02682]
[02683]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.10-7.96 (m, 2H), 7.79-7.62 (m, 2H), 7.58 (d, J = 5.0 Hz, 1H), 7.38- 7.20 (m, 4H), 4.07 (q, J = 8.0 Hz, 2H), 3.97 (t, J = 8.0 Hz, 3H). 1-1269 Cl [02684]
[02685]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.07-7.92 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 7.40-7.24 (m, 2H), 3.58-3.40 (m, 4H), 1.81-1.68 (m, 4H), 1.59-1.43 (m, 2H). 1-1270 Cl CH.sub.3 [02686]
1-1271 Cl [02687]
[02688]
1-1272 Cl [02689]
[02690]
1-1273 Cl [02691]
[02692]
1-1274 Cl [02693]
[02694]
1-1275 Cl [02695]
[02696]
1-1276 Cl [02697]
[02698]
1-1277 Cl [02699]
[02700]
1-1278 Cl [02701]
[02702]
1-1279 Cl [02703]
[02704]
1-1280 Cl [02705]
[02706]
1-1281 Cl [02707]
[02708]
1-1282 Cl [02709]
[02710]
1-1283 Cl [02711]
[02712]
1-1284 Cl [02713]
[02714]
1-1285 Cl [02715]
[02716]
1-1286 Cl [02717]
[02718]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.53 (s, 1H), 8.79-8.73 (m, 2H), 7.64-7.57 (m, 2H), 7.33 (d, J = 4.5 Hz, 1H), 7.11-7.03 (m, 2H), 6.77 (d, J = 2.5 Hz, 1H). 1-1287 Cl [02719]
[02720]
1-1288 Cl [02721]
[02722]
1-1289 Cl [02723]
[02724]
1-1290 Cl [02725]
[02726]
1-1291 Cl [02727]
[02728]
1-1292 Cl [02729]
[02730]
1-1293 Cl [02731]
[02732]
1-1294 Cl [02733]
[02734]
1-1295 Cl [02735]
[02736]
1-1296 Cl [02737]
[02738]
1-1297 Cl [02739]
[02740]
1-1298 Cl [02741]
[02742]
1-1299 Cl [02743]
[02744]
1-1300 Cl [02745]
[02746]
1-1301 Cl [02747]
[02748]
1-1302 Cl [02749]
[02750]
1-1303 Cl [02751]
[02752]
1-1304 Cl [02753]
[02754]
1-1305 Cl [02755]
[02756]
1-1306 Cl [02757]
[02758]
1-1307 Cl [02759]
[02760]
1-1308 Cl [02761]
[02762]
1-1309 Cl [02763]
[02764]
1-1310 Cl [02765]
[02766]
1-1311 Cl [02767]
[02768]
1-1312 Cl [02769]
[02770]
1-1313 Cl [02771]
[02772]
1-1314 Cl [02773]
[02774]
1-1315 Cl [02775]
[02776]
1-1316 Cl [02777]
[02778]
1-1317 Cl [02779]
[02780]
1-1318 Cl [02781]
[02782]
1-1319 Cl [02783]
[02784]
1-1320 Cl [02785]
[02786]
1-1321 Cl [02787]
[02788]
1-1322 Cl [02789]
[02790]
1-1323 Cl [02791]
[02792]
1-1324 Cl [02793]
[02794]
1-1325 Cl [02795]
[02796]
1-1326 Cl [02797]
[02798]
1-1327 Cl [02799]
[02800]
1-1328 Cl [02801]
[02802]
1-1329 Cl [02803]
[02804]
1-1330 Cl [02805]
[02806]
1-1331 Cl [02807]
[02808]
1-1332 Cl [02809]
[02810]
1-1333 Cl [02811]
[02812]
1-1334 Cl [02813]
[02814]
1-1335 Cl [02815]
[02816]
1-1336 Cl [02817]
[02818]
1-1337 Cl [02819]
[02820]
1-1338 Cl [02821]
[02822]
1-1339 Cl [02823]
[02824]
1-1340 Cl [02825]
[02826]
1-1341 Cl [02827]
[02828]
1-1342 Cl [02829]
[02830]
1-1343 Cl [02831]
[02832]
1-1344 Cl [02833]
[02834]
1-1345 Cl [02835]
[02836]
1-1346 Cl [02837]
[02838]
1-1347 Cl [02839]
[02840]
1-1348 Cl [02841]
[02842]
1-1349 Cl [02843]
[02844]
1-1350 Cl [02845]
[02846]
1-1351 Cl [02847]
[02848]
1-1352 Cl [02849]
[02850]
1-1353 Cl [02851]
[02852]
1-1354 Cl [02853]
[02854]
1-1355 Cl [02855]
[02856]
1-1356 Cl [02857]
[02858]
1-1357 Cl [02859]
[02860]
1-1358 Cl [02861]
[02862]
1-1359 Cl [02863]
[02864]
1-1360 Cl [02865]
[02866]
1-1361 Cl [02867]
[02868]
1-1362 Cl [02869]
[02870]
1-1363 Cl [02871]
[02872]
1-1364 Cl [02873]
[02874]
1-1365 Cl [02875]
[02876]
1-1366 Cl [02877]
[02878]
1-1367 Cl [02879]
[02880]
1-1368 Cl [02881]
[02882]
1-1369 Cl [02883]
[02884]
1-1370 Cl [02885]
[02886]
1-1371 Cl [02887]
[02888]
1-1372 Cl [02889]
[02890]
1-1373 Cl [02891]
[02892]
1-1374 Cl [02893]
[02894]
1-1375 Cl [02895]
[02896]
1-1376 Cl [02897]
[02898]
1-1377 Cl [02899]
[02900]
1-1378 Cl [02901]
[02902]
1-1379 Cl [02903]
[02904]
1-1380 Cl [02905]
[02906]
1-1381 Cl [02907]
[02908]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.54 (t, J = 1.5 Hz, 1H), 8.19 (dd, J = 7.5, 1.5 Hz, 1H), 8.14-7.92 (m, 3H), 7.88 (d, J = 5.0 Hz, 1H), 7.67-7.58 (m, 2H), 6.77 (d, J = 2.5 Hz, 1H). 1-1382 Cl [02909]
[02910]
1-1383 Cl [02911]
[02912]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 9.26 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 5.5 Hz, 1H), 8.60-8.58 (m, 1H), 8.23 (dd, J = 7.5, 1.5 Hz, 1H), 8.17-8.14 (m, 1H), 7.87-7.82 (m, 2H), 7.66 (d, J = 2.5 Hz, 1H), 6.77 (d, J = 2.5 Hz, 1H). 1-1384 Cl [02913]
[02914]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.94-8.85 (m, 2H), 8.81-8.73 (m, 2H), 8.40 (d, J = 1.5 Hz, 1H), 8.20-8.13 (m, 1H), 8.05- 7.99 (m, 1H), 7.95-7.86 (m, 5H), 6.77 (d, J = 2.5 Hz, 1H). 1-1385 Cl [02915]
[02916]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.21 (dd, J = 7.5, 1.5 Hz, 1H), 8.13-7.98 (m, 2H), 7.91 (d, J = 5.0 Hz, 1H), 7.66-7.58 (m, 2H), 7.44 (td, J = 7.5, 1.5 Hz, 1H), 7.38-7.22 (m, 1H), 6.77 (d, J = 7.5 Hz, 1H). 1-1386 Cl [02917]
[02918]
1-1387 Cl [02919]
[02920]
1-1388 Cl [02921]
[02922]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.25-8.12 (m, 2H), 8.05-7.88 (m, 2H), 7.72- 7.62 (m, 2H), 7.60-7.55 (m, 1H), 7.48-7.21 (m, 1H), 6.77 (d, J = 2.5 Hz, 1H). 1-1389 Cl [02923]
[02924]
1-1390 Cl [02925]
[02926]
1-1391 Cl [02927]
[02928]
1-1392 Cl [02929]
[02930]
1-1393 Cl [02931]
[02932]
1-1394 Cl [02933]
[02934]
1-1395 Cl [02935]
[02936]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.18 (s, 1H), 8.90 (s, 1H), 8.77-8.61 (m, 2H), 8.46 (d, J = 5.0 Hz, 1H), 8.02 (d, J = 2.5 Hz, 1H), 7.43 (d, J = 5.0 Hz, 1H), 6.77 (d, J = 2.5 Hz, 1H), 2.42 (s, 3H). 1-1396 Cl [02937]
[02938]
1-1397 Cl [02939]
[02940]
1-1398 Cl [02941]
[02942]
1-1399 Cl [02943]
[02944]
1-1400 Cl [02945]
[02946]
1-1401 Cl [02947]
[02948]
1-1402 Cl [02949]
[02950]
1-1403 Cl [02951]
[02952]
1-1404 Cl [02953]
[02954]
1-1405 Cl [02955]
[02956]
1-1406 Cl [02957]
[02958]
1-1407 Cl [02959]
[02960]
1-1408 Cl [02961]
[02962]
1-1409 Cl [02963]
[02964]
1-1410 Cl [02965]
[02966]
1-1411 Cl [02967]
[02968]
1-1412 Cl [02969]
[02970]
1-1413 Cl [02971]
[02972]
1-1414 Cl [02973]
[02974]
1-1415 Cl [02975]
[02976]
1-1416 Cl [02977]
[02978]
1-1417 Cl [02979]
[02980]
1-1418 Cl [02981]
[02982]
1-1419 Cl [02983]
[02984]
1-1420 Cl [02985]
[02986]
1-1421 Cl [02987]
[02988]
1-1422 Cl [02989]
[02990]
1-1423 Cl [02991]
[02992]
1-1424 Cl [02993]
[02994]
1-1425 Cl [02995]
[02996]
1-1426 Cl [02997]
[02998]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 9.37-9.33 (m, 3H), 8.83 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 2.5 Hz, 1H), 7.99 (d, J = 5.0 Hz, 1H), 6.77 (d, J = 2.5 Hz, 1H). 1-1427 Cl [02999]
[03000]
1-1428 Cl [03001]
[03002]
1-1429 Cl [03003]
[03004]
1-1430 Cl [03005]
[03006]
1-1431 Cl [03007]
[03008]
1-1432 Cl [03009]
[03010]
1-1433 Cl [03011]
[03012]
1-1434 Cl [03013]
[03014]
1-1435 Cl [03015]
[03016]
1-1436 Cl [03017]
[03018]
1-1437 Cl [03019]
[03020]
1-1438 Cl [03021]
[03022]
1-1439 Cl [03023]
[03024]
1-1440 Cl [03025]
[03026]
1-1441 Cl [03027]
[03028]
1-1442 Cl [03029]
[03030]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 2.5 Hz, 1H), 7.97 (d, J = 5.0 Hz, 1H), 7.80 (s, 1H), 6.97 (s, 1H), 6.77 (d, J = 2.5 Hz, 1H), 4.29 (q, J = 8.0 Hz, 2H), 1.16 (t, J = 8.0 Hz, 3H). 1-1443 Cl [03031]
[03032]
1-1444 Cl [03033]
[03034]
1-1445 Cl [03035]
[03036]
1-1446 Cl [03037]
[03038]
1-1447 Cl [03039]
[03040]
1-1448 Cl [03041]
[03042]
1-1449 Cl [03043]
[03044]
1-1450 Cl [03045]
[03046]
1-1451 Cl [03047]
[03048]
1-1452 Cl [03049]
[03050]
1-1453 Cl [03051]
[03052]
1-1454 Cl [03053]
[03054]
1-1455 Cl [03055]
[03056]
1-1456 Cl [03057]
[03058]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 2.5 Hz, 1H), 8.03 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 2.5 Hz, 1H), 7.47 (d, J = 4.0 Hz, 1H), 7.15-7.12 (m, 1H), 6.77 (d, J = 2.5 Hz, 1H). 1-1457 Cl [03059]
[03060]
1-1458 Cl [03061]
[03062]
1-1459 Cl [03063]
[03064]
1-1460 Cl [03065]
[03066]
1-1461 Cl [03067]
[03068]
1-1462 Cl [03069]
[03070]
1-1463 Cl [03071]
[03072]
1-1464 CH.sub.3 [03073]
[03074]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 7.98-7.90 (m, 2H), 7.85 (s, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.51 (s, 3H), 2.35 (s, 3H). 1-1465 F [03075]
[03076]
1-1466 Br [03077]
[03078]
1-1467 [03079]
[03080]
[03081]
1-1468 CF.sub.3 [03082]
[03083]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.84 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.31 (s, 3H). 1-1469 [03084]
[03085]
[03086]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.83 (s, 1H), 7.69-7.59 (m, 3H), 7.47-7.40 (m, 2H), 7.39-7.21 (m, 1H), 7.35-7.27 (m, 2H), 2.23 (s, 3H). 1-1470 [03087]
[03088]
[03089]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.09-8.01 (m, 2H), 7.85 (s, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.67 (s, 3H), 2.31 (s, 3H). 1-1471 [03090]
[03091]
[03092]
1-1472 [03093]
[03094]
[03095]
1-1473 [03096]
[03097]
[03098]
1-1474 [03099]
[03100]
[03101]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.58 (d, J = 4.9 Hz, 1H), 8.03-7.96 (m, 2H), 7.85 (s, 1H), 7.47 (d, J = 4.9 Hz, 1H), 7.35-7.27 (m, 2H), 3.00 (q, J = 8.0 Hz, 2H), 2.31 (s, 3H), 1.19 (t, J = 8.0 Hz, 3H). 1-1475 [03102]
[03103]
[03104]
1-1476 [03105]
[03106]
[03107]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.14-8.06 (m, 2H), 7.86 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.63-2.61 (m, 1H), 2.59-2.56 (m, 1H), 2.31 (s, 3H), 1.22 (t, J = 8.0 Hz, 3H). 1-1477 [03108]
[03109]
[03110]
1-1478 [03111]
[03112]
[03113]
1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.06-7.98 (m, 2H), 7.83 (s, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.75 (s, 6H), 2.30 (s, 3H). 1-1479 [03114]
[03115]
[03116]
1-1480 Et [03117]
[03118]
1-1481 [03119]
[03120]
[03121]
1-1482 NO.sub.2 [03122]
[03123]
1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 7.99-7.91 (m, 2H), 7.86 (s, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.31 (s, 3H). 1-1483 CN [03124]
[03125]
1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 9.01 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.84 (s, 1H), 7.69 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.31 (s, 3H). 1-1484 [03126]
[03127]
[03128]
1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.03-7.96 (m, 2H), 7.84 (s, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 3.28 (s, 3H), 2.30 (s, 3H). 1-1485 [03129]
[03130]
[03131]
1-1486 [03132]
[03133]
[03134]
1-1487 [03135]
[03136]
[03137]
1-1488 [03138]
[03139]
[03140]
1-1489 [03141]
[03142]
[03143]
1-1490 [03144]
[03145]
[03146]
1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.01-7.94 (m, 2H), 7.80 (s, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.31 (s, 1H), 2.39 (s, 3H). 1-1491 [03147]
[03148]
[03149]
1-1492 [03150]
[03151]
[03152]
