C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
167/208, 260/302
C07D 263/30 (2006.01) C07D 263/32 (2006.01) C07D 277/20 (2006.01) C07D 277/22 (2006.01) C07D 277/24 (2006.01) C07D 277/32 (2006.01) C07D 277/40 (2006.01) C07D 277/42 (2006.01) C07D 277/46 (2006.01) C07D 413/04 (2006.01) C07D 417/04 (2006.01)
Patent
CA 1296002
Abstract Substituted thiazoles and oxazoles Compounds of formula I Image (I) (wherein A represents an n-alkylene group with 2 or 3 carbon atoms optionally monosubstituted or disubstituted by methyl or ethyl groups X represents an oxygen or sulphur atom; R1 represents a hydrogen or halogen atom, or a trifluoromethyl, C1-3 alkyl, phenyl or piperidino group or an amino group optionally substituted by one or two C1-3 alkyl groups or by one C1-3 alkanoyl or benzoyl group; R2 represents a hydrogen atom or a C1-3 alkyl group; R3 represents a hydrogen atom or a C1-3 alkyl group optionally substituted in the 2- or 3-position by a hydroxyl group, or R3 together with R4 represents a (C1-3alkoxy)carbonylmethylene, an ethylene or an oxoethylene groups R4 represents a hydrogen atom, a C3-5 alkenyl group or a C1-3 alkyl group optionally substituted by a phenyl, carboxyl, (C1-3alkoxy)carbonyl or cyano group or, in the 2- or 3-position, by a hydroxyl group and R5 represents a hydroxyl, C1-3 alkoxy, carboxyl, (C1-3-alkoxy)carbonyl, aminocarbonyl, (C1-3alkyl)amino- carbonyl or di(C1-3-alkyl)aminocarbonyl group, a C1-6 alkoxy group substituted by a terminal carboxyl, (C1-3alkoxy)carbonyl, aminocarbonyl, (C1-3alkyl)amino- carbonyl or di(C1-3-alkyl)aminocarbonyl group, or a C2-7 alkoxy group substituted by a terminal hydroxyl, C1-3 alkoxy, phenyl(C1-3alkoxy), amino, (C1-3alkyl)amino, di(C1-3-alkyl)amino, pyrrolidino, piperidino or hexamethyleneimino group, or an optionally C1-3 alkyl group substtuted ethenyl group substituted by a terminal carboxyl, (C1-3alkoxy)carbonyl, aminocarbonyl, (C1-3alkyl)aminocarbonyl or di(C1-3-alkyl)aminocarbonyl group), the optical isomers, diastereomers and addition salts thereof are disclosed. The new lactams of formula I, their optical isomers and diastereomers are valuable intermediates for the preparation of morpholines of formula I (in which R3 and R4 together represent an ethylene group). Such morpholines and other compounds of formula I (except the lactams), their optical isomers and their diastereomers, as well as their acid addition salts, have valuable pharmacological properties, namely an action on the metabolism, in particular they cause reductions in blood sugar and body fat levels as well as in the levels of atherogenic .beta.-lipoproteins VLDL and LDL.
531681
Grell Wolfgang
Hurnaus Rudolf
Reiffen Manfred
Rupprecht Eckhard
Sauter Robert
Dr. Karl Thomae Gesellschaft Mit Beschrankter Haftung
Fetherstonhaugh & Co.
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