Quinolones and azaquinolones that inhibit prolyl hydroxylase

Details Quinolones and azaquinolones that inhibit prolyl hydroxylase Quinolones and azaquinolones that inhibit prolyl hydroxylase

2008-04-16

2011-11-01

Ward, Paul V. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S112000, C546S152000

Reexamination Certificate

active

08048894

ABSTRACT:
Compounds of Formula I are useful inhibitors of HIF prolyl hydroxylases. Compounds of Formula I have the following structure:where the definitions of the variables are provided herein.

REFERENCES:
patent: 3954733 (1976-05-01), Tobiki et al.
patent: 3992371 (1976-11-01), Tobiki et al.
patent: 4215123 (1980-07-01), Scotese et al.
patent: 4374138 (1983-02-01), Haskell et al.
patent: 4382089 (1983-05-01), Haskell et al.
patent: 4404201 (1983-09-01), Haskell et al.
patent: 4468394 (1984-08-01), Machida et al.
patent: 4710473 (1987-12-01), Morris
patent: 5037826 (1991-08-01), Blythin et al.
patent: 5126341 (1992-06-01), Suzuki et al.
patent: 5378679 (1995-01-01), Nuebling et al.
patent: 5502035 (1996-03-01), Haviv et al.
patent: 5620995 (1997-04-01), Weidmann et al.
patent: 5719164 (1998-02-01), Weidmann et al.
patent: 5798451 (1998-08-01), von Deyn et al.
patent: 5972841 (1999-10-01), von Deyn et al.
patent: 6093730 (2000-07-01), Weidmann et al.
patent: 6593343 (2003-07-01), Björk et al.
patent: 6787326 (2004-09-01), Ratcliffe et al.
patent: 2003/0153503 (2003-08-01), Klaus et al.
patent: 2004/0235082 (2004-11-01), Fourney et al.
patent: 2004/0254215 (2004-12-01), Arend et al.
patent: 2005/0020487 (2005-01-01), Klaus et al.
patent: 2005/0107364 (2005-05-01), Hutchinson et al.
patent: 2006/0216295 (2006-09-01), Crabtree et al.
patent: 2006/0251638 (2006-11-01), Guenzler-Pukall et al.
patent: 2006/0276477 (2006-12-01), Klaus et al.
patent: 2007/0004627 (2007-01-01), Seeley et al.
patent: 2007/0203174 (2007-08-01), Klimko et al.
patent: 2007/0249605 (2007-10-01), Allen et al.
patent: 2008/0171756 (2008-07-01), Shaw et al.
patent: 2009/0082357 (2009-03-01), Fitch et al.
patent: 328085 (1976-03-01), None
patent: 0 500 297 (1992-08-01), None
patent: 0 503 844 (1992-09-01), None
patent: 0 937 459 (1999-08-01), None
patent: 0 547 708 (2003-02-01), None
patent: 1 541 558 (2003-08-01), None
patent: 1 538 160 (2005-06-01), None
patent: 1 449 256 (1976-09-01), None
patent: 493592 (1974-04-01), None
patent: 7224040 (1995-08-01), None
patent: 1735288 (1992-05-01), None
patent: WO 01/85732 (2001-11-01), None
patent: WO 02/24679 (2002-03-01), None
patent: WO 02/076396 (2002-10-01), None
patent: WO 03/053997 (2003-07-01), None
patent: WO 2004/037853 (2004-05-01), None
patent: WO 2004/103974 (2004-12-01), None
patent: WO 2004/104000 (2004-12-01), None
patent: WO 2004/108121 (2004-12-01), None
patent: WO 2004/108681 (2004-12-01), None
patent: WO 2005/011696 (2005-02-01), None
patent: WO 2005/021546 (2005-03-01), None
patent: WO 2005/047285 (2005-05-01), None
patent: WO 2005/077050 (2005-08-01), None
patent: WO 2005/111044 (2005-11-01), None
patent: WO 2006/088246 (2006-08-01), None
patent: WO 2006/094292 (2006-09-01), None
patent: WO 2007/038571 (2007-04-01), None
patent: WO 2007/070359 (2007-06-01), None
patent: WO 2007/097929 (2007-08-01), None
patent: WO 2007/103905 (2007-09-01), None
patent: WO 2007/136990 (2007-11-01), None
patent: WO 2007/150011 (2007-12-01), None
patent: WO 2008/040002 (2008-04-01), None
U.S. Appl. No. 12/002,537, filed Dec. 17, 2007, Allen et al.
U.S. Appl. No. 12/002,538, filed Dec. 17, 2007, Allen et al.
U.S. Appl. No. 12/082,263, filed Apr. 9, 2008, Allen et al.
U.S. Appl. No. 12/150,675, filed Apr. 29, 2008, Allen et al.
U.S. Appl. No. 12/150,998, filed May 2, 2008, Allen et al.
International Search Report co-pending PCT Application No. PCT/US2008/004965 (WO 2008/130600 A3 cover page and ISR) published on Oct. 30, 2008.
He, L. et al., “Probabilistic Neural Network Multiple Classifier System for Predicting the Genotoxicity of Quinolones and Quinoline Derivatives,” Chem. Res. Toxicol. 18, pp. 428-440 (2005).