1-1493 [03153]
[03154]
[03155]
1-1494 Cl [03156]
[03157]
1-1495 Cl [03158]
[03159]
1-1496 Cl [03160]
[03161]
1-1497 Cl [03162]
[03163]
1-1498 Cl [03164]
[03165]
1-1499 Cl [03166]
[03167]
1-1500 Cl [03168]
[03169]
1-1501 Cl [03170]
[03171]
1-1502 Cl [03172]
[03173]
1-1503 Cl [03174]
[03175]
1-1504 Cl [03176]
[03177]
1-1505 Cl [03178]
[03179]
1-1506 Cl [03180]
[03181]
1-1507 Cl [03182]
[03183]
1-1508 Cl [03184]
[03185]
1-1509 Cl [03186]
[03187]
1-1510 Cl [03188]
[03189]
1-1511 Cl [03190]
[03191]
1-1512 Cl [03192]
[03193]
1-1513 Cl [03194]
[03195]
1-1514 Cl [03196]
[03197]
1-1515 Cl [03198]
[03199]
1-1516 Cl [03200]
[03201]
1-1517 Cl [03202]
[03203]
1-1518 Cl [03204]
[03205]
1-1519 Cl [03206]
[03207]
1-1520 Cl [03208]
[03209]
1-1521 Cl [03210]
[03211]
1-1522 Cl [03212]
[03213]
1-1523 Cl [03214]
[03215]
1-1524 Cl [03216]
[03217]
1-1525 Cl [03218]
[03219]
1-1526 Cl [03220]
[03221]
1-1527 Cl [03222]
[03223]
1-1528 Cl [03224]
[03225]
1-1529 Cl [03226]
[03227]
1-1530 Cl [03228]
[03229]
1-1531 Cl [03230]
[03231]
1-1532 Cl [03232]
[03233]
1-1533 Cl [03234]
[03235]
1-1534 Cl [03236]
[03237]
1-1535 Cl [03238]
[03239]
1-1536 Cl [03240]
[03241]
1-1537 Cl [03242]
[03243]
1-1538 Cl [03244]
[03245]
1-1539 Cl [03246]
[03247]
1-1540 Cl [03248]
[03249]
1-1541 Cl [03250]
[03251]
1-1542 Cl [03252]
[03253]
1-1543 Cl [03254]
[03255]
1-1544 Cl [03256]
[03257]
1-1545 Cl [03258]
[03259]
1-1546 Cl [03260]
[03261]
1-1547 Cl [03262]
[03263]
1-1548 Cl [03264]
[03265]
1-1549 Cl [03266]
[03267]
1-1550 Cl [03268]
[03269]
1-1551 Cl [03270]
[03271]
1-1552 Cl [03272]
[03273]
1-1553 Cl [03274]
[03275]
1-1554 Cl [03276]
[03277]
1-1555 Cl [03278]
[03279]
1-1556 Cl [03280]
[03281]
1-1557 Cl [03282]
[03283]
1-1558 Cl [03284]
[03285]
1-1559 Cl [03286]
[03287]
1-1560 Cl [03288]
[03289]
1-1561 Cl [03290]
[03291]
1-1562 Cl [03292]
[03293]
1-1563 Cl [03294]
[03295]
1-1564 Cl [03296]
[03297]
1-1565 Cl [03298]
[03299]
1-1566 Cl [03300]
[03301]
1-1567 Cl [03302]
[03303]
1-1568 Cl [03304]
[03305]
1-1569 Cl [03306]
[03307]
1-1570 Cl [03308]
[03309]
1-1571 Cl [03310]
[03311]
1-1572 Cl [03312]
[03313]
1-1573 Cl [03314]
[03315]
1-1574 Cl [03316]
[03317]
1-1575 Cl [03318]
[03319]
1-1576 Cl [03320]
[03321]
1-1577 Cl [03322]
[03323]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.78 (s, 1H), 7.63-7.56 (m, 2H), 7.41 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 2.31 (s, 3H). 1-1578 Cl [03324]
[03325]
1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.76 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.70 (q, J = 8.0 Hz, 2H), 1.25 (t, J = 8.0 Hz, 3H). 1-1579 Cl [03326]
[03327]
1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 8.10 (s, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.46-2.32 (m, 1H), 1.12-1.02 (m, 2H), 0.85-0.69 (m, 2H). 1-1580 Cl [03328]
[03329]
1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.85 (s, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.64 (s, 2H). 1-1581 Cl [03330]
[03331]
1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 3H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1582 Cl [03332]
[03333]
1H NMR (500 MHz, DMSO-d6) δ 11.99 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.82 (s, 1H), 4.63 (s, 2H), 3.33 (s, 3H). 1-1583 Cl [03334]
[03335]
1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.72 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1584 Cl [03336]
[03337]
1H NMR (500 MHz, DMSO-d6) δ 12.43 (s, 1H), 10.68 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.04- 7.96 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 5.88 (s, 1H), 3.47 (q, J = 8.0 Hz, 2H), 1.07 (t, J = 8.0 Hz, 3H). 1-1585 Cl [03338]
[03339]
1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.11 (s, 1H), 8.07-7.99 (m, 2H), 7.65-7.58 (m, 3H), 7.58-7.52 (m, 2H), 7.35-7.27 (m, 2H). 1-1586 Cl [03340]
[03341]
1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.00 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.07-7.99 (m, 2H), 7.86-7.79 (m, 2H), 7.73-7.65 (m, 1H), 7.66-7.56 (m, 3H), 7.35-7.27 (m, 2H). 1-1587 Cl [03342]
[03343]
1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.73-8.58 (m, 1H), 8.07- 8.00 (m, 2H), 7.97 (dd, J = 8.0, 1.0 Hz, 1H), 7.86-7.69 (m, 1H), 7.63 (d, J = 5.0 Hz, 1H), 7.48-7.36 (m, 1H), 7.35-7.27 (m, 2H), 6.74 (s, 1H). 1-1588 Cl [03344]
[03345]
1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.30 (s, 1H), 8.05-7.97 (m, 2H), 7.70 (d, J = 2.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.19-7.09 (m, 2H). 1-1589 Cl [03346]
[03347]
1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.85 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 8.28 (s, 1H), 8.05-7.98 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1590 Cl CH.sub.3 [03348]
1-1591 Cl [03349]
[03350]
1-1592 Cl [03351]
[03352]
1-1593 Cl [03353]
[03354]
1-1594 Cl [03355]
[03356]
1-1595 Cl [03357]
[03358]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 7.44 (d, J = 2.5 Hz, 1H), 7.25 (d, J = 2.5 Hz, 1H), 6.42-6.36 (m, 1H), 4.34 (t, J = 6.0 Hz, 2H), 3.33-3.31 (m, 2H), 3.05-3.01 (m, 2H), 1.96 (s, 3H). 1-1596 Cl [03359]
[03360]
1-1597 Cl [03361]
[03362]
1-1598 Cl [03363]
[03364]
1-1599 Cl [03365]
[03366]
1-1600 Cl [03367]
[03368]
1-1601 Cl [03369]
[03370]
1-1602 Cl [03371]
[03372]
1-1603 Cl [03373]
[03374]
1-1604 Cl [03375]
[03376]
1-1605 Cl [03377]
[03378]
1-1606 Cl [03379]
[03380]
1-1607 Cl [03381]
[03382]
1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.56-7.48 (m, 2H), 7.35-7.27 (m, 2H), 7.23 (d, J = 2.5 Hz, 1H). 1-1608 Cl [03383]
[03384]
1-1609 Cl [03385]
[03386]
1-1610 Cl [03387]
[03388]
1-1611 Cl [03389]
[03390]
1-1612 Cl [03391]
[03392]
1-1613 Cl [03393]
[03394]
1-1614 Cl [03395]
[03396]
1-1615 Cl [03397]
[03398]
1-1616 Cl [03399]
[03400]
1-1617 Cl [03401]
[03402]
1-1618 Cl [03403]
[03404]
1-1619 Cl [03405]
[03406]
1-1620 Cl [03407]
[03408]
1-1621 Cl [03409]
[03410]
1-1622 Cl [03411]
[03412]
1-1623 Cl [03413]
[03414]
1-1624 Cl [03415]
[03416]
1-1625 Cl [03417]
[03418]
1-1626 Cl [03419]
[03420]
1-1627 Cl [03421]
[03422]
1-1628 Cl [03423]
[03424]
1-1629 Cl [03425]
[03426]
1-1630 Cl [03427]
[03428]
1-1631 Cl [03429]
[03430]
1-1632 Cl [03431]
[03432]
1-1633 Cl [03433]
[03434]
1-1634 Cl [03435]
[03436]
1-1635 Cl [03437]
[03438]
1-1636 Cl [03439]
[03440]
1-1637 Cl [03441]
[03442]
1-1638 Cl [03443]
[03444]
1-1639 Cl [03445]
[03446]
1-1640 Cl [03447]
[03448]
1-1641 Cl [03449]
[03450]
1-1642 Cl [03451]
[03452]
1-1643 Cl [03453]
[03454]
1-1644 Cl [03455]
[03456]
1-1645 Cl [03457]
[03458]
1-1646 Cl [03459]
[03460]
1-1647 Cl [03461]
[03462]
1-1648 Cl [03463]
[03464]
1-1649 Cl [03465]
[03466]
1-1650 Cl [03467]
[03468]
1-1651 Cl [03469]
[03470]
1-1652 Cl [03471]
[03472]
1-1653 Cl [03473]
[03474]
1-1654 Cl [03475]
[03476]
1-1655 Cl [03477]
[03478]
1-1656 Cl [03479]
[03480]
1-1657 Cl [03481]
[03482]
1-1658 Cl [03483]
[03484]
1-1659 Cl [03485]
[03486]
1-1660 Cl [03487]
[03488]
1-1661 Cl [03489]
[03490]
1-1662 Cl [03491]
[03492]
1-1663 Cl [03493]
[03494]
1-1664 Cl [03495]
[03496]
1-1665 Cl [03497]
[03498]
1-1666 Cl [03499]
[03500]
1-1667 Cl [03501]
[03502]
1-1668 Cl [03503]
[03504]
1-1669 Cl [03505]
[03506]
1-1670 Cl [03507]
[03508]
1-1671 Cl [03509]
[03510]
1-1672 Cl [03511]
[03512]
1-1673 Cl [03513]
[03514]
1-1674 Cl [03515]
[03516]
1-1675 Cl [03517]
[03518]
1-1676 Cl [03519]
[03520]
1-1677 Cl [03521]
[03522]
1-1678 Cl [03523]
[03524]
1-1679 Cl [03525]
[03526]
1-1680 Cl [03527]
[03528]
1-1681 Cl [03529]
[03530]
1-1682 Cl [03531]
[03532]
1-1683 Cl [03533]
[03534]
1-1684 Cl [03535]
[03536]
1-1685 Cl [03537]
[03538]
1-1686 Cl [03539]
[03540]
1-1687 Cl [03541]
[03542]
1-1688 Cl [03543]
[03544]
1-1689 Cl [03545]
[03546]
1-1690 Cl [03547]
[03548]
1-1691 Cl [03549]
[03550]
1-1692 Cl [03551]
[03552]
1-1693 Cl [03553]
[03554]
1-1694 Cl [03555]
[03556]
1-1695 Cl [03557]
[03558]
1-1696 Cl [03559]
[03560]
1-1697 Cl [03561]
[03562]
1-1698 Cl [03563]
[03564]
1-1699 Cl [03565]
[03566]
1-1700 Cl [03567]
[03568]
1-1701 Cl [03569]
[03570]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.12 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.39 (dd, J = 7.5, 2.0 Hz, 1H), 8.15-8.07 (m, 2H), 8.03-8.01 (m, 1H), 7.90 (t, J = 7.5 Hz, 1H), 7.64 (d, J = 5.0 Hz, 1H), 7.60-7.56 (m, 1H), 7.52-7.50 (m, 1H), 7.47 (d, J = 2.0 Hz, 1H), 7.25 (d, J = 2.0 Hz, 1H). 1-1702 Cl [03571]
[03572]
1-1703 Cl [03573]
[03574]
1-1704 Cl [03575]
[03576]
1-1705 Cl [03577]
[03578]
1-1706 Cl [03579]
[03580]
1-1707 Cl [03581]
[03582]
1-1708 Cl [03583]
[03584]
1-1709 Cl [03585]
[03586]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.63 (s, 1H), 8.48 (dd, J = 7.5, 2.0 Hz, 1H), 8.15-8.10 (m, 2H), 8.07-8.04 (m, 1H), 7.61 (d, J = 5.0 Hz, 1H), 7.56-7.54 (m, 1H), 7.49-7.46 (m, 1H), 7.45 (d, J = 2.5 Hz, 1H), 7.25 (d, J = 2.5 Hz, 1H). 1-1710 Cl [03587]
[03588]
1-1711 Cl [03589]
[03590]
1-1712 Cl [03591]
[03592]
1-1713 Cl [03593]
[03594]
1-1714 Cl [03595]
[03596]
1-1715 Cl [03597]
[03598]
1-1716 Cl [03599]
[03600]
1-1717 Cl [03601]
[03602]
1-1718 Cl [03603]
[03604]
1-1719 Cl [03605]
[03606]
1-1720 Cl [03607]
[03608]
1-1721 Cl [03609]
[03610]
1-1722 Cl [03611]
[03612]
1-1723 Cl [03613]
[03614]
1-1724 Cl [03615]
[03616]
1-1725 Cl [03617]
[03618]
1-1726 Cl [03619]
[03620]
1-1727 Cl [03621]
[03622]
1-1728 Cl [03623]
[03624]
1-1729 Cl [03625]
[03626]
1-1730 Cl [03627]
[03628]
1-1731 Cl [03629]
[03630]
1-1732 Cl [03631]
[03632]
1-1733 Cl [03633]
[03634]
1-1734 Cl [03635]
[03636]
1-1735 Cl [03637]
[03638]
1-1736 Cl [03639]
[03640]
1-1737 Cl [03641]
[03642]
1-1738 Cl [03643]
[03644]
1-1739 Cl [03645]
[03646]
1-1740 Cl [03647]
[03648]
1-1741 Cl [03649]
[03650]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.13 (s, 1H), 8.02 (d, J = 5.0 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 2.5 Hz, 1H), 7.24 (d, J = 2.5 Hz, 1H). 1-1742 Cl [03651]
[03652]
1-1743 Cl [03653]
[03654]
1-1744 Cl [03655]
[03656]
1-1745 Cl [03657]
[03658]
1-1746 Cl [03659]
[03660]
1-1747 Cl [03661]
[03662]
1-1748 Cl [03663]
[03664]
1-1749 Cl [03665]
[03666]
1-1750 Cl [03667]
[03668]
1-1751 Cl [03669]
[03670]
1-1752 Cl [03671]
[03672]
1-1753 Cl [03673]
[03674]
1-1754 Cl [03675]
[03676]
1-1755 Cl [03677]
[03678]
1-1756 Cl [03679]
[03680]
1-1757 Cl [03681]
[03682]
1-1758 Cl [03683]
[03684]
1-1759 Cl [03685]
[03686]
1-1760 Cl [03687]
[03688]
1-1761 Cl [03689]
[03690]
1-1762 Cl [03691]
[03692]
1-1763 Cl [03693]
[03694]
1-1764 Cl [03695]
