NEW DERIVATIVES OF HETEROCICLIC OXYMS, ITS PREPARATION PROCEDURE AND ITS USE AS HYPOGLUCEMIC AND HYPOLIPIDEMIC AGENTS.

摘要

Compound of formula (I): ** see formula ** where - X represents an oxygen or sulfur atom - A represents an (C1-C6) alkylene chain of which a CH2 group can be optionally substituted by a heteroatom selected from oxygen or sulfur or by an NRa group (where Ra represents a hydrogen atom or a linear or branched (C 1-C 6) alkyl group), or by a phenylene or naphthylene group, - R 1 and R 2, identical or different , represent a hydrogen atom or a linear or branched (C1-C6) alkyl, linear or branched (C2-C6) alkenyl, linear or branched (C2-C6) alkynyl, aryl, linear (C1-C6) aryl alkyl branched, linear or branched (C 2-C 6) linear or branched aryl (C 2 -C 6) aryl, linear or branched, heteroaryl, straight or branched C 1 -C 6 alkyl, straight or branched heteroarylalkyl (C 2 -C 6) branched, straight or branched (C2-C6) heteroarylalkyl, C3-C8 cycloalkyl, linear or branched (C1-C6) cycloalkyl or C1-C6 alkyl or polyhaloalkyl (C1- C6) linear or branched, - R 3 and R 4, identical or different, represent a hydrogen or halogen atom, or a group R, OR or NRR '', where R and R '', identical or different, represent a hydrogen atom or a linear or branched (C1-C6) alkyl group, linear or branched (C2-C6) alkenyl, linear or branched (C2-C6) alkynyl, aryl, linear or branched (C1-C6) arylalkyl, arylalkenyl ( C2-C6) linear or branched, linear or branched (C2-C6) arylalkyl, heteroaryl, straight or branched (C 1-C 6) heteroarylalkyl, straight or branched (C 2-C 6) heteroarylalkyl, heteroarylalkyl (C 2-C) 6) linear or branched, cycloalkyl (C 3-C 8), cycloalkyl (C 3-C 8) linear or branched (C 1-C 6) alkyl or linear or branched (C1-C6) polyhaloalkyl, or R 3 and R 4 together with the carbon atoms that carry them, when they are carried by two adjacent carbon atoms, a cycle comprising 5 or 6 links and may optionally contain a heteroatom selected from ox oxygen, sulfur and nitrogen, - B represents a linear or branched (C1-C6) alkyl or linear or branched (C2-C6) alkenyl group, these groups being substituted: with a group of formula (II): ** see formula * * where ** see formula ** -R 5 represents a group ** see formula ** where Z represents an oxygen or sulfur atom and R and R '', identical or different, are as defined above, and -R 6 represents an aryl, arylalkyl group whose alkyl part contains from 1 to 6 carbon atoms and which can be linear or branched, heteroaryl, heteroarylalkyl whose alkyl part contains from 1 to 6 carbon atoms and can be linear or branched, CN , tetrazol, -OR, -NRR '' ** see formula **, where Z is as defined above and R and R '', identical or different, can take the same values as defined above, or with a group R 7 where R 7 represents a CN group, tetrazole, where Z is as defined above and R and R '', identical or different, they can take the same values as defined above, n represents 0, 1, 2, 3, 4, 5 or 6, and R 8 and R 9, identical or different, represent a hydrogen atom or an alkyl group (C 1-C 6) linear or branched, it being understood that R 8 and R 9 cannot simultaneously represent a hydrogen atom, - or B represents a group of formula (II) or a group R 7 as defined above, it being understood that: - the oxime R 1 -C (= N-OR 2) - can be of Z or E configuration, - by aryl is meant a phenyl, naphthyl or biphenyl group, these groups being optionally partially hydrogenated, - by heteroaryl any mono or bicyclic aromatic group is understood to contain 5 to 10 links, optionally being partially hydrogenated in one of the cycles in the case of bicyclic heteroaryls, and containing 1 to 3 heteroatoms selected from oxygen, nitrogen and sulfur, where aryl and heteroaryl groups as well defined may be optionally substituted with 1 to 3 groups, identical or different, selected from linear or branched (C 1-C 6) alkyl, linear or branched (C 1-C 6) polyhaloalkyl, linear (C 1-C 6) alkoxy or branched, hydroxyl, carboxyl, formyl, linear or branched (C 1-C 6) acyl, aroyl, NRbRc (where Rb and Rc, identical or different, represent a hydrogen atom, a linear (C1-C6) alkyl group or branched, aryl or heteroaryl), ester, amido, nitro, cyano, or halogen atoms, their enantiomers and diastereoisomers, as well as their addition salts of a pharmaceutically acceptable acid or base.