Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2011-03-29
2011-03-29
Kumar, Shailendra (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C514S605000
Reexamination Certificate
active
07915448
ABSTRACT:
This invention provides a compound of the formula (I):wherein A and B are independently CR12or N; D and E are each independently CR9or N; R1represents (C1-C6)alkyl; R2represents hydrogen, halogen, hydroxy, (C1-C6) alkyl, halo(C1-C6) alkyl, hydroxy(C1-C6) alkyl, (C1-C6)alkoxy or (C1-C6)alkoxy-(C1-C6)alkyl; R3, R4, R5, R6, R10and R11each independently represent hydrogen, halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkyl or (C1-C6)alkoxy-(C1-C6)alkyl; or R3and R4are taken together with the carbon atom to which they are attached to form a 3- to 7-membered carbocyclic ring or heterocyclic ring in which one or two non-adjacent carbon atoms are optionally replaced by an oxygen atom, a sulfur atom or NH; R7and R9each independently represent hydrogen, halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl, (C1-C6)alkylsulfonyl, NH2, [(C1-C6)alkyl]NH—, [(C1-C6)alkyl]2N—, H2N—(C1-C6)alkoxy, (C1-C6)alkyl-NH—(C1-C6)alkoxy, [(C1-C6)alkyl]2N(C1-C6)alkoxy; H2N—(C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkyl-NH—(C1-C6)alkoxy-(C1-C6)alkyl, [(C1-C6)alkyl]2N(C1-C6)alkoxy-(C1-C6)alkyl or 5- or 6- membered heterocyclic ring containing at least one nitrogen atom; R8represents halogen, (C1-C6)alkyl, halo(C1-C6)alkyl, hydroxy(C1-C6)alkyl, (C1-C6)alkoxy, hydroxy(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkoxy, halo(C1-C6)alkylsulfonyl, halo(C1-C6)alkylsulfinyl, halo(C1-C6)alkoxy, halo(C1-C6)alkylthio, [(C1-C6)alkyl]NH— or [(C1-C6)alkyl]2N—; or R7and R8, when E is CR9, are taken together with the carbon atoms to which they are attached form a 5-8 membered carbocyclic or heterocyclic ring, in which one or two non-adjacent carbon atoms are optionally replaced by oxygen, sulfur, N or NH groups, wherein the carbocyclic ring or the heterocyclic ring is unsubstituted or substituted with one or more substituents each independently selected from the group consisting of hydroxy, (C1-C6)alkyl, (C1-C6)alkoxy and hydroxy(C1-C6)alkyl; and R12represents hydrogen, halogen, (C1-C6)alkyl or hydroxy(C1-C6)alkyl; or a pharmaceutically acceptable salt or solvate thereof.
REFERENCES:
patent: 4681952 (1987-07-01), Lantzsch et al.
patent: 4786646 (1988-11-01), Guthrie et al.
patent: 4927826 (1990-05-01), Guthrie et al.
patent: 4988734 (1991-01-01), Kraatz et al.
patent: 5082852 (1992-01-01), Kardorff et al.
patent: 5286736 (1994-02-01), Soyka et al.
patent: 5633239 (1997-05-01), Englert et al.
patent: 2003/0153596 (2003-08-01), Suh et al.
patent: 2004/0110754 (2004-06-01), Wu et al.
patent: 2004/0204341 (2004-10-01), Allen et al.
patent: 2005/0004122 (2005-01-01), Brown et al.
patent: 1314563 (1993-03-01), None
patent: 1108213 (1961-06-01), None
patent: 102005011056 (2005-10-01), None
patent: 1086191 (1967-10-01), None
patent: 1086192 (1967-10-01), None
patent: 56005435 (1981-01-01), None
patent: 5262698 (1992-03-01), None
patent: 8245555 (1996-09-01), None
patent: 2005314407 (2005-11-01), None
patent: 2293080 (2004-07-01), None
patent: WO 9406761 (1994-03-01), None
patent: WO 9427947 (1994-12-01), None
patent: WO 9748397 (1997-12-01), None
patent: WO 9748695 (1997-12-01), None
patent: WO 9926927 (1999-06-01), None
patent: WO 9931060 (1999-06-01), None
patent: WO 9931064 (1999-06-01), None
patent: WO 0021910 (2000-04-01), None
patent: WO 0111966 (2001-02-01), None
patent: WO 0155146 (2001-08-01), None
patent: WO 0202522 (2002-01-01), None
patent: WO 0216318 (2002-02-01), None
patent: WO 03082190 (2003-10-01), None
patent: WO 2004047738 (2004-06-01), None
patent: WO 2004108133 (2004-12-01), None
patent: WO 2005003084 (2005-01-01), None
patent: WO 2005007614 (2005-01-01), None
patent: WO 2005051890 (2005-06-01), None
patent: WO 2005068468 (2005-07-01), None
patent: WO 2006098554 (2006-09-01), None
West, Anthony R., Solid State Chemistry and its Applications, Wiley, New York, 1988, pp. 358 & 365.