[03696]
1-1765 Cl [03697]
[03698]
1-1766 Cl [03699]
[03700]
1-1767 Cl [03701]
[03702]
1-1768 Cl [03703]
[03704]
1-1769 Cl [03705]
[03706]
1-1770 Cl [03707]
[03708]
1-1771 Cl [03709]
[03710]
1-1772 Cl [03711]
[03712]
1-1773 Cl [03713]
[03714]
1-1774 Cl [03715]
[03716]
1-1775 Cl [03717]
[03718]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 2.5 Hz, 1H), 7.26 (d, J = 2.5 Hz, 1H), 7.24 (d, J = 2.5 Hz, 1H), 6.69 (d, J = 2.5 Hz, 1H), 3.92 (s, 3H). 1-1776 Cl [03719]
[03720]
1-1777 Cl [03721]
[03722]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 7.50 (d, J = 2.5 Hz, 1H), 7.28-7.22 (m, 2H), 6.98 (t, J = 2.5 Hz, 1H). 1-1778 Cl [03723]
[03724]
1-1779 Cl [03725]
[03726]
1-1780 Cl [03727]
[03728]
1-1781 Cl [03729]
[03730]
1-1782 Cl [03731]
[03732]
1-1783 Cl [03733]
[03734]
1-1784 Cl [03735]
[03736]
1-1785 Cl [03737]
[03738]
1-1786 Cl [03739]
[03740]
1-1787 CH.sub.3 [03741]
[03742]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.00-7.92 (m, 2H), 7.52 (d, J = 2.5 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.22 (d, J = 2.5 Hz, 1H), 2.44 (s, 3H). 1-1788 F [03743]
[03744]
1-1789 Br [03745]
[03746]
1-1790 [03747]
[03748]
[03749]
1-1791 CF.sub.3 [03750]
[03751]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.55-7.48 (m, 2H), 7.35-7.27 (m, 2H), 7.21 (d, J = 2.5 Hz, 1H). 1-1792 [03752]
[03753]
[03754]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.13 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.67-7.61 (m, 3H), 7.49-7.35 (m, 4H), 7.35- 7.27 (m, 2H), 7.23 (d, J = 2.5 Hz, 1H). 1-1793 [03755]
[03756]
[03757]
1-1794 [03758]
[03759]
[03760]
1-1795 [03761]
[03762]
[03763]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.53 (d, J = 5.0 Hz, 1H), 8.10-8.02 (m, 2H), 7.52 (d, J = 2.5 Hz, 1H), 7.45 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.21 (d, J = 2.5 Hz, 1H), 5.03 (s, 2H). 1-1796 [03764]
[03765]
[03766]
1-1797 [03767]
[03768]
[03769]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.25 (d, J = 2.5 Hz, 1H), 3.00 (q, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H). 1-1798 [03770]
[03771]
[03772]
1-1799 [03773]
[03774]
[03775]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.34 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.24 (d, J = 7.5 Hz, 1H), 2.61-2.59 (m, 1H), 2.57-2.55 (m, 1H), 1.21 (t, J = 8.0 Hz, 3H). 1-1800 [03776]
[03777]
[03778]
1-1801 [03779]
[03780]
[03781]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.36 (d, J = 5.0 Hz, 1H), 8.07-8.00 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.42 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.24 (d, J = 2.5 Hz, 1H), 2.77 (s, 6H). 1-1802 [03782]
[03783]
[03784]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.93 (d, J = 5.0 Hz, 1H), 7.51 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.26 (d, J = 2.5 Hz, 1H), 2.35 (s, 6H). 1-1803 Et [03785]
[03786]
1-1804 [03787]
[03788]
[03789]
1-1805 NO.sub.2 [03790]
[03791]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.73 (d, J = 5.0 Hz, 1H), 7.47 (d, J = 2.5 Hz, 1H), 7.34-7.29 (m, 2H), 7.27 (d, J = 2.5 Hz, 1H). 1-1806 CN [03792]
[03793]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 9.02 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.46 (d, J = 2.5 Hz, 1H), 7.37-7.27 (m, 2H), 7.25 (d, J = 2.5 Hz, 1H). 1-1807 [03794]
[03795]
[03796]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.12 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.51 (d, J = 2.5 Hz, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.20 (d, J = 2.5 Hz, 1H), 4.68 (s, 2H), 3.28 (s, 3H). 1-1808 [03797]
[03798]
[03799]
1-1809 [03800]
[03801]
[03802]
1-1810 [03803]
[03804]
[03805]
1-1811 [03806]
[03807]
[03808]
1-1812 [03809]
[03810]
[03811]
1-1813 [03812]
[03813]
[03814]
1-1814 [03815]
[03816]
[03817]
1-1815 [03818]
[03819]
[03820]
1-1816 [03821]
[03822]
[03823]
1-1817 Cl [03824]
[03825]
1-1818 Cl [03826]
[03827]
1-1819 Cl [03828]
[03829]
1-1820 Cl [03830]
[03831]
1-1821 Cl [03832]
[03833]
1-1822 Cl [03834]
[03835]
1-1823 Cl [03836]
[03837]
1-1824 Cl [03838]
[03839]
1-1825 Cl [03840]
[03841]
1-1826 Cl [03842]
[03843]
1-1827 Cl [03844]
[03845]
1-1828 Cl [03846]
[03847]
1-1829 Cl [03848]
[03849]
1-1830 Cl [03850]
[03851]
1-1831 Cl [03852]
[03853]
1-1832 Cl [03854]
[03855]
1-1833 Cl [03856]
[03857]
1-1834 Cl [03858]
[03859]
1-1835 Cl [03860]
[03861]
1-1836 Cl [03862]
[03863]
1-1837 Cl [03864]
[03865]
1-1838 Cl [03866]
[03867]
1-1839 Cl [03868]
[03869]
1-1840 Cl [03870]
[03871]
1-1841 Cl [03872]
[03873]
1-1842 Cl [03874]
[03875]
1-1843 Cl [03876]
[03877]
1-1844 Cl [03878]
[03879]
1-1845 Cl [03880]
[03881]
1-1846 Cl [03882]
[03883]
1-1847 Cl [03884]
[03885]
1-1848 Cl [03886]
[03887]
1-1849 Cl [03888]
[03889]
1-1850 Cl [03890]
[03891]
1-1851 Cl [03892]
[03893]
1-1852 Cl [03894]
[03895]
1-1853 Cl [03896]
[03897]
1-1854 Cl [03898]
[03899]
1-1855 Cl [03900]
[03901]
1-1856 Cl [03902]
[03903]
1-1857 Cl [03904]
[03905]
1-1858 Cl [03906]
[03907]
1-1859 Cl [03908]
[03909]
1-1860 Cl [03910]
[03911]
1-1861 Cl [03912]
[03913]
1-1862 Cl [03914]
[03915]
1-1863 Cl [03916]
[03917]
1-1864 Cl [03918]
[03919]
1-1865 Cl [03920]
[03921]
1-1866 Cl [03922]
[03923]
1-1867 Cl [03924]
[03925]
1-1868 Cl [03926]
[03927]
1-1869 Cl [03928]
[03929]
1-1870 Cl [03930]
[03931]
1-1871 Cl [03932]
[03933]
1-1872 Cl [03934]
[03935]
1-1873 Cl [03936]
[03937]
1-1874 Cl [03938]
[03939]
1-1875 Cl [03940]
[03941]
1-1876 Cl [03942]
[03943]
1-1877 Cl [03944]
[03945]
1-1878 Cl [03946]
[03947]
1-1879 Cl [03948]
[03949]
1-1880 Cl [03950]
[03951]
1-1881 Cl [03952]
[03953]
1-1882 Cl [03954]
[03955]
1-1883 Cl [03956]
[03957]
1-1884 Cl [03958]
[03959]
1-1885 Cl [03960]
[03961]
1-1886 Cl [03962]
[03963]
1-1887 Cl [03964]
[03965]
1-1888 Cl [03966]
[03967]
1-1889 Cl [03968]
[03969]
1-1890 Cl [03970]
[03971]
1-1891 Cl [03972]
[03973]
1-1892 Cl [03974]
[03975]
1-1893 Cl [03976]
[03977]
1-1894 Cl [03978]
[03979]
1-1895 Cl [03980]
[03981]
1-1896 Cl [03982]
[03983]
1-1897 Cl [03984]
[03985]
1-1898 Cl [03986]
[03987]
1-1899 Cl [03988]
[03989]
1-1900 Cl [03990]
[03991]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.34 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.25 (s, 1H), 2.65 (t, J = 8.0 Hz, 2H), 1.70-1.48 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H). 1-1901 Cl [03992]
[03993]
.sup.1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.75 (d, J = 5.0 Hz, 1H), 7.36 (s, 1H), 7.35-7.27 (m, 2H). 1-1902 Cl [03994]
[03995]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.14 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.06-7.99 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.81 (s, 1H), 3.81 (s, 3H). 1-1903 Cl [03996]
[03997]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.45 (s, 1H), 7.35- 7.27 (m, 2H), 2.40 (s, 3H). 1-1904 Cl [03998]
[03999]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.04 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1905 Cl [04000]
[04001]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.69 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.20 (s, 6H). 1-1906 Cl [04002]
[04003]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.07 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.74 (s, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H). 1-1907 Cl [04004]
[04005]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.09 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 7.46 (s, 1H), 7.35- 7.27 (m, 2H), 3.83 (s, 2H), 2.60 (s, 3H). 1-1908 Cl [04006]
[04007]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.11 (s, 1H), 10.52 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.06- 7.99 (m, 2H), 7.69 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.13 (s, 3H). 1-1909 Cl [04008]
[04009]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.08 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.66 (d, J = 5.5 Hz, 2H), 8.05-8.01 (m, 2H), 7.99 (d, J = 5.5, 2H), 7.79 (s, 1H), 7.71 (d, J = 5.0 H,z 1H), 7.35- 7.27 (m, 2H). 1-1910 Cl [04010]
[04011]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.05 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.20-8.13 (m, 2H), 7.90 (s, 1H), 7.66 (d, J = 5.0 Hz, 1H), 7.64-7.60 (m, 2H), 7.55-7.51 (m, 2H), 7.35-7.27 (m, 2H). 1-1911 Cl [04012]
[04013]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.06 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.22 (s, 1H), 5.08 (t, J = 7.0 Hz, 1H), 3.90-3.79 (m, 2H), 2.26-2.11 (m, 2H), 1.88-1.76 (m, 2H). 1-1912 OMe CH.sub.3 [04014]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.84 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 3.74 (s, 3H), 2.51 (s, 3H), 2.46 (s, 3H). 1-1913 Cl [04015]
[04016]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 6.99-6.94 (m, 1H), 6.13-6.09 (m, 1H), 5.63-5.59 (m, 1H), 4.33 (s, 3H). 1-1914 Cl [04017]
[04018]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.33 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H), 3.70 (t, J = 6.0 Hz, 2H), 2.43 (t, J = 7.5 Hz, 2H), 2.11-2.06 (m, 2H). 1-1915 Cl [04019]
[04020]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.74-7.70 (m, 2H), 7.49 (d, J = 5.0 Hz, 1H), 7.27-7.23 (m, 2H), 4.31 (s, 3H), 2.74-2.69 (m, 2H), 1.19 (t, J = 8.0 Hz, 3H). 1-1916 Cl [04021]
[04022]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.72-7.69 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.40-7.37 (m, 2H), 4.36 (s, 3H), 2.89-2.84 (m, 1H), 1.20 (d, J = 7.0 Hz, 6H). 1-1917 Cl [04023]
[04024]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.35 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.88-7.85 (m, 1H), 7.81-7.79 (m, 1H), 7.63-7.60 (m, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.34-7.31 (m, 1H), 4.39 (s, 3H), 2.63 (t, J = 5.5 Hz, 2H), 1.56-1.51 (m, 2H), 1.32-1.28 (m, 2H), 0.89 (t, J = 8.0 Hz, 3H). 1-1918 Cl [04025]
[04026]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.71-7.68 (m, 2H), 7.48-7.45 (m, 3H), 6.73-6.70 (m, 1H), 5.96- 5.93 (m, 1H), 5.71-5.68 (m, 1H), 4.32 (s, 3H). 1-1919 Cl [04027]
[04028]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.30 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.81-7.75 (m, 2H), 7.65-7.59 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 6.45 (t, J = 57.0 Hz, 1H), 4.32 (s, 3H). 1-1920 Cl [04029]
[04030]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.02 (s, 1H), 7.88-7.85 (m, 1H), 7.68-7.65 (m, 1H), 7.59-7.57 (m, 1H), 7.48 (d, J = 5.0 Hz, 1H), 4.99 (s, 2H), 4.33 (s, 3H). 1-1921 Cl [04031]
