Tetrahydrotriazolopyrazine derivatives and uses thereof

Details Tetrahydrotriazolopyrazine derivatives and uses thereof Tetrahydrotriazolopyrazine derivatives and uses thereof

2008-05-07

2010-10-26

Wilson, James O (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C544S350000

Reexamination Certificate

active

07820666

ABSTRACT:
This invention relates to novel substituted tetrahydrotriazolopyrazines and their derivatives, pharmaceutically acceptable salts, solvates, and hydrates thereof. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering an enzyme inhibitor of dipeptidyl-peptidase IV (DPP-IV).

REFERENCES:
patent: 5304121 (1994-04-01), Sahatjian
patent: 5886026 (1999-03-01), Hunter et al.
patent: 6099562 (2000-08-01), Ding et al.
patent: 6221335 (2001-04-01), Foster
patent: 6303661 (2001-10-01), Demuth et al.
patent: 6440710 (2002-08-01), Keinan et al.
patent: 6603008 (2003-08-01), Ando et al.
patent: 6699871 (2004-03-01), Edmondson et al.
patent: 6803031 (2004-10-01), Rabinowitz et al.
patent: 7517990 (2009-04-01), Ito et al.
patent: 2003/0100563 (2003-05-01), Edmondson et al.
patent: 2004/0068141 (2004-04-01), Armstrong et al.
patent: 2005/0032804 (2005-02-01), Cypes et al.
patent: 2007/0082929 (2007-04-01), Gant et al.
patent: 2007/0197695 (2007-08-01), Potyen et al.
patent: 2007/0259927 (2007-11-01), Suzuki et al.
patent: 2008/0039367 (2008-02-01), Izumi et al.
patent: 2008/0103122 (2008-05-01), Veltri
patent: 2009/0076013 (2009-03-01), Czarnik et al.
patent: 1084705 (2001-03-01), None
patent: 0896538 (2001-07-01), None
patent: 1625847 (2006-02-01), None
patent: 1412357 (2006-03-01), None
patent: 1654263 (2007-09-01), None
patent: WO 95/26325 (1995-10-01), None
patent: WO 97/40832 (1997-11-01), None
patent: WO03004498 (2003-01-01), None
patent: WO 2004/085378 (2004-10-01), None
patent: WO 2004/085661 (2004-10-01), None
patent: WO 2004/087650 (2004-10-01), None
patent: WO 2004/1130375 (2004-12-01), None
patent: WO 2005/003135 (2005-01-01), None
patent: WO 2006/011588 (2006-02-01), None
patent: WO 2006/022428 (2006-02-01), None
patent: WO 2006/119260 (2006-11-01), None
patent: WO 2007/002374 (2007-01-01), None
patent: WO 2007/037296 (2007-05-01), None
patent: WO 2007/118651 (2007-10-01), None
http://en.wikipedia.org/wiki/Deuterium 9last checked on Sep. 21, 2009).
Vincent, et. al., Drug Metabolism and Disposition; 35(4); (2007) pp. 538-8.
Kushner, et. al.; Cnadian Journal of Physiology and Pharmacology; (1997) 77(2) pp. 79-88.
Vincent, et. al., Drug Metabolism and Disposition (2007); vol. 35, No. 4, pp. 533-538.
Park, et. al.; Annu. Rev. Pharmacol. Toxicol. 2001. 41:443-70.
Kushner, et. al.; Canadian Journal of Physiology and Pharmacology; (1999), 77, 2, pp. 79-88.
Wada E et al., Seikagaku 1994, 66: 15-28.
Gannes LZ et al., “Natural Abundance Variations in Stable Isotopes and their Potential Uses in Animal Physiology Ecology,” Comp Biochem Physiol Mol Integr Physiol 1998, 119: 725-737.
Kim, D et.al., “(2R)-4-[3-(Trifluoromethyl)-5,6-dihydro[1,2,4]trizolo[4,3-α]pyrazin-7(8H)-yl]-1- (2,4,5-trifluorophenyl)butan-2-amine: A Potent, Orally Active Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes,” J Med Chem, 2005, 48(1):141-151.
Hansen, BK et al., “First Generation Process for the Preparation of the DPP-IV Inhibitor Sitagliptin,” Org Proc Res Develop, 2005, 9:634-639.
Sorbera, LA et al., 'MK-0431. Agent for Type 2 Diabetes Dipeptidyl-Peptidase IV (CD26) Inhibitor, Drugs Fut, 2005, 30(4):337-343.
O'Hagan, D. et al., “Efficient Routes to Isotopically Labelled Epichlorohydrins (Chloromethyl) oxiranes),” J. Labelled Comp and Radiopharmaceuticals, 1994, 34(9):871-880.
Wotiz, JH et al., “Mechanism of the base-catalyzed prototropic propargylic rearrangement in vicinal diamines,” J Org Chem, 1973, 38(3):489-493.
Fontana, E et al., “Synthesis of Brostallicin (PNU-166196A) Labelled with2H and14C,” J Labelled Comp and Radiopharmaceuticals, 2002, 45(11):899-909.
