¬4-(1,2-epoxycyclohexanyl) but-3-en-1-ynyl| aromatic and...

C - Chemistry – Metallurgy – 07 – D

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C07D 303/38 (2006.01) A61K 31/33 (2006.01) C07D 303/40 (2006.01) C07D 405/06 (2006.01) C07D 407/06 (2006.01) C07D 409/00 (2006.01) C07D 409/06 (2006.01) C07D 413/06 (2006.01) C07D 417/06 (2006.01)

Patent

CA 2180009

Compounds of Formula (1) where R1-R7 are hydrogen, lower alkyl of 1-6 carbons, or halogen; Y is phenyl, pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl ou oxazolyl; A is (CH2)n, where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR14, CR14(OR12)2, or CR14OR13O, where R8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or R8 is phenyl or lower alkylphenyl, R9 and R10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, R13 is divalent alkyl radical of 2-5 carbons and R14 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, have retinoid-like biological activity.

Composés de formule (1) dans laquelle R¿1? - R¿7? sont hydrogène, alkyle inférieur ayant de 1 à 6 atomes de carbone, ou halogène; Y est phényle, pyridyle, furyle, thiényle, pyridazinyle, pyrimidinyle, pyrazinyle, thiazolyle ou oxazolyle; A est (CH¿2?)¿n?, n valant de 0 à 5, alkyle inférieur à chaîne ramifiée ayant 3 à 6 atomes de carbone, cycloalkyle ayant 3 à 6 atomes de carbone, alcényle ayant 2 à 6 atomes de carbone et 1 ou 2 liaisons doubles, alcynyle ayant 2 à 6 atomes de carbone et 1 ou 2 liaisons triples; B est hydrogène, COOH ou un sel pharmaceutiquement acceptable de ladite substance, COOR¿8?, CONR¿9?R¿10?, -CH¿2?OH, CH¿2?OR¿11?, CH¿2?OCOR¿11?, CHO, CH(OR¿12?)¿2?, CHOR¿13?O, -COR¿14?, CR¿14?(OR¿12?)¿2?, ou CR¿14?OR¿13?O, R¿8? étant un groupe alkyle ayant 1 à 10 atomes de carbone, ou un groupe cycloalkyle ayant 5 à 10 atomes de carbone, ou un groupe cycloalkyle ayant 5 à 10 atomes de carbon, ou bien R¿8? étant phényle ou alkylphényle inférieur, R¿9? et R¿10? étant indépendamment hydrogène, un groupe alkyle de 1 à 10 atomes de carbone, ou un groupe cycloalkyle ayant 5 à 10 atomes de carbone, ou phényle ou alkylphényle inférieur, R¿11? étant alkyle inférieur, phényle ou alkylphényle inférieur, R¿12? étant alkyle inférieur, R¿13? étant un radical alkyle divalent ayant 2 à 5 atomes de carbone et R¿14? étant un groupe alkyle, cycloalkyle ou alcényle contenant 1 à 5 atomes de carbone. Ces composés présentent une activité biologique de type rétinoïde.

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