Ukrainets, I.V. et al., “4-Hydroxy-2-Quinolines. XXI. 1H-2-Oxo-4-Hydroxyquinoline-3-Carboxylic Alkylamides as a Novel Group of Antithyroid Drugs,” Farmatsevtichnii Zhurnal (Kiev) 6, pp. 54-55 (1995).
Bezuglyi, P.A., “Amides of 4-Hydroxyquinoline-2-oxo-3-carboxylic Acid: Synthesis and Anticoagulant Activity,” Khimiko-Farmatsevticheskii Zhurnal, 24(4) pp. 31-32 (1990). This document is in the Russian language—an English language abstract is included.
Schofield, C.J. et al., “Oxygen Sensing by HIF Hydroxylases”, Nature Reviews, Molecular Cell Biology, 5(5), pp. 243-254 (2004).
McDowell, R. S. et al., “From Peptide to Non-Peptide. 2. The De Novo Design of Potent, Non-peptidal Inhibitors of Platelet Aggregation Based on a Benzodiazepinedione Scaffold,” J. Am. Chem. Soc. 116(12) pp. 5077-5083 (1994).
Bohnert et al., “Redox Reactions with Cyclopeptide-Like Quinoline Derivatives as Lipophilic, Masked NAD Model Compounds,” Zeitschrift für Naturforschung, B.: Chemical Sciences, 42(9) pp. 1159-1166 (1987). This document is in the German language—an English language abstract is included.
Kath, J.C. et al., Potent Small Molecule CCR1 Antagonists, Bioorg & Med. Chem. Letters, 14(9), pp. 2169-2173 (2004).
Ukrainets, I.V. et al., “4-Hydroxy-2-Quinolones. 4. Selection of the Optimum Path for Synthesis of N-R-Substituted 4-Hydroxy-2-Quinolone-3-Carboxylic Acid Amides.” Chemistry of Heterocyclic Compounds 28(5), pp. 538-540 (1992).
Warshakoon, N. C. et al., “Design and Synthesis of a Series of Novel Pyrazolopyridines as HIF 1-α Prolyl Hydroxylase Inhibitors,” Bioorg & Med. Chem. Letters, 16, pp. 5687-5690 (2006).
Warshakoon, N. C. et al., “Structure-Based Design, Synthesis, and SAR Evaluation of a New Series of 8-Hydroxyquinolinse as HIF-1α Prolyl Hydroxylase Inhibitors,” Bioorg & Med. Chem. Letters, 16, pp. 5517-5522 (2006).
Warshakoon, N. C. et al., “A Novel Series of Imidazo[1,2-a]pyridine Derivatives as HIF-1α Prolyl Hydroxylase Inhibitors,” Bioorg & Med. Chem. Letters, 16, pp. 5598-5601 (2006).
McDonough, M.A. et al., “Cellular Oxygen Sensing: Crystal Structure of Hypoxia-Inducible Factor Prolyl Hydroxylase (PHD2),” Proc. Natl. Acad. Sci., 103(26) pp. 9814-9819 (2006).
Jönssen, S. et al., “Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Diorders: Structure-Activity Relationship,” J. Med. Chem. 47, pp. 2075-2088 (2004).
Buckle, D.R. et al., “Synthesis and Antiallergic Activity of 2-Hydroxy-3-nitro-1,4-naphthoquinones,” J. Med. Chem. 20(8), pp. 1059-1064 (1977).
Franklin, T.J. et al., “Approaches to the Design of Anti-Fibrotic Drugs,” Biochem. Soc. Trans. 19, pp. 812-815 (1991).
Vippagunta, S.R. et al. “Crystalline Solids,” Advanced Drug Delivery Reviews, 48, pp. 3-26 (2001).
Lala, P. K. et al. “Role of nitric oxide in tumor progression: Lessons from experimental tumors,” Cancer and Metastasis Reviews, 17, pp. 91-106, (1998).
Golub, T. R. et al. “Molecular Classification of Cancer: Class Discovery and Class Prediction by Gene Expression Monitoring”, Science, 286, pp. 531-537 (1999).
Prosecution History of U.S. Appl. No. 12/002,538 Without Cited References, From Dec. 17, 2007 to Jun. 17, 2011.
Prosecution History of U.S. Appl. No. 11/635,683 Without Cited References, From Dec. 8, 2006 to Aug. 2, 2010.
Prosecution History of U.S. Appl. No. 12/703,496 Without Cited References, From Feb. 10, 2010 to May 16, 2011.
Prosecution History of U.S. Appl. No. 12/703,716 Without Cited References, From Feb. 10, 2010 to May 17, 2011.
Prosecution History of U.S. Appl. No. 12/002,537 Without Cited References, From Dec. 17, 2007 to Dec. 22, 2009.
Prosecution History of U.S. Appl. No. 12/612,465 Without Cited References, From Nov. 4, 2009 to Apr. 19, 2011.
Prosecution History of U.S. Appl. No. 12/082,263 Without Cited References, From Apr. 9, 2008 to Aug. 4, 2009.
Prosecution History of U.S. Appl. No. 13/109,877 Without Cited References, From May 17, 2011 to Jun. 9, 2011.
Prosecution History of U.S. Appl. No. 12/150,675 Without Cited References, From Apr. 29, 2008 to Jun. 16, 2011.
Prosecution History of U.S. Appl. No. 12/150,998 W

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