Patent ID: 6262055
Filing Date: 2001-07-17
Classification: C07D

Abstract:
The compound of structural formula (I): ##STR96##and tautomers and pharmaceutically acceptable salts thereof, wherein:A is selected from:(1) thienyl,(2) thiazolyl, ##STR97##R.sup.1 is selected from:(1) --H,(2) --CH.sub.3,(3) --CF.sub.3,(4) -halo,(5) --NO.sub.2,(6) --N(R.sup.4)(R.sup.5),(7) -phenyl,(8) substituted phenyl substituted with 1 or 2 substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) phenyl,(e) --CF.sub.3,(f) --OCF.sub.3,(g) --CN,(h) hydroxy,(i) phenyloxy, and(j) substituted phenyloxy with 1, 2, or 3 substituents selected from:(i) halogen,(ii) C.sub.1-6 alkyl,(iii) --CF.sub.3, and(iv) hydroxy;(9) phenyl C.sub.1-3 alkyl-,(10) substituted phenyl C.sub.1-3 alkyl-substituted with 1 or 2 substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) phenyl,(e) --CF.sub.3,(f) --OCF.sub.3,(g) --CN,(h) hydroxy,(i) phenyloxy, and(j) substituted phenyloxy with 1, 2, or 3 substituents selected from:(i) halogen,(ii) C.sub.1-6 alkyl,(iii) --CF.sub.3, and(iv) hydroxy;(11) --C.sub.2-5 alkenyl-R.sup.3,(12) --C.sub.2-5 alkynyl-R.sup.3, and(13) --C(O)CH.sub.2 C(O)C(O)OR.sup.7 ;R.sup.2 is selected from:(1) --H,(2) --R.sup.3,(3) --C.sub.1-6 alkyl,(4) --C.sub.1-6 alkyl substituted with R.sup.3,(5) --O--R.sup.6,(6) --O--C.sub.1-6 alkyl-OR.sup.6,(7) --S(O)n--R.sup.6,(8) --C.sub.1-6 alkyl (OR.sup.6)(R.sup.4),(9) --C.sub.1-6 alkyl (OR.sup.4)(R.sup.6),(10) --C.sub.0-6 alkyl-N(R.sup.4)(R.sup.6),(11) --C.sub.1-6 alkyl S(O)n--R.sup.6,(12) --C.sub.0-6 alkyl C(O)--R.sup.6,(13) --C.sub.0-6 alkyl C(S)--R.sup.6,(14) --C.sub.0-6 alkyl NR.sup.4 C(O)--R.sup.6, and(15) --C.sub.0-6 alkyl-C(O)N(R.sup.4)(R.sup.5);each R.sup.3 is independently selected from:(1) phenyl;(2) substituted phenyl with 1, 2, or 3 substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) phenyl,(e) --CF.sub.3,(f) --OCF.sub.3,(g) --CN,(h) hydroxy,(i) phenyloxy, and(j) substituted phenyloxy with 1, 2, or 3 substituents selected from:(i) halogen,(ii) C.sub.1-6 alkyl,(iii) --CF.sub.3, and(iv) hydroxy;(3) thienyl;(4) substituted thienyl substituted on a carbon atom with one or two substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) phenyl,(e) --CF.sub.3,(f) --OCF.sub.3,(g) --CN,(h) hydroxy,(i) phenyloxy, and(j) substituted phenyloxy with 1, 2, or 3 substituents selected from:(i) halogen,(ii) C.sub.1-6 alkyl,(iii) --CF.sub.3, and(iv) hydroxy;(5) pyridyl;(6) substituted pyridyl substituted on a carbon atom with one or two substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) phenyl,(e) --CF.sub.3,(f) --OCF.sub.3,(g) --CN,(h) hydroxy,(i) phenyloxy, and(j) substituted phenyloxy with 1, 2, or 3 substituents selected from:(i) halogen,(ii) C.sub.1-6 alkyl,(iii) --CF.sub.3, and(iv) hydroxy;(7) imidazolyl;(8) substituted imidazolyl substituted on a carbon atom with one or two substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) phenyl,(e) --CF.sub.3,(f) --OCF.sub.3,(g) --CN,(h) hydroxy,(i) phenyloxy, and(j) substituted phenyloxy with 1, 2, or 3 substituents selected from:(i) halogen,(ii) C.sub.1-6 alkyl,(iii) --CF.sub.3, and(iv) hydroxy;(9) pyrrolyl;(10) substituted pyrrolyl substituted on a carbon atom with one or two substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) phenyl,(e) --CF.sub.3,(f) --OCF.sub.3,(g) --CN,(h) hydroxy,(i) phenyloxy, and(j) substituted