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WO1999067254A3 - Multi-drug resistant retroviral protease inhibitors and use thereof - Google Patents

Multi-drug resistant retroviral protease inhibitors and use thereof Download PDF

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Publication number
WO1999067254A3
WO1999067254A3 PCT/US1999/014120 US9914120W WO9967254A3 WO 1999067254 A3 WO1999067254 A3 WO 1999067254A3 US 9914120 W US9914120 W US 9914120W WO 9967254 A3 WO9967254 A3 WO 9967254A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
optionally substituted
retroviral protease
resistant retroviral
multidrug
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1999/014120
Other languages
French (fr)
Other versions
WO1999067254A2 (en
Inventor
John W Erickson
Sergei V Gulnik
Arun K Ghosh
Khaja A Hussain
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Illinois at Urbana Champaign
University of Illinois System
US Department of Health and Human Services
Original Assignee
University of Illinois at Urbana Champaign
University of Illinois System
US Department of Health and Human Services
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 University of Illinois at Urbana Champaign, University of Illinois System, US Department of Health and Human Services filed Critical University of Illinois at Urbana Champaign
Priority to PCT/US1999/014120 priority Critical patent/WO1999067254A2/en
Priority to AU48281/99A priority patent/AU4828199A/en
Publication of WO1999067254A2 publication Critical patent/WO1999067254A2/en
Publication of WO1999067254A3 publication Critical patent/WO1999067254A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4525—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
    • C12Q1/025—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
    • C12Q1/37—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase involving peptidase or proteinase
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
    • G01N2333/005—Assays involving biological materials from specific organisms or of a specific nature from viruses
    • G01N2333/08—RNA viruses
    • G01N2333/15—Retroviridae, e.g. bovine leukaemia virus, feline leukaemia virus, feline leukaemia virus, human T-cell leukaemia-lymphoma virus
    • G01N2333/155—Lentiviridae, e.g. visna-maedi virus, equine infectious virus, FIV, SIV
    • G01N2333/16—HIV-1, HIV-2
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
    • G01N2333/81—Protease inhibitors
    • G01N2333/8107—Endopeptidase (E.C. 3.4.21-99) inhibitors
    • G01N2333/8142—Aspartate protease (E.C. 3.4.23) inhibitors, e.g. HIV protease inhibitors

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Immunology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Genetics & Genomics (AREA)
  • Virology (AREA)
  • Analytical Chemistry (AREA)
  • Biophysics (AREA)
  • Epidemiology (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Oncology (AREA)
  • AIDS & HIV (AREA)
  • Toxicology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The present invention generally provides a retroviral protease-inhibiting compound represented by formula (I), or a pharmaceutically acceptable salt, a prodrug, or an ester thereof, wherein A is a group of formula (II), (III), (IV), or (V); R?1, R2, R3, R5, or R6¿ is H, or an optionally substituted and/or heteroatom-bearing alkyl, alkenyl, alkynyl, or cyclic group; Y and/or Z are CH¿2?, O, S, SO, SO2, amino, amides, carbamates, ureas or thiocarbonyl derivatives thereof, optionally substituted with an alkyl, alkenyl, or alkynyl group; n is from 1 to 5; X is a bond, an optionally substituted methylene or ethylene, an amino, O or S; Q is C(O), C(S), or SO2; m is from 0 to 6; R?4¿ is OH, =O (keto), NH¿2?, or alkylamino, including esters, amides, and salts thereof; and W is C(O), C(S), S(O), or SO2; wherein the compound inhibits a multidrug-resistant retroviral protease. Optionally, R?5 and R6¿, together the N-W bond of formula (I), comprise a 12- to 18-membered ring. Also provided are pharmaceutical compositions for, and therapeutic methods of, treating a multidrug-resistant retroviral infection in a mammal.
PCT/US1999/014120 1998-06-23 1999-06-23 Multi-drug resistant retroviral protease inhibitors and use thereof Ceased WO1999067254A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/US1999/014120 WO1999067254A2 (en) 1998-06-23 1999-06-23 Multi-drug resistant retroviral protease inhibitors and use thereof
AU48281/99A AU4828199A (en) 1998-06-23 1999-06-23 Multi-drug resistant retroviral protease inhibitors and associated methods

