Process for preparing pyrrolotriazine aniline compounds...

Details Process for preparing pyrrolotriazine aniline compounds... Process for preparing pyrrolotriazine aniline compounds...

2006-12-12

2006-12-12

Balasubramanian, Venkataraman (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C514S243000

Reexamination Certificate

active

07148348

ABSTRACT:
A process is provided for the process for preparing a pyrrolotriazine aniline p38 kinase inhibitor such as amide IIby the direct aminolysis of the ester Iwherein ester I is reacted with a strong organometallic base, such as hexyllithium or n-butyllithium and the desired amine such as n-propylamine to form the amide II.

REFERENCES:
patent: 4200750 (1980-04-01), Warner, Jr. et al.
patent: 4908056 (1990-03-01), Tseng
patent: 5658903 (1997-08-01), Adams et al.
patent: 5686457 (1997-11-01), Traxler et al.
patent: 5932576 (1999-08-01), Anantanarayan et al.
patent: 5945418 (1999-08-01), Bemis et al.
patent: 5977103 (1999-11-01), Adams et al.
patent: 6087496 (2000-07-01), Anantanarayan et al.
patent: 6130235 (2000-10-01), Mavunkel et al.
patent: 6147080 (2000-11-01), Bemis et al.
patent: 6251914 (2001-06-01), Adams et al.
patent: 6277989 (2001-08-01), Chakravarty et al.
patent: 6518269 (2003-02-01), Camden et al.
patent: 6589947 (2003-07-01), Hamanaka et al.
patent: 6670357 (2003-12-01), Leftheris et al.
patent: 6867300 (2005-03-01), Godfrey, Jr. et al.
patent: 6869952 (2005-03-01), Bhide et al.
patent: 6900217 (2005-05-01), Chen
patent: 6906067 (2005-06-01), Moriarty et al.
patent: 6908916 (2005-06-01), Mastalerz et al.
patent: 6916815 (2005-07-01), Vite et al.
patent: 6933386 (2005-08-01), Bhide et al.
patent: 6951859 (2005-10-01), Bhide et al.
patent: 6962915 (2005-11-01), Das et al.
patent: 6969717 (2005-11-01), Bhide et al.
patent: 6982265 (2006-01-01), Hunt et al.
patent: 2001/0041673 (2001-11-01), Fossa
patent: 2002/0065270 (2002-05-01), Moriarty et al.
patent: 2003/0139435 (2003-07-01), Ahmed et al.
patent: 2003/0232831 (2003-12-01), Dyckman et al.
patent: 2003/0232832 (2003-12-01), Lombardo et al.
patent: 2004/0082582 (2004-04-01), Dyckman et al.
patent: 2004/0157846 (2004-08-01), Chen et al.
patent: 2004/0229877 (2004-11-01), Leftheris et al.
patent: 2005/0043306 (2005-02-01), Leftheris et al.
patent: 2005/0124621 (2005-06-01), Bhide et al.
patent: 2005/0143398 (2005-06-01), Das et al.
patent: 2005/0182058 (2005-08-01), Fink et al.
patent: 2005/0197339 (2005-09-01), Gavai
patent: 2005/0209454 (2005-09-01), Swaminathan et al.
patent: 2005/0245530 (2005-11-01), Borzilleri et al.
patent: 2006/0003967 (2006-01-01), Shi et al.
patent: 2006/0004006 (2006-01-01), Borzilleri et al.
patent: 2006/0009454 (2006-01-01), Cai et al.
patent: 2006/0014745 (2006-01-01), Gavai et al.
patent: 2006/0019928 (2006-01-01), Lin et al.
patent: 0 713 876 (1996-05-01), None
patent: 0 795 556 (1997-09-01), None
patent: 0 778 277 (2003-06-01), None
patent: WO 98/08847 (1998-03-01), None
patent: WO 99/24033 (1999-05-01), None
patent: WO 00/12074 (2000-03-01), None
patent: WO 00/12497 (2000-03-01), None
patent: WO 00/20402 (2000-04-01), None
patent: WO 00/56738 (2000-09-01), None
patent: WO 00/71129 (2000-11-01), None
patent: WO 01/14378 (2001-03-01), None
patent: WO 01/27089 (2001-04-01), None
patent: WO 01/34605 (2001-05-01), None
patent: WO 01/47897 (2001-07-01), None
patent: WO 02/40486 (2002-05-01), None
patent: WO 03/002542 (2003-01-01), None
patent: WO 03/002544 (2003-01-01), None
patent: WO 03/042172 (2003-05-01), None
patent: WO 03/091229 (2003-11-01), None
patent: WO 2003/090912 (2003-11-01), None
patent: WO 2003/090912 (2003-11-01), None
patent: WO 03/099286 (2003-12-01), None
patent: WO 2004/009542 (2004-01-01), None
patent: WO 2004/009601 (2004-01-01), None
patent: WO 2004/009784 (2004-01-01), None
patent: WO 2004/013145 (2004-02-01), None
patent: WO 2004/043912 (2004-05-01), None
patent: WO 2004/054514 (2004-07-01), None
patent: WO 2004/072030 (2004-08-01), None
patent: WO 2005/042537 (2005-05-01), None
patent: WO 2005/058245 (2005-06-01), None
patent: WO 2005/065266 (2005-07-01), None
patent: WO 2005/066176 (2005-07-01), None
Chemical Abstracts, vol. 88, No. 121113q, p. 541 (1978).
