WO1999033792A3 - Prodrugs os aspartyl protease inhibitors - Google Patents

Prodrugs os aspartyl protease inhibitors Download PDF

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Publication number
WO1999033792A3
WO1999033792A3 PCT/US1998/027403 US9827403W WO9933792A3 WO 1999033792 A3 WO1999033792 A3 WO 1999033792A3 US 9827403 W US9827403 W US 9827403W WO 9933792 A3 WO9933792 A3 WO 9933792A3
Authority
WO
WIPO (PCT)
Prior art keywords
prodrugs
relates
protease inhibitors
aspartyl protease
pharmaceutical compositions
Prior art date
Application number
PCT/US1998/027403
Other languages
French (fr)
Other versions
WO1999033792A2 (en
Inventor
Michael R Hale
Roger D Tung
Christopher T Baker
Andrew Spaltenstein
Eric Steven Furfine
Istvan Kaldor
Wieslaw Mieczyslaw Kazmierski
Original Assignee
Vertex Pharma
Michael R Hale
Roger D Tung
Christopher T Baker
Andrew Spaltenstein
Eric Steven Furfine
Istvan Kaldor
Wieslaw Mieczyslaw Kazmierski
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Vertex Pharma, Michael R Hale, Roger D Tung, Christopher T Baker, Andrew Spaltenstein, Eric Steven Furfine, Istvan Kaldor, Wieslaw Mieczyslaw Kazmierski filed Critical Vertex Pharma
Priority to AU20102/99A priority Critical patent/AU2010299A/en
Publication of WO1999033792A2 publication Critical patent/WO1999033792A2/en
Publication of WO1999033792A3 publication Critical patent/WO1999033792A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
    • C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
    • C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
    • C07F9/65844—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a five-membered ring which may be condensed with another ring system

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to prodrugs of a class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of prodrugs of HIV aspartyl protease inhibitors characterized by favorable aqueous solubility, high oral bioavailability and facile in vivo generation of the active ingredient. This invention also relates to pharmaceutical compositions comprising these prodrugs. The prodrugs and pharmaceutical compositions of this invention are particularly well suited for decreasing the pill burden and increasing patient compliance. This invention also relates to methods of treating mammals whith these prodrugs and pharmaceutical compositons.
PCT/US1998/027403 1997-12-24 1998-12-23 Prodrugs os aspartyl protease inhibitors WO1999033792A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU20102/99A AU2010299A (en) 1997-12-24 1998-12-23 Prodrugs os aspartyl protease inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6880697P 1997-12-24 1997-12-24
US60/068,806 1997-12-24

Publications (2)

Publication Number Publication Date
WO1999033792A2 WO1999033792A2 (en) 1999-07-08
WO1999033792A3 true WO1999033792A3 (en) 1999-09-16

Family

ID=22084811

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/027403 WO1999033792A2 (en) 1997-12-24 1998-12-23 Prodrugs os aspartyl protease inhibitors

Country Status (2)

Country Link
AU (1) AU2010299A (en)
WO (1) WO1999033792A2 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE42889E1 (en) 1992-08-25 2011-11-01 G.D. Searle Llc α- and β- amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US8143421B2 (en) 2002-03-12 2012-03-27 Tibotec Pharmaceuticals Ltd. Broadspectrum substituted benzimidazole sulfonamide HIV protease inhibitors
USRE43596E1 (en) 1992-08-25 2012-08-21 G.D. Searle Llc α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors

