Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2006-12-26
2006-12-26
Balasubramanian, Venkataraman (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C514S246000
Reexamination Certificate
active
07153961
ABSTRACT:
The present invention provides 4-(bis(2-methoxyethyl)amino)-2,7-dimethyl-8-(2-methyl-4-methoxyphenyl)-[1,5-a]-pyrazolo-1,3,5-triazine benzenesulfonate salt and a crystalline polymorph thereof. Further provided are pharmaceutical compositions containing the salt and methods of treating CRF-related disorders using said salt.
REFERENCES:
patent: 3910907 (1975-10-01), O'Brien et al.
patent: 4824834 (1989-04-01), Fujii et al.
patent: 4892576 (1990-01-01), Kruger et al.
patent: 5137887 (1992-08-01), Hashimoto et al.
patent: 5484760 (1996-01-01), Bussler et al.
patent: 6060478 (2000-05-01), Gilligan et al.
patent: 6124289 (2000-09-01), He et al.
patent: 6136809 (2000-10-01), Gilligan et al.
patent: 6191131 (2001-02-01), He et al.
patent: 6313124 (2001-11-01), He et al.
patent: 6358950 (2002-03-01), He et al.
patent: 2003/0125330 (2003-07-01), Gilligan
patent: 1 088 574 (1994-06-01), None
patent: 0 269 859 (1988-06-01), None
patent: 0 594 149 (1994-04-01), None
patent: 2001-302658 (2001-10-01), None
patent: WO 98/03510 (1998-01-01), None
patent: WO 98/08847 (1998-03-01), None
patent: WO 01/23388 (2001-04-01), None
patent: WO 02/72202 (2002-09-01), None
Mitchell, Neurosci. Biobehav. Rev. 22(5); 635-651, 1998.
Albert, A.H., et al., “Synthesis of 2,4-dimethylpyrazolo[1,5-a]-1,2,5-triazine,”J. Het. Chem.,1973, p. 885.
Battaglia, G., et al., “characterization of corticotrophin-releasing factor receptor-mediated adenylate cyclase activity in the rat central nervous system,”Synapse,1987, 1, 572-581.
Beyer, H., et al., “Zur umsetzung von ketonitrilen mit hydrazinderivaten der kohlensäure,”Verlag Chemie GMBH Weinheim/Bergstr.,,1960, 9, 2209-2216.
Boissier, J.-R., et al., “A new method for rapid screening of minor transquillizers in mice,”Eur. J. of Pharmacol.,1968, 4, 145-151.
Bruni, F., et al., “Reactivity of 7-(2-dimethylaminovinyl)pyrazolo[1,5-a]pyrimidines: synthesis of pyrazolo[1,5-a][3,4-e]pyrimidine derivatives as potential benzodiazepine receptor ligands. 2.,”J. Heterocycl. Chem.,1995, 32, 291-298.
Collington, E.W., et al., “A facile and specific conversion of allylic alcohols to allylic chlorides,”J. Org. Chem.,1971, 36(20), 3044-3196.
Crossland, R.K., et al., “A facile synthesis of methanesulfonate esters,”J. Org. Chem.,1970, 35(9), 3195-3196.
Cusmano, S., et al., “Comportamento dei legami lidenici verso alcuni reattivi. Struttura delle sostanze ottenute per azione della semicarbazide sui benzalderivati di corpi β-chetonitriliei—Nota V.,”Gazz. Chim. Ital.,1952, 82, 373-384 (Italian).
Dunn, A.J., et al., “Physiological and behavioral responses to corticotrophin-releasing factor administration: is CRF a mediator of anxiety or stress responses,”Brain Res. Rev.,1990, 15, 71-100.
Funk, D., et al., “Role of catecholamines in the frontal cortex in the modulation of basal and stress-induced autonomic output in rats,”Brain Res.,1996, 741, 220-229.
Griebel, G., et al., “Genetic differences in the mouse defense test battery,”Aggress. Behav.,1997, 23, 19-31.
Grigoriadis D.E., et al., “Corticotropin-releasing factor (CRF) receptors in intermediate lobe of the pituitary: biochemical chjaracterization and autoradiographic localization,”Peptides,1989, 10, 179-188.
He, L., et al., “4-(1,3-dimethoxyprop-2-ylamino)-2,7-dimethyl-8-(2,4-dichlorophenyl)-pyrazolo[1,5-a]-1,3,5-triazine: a potent, orally bioavailable CRF1receptor,”J. Med. Chem.,2000, 43, 449-456.
