Thienopyrimidine-based inhibitors of the src family

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C544S278000

Reexamination Certificate

active

10399816

ABSTRACT:
Various thienopyrimidine-based analog compounds are able to selectively inhibit the Src family of tyrosine kinases. Compounds of the present invention, capable of such selective inhibition, are of the basic structure seen in formulae (I), (II) or (III):These compounds are useful in the treatment of a wide variety of diseases including hyperproliferative diseases, hematologic allergic/immunological diseases, or viral infections. Methods of synthesis of these compounds and their methods of inhibiting the Src family of tyrosine kinases are presented.

REFERENCES:
patent: 4146716 (1979-03-01), Cox et al.
patent: 4196207 (1980-04-01), Webber
patent: 4562193 (1985-12-01), Yamamoto et al.
patent: 4845097 (1989-07-01), Matsumoto et al.
patent: 5593997 (1997-01-01), Dow et al.
patent: 5639757 (1997-06-01), Dow et al.
patent: 5668140 (1997-09-01), Schaper et al.
patent: 5948911 (1999-09-01), Pamukcu et al.
patent: 6096749 (2000-08-01), Traxler et al.
patent: 6096750 (2000-08-01), Gangjee
patent: 2006/0004002 (2006-01-01), Thrash et al.
patent: 0356158 (1990-02-01), None
patent: 0447891 (1991-09-01), None
patent: 0452002 (1991-10-01), None
patent: 1116586 (2001-07-01), None
patent: 1057612 (1967-02-01), None
patent: 2042061 (1980-10-01), None
patent: WO88/08842 (1988-11-01), None
patent: WO95/19774 (1995-07-01), None
patent: WO96/14319 (1996-05-01), None
patent: WO97/09878 (1997-03-01), None
patent: WO97/13771 (1997-04-01), None
patent: WO97/29110 (1997-08-01), None
patent: WO99/24440 (1999-05-01), None
patent: WO 00/16766 (2000-03-01), None
patent: WO 01/04102 (2001-01-01), None
patent: WO 01/66099 (2001-09-01), None
Noble, M.E.M. et al, Science, vol. 303, pp. 1800-1805, 2004.
West, Anthony R., Solid State Chemistry and its Applications, Wiley, New York, 1988 pp. 358 & 365.
Vippagunta, S. R. et al, Advanced Drug Delivery Reviews, 48, pp. 3-26, 2001.
David J.W. Grant, “University of Minnesota—Twin Cities Campus College of Pharmacy, Annual Report”, [online] 1999, [retrieved on Feb. 13, 2003]. Retrieved from the Internet, <http://www.msi.umn.edu/general/Reports/ar99/departments/pharmacy.html>.
Hozien, Synthesis and Application of Some New Thienopyrimidine Derivatives as Antimicrobial Agents; Synthetic Communications, 26(20) , 33-37, (1996).
Barnekow, “Functional aspects of thec-srcgene,”Crit. Rev. Oncogen:, 1:277-292, 1989.
Bolen and Brugge, “Leukocyte protein tyrosine kinases: potential targets for drug discovery,”Annu Rev Immunol, 15:371-404, 1997.
Bolen et al., “Analysis of pp60c-srcin human colon carcinoma and normal human colon mucosal cells,”Oncogene Res, 1:149-168, 1987.
Bolen et al., “Increased pp60c-srctyrosyl activity in human neuroblastomas is associated with amino-terminal tyrosine phosphorylation of the src gene product,”Proc Natl Acad Sci82:7275-7279, 1985.
Briggs, et al., “Affinity of Src Family Kinase SH3 Domains for HIV Nef in Vitro Does Not Predict Kinase Activation by Nef in Vivo,”Biochemistry, 39(3):489-495, 2000.
Burke, Jr. et al., “Bicyclic compounds as ring constrained inhibitors of protein-tyrosine kinase p561ck,”J. Med Chem, 36:425-432, 1993.
Burke, Jr., “Protein-tyrosine kinase inhibitors,”Drugs of the Future17:119-131, 1992.
Burke, Jr., “Protein-tyrosine kinases: potential targets for anticancer drug design,”Stem Cells, 12:1-6, 1994.
Cartwright et al., “Activation of the pp60c-srcprotein kinase is an early event in colonic carcinogenesis,”Proc Natl Acad Sci USA, 87:558-562, 1990.
Chackalaparampil and Shalloway, “Altered phosphorylation and activation of pp60c-srcduring fibroblast mitosis,”Cell, 52:801-810, 1988.
Chang and Geahlen, “Protein-tyrosine kinase inhibition: mechanism-based discovery of anti-tumor agents,”J. Nat. Prod., 55:1529-1560, 1992.
Chen et al., “Structure-activity relationships in a series of 5-[(2,5-dihydroxybenzyl)amino]salicylate inhibitors of EGF-receptor-associated tyrosine kinase: importance of additional hydrophobic aromatic interactions,”J. Med. Chem., 37:845-859, 1994.