Families Citing this family (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5968942A (en) 1992-08-25 1999-10-19 G. D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
GB9815567D0 (en) * 1998-07-18 1998-09-16 Glaxo Group Ltd Antiviral compound
US6617310B2 (en) * 2000-07-19 2003-09-09 Bristol-Myers Squibb Pharma Company Phosphate esters of bis-amino acid sulfonamides containing substituted benzyl amines
EE05385B1 (en) 2001-02-14 2011-02-15 Tibotec�Pharmaceuticals�Ltd. Broad-spectrum Á2- (Substituted Áamino) Benzothiazole Sulphonamides ÁkuiÁHIVÁProtease Inhibitors, Methods of Preparation, and UseUnited Pharmaceutical Formulations
CN100491360C (en) 2001-04-09 2009-05-27 泰博特克药品有限公司 Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide HIV protease inhibitors
AU2002310818B2 (en) 2001-05-11 2007-12-13 Tibotec Pharmaceuticals Ltd. Broadspectrum 2-amino-benzoxazole sulfonamide HIV protease inhibitors
BR0215260A (en) 2001-12-21 2004-12-07 Tibotec Pharm Ltd Broad spectrum heterocyclically substituted phenyl sulfonamide HIV protease inhibitors
IL165043A0 (en) 2002-05-17 2005-12-18 Tibotec Pharm Ltd broadspectrum substituted benzisoxazole sulfonamide hiv protease inhibitors
CA2493940C (en) 2002-08-14 2011-11-22 Tibotec Pharmaceuticals Ltd. Broadspectrum substituted oxindole sulfonamide hiv protease inhibitors
US20050131042A1 (en) * 2003-12-11 2005-06-16 Flentge Charles A. HIV protease inhibiting compounds
US8193227B2 (en) 2003-12-11 2012-06-05 Abbott Laboratories HIV protease inhibiting compounds
UA83881C2 (en) 2003-12-18 2008-08-26 Янссен Фармацевтика Н.В. Pyrido- and pyrimidopyrimidine derivatives as anti-proliferative agents
EP1789029A2 (en) 2004-08-30 2007-05-30 Interstitial Therapeutics Methods and compositions for the treatment of cell proliferation
BRPI0516915A (en) 2004-12-01 2008-03-11 Devgen Nv 5-carboxamido substituted thiazole derivatives which interact with ion channels, particularly with ion channels of the kv family
NI200700147A (en) 2004-12-08 2019-05-10 Janssen Pharmaceutica Nv QUINAZOLINE DERIVATIVES KINE INHIBITORS TARGETING MULTIP
EP1938691A3 (en) 2004-12-17 2009-07-22 Devgen NV Nematicidal compositions
US20080194554A1 (en) * 2005-03-11 2008-08-14 Mclean Ed W Hiv Protease Inhibitors
AR053845A1 (en) 2005-04-15 2007-05-23 Tibotec Pharm Ltd 5-TIAZOLILMETIL [(1S, 2R) -3 - [[(2-AMINO-6-BENZOXAZOLIL) SULFONIL)] (2-METHYLPROPIL) AMINO] -2-HYDROXY-1- (PHENYLMETIL) PROPIL] CARBAMATE AS A PHARMACY IMPROVER METABOLIZED BY THE CYCROCHROME P450
US8003627B2 (en) 2005-10-21 2011-08-23 Universiteit Antwerpen Urokinase inhibitors
AR057182A1 (en) 2005-11-28 2007-11-21 Tibotec Pharm Ltd AMINOPHENYL SULFONAMIDE COMPOUNDS REPLACED AS HIV PROTEASE INHIBITORS
AR058238A1 (en) 2005-11-28 2008-01-23 Tibotec Pharm Ltd COMPOUNDS AND DERIVATIVES OF AMINOPHENYL SULFONAMIDE REPLACED AS HIV PROTEASE INHIBITORS
EP3696171A1 (en) 2006-07-07 2020-08-19 Gilead Sciences, Inc. Modulators of pharmacokinetic properties of therapeutics
MX2009000456A (en) 2006-07-13 2009-01-27 Janssen Pharmaceutica Nv Mtki quinazoline derivatives.
WO2008028688A2 (en) 2006-09-08 2008-03-13 Bayer Schering Pharma Aktiengesellschaft Compounds and methods for 18f labeled agents
ES2603617T3 (en) 2007-02-23 2017-02-28 Gilead Sciences, Inc. Modulators of pharmacokinetic properties of therapeutics
EP2185562B1 (en) 2007-07-27 2015-12-02 Janssen Pharmaceutica, N.V. Pyrrolopyrimidines useful for the treatment of proliferative diseases
EP2053033A1 (en) 2007-10-26 2009-04-29 Bayer Schering Pharma AG Compounds for use in imaging, diagnosing and/or treatment of diseases of the central nervous system or of tumors
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EP2283024B1 (en) 2008-03-10 2013-05-15 Janssen Pharmaceutica, N.V. 4-aryl-2-anilino-pyrimidines as plk kinase inhibitors
EP2116236A1 (en) 2008-04-21 2009-11-11 Université de Mons-Hainaut Bisbenzamidine derivatives for use as antioxidant
WO2011061295A1 (en) 2009-11-19 2011-05-26 Blue Medical Devices Bv Narrow profile composition-releasing expandable medical balloon catheter
WO2011141515A1 (en) 2010-05-14 2011-11-17 Bayer Pharma Aktiengesellschaft Diagnostic agents for amyloid beta imaging
US8785648B1 (en) 2010-08-10 2014-07-22 The Regents Of The University Of California PKC-epsilon inhibitors
GB201019043D0 (en) 2010-11-10 2010-12-22 Protea Biopharma N V Use of 2',5'-oligoadenylate derivative compounds
EP2700396A3 (en) 2012-06-20 2015-04-29 Sylphar Nv Strip for the delivery of oral care compositions
US9877981B2 (en) 2012-10-09 2018-01-30 President And Fellows Of Harvard College NAD biosynthesis and precursors for the treatment and prevention of cancer and proliferation
EP3180003B1 (en) 2014-07-01 2022-01-12 The Regents of the University of California Pkc-epsilon inhibitors
WO2016083490A1 (en) 2014-11-27 2016-06-02 Remynd Nv Compounds for the treatment of amyloid-associated diseases
KR20180006389A (en) 2015-04-28 2018-01-17 뉴사우쓰 이노베이션스 피티와이 리미티드 NAD + targeting for the treatment of chemotherapy and radiotherapy induced cognitive impairment, neuropathy and inactivity
PL3621963T3 (en) 2017-05-11 2024-05-20 Remynd N.V. Compounds for the treatment of epilepsy, neurodegenerative disorders and other cns disorders
BR112022016733A2 (en) 2020-02-24 2022-10-11 Univ Leuven Kath PYRROLPIRIDINE AND IMIDAZOPYRIDINE ANTIVIRAL COMPOUNDS
JP2024500543A (en) 2020-12-22 2024-01-09 ルクセンブルク インスティテュート オブ ヘルス（エルアイエイチ） Conolidine analogs as selective ACKR3 modulators for the treatment of cancer and cardiovascular diseases
US20240002351A1 (en) 2021-03-04 2024-01-04 Universiteit Antwerpen Quinazolin-4-one and thieno[2,3-d]pyrimidin-4-one inhibitors of erbb4 (her4) for use in the treatment of cancer
CN117500772A (en) 2021-05-31 2024-02-02 泰利克斯制药(创新)私人有限公司 Improved prostate specific membrane antigen targeted radiopharmaceuticals and uses thereof
EP4387629A1 (en) 2021-08-18 2024-06-26 Katholieke Universiteit Leuven KU Leuven Research & Development 6-substituted- and 6,7-disubstituted-7-deazapurine ribonucleoside analogues
WO2023046900A1 (en) 2021-09-23 2023-03-30 Katholieke Universiteit Leuven Ribonucleoside analogues against -sars-cov-2
WO2023241799A1 (en) 2022-06-15 2023-12-21 Université Libre de Bruxelles Flavanols for use in the treatment of retroviral infections
WO2024062043A1 (en) 2022-09-21 2024-03-28 Universiteit Antwerpen Substituted phenothiazines as ferroptosis inhibitors

