Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2007-07-25
2009-12-08
Wilson, James O (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S283000
Reexamination Certificate
active
07629351
ABSTRACT:
The present invention provides a novel antagonist or partial agonists/antagonist of MCP-1 receptor activity: N-((1R,2S,5R)-5-tert-butylamino)-2-((S)-2-oxo-3-(6-(trifluoromethyl)quinazolin-4-ylamino)pyrrolidin-1-yl)cyclohexyl)acetamide,or a pharmaceutically acceptable salt, solvate or prodrug, thereof, having an unexpected combination of desirable pharmacological characteristics. Crystalline forms of the present invention are also provided. Pharmaceutical compositions containing the same and methods of using the same as agents for the treatment of inflammatory diseases, allergic, autoimmune, metabolic, cancer and/or cardiovascular diseases is also an objective of this invention. The present disclosure also provides a process for preparing compounds of Formula (I), including N-((1R,2S,5R)-5-(tert-butylamino)-2-((S)-2-oxo-3-(6-trifluoromethyl)quinazolin-4-ylamino)pyrrolidin-1-yl)cyclohexyl)acetamide:wherein R1, R8,R9, R10, andare as described herein. Compounds that are useful intermediates of the process are also provided herein.
REFERENCES:
patent: 6706712 (2004-03-01), Cherney
patent: 6974836 (2005-12-01), Carter et al.
patent: 7087604 (2006-08-01), Cherney
patent: 7157470 (2007-01-01), Smallheer et al.
patent: 7163937 (2007-01-01), Carter et al.
patent: 7183270 (2007-02-01), Cherney et al.
patent: 7230133 (2007-06-01), Carter
patent: 2003/0171218 (2003-09-01), Bojack et al.
patent: 2004/0186143 (2004-09-01), Carter et al.
patent: 2004/0235836 (2004-11-01), Cherney
patent: 2005/0043392 (2005-02-01), Carter
patent: 2005/0054626 (2005-03-01), Carter et al.
patent: 2005/0054627 (2005-03-01), Carter et al.
patent: 2005/0065147 (2005-03-01), Carter
patent: 2006/0069123 (2006-03-01), Xia et al.
patent: 2007/0197516 (2007-08-01), Carter
patent: 0 550 924 (1993-07-01), None
patent: 63-83082 (1988-04-01), None
patent: WO 97/05111 (1997-02-01), None
patent: WO 97/43257 (1997-11-01), None
patent: WO 98/01426 (1998-01-01), None
patent: WO 99/00362 (1999-01-01), None
patent: WO 99/07678 (1999-02-01), None
patent: WO 99/37304 (1999-07-01), None
patent: WO 99/38844 (1999-08-01), None
patent: WO 99/40914 (1999-08-01), None
patent: WO 99/46991 (1999-09-01), None
patent: WO 01/10799 (2001-02-01), None
patent: WO 01/17992 (2001-03-01), None
patent: WO 02/04416 (2002-01-01), None
patent: WO 02/060859 (2002-08-01), None
patent: WO 02/078679 (2002-10-01), None
patent: WO 02/102372 (2002-12-01), None
patent: WO 03/005824 (2003-01-01), None
patent: WO 03/075853 (2003-09-01), None
patent: WO 2004/022536 (2004-03-01), None
patent: WO 2004/071460 (2004-08-01), None
patent: WO 2004/098516 (2004-11-01), None
patent: WO 2004/110376 (2004-12-01), None
patent: WO 2005/021500 (2005-03-01), None
patent: WO 2006/013427 (2006-02-01), None
Abbadie, C. et al., “Impaired neuropathic pain responses in mice lacking the chemokine receptor CCR2”, Proceedings of the National Academy of Sciences, vol. 100, No. 13, pp. 7947-7952 (2003).
Abdi, R. et al., “Differential Role of CCR2 in Islet and Heart Allograft Rejection: Tissue Specificity of Chemokine/Chemokine Receptor Function In Vivo”, The Journal of Immunology, vol. 172, pp. 767-775 (2004).
Andres, P.G. et al., “Mice with a Selective Deletion of the CC Chemokine Receptors 5 or 2 are Protected from Dextran Sodium Sulfate-Mediated Colitis: Lack of CC Chemokine Receptor 5 Expression Results in a NK1.1+Lymphocyte-Associated Th2-Type Immune Response in the Intestine”, The Journal of Immunology, vol. 164, pp. 6303-6312 (2000).
Antoniades, H.N. et al., “Expression of monocyte chemoattractant protein 1 mRNA in human idiopathic pulmonary fibrosis”, Proc. Natl. Acad. Sci. USA, vol. 89, pp. 5371-5375 (1992).
Baba, M. et al., “Identification of CCR6, the Specific Receptor for a Novel Lymphocyte-directed CC Chemokine LARC”, The Journal of Biological Chemistry, vol. 272, No. 23, pp. 14893-14898 (1997).
Belperio, J.A. et al., “Critical role for the chemokine MCP-1/CCR2 in the pathogenesis of bronchiolitis obliterans syndrome”, The Journal of Clinical Investigation, vol. 108, No. 4, pp. 547-556 (2001).