[04032]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.80-7.77 (m, 2H), 7.48 (d, J = 5.0 Hz, 1H), 7.04-7.01 (m, 2H), 4.38 (s, 3H), 3.99 (t, J = 7.5 Hz, 2H), 1.78-1.71 (m, 2H), 0.98 (t, J = 8.0 Hz, 3H). 1-1922 Cl [04033]
[04034]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.85-7.79 (m, 2H), 7.55-7.49 (m, 3H), 4.39 (s, 3H), 2.45 (s, 3H). 1-1923 Cl [04035]
[04036]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.68-7.65 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.21-7.17 (m, 2H), 4.38 (s, 3H). 1-1924 Cl [04037]
[04038]
1-1925 Cl [04039]
[04040]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.89-7.82 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.51-7.45 (m, 2H), 4.30 (s, 3H), 2.87 (s, 6H). 1-1926 Cl [04041]
[04042]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.73-7.70 (m, 2H), 7.53-7.50 (m, 1H), 7.16-7.14 (m, 1H), 4.31 (s, 3H), 2.27 (s, 3H), 2.23 (s, 3H). 1-1927 Cl [04043]
[04044]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.53-7.50 (m, 1H), 7.33-7.26 (m, 2H), 4.38 (s, 3H). 1-1928 Cl [04045]
[04046]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.88-7.85 (m, 1H), 7.56-7.53 (m, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.22-7.19 (m, 1H), 4.39 (s, 3H). 1-1929 Cl [04047]
[04048]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.65-7.62 (m, 2H), 7.54-7.51 (m, 1H), 7.27-7.23 (m, 1H), 4.38 (s, 3H). 1-1930 Cl [04049]
[04050]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.69-7.62 (m, 2H), 7.62-7.59 (m, 1H), 7.53 (d, J = 5.0 Hz, 1H), 4.25 (s, 3H). 1-1931 Cl [04051]
[04052]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.60-7.57 (m, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.19-7.16 (m, 1H), 7.12-7.09 (m, 1H), 4.29 (s, 3H), 2.37 (s, 3H). 1-1932 Cl [04053]
[04054]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 7.5 Hz, 1H), 7.68 (d, J = 5.0 Hz, 1H), 7.56-7.53 (m, 1H), 7.10-7.07 (m, 1H), 4.30 (s, 3H), 2.31 (s, 3H). 1-1933 Cl [04055]
[04056]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.20 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.75 (s, 1H), 7.67- 7.64 (m, 2H), 6.94 (d, J = 7.5 Hz, 1H), 4.39 (s, 3H), 3.74 (s, 3H), 2.15 (s, 3H). 1-1934 Cl [04057]
[04058]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.73 (d, J = 6.0 Hz, 1H), 8.10 (s, 1H), 8.02 (s, 1H), 7.75 (s, 1H), 7.56 (d, J = 5.0 Hz, 1H), 4.29 (s, 3H), 2.32 (s, 3H). 1-1935 Cl [04059]
[04060]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.72 (dd, J = 7.5, 2.0 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 7.5 Hz, 1H), 4.37 (s, 3H), 2.25 (s, 3H). 1-1936 Cl [04061]
[04062]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.33 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.11 (d, J = 2.0 Hz, 1H), 7.96 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H), 2.45 (s, 3H). 1-1937 Cl [04063]
[04064]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 7.5 Hz, 1H), 7.76-7.72 (m, 1H), 7.61-7.55 (m, 2H), 4.29 (s, 3H), 2.39 (s, 3H). 1-1938 Cl [04065]
[04066]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.74 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 7.5 Hz, 1H), 4.35 (s, 3H), 2.45 (s, 3H). 1-1939 Cl [04067]
[04068]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.27 (dd, J = 7.5, 2.0 Hz, 1H), 7.74 (dd, J = 7.5, 2.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.40 (dd, J = 7.5, 7.5 Hz, 1H), 4.36 (s, 3H), 2.45 (s, 3H). 1-1940 Cl [04069]
[04070]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.96-7.92 (m, 1H), 7.68-7.65 (m, 1H), 7.48-7.43 (m, 2H), 4.30 (s, 3H). 1-1941 Cl [04071]
[04072]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.91-7.87 (m, 2H), 7.65 (d, J = 5.0 Hz, 1H), 7.53-7.50 (m, 1H), 4.37 (s, 3H). 1-1942 Cl [04073]
[04074]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.31 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.20 (s, 1H), 8.06-8.03 (m, 1H), 7.66 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 4.35 (s, 3H). 1-1943 Cl [04075]
[04076]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.17-8.14 (m, 1H), 7.61-7.55 (m, 2H), 7.49 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H). 1-1944 Cl [04077]
[04078]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.88 (s, 1H), 7.74- 7.70 (m, 2H), 7.59 (s, 1H), 4.35 (s, 3H). 1-1945 Cl [04079]
[04080]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.31 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.81-7.78 (m, 1H), 7.46 (d, J = 5.0 Hz, 1H), 6.79-6.76 (m, 1H), 6.74-6.72 (m, 1H), 4.31 (s, 3H), 3.76 (s, 3H). 1-1946 Cl [04081]
[04082]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.47-7.44 (m, 2H), 7.25-7.22 (m, 2H), 4.35 (s, 3H), 3.80 (s, 3H). 1-1947 Cl [04083]
[04084]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.78-7.75 (m, 1H), 7.63 (d, J = 5.0 Hz, 1H), 6.92-6.89 (m, 1H), 6.80-6.77 (m, 1H), 4.38 (q, J = 8.0 Hz, 2H), 4.35 (s, 3H), 1.45 (t, J = 8.0 Hz, 3H). 1-1948 Cl [04085]
[04086]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.48-7.44 (m, 2H), 7.05-7.01 (m, 1H), 6.90-6.87 (m, 1H), 4.39 (s, 3H), 3.70 (d, J = 7.0 Hz, 2H), 2.01-1.92 (m, 1H), 0.95 (d, J = 7.0 Hz, 6H). 1-1949 Cl [04087]
[04088]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.94 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.48 (d, J = 7.5 Hz, 1H), 6.93 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H), 3.85 (s, 3H). 1-1950 Cl [04089]
[04090]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.67-7.63 (m, 2H), 7.55 (d, J = 7.5 Hz, 1H), 4.31 (s, 3H), 4.10 (q, J = 8.0 Hz, 2H), 1.34 (t, J = 8.0 Hz, 3H). 1-1951 Cl [04091]
[04092]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.82 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.65-7.62 (m, 1H), 7.48-7.44 (m, 2H), 7.39-7.35 (m, 2H), 7.32-7.29 (m, 2H), 5.15 (s, 2H), 4.35 (s, 3H). 1-1952 Cl [04093]
[04094]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.73-7.70 (m, 2H), 7.63 (dd, J = 7.5, 2.0 Hz, 1H), 7.22 (d, J = 7.5 Hz, 1H), 4.32 (s, 3H), 3.94 (s, 3H), 3.79 (s, 3H). 1-1953 Cl [04095]
[04096]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.31 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.43 (d, J = 2.0 Hz, 1H), 8.32 (dd, J = 7.5, 2.0 Hz, 1H), 7.81 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H). 1-1954 Cl [04097]
[04098]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.46 (s, 1H), 8.25- 8.22 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 4.39 (s, 3H). 1-1955 Cl [04099]
[04100]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.17 (d, J = 2.0 Hz, 1H), 8.04 (dd, J = 7.5, 2.0 Hz, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H). 1-1956 Cl [04101]
[04102]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 2.0 Hz, 1H), 8.05 (dd, J = 7.5, 2.0 Hz, 1H), 7.74 (d, J = 7.5 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H). 1-1957 Cl [04103]
[04104]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.25 (s, 1H), 7.98 (s, 1H), 7.92 (s, 1H), 7.69 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H). 1-1958 Cl [04105]
[04106]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.18 (dd, J = 7.5, 2.0 Hz, 1H), 8.10 (d, J = 2.0 Hz, 1H), 7.70 (d, J = 7.5 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-1959 Cl [04107]
[04108]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.32 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.78 (s, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.49 (s, 1H), 7.42 (s, 1H), 4.31 (s, 3H), 3.79 (s, 3H). 1-1960 Cl [04109]
[04110]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.01 (d, J = 2.0 Hz, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 7.15 (d, J = 7.5 Hz, 1H), 4.39 (s, 3H), 3.85 (s, 3H). 1-1961 Cl [04111]
[04112]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.19 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.44 (dd, J = 7.5, 2.0 Hz, 1H), 7.82 (dd, J = 7.5, 2.0 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.37 (dd, J = 7.5, 7.5 Hz, 1H), 4.34 (s, 3H), 3.84 (s, 3H). 1-1962 Cl [04113]
[04114]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.46 (dd, J = 7.5, 2.0 Hz, 1H), 8.34 (d, J = 2.0 Hz, 1H), 7.98 (d, J = 7.5 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H). 1-1963 Cl [04115]
[04116]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.38 (d, J = 2.0 Hz, 1H), 8.11 (dd, J = 7.5, 2.0 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.36 (d, J = 7.5 Hz, 1H), 4.34 (s, 3H). 1-1964 Cl [04117]
[04118]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 7.94 (dd, J = 7.5, 2.0 Hz, 1H), 7.87 (d, J = 2.0 Hz, 1H), 7.76 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-1965 Cl [04119]
[04120]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 2.0 Hz, 1H), 7.89 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 7.5 Hz, 1H), 4.30 (s, 3H). 1-1966 Cl [04121]
[04122]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.16 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.28 (s, 1H), 4.35 (s, 3H), 2.37 (s, 3H). 1-1967 Cl [04123]
[04124]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 10.0 Hz, 1H), 7.74 (d, J = 6.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 2.43 (s, 3H). 1-1968 Cl [04125]
[04126]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.87 (s, 2H), 7.49 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-1969 Cl [04127]
[04128]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.64 (d, J = 5.0 Hz, 1H), 7.56-7.53 (m, 1H), 7.00-6.97 (m, 1H), 4.34 (s, 3H), 3.84 (s, 3H). 1-1970 Cl [04129]
[04130]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.68-7.61 (m, 2H), 4.35 (s, 3H). 1-1971 Cl [04131]
[04132]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.36 (s, 2H), 4.31 (s, 3H), 3.82 (s, 6H), 3.73 (s, 3H). 1-1972 Cl [04133]
[04134]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 9.25 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 7.86 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.13 (dd, J = 7.5, 2.0 Hz, 1H), 7.01-6.98 (m, 1H), 4.33 (s, 3H). 1-1973 Cl [04135]
[04136]
1-1974 Cl [04137]
[04138]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.60 (s, 1H), 7.28 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.89 (s, 3H). 1-1975 Cl [04139]
[04140]
1-1976 Cl [04141]
[04142]
1-1977 Cl [04143]
[04144]
1-1978 Cl [04145]
[04146]
1-1979 Cl [04147]
[04148]
1-1980 Cl [04149]
