Synthesis of thienopyridinone compounds and related...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

07576211

ABSTRACT:
The invention relates to 5-HT receptor agonists and partial agonists. Novel thienopyridinone compounds represented by Formula I, and synthesis and uses thereof for treating diseases mediated directly or indirectly by 5-HT receptors, are disclosed. Such conditions include Alzheimer's disease, cognition disorders, irritable bowel syndrome, nausea, emesis, vomiting, prokinesia, gastroesophageal reflux disease, nonulcer dyspepsia, depression, anxiety, urinary incontinence, migraine, arrhythmia, atrial fibrillation, ischemic stroke, gastritis, gastric emptying disorders, feeding disorders, gastrointestinal disorders, constipation, erectile dysfunction, and respiratory depression. Methods of preparation and novel intermediates and pharmaceutical salts thereof are also included.

REFERENCES:
patent: 3069412 (1962-12-01), Melville et al.
patent: 3658807 (1972-04-01), Schmidt et al.
patent: 4146716 (1979-03-01), Cox et al.
patent: 4316020 (1982-02-01), Reissenweber
patent: 5155155 (1992-10-01), Jurlaro et al.
patent: 5219864 (1993-06-01), Suzuki et al.
patent: 5227387 (1993-07-01), Dreikorn et al.
patent: 5236917 (1993-08-01), Dunlap et al.
patent: 5371074 (1994-12-01), Dunlap et al.
patent: 5378679 (1995-01-01), Nuebling et al.
patent: 5571815 (1996-11-01), Schaper et al.
patent: 5591751 (1997-01-01), Fujioka et al.
patent: 5593943 (1997-01-01), Nuebling et al.
patent: 5596012 (1997-01-01), Dunlap et al.
patent: 5650422 (1997-07-01), Dunlap et al.
patent: 5753673 (1998-05-01), Ohuchi et al.
patent: 5798451 (1998-08-01), von Deyn et al.
patent: 5874432 (1999-02-01), Dunlap et al.
patent: 5972841 (1999-10-01), von Deyn et al.
patent: 6103903 (2000-08-01), Cai et al.
patent: 6159962 (2000-12-01), Steiner et al.
patent: 6187788 (2001-02-01), Furuya et al.
patent: 6222034 (2001-04-01), Steiner et al.
patent: 6232320 (2001-05-01), Stewart et al.
patent: 6300333 (2001-10-01), Schaper et al.
patent: 6340759 (2002-01-01), Ueno et al.
patent: 6596727 (2003-07-01), Schaper et al.
patent: 6924283 (2005-08-01), Thorarensen
patent: 7030240 (2006-04-01), Dhanoa et al.
patent: 7119205 (2006-10-01), Iyengar et al.
patent: 7153858 (2006-12-01), Dhanoa et al.
patent: 2002/0028782 (2002-03-01), Castelhano et al.
patent: 2004/0138238 (2004-07-01), Dhanoa et al.
patent: 2005/0049243 (2005-03-01), Ballard et al.
patent: 2005/0065176 (2005-03-01), Field et al.
patent: 2005/0137142 (2005-06-01), Schulz et al.
patent: 2005/0222175 (2005-10-01), Dhanoa et al.
patent: 2005/0222176 (2005-10-01), Dhanoa et al.
patent: 2005/0256153 (2005-11-01), Dhanoa et al.
patent: 2006/0079547 (2006-04-01), Dhanoa et al.
patent: 2006/0084805 (2006-04-01), Dhanoa et al.
patent: 2006/0084806 (2006-04-01), Sridharan et al.
patent: 2006/0205737 (2006-09-01), Becker et al.
patent: 2006/0234998 (2006-10-01), Dhanoa et al.
patent: 2007/0004742 (2007-01-01), Dhanoa et al.
patent: 2007/0173487 (2007-07-01), Saha et al.
patent: 0447891 (1991-09-01), None
patent: 0503844 (1992-09-01), None
patent: 0505058 (1992-09-01), None
patent: 0 710 662 (1998-05-01), None
patent: 1 018 513 (2000-07-01), None
patent: 1 018 513 (2000-07-01), None
patent: 0 710 662 (2001-04-01), None
patent: 1229025 (2002-08-01), None
patent: 1325921 (2003-07-01), None
patent: 1 018 513 (2006-02-01), None
patent: 2295387 (1996-05-01), None
patent: 11 130777 (1999-05-01), None
patent: WO 94/12176 (1994-06-01), None
patent: WO 94/22871 (1994-10-01), None
patent: WO2005/121151 (1995-12-01), None
patent: WO-00/64441 (2000-11-01), None
patent: WO 01/14333 (2001-03-01), None
patent: WO 01/25218 (2001-04-01), None
patent: WO 02/102797 (2002-12-01), None
patent: WO 2004/014850 (2004-02-01), None
patent: WO 2004/017950 (2004-03-01), None
patent: WO 2004/030629 (2004-04-01), None
patent: WO 2004/034963 (2004-04-01), None
patent: WO 2004/089312 (2004-10-01), None
patent: WO 2006/041985 (2006-04-01), None
patent: WO 2007/058805 (2007-05-01), None
Jerry March Advanced Organic Chemistry 4th Edition 1992 by John Wiley & Sons: New York pp. 378-383.
