1H-pyrrolo [2,3-D] pyrimidine derivatives and methods of use...

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

Reexamination Certificate

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C544S280000, C544S244000, C544S117000, C514S081000, C514S252160, C514S234500

Reexamination Certificate

active

10871732

ABSTRACT:
This invention generally relates to pyrazolo pyrimidine derivatives useful as inhibitors of short chain dehydrogenase/reductase (SDR) family of NAD(P)(H) dependent oxido-reductases. The invention further relates to pharmaceutical compositions and methods of preventing or treating disease with1H-Pyrrolo[2.3-d]pyrimidine derivatives. More specifically, the invention relates to a 1H-Pyrrolo[2.3-d]pyrimidine which is a compound of Formula I or II:or a pharmaceutically-acceptable salt or prodrug thereof;wherein:Y is N or CR5;Z is NR3R4, halo, H, OH, alkyl, alkyloxy, or haloalkyl; andR1ais indolyl, thiazolyl, benzyl, biphenylyl, thiophenyl, pyrrolyl, or phenyl,wherein said phenyl is substituted with at least one of OH, —NR3R4, —C(═O)NR6R7, —CN, NO2—C(═O)OH, —C(═O)O-alkyl, (C1-C4)alkyl, halo, haloalkyl or haloaryl; and wherein said indolyl, thiazolyl, benzyl, biphenylyl, thiophenyl, or pyrrolyl is optionally substituted with OH, —NR3R4, —C(═O)NR6R7, —CN, NO2, —C(═O)O—R3, (C1-C4)alkyl, halo, haloalkyl or haloaryl.