[04150]
1-1981 Cl [04151]
[04152]
1-1982 Cl [04153]
[04154]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 8.58 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 2.60 (s, 3H), 2.21 (s, 3H). 1-1983 Cl [04155]
[04156]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.64 (s, 2H), 4.39 (s, 3H), 2.55 (s, 6H). 1-1984 Cl [04157]
[04158]
1-1985 Cl [04159]
[04160]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.81 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.18 (s, 1H), 7.87 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 2.32 (s, 3H). 1-1986 Cl [04161]
[04162]
1-1987 Cl [04163]
[04164]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.26 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H), 2.30 (s, 3H). 1-1988 Cl [04165]
[04166]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.42 (s, 1H), 8.33 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.28 (s, 3H). 1-1989 Cl [04167]
[04168]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.30 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.62 (s, 1H), 8.25 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 2.30 (s, 3H). 1-1990 Cl [04169]
[04170]
1-1991 Cl [04171]
[04172]
1-1992 Cl [04173]
[04174]
1-1993 Cl [04175]
[04176]
1-1994 Cl [04177]
[04178]
1-1995 Cl [04179]
[04180]
1-1996 Cl [04181]
[04182]
1-1997 Cl [04183]
[04184]
1-1998 Cl [04185]
[04186]
1-1999 Cl [04187]
[04188]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 6.80 (d, J = 4.5 Hz, 1H), 6.09 (d, J = 4.5 Hz, 1H), 4.35 (s, 3H), 2.35 (s, 3H). 1-2000 Cl [04189]
[04190]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 9.25 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.67 (s, 1H), 6.88 (s, 1H), 4.33 (s, 3H). 1-2001 Cl [04191]
[04192]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 11.51 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.04 (d, J = 5.0 Hz, 1H), 7.74-7.71 (m, 2H), 7.33 (d, J = 4.5 Hz, 1H), 6.74 (s, 1H), 2.41 (s, 3H). 1-2002 Cl [04193]
[04194]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 4.5 Hz, 1H), 7.27 (d, J = 4.5 Hz, 1H), 4.33 (s, 3H), 2.31 (s, 3H). 1-2003 Cl [04195]
[04196]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.10 (s, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.68 (s, 1H), 4.33 (s, 3H). 1-2004 Cl [04197]
[04198]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.30 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 7.85 (s, 1H), 7.42 (d, J = 4.5 Hz, 1H), 7.18 (d, J = 4.5 Hz, 1H), 4.51 (s, 2H), 4.33 (s, 3H), 1.39 (s, 9H). 1-2005 Cl [04199]
[04200]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.86-7.78 (m, 2H), 7.60 (d, J = 7.5 Hz, 1H), 7.51-7.45 (m, 3H), 7.34 (d, J = 7.5 Hz, 1H), 4.36 (s, 3H). 1-2006 Cl [04201]
[04202]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 7.72 (d, J = 5.0 Hz, 1H), 7.03 (d, J = 4.5 Hz, 1H), 6.81 (d, J = 4.5 Hz, 1H), 6.35-6.31 (m, 1H), 4.36 (s, 3H). 1-2007 Cl [04203]
[04204]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 3.5 Hz, 1H), 6.69 (d, J = 3.5 Hz, 1H), 4.60-4.56 (m, 1H), 4.32 (s, 3H), 1.27 (d, J = 7.0 Hz, 6H). 1-2008 Cl [04205]
[04206]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.91 (d, J = 4.5 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 4.5 Hz, 1H), 6.58-6.53 (m, 1H), 4.30 (s, 3H). 1-2009 Cl [04207]
[04208]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 6.14 (s, 1H), 4.32 (s, 3H), 2.75 (s, 3H), 2.24 (s, 3H). 1-2010 Cl [04209]
[04210]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.67 (dd, J = 7.5, 1.5 Hz, 1H), 7.61 (dd, J = 7.5, 1.5 Hz, 1H), 7.42-7.38 (m, 1H), 7.30- 7.23 (m, 2H), 4.33 (s, 3H). 1-2011 Cl [04211]
[04212]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.58-8.56 (m, 1H), 8.49-8.47 (m, 1H), 8.10-8.07 (m, 1H), 8.05-8.02 (m, 1H), 7.83 (d, J = 5.0 Hz, 1H), 7.73-7.69 (m, 1H), 7.57-7.54 (m, 1H), 7.49-7.46 (m, 1H), 4.32 (s, 3H). 1-2012 F CH.sub.3 [04213]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.46 (d, J = 5.0 Hz, 1H), 7.50-7.47 (m, 1H), 4.33 (s, 3H), 2.54 (s, 3H). 1-2013 F [04214]
[04215]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.30 (d, J = 5.0 Hz, 1H), 7.82 (dd, J = 7.0, 5.0 Hz, 1H), 4.33 (s, 3H), 1.77-1.72 (m, 1H), 0.84-0.79 (m, 2H), 0.71-0.65 (m, 2H). 1-2014 F [04216]
[04217]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.35 (d, J = 5.0 Hz, 1H), 7.81 (dd, J = 7.0, 5.0 Hz, 1H), 4.34 (s, 3H), 3.70 (t, J = 6.0 Hz, 2H), 2.43 (t, J = 7.0 Hz, 2H), 2.09-2.02 (m, 2H). 1-2015 F [04218]
[04219]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.95-7.89 (m, 2H), 7.81 (dd, J = 7.0, 5.0 Hz, 1H), 7.51-7.45 (m, 2H), 4.37 (s, 3H). 1-2016 F [04220]
[04221]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s 1H), 8.47 (d, J = 5.0 Hz, 1H), 8.18-8.12 (m, 2H), 7.84 (dd, J = 6.0, 5.0 Hz, 1H), 7.77-7.71 (m, 2H), 4.38 (s, 3H). 1-2017 F [04222]
[04223]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 9.06 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.31 (d, J = 8.0 H,z 1H), 8.16 (d, J = 5.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 4.34 (s, 3H). 1-2018 F [04224]
[04225]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.90 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.09- 8.01 (m, 2H), 7.47 (d, J = 8.0 Hz, 1H), 4.30 (s, 3H). 1-2019 F [04226]
[04227]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.73 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.37- 8.28 (m, 2H), 8.07 (d, J = 7.0 Hz, 1H), 4.32 (s, 3H). 1-2020 F [04228]
[04229]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.22 (d, J = 5.0 Hz, 1H), 8.09 (dd, J = 7.0, 5.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-2021 F [04230]
[04231]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.33 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.14-8.10 (m, 1H), 7.90 (s, 1H), 7.00 (s, 1H), 4.35 (s, 3H), 3.93 (s, 3H). 1-2022 F [04232]
[04233]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 8.05 (dd, J = 7.0, 5.0 Hz, 1H), 7.98-7.62 (m, 2H), 7.04 (s, 1H), 4.35 (s, 3H). 1-2023 OH [04234]
[04235]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 7.89-7.86 (m, 3H), 7.35- 7.27 (m, 2H), 4.38 (s, 3H). 1-2024 OMe [04236]
[04237]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 6.86-6.82 (m, 1H), 6.17-6.13 (m 1H), 5.68-5.64 (m, 1H), 4.32 (s, 3H), 3.79 (s, 3H). 1-2025 OMe [04238]
[04239]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.43 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.83 (s, 3H), 1.78-1.74 (m, 1H), 0.84-0.77 (m, 2H), 0.72-0.65 (m, 2H). 1-2026 OMe [04240]
[04241]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.16 (d, J = 5.0 Hz, 1H), 7.88 (s, 1H), 7.03 (s, 1H), 4.32 (s, 3H), 3.93 (s, 3H), 3.82 (s, 3H). 1-2027 OMe [04242]
[04243]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.18 (d, J = 5.0 Hz, 1H), 7.62 (d, J = 4.5 Hz, 1H), 7.12 (d, J = 4.5 Hz, 1H), 4.31 (s, 3H), 3.79 (s, 3H), 2.39 (s, 3H). 1-2028 OMe [04244]
[04245]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.30 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.84-7.78 (m, 2H), 7.51-7.42 (m, 3H), 4.35 (s, 3H), 3.68 (s, 3H). 1-2029 OMe [04246]
[04247]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.17-8.10 (m, 2H), 7.87 (d, J = 5.0 Hz, 1H), 7.77-7.71 (m, 2H), 4.36 (s, 3H), 3.71 (s, 3H). 1-2030 OMe [04248]
[04249]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 9.06 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.30 (d, J = 8.0 Hz, 1H), 8.18 (d, J = 5.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 4.33 (s, 3H), 3.72 (s, 3H). 1-2031 OMe [04250]
[04251]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.79 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 8.0, Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H), 3.53 (s, 3H). 1-2032 OMe [04252]
[04253]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.30 (s, 1H), 8.72-8.63 (m, 2H), 8.32 (d, J = 8.0 Hz, 1H), 8.20 (d, J = 9.0 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H), 3.58 (s, 3H). 1-2033 OMe [04254]
[04255]
1-2034 OMe [04256]
[04257]
1-2035 OMe [04258]
[04259]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.83 (t, J = 57.0 Hz, 1H), 7.70 (s, 1H), 7.58 (d, J = 5.0 H, 1H), 6.96 (s, 1H), 4.33 (s, 3H), 2.59 (s, 3H). 1-2036 [04260]
[04261]
[04262]
1-2037 [04263]
[04264]
[04265]
1-2038 [04266]
[04267]
[04268]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.31 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 8.12 (d, J = 5.0 Hz, 1H), 6.78 (dd, J = 17.0, 10.0 Hz, 1H), 6.06 (dd, J = 14.0, 10.0 Hz, 1H), 5.95 (s, 1H), 5.58 (dd, J = 17.0, 14.0 Hz, 1H), 4.33 (s, 3H), 2.71 (s, 3H). 1-2039 [04269]
[04270]
[04271]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.92 (s, 1H), 8.51 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.24 (d, J = 5.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 5.95 (s, 1H), 4.29 (s, 3H), 2.64 (s, 3H). 1-2040 [04272]
[04273]
[04274]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.31 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.24 (d, J = 5.0 Hz, 1H), 7.75 (s, 1H), 6.87 (s, 1H), 5.95 (s, 1H), 4.38 (s, 3H), 3.92 (s, 3H), 2.72 (s, 3H). 1-2041 [04275]
CH.sub.3 [04276]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.46 (d, J = 5.0 Hz, 1H), 8.04 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.92 (s, 6H), 2.56 (s, 3H). 1-2042 [04277]
CH.sub.2CH.sub.3 [04278]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.44 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 3.13 (q, J = 8.0 Hz, 2H), 2.89 (s, 6H), 1.18 (t, J = 8.0 Hz, 3H). 1-2043 [04279]
[04280]
[04281]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 8.17 (d, J = 5.0 Hz, 1H), 6.73 (dd, J = 17.0, 10.0 Hz, 1H), 6.10 (dd, J = 14.0, 10.0 Hz, 1H), 5.60 (dd, J = 17.0, 14.0 Hz, 1H), 4.33 (s, 3H), 2.91 (s, 6H). 1-2044 [04282]
[04283]
[04284]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.44 (d, J = 5.0 Hz, 1H), 8.01 (d, J = 5.0 Hz, 1H), 7.61-7.54 (m, 2H), 7.24-7.17 (m, 2H), 4.37 (s, 3H), 2.80 (s, 6H). 1-2045 [04285]
[04286]
[04287]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.88 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.25 (d, J = 5.0 Hz, 1H), 8.15 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 4.39 (s, 3H), 2.82 (s, 6H). 1-2046 [04288]
[04289]
[04290]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.91 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.26 (d, J = 5.0 Hz, 1H), 7.48 (d, J = 7.5 Hz, 1H), 7.10 (d, J = 7.5 Hz, 1H), 4.35 (s, 3H), 2.93 (s, 6H), 2.38 (s, 3H). 1-2047 [04291]
