Synthesis and retinoid compounds having negative hormone activity and / or antagonists.

1996 
The invention provides a compound of formula: where X is S, O, NR '' where R '' is H or alkyl of 1 to 6 carbon atoms, x is [C (R 1) 2] n, where R 1 ES INDE pendently HO alkyl of 1 to 6 carbons, and n is an integer between 0 and 2; R 2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, CF 3, alkyl of 1 to 6 carbon atoms substituted by fluorine, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons; R 3 is hydrogen, alkyl of 1 to 6 carbons, or fluoro LOWER; M is an integer of 0-3; O is an integer from 0-3 VALUE; Y is a phenyl or naphthyl, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl being optionally substituted such groups phenyl and heteroaryl FOR ONE OR TWO GROUPS R 2; A is (CH 2) Q wherein Q is 0-5, lower alkyl CHAIN ​​BRANCHED 3-6 carbons, cycloalkyl 3-6 carbons, alkenyl of 2-6 CARBONOSY 1 or 2 double bonds, alkynyl 2-6 CARBONOS and 1 or 2 triple bonds: B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, 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 7, CR 7 (OR 12) SUB, 2, CR 7 OR 13 OO trialkyl silyl LOWER WHERE R 7 is an alkyl, cycloalkyl or alkenyl from 1 to 5 carbon atoms; R 8 is an alkyl group of 1 to 10 carbons or trimethylsilylalkyl, wherein the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or alkylphenyl LOWER; R 11 is lower alkyl, phenyl or alkylphenyl LOWER; R 12 is alkyl INFER IOR; YR 13 is an alkyl radical divalent 2-5 carbons; YR 14 EN (R 15 R - phenyl, (R 15) SUB, R heteroaryl, wherein the heteroaryl group has 1 to 3 heteroatoms selected from the group consisting of O, SYN, r is an integer of 0-5 YR 15 is independently H, F, Cl, Br, I, NO 2, N (R 8) 2, N (R 8) COR 8, NR 8 CON (R 8) 2, OH, OCOR 8, OH, OCOR 8, OR 8, CN, an alkyl group of 1 to 10 carbons, an alkyl group of 1 to 10 carbon atoms, substituted alkenyl group of 1 to 10 carbons and 1 to 3 double bonds, an alkynyl group having 1 to 10 carbons and 1 to 3 triple bonds, or trialkylsilyl group or trialkylsiloxy WHERE alkyl groups independently have 1 to 6 C; R 16 is H, alkyl of 1 to 6 carbon atoms; R 17 is H, alkyl INFE RIOR 1 to 6 carbons, OH or OCOR 11, and p is 0 or 1 with the proviso that, when p is 1, NO substituent group R 17, m is an integer between 0 and 2.
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