Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-09-27
1995-02-21
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546326, 546344, 549 71, 549 72, 549 78, 549487, 549484, 549497, C07D21363, C07D21369, C07D21379, C07D33338
Patent
active
053917537
ABSTRACT:
Compounds of the formula ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1-6 carbons, halogen or lower alkoxy of 1-6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1-6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 1-10 carbons, cyclo or branch-chained alkyl of 3-10 carbons, and straight chain alkenyl having 2-10 carbons, or cyclo or branched chained alkenyl of 3-10 carbons; X is thienyl, pyridyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl and oxazolyl; 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, or CR.sub. 7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1-5 carbons, R.sub.8 is an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is alkyl of 1-10 carbons, phenyl or lower alkylphenyl, R.sub.12 is lower alkyl, and R.sub.13 is divalent alkyl radical of 2-5 carbons, have retinoic acid 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: 4855320 (1989-08-01), Chatterjee et al.
patent: 4895868 (1990-01-01), 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
A General Synthesis of Terminal and Internal Arylalkynes by the Palladium-Catalyzed Reaction of Alkynylzinc Reagnets 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 Negishi, Anthony O. King, and William L. Klima, J. Org. Chem. 45 No. 12, 1980 p. 2526.
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. 33:404-407 (1985).
Kagechika et. al. in J. Med. Chem. 31:2182-2192 (1988).
Synthesis of 2,2.varies.0-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, vol. 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 (1989).
Davis et al. J. Organomettalic Chem 387 (1990) 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, vol. 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.
Chemical Abstracts, vol. 104 (1986) 33961h (Karminski-Zamola et al.
Heterocycles (1985) 23(6) 1497-501.
Chemical Abstracts vol. 79 (1973) 18713a.
Allergan Inc.
Baran Robert J.
Cebulak Mary C.
Raymond Richard L.
Szekeres Gabor L.
LandOfFree
Heteroaryl substituted phenylethenyl compounds having retinoid-l does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Heteroaryl substituted phenylethenyl compounds having retinoid-l, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Heteroaryl substituted phenylethenyl compounds having retinoid-l will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1931430