Berman, J.W. et al., “Localization of Monocyte Chemoattractant Peptide-1 Expression in the Central Nervous System in Experimental Autoimmune Encephalomyelitis and Trauma in the Rat”, The Journal of Immunology, vol. 156, pp. 3017-3023 (1996).
Bonini, J.A. et al., “Cloning, Expression, and Chromosomal Mapping of a Novel Human CC-Chemokine Receptor (CCR10) that Displays High-Affinity Binding for MCP-1 and MCP-3”, DNA and Cell Biology, vol. 16, No. 10, pp. 1249-1256 (1997).
Boring, L. et al., “Decreased lesion formation in CCR2-/-mice reveals a role for chemokines in the initiation of atherosclerosis”, Nature, vol. 394, pp. 894-897 (1998).
Boring, L. et al., “Impaired Monocyte Migration and Reduced Type 1 (Th1) Cytokine Responses in C-C Chemokine Receptor 2 Knockout Mice”, The Journal of Clinical Investigation, vol. 100, No. 10, pp. 2552-2561 (1997).
Brodmerkel, C.M. et al., “Discovery and Pharmacological Characterization of a Novel Rodent-Active CCR2 Antagonist, INCB3344”, The Journal of Immunology, vol. 175, pp. 5370-5378 (2005).
Brühl, H. et al., “Dual Role of CCR2 during Initiation and Progression of Collagen-Induced Arthritis: Evidence for Regulatory Activity of CCR2+T Cells”, The Journal of Immunology, vol. 172, pp. 890-898 (2004).
Bruun, J.M. et al., “Monocyte Chemoattractant Protein-1 Release is Higher in Visceral than Subcutaneous Human Adipose Tissue (AT): Implication of Macrophages Resident in the AT”, The Journal of Clinical Endocrinology & Metabolism, vol. 90, No. 4, pp. 2282-2289 (2005).
Bush, E. et al., “CC Chemokine Receptor 2 is Required for Macrophage Infiltration and Vascular Hypertrophy in Angiotensin II-Induced Hypertension”, Hypertension, vol. 36, pp. 360-363 (2000).
Carter, P.H., “Chemokine receptor antagonism as an approach to anti-inflammatory therapy: ‘just right’ or plain wrong?”, Current Opinion in Chemical Biology, vol. 6, pp. 510-525 (2002).
Charo, I.F. et al., “Molecular cloning and functional expression of two monocyte chemoattractant protein 1 receptors reveals alternative splicing of the carboxyl-terminal tails”, Proc. Natl. Acad. Sci. USA, vol. 91, pp. 2752-2756 (1994).
Charo, I.F. et al., “The Many Roles of Chemokines and Chemokine Receptors in Inflammation”, The New England Journal of Medicine, vol. 354, No. 6, pp. 610-621 (2006).
Chen, A. et al., “Diet Induction of Monocyte Chemoattractant Protein-1 and its Impact on Obesity”, Obesity Research, vol. 13, No. 8, pp. 1311-1320 (2005).
Chen, H., “Cellular inflammatory responses: Novel insights for obesity and insulin resistance”, Pharmacological Research, vol. 53, pp. 469-477 (2006).
Chow, F.Y. et al., “Monocyte chemoattractant protein-1-induced tissue inflammation is critical for the development of renal injury but not type 2 diabetes in obesedb/dbmice”, Diabetologia, vol. 50, pp. 471-480 (2007).
Cipollone, F. et al., “Elevated Circulating Levels of Monocyte Chemoattractant Protein-1 in Patients with Restenosis After Coronary Angioplasty”, Arterioscler. Thromb. Vasc. Biol., vol. 21, pp. 327-334 (2001).
Combadiere, C. et al., “Cloning and Functional Expression of a Human Eosinophil CC Chemokine Receptor”, The Journal of Biological Chemistry, vol. 270, No. 27, pp. 16491-16494 (1995).
Connor, R.I. et al., “Change in Coreceptor Use Correlates with Disease Progression in HIV-1-Infected Individuals”, J. Exp. Med., vol. 185, No. 4, pp. 621-628 (1997).
Connor, S.J. et al., “CCR2 expressing CD4+lymphocytes are preferentially recruited to the ileum in Crohn's disease”, Gut, vol. 53, pp. 1287-1294 (2004).
Conti, I. et al., “CCL2 (monocyte chemoattractant protein-1) and cancer”, Seminars in Cancer Biology, vol. 14, pp. 149-154 (2004).
Costain, W.J. et
Carter Percy H.
Duncia John V.
Mudryk Boguslaw M.
Randazzo Michael E.
Xiao Zili
Bogie Terence J.
Bristol--Myers Squibb Company
Duncan Laurelee A.
Willis Douglas M
Wilson James O
LandOfFree
N-((1R,2S,5R)-5-( tert... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with N-((1R,2S,5R)-5-( tert..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N-((1R,2S,5R)-5-( tert... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4136461