Kim, et al., “Chain-branched 1,3-dibenzylthioureas as Vanilloid Receptor 1 Antagonists”,Bioorganic Medicinal Chemistry Letters, vol. 14(7), pp. 1751-1755 (2004).
Lee, et al., “N-(3-Acyloxy-2-benzylpropyl)-N'-[4-(methylsulfonylamino)benzyl]thiourea Analogues: Novel Potent and High Affinity Antagonists and Partial Antagonists of the Vanilloid Receptor”,J. Med. Chem., vol. 46(14), pp. 3116-3420 (2003).
Lee, et al., “Analysis of Structure-activity Relationships with the N-(3-Acyloxy-2-benzylpropyl)-N'[4-(methylsulfonylamino)benzyl]thiourea Template for Vanilloid Receptor 1 Antagonism”,Bioorganic&Medicinal Chemistry, vol. 12(13), pp. 3411-3420 (2004).
Rodriguez, et al., “A Novel Route to CycloPropyl Ketones, Aidehydes, and Carboxylic Acids”,Tetrahedron Letters, vol. 32(10), pp. 1275-1278 (1991).
Suh, et al., “Novel non-Vanilloid VR1 Antagonists of High Analgesic Effects and its Structural Requirement for VR1 Antagonistic Effects”,Bioorganic&Medicinal Chemistry Letters, vol. 13(24), pp. 4389-4396 (2003).
Tchilibon, et al., “Exploring Distal Regions of the A3 Adenosine Receptor Binding Site: Sterically Constrained N6-(2-phenylethyl)adenosine Derivatives as Potent Ligands”,Bioorganic&Medicinal Chemistry, vol. 12(9), pp. 2021-2034 (2004).
PCT International Search Report for PCT/IB2006/000557, Dated Jul. 5, 2006.
Dutch Industrial Property Office Search Report for Application No. 1031385, Dated Aug. 30, 2006.
Deal, et al., “Treatment of Arthritis with Topical Capsaicin: Double-Blind Trial”,Clin. Ther., vol. 13(3), pp. 383-395 (1991).
Fernihough, et al., “Regulation of Calcitonin Gene-related Peptide and TRPV1 in a Rat Model of Osteoarthritis”,Neuroscience Letters, vol. 388(2), pp. 75-80 (2005).
Honore, et al., “A-425619 [1-Isoquinolin-5-yl-3-(4-Trifluoromethyl-benzyl)-urea], a Novel Transient Receptor Potential Type V1 Receptor Antagonist, Relieves Pathophysiological Pain Associated with Inflammation and Tissue Injury in Rats”,J. Pharmacol. Exp. Ther., vol. 314(1), pp. 410-421 (2005).
Planellls-Cases, et al., “Functional Aspects and mechanisms of TRPV1 Involvement in Neurogenic Inflammation that Leads to Thermal Hyperalgesia”,Eur. J. Physiol., vol. 451, pp. 151-159 (2005).
Tchilibon, et al.,Bioorganic&Medicinal Chemistry, vol. 12, pp. 2021-2034 (2004) XP002385181.
Ferreira, et al.,Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry, vol, 1, pp. 25-29 (1982).
Kunz, et al.,Chem. Ber., vol. 116, pp. 220-229 (1983).
“First International Meeting on Neurobiology of the Skin”,Experimental Dermatology, vol. 13, pp. 567-591 (2004).
Kimball, et al., “Vanilloid receptor 1 antagonists attenuate disease severity in dextran sulphate sodium-induced colitis in mice”,Neurogastroenterol Motil, vol. 16, pp. 811-818 (2004).
Appendino, et al., “Halogenation of a capsaicin analogue leads to novel vanilloid TRPV1 receptor antagonists”,British Journal of Pharmacology, vol. 139, pp. 1417-1424 (2003).
Bölcskei, et al., “Investigation of the role of TRPV1 receptors in acute and chronic nociceptive processes using gene-deficient mice”,Pain, vol. 117, pp. 368-376 (2005).
Lee, et al., “Painful Channels in Sensory Neurons”,Molecules and Cells, vol. 20(3), pp. 315-324 (2005).
Hanazawa Takeshi
Hirano Misato
Inoue Tadashi
Nagayama Satoshi
Nakao Kazunari
Kispert Jennifer
Kumar Shailendra
Olson A. Dean
Pfizer Inc.
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