Substituted phenylethenyl compounds having retinoid-like biologi

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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560 9, 560 18, 560 55, 560 65, 562431, 562432, 562474, 564162, 564177, 568325, 568331, 568425, 568439, 568442, 568715, 568807, 568812, 568626, 568659, 568661, 554229, 554231, C07C32100

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053268989

ABSTRACT:
Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, halogen or lower alkoxy of 1 to 6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1 to 6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 2 to 10 carbons, cyclo or branch-chained alkyl of 3 to 10 carbons, and straight chain alkenyl having 2 to 10 carbons, or cyclo or branched chained alkenyl of 3 to 10 carbons, and the Z-Y substituent is in a 1,2 (ortho) or 1,3 (meta) position on the phenyl ring relative to the ethene moiety; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons, have retinoid like biological activity.

REFERENCES:
patent: 4096341 (1978-06-01), Frazer
patent: 4326055 (1982-04-01), Loeliger
patent: 4695649 (1987-09-01), Magami et al.
patent: 4723028 (1988-02-01), Shudo
patent: 4739098 (1988-04-01), Chandraratna
patent: 4740519 (1988-04-01), Shroot et al.
patent: 4801733 (1989-01-01), Wuest et al.
patent: 4810804 (1989-03-01), Chandraratna
patent: 4826969 (1989-05-01), Maignan et al.
patent: 4855320 (1989-08-01), Chatterjee et al.
patent: 4895868 (1990-01-01), Chandraratna
patent: 4898833 (1990-02-01), Lang et al.
patent: 4980369 (1990-12-01), Chandraratna
patent: 4992468 (1991-02-01), Chandraratna
patent: 5006550 (1991-04-01), Chandraratna
patent: 5013744 (1991-05-01), Chandraratna
patent: 5015658 (1991-05-01), Chandraratna
patent: 5023341 (1991-06-01), Chandraratna
patent: 5045551 (1991-09-01), Chandraratna
patent: 5053523 (1991-10-01), Chandraratna
patent: 5068252 (1991-11-01), Chandraratna
patent: 5089509 (1992-02-01), Chandraratna
A General Synthesis of Terminal and Internal Arylalkynes by the Palladium-Catalyzed Reaction of Alkynylzinc Reagents with Aryl Halides by Anthony O. King and Ei-ichi Negishi, J. Org. Chem 43 No. 2, 1978 p. 358.
Conversion of Methyl Ketones into Terminal Acetylenes and (E)-Tri-substituted Olefins of Terpenoid Origin by Ei-ichi, Anthony O. King, and William L. Klima, J. Org. Chem. 45 No. 12, 1980, p. 2526.
Sporn et al., in J. Amer. Acad. Derm. 15:756-764 (1986).
A Convenient Synthesis of Ethynylarenes and Diethynylarenes by S. Takahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis 1980 pp. 627-630.
Shudo et al. in Chem. Phar. Bull. 33:404-407 (1985).
Kagechika et al. in J. Med. Chem. 31:2182-2192 (1988).
Chemistry and Biology of Synthetic Retinoids by Marcia I. Dawson and William H. Okamura, published by CRC Press Inc., 1990, pp. 334-335, 354.
Synthesis of 2,2'-Diacyl-1,1'-biaryls. Regiocontrolled Protection of . . . by Mervic, et al, J. Org. Chem., No. 45, pp. 4720-4725, 1980.

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