N-aryl pyrazoles, indazoles and azaindazoles as antagonists of CC chemokine receptor 1: Patent cooperation treaty applications WO2010/036632, WO2009/134666 and WO2009/137338

Expert Opinion on Therapeutic Patents

Volumn 20, Issue 11, 2010, Pages 1609-1618

  Carter, Percy H ^a   Hynes, John ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

CCR1; chemokine; GPCR; indazoles; inflammation; MS; pyrazoles; rheumatoid arthritis

Indexed keywords

1 (4 FLUOROPHENYL) 1H PYRAZOLO[3,4 C]PYRIDINE 4 CARBOXYLIC ACID [1 (2 METHANESULFONYLPYRIDIN 4 YL)PROPYL]AMIDE; 6 CYANO 1 (4 FLUOROPHENYL) 1H INDAZOLE 4 CARBOXYLIC ACID 4 METHYLSULFAMOYLBENZYLAMIDE; 6 CYANOINDAZOLE; AZAINDAZOLE; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CCR1; INDAZOLE DERIVATIVE; MACROPHAGE INFLAMMATORY PROTEIN 1ALPHA; N ARYLPYRAZOLE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

BINDING AFFINITY; CALCIUM TRANSPORT; CELL ACTIVATION; CELL MIGRATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; INFLAMMATORY DISEASE; LEUKOCYTE; MULTIPLE SCLEROSIS; NONHUMAN; REVIEW; RHEUMATOID ARTHRITIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ARTHRITIS, RHEUMATOID; CALCIUM; DISEASE MODELS, ANIMAL; HUMANS; INDAZOLES; INFLAMMATION; LEUKOCYTES; MULTIPLE SCLEROSIS; PATENTS AS TOPIC; PYRAZOLES; RECEPTORS, CCR1; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77958457972     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.2010.518144     Document Type: Review

References (36)