[04292]
[04293]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.27 (d, J = 5.0 Hz, 1H), 7.70 (s, 1H), 6.82 (s, 1H), 4.33 (s, 3H), 3.92 (s, 3H), 2.95 (s, 6H). 1-2048 [04294]
[04295]
[04296]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.33 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.27 (d, J = 5.0 Hz, 1H), 7.97-7.72 (m, 2H), 6.97 (s, 1H), 4.33 (s, 3H), 2.94 (s, 6H). 1-2049 [04297]
[04298]
[04299]
1-2050 [04300]
[04301]
[04302]
1-2051 SMe [04303]
[04304]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.84-7.78 (m, 2H), 7.51-7.42 (m, 3H), 4.37 (s, 3H), 2.48 (s, 3H). 1-2052 SMe [04305]
[04306]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.11-8.04 (m, 2H), 7.77-7.71 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 2.22 (s, 3H). 1-2053 SMe [04307]
[04308]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.89-7.83 (m, 2H), 7.72-7.66 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 6.99 (s, 2H), 4.33 (s, 3H), 2.22 (s, 3H). 1-2054 SMe [04309]
[04310]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.79 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 4.34 (s, 3H), 2.53 (s, 3H). 1-2055 SMe [04311]
[04312]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.62 (s, 1H), 8.31 (d, J = 8.0 Hz, 1H), 8.22 (d, J = 6.0 Hz, 1H), 7.59 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.54 (s, 3H). 1-2056 SMe [04313]
[04314]
1-2057 SMe [04315]
[04316]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.83 (t, J = 57.0 Hz, 1H), 7.70 (s, 1H), 7.58 (d, J = 5.0 Hz, 1H), 6.96 (s, 1H), 4.34 (s, 3H), 2.59 (s, 3H). 1-2058 [04317]
CH.sub.3 [04318]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.37 (s, 3H), 2.72 (s, 3H), 2.61 (s, 3H). 1-2059 [04319]
[04320]
[04321]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.99 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 6.99 (dd, J = 17.0, 10.0 Hz, 1H), 6.10 (dd, J = 14.0, 10.0 Hz, 1H), 5.72 (dd, J = 17.0, 14.0 Hz, 1H), 4.31 (s, 3H), 2.66 (s, 3H). 1-2060 [04322]
[04323]
[04324]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 9.09 (d, J = 5.0 Hz, 1H), 7.94 (s, 1H), 7.82 (d, J = 5.0 Hz, 1H), 6.92 (s, 1H), 4.36 (s, 3H), 3.92 (s, 3H), 2.71 (s, 3H). 1-2061 Cl OMe [04325]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.60 (s, 3H). 1-2062 Cl [04326]
[04327]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.06 (d, J = 5.0 Hz, 1H), 7.22 (d, J = 5.0 Hz, 1H), 4.39 (s, 2H), 4.30 (s, 3H). 1-2063 Cl [04328]
[04329]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 8.17 (d, J = 5.0 Hz, 1H), 7.47-7.39 (m, 2H), 7.32 (d, J = 5.0 Hz, 1H), 7.18-7.11 (m, 2H), 7.00-6.96 (m, 1H), 4.35 (s, 3H). 1-2064 Cl [04330]
[04331]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 8.08 (d, J = 5.0 Hz, 1H), 7.43-7.27 (m, 5H), 7.22 (d, J = 5.0 Hz, 1H), 5.33 (s, 2H), 4.40 (s, 3H). 1-2065 Cl SMe [04332]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.20 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.60 (s, 3H). 1-2066 Cl [04333]
[04334]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.36 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.10 (t, J = 5.0 Hz, 2H), 1.68-1.64 (m, 2H), 1.02 (t, J = 8.0 Hz, 3H). 1-2067 Cl [04335]
[04336]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 8.47 (d, J = 5.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 1.35 (s, 9H). 1-2068 Cl [04337]
[04338]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.39 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.36-7.30 (m, 3H), 7.28-7.21 (m, 2H), 4.55 (s, 2H), 4.33 (s, 3H). 1-2069 Cl [04339]
[04340]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.48 (d, J = 5.0 Hz, 1H), 7.66 (d, J = 5.0 Hz, 1H), 7.17 (d, J = 7.0 Hz, 2H), 7.12-7.06 (m, 2H), 4.53 (s, 2H), 4.39 (s, 3H), 3.51 (s, 3H). 1-2070 Cl [04341]
[04342]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.00 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H), 2.83 (t, J = 5.0 Hz, 1H), 2.55 (t, J = 5.0 Hz, 1H), 1.47-1.42 (m, 2H), 0.93 (t, J = 8.0 Hz, 3H). 1-2071 Cl [04343]
[04344]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 8.16 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.13 (t, J = 8.0 Hz, 2H), 1.56- 1.48 (m, 2H), 0.90 (t, J = 8.0 Hz, 3H). 1-2072 Cl NH.sub.2 [04345]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.31 (s, 1H), 8.39 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 5.0 Hz, 1H), 6.30 (s, 2H), 4.33 (s, 3H). 1-2073 Cl [04346]
[04347]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 9.25 (s, 1H), 8.42 (d, J = 5.0 Hz, 1H), 7.44 (d, J = 5.0 Hz, 1H), 4.37 (s, 3H), 3.04 (s, 3H). 1-2074 Cl [04348]
[04349]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.34 (d, J = 5.0 Hz, 1H), 7.40 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.19 (s, 6H). 1-2075 Cl [04350]
[04351]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.31 (s, 1H), 10.22 (s, 1H), 8.41 (d, J = 5.0 Hz, 1H), 7.78- 7.72 (m, 2H), 7.42 (d, J = 5.0 Hz, 1H), 7.33-7.28 (m, 2H), 7.02-6.99 (m, 1H), 4.33 (s, 3H). 1-2076 Cl [04352]
[04353]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.99 (s, 1H), 8.37 (d, J = 5.0 Hz, 1H), 7.35 (d, J = 5.0 Hz, 1H), 7.21-7.15 (m, 2H), 6.92-6.86 (m, 2H), 4.62 (s, 2H), 4.30 (s, 3H), 3.79 (s, 3H). 1-2077 F OMe [04354]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H), 3.55 (s, 3H). 1-2078 F [04355]
[04356]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 8.15 (dd, J = 8.0, 5.0 Hz, 1H), 4.33 (s, 3H), 2.81 (t, J = 5.0 Hz, 1H), 2.54 (t, J = 5.0 Hz, 1H), 1.47-1.41 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H). 1-2079 OMe OMe [04357]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 3.62 (s, 3H), 3.45 (s, 3H). 1-2080 OMe [04358]
[04359]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.39 (s, 3H), 2.81 (t, J = 5.0 Hz, 1H), 2.54 (t, J = 5.0 Hz, 1H), 1.47-1.41 (m, 2H), 0.93 (t, J = 8.0 Hz, 3H). 1-2081 OMe NH.sub.2 [04360]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.27 (s, 1H), 8.23 (d, J = 5.0 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.21 (s, 2H), 3.81 (s, 3H). 1-2082 SMe OMe [04361]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.24 (s, 1H), 8.02 (d, J = 5.0 Hz, 1H), 7.28 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.92 (s, 3H), 2.31 (s, 3H). 1-2083 SMe SMe [04362]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.62 (s, 3H), 2.20 (s, 3H). 1-2084 SMe [04363]
[04364]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.33 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.85 (t, J = 5.0 Hz, 1H), 2.55 (t, J = 5.0 Hz, 1H), 2.39 (s, 3H), 1.46-1.40 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H). 1-2085 [04365]
OMe [04366]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.29 (s, 1H), 8.28 (d, J = 5.0 Hz, 1H), 7.14 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 3.92 (s, 3H), 2.86 (s, 3H). 1-2086 [04367]
OMe [04368]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.23 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.34 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.95 (s, 3H), 3.24 (s, 3H). 1-2087 NH.sub.2 [04369]
[04370]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.20 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 5.83 (s, 2H), 4.33 (s, 3H), 2.76 (t, J = 8.0 Hz, 1H), 2.53 (t, J = 8.0 Hz, 1H), 1.47-1.42 (m, 2H), 0.88 (t, J = 8.0 Hz, 3H). 1-2088 [04371]
[04372]
[04373]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.21 (s, 1H), 7.98 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 6.58 (s, 1H), 5.95 (s, 1H), 4.30 (s, 3H), 2.73 (s, 3H), 2.68 (s, 3H). 1-2089 [04374]
OMe [04375]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.35 (s, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H), 3.83 (s, 3H), 2.91 (s, 6H). 1-2090 [04376]
[04377]
[04378]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.26 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 8.28 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.93 (s, 6H), 2.82 (t, J = 5.0 Hz, 1H), 2.54 (t, J = 5.0 Hz, 1H), 1.47-1.41 (m, 2H), 0.92 (t, J = 7.9 Hz, 3H). 1-2091 [04379]
[04380]
[04381]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.33 (s, 1H), 8.09 (d, J = 5.0 Hz, 1H), 7.19 (d, J = 5.0 Hz, 1H), 6.50 (s, 1H), 4.36 (s, 3H), 2.81 (s, 6H), 2.73 (s, 3H). 1-2092 [04382]
[04383]
[04384]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.28 (s, 1H), 8.19 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 3.18 (s, 6H), 2.93 (s, 6H). 1-2093 [04385]
[04386]
[04387]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.31 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.38-7.32 (m, 2H), 6.92-6.86 (m, 2H), 6.22 (s, 1H), 4.34-4.31 (m, 5H), 3.79 (s, 3H), 2.75 (t, J = 5.0 Hz, 1H), 2.55 (t, J = 5.0 Hz, 1H), 1.50-1.44 (m, 2H), 0.95 (t, J = 8.0 Hz, 3H). 1-2094 [04388]
OMe [04389]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.25 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 6.69-6.64 (m, 1H), 5.74-5.70 (m, 1H), 5.46-5.42 (m, 1H), 4.33 (s, 3H), 3.63 (s, 3H). 1-2095 [04390]
OMe [04391]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.31 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.56 (d, J = 5.0 Hz, 1H), 7.23-7.13 (m, 4H), 4.33 (s, 3H), 3.80 (s, 3H). 1-2096 [04392]
[04393]
[04394]
1-2097 [04395]
[04396]
[04397]
.sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.22 (s, 1H), 8.60 (d, J = 5.0 Hz, 1H), 8.23 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.85 (t, J = 8.0 Hz, 1H), 2.65 (t, J = 8.0 Hz, 1H), 2.48 (s, 3H), 2.40 (s, 3H) 1.47-1.41 (m, 2H), 0.91 (t, J = 8.0 Hz, 3H).
[0177] The method for preparing the compound of the invention will be explained in detail in the following program and embodiment. The material is commercial available or prepared through known method reported in the literature or shown in the route. Those skilled in the art should understand that the compound of the invention can also be synthesized by other synthetic route. Although the detailed material and reaction condition in the synthetic route have been explicated in the following text, it is still easy to be replaced by other similar material and condition. Isomer of the compound, for example, that produced with the variation of the preparation method of the present invention is included in the scope of the present invention. In addition, the following preparation method can be further modified according to the disclosures of the present invention by using common chemical method known to those skilled in the art, for example, protection of suitable group in the process of the reaction, etc.
