Dihydrobenzofuranyl alkanamines and methods for using same...

Details Dihydrobenzofuranyl alkanamines and methods for using same... Dihydrobenzofuranyl alkanamines and methods for using same...

Filed on

2004-10-21

Date issued

2010-06-01

Examiner

Andres, Janet L. (Department: 1625)

Patent Class

Organic compounds -- part of the class 532-570 series

SubClass

Organic compounds

SubSubClass

Heterocyclic carbon compounds containing a hetero ring...

Type

Reexamination Certificate

Status

active

Patent number

07728155

Description

ABSTRACT:
Compounds of formula 1 or pharmaceutically acceptable salts thereof are provided:which are agonists and partial agonists of the 2c subtype of brain serotonin receptors. The compounds, and compositions containing the compounds, can be used to treat a variety of central nervous system disorders such as schizophrenia.

REFERENCES:
patent: 3513239 (1970-05-01), Wiley
patent: 3759927 (1973-09-01), Huebner
patent: 5008286 (1991-04-01), Bair
patent: 5767132 (1998-06-01), Bottcher et al.
patent: 6255324 (2001-07-01), Heindel et al.
patent: 6569894 (2003-05-01), Takaki et al.
patent: 2165276 (1972-07-01), None
patent: 254 642 (1988-01-01), None
patent: 446 809 (1991-09-01), None
patent: 640 602 (1995-03-01), None
patent: 0 707 007 (1996-04-01), None
patent: 846 683 (1998-06-01), None
patent: 1 211 253 (2002-06-01), None
patent: 1 348 708 (2003-10-01), None
patent: 1 200 892 (1970-08-01), None
patent: 59186969 (1984-10-01), None
patent: 05 339271 (1993-12-01), None
patent: 06316563 (1994-11-01), None
patent: 2000007671 (2000-01-01), None
patent: 2000080091 (2000-03-01), None
patent: WO 91/17144 (1991-11-01), None
patent: WO 93/10089 (1993-05-01), None
patent: WO 94/18193 (1994-08-01), None
patent: WO 96/30367 (1996-10-01), None
patent: WO 00/76990 (2000-12-01), None
patent: WO 00/77001 (2000-12-01), None
patent: WO 00/77010 (2000-12-01), None
patent: WO 03/022813 (2003-03-01), None
patent: WO 03/022814 (2003-03-01), None
patent: WO 03/074051 (2003-09-01), None
Lucchetti et al , 123:256498 RN168823-00-5.
Dauksas et al 81:23665a (1973) abstract best available.
Patent Abstracts of Japan, vol. 018, No. 182 (C-1184), Mar. 29, 1994 & JP 05 339271 A (Kowa Co.), Dec. 21, 1993.
Morris, J. et al., “Synthesis and biological activity of a potent antiplatelet 7-aminofurochromone,”Bioorg Med Chem Letts, 1994, 4(21):2621-2626.
McNeel, T. E. et al., “Synthetic Approaches to 4,8-Dimethyl-5-(N-pyridiniummethyl)-4′-5′-dihydropsoralens and 4,8-Dimethyl-5′-(N-aminomethyl)-4′,5′-dihydropsoralens ′1,2,”Journal of Heterocyclic Chemistry, 2001, 38:909-916.
U.S. Appl. No. 10/970,714, filed Oct. 21, 2004, Gross et al.
U.S. Appl. No. 60/621,023, filed Oct. 21, 2004, Zhou et al.
U.S. Appl. No. 60/621,024, filed Oct. 21, 2004, Gontcharov et al.
Toyoshima, S. et al., “Studies on benzoheterocyclic derivatives. VII. Synthesis and pharmacological action of benzofuran derivatives,”Yakugaku Zasshi. May 1968;88(5):503-12. Japanese. [English abstract included].
Shinozaki, K. et al, “Synthesis and thromboxane A2 antagonistic activity activity of indane derivatives,” Bioorg Med Chem Lett. Feb. 8, 1999;9(3):401-6.
Allison, D. B. et al., “Antipsychotic-Induced Weight Gain: A Comprehensive Research Synthesis,” Am. J. Psychiatry, 1999, 156:1686-1696.
Masand, P. S., “Weight gain associated with psychotropic drugs,” Exp. Opin. Pharmacother., 2000, 1: 377-389.
Whitaker, R., “Atypical Antipsychotics: A Modest Advance in Treating Schizophrenia,” Spectrum Life Sciences. Decision Resources, 2000, 2:1-9.
Schotte, A. et al., “Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding,” Psychopharmacology, 1996, 124: 57-73.
Cowen, P. J. et al., “Hypophagic, Endocrine and Subjective Responses tom- Chlorophenylpiperazine in Healthy Men and Women,” Human Psychopharmacology, 1995, 10: 385-391.
Rosenzweig-Lipson, S. et al., “Antiobesity-like effects of the selective 5-HT2C Agonist Way,” ASPET abstract, 2000.
Di Matteo, V. et al., “Selective blockade of serotonin2C/2Breceptors enhances dopamine release in the rat nucleus accumbens,” Nueropharmacology, 1998, 37: 265-272.
Fox, S. H. et al., “Behavioral Effects of 5-HT2CReceptor Antagonism in the Substantia Nigra Zona Reticulata of the 6-Hydroxydopamine-Lesioned Rat Model of Parkinson's Disease,” Experimental Neurology, 1998, 151: 35-49.
