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US 6,187,801 B1Granted
Polycyclic thiazole systems, processes for their preparation and pharmaceuticals comprising these compounds
AssigneeAventis Pharma Deutschland GmbH
InventorsGerhard Jähne, Karl Geisen, Hans-Jochen Lang, Martin Bickel
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Abstract
The invention relates to polycyclic thiazole systems and their physiologically tolerated salts and physiologically functional derivatives. Compounds of the formula I, in which the radicals have the stated meanings, and their physiologically tolerated salts and processes for their preparation are described. The compounds are suitable, for example, as anorectics.
Claims24
A compound of formula I
- in which
- Y is CH2or CH2—CH2;
- X is a direct linkage, CH2, O or S;
- R1 is F, Cl, Br, I, CF3, CN, COOH, COO(C1-C6)alkyl, CONH2, CONH(C1-C6)alkyl, CON[(C1-C6)alkyl]2, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, OCF3, O—(C2-C6)-alkyl (where one, more than one or all hydrogen(s) in the alkyl, alkenyl and alkynyl radicals may be replaced by fluorine, or one hydrogen may be replaced by OH, CN, OC(O)CH3, OC(O)H, O—CH2—Ph, NH2, NH—CO—CH3or N(COOCH2Ph)2), SO2—NH2, SO2NH(C1-C6)-alkyl, SO2N[(C1-C6)-alkyl]2, S—(C1-C6)-alkyl, S—(CH2)n-phenyl, SO2—(C1-C6)-alkyl, SO—(CH)2-phenyl, SO2-(CH2)n-phenyl (where n is 0-6 and the phenyl radical may be substituted up to two times by F, Cl, Br, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2), NH2, NH—(C1-C6)-alkyl, N((C1-C6)-alkyl)2, NH(C1-C7)-acyl, phenyl, biphenylyl, O—(CH2)n-phenyl (where n is 0-6), 1- or 2-naphthyl, 2-, 3- or 4-pyridyl, 2- or 3-furanyl, 2- or 3-thienyl (wherein the phenyl, biphenylyl, naphthyl, pyridyl, furanyl or thienyl rings may be optionally substituted up to 3 times by F, Cl, Br, I, OH, CF3, N02, CN, OCF3, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2—CH3, COOH, COO—(C1-C6)-alkyl, CONH2), 1,2,3-triazol-5-yl (wherein the triazole ring may be optionally substituted in position 1, 2 or 3 by methyl or benzyl), tetrazol-5-yl (wherein the tetrazole ring may be optionally substituted in position 1 or 2 by methyl or benzyl);
- R1′ is H or R1;
- R2 is (C1-C8)-alkyl, (C3-C7)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, C(CN)═C(CH3)2, C(O)OCH2CH3, CH2—O—C(O)—C(CH3)3, (C4-C7)-cycloalkenyl (where one, more than one or all hydrogen(s) in the alkyl, alkenyl, alkynyl radicals may be replaced by fluorine, or one hydrogen may be replaced by OH, CN, or O—(C1-C4)-alkyl), (CH2)n—NR6R7 (where n is 1-6 and R6 and R7 are independently H, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, CO—(C1-C6)-alkyl, CHO or CO-phenyl, or —NR6R7 is a ring selected from the group consisting of pyrrolidine, piperidine, morpholine, piperazine, 4-methylpiperazin-1-yl, 4-benzylpiperazin-1-yl, and phthalimidyl), or (CH2)n-aryl (where n is 0-6 and aryl is selected from the group consisting of phenyl, biphenylyl, 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-isoxazolyl, 2-or 3-pyrrolyl, 2- or 3-pyridazinyl, 2-, 4- or 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 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-methylimidazol-2-, -4- or -5-yl, wherein the aryl radical or heteroaryl radical may be substituted up to two times by F, Cl, Br, OH, CF3, NO2, CN, OCF3, O—(C1-C6)-alkyl, S—(C1-C6)-alkyl, SO—(C1-C6)-alkyl, SO2-(C1-C6)-alkyl, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, COOH, COO(C1-C6)alkyl, COO(C3-C6)cycloalkyl, CONH2, CONH(C1-C6)alkyl, CON[(C1-C6)alkyl]2, CONH(C3-C6)cycloalkyl, NH2, NH—CO—(C1-C6)-alkyl, NH—CO-phenyl, pyrrolidin-1-yl, morpholin-1-yl, piperidin-1-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, (CH2)n-phenyl, O—(CH2)n-phenyl, S—(CH2)n-phenyl, or SO2-(CH2)n-phenyl, where n=0-3);
- and its physiologically tolerated salts and physiologically functional derivatives.
4 more elements
Dependencies are inferred from the claim text.