Patent ID: 6303593
Filing Date: 2001-10-16
Classification: C07D

Abstract:
A compound of the formula I: ##STR411##wherein:R.sup.1 is --X--R.sup.8, wherein X is selected from the group consisting of:(1) --CH.sub.2 --,(2) --CO--,(3) --CH.sub.2 CH.sub.2 --,(4) --CH.sub.2 CH.sub.2 CH.sub.2 --, and(5) --CH(C.sub.1-6 alkyl)-,and wherein R.sup.8 is a selected from:phenyl, naphthyl, biphenyl, fluorenyl, indenyl, indanyl, dihydronaphthyl, tetrahydronaphthyl, octahydronaphthyl, adamantyl, and heterocycle, which may be unsubstituted or substituted, where the substituents are independently selected from:(a) C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, wherein the alkyl, alkenyl, or alkynyl is unsubstituted or substituted, wherein the substituents are independently selected from:(i) hydroxy,(ii) halogen,(iii) --NR.sup.9 R.sup.10, wherein R.sup.9 and R.sup.10 are independently selected from hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, and C.sub.2-6 alkynyl, wherein the alkyl, alkenyl, or alkynyl is unsubstituted or substituted, wherein the substituents are independently selected from:(A) phenyl, unsubstituted or substituted, wherein the substituents are independently selected from: halogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CO.sub.2 (C.sub.1-6 alkyl), --NH.sub.2, --NH(C.sub.1-6 alkyl), --N(C.sub.1-6 alkyl)(C.sub.1-6 alkyl), or trifluoromethyl,(B) naphthyl, unsubstituted or substituted, wherein the substituents are independently selected from: halogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CO.sub.2 (C.sub.1-6 alkyl), --NH.sub.2, --NH(C.sub.1-6 alkyl), --N(C.sub.1-6 alkyl)(C.sub.1-6 alkyl), or trifluoromethyl,(C) heterocycle, unsubstituted or substituted, wherein the substituents are independently selected from: halogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CO.sub.2 (C.sub.1-6 alkyl), --NH.sub.2, --NH(C.sub.1-6 alkyl), --N(C.sub.1-6 alkyl)(C.sub.1-6 alkyl), or trifluoromethyl,(D) hydroxy,(E) --O(C.sub.1-6 alkyl),(F) --CO.sub.2 (C.sub.1-6 alkyl),(G) --S(O).sub.n --(C.sub.1-6 alkyl), wherein n is an integer selected from 0, 1 and 2,(H) halogen,(I) --NH.sub.2,(J) --NH(C.sub.1-6 alkyl), and(K) --N(C.sub.1-6 alkyl)(C.sub.1-6 alkyl),(iv) --NR.sup.9 --COR.sup.10,(v) --NR.sup.9 --CO.sub.2 R.sup.10,(vi) --CO--NR.sup.9 R.sup.10,(vii) --OCO--NR.sup.9 R.sup.10,(viii) --NR.sup.9 CO--NR.sup.9 R.sup.10,(ix) --S(O).sub.2 --NR.sup.9 R.sup.10, wherein n is an integer selected from 0, 1 and 2,(x) --NR.sup.9 S(O).sub.2 --R.sup.10,(xi) --NR.sup.9 S(O).sub.2 --NR.sup.9 R.sup.10,(xii) --S(O).sub.n --R.sup.9,(xiii) --CF.sub.3,(xiv) --CHF.sub.2,(xv) --CH.sub.2 F,(xvi) --O--R.sup.9,(xvii) --O(C.sub.1-6 alkyl)-O--R.sup.9,(xviii) phenyl,(xix) naphthyl,(xx) indenyl,(xxi) indanyl,(xxii) heterocycle,(xxiii) --CO-phenyl,(xxiv) --CO-naphthyl,(xxv) --CO-indenyl,(xxvi) --CO-indanyl,(xxvii) --CO-heterocycle,(xxviii) --OCO--R.sup.9,(xxix) --OCO.sub.2 --R.sup.9, and(xxx) --CO--R.sup.9,(b) --O--C.sub.1-6 alkyl, --O--C.sub.2-6 alkenyl, --O--C.sub.2-6 alkynyl, wherein the alkyl, alkenyl, or alkynyl is unsubstituted or substituted, wherein the substituents are independently selected from:(i) hydroxy,(ii) halogen,(iii) --NR.sup.9 R.sup.10,(iv) --NR.sup.9 --COR.sup.10,(v) --NR.sup.9 --CO.sub.2 R.sup.10,(vi) --CO--NR.sup.9 R.sup.10,(vii) --OCO--NR.sup.9 R.sup.10,(viii) --NR.sup.9 CO--NR.sup.9 R.sup.10,(ix) --S(O).sub.2 --NR.sup.9 R.sup.10,(x) --NR.sup.9 S(O).sub.2 --R.sup.10,(xi) --NR.sup.9 S(O).sub.2 --NR.sup.9 R.sup.10,(xii) --S(O).sub.n --R.sup.9,(xiii) --CF.sub.3,(xiv) --CHF.sub.2,(xv) --CH.sub.2 F,(xvii) --O--R.sup.9,(xvii) --O(C.sub.1-6 alkyl)-O--R.sup.9,(xviii) phenyl,(xix) naphthyl,(xx) indenyl,(xxi) indanyl,(xxii) heterocycle,(xxiii) --CO-phenyl,(xxiv) --CO-naphthyl,(xxv) --CO-indenyl,(xxvi) --CO-indanyl,(xxvii) --CO-heterocycle,(xxviii) --OCO--R.sup.9,(xxix) --OCO.sub.2 --R.sup.9, and(xxx) --CO--R.sup.9,(c) --NO.sub.2,(d) hydroxy,(e) halogen,(f) --NR.sup.9 R.sup.10,(g) --NR.sup.9 --COR.sup.10,(h) --NR.sup.9 --CO.sub.2 R.sup.10,(i) --CO--NR.sup.9 R.sup.10,(j) --OCO--NR.sup.9 R.sup.10,(k) --NR.sup.9 CO--NR.sup.9 R.sup.10,(l) --S(O).sub.2 --NR.sup.9 R.sup.10,(m) --NR.sup.9 S(O).sub.2 --R.sup.10,(n) --NR.sup.9 S(O).sub.2 --NR.sup.9 R.sup.10,(o) --S(O).sub.n --R.sup.9,(p) --CF.sub.3,(q) --CHF.sub.2,(r) --CH.sub.2 F,(s) --OCO--R.sup.9,(t) --OCO.sub.2 --R.sup.9, and(u) --CO--R.sup.9 ;R.sup.2 is selected from the group consisting of: ##STR412##wherein R.sup.5 is a selected from:(1) --NR.sup.6 CO--O--R.sup.7, wherein R.sup.6 is hydrogen, C.sub.1-6 alkyl or C.sub.1-6 alkyl-C.sub.5-6 cycloalkyl, and R.sup.7 is C.sub.1-6 alkyl, C.sub.5-6 cycloalkyl, benzyl or phenyl, wherein the alkyl, cycloalkyl, benzyl or phenyl is unsubstituted or substituted with halogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy or trifluoromethyl,(2) phenyl, which is unsubstituted or substituted with halogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CO.sub.2 (C.sub.1-6 alkyl), --NH.sub.2, --NHR.sup.9, --NR.sup.9 R.sup.10, or trifluoromethyl,(3) -pyridyl,(4) -thienyl,(5) --C.sub.1-6 alkyl-phenyl, --C.sub.1-6 alkyl-naphthyl, --C.sub.1-6 alkyl-indenyl, --C.sub.1-6 alkyl-indanyl, and --C.sub.1-6 alkyl-heterocycle, wherein the phenyl, naphthyl, indenyl, indanyl, or heterocycle is unsubsituted or substituted with: halogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CO.sub.2 (C.sub.1-6 alkyl), --NH.sub.2, --NHR.sup.9, --NR.sup.9 R.sup.10, or trifluoromethyl; and wherein the --C.sub.1-6 alkyl is optionally substituted with oxo, hydroxy, C.sub.1-6 alkoxy, acetoxy, or halogen,(6) --O--C.sub.1-6 alkyl-phenyl, --O--C.sub.1-6 alkyl-naphthyl, --O--C.sub.1-6 alkyl-indenyl, --O--C.sub.1-6 alkyl-indanyl, and --O--C.sub.1-6 alkyl-heterocycle, wherein the phenyl, naphthyl, indenyl, indanyl, or heterocycle is unsubsituted or substituted with: halogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CO.sub.2 (C.sub.1-6 alkyl), --NH.sub.2, --NHR.sup.9, --NR.sup.9 R.sup.10, or trifluoromethyl,(7) --C.sub.1-4 alkyl-O--C.sub.1-4 alkyl-phenyl, wherein the phenyl is unsubsituted or substituted with halogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CO.sub.2 (C.sub.1-6 alkyl), --NH.sub.2, --NHR.sup.9, --NR.sup.9 R.sup.10, or trifluoromethyl, and(8) --C.sub.1-4 alkyl-S(O).sub.n --C.sub.1-4 alkyl-phenyl, wherein the phenyl is unsubsituted or substituted with halogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CO.sub.2 (C.sub.1-6 alkyl), --NH.sub.2, --NHR.sup.9, --NR.sup.9 R.sup.10, or trifluoromethyl;and wherein R.sup.11 is a selected from:(1) -hydrogen,(2) --OH,(3) --C.sub.1-6 alkyl, and(4) -halogen;R.sup.3 is thienyl or furanyl, which may be unsubstituted or substituted, where the substituents are independently selected from:(1) C.sub.1-6 alkyl, which is unsubstituted or substituted, wherein the substituents are independently selected from:(a) hydroxy,(b) halogen,(c) --NR.sup.9 R.sup.10,(d) --NR.sup.9 --COR.sup.10,(e) --NR.sup.9 --CO.sub.2 R.sup.10,(f) --CF.sub.3,(g) --CHF.sub.2,(h) --CH.sub.2 F,(i) --O--R.sup.9, and(j) phenyl,(2) --O--C.sub.1-6 alkyl, unsubstituted or substituted with a substituent which is independently selected from:(a) hydroxy,(b) halogen,(c) --NR.sup.9 R.sup.10,(d) --NR.sup.9 --COR.sup.10,(e) --NR.sup.9 --CO.sub.2 R.sup.10,(f) --CF.sub.3,(g) --CHF.sub.2,(h) --CH.sub.2 F,(i) --O--R.sup.9, and(j) phenyl,(3) hydroxy,(4) halogen,(5) --CF.sub.3,(6) --CHF.sub.2,(7) --CH.sub.2 F,(8) --O--R.sup.9, and(9) --O(C.sub.1-6 alkyl)-O--R.sup.9 ;R.sup.4c, R.sup.4d, and R.sup.4f are independently selected from the group consisting of:(1) hydrogen, and(2) C.sub.1-6 alkyl;and pharmaceutically acceptable salts thereof and individual diastereomers thereof.