Millan, M. J. et al., “Serotonin (5-HT)2Creceptors tonically inhibit dopamine (DA) and noradrenaline (NA), but not 5-HT, release in the frontal cortex in vivo,” Neuropharmacology, 1998, 37: 953-955.
Di Matteo, V. et al., “SB 242 084, a selective serotonin2Creceptor antagonist, increases dopaminergic transmissions in the mesolimbic system,” Nueropharmacology, 1999, 38: 1195-1205.
Di Giovanni, G. et al., “Preferential Modulation of Mesolimbic Vs. Nigrostriatal Dopaminergic Function by Serotonin2C/2BReceptor Agonists: A Combined In Vivo Electrophysiological and Microdialysis Study,” Synapse, 2000, 35: 53-61.
Lloyd-Williams, P. et al., “Atropisomerism, biphenyls and the Suzuki coupling: peptide antibiotics,” Chem. Soc. Rev., 2001, 30:145-157.
Wilen, S. H. et al., Tetrahedron, 1977, 33:2725-2736.
Wilen, S. H., Tables of Resolving Agents and Optical Resolutions, pp. 268-298, E.L. Eliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972.
Krogsgaard-Larson, et al., (ed.) Design and Application of Prodrugs, Textbook of Drug Design and Development, Ch. 5, 113-191 (1991).
Bundgaard, et al., Journal of Drug Delivery Reviews, 8:1-38 (1992).
Bundgaard, J. of Pharmaceutical Sciences, 77(4):285-298 (1988).
Higuchi and Stella (eds.) Prodrugs as Novel Drug Delivery Systems, American Chemical Society (1975) pp. 1-115 and 196-223.
Widder, et al. (ed.), Methods in Enzymology, vol. 4, Academic Press (1985) pp. 309-396.
Bundgaard (ed.), Design of Prodrugs, Elsevier (1985), Ch. 1 (pp. 1-92), Ch. 4 (pp. 157-176), Ch. 5 (pp. 177-198), and Ch. 6 (pp. 199-241).
Eliel, E.L.,Stereochemistry of Organic Compounds, John Wiley & Sons, 1994, pp. 1142-1155.
Al-Bojuk, N. R. et al., “Synthesis and vasorelaxant potency of monagra. A chiral 5-(2-methyl-2,3-dihydro-7-bezofuryl)pyrazolopyrimidone analog of Viagra,” Heterocycles, 2001, 55(9): 1789-1803.
Ferorelli, S. et al., “Lipase-mediated kinetic resolution of rigid clofibrate analogues with lipid-modifying activity,” Tetrahedron: Asymmetry, 2001, 12(6): 853-862.
Ramadas, S. et al., “Enantioselective acylation of 2-hydroxymethyl-2,3-kihydrobenzofurans catalyzed by lipase fromPseudomas cepacia(Amano PS) and total stereoselective synthesis of (-)-(R)-MEM-protected arthrographol,” Tetrahedron: Asymmetry, 2000, 11(16): 3375-3393.
Kakigami, T. et al., “Serotonin 5-HT4 receptor agonistic activity of the optical isomers of (±)-4-amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3-dihydro-2-methylbenzo[b]furan-7-carboxamide,” Chemical & Pharmaceutical Bulletin, 1998, 46(6): 1039-1043.
Kuroita, T. et al., “Synthesis and structure-activity relationships of 2,3-dihydrobenzofuran-7-carboxamide derivatives as potent serotonin-3 (5-HT3) receptor antagonists,” Chemical & Pharmaceutical Bulletin, 1994, 42(1): 95-100.
Takehara, S. et al., “New chiral dopants for FLC materials: optically active cyclic ethers,” Ferroelectrics, 1993, 148(1-4): 195-202.
Ceccarelli, S. et.al., “Synthesis of novel 2-substituted-5-oxycoumarans via a direct route to 2,3-dihydro-5-hydroxy-2-benzofuranacetic acids,” Journal of Heterocyclic Chemistry, May-Jun. 1993, 30(3): 679-90.
Ayer, W. et al., “Synthesis of (+/−) arthrographol,” Canadian Journal of Chemistry, 1991, 69(12): 1909-1916.
Kemp, D. S. et al., “New templates for prior thiol capture from xanthene, dibenzo[c,h]xanthen-7-one and 2-methylenedihydrobenzofuran,” Tetrahedron Letters, 1991, 32(26): 3009-3012.
Murakami, S. et al., “Antidopaminergic effects of the stereoisomers of N-[(1-alkyl-2-pyrrolidinyl)methyl]-5-sulfamoylbenzamides and -2,3-dihydro-benzofuran-7-carboxamides,” Journal of Medicinal Chemistry, 1991, 34(1): 261-267.
Yodo, M. et al., “Optical resolution and chiral synthesis of methyl 6,7-dichloro-2,3-dihydrobenzo[b]furan-2-carboxylate,” Chemical & Pharmaceutical Bulletin, 1988, 36(3): 902-913.
Chaudhuri, N. K. et al., ȁ

Affiliated with

Also associated with

Rating

Dihydrobenzofuranyl alkanamines and methods for using same... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Dihydrobenzofuranyl alkanamines and methods for using same..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Dihydrobenzofuranyl alkanamines and methods for using same... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4245364