Aryl or heteroaryl amides of tetrahydronaphthalene, chroman,...

C - Chemistry – Metallurgy – 07 – D

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C07D 311/58 (2006.01) C07C 233/81 (2006.01) C07C 233/88 (2006.01) C07C 235/66 (2006.01) C07C 327/48 (2006.01) C07D 215/40 (2006.01) C07D 215/48 (2006.01) C07D 335/06 (2006.01) C07D 401/12 (2006.01) C07D 405/12 (2006.01) C07D 407/12 (2006.01) C07D 409/12 (2006.01) C07D 413/12 (2006.01) C07D 417/12 (2006.01) C07F 7/10 (2006.01)

Patent

CA 2238274

Compounds of formula (I) where X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons, or X is [C(R1)2]n where n is an integer between 0 and 2; 1; Y is a phenyl or naphthyl group, or heteroaryl group; W is a substituent selected from the group consisting of F, Br, Cl, I, C1-6alkyl, fluoro substituted C1-5 alkyl, NO2, N3, OH, OCH2OCH3, OC1-10alkyl, tetrazol, CN, SO2C1-6-alkyl, SO2C1-6-fluoro substituted alkyl, SO-C1-6 alkyl, CO-C1-6alkyl, COOR8, phenyl, phenyl itself substituted with a W group other than with phenyl or substituted phenyl; L is -(C-Z)-NH- or -HN-(C=Z)-; Z is O or S; A is (CH2)q where q 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, and B is COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, CR7OR13O, where R1 -R13 and o, p, m, n, r are as defined in claim 1, have retinoid-like biological activity.

Composés de formule (I) où X est S, O, NR', où R' est H ou alkyle avec 1 à 6 carbones, ou X est [C(R1)2]n où n est un entier compris entre 0 et 2; 1; Y est un groupe phényle ou naphtyle, ou un groupe hétéroaryle; W est un substituant choisi dans le groupe constitué de F, Br, Cl, I, C1-6 alkyle, C1-6 alkyle fluoro-substitué, NO2, N3, OH, OCH2OCH3, OC1-10 alkyle, tétrazole, CN, SO2C1-6-alkyle, SO2C1-6 alkyle fluoro-substitué, SO-C1-6 alkyle, CO-C1-6 alkyle, COOR8, phényle, le phényle étant substitué avec un groupe W autre que phényle ou phényle substitué; L est -(C=Z)-NH- or -HN-(C=Z)-; Z est O ou S; A est (CH2)q où q est 0-5, alkyle inférieur à chaîne ramifiée possédant 3-6 carbones, cycloalkyle possédant 3-6 carbones, alcényle possédant 2-6 carbones et 1 ou 2 doubles liaisons, alcynyle possédant 2-6 carbones et 1 ou 2 triples liaisons; et B est COOH ou un de ses sels pharmaceutiquement acceptables COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, CR7OR13O, où R1 -R13 et o, p, m, n, r sont tels que définis dans la revendication 1. Ces composés ont une activité biologique de type rétinoïde.

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