HIV protease inhibitors, compositions containing the same,...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C546S146000, C548S540000, C514S423000

Reexamination Certificate

active

10166979

ABSTRACT:
Compounds of the formula:where the formula variables are as defined herein, are disclosed that advantageously inhibit or block the biological activity of the HIV protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with the HIV virus. Intermediates and synthetic methods for preparing such compounds are also described.

REFERENCES:
patent: 5629406 (1997-05-01), Higashida et al.
patent: 5644028 (1997-07-01), Mimoto et al.
patent: 5932550 (1999-08-01), Kato et al.
patent: 5962640 (1999-10-01), Kato et al.
patent: 6222043 (2001-04-01), Kato et al.
patent: 6313094 (2001-11-01), Mimoto et al.
patent: 6329502 (2001-12-01), Mimoto et al.
patent: 2002/0049165 (2002-04-01), Mimoto et al.
patent: 2005/0124683 (2005-06-01), Alegria et al.
patent: 2005/0153903 (2005-07-01), Kucera et al.
patent: 705193 (1997-02-01), None
patent: 2179935 (1996-12-01), None
patent: 0498680 (1992-02-01), None
patent: 0574135 (1993-12-01), None
patent: 0706794 (1996-04-01), None
patent: 0751145 (1996-06-01), None
patent: 0490667 (1999-06-01), None
patent: 8259532 (1996-10-01), None
patent: 10-87489 (1998-04-01), None
patent: 10101654 (1998-04-01), None
patent: 10-182601 (1998-07-01), None
patent: 2003119137 (2003-04-01), None
patent: WO93/13066 (1993-07-01), None
patent: WO 95/09843 (1995-04-01), None
patent: WO 48/46582 (1998-10-01), None
patent: WO 00/48466 (2000-08-01), None
patent: WO 02/100844 (2002-12-01), None
patent: WO 2002 100845 (2002-12-01), None
patent: WO 03/035076 (2003-05-01), None
patent: WO 03/035650 (2003-05-01), None
patent: WO 03/049690 (2003-06-01), None
patent: WO 03/062204 (2003-07-01), None
patent: WO 03/062238 (2003-07-01), None
patent: WO 03/047564 (2003-12-01), None
Takashiro et al., Bioorganic & Medicinal Chemistry 6 (1998) 595-604.
Database CAS ONLINE on STN, Chem. Abstr., Accession No. 1998:211105, JP 10087489 A2 (Sankyo Co., LTD.) Apr. 7, 1998, abstract.
Charlesworth et al., “Phthalide Formation,”Can J. Chem.41:1071-1077 (1963).
Demange et al., “Practical Synthesis of Boc and Fmoc Protected 4-Fluoro and 4-Difluoroprolines fromTrans-4-Hydrozyproline,”Tetrahedron Letters39:1169-1172 (1998).
Dondoni et al., “Total Synthesis of (+)-Galactostatin. An Illustration of the Utility of the Thiazole-Aldehyde Synthesis,”J. Org. Chem.60:4749-4754 (1995).
Enantiomers, Racemates, and Resolutions(1991).
Fujiwara et al., “Orientation in Nitration and Sulfonation of 2,5-Dimethylbenzoic Acid,”Can J. Chem.48:1346-1349 (1970).
Harada et al., “Synthesis and Resolution of -N-[1-methyl-4(3-methylbenzyl)hexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-Carboxamide By Preferential Crystallization,”Tetrahedron Asymmetry8(14):2367-2374 (1997).
Holzgrabe, U., “Cer(IV)sulfat-Oxidationen: Intramolekulare Cyclisierung von N-Benzyl-β-Aminoketonen zu 4-Benzoyl-1,2,3,4-tetrahydro-isochinolinen,”Arch. Pharm.320:647-654 (1987).
Huang et al., “The Improved Preparation of 7,8-Dihydro-Quinoline-596H)-One And 6,7-Dihydro-5H-1-Pyrindin-5-One,”Synthetic Communications28(7): 1197-1200 (1998).
Hursthouse et al., “Reations of Ethyl 2-acetyl-2-azabicyclo[2.2.1]Hept-5-ene-3-Carboxylate and 4-acetylamino-2-oxabicyclo[3.3.0]oct-7-en-3-one With Some Electrophiles,”J. Chem. Soc.1:2419-2425 (1995).
Karanewsky et al., “Phosphinyloxy)acyl Amino Acid Inhibitors Of Angiotensin Converting Enzyme,”J. Med. Chem.33:1459-1469 (1990).
Ludeman et al. “Synthesis and Antitumor Activity of Cyclophosphamide Analogs. 1. Benzo Annnulated Cyclophosphamide and Related Systems,”Journal of Medicinal Chemistry18(12):1251 (1975).
Matayoshi et al., “Novel Fluorogenic Substrates For Assaying Retroviral Proteases By Resonance Energy Transfer,”Science247:954-958 (1990).
Miller, “Preparation of Crystalline Diphenyldiazomethane,”J. Org. Chem.24:560-561 (1958).