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994005639A1 (en) * 1992-09-08 1994-03-17 Vertex Pharmaceuticals Incorporated Sulfonamide inhibitors of hiv-aspartyl protease
WO1995006030A1 (en) * 1993-08-24 1995-03-02 G.D. Searle & Co. Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors
WO1995024385A1 (en) * 1994-03-07 1995-09-14 Vertex Pharmaceuticals Incorporated Sulphonamide derivatives as aspartyl protease inhibitors
WO1996033184A1 (en) * 1995-04-19 1996-10-24 Vertex Pharmaceuticals Incorporated Thf-containing sulfonamide inhibitors of aspartyl protease

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994005639A1 (en) * 1992-09-08 1994-03-17 Vertex Pharmaceuticals Incorporated Sulfonamide inhibitors of hiv-aspartyl protease
US5585397A (en) * 1992-09-08 1996-12-17 Vertex Pharmaceuticals, Incorporated Sulfonamide inhibitors of aspartyl protease
WO1995006030A1 (en) * 1993-08-24 1995-03-02 G.D. Searle & Co. Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors
WO1995024385A1 (en) * 1994-03-07 1995-09-14 Vertex Pharmaceuticals Incorporated Sulphonamide derivatives as aspartyl protease inhibitors
WO1996033184A1 (en) * 1995-04-19 1996-10-24 Vertex Pharmaceuticals Incorporated Thf-containing sulfonamide inhibitors of aspartyl protease

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J.M. BALKOVEC ET AL, J. MED. CHEM., vol. 35, no. 1, 1992, pages 194 - 198, XP002104270 *
S. SAWADA ET AL, CURR. PHARM. DES., vol. 1, no. 1, 1995, pages 113 - 132, XP002104269 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE42889E1 (en) 1992-08-25 2011-11-01 G.D. Searle Llc α- and β- amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
USRE43596E1 (en) 1992-08-25 2012-08-21 G.D. Searle Llc α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US8143421B2 (en) 2002-03-12 2012-03-27 Tibotec Pharmaceuticals Ltd. Broadspectrum substituted benzimidazole sulfonamide HIV protease inhibitors

Also Published As

Publication number Publication date
WO1999033792A2 (en) 1999-07-08
AU2010299A (en) 1999-07-19

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