[0178] The following method of application can be used to improve further understanding of the preparation method of the present invention. The specific material, class and condition have been determined to be further explication of the present invention, not to be any limit of the reasonable scope thereof. Reagents of the following synthetic compound showed in the table can either be purchased from the market or easily prepared by those skilled in the art.
[0179] Examples of representative compounds are as follows, the synthetic methods of other compounds are similar, and will not be described in detail here.
[0180] 1. Synthesis of Compound 1-1
[0181] (1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a, 3.0 equivalents of sodium hydroxide, and 1.2 equivalents of 1-1-1 were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 120° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 1-2 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product 1-1-2 was obtained by reverse-phase purification with yield of 78%.
##STR04398##
[0182] (2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-1-2 was charged at room temperature. After dissolved with dichloromethane (10V), 1.1 equivalent of N,N′-carbonyldiimidazole (CDI) was added, and reacted at 30-40° C. for 1 hour under stirring. After stirring, 1.2 equivalent of b and 1.0 equivalent of 1,8-diazabicycloundec-7-ene (DBU) were added, and continued to react at 30-40° C. for 16-24 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added to the reaction system, stirred, extracted, and the organic phase was poured into the waste liquid. The water phase was adjusted to pH 5-6 with 2M hydrochloric acid solution, and a large amount of solid was precipitated out at this time. After stirring for 15-30 minutes, the solid was filtered to obtain the product, and the product was dried to remove water with yield of about 72%.
##STR04399##
[0183] 2. Synthesis of Compound 1-17
[0184] It can be prepared by referring to the above method for preparing compound 1-1; or it can be prepared by the following method:
[0185] (1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a was charged at room temperature. After dissolved with dichloromethane (10V), 1.1 equivalent of N,N′-carbonyldiimidazole (CDI) was added, and reacted at 30-40° C. for 1 hour under stirring. After stirring, 1.2 equivalent of b and 1.0 equivalent of 1,8-diazabicycloundec-7-ene (DBU) were added, and continued to react at 30-40° C. for 16-24 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added to the reaction system, stirred, extracted, and the organic phase was poured into the waste liquid. The water phase was adjusted to pH 5-6 with 2M hydrochloric acid solution, and a large amount of solid was precipitated out at this time. After stirring for 15-30 minutes, the solid was filtered to obtain the product, and the product was dried to remove water with yield of about 75%,
##STR04400##
[0186] (2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-17-1, 3.0 equivalents of potassium carbonate, and 1.2 equivalents of c were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 110° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 5-6 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product was obtained by reverse-phase purification with yield of 50%.
##STR04401##
[0187] 3. Synthesis of Compounds 1-203 and 1-205
[0188] (1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-203-1 (It can be prepared by referring to the above method for preparing compound 1-17) was charged at room temperature. After dissolved with N,N-dimethylformamide (10V), 1.0 equivalent of sodium thiomethoxide aqueous solution (20% content) was added, and reacted at 50-60° C. for 6-8 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 2% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, and adjusted to pH 5-6 with 2M hydrochloric acid solution, and the solid was precipitated out at this time, the insolubles were removed by filtration. The mother liquor was distilled under reduced pressure to remove the solvent, and the compound 1-203 was obtained by reverse-phase purification with yield of about 62%.
##STR04402##
[0189] (2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-203 was charged at room temperature. After dissolved with dichloromethane (10V), 1.0 equivalent of 1-205-1 (85% content) was added, and reacted at 10-20° C. for 15-30 minutes under stirring. The reaction solution was sampled and when the remaining raw materials were less than 1% according to LC-MS detection, the reaction was terminated. After the reaction was completed, sodium thiosulfate aqueous solution was added to quench the reaction, the insolubles were removed by filtration, distilled under reduced pressure to remove the solvent, and the compound 1-205 was obtained by reverse-phase purification with yield of about 50%.
##STR04403##
[0190] Or
##STR04404##
can be prepared from
##STR04405##
by referring to the above preparation method, then
##STR04406##
can be prepared, and reacts with
##STR04407##
respectively to obtain compound 1-203 and compound 1-205 by referring to the synthesis step (2) of the above compound 1-1.
[0191] 4. Synthesis of Compound 1-223
[0192] (1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a, 3.0 equivalents of sodium hydroxide, and 2.5 equivalents of c were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 120° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 1-2 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product 1-223-1 was obtained by reverse-phase purification with yield of 45%.
##STR04408##
[0193] (2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-223-1 was charged at 10-20° C. After dissolved with pyridine (10V), 10% 4-dimethylaminopyridine (DMAP) and 1.2 equivalents of compound b were charged sequentially, and 3.0 equivalents of thionyl chloride was added in a dropwise manner at 10-20° C. under stirring, then heated to 30-40° C., and reacted for 2 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, the pyridine was removed by distillation under reduced pressure, dissolved with 10V water, adjusted to pH 2-3 with 1M hydrochloric acid, then extracted three times with dichloromethane (5V). The organic phases were combined and distilled under reduced pressure to remove the solvent. The product 1-223 was obtained by reverse-phase purification with yield of about 52%.
##STR04409##
[0194] 5. Synthesis of Compound 1-249
[0195] It can be prepared by referring to the above method for preparing compound 1-1; or it can be prepared by the following method:
[0196] To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-17-1, 3.0 equivalents of potassium carbonate, and 1.2 equivalents of 1-249-1 were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 110° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 5-6 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product was obtained by reverse-phase purification with yield of 50%.
##STR04410##
[0197] 6. Synthesis of Compound 1-962
[0198] (1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a, 3.0 equivalents of potassium carbonate, and 1.1 equivalents of c were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 120° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 1% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, extracted two times with ethyl acetate (5V), and the water phases were adjusted to pH 2-3 with 2M hydrochloric acid solution, then the solid was precipitated out, filtered and dried to obtain the product 1-962-1 with yield of 82%.
##STR04411##
[0199] (2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-962-1 was charged at room temperature. After dissolved with dichloromethane (10V), 1.1 equivalent of N,N′-carbonyldiimidazole (CDI) was added, and reacted at 30-40° C. for 1 hour under stirring. After stirring, 1.2 equivalent of d and 1.0 equivalent of 1,8-diazabicycloundec-7-ene (DBU) were added, and continued to react at 30-40° C. for 5-8 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added to the reaction system, stirred, extracted, and the organic phase was poured into the waste liquid. The water phase was adjusted to pH 5-6 with 2M hydrochloric acid solution, and a large amount of solid was precipitated out at this time. After stirring for 15-30 minutes, the solid was filtered to obtain the product, and the product was dried to remove water with yield of about 69%.
##STR04412##
[0200] Biological Activity Evaluation:
[0201] The activity level criteria for plant damage (i.e., growth control rate) are as follows:
[0202] Level 5: growth control rate is above 85%;
[0203] Level 4: growth control rate is greater than or equal to 60% and less than 85%;
[0204] Level 3: growth control rate is greater than or equal to 40% and less than 60%;
[0205] Level 2: growth control rate is greater than or equal to 20% and less than 40%;
[0206] Level 1: growth control rate is greater than or equal to 5% and less than 20%;
[0207] Level 0: growth control rate is less than 5%.
[0208] The above growth control rates are fresh weight control rates.
[0209] Experiment on weeding effect in post-emergence stage: monocotyledonous and dicotyledonous weed seeds and major crop seeds (wheat, corn, rice, soybean, cotton, oilseed rape, millet, sorghum) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil, allowed to grow in a good greenhouse environment. After 2 weeks of sowing, the test plants were treated in the 2-3 leaf stage. The tested compounds of the present invention were respectively dissolved in acetone at the dosage of 2000, 1000, 500, 250, 125 g/ha, then added with Tween 80 and 1.5 liter/ha of emulsifiable concentrate of methyl oleate as synergist, diluted with a certain amount of water to obtain a solution with a certain concentration, and sprayed with a spray tower onto the plants. After the application, the plants were cultured for 3 weeks in the greenhouse, and then the experimental results were listed in Table 1.