REFERENCES:
patent: 5593997 (1997-01-01), Dow et al.
patent: 6001839 (1999-12-01), Calderwood et al.
patent: 6383790 (2002-05-01), Shokat
patent: 6921763 (2005-07-01), Hirst et al.
patent: 2006/0235031 (2006-10-01), Arnold et al.
patent: 812366 (1959-04-01), None
patent: WO 93/22443 (1993-11-01), None
patent: WO 97/28161 (1997-08-01), None
patent: WO 98/41525 (1998-09-01), None
patent: WO 98/41525 (1998-09-01), None
patent: WO 00/17202 (2000-03-01), None
patent: 01/19829 (2001-03-01), None
patent: 03/020880 (2003-03-01), None
patent: WO 2005/097800 (2005-10-01), None
Widler, L.; Green, J.; Missbach, M.; Susa, M.; Altmann, E., Bioorganic & Medicinal Chemistry Letters, 11(6), 849-852 (English) 2001.
Wolff, Manfred E. “Burger's Medicinal Chemistry, 5ed, Part I”, John Wiley & Sons, 1995, pp. 975-977.
Banker, G.S. et al, “Modern Pharmaceutics, 3ed.”, Marcel Dekker, New York, 1996, p. 451 and 596.
Norio Miyaura and Akira Suzuki, Chem. Rev. 95(7) 1995, pp. 2457-2483.
Frazen, Robert, Can J. Chem., 78, 957-962 (2000).
Arnold et. al. (Bioorg. & Med. Chem. Lett., 2000; 10; 2167-2170).
Niswender, C. M. et al., “Protein Engineering of Protein Kinase A Catalytic Subunits Results in the Acquisition of Novel Inhibitor Sensitivity,”The Journal of Biological Chemistry, Aug. 9, 2002, 277(32), 28916-28922.
Andrews, R.C. et al., “Effects of the 11β-Hydroxysteroid Dehydrogenase Inhibitor Carbenoxolone on Insulin Sensitivity in Men with Type 2 Diabetes,”J. Clin. Endocrinol. Metab., 2003, 88(1), 285-291.
Barf, T. et al., “Arylsulfonamidothiazoles as a New Class of Potential Antidiabetic Drugs. Discovery of Potent and Selective Inhibitors of the 11β-Hydroxysteroid Dehydrogenase Type 1,”J. Med. Chem., 2002, 45(18), 3813-3815.
Barnes, P.J. et al., “Efficacy and Safety of Inhaled Corticosteroids in Asthma,”Am. Rev. Respir. Dis., 1993, 148, S1-26.
Bell, G. et al., “Glucokinase Mutations Insulin Secretion, and Diabetes Mellitus,”Annu. Rev. Physiol., 1996, 58, 171-186.
Bohren, K.M., et al., “Expression, Crystallization and Preliminary Crystallographic Analysis of Human Carbonyl Reductase,”J. Mol. Biol., 1994, 244, 659-664.
Cox, B. et al., “Human Colorectal Cancer Cells Efficiently Conjugate the Cyclopentenone Prostaglandin, Prostaglandin J2,to Glutathione,”Biochim. Biophys. Acta., 2002, 1584, 37-45.
Diederich, S. et al., “In the Search for Specific Inhibitors of Human 11β-Hydroxysteroid-Dehydrogenases (11β-HSDs): Chenodeoxycholic Acid Selectively Inhibits 11β-HSD-I,”Eur. J. Endocrinol., 2000, 142, 200-207.
Ding, S., et al., “A Combinatorial Scaffold Approach toward Kinase-Directed Heterocycle Libraries,”J. Am. Chem. Soc., 2002, 124(8), 1594-1596.
Ding, S., et al., “Resin-Capture and Release Strategy toward Combinatorial Libraries of 2,6,9-Substituted Purines,”J. Comb. Chem., 2002, 4, 183-186.
Ding, S., et al., “A Concise and Traceless Linker Strategy toward Combinatorial Libraries of 2,6,9-Substituted Purines,”J. Org. Chem., 2001, 66, 8273-8276.
Fajans S. et al., “Maturity Onset Diabetes of the Young (MODY),”Diabet. Med., 1996, 13, S90-S95.
Feinstein, M.B. et al., “Regulation of the Action of Hydrocotisone in Airway Epithelial Cells by 11β-Hydroxysteroid Dehydrogenase,”Am. J. Respir. Cell. Mol. Biol., 1999, 21, 403-408.
Fingl E. et al., “General Principles,”The Pharmacological Basis of Therapeutics, Fifth Edition, 1975, Ch. 1, 1-46.
Forrest, G. L. et al., “Induction of a Human Carbonyl Reductase Gene Located on Chromosome 21,”Biochim. Biophys. Acta, 1990, 1048, 149-155.
Forrest, G.L. et al., “Carbonyl Reductase,”Chem. Biol. Interact., 2000, 129, 21-40.
Funder, J.W., et al., “Mineralocorticoid Action: Target Tissue Specificity Is Enzyme, Not Receptor, Mediated,”Science, 1988, 242, 583-585.
Garber, M.E. et al., “Diversity of Gene Expression in Adenocarcinoma of the Lung,”Proc. Nat. Acad. Sci. USA, 2001, 98(24), 13784-13789.
Gonzalez, B. et al., “Protection against Daunorubicin Cytotoxicity by Expression of a Cloned Human Carbonyl Reductase cDNA in K562 Leukemia Cells,”Cancer Res., 1995, 55, 4646-4650.
Haase, A. et al., “Detection of Viral Nucleic Acids by in Situ Hybridization,”Methods in Virology, 1984, vol. VII, 189-226.
Hanefeld, U. et al., “One-pot Synthesis of Tetrasubstituted Pyrazoles Proof of Regiochemistry,”J. Chem. Soc. Perkin Trans., 1996, 1, 1545-1552.
Ishiyama, T. et al., “Mild Iridium-Catalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and Isolation of a Potential Intermediate,”J. Am. Chem. Soc., 2002, 124(3), 390-391.
Ishiyama, T. et al., “A Stoichiometric Aromatic C-H Borylation Catalyzed by Iridium(I)/2,2′-Bipyridine Complexes at Room Temperature,”Angew. Chem. Int. Ed., 2002, 41(16), 3056-3058.
Kallberg, Y. et al., “Short-Chain Dehydrogenases/Reductases (SDRs)”Eur. J. Biochem., 2002, 269, 4409-4417.
Kallberg, Y. et al., “Short-Chain Dehydrogenase/Reductase (SDR) Relationships: a Large Family with Eight Clusters Common to Human, Animal, and Plant Genomes,”Protein Sci., 2002, 11, 636-641.
Kwok, B.H. et al., “The Anti-Inflammatory Natural Product Parthenolide from the Medicinal Herb Feverfew Directly Binds to and Inhibits IκB Kinase,”Chem. Biol., 2001, 8, 759-766.
Mayer, T.U. et al., “Small Molecule Inhibitor of Mitotic Spindle Bipolarity Identified in a Phenotype-Based Screen,”Science, 1999, 286, 971-974.
Moon, H.S. et al., “A Novel Microtubule Destabilizing Entity from Orthogonal Synthesis of Triazine Library and Zebrafish Embryo Screening,”J. Am. Chem. Soc., 2002, 124, 11608-11609.
Nakanishi, M. et al., “Cloning and Sequence Analysis of a cDNA Encoding Tetrameric Carbonyl Reductase of Pig Lung,”Biochem. Biophys. Acta, 1993, 194(3), 1311-1316.
Nobel, C.S.I. et al., “Purification of Full-Length Recombinant Human and Rat Type 1 11β-hydroxysteroid Dehydrogenases with Retained Oxidoreductase Activities,”Protein Expr. Purif., 2002, 26, 349-356.
Oppermann, U.C. et al., “Forms and Functions of Human SDR Enzymes,”Chem. Biol. Interact., 2001, 130-132(1-3), 699-705.
Persson, C.G., “Glucocorticoids for Asthma—Early Contributions,”Pulm. Pharmacol., 1989, 2, 163-166.
Pudlo, J.S. et al., “Synthesis, Antiproliferative, and Antiviral Activity of Certain 4-Substituted and 4,5 Disubstituted 7-[(1,3-Dihydroxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidines,”J. Med. Chem., 1990, 33, 1984-1992.
Robertson, R.P., “Eicosandoids and Human Disease,”Harrison's Principles of Internal Medicine, Isselbacher K. J. et al. (

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