Balaban, A. et al., “Regioselective deuteriation knetics of 2-, and 6-methyl groups in D2O solutions of pyrylium and N-methylpyridinium perchlorates possessing also 3-methyl or 3-phenyl groups,” J Labelled Compd and Radiopharmaceuticals, 1982, 19(6):783-794.
Haedener, A et al., “Synthesis of Specifically Labelled L-Phenylalanines Using Phenylalanine Ammonia Lyase Activity,” J Labelled Compd and Radiopharmaceuticals, 1987, 24(11):1291-1306.
Freireich, EJ et al., “Quantitative Comparison of Toxicity of Anticancer Agents in Mouse, Rat, Hamster, Dog, Monkey, and Man,” (1966) Cancer Chemother. Rep 50: 219-244.
Obach, RS, “Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes,” Drug Metab Disp, 1999, 27:1350-1359.
Houston, JB et al., “Prediction of Hepatic Clearance from Microsomes, Hepatocytes, and Liver Slices,” Drug Metab Rev, 1997, 29:891-922.
Houston, JB, “Utility of In Vitro Drug Metabolism Data in Predicting In Vivo Metabolic Clearance,” Biochem Pharmacol, 1994, 47:1469-1479.
Iwatsubo, T et al., “Prediction of In Vivo Drug Metabolism in the Human Liver from In Vivo Metabolism Data,” Pharmacol Ther, 1997, 73:147-171.
Lavé, T, et al., “The Use of Human Hepatocytes to Select Compounds Based on Their Expected Hepatic Extraction Ratios in Humans,” Pharm Res, 1997, 14:152-155.
Vincent, S. H. et al., “Metabolism and Excretion of the Dipeptidyl Peptidase 4 Inhibitor [14C]Sitagliptin in Humans,” Drug Metabolism and Disposition, Jan. 12, 2007, 35(4), 533-538.
Baillie, “The Use of Stable Isotopes in Pharmacological Research”, Pharmacology Reviews, Jun. 1981, 33(2), 81-132 (In 2 Parts).
Browne, “Stable Isotope Techniques in Early Drug Development: An Economic Evaluation”, J. Clin. Pharmacology, Mar. 1998, 38(3), 213-220.
Cherrah et al., “Study of Deuterium Isotope Effects on Protein Binding by Gas Chromatography/Mass Spectrometry. Caffeine and Deuterated Isotopomers”, Biomed and Environmental Mass Spectrometry, Apr. 27, 1987, 14(11), 653-657.
Dyck et al., “Effects of Deuterium Substitution on the Catabolism of B-Phenylethylaine: An In Vivo Study”, J. Neurochemistry, Feb. 1986, 46(2), 399-404.
Fisher et al., “The Complexities Inherent in Attempts to Decrease Drug Clearance by Blocking Sites of CYP-Mediated Metabolism”, Current Opin. Drug Discov. Dev., Jan. 2006, 9(1), 101-109.
Foster, “Deuterium Isotope Effects in the Metabolism of Drugs and Xenobiotics: Implications for Drug Design”, Adv. Drug Res., (no month available)1985, 14, 2-40.
Foster, “Deuterium Isotope Effects in Studies of Drug Metabolism”, Trends in Pharmaceutical Sciences, Dec. 1984, 5, 524-527.
Gouyette, “Synthesis of Deuterium-Labelled Elliptinium and Its Use in Metabolic Studies”, Biomed and Environmental Mass Spectrometry, Mar. 1, 1988, 15(5), 243-247.
Haskins, “The Application of Stable Isotopes in Biomedical Research”, Biomed Spectrometry, Jul. 1982, 9(7), 269-277.
Honma et al., “The Metabolism of Roxatideine Acetate Hydrochloride—Liberation of Deuterium From The Piperidine Ring During Hydroxylation”, Drug Metab. Dispos., Mar. 17, 1987, 15(4), 551-559.
Kushner et al., “Pharmacological Uses and Perspectives of Heavy Water and Deuterated Compounds”, Can. J. Physiol. Pharmacol, Feb. 1999, 77(2), 79-88.
Pieniaszek et al., “Moricizine Bioavailability Via Simultaneous, Dual, Stable Isotope Administration: Bioequivalence Implications”, J. Clin. Pharmacology, Aug. 1999, 39(8), 817-825.
Tonn et al., “Simultaneous Analysis of Diphenhydramine and a Stable Isotope Analog (2H10) Diphenhydramine Using Capillary Gas Chromatography with Mass Selective Detection in Biological Fluids from Chronically Instrumented Pregnant Ewes”, Biol. Mass Spectrometry, Jul. 6, 1993, 22(11), 633-642.
Wolen, “The Application of Stable Isotopes to Studies of Drug Bioavailability and Bioequivalence”, J. Clin. Phamacolo

Affiliated with

Also associated with

Rating

Tetrahydrotriazolopyrazine derivatives and uses thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Tetrahydrotriazolopyrazine derivatives and uses thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Tetrahydrotriazolopyrazine derivatives and uses thereof will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4188269