Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1994-12-29
1996-05-07
Brust, Joseph Paul
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
556415, 556416, 556436, 560 80, 560102, 560107, 560128, 560255, 562492, 562510, 564180, 568327, 568440, 568592, 568659, 568808, C07C25534, C07C25540, C07C 6366
Patent
active
055148255
ABSTRACT:
Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 10 carbons; R.sub.2 and R.sub.3 are hydrogen, or alkyl of 1 to 6 carbons and the substituted ethynyl group occupies either the 2 or the 3 position of the tetrahydronaphthalene nucleus; m is an integer having the value of 0-3; o is an integer having the value 0-4; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R.sub.2 groups; A is (CH.sub.2).sub.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, 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, CR.sub.7 OR.sub.13 O, or tri-lower alkylsilyl, 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 (trimethylsilyl)alkyl where the alkyl group has 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 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons, and R.sub.19 is independently hydrogen, alkyl of 1 to 10 carbons, fluoro-substituted alkyl of 1 to 10 carbons, alkenyl of 2 to 10 carbons and having 1 to 3 double bonds, alkynyl having 2 to 10 carbons and 1 to 3 triple bonds, carbocyclic aryl selected from the group consisting of phenyl, C.sub.1 -C.sub.10 -alkylphenyl, naphthyl, C.sub.1 -C.sub.10 -alkylnaphthyl, phenyl-C.sub.1 -C.sub.10 alkyl, napthyl-C.sub.1 -C.sub.10 alkyl; CN, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, (CH.sub.2).sub.p CO.sub.2 R.sub.8, (CH.sub.2).sub.p CH.sub.2 OH, (CH.sub.2).sub.p CH.sub.2 OR.sub.11, (CH.sub.2).sub.p CH.sub.2 OCOR.sub.11, where p is an integer between 0 to 10, or the two R.sub.19 groups jointly represent 3 to 6 methylene groups which together with the alkylidene carbon complete a ring, have retinoid like biological activity.
REFERENCES:
patent: 4096341 (1978-06-01), Frazer
patent: 4326055 (1982-04-01), Loeliger
patent: 4391731 (1983-07-01), Boller et al.
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: 4810804 (1989-03-01), Chandraratna
patent: 4826969 (1989-05-01), Maignan et al.
patent: 4826984 (1989-05-01), Berlin et al.
patent: 4855320 (1989-08-01), Chatterjee et al.
patent: 4895868 (1990-01-01), Chandraratna
patent: 4927947 (1990-05-01), Chandraratna
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: 5037825 (1991-08-01), Klaus et al.
patent: 5045551 (1991-09-01), Chandraratna
patent: 5053523 (1991-10-01), Chandraratna
patent: 5068252 (1991-11-01), Chandraratna
patent: 5089509 (1992-02-01), Chandraratna
patent: 5130335 (1992-07-01), Chandraratna
patent: 5134159 (1992-07-01), Chandraratna
patent: 5162546 (1992-11-01), Chandraratna
patent: 5175185 (1992-12-01), Chandraratna
patent: 5183827 (1993-02-01), Chandraratna
patent: 5202471 (1993-04-01), Chandraratna
patent: 5231113 (1993-07-01), Chandraratna
patent: 5234926 (1993-08-01), Chandraratna
patent: 5248777 (1993-09-01), Chandraratna
patent: 5264456 (1993-11-01), Chandraratna
patent: 5264578 (1993-11-01), Chandraratna
patent: 5272156 (1993-12-01), Chandraratna
patent: 5278318 (1994-01-01), Chandraratna
patent: 5324744 (1994-06-01), Chandraratna
patent: 5324840 (1994-06-01), Chandraratna
patent: 5326898 (1994-07-01), Chandraratna
patent: 5344959 (1994-09-01), Chandraratna
patent: 5346895 (1994-09-01), Chandraratna
patent: 5346915 (1994-09-01), Chandraratna
patent: 5348972 (1994-09-01), Chandraratna
patent: 5348975 (1994-09-01), Chandraratna
patent: 5349105 (1994-09-01), Chandraratna
patent: 5354752 (1994-10-01), Chandraratna
patent: 5380877 (1995-01-01), Chandraratna
patent: 5391753 (1995-02-01), 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) pp. 358-360.
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) pp. 2526-2528.
Sporn et. al. in J. Amer. Acad. Derm. 15: pp. 756-764 (1986).
A Convenient Synthesis of Ethynylarenes and Diethylnylarenes by S. Takahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis (1980) pp. 627-630.
Shudo et al. in Chem. Phar. Bull. 33 pp. 404-407, (1985).
Kagechika et. al. in J. Med. Chem. 31 pp. 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).
A Dopamine Receptor Model and Its Application in the Design of a New Class of Rigid Pyrrolo 2,3-g!isoquinoline Antipsychotics, Gary L. Olson, et al. American Chemical Society, (1981), Vo. 24, No. 9, pp. 1026-1031.
6.2.3 Conformational Restriction, Williams, et al., Drug Discovery and Development, (1987) The Humana Press, pp. 54-55.
V. Retinoid Structure-Biological Activity Relationships, Chemistry and Biology of Synthetic Retinoids, pp. 324-356, (1990).
Davis et al. J. Organomettalic Chem, 387 (1990) pp. 381-390.
Effects of 13-Cis-Retinoic Acid, All-Trans-Retinoic Acid, and Acitretin on the Proliferation, Lipid Synthesis and Keratin Expression of Cultured Human Sebocytes In Vitro, C. C. Zouboulis, The Journal of Investigative Dermatology, vol. 96, No. 5, (May 1991), pp. 792-797.
Organ maintenance of human sebaceous glands: in vitro effects of 13-cis retinoic acid and testosterone, John Ridden, et al., Journal of Cell Science, Vo. 95, (1990), pp. 125-136.
Characterization of Human Sebaceous Cells In Vitro, Thomas I. Doran, et al., The Journal of Investigative Dermatology, vol. 96, No. 3, Mar., 1991 pp. 341-348.
Synthesis and Evaluation of Stilbene and Dihydrostilbene Derivatives as Potential Anticancer Agents That Inhibit Tubulin Polymerization by Cushman, Mark et.al. J.Med. Chem (1991), 34, pp. 2579-2588.
Synthesis and Evaluation of New Protein-Tyrosine Kinase Inhibitors. Part 1. Pyridine-Containing Stilbenes and Amides by Cushman, Mark et al. Bioorganic & Medicinal Chemistry Letters, vol. 1, No.4, pp. 211-214, (1991).
Di-and Tri-methoxystyryl Derivatives of Heterocyclic Nitrogen Compounds by Bahner, C. T. et al. Arzneim-Forsch./Drug Res, 31 (I), Nr. 3 (1981), pp. 404-.
Retinobenzoic acids. 3. Structure-Activity Relationships of retinoidal Azobenzene-4-carboxylic acids and Stilbene-4-carboxylic acids by H. Kagechika et al., Journal of Medicinal Chemistry, (1989), 32, pp. 1098-1108.
Beard Richard L.
Chandraratna Roshantha A.
Duong Tien T.
Johnson Alan T.
Lin Yuan
Allergan Inc.
Baran Robert J.
Brust Joseph Paul
Szekeres Gabor L.
Voet Martin A.
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