Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-09-24
1995-11-21
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549398, 549406, C07D33504, C07D31104, C07D31176
Patent
active
054688795
ABSTRACT:
Compounds of the formula ##STR1## where R.sub.1 and R.sub.2, independently are alkyl groups having 2 to 8 carbons; R.sub.3 is hydrogen or lower alkyl; X is S, O or N--R.sub.4 where R.sub.4 is hydrogen or lower alkyl; Y is phenyl or pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, and pyrazinyl; A is (CH.sub.2).sub.n where n is 0-5, or lower branched chain alkyl, 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 hydrogen, COOH or a salt thereof, COOR.sub.5, CONR.sub.6 R.sub.7, --CH.sub.2 OH, CH.sub.2 OR.sub.8, CH.sub.2 OCOR.sub.8, CHO, CH(OR.sub.9).sub.2, CHOR.sub.10 O, --COR.sub.11, CR.sub.11 (OR.sub.9).sub.2, or CR.sub.11 OR.sub.10 O, where R.sub.5 is alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or R.sub.5 is phenyl or lower alkylphenyl, R.sub.6 and R.sub.7 independently are hydrogen, alkyl of 1 to 10 carbons, or cycloalkyl of 5 to 10 carbons, or phenyl or lower alkylphenyl, R.sub.8 is alkyl of 1 to 10 carbons, phenyl or lower alkylphenyl, R.sub.9 is lower alkyl, R.sub.10 is divalent alkyl radical of 2-5 carbons and R.sub.11 is alkyl, cycloalkyl or alkenyl containing 1 to 5 carbons, have retinoic acid like 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: 5068255 (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 Reagents with Aryl Halides by Anthony O. King and Ei-ichi Negishi, J. Org. Chem., 43, No. 2, 1978, p. 358.
Conversion by 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.
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 Human Press, pp. 54-55.
V. Retinoid Structure-Biological Activity Relationships, Chemistry and Biology of Synthetic Retinoids, pp. 324-356.
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.
Allergan Inc.
Baran Robert J.
Covington Raymond
Ivy C. Warren
Szekeres Gabor L.
LandOfFree
Disubstituted acetylenes bearing heterobicyclic groups and heter does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Disubstituted acetylenes bearing heterobicyclic groups and heter, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Disubstituted acetylenes bearing heterobicyclic groups and heter will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1138494