Connolly, D.T. et al., “Human Vascular Permeability Factor”, The Journal of Biological Chemistry, vol. 264, No. 33, pp. 20017-20024 (1989).
Cullinan-Bove, K. et al., “Vascular Endothelial Growth Factor/Vascular Permeability Factor Expression in the Rat Uterus: Rapid Stimulation by Estrogen-Induced Increases in Uterine Capillary Permeability and Growth”, Endocrinology, vol. 133, No. 2, pp. 829-837 (1993).
de Vries, C. et al., “Thefms-Like Tyrosine Kinase, a Receptor for Vascular Endothelial Growth Factor”, Science, vol. 255, pp. 989-991 (1992).
Eskins, F., “Angiogenesis inhibitors in clinical development; where are we now and where are we going?”, British Journal of Cancer, vol. 90, No. 1, pp 1-7 (2004).
Ewald, H. et al., “Reactions of 1,2,4-Triazines with Dimethyl Acetylenedicarboxylate”, Liebigs Ann. Chem., pp. 1718-1724 (1977).
Fabbro, D. et al., “Protein kinases as targets for anticancer agents: from inhibitors to useful drugs”, Pharmacology & Therapeutics, vol. 93, pp. 79-98 (2002).
Fan, T.-P.D. et al., “Controlling the vasculature: angiogenesis, antiangiogenesis and vascular targeting of gene therapy”, Trends in Pharmacological Sciences, vol. 16, pp. 57-66 (1995).
Folkman, J., “Angiogenesis in cancer, vascular rheumatoid and other disease”, Nature Medicine, vol. 1, No. 1, pp. 27-31 (1995).
Haque, S.A. et al., “Monastrol, a Prototype Anti-Cancer Drug That Inhibits a Mitotic Kinesin, Induces Rapid Bursts of Axonal Outgrowth From Cultured Postmitotic Neurons”, Cell Motility and the Cytoskeleton, vol. 58, pp. 10-16 (2004).
Henry, J.R. et al., “p38 mitogen-activated protein kinase as a target for drug discovery”, Drugs of the Future, vol. 24, No. 12, pp. 1345-1354 (1999).
Jaffari, G.A. et al., “Some Oxidation Reactions of Monochloramine”, J. Chem. Soc. (C), pp. 823-826 (1971).
Jakeman, L.B. et al., “Development Expression of Binding Sites and Messenger Ribonucleic Acid for Vascular Endothelial Growth Factor Suggests a Role for This Protein in Vasculogenesis and Angiogenesis”, Endocrinology, vol. 133, No. 2, pp. 848-859 (1993).
Kapoor, T.M. et al., “Probing Spindle Assembly Mechanisms with Monastrol, a Small Molecule Inhibitor of the Mitotic Kinesin, Eg5”, The Journal of Cell Biology, vol. 150, No. 5, pp. 975-988 (2000).
Kolch, W. et al., “Regulation of the expression of the VEGF/VPS and its receptors: role in tumor angiogenesis”, Breast Cancer Research and Treatment, vol. 36, pp. 139-155 (1995).
Mayer, T.U. et al., “Small Molecule Inhibitor of Mitotic Spindle Bipolarity Identified in a Phenotype-Based Screen”, Science, vol. 286, pp. 971-974 (1999).
Migliara, O. et al., “Synthesis of a New Bridgehead Nitrogen Heterocyclic System. Pyrrolo[2,1-f]-1,2,4-triazine Derivatives”, J. Heterocyclic Chem., vol. 16, pp. 833-834 (1979).
Moreland, L.W. et al., “Etanercept Therapy in Rheumatoid Arthritis: A Randomized, Controlled Trial”, Ann. Intern. Med., vol. 130, No. 6, pp. 478-486 (1999).
Neunhoeffer, H. et al., “Cycloaddition Reactions with Methoxy- and Dialkylamino-1,2,4-triazines”, Liebigs Ann. Chem., pp. 1413-1420 (1977).
Otter, B.A. et al., “Conformational Properties of Purine-Like C-Nucleosides”, Nucleosides & Nucleotides, vol. 15, Nos. 1-3, pp. 793-807 (1996).
Patil, S.A. et al., “Synthesis of Pyrrolo[2,1-f][1.2.4]triazine Congeners of Nucleic Acid Purines via the V-Amination of 2-Substituted Pyrroles”, J. Heterocyclic Chem., vol. 31, pp. 781-786 (1994).
Quintela, J.M. et al., “A Ready One-pot Preparation for Pyrrolo[2,1-f][1,2,4]triazine and Pyrazolo[5,1-c]pyrimido[4,5-e][1,2,4]triazine Derivatives”, Tetrahedron, vol. 52, no. 8, pp. 3037-3048 (1996).
Raingeaud, J. et al., “MKK3- and MKK6-Regulated Gene Expression is Mediated by the p38 Mitogen-Activated Protein Kinase Signal Transduction Pathway”, Molecular and Cellular Biology, vol. 16, No. 3, pp. 1247-1255 (1996).
Rankin, E.C.C. et al., “The Therapeutic Effects of an Engineered Human AntiTumor Necrosis Factor Alpha Antibody (CDP571) in Rheumatoi

Affiliated with

Also associated with

Rating

Process for preparing pyrrolotriazine aniline compounds... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing pyrrolotriazine aniline compounds..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing pyrrolotriazine aniline compounds... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3658451