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US 7,071,221 B2Granted
Heterocyclic oxime compounds
AssigneeLes Laboratoires Servier
InventorsVéronique Leclerc, Sylvie Pailloux, Pascal Carato, Carine Introvigne, Nicolas Lebegue, Pascal Berthelot, Catherine Dacquet, Jean Albert Boutin, Daniel Henri Caignard, Pierre Renard
Life of this patent
Estimating the term…
Abstract
Compounds of formula (I): wherein: X represents oxygen or sulphur or a group CH2 or R1, R2, R3, R4, R5 and R6 are as defined in the description, A represents an alkylene chain as defined in the description, B represents alkyl or alkenyl substituted by a group or R9, or B represents a group or R9, D represents a benzene, pyridine, pyrazine, pyrimidine or pyridazine nucleus. Medicaments
Claims20
A compound selected from those of formula (I):
- wherein:
- X represents oxygen sulfur, or
- R1 and R2, together form oxo,
- A represents a ethoxy
- R3 and R4, which may be the same or different, each represent hydrogen, halogen, R, OR or NRR′ wherein R and R′, which may be the same or different, each represent hydrogen, linear or branched (C1–C6)alkyl, linear or branched (C2–C6)alkenyl, linear or branched (C2–C6)alkynyl, aryl, aryl-(C1–C6)alkyl in which the alkyl moiety is linear or branched, aryl-(C2–C6)alkenyl in which the alkenyl moiety is linear or branched, aryl-(C2–C6)alkynyl in which the alkynyl moiety is linear or branched, heteroaryl, heteroaryl-(C1–C6)alkyl in which the alkyl moiety is linear or branched, heteroaryl-(C2–C6)alkenyl in which the alkenyl moiety is linear or branched, heteroaryl-(C2–C6)alkynyl in which the alkynyl moiety is linear or branched, (C3–C8)cycloalkyl, (C3–C8)cycloalkyl-(C1–C6)alkyl in which the alkyl moiety is linear or branched, or linear or branched (C1–C6)polyhaloalkyl,
- or R3 and R4, together with the carbon atoms carrying them, when they are carried by two adjacent carbon atoms, form a ring that has 5 or 6 ring members and that may contain a heteroatom selected from oxygen, sulphur and nitrogen,
- R5 and R6, which may be the same or different, each have the same meanings as R as defined hereinbefore,
- D represents a benezene nucleus,
- B represents linear or branched (C1–C6)alkyl or linear or branched (C2–C6)alkenyl, those groups being substituted:
- by a group of formula (II):
- wherein:
- —R7 represents
- wherein Z represents oxygen or sulphur, and R and R′, which may be the same or different are as defined hereinbefore,
- and R8 represents aryl, arylalkyl wherein the alkyl moiety contains from 1 to 6 carbon atoms and may be linear or branched, heteroaryl, heteroarylalkyl wherein the alkyl moiety contains from 1 to 6 carbon atoms and may be linear or branched, CN, tetrazole, —OR, —NRR′,
- wherein Z is as defined hereinbefore and R and R′, which may be the same or different are as defined hereinbefore,
- or by a group R9, wherein R9 represents CN, tetrazole,
- wherein Z is as defined hereinbefore and R and R′, which may be the same or different are as defined hereinbefore, n represents 0, 1, 2, 3, 4, 5 or 6, and R10 and R11, which may be the same or different, each represent hydrogen or linear or branched (C1–C6)alkyl, it being understood that R10 and R11 cannot simultaneously represent hydrogen,
- or B represents a group of formula (II) or a group R9 as defined hereinbefore,
- it being understood that:
- the oxime R6—C(═N—OR5)— may be of Z or E configuration,
- aryl means phenyl, naphthyl or biphenyl, it being possible for those groups to be partially hydrogenated,
- heteroaryl means any mono- or bi-cyclic aromatic group containing 5 to 10 members, which may be partially hydrogenated in one of the rings in the case of bicyclic heteroaryls and which contains 1 to 3 hetero atoms selected from oxygen, nitrogen and sulphur,
- it being possible for the aryl and heteroaryl groups thereby defined to be substituted by 1 or more groups selected from linear or branched (C1–C6)alkyl, linear or branched (C1–C6)polyhaloalkyl, linear or branched (C1–C6)alkoxy, hydroxy, carboxy, formyl, NRbRc wherein Rb and Rc, which may be the same or different, each represent hydrogen, linear or branched (C1–C6)alkyl, aryl or heteroaryl, ester, amido, nitro, cyano, and halogen,
- its enantiomers and diastereoisomers, and addition salts thereof with a pharmaceutically-acceptable acid or base.
21 more elements
Dependencies are inferred from the claim text.