Patent ID: 6090833
Filing Date: 2000-07-18
Classification: A61P,C07D

Abstract:
A compound of the formula I ##STR9## in which Y is a direct bond, --CH.sub.2 --, or --CH.sub.2 --CH.sub.2 --;X is CH.sub.2, CH(CH.sub.3), CH(C.sub.2 H.sub.5), (C.sub.3 H.sub.7), or CH(C.sub.6 H.sub.5):R1, R1' independently of one another are selected from the group consisting of H, F, Cl, Hr, I, CF.sub.3, NO.sub.2, CN, COOH, COO(C.sub.1 -C.sub.6)alkyl, CONH, CONH(C.sub.1 -C.sub.6)alkyl, CON[(C.sub.1 -C.sub.6)alkyl].sub.2, (C.sub.1 -C.sub.6)-alkyl, (C.sub.2 -C.sub.6)-alkenyl, (C.sub.2 -C.sub.6)-alkynyl, and O--(C.sub.1 -C.sub.6)-alkyl, wherein optionally one or more of the hydrogens in the alkyl radicals is replaced by an alternative substituent selected from the group consisting of F, OH, OC(O)CH.sub.3, OC(O)H, OCH.sub.2 Ph, NH.sub.2, NH--CO--CH.sub.3 or N(COOCH.sub.2 Ph).sub.2 ; SO.sub.2 --NH.sub.2, SO.sub.2 NH(C.sub.1 -C.sub.6)-alkyl, SO.sub.2 N[(C.sub.1 -C.sub.6)-alkyl].sub.2, S--(C.sub.1 -C.sub.6)-alkyl, S--(CH.sub.2).sub.n -phenyl, SO--(C.sub.1 -C.sub.6)-alkyl, SO--(CH.sub.2).sub.n -phenyl, SO.sub.2 --(C.sub.1 -C.sub.6)-alkyl, and SO.sub.2 --(CH.sub.2).sub.n -phenyl, wherein n is 0-6 and the phenyl radical is optionally substituted up to two times by a substituent selected from the group consisting of F, Cl, Br, OH, CF.sub.3, NO.sub.2, CN, OCF.sub.3, O--(C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkyl, NH.sub.2 ; NH.sub.2, NH--(C.sub.1 -C.sub.6) alkyl, N((C.sub.1 -C.sub.6)-alkyl).sub.2, NH(C.sub.1 -C.sub.7)-acyl, phenyl, biphenyl, and O--(CH.sub.2).sub.n phenyl, wherein n is 0-6, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2 or 3-furanyl or 2- or 3-thienyl, and wherein the phenyl, biphenyl, naphthyl, pyridyl, furanyl or thienyl rings each is optionally substituted one to 3 times by an alternative substituent selected from the group consisting of F, Cl, Br, I, OH, CF.sub.3, NO.sub.2, CN, OCF.sub.3, O--(C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkyl, NH.sub.2, NH(C.sub.1 C.sub.6) alkyl, N((C.sub.1 -C.sub.6)-alkyl).sub.2, SO.sub.2 --CH.sub.3, COOH, COO--(C.sub.1 -C.sub.6)-alkyl, and CONH.sub.2 ; 1,2,3 triazol-5-yl, wherein the triazole ring is optionally substituted in the 1-, 2- or 3-position by methyl or benzyl; and tetrazol-5-yl, wherein the tetrazole ring is optionally substituted in the 1- or 2-position by methyl or benzyl;R2 is H, (C.sub.1 -C.sub.6)-alkyl, (C.sub.3 -C.sub.6)-cycloalkyl, (CH.sub.2).sub.n1 -phenyl, (CH.sub.2).sub.n1 -thienyl, (CH.sub.2).sub.n1 -pyridyl, (CH.sub.3).sub.n1 -furyl, C(O)--(C.sub.1 -C.sub.6)-alkyl, (C(O)--(C.sub.3 -C.sub.6)-cycloalkyl, C(O)--(CH.sub.2).sub.n1 -phenyl, C(O)--(CH.sub.2).sub.n1 -thienyl, C(O)--(CH.sub.2).sub.n1 -pyridyl C(O)--(CH.sub.2).sub.n1 -furyl, wherein n1 is 0-5 and in which phenyl, thienyl, pyridyl, furyl each is optionally substituted up to two times