Hwang, Ki-Jun; Lee, Tae-Suk; Kim, Ki-Won; Kim, Beom-Tae; Lee, Chul-Min; Park, Eun-Young; Woo, Ran-Sook. “4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine derivatives: synthesis and their biological evaluation for the glycine site acting on the N-methyl-D-aspartate (NMDA) receptor” Archives of Pharmacal Research 2001, 24(4), 270-275.
Hutchins, R.O. et. al. J. Org. Chem. 1977, 42, 82-91.
Barker, John M.: Huddleston, Patrick R.; Holmes, David “Thienopyridines. Part 6. Synthesis and nucleophilic substitution of some chlorothieno[2,3-b]pyridine derivatives, and comparisons with the analogous quinoline compounds” Journal of Chemical Research, Synopses 1985 (7), 214-15.
Gordon W. Gribble “Sodium borohydride in carboxylic acid media: a phenomenal reduction system” Chemical Society Reviews, 1998, 27 395-40.
Takashi Tojo, Glen W. Spears, Kiyoshi Tsuji, Hiroaki Nishimura, Takashi Ogino, Nobuo Seki Aiko Sugiyama and Masaaki Matsuo “Quinoline-3-carbothioamides and Related Compounds as Novel Immunomodulating Agents” Bioorganic & Medicinal Chemistry Letters 2002 12 2427-2430.
Coppola et. al. Journal of Organic Chemistry 41 (5), 1976, 825-831.
Lamlrault, L. et al., “Combined Treatment with Galanthaminium Bromide, a New Chollnesterase Inhibitor, and RS 67333, a Partial Agonist of 5-HT4 Receptors, Enhances Place and Object Recognition In Young Adult and Old Rats.” Progress in Neuro-Psychopharmacology & Biological Psychiatry 27 (2003) 185-195.
Moser, Paul C., et al., “SL65.0155, A Novel 5-Hydroxytryplamine4 Receptor Partial Agonist with Potent Cognition-Enhancing Properties,” The Journal of Pharmacology and Experimental Therapeutics, 302:731-741, 2002.
Science IP Search, Apr. 30, 2004.
Science IP Search, May 11, 2004.
Stachel, Hans-Dietrich, et al., “Derivatives of Oxalyldimalonic Acid,” 1995.
Suzuki, M., “Synthesis and Evaluation of Novel 2-Oxo-1,2-dihydro-3-Quinollnecarboxamide Derivatives as Potent and Selective Serotonin 5-HT4 Receprot Agonists,” Chem Pharm. Bull., 49(1) 29-39, 2001.
Buchheit et al.J. Med. Chem.,38(13):2326-2330 (1995).
Buchheit et al.J. Med. Chem.,38(13):2331-2338 (1995).
Kaumann, A.J.Naunyn-Schmiedeberg's Arch. Pharmacol.,342:619-622 (1990).
Abenhaim et al., N. Engl. J. Med, 335(9):609-616 (1996).
Bonhaus, D.W., et al., British J. Pharmac., 1999 (127) 1075-1082.
Brea et al., J. Med. Chem., 45:54-71 (2002).
International Search Report for PCT/US2003/23539 mailed Jul. 23, 2004.
Doggrell, Sheila A., Expert Opin. Investig. Drugs, 2003 (12) 805-823.
Farber et al., N. Engl. J. Med., 351(16):1655-1665 (2004).
Fishman, Chest, 114(3):242S-247S (1998).
Fitzgerald et al., Mol. Pharmacol., 57:75-81 (2000).
Kennett et al., Neuropharmacol., 36(2):233-239 (1997).
Kursar et al., Mol. Pharmacol., 46(2):227-234 (1994).
Kuryshev et al., J. Pharmacol. Exp. Ther., 295(2):614-620 (2000).
Launay et al., Nat. Med., 8(10):1129-1135 (2002).
MacLean, Trends Pharmacol. Sci., 20(12):490-495 (1999).
Manivet et al., J. Biol. Chem., 277(19):17170-17178 (2002).
Marcos et al., Circ. Res., 94:1263-1270 (2004).
Nauser et al., Am. Fam. Physician, 63(9):1789-1798 (2001).
Nebigil et al., Proc. Natl. Acad. Sci. U.S.A., 97(6):2591-2596 (2000).
Poissonnet et al., Mini-Rev. Med. Chem., 4(3):325-330 (2004).
Recanatini, M., et al., Acetylcholinesterase Inhibitors in the Context of Therapeutic Strategies to Combat Alzheimer's Disease, Expert Opinion on Therapeutic Patents, Ashley Publications, GB, vol. 12, No. 12, 2002, pp. 1853-1865.
Rich et al., Chest, 117(3):870-874 (2000).
Roth, B. L., et al., Expert Opin. Ther. Targets, 2001 (5) 685-695.
Rothman et al., Circulation, 102:2836-2841 (2000).
Setola et al., Mol. Pharmacol., 63(6):1223-1229 (2003).
Teoh et al., “Hypoxia Enhances 5-HT28Receptor Response and Expression in the Rat Pulmonary Artery”, Abstract only, International Conference of the American Thoracic Society, San Diego (May 24, 2005).
Ullmer et al., Br. J. Pharmacol., 117(6):1081-1088 (1996).
Ullmer et al., FEBS Lett., 370(3):215-221 (

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Synthesis of thienopyridinone compounds and related... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of thienopyridinone compounds and related..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of thienopyridinone compounds and related... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4130652

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.