phenyloxy with 1, 2, or 3 substituents selected from:(i) halogen,(ii) C.sub.1-6 alkyl,(iii) --CF.sub.3, and(iv) hydroxy;(11) pyrazolyl;(12) substituted pyrazolyl substituted on a carbon atom with one or two substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) phenyl,(e) --CF.sub.3,(f) --OCF.sub.3,(g) --CN,(h) hydroxy,(i) phenyloxy, and(j) substituted phenyloxy with 1, 2, or 3 substituents selected from:(i) halogen,(ii) C.sub.1-6 alkyl,(iii) --CF.sub.3, and(iv) hydroxy;(13) C.sub.3-6 cycloalkyl;(14) substituted C.sub.3-6 cycloalkyl with 1 or 2 substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) --CF.sub.3,(e) --OCF.sub.3,(f) --CN,(g) .dbd.O, and(h) hydroxy;(15) piperidinyl;(16) substituted piperidinyl substituted on a carbon atom with one or two substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) --CF.sub.3,(e) --OCF.sub.3,(f) --CN,(g) .dbd.O, and(h) hydroxy;(17) morpholinyl;(18) substituted morpholinyl substituted at a carbon or nitrogen atom with 1 or 2 substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) --CF.sub.3,(e) --OCF.sub.3,(f) --CN,(g) .dbd.O, and(h) hydroxy;(19) naphthyl,(20) substituted naphthyl with 1, 2, or 3 substituents independently selected from:(a) -halogen,(b) --C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) --CF.sub.3,(e) --OCF.sub.3,(f) --CN, and(g) -hydroxy;(21) indolyl;(22) substituted indolyl substituted on a carbon atom with one or two substituents independently selected from:(a) -halogen,(b) --C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) --CF.sub.3,(e) --OCF.sub.3,(f) --CN, and(g) -hydroxy;(23) C.sub.3-6 cycloalkyl fused with a phenyl ring(24) substituted C.sub.3-6 cycloalkyl fused with a phenyl ring substituted on a carbon atom with one or two substituents independently selected from:(a) halogen,(b) C.sub.1-6 alkyl,(c) C.sub.1-6 alkyloxy-,(d) --CF.sub.3,(e) --OCF.sub.3,(f) --CN,(g) .dbd.O, and(h) hydroxy;each R.sup.4 is independently selected from:(1) --H,(2) --C.sub.1-3 alkyl,(3) --CF.sub.3,(4) --R.sup.3,(5) --C.sub.2-3 alkenyl,(6) --C.sub.1-3 alkyl-R.sup.3,(7) --C.sub.2-3 alkenyl-R.sup.3,(8) --S(O).sub.n --R.sup.3, and(9) --C(O)--R.sup.3 ;each R.sup.5 is independently selected from:(1) --H,(2) --C.sub.1-3 alkyl,(3) --CF.sub.3,(4) --R.sup.3,(5) --C.sub.2-3 alkenyl,(6) --C.sub.1-3 alkyl-R.sup.3,(7) --C.sub.1-3 alkenyl-R.sup.3,(8) --S(O).sub.n --R.sup.3, and(9) --C(O)--R.sup.3 ;each R.sup.6 is independently selected from:(1) --C.sub.1-3 alkyl-R.sup.3, and(2) --R.sup.3 ;R.sup.7 is H;R.sup.8 is selected from hydrogen, methyl and methoxy;each n is independently selected from 0, 1 and 2, andeach m is independently selected from 0, 1, and 2;and provided that(A) when A is thienyl or thiazolyl and R.sup.2 is --H or --C.sub.1-6 alkyl, then R.sup.1 is not(1) --H,(2) --CH.sub.3, or(7) -phenyl;(B) when A is thienyl or thiazolyl and R.sup.2 is --R.sup.3 wherein R.sup.3 is unsubstituted phenyl, then R.sup.1 is not(1) --H or(2) --CH.sub.3 ;(C) when A is thienyl and R.sup.2 is --H or --C.sub.1-6 alkyl, then R.sup.1 is not(4) -halo,(5) --NO.sub.2, or(6) --N(R.sup.4)(R.sup.5) when R.sup.4 and R.sup.5 are both --H; and(D) when A is thienyl and R.sup.2 is --R.sup.3 wherein R.sup.3 is (7) imidiazolyl or (17) morpholinyl, then R.sup.1 is not(1) --H,(2) --CH.sub.3,(4) -halo,(5) --NO.sub.2, or(6) --N(R.sup.4)(R.sup.5) when R.sup.4 and R.sup.5 are both --H.