by a substituent selected from the group consisting of Cl, F, CN, CF.sub.3, (C.sub.1 -C.sub.3)-alkyl, OH, and O--(C.sub.1 -C.sub.6)-alkyl;R3 is H, (C.sub.1 -C.sub.6)-alkyl, F, CN, N.sub.3, O--(C.sub.1 -C.sub.6)-alkyl, (CH.sub.2).sub.n1 -phenyl, (CH.sub.2).sub.n1 -thienyl, (CH.sub.2).sub.n1 -pyridyl, or (CH.sub.2).sub.n1 -furyl, wherein n1 is 0-5 and in which phenyl, thienyl, pyridyl, furyl each is optionally substituted up to two times by one of two substituents selected from the group consisting of Cl, F, CN, CF.sub.3, (C.sub.1 -C.sub.3)-alkyl, OH, O--(C.sub.1 -C.sub.6)-alkyl; (C.sub.2 -C.sub.6)-alkynyl, (C.sub.2 -C.sub.6)-alkenyl, C(O)OCH.sub.3, C(O)OCH.sub.2 CH.sub.3, C(O)OH, C(O)NH.sub.2, C(O)NHCH.sub.3, C(O)N(CH.sub.3).sub.2, and OC(O)CH.sub.3 ;R4 is (C.sub.1 C.sub.8) allyl, (C.sub.3 -C.sub.7)-cycloalkyl, (C.sub.2 -C.sub.6)-alkenyl, (C.sub.2 -C.sub.6)-alkynyl, or (C.sub.4 -C.sub.7)-cycloalkenyl, wherein one or more hydrogens in the alkyl radical may be replaced by F and one hydrogen in the alkyl radical may be replaced by a substituent selected from the group consisting of OH, OC(O)CH.sub.3, OC(O)H, O--CH.sub.2 --Ph (or) and O--(C.sub.1 -C.sub.4)-alkyl; (CH.sub.2).sub.n2 --NR6R7, wherein n2 is 1-6 and R6 and R7 independently of one another are selected from the group consisting of H, (C.sub.1 -C.sub.6)-alkyl, (C.sub.3 -C.sub.6)-cycloalkyl, CO--(C.sub.1 -C.sub.6)-alkyl, CHO, and CO-phenyl, or wherein-NR6R7 is a ring; (CH.sub.2).sub.n -aryl, wherein n is 0-6 and aryl is selected from the group consisting of phenyl, biphenyl, 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 2-, 4- or 5-thiazolyl, 2-, 4- or 5-oxazolyl, 1-pyrazolyl, 3- or 5-isoazolyl, 2- or 3-pyrrolyl, 2- or 3-pyridazinyl, 2-, 4- or 3-pyrimidinyl, 2-pyrazinyl, 2-(1,3,5-triazinyl), 2- or 5-benzimidazolyl, 2-benzothiazolyl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, tetrazol-5-yl, indol-3-yl, indol-5-yl and N-methyl-imidazol-2-, -4- or -5-yl and the aryl radical or heteroaryl radical is optionally substituted up to two times by a substituent selected from the group consisting of F, Cl, Br, OH, CF.sub.3, NO.sub.2, CN, OCF.sub.3, O--(C.sub.1 -C.sub.6)-alkyl, S--(C.sub.1 -C.sub.6)-alkyl, SO--(C.sub.1 -C.sub.6)-alkyl, SO.sub.2 --(C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.6)-alkyl, (C.sub.3 -C.sub.6)-cycloalkyl, COOH, COO(C.sub.1 -C.sub.6)alkyl, COO(C.sub.3 -C.sub.6)cycloalkyl, CONH.sub.2, CONH(C.sub.1 C.sub.6)alkyl, CON[(C.sub.1 -C.sub.6)alkyl].sub.2, CONH(C.sub.3 -C.sub.6) cyclo-alkyl, NH.sub.2, NH--CO--(C.sub.1 -C.sub.6)-alkyl, NH--CO-phenyl, pyrrolidin-1-yl, morpholin-1-yl, piperidin-1-yl, piperazin 1 yl, 4-methylpiperazin-1-yl, (CH.sub.2).sub.n3 -phenyl, O--(CH.sub.2).sub.n3 -phenyl, S-(CH.sub.2).sub.n3 -phenyl, and SO.sub.2 --(CH.sub.2).sub.n3 -phenyl, wherein n3 =0-3,or a physiologically tolerable salt of the compound.