1. Gaga M, Ong YE, Benyahia F, et al. Skin reactivity and local cell recruitment in human atopic and nonatopic subjects by CCL2/MCP-1 and CCL3/MIP-1alpha. Allergy 2008;63:703-11
2. Lee SC, Brummet ME, Shahabuddin S, et al. Cutaneous injection of human subjects with macrophage inflammatory protein-1 alpha induces significant recruitment of neutrophils and monocytes. J Immunol 2000;164:3392-401
3. Allen SJ, Crown SE, Handel TM. Chemokine:receptor structure, interactions, and antagonism. Annu Rev Immunol 2007;25:787-820
4. Sallusto F, Baggiolini M. Chemokines and leukocyte traffic. Nat Immunol 2008;9:949-52
5. Viola A, Luster AD. Chemokines and their receptors: drug targets in immunity and inflammation. Annu Rev Pharmacol Toxicol 2008;48:171-97
6. Horuk R. Chemokine receptor antagonists: overcoming developmental hurdles. Nat Rev Drug Discov 2009;8:23-33
7. Carson KG, Jaffee BD, Harriman GCB. CCR1 antagonists. Annu Rep Med Chem 2004;39:149-58
8. Pease JE, Horuk R CCR1 antagonists in clinical development. Expert Opin Investig Drugs 2005;14:785-96
9. Carter PH. Chemokine receptor antagonism as an approach to anti-inflammatory therapy: 'just right' or plain wrong? Curr Opin Chem Biol 2002;6:510-25
10. Gao Z, Metz WA. Unraveling the chemistry of chemokine receptor ligands. Chem Rev 2003;103:3733-52
11. Schwarz MK, Wells TN. New therapeutics that modulate chemokine networks. Nat Rev Drug Discov 2002;1:347-58
12. Pease JE, Horuk R Chemokine receptor antagonists: Part 1. Expert Opin Ther Pat 2009;19:39-58
13. Pease JE, Horuk R Chemokine receptor antagonists: Part 2. Expert Opin Ther Pat 2009;19:199-221
14. Zipp F, Hartung HP, Hillert J, et al. CCR1 Antagonist Study Group. Blockade of chemokine signaling in patients with multiple sclerosis. Neurology 2006;67:1880-3
15. Kerstjens HA, Bjermer L, Eriksson L, et al. Tolerability and efficacy of inhaled AZD4818, a CCR1 antagonist, in moderate to severe COPD patients. Respir Med 2010;104:1297-303
16. Norman P. AZD-4818, a chemokine CCR1 antagonist: WO2008103126 and WO2009011653. Expert Opin Ther Pat 2009;19:1629-33
17. Haringman JJ, Kraan MC, Smeets TJ, et al. Chemokine blockade and chronic inflammatory disease: proof of concept in patients with rheumatoid arthritis. Ann Rheum Dis 2003;62:715-21
18. Borregaard J, Skov L, Wang L, et al. Evaluation of the effect of the specific CCR1 antagonist CP-481715 on the clinical and cellular responses observed following epicutaneous nickel challenge in human subjects. Contact Dermatitis 2008;59:212-19
19. Lu C; Balani SK, Qian MG, et al. Quantitative prediction and clinical observation of a CYP3A inhibitor-based drug-drug interactions with MLN3897, a potent C-C chemokine receptor-1 antagonist. J Pharmacol Exp Ther 2010;332:562-8
20. Vergunst CE, Gerlag DM, von Moltke L, et al. MLN3897 plus methotrexate in patients with rheumatoid arthritis: safety, efficacy, pharmacokinetics, and pharmacodynamics of an oral CCR1 antagonist in a phase IIa, double-blind, placebo-controlled, randomized, proof-of-concept study. Arthritis Rheum 2009;60:3572-81
21. Chemocentryx, Inc. Preparation of pyrazolopyridylacetylpiperazinylbenzenes as CCR1 chemokine receptor antagonists. WO2008147822; 2008
22. Chemocentryx, Inc. Preparation of 3-imidazolylpyrazolo[3,4-b]pyridines as chemokine binding inhibitors. WO2008147815; 2008
23. Chemocentryx, Inc. Preparation of 4-amino-3-(imidazolyl)pyrazolo[3,4-d] pyrimidines as CCR1 chemokine receptor antagonists. WO2010030815; 2010
24. Boehringer Ingelheim International GMBH. Pyrazole compounds as CCR1 antagonists. WO2009137338; 2009
25. Boehringer Ingelheim International GMBH. Indazole compounds as CCR1 antagonists. WO2009134666; 2009
26. Boehringer Ingelheim International GMBH. Azaindazole compounds as CCR1 antagonists. WO2010036632; 2010
27. Tanuwidjaja J, Peltier HM, Ellman JA. One-pot asymmetric synthesis of either diastereomer of tert-butanesulfinyl-protected amines from ketones. J Org Chem 2007;72:626-9, and references cited therein
28. Vistoli G, Pedretti A, Testa B. Assessing drug-likeness-what are we missing? Drug Discov Today 2008;13:285-94
29. Kromdijk W, Huitema AD, Mulder JW. Treatment of HIV infection with the CCR5 antagonist maraviroc. Expert Opin Pharmacother 2010;11:1215-23
30. Cashen AF. Plerixafor hydrochloride: a novel agent for the mobilization of peripheral blood stem cells. Drugs Today (Barc) 2009;45:497-505
31. Eksteen B, Adams DH. GSK-1605786, a selective small-molecule antagonist of the CCR9 chemokine receptor for the treatment of Crohn's disease. IDrugs 010;13:472-81
32. Carter PH, Zhao Q. Clinically validated approaches to the treatment of autoimmune diseases. Expert Opin Investig Drugs 2010;19:195-213
33. Isaacs JD. The changing face of rheumatoid arthritis: sustained remission for all? Nat Rev Immunol 2010;10:605-11
34. Vergunst CE, Gerlag DM, Lopatinskaya L, et al. Modulation of CCR2 in rheumatoid arthritis: a double-blind, randomized, placebo-controlled clinical trial. Arthritis Rheum 2008;58:1931-9
35. Gerlag DM, Hollis S, Layton M, et al. Preclinical and clinical investigation of a CCR5 antagonist, AZD5672, in patients with rheumatoid arthritis receiving methotrexate. Arthritis Rheum 2010. [Epub ahead ofprint]
36. van Kuijk AW, Vergunst CE, Gerlag DM, et al. CCR5 blockade in rheumatoid arthritis: a randomised, double-blind, placebo-controlled clinical trial. Ann Rheum Dis 2010. [Epub aheadofprint]