Corticotropin releasing factor antagonists

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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514255, 514256, 514269, 514272, 514274, 514275, 514312, 514314, 514332, 514333, 514335, 514336, 514337, 514338, 514339, 514340, 514341, 514342, 514343, 514344, 514345, 514349, 514350, 514351, 514352, 514354, 514355, 514356, 514357, 546153, 546155, 546156, 546157, 546159, 546167, 546255, 546256, 546261, 546262, 546263, 546264, 546265, 546266, 546267, 5462784, 546296, 546297, 546307, 544295, 544296, 544397, 544300, 544310, 544316, 544317, 544319, 544320, 544326, 544328, 544329, 544331, 544333, 544405, A61K 31

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059624795

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

This invention relates to pyridines, pyrimidines, purinones, pyrrolopyrimidinones and pyrrolopyridinones, processes for preparing them, pharmaceutical compositions containing them, and methods of using them to treat certain central nervous system (CNS) and other disorders.
CRF antagonists are mentioned in U.S. Pat. Nos. 4,605,642 and 5,063,245 referring to peptides and pyrazolinones, respectively. The importance of CRF antagonists is set out in the literature, e.g., as discussed in U.S. Pat. No. 5,063,245, which is incorporated herein by reference. A recent outline of the different activities possessed by CRF antagonists is found in M. J. Owens et al., Pharm. Rev., Vol. 43, pages 425 to 473 (1991), also incorporated herein by reference. Based on the research described in these two and other references, CRF antagonists are effective in the treatment of a wide range of stress-related illnesses, such as depression, anxiety, headache, irritable bowel syndrome, inflammatory diseases, immune suppression, Alzheimer's disease, gastrointestinal diseases, anorexia nervosa, hemorrhagic stress, drug and alcohol withdrawal symptoms, drug addiction, infertility, head trauma, stroke, and stress-induced infections in humans and animals.


