Diarylsulfones as 5-HT2A antagonists

Details Diarylsulfones as 5-HT2A antagonists Diarylsulfones as 5-HT2A antagonists

2007-04-27

2008-12-23

Saeed, Kamal A (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Sulfur, selenium or tellurium compound

C568S032000, C568S034000

Reexamination Certificate

active

07468393

ABSTRACT:
Compounds of formula I:are potent and selective antagonists of the human 5-HT2Areceptor, and hence useful in treatment of a variety of adverse conditions of the CNS.

REFERENCES:
patent: 2784184 (1957-03-01), Zweidler et al.
patent: 3256340 (1966-06-01), Russell
patent: 4128552 (1978-12-01), Wise et al.
patent: 4218455 (1980-08-01), Wise et al.
patent: 4812461 (1989-03-01), Antoku et al.
patent: 4977165 (1990-12-01), Oinuma et al.
patent: 6479479 (2002-11-01), Achard et al.
patent: 6559166 (2003-05-01), Blurton et al.
patent: 6872717 (2005-03-01), Achard et al.
patent: 2003/0130287 (2003-07-01), Ackermann et al.
patent: 2003/0181464 (2003-09-01), Burkamp et al.
patent: WO 96/02509 (1996-02-01), None
patent: WO 96/35666 (1996-11-01), None
patent: WO 97/21680 (1997-06-01), None
patent: WO 00/31037 (2000-06-01), None
patent: WO 01/40230 (2001-06-01), None
patent: WO 02/083645 (2002-10-01), None
patent: WO 2002/088113 (2002-11-01), None
patent: WO 02/100864 (2002-12-01), None
patent: WO 2005/016920 (2005-02-01), None
patent: WO 2005/082343 (2005-09-01), None
Abstarct of Simalty-Siemiatycki et al., Bulletin de la Societe Chimique de France (1962), p. 125-8.
Stephen R. Fletcher, et al: “4-(Phenylsulfonyl)piperidines: Novel, Selective, and Bioavailable 5-HT2A Receptor Antagonist”. Journal of Medicinal Chemistry, 2002, vol. 45, No. 2, pp. 492-503.
Fukami, Jiichi et al: “Preparation of Hydantoin Derivatives as Cardiovascular Agents”, XP002356147, Database Caplus Chemical Abstracts Service, Database accession No. 1997:189919.
Zhi Chen, et al., “Preparation of New Anti-Tubulin Ligands through a Dual-Mode, Addition-Elimination Reaction to a Bromo-Substituted alpha, beta-Unsaturated Sulfoxide”, Journal of Organic Chemistry, vol. 65, No. 25, 2000, pp. 8811-8815.
Franc C. et al: “A General Synthesis of 2-Formyl-3-Arylpyrroles” Tetrahedrono Letters, pp. 4555-4558, Jun. 11, 1999.
Masquelin T. et al: “A New Approach to the Synthesis of N-Protected 2- and 5-Substitituted 3-Halopyrroles” 1995. Synthesis pp. 276-784.
Shafiee A. et al: “Syntheses of 2-(2-Arylethyl)Imidazoles” 1998, Journal of Heterocyclic Chemistry, pp. 607-610.
Garcia Ruano J. L. et al: “Synthesis of chiral ortho-(p-tolylsulfinyl) benzyl ketones”, Oct. 25, 2004, Tetrahedron, pp. 10067-10075.
Alberola A. et al: “The reaction of beta-aminoenones with substituted acetonitriles. Regiospecific synthesis of 2(1H)-pyridones”, 1987, Journal of Heterocyclic Chemistry, Heterocorporation. pp. 709-713.
Ayambem A. et al: “Endgroup substituent effects on the rate/extent of network formation and adhesion for phenylethynyl-terminated poly(arylene ether sulfone) oligomers”, Jun. 1000, Polymer, pp. 5109-5124.
Mokhtar Hassan et al: “Synthesis of some substituted pyrazole-3-carboxylic acids with possible hypoglycemic and antimicrobial activity. Part 1” 1978, Pharmazie, pp. 649-651.
Database Beilstein, Beilstein Institut zur Forderung der Chemischen Wissenschaft, Frankfurt am Main, DE: XP00235619, retrieved from XFIRE Database accession No. 3062620, 3100377, 3101626, 3099644, 3101535; J of Org Chem., vol. 33, No. 6, 1968, pp. 2228-2233.
Ghosez L. et al: “Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (−)-rhazinilam and its analogues”, 2001, Canadian Journal of Chemistry National Research Council. pp. 1827-1840.
Database Beilstein, Databas accession No. 2599161, 2537238, 7117539, 2541627, 2541951; Bull. Soc. Chim. Fr., 1962, pp. 129-131.
Zachary P. Demiko and K. Barry Sharpless: “A Click Chemistry Approach to Tetrazoles by Huigsen 1, 3-Dipolar Cycloaddition: Synthesis of 5-Sulfonyl Tetrazoles from Azides and Sulfonyl Cyanides” Angew. Chem. Int. Ed, vol. 41, No. 12, 2002, pp. 2110-2113.
Michael E. Wright and Edward G. Toplikar: “A preliminary study of poly(p-phenylene) based nonlinea optical materials” Macromol. Chem. Phys., vol. 196, 1995, pp. 3563-3575.