Choi, et al., “Role of Hck in the Pathogenesis of Encephalomyocarditis Virus-Induced Diabetes in Mice,”Journal of Virology, 75(4):1949-1957, 2001.
Collette and Olive, “Non-receptor protein tyrosine kinases as immune targets of viruses,”Immunology Today, 18:393-400. 1997.
Corey and Anderson, “Src-Related Protein Tyrosine Kinases in Hematopoiesis, ”Blood, 93:1-14, 1999.
Cushman et al., “Synthesis and evaluation of new protein-tyrosine kinase inhibitors. Part 1. Pyridine-containing stilbenes and amides,”Biorg. Med. Chem. Lett., 1:211-214, 1991.
Cushman et al., “Synthesis and evaluation of new protein-tyrosine kinase inhibitors. Part 2. Phenylhyrazones,”Biorg. Med. Chem. Lett., 1:215-218, 1991.
Cushman et al., “Synthesis and protein-tyrosine kinase inhibitory activities of flavonoid analogues,”J. Med. Chem., 34:798-806, 1991.
Dave et al., “Gould-Jacob type of reaction in the synthesis of thieno[3,2-e]pyrimido[1,2-c] pyrimidines: a comparison of classical heating vs solvent-free microwave irridation,”Heterocycles, 51:1819-1826, 1999.
Dow et al., “Identification of tricyclic analogs related to ellagic acid as potent/selective tyrosine kinase inhibitors,”J. Med. Chem., 37:2224-2231, 1994.
Dunant and Ballmer-Hofer, “Signaling by Src Family Kinases: Lessons Learnt from DNA Tumour Viruses,”Cell. Signal., 9:385-393, 1997.
Easmon et al., “Azinyl and Diazinyl Hydrazones derived from Aryl N-Heteroaryl Ketones: Synthesis and Antiproliferative Activity,”Journal of Medicinal Chemistry, American Chemical Society, 40:4420-4425, 1997.
Ellis et al., “Down-regulation of Vascular Endothelial Growth Factor in Human Colon Carcinoma Cell Line Transfected with an Antisense Expression Vector Specific for c-src,”J. Biol. Chem., 273:1052-1057, 1998.
Felsenfeld, et al., “Selective regulation of integrin-cytoskeleton interactions by the tyrosine kinase Src,”Nature Cell Biology, 1:200-205, 1999.
Fry et al., “A specific inhibitor of the epidermal growth factor receptor tyrosine kinase,”Science, 265:1093-1095, 1994.
Garcia et al., “Effect of herbimycin A on growth and pp60c-srcactivity in human colon tumor cell lines,”Oncogene, 6:1983-1991, 1991.
Hall et al., “Evidence thatc-srcis involved in the process of osteoclastic bone resorption,”Biochem. Biophys. Res. Commun., 199:1237-1244, 1994.
Hibbs and Dunn, “Lyn, a src-like tyrosine kinase,”Int J Biochem Cell Biol, 29:397-400, 1997.
Hozien et al., “Synthesis and Application of Some New Thienopyrimidine Derivatives as Antimicrobial Agents,”Synthetic Communications, 20:3733-3755, 1996.
Jessup and Gallick, “ The biology of colorectal carcinoma,”Curr Problems in Cancer, 16:263-328, 1992.
Katada et al., “Cytotoxic effects of NSL-1406, a new thienopyrimidine derivative, on leukocytes and osteoclasts,”Bioorg. Medic. Chem. Lett., 9:797-802, 1999.
Kitanaka et al., “Antisense src expression inhibits proliferation and erythropoietin-induced erythroid differentiation of K562 human leukemia cells,”Biochem Biophysic Res Commun, 201:1534-1540, 1994.
Klein and Schneider, “Activation of Src Family Kinases by Hepatitis B Virus HBx Protein and Coupled Signaling to Ras,”Mol Cell Biol, 17:6427-6436, 1997.
Lee et al., “Tau interacts with src-family non-receptor tyrosine kinases,”Journal of Cell Science, 111:3167-3177, 1998.
Luttrell et al., “Involvement of pp60c-srcwith two major signaling pathways in human breast cancer,”Proc Natl Acad Sci, 91:83-87, 1994.
Maquire et al., “A new series of PDGF receptor tyrosine kinase inhibitors: 3-substituted quinoline derivatives,”J. Med. Chem., 37:2129-2137, 1994.
Missbach et al., “Substituted 5, 7-Diphenyl-

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

Thienopyrimidine-based inhibitors of the src family does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Thienopyrimidine-based inhibitors of the src family, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Thienopyrimidine-based inhibitors of the src family will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3896294

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