TABLE-US-00002 TABLE 1 Results on weeding effect in post-emergence stage Com- Descurainia Abutilon Amaranthus Chenopodium pound No. sophia theophrasti retroflexus L. album 1-1 5 5 5 5 1-2 5 5 5 5 1-3 5 5 5 5 1-4 5 5 5 5 1-5 5 5 5 5 1-6 5 5 5 5 1-7 5 5 5 5 1-8 5 5 5 5 1-9 5 5 5 5 1-10 5 5 5 5 1-11 5 5 5 5 1-12 5 5 5 5 1-13 5 5 5 5 1-14 5 5 5 5 1-15 5 5 5 5 1-16 5 5 5 5 1-17 5 5 5 5 1-18 5 5 5 5 1-19 5 5 5 5 1-20 5 5 5 5 1-21 5 5 5 5 1-22 5 5 5 5 1-23 5 5 5 5 1-24 5 5 5 5 1-25 5 5 5 5 1-26 5 5 5 5 1-27 5 5 5 5 1-28 5 5 5 5 1-29 5 5 5 5 1-30 5 5 5 5 1-31 5 5 5 5 1-32 5 5 5 5 1-33 5 5 5 5 1-34 5 5 5 5 1-35 5 5 5 5 1-36 5 5 5 5 1-37 5 5 5 5 1-38 5 5 5 5 1-39 5 5 5 5 1-40 5 5 5 5 1-41 5 5 5 5 1-42 5 5 5 5 1-43 5 5 5 5 1-44 5 5 5 5 1-45 5 5 5 5 1-46 5 5 5 5 1-47 5 5 5 5 1-48 5 5 5 5 1-49 5 5 5 5 1-50 5 5 5 5 1-51 5 5 5 5 1-52 5 5 5 5 1-53 5 5 5 5 1-54 5 5 5 5 1-55 5 5 5 5 1-56 5 5 5 5 1-57 5 5 5 5 1-58 5 5 5 5 1-59 5 5 5 5 1-60 5 5 5 5 1-61 5 5 5 5 1-62 5 5 5 5 1-63 5 5 5 5 1-64 5 5 5 5 1-65 5 5 5 5 1-66 5 5 5 5 1-67 5 5 5 5 1-68 5 5 5 5 1-69 5 5 5 5 1-70 5 5 5 5 1-71 5 5 5 5 1-72 5 5 5 5 1-73 5 5 5 5 1-74 5 5 5 5 1-75 5 5 5 5 1-76 5 5 5 5 1-77 5 5 5 5 1-78 5 5 5 5 1-79 5 5 5 5 1-80 5 5 5 5 1-81 5 5 5 5 1-82 5 5 5 5 1-83 5 5 5 5 1-84 5 5 5 5 1-85 5 5 5 5 1-86 5 5 5 5 1-87 5 5 5 5 1-88 5 5 5 5 1-89 5 5 5 5 1-90 5 5 5 5 1-91 5 5 5 5 1-92 5 5 5 5 1-93 5 5 5 5 1-94 5 5 5 5 1-95 5 5 5 5 1-96 5 5 5 5 1-97 5 5 5 5 1-98 5 5 5 5 1-99 5 5 5 5 1-100 5 5 5 5 1-101 5 5 5 5 1-102 5 5 5 5 1-103 5 5 5 5 1-104 5 5 5 5 1-105 5 5 5 5 1-106 5 5 5 5 1-107 5 5 5 5 1-108 5 5 5 5 1-109 5 5 5 5 1-110 5 5 5 5 1-111 5 5 5 5 1-112 5 5 5 5 1-113 5 5 5 5 1-114 5 5 5 5 1-115 5 5 5 5 1-116 5 5 5 5 1-117 5 5 5 5 1-118 5 5 5 5 1-119 5 5 5 5 1-120 5 5 5 5 1-121 5 5 5 5 1-122 5 5 5 5 1-123 5 5 5 5 1-124 5 5 5 5 1-125 5 5 5 5 1-126 5 5 5 5 1-127 5 5 5 5 1-128 5 5 5 5 1-129 5 5 5 5 1-130 5 5 5 5 1-131 5 5 5 5 1-132 5 5 5 5 1-133 5 5 5 5 1-134 5 5 5 5 1-135 5 5 5 5 1-136 5 5 5 5 1-137 5 5 5 5 1-138 5 5 5 5 1-139 5 5 5 5 1-140 5 5 5 5 1-141 5 5 5 5 1-142 5 5 5 5 1-143 5 5 5 5 1-144 5 5 5 5 1-145 5 5 5 5 1-146 5 5 5 5 1-147 5 5 5 5 1-148 5 5 5 5 1-149 5 5 5 5 1-150 5 5 5 5 1-151 5 5 5 5 1-152 5 5 5 5 1-153 5 5 5 5 1-154 5 5 5 5 1-155 5 5 5 5 1-156 5 5 5 5 1-157 5 5 5 5 1-158 5 5 5 5 1-159 5 5 5 5 1-160 5 5 5 5 1-161 5 5 5 5 1-162 5 5 5 5 1-163 5 5 5 5 1-164 5 5 5 5 1-165 5 5 5 5 1-166 5 5 5 5 1-167 5 5 5 5 1-168 5 5 5 5 1-169 5 5 5 5 1-170 5 5 5 5 1-171 5 5 5 5 1-172 5 5 5 5 1-173 5 5 5 5 1-174 5 5 5 5 1-175 5 5 5 5 1-176 5 5 5 5 1-177 5 5 5 5 1-178 5 5 5 5 1-179 5 5 5 5 1-180 5 5 5 5 1-181 5 5 5 5 1-182 5 5 5 5 1-183 5 5 5 5 1-184 5 5 5 5 1-185 5 5 5 5 1-186 5 5 5 5 1-187 5 5 5 5 1-188 5 5 5 5 1-189 5 5 5 5 1-190 5 5 5 5 1-191 5 5 5 5 1-192 5 5 5 5 1-193 5 5 5 5 1-194 5 5 5 5 1-195 5 5 5 5 1-196 5 5 5 5 1-197 5 5 5 5 1-198 5 5 5 5 1-199 5 5 5 5 1-200 5 5 5 5 1-201 5 5 5 5 1-202 5 5 5 5 1-203 5 5 5 5 1-204 5 5 5 5 1-205 5 5 5 5 1-206 5 5 5 5 1-207 5 5 5 5 1-208 5 5 5 5 1-209 5 5 5 5 1-210 5 5 5 5 1-211 5 5 5 5 1-212 5 5 5 5 1-213 5 5 5 5 1-214 5 5 5 5 1-215 5 5 5 5 1-216 5 5 5 5 1-217 5 5 5 5 1-218 5 5 5 5 1-219 5 5 5 5 1-220 5 5 5 5 1-221 5 5 5 5 1-222 5 5 5 5 1-223 5 5 5 5 1-228 5 5 5 5 1-229 5 5 5 5 1-230 5 5 5 5 1-233 5 5 5 5 1-234 5 5 5 5 1-249 5 5 5 5 1-307 5 5 5 5 1-334 5 5 5 5 1-650 5 5 5 5 1-962 5 5 5 5 1-1257 5 5 5 5 1-1286 5 5 5 5 1-1577 5 5 5 5 1-1607 5 5 5 5 1-1918 5 5 5 5 1-1925 5 5 5 5 1-1972 5 5 5 5 1-2004 5 5 5 5 1-2006 5 5 5 5 1-2010 5 5 5 5 1-2016 5 5 5 5 1-2029 5 5 5 5 1-2044 5 5 5 5 1-2052 5 5 5 5 1-2053 5 5 5 5 1-2061 5 5 5 5 1-2062 5 5 5 5 1-2063 5 5 5 5 1-2064 5 5 5 5 1-2065 5 5 5 5 1-2069 5 5 5 5 1-2070 5 5 5 5 1-2071 5 5 5 5 1-2075 5 5 5 5 Note: The application dose was active ingredient 2000 g/ha.
[0210] In addition, under the active ingredient of 250 g/ha, many compounds also show good crop selectivity and excellent control effect on key weeds. For example, see Table 2:
TABLE-US-00003 TABLE 2 Test results Alopecurus Beckmannia Alopecurus Sclerochloa Descurainia No. aequalis syzigachne myosuroides dura sophia Wheat 1-15 5 5 5 5 5 0 1-17 5 5 5 5 5 0 Control 0 0 0 0 0 0 compound A
[0211] Control Compound A:
##STR04413##
[0212] Experiment on Weed Effect in Pre-Emergence Stage
[0213] Seeds of monocotyledonous and dicotyledonous weeds and main crops (e.g. wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into a plastic pot loaded with soil and covered with 0.5-2 cm soil. The test compounds of the present invention was dissolved with acetone, then added with tween 80, diluted by a certain amount of water to reach a certain concentration, and sprayed immediately after sowing. The obtained seeds were incubated for 4 weeks in the greenhouse after spraying and the test results were observed. It was observed that the herbicide mostly had excellent effect at the application rate of 2000 g a.i./ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis, Abutilon theophrasti, etc. And many compounds had good selectivity for corn, wheat, rice, soybean, oilseed rape, etc.
[0214] It is indicated from the experiment that the compounds of the present invention generally have good weed control efficacy, especially for the major cyperaceae weeds like Echinochloa crusgalli, Digitaria sanguinalis, and Setaria viridis, etc., and the major broad-leaved weeds like Abutilon theophrasti, Rorippa indica, and Bidens pilosa L., etc., which are widely occurring in corn, rice, and wheat fields, and have excellent commercial value. Above all, it is noted that they have extremely high activity to weeds, which are resistant to ALS inhibitor, like Rorippa indica, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine L., Stellaria media, Setaria viridis, Echinochloa crusgalli, Digitaria sanguinalis, Alopecurus aequalis, Beckmannia syzigachne, etc.
[0215] Transplanted rice safety evaluation and weed control effect evaluation in rice field:
[0216] Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Sagittaria trifolia, and Monochoria vaginalis were sowed and gently covered with soil, then left to stand still in greenhouse in the state of 0.5-1 cm of water storage. The tuber of Sagittaria trifolia was planted in the next day or 2 days later. It was kept at 3-4 cm of water storage thereafter. The weeds were treated by dripping the WP or SC water diluents prepared according to the common preparation method of the compounds of the present invention with pipette homogeneously to achieve specified effective amount when Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., and Monochoria vaginalis reached 0.5 leaf stage and Sagittaria trifolia reached the time point of primary leaf stage.
[0217] In addition, the rice field soil that loaded into the 1/1,000,000 ha pot was leveled to keep water storage at 3-4 cm depth. The 3 leaf stage rice (japonica rice) was transplanted at 3 cm of transplanting depth the next day. The compound of the present invention was treated by the same way after 5 days of transplantation.
[0218] The fertility condition of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Sagittaria trifolia and Monochoria vaginalis 14 days after the treatment of the compound of the invention and the fertility condition of rice 21 days after the treatment of the compound of the invention respectively with the naked eye. Evaluate the weed control effect with the above 0-5 activity standard level, many compounds show excellent activity and selectivity. Wherein, the seeds of Echinochloa crusgali, Scirpus juncoides, Bidens tripartita, Sagittaria trifolia and Monochoria vaginalis were collected from Heilongjiang Province of China. The tests indicated that the weeds were resistant to the common doses of Pyrazosulfuron-ethyl and Penoxsulam.
[0219] It could be seen from this experiment that the compound of the present invention has excellent activity against the anti-ALS weeds which is a serious challenge in the production, and could solve the increasingly serious problem of resistance.
[0220] At the same time, it is found after several tests that the compound of the present invention and its composition have good selectivity to many gramineae grass such as Zoysia japonica, bermuda grass, tall fescue, bluegrass, ryegrass and seashore paspalum etc, and is able to control many important grass weeds and broadleaf weeds. The compound also shows excellent selectivity and commercial value in the tests on wheat, corn, rice, sugarcane, soybean, cotton, oil sunflower, potato, orchards and vegetables in different herbicide application methods.