Mitsuhiro Yoshimatsu et al: “A Convenient Synthesis of Alkynlpyrazoles” J. Chem. Soc. Perkin Trans. I. 1997, pgaes. 695-700.
Matthew D. Cliff and Stephen G. Pyne: “Palladium Catalysed Coupling of Imidazoles to Alkynyl and Vinyl Sustrates” Tetrahedron, vol. 52, No. 43, 1996, pp. 13703-13712.
Werner Hinz et al: “Pyrrole Studies 34, Synthesis of 1,2-Di(2-pyroolyl)ethenes and Related Compounds” Synthesis, 1986, pp. 620-623.
Matthew S. Addie and Richard J. K. Taylor: “New routes to 5-substituted oxazoles”, J. Chem. Soc. Perkin I, 2000, pp. 527-531.
Jose L. Garcia Ruano et al: “Remote Sterocontrol by Sulfinyl Groups: Reduction of delta-Ketosulfoxides”, J. Org. Chem., vol. 70, May 2, 2005, pp. 1796-1801, XP002356128.
Jose L. Garcia Ruano et : “Highly Stereoselective vinylogous Pummerer Reaction Mediated by ME3SIX”, Org. Lett., vol. 7, No. 1, Dec. 14, 2004, pp. 19-22.
S. Wakabayashi et al: Ligand coupling of 2-Pyridyl Sulfoxides Having an sp2 Stereocenter at the alpha-Position: A novel Preparation of alpha-stilbazoles, Heteroatom Chemistry, vol. 1, No. 3, 1990, pp. 225-232.
Shafiee, A. et al: “Synthesis of substituted, 1, 2, 4-triazoles”, XP002356151, Database Caplus Database accession No. 1993-191644: Journal of Heterocyclic Chemistry, 29(7), 1863-5, 1992.
Murata, Yasue et al: “Syntheses of 3, 4-disubstituted 2-tosylpyrroles and 5-tosyl-1, 5-dihydro-2H-pyrrol-2-ones starting from ethyl, 3, 4-disbustituted 2-pyrrolecarboxylates” XP002356152, Database Caplus, Database accession No. 1996: 717134; Bulletin of The Chemical Society of Japan, 69(11), 3339-3344, 1996.
Najera, Carmen et al: “Dilithiated (E)-N-isoprypyl-3-tosylacrylamide: a new beta-acylvinyl anion equivalent in organic synthesis”, XP002356153, Database Caplus, Database accession No. 1990:118553; Journal of The Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, (8) 1387-91, 1989.
Van Nispen, Simon P. J. M. et al: “Chemistry of sulfonylmethyl isocyanides. 21. Use of dilithio(tolysulfonyl)methy isocyanide in the synthesis of oxazoles and imidazoles”, XP002356154. Datbase Caplus, Database accession No. 1981:103454; Tetrahedron Letters, 21(38), 3723-6, 1980.
Settambolo, Roberta et al: “Synthesis of 3-vinylpyrrole”, XP002356155, Database Caplus, Database accession No. 1994:77125; Journal of Organic Chemistry, 58(27), 7899-902, 1993.
Kinoshita, Hideki et al: “A new and effective aminomethylation of the use of N-(p-toluenesulfonylmethyl)-p-toluenesulfonamide as an equievalent of methanimine. A convenient perparatio of pyrrole compounds”, XP002356156. Database Caplus,Database accession No. 1987:84319; Chemistry Letters, (6) 1033-6, 1986, 1033-6, 1986.
Shafiee, A. et al: “Syntheses of 2-(2-arylethyl)imidazoels” XP002356157, Database Caplus, Database accession No. 1998:516917; Journal of Heterocyclic Chemistry, 35(3), 607-610, 1998.
Hinz, Werner et al: “Pyrrole studies: 34, Synthesis of 1, 2-di(2-pyrrolyl)ethenes and related compounds”, XP00235618, Database Caplus, Database accession No. 1987:176094; Synthesis, (8), 620-3, 1986.
Greenhouse, Robert et al: Synthesis of alkylpyrroles by the sodium borohydride reduction of acylpyrroles, XP002356159, Database Caplus, Database accession No. 1985:471148; Journal of Organic Chemistry, 50(16), 2961-5, 1985.
Kinoshita, Hideki et al: “Convenient and regioselective syntheses of 3,4-disubstituted .DELTA. 3-pyrrolin-2-one derivatives starting from 2-tosyl-3, 4-disubstituted pyrroles”, XP002356160, Database Caplus, Database accession No. 1994-134181; Chemistry Letters, (8), 1437-40, 1993.
Hopman, Johan C. P. et al: “Chirality preservatin in pyrolinone iron tetracarbonyl complexes—a route to enantiopure 5-substituted pyrrolinones”, XP002356161, Database Caplus, Database accession No. 1995-488644; Journal of the Chemical Society, Chemi

Affiliated with

Also associated with

Rating

Diarylsulfones as 5-HT2A antagonists does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Diarylsulfones as 5-HT2A antagonists, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Diarylsulfones as 5-HT2A antagonists will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4037173