SUMMARY OF THE INVENTION

The present invention relates to a compound of the formula ##STR2## or a pharmaceutically acceptable salt thereof, wherein the dashed lines represent optional double bonds; R.sub.12)R.sub.1, --NHCHR.sub.1 R.sub.2, --OCHR.sub.1 R.sub.2, --SCHR.sub.1 R.sub.2, --CHR.sub.2 OR.sub.12, --CHR.sub.2 SR.sub.12, --C(S)R.sub.2 or --C(O)R.sub.2 ; trifluoromethoxy, methyl, ethyl, thiomethoxy, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or trifluoromethyl; wherein R.sub.13 and R.sub.14 are each, independently, hydrogen, trifluoromethyl or methyl, or one of R.sub.13 and R.sub.14 is cyano and the other is hydrogen or methyl; one or two substituents R.sub.8 independently selected from the group consisting of hydroxy, fluoro, chloro, bromo, iodo, CF.sub.3, C.sub.1 -C.sub.4 alkoxy, --O--CO--(C.sub.1 -C.sub.4 alkyl), --O--CO--NH(C.sub.1 -C.sub.4 alkyl), --O--CO--N(C.sub.1 -C.sub.4 alkyl)(C.sub.1 -C.sub.2 alkyl), --NH(C.sub.1 -C.sub.4 alkyl), --N(C.sub.1 -C.sub.2 alkyl)(C.sub.1 -C.sub.4 alkyl), --S(C.sub.1 -C.sub.4 alkyl), --N(C.sub.1 -C.sub.4 alkyl)CO(C.sub.1 -C.sub.4 alkyl), --NHCO(C.sub.1 -C.sub.4 alkyl), --COO(C.sub.1 -C.sub.4 alkyl), --CONH(C.sub.1 -C.sub.4 alkyl), --CON(C.sub.1 -C.sub.4 alkyl)(C.sub.1 -C.sub.2 alkyl), CN, NO.sub.2, --SO(C.sub.1 -C.sub.4 alkyl) and --SO.sub.2 (C.sub.1 -C.sub.4 alkyl), and wherein said C.sub.1 -C.sub.6 alkyl and the (C.sub.1 -C.sub.4)alkyl moieties in the foregoing R.sub.1 groups may optionally contain one carbon-carbon double or triple bond; alkylene)aryl wherein said aryl is phenyl, naphthyl, thienyl, benzothienyl, pyridyl, quinolyl, pyrazinyl, pyrimidyl, imidazolyl, furanyl, benzofuranyl, benzothiazolyl, isothiazolyl, benzisothiazolyl, benzisoxazolyl, benzimidazolyl, indolyl, or benzoxazolyl; 3- to 8-membered cycloalkyl or --(C.sub.1 -C.sub.6 alkylene)cycloalkyl, wherein one or two of the ring carbons of said cycloalkyl having at least 4 ring members and the cycloalkyl moiety of said --(C.sub.1 -C.sub.6 alkylene)cycloalkyl having at least 4 ring members may optionally be replaced by an oxygen or sulfur atom or by N--R.sub.9 wherein R.sub.9 is hydrogen or C.sub.1 -C.sub.4 alkyl; and wherein each of the foregoing R.sub.2 groups may optionally be substituted with from one to three substituents independently selected from chloro, fluoro and C.sub.1 -C.sub.4 alkyl, or with one substituent selected from bromo, iodo, C.sub.1 -C.sub.6 alkoxy, --O--CO--(C.sub.1 -C.sub.6 alkyl), --O--CO--N(C.sub.1 -C.sub.4 alkyl)(C.sub.1 -C.sub.2 alkyl), --S(C.sub.1 -C.sub.6 alkyl), CN, NO.sub.2, --SO(C.sub.1 -C.sub.4 alkyl), and --SO.sub.2 (C.sub.1 -C.sub.4 alkyl), and wherein said C.sub.1 -C.sub.12 alkyl and the C.sub.1 -C.sub.4 alkylene moiety of said --(C.sub.1 -C.sub.4 alkylene)aryl may optionally contain one carbon-carbon double or triple

REFERENCES:
patent: 4605642 (1986-08-01), Rivier et al.
patent: 4839353 (1989-06-01), Hosoi et al.
patent: 5063245 (1991-11-01), Abren et al.
patent: 5691364 (1997-11-01), Buckman et al.
Cossey et al., Pyridines and Pyridinium Salts from Cyanoacetamides, Australian Journal of Chemistry, vol. 29, No. 5, pp. 1039-1050, May 1976.
De Souza, Corticotropin-Releasing Factor Receptors: Physiology, Pharmacology, Biochemistry and Role in Central Nervous System and Immune Disorders, Psychoneuroendocrinology, vol. 20, No. 8, pp. 789-819, 1995.
Fackelmann, K.A., and Raloff, J., Psychological Stress Linked to Cancer, Science News (Sep. 25, 1993) vol. 144, p. 196.
Lyons, M.K., et al., Corticotropin releasing factor antagonist reduces ischemic hippocampal neuronal injury, Brain Research, vol. 545 Issue 1-2, pp. 339-342 (1991).
Stratakis, C.A., and Chrousos G.P., Hypothalamic Hormones GnRH, TRH, GHRH, SRIF, CRH, and Dopamine, Endocrinology: Basic and Clinical Principles, pp. 185-209, (Humana Press, Tofowa, NJ, 1997).
Strijbos, P.J.L.M., et al., Brain Res. 656, pp. 405-408 (1991).
Chalmers D.T., et al., Corticotrophin-releasing factors molecular biology to drug design, Trends in Pharmacological Sciences, vol. 17, pp. 166-172 (1996).
Owens et al. Pharm. Rev., vol. 43 (1991), pp. 425-473.
Chem. Abstr., vol. 72 (1970), Abstract No. 11080v.
Robbins, et al., Can. J. Chem., vol. 55 (1977) pp. 1251-1259.

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