Mimoto et al., “Structure-Activity Relationship of Small-Sized HIV Protease Inhibitors Containing Allophenylnorstatine,”J. Med. Chem.42:1789-1802 (1999).
Nagasawa, et al., “β-Substituted Cysteines as Sequestering Agents for Ethanol-Derived Acetaldehyde in Vivo,”J. Med. Chem.30:1373 (1987).
Nussbaumer et al., “Synthesis and Structure-Activity Relationships of Benzo[b]thienylallylamine Antimycotics,”.Med. Chem.34:65-73 (1991).
O'Brien et al., “Inhibitors of Acyl-CoA:Choloesterol O-Acyl Transferase (ACAT) as Hypocholesterolemic Agents. Incorporation of Amide or Amine Functionalities into a Series of Disubstituted Ureas And Carbamates. Effects on ACAT Inhibition In Vitro and Efficacy In Vivo,”J. Med. Chem.37:1810-1822 (1994).
Onda et al., “Structure of Carzinophilin. II. A New Amino Acid and Its Derivative From Carzinophillin,”Chem. Pharm. Bull.19(10):2013-2019 (1971).
Pauwels et al., “Rapid and Automated Tetrazolium-Based Colorimetric Assay For The Detection Of Anti-HIV Compounds,”Journal of Virological Methods20:309-321 (1988).
Petropoulos et al., “A Novel Phenotypic Drug Susceptibility Assay for Human Immunodeficiency Virus Type 1,”Antimicrob Agents Chemother44(4):920-928 (2000).
Protective Groups In Organic Synthesis3rdEdition (1999).
Weislow et al., “New Soluble-Formazan Assay For HIV-1 Cytopathic Effects: Application To High-Flux For AIDS-Antiviral Activity,”Journal of the National Cancer Institute81(8):577-586 (1989).
Wipf et al., “SN2'-Reactions of Peptide Aziridines. A Cuprate-Based Approach to (E)-Alkene Isosteres”J. Org. Chem.59:4875-4886 (1994).
Yoshimura et al., “JE-2147: A Dipeptide Protease Inhibitor (PI) That Potently Inhibits Multi-PI-Resistant HIV-1,”Proc. Natl. Acad. Sci. USA96:8675-8680 (Jul. 1999).
Bell et al., “Developmetn of Orally Active Oxytocin Antagonists: Studies on 1-(1-{4-[1-(2-Methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy]-2-methoxybenzoyl}peperidin-4-yl)-1,4-dihydrobenz[d][1,3]oxazin-2-one (L-372,662) and Related Pyridines,”J. Med. Chem.41:2146-2163 (1998).
Bobbitt et al., “Synthesis of Isoquinoline Alkaloids. II. The Synthesis and Reactions of 4-Methyl-3-pyridinecarboxaldehyde and Other 4-Methyl-3-substituted Pyridines,”J. Org. Chem.25:560 (1959).
Bundgaard,Design of Prodrugs(1985).
Carlsen et al., “Thermolysis of N-Allylic 1,2,4-Triazoles,”Institute of Organic Chemistry34:797-805 (1997).
Van-Duc Le, “Structure-Activity Studies of FIV and HIV Protease Inhibitors Containing Allophenylnorstatine”, Biorg. Med. Chem., vol. 9, 2001, pp. 1185-1195.
Mimoto et al. “Structure- Activity Relationship of Orally Potent Tripeptide- Based HIV Protease Inhibitors Containing HydroxymethylCarbonyl Isotease”, Chem & Pharm. Bulletin, Pharm Soc. Of Japan, vol. 48 (9), 2000, pp. 1310-1326.
Sodergren et al. “Allylic Alcohols Via Catalytic Asymmmetric Expoxide Rearrangement”, J. AmChem. Soc., vol. 122 (28), 2000, pp. 6610-6618.
Falorni et al. “Optically Active 4-Oxaproline Derivatives: New Useful Chiral Synthons Derived From Serine and Threonine”, Tetrahedron: Asymmetry, vol. 6(1), 1995, pp. 287-294.
Yoshiaki, Patent Abstracts of Japan, Publication No. 10182601, 1998, No. 12.
Sheha et al., Euro J. Med. Chem., vol. 35 (10), 2000, pp. 887-894.
Kitzaki et al., Chem & Pharm. Bulletin, Pharm. Soc. of Japan, vol. 42(12), 1994, pp. 2636-2640.
Slee, J.A.C.S., vol. 117(48), 1995, pp. 11867-11878.
Komai et al., Biorg. Med. Chem., vol. 4 (8), 1996, pp. 1356-1377.
Kiso et. al., Arch. Pharm., Pharm. Med. Chem., vol. 331, 1998, pp. 87-89.
Matsumoto et al., Biorg. Med. Chem., vol. 9(2), 2001, pp. 417-430.
Tam et al., J. Med. Chem., vol. 35, No. 7, 1992, pp. 1318-1320.
Andrés, “Stereoselective Cyanation Of Chiral α-Amino Aldehydes By Reaction With Nagata's Reagent: A Route To Enantiopure β-Amino-α-Hydroxy Acids,”Tetrahedron Asymm., 2001, pp. 347-353, vol. 12.
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