Kobe, J., et al., “The chemistry of 4-hydrazino-7-phenylpyrazolo[1,5-a]-1,3,5-triazines,”J. Het. Chem.,1974, 991-996.
Kobe, J., et al., “The synthesis and chemical reactions of certain pyrazolo[1,5-a]-1,3,5-traizines(1),”J. Het. Chem.,1974, 199-204.
Meyers, A.I., et al., “An efficient total synthesis of propylure, the highly active sex attractant for the pink bollworm moth,”Tetrahedron,1971, 27, 5979-5985.
Misslin, R., et al., “Behavioural validation of a light/dark choice procedure for testing anti-anxiety agents,”Behav. Process,1989, 18, 119-132.
Munson, P.J., et al., “LIGAND: A versatile computerized approach for characterization of ligand-binding systems,”Anal. Biochem.,1980, 107, 220-239.
Nagel, D.L., et al., “Synthesis of alkyl-substituted benzo[c]phenanthrenes and chrysenes by photocyclization,”J. Org. Chem.,1977, 42(22), 3626-3628.
Nishida, A., et al., “Rotational isomerism in fluorine derivatives XIV conformational equillbria of β-substituted 9-(2-cyanomethylphenyl) fluorine derivatives,”Technol. Rep. Yamaguchi Univ.,1988, 4(2), 145-150.
Novinson, T., et al., “synthesis of unsymmetrical 2,4-dialkylpyrazolo[1,5-a]-1,3,5-triazines,”J. Het. Chem.,1974, 691-695.
Pellow, S., et al., “Validation of open: closed arm entries in an elevated plus-maze as a measure of anxiety in the rat,”J. of Neurosci. Methods,1985, 14, 149-167.
Page, G.A., et al., “The synthesis of benzcyclohepten-6-one,”J. Am. Chem. Soc.,1953, 75, 2053-2055.
Pietraszuk, C., et al., “Cross-metathesis of vinylsilanes with olefins in the presence of Grubbs' catalyst,”Tetrahedron Lett.,2001, 42, 1175-1178.
Porsolt, R.D., et al., “Depression: a new animal model sensitive to antidepressant treatment,”Nature,1977, 266, 730-732.
Principles of Process Research and Chemical Development in the Pharmaceutical Industry,Wiley,1998, p. 38-40.
Rapoport, H., et al., “The synthesis of 2,3,4-trimethoxybenzcyclohepten-6-one,”J. Am. Chem. Soc.,1951, 73, 2239-2241.
Senga, K., et al., “Synthesis and enzymic activity of various substituted pyrazolo[1,5-a]-1,3,5-triazines as adenosine cyclic 3′,5′-phosphate phosphodiesterase inhibitors,”J. Med. Chem.,1982, 25, 243-249.
Stogryn, E.L., “A new synthesis of 3,4-(difluoromethylenedioxy)benzaldehydr,”J. Org. Chem.,1972, 37(4), p. 673.
Vogel, J.R., et al., “A simple and reliable conflict procedure for testing anti-anxiety agents,”Psychopharmcologia (Berl.),1971, 21, 1-7.
Willner, P., et al., “An animal model of anhedonia,”Clin. Neuropharmacol.,1992, 15(suppl. 1), 550A-551A.
Wynn, P.C., et al., “Regulation of corticotrophin-releasing factor (CRF) receptors in the rat pituitary gland: effects of adrenalectomy on CRF receptors and corticotroph responses,”Endocrinology,1985, 116(4), 1653-1659.
Logemann, W., et al., “Studien in der heterocyclischen reihe, II. Mitteil.*): Die synthese von 1.3.5-triazine und 5-oxy-isoxazol-derivaten,”Chem. Ber.,1954, 87, 1175-1179 (German).
Bellec, C., et al., “Structure de derives de β- cétonitriles. II. Tautomérie hydrazone-énehydrazine; etude des configurations,”Beilstein Institut. Zur Foerderung Der,Accession No. 3384927, 1988, II-441-II-448 (Summary in English).
Souchay, et al., “CHDCAQ,”S.R.Hebd. Seances Acad. Sci. Ser. C,1973, p. 1457 (Accession No. 2981462, 1 page).
Yamashita, M., “BCSJA8,”Bull. Chem. Soc. Jpn.,1941, 16, 413-415 (Accession No. 3384927, 1 page).
Gilligan Paul J.
Meenan Paul A.
Rabel Riley Shelly Renee
Balasubramanian Venkataraman
Bristol-Myers Squibb Pharma Co.
Makujina Shah R.
Woodcock & Washburn LLP
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