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US9039398P 1998-06-23 1998-06-23
US60/090,393 1998-06-23
PCT/US1999/014120 WO1999067254A2 (en) 1998-06-23 1999-06-23 Multi-drug resistant retroviral protease inhibitors and use thereof

Publications (2)

Publication Number Publication Date
WO1999067254A2 WO1999067254A2 (en) 1999-12-29
WO1999067254A3 true WO1999067254A3 (en) 2000-02-10

Family

ID=36950030

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/014120 Ceased WO1999067254A2 (en) 1998-06-23 1999-06-23 Multi-drug resistant retroviral protease inhibitors and use thereof

Country Status (2)

Country Link
AU (1) AU4828199A (en)
WO (1) WO1999067254A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8143421B2 (en) 2002-03-12 2012-03-27 Tibotec Pharmaceuticals Ltd. Broadspectrum substituted benzimidazole sulfonamide HIV protease inhibitors

Families Citing this family (41)

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Publication number Priority date Publication date Assignee Title
DE69943266D1 (en) 1998-06-23 2011-04-21 Trustees For The University Of Illinois Board Of DRUGS FOR THE TREATMENT OF HIV-INFECTED MAMMALS
KR100792391B1 (en) 1999-10-06 2008-01-08 티보텍 파마슈티칼즈 리미티드 Hexahydrofuro [2,3-k] furan-3-yl-N- [3-[(1,3-benzodioxol-5-ylsulfonyl) (isobutyl) amino] -1-as a retroviral protease inhibitor Benzyl-2-hydroxypropyl] carbamate
PT1370543E (en) 2001-02-14 2007-02-28 Tibotec Pharm Ltd Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors
KR100872029B1 (en) * 2001-04-09 2008-12-05 티보텍 파마슈티칼즈 리미티드 Broad range of 2- (substituted-amino) -benzoxazole sulfonamide HIV protease inhibitors
EE05307B1 (en) 2001-05-11 2010-06-15 Tibotec Pharmaceuticals Ltd. Broad-spectrum 2-aminobenzoxazole sulfonamides as HIV protease inhibitors, their use, pharmaceutical composition and method for inhibiting retroviral replication
AP1758A (en) * 2001-09-10 2007-07-30 Tibotec Pharm Ltd Method for the preparation of hexahydro-furo [2,3-b]furan-3-ol.
TWI286476B (en) * 2001-12-12 2007-09-11 Tibotec Pharm Ltd Combination of cytochrome P450 dependent protease inhibitors
BR0215260A (en) * 2001-12-21 2004-12-07 Tibotec Pharm Ltd Broad spectrum heterocyclically substituted phenyl sulfonamide HIV protease inhibitors
US7285566B2 (en) 2002-01-07 2007-10-23 Erickson John W Resistance-repellent retroviral protease inhibitors
US7109230B2 (en) * 2002-01-07 2006-09-19 Sequoia Pharmaceuticals, Inc. Resistance-repellent retroviral protease inhibitors
US7157489B2 (en) * 2002-03-12 2007-01-02 The Board Of Trustees Of The University Of Illinois HIV protease inhibitors
LT2767539T (en) 2002-05-16 2017-09-25 Janssen Sciences Ireland Uc Pseudopolymorphic forms of a HIV protease inhibitor
JP4674084B2 (en) 2002-05-17 2011-04-20 テイボテク・フアーマシユーチカルズ・リミテツド Broad spectrum substituted benzisoxazolesulfonamide HIV protease inhibitors
BR0305717A (en) * 2002-08-02 2004-09-28 Tibotec Pharm Ltd Broad-spectrum hiv 2-amino-benzothiazole sulfonamide protease inhibitors
OA12893A (en) * 2002-08-02 2006-10-13 Tibotec Pharm Ltd Broadspectrum 2-Amino-Benzothiazole Sulfonamide HIV Protease Inhibitors.
WO2004016619A1 (en) * 2002-08-14 2004-02-26 Tibotec Pharmaceuticals Ltd. Broadspectrum substituted oxindole sulfonamide hiv protease inhibitors
WO2004060895A1 (en) 2002-12-27 2004-07-22 Sumitomo Chemical Company, Limited Process for producing hexahydrofurofuranol derivative, intermediate thereof and process for producing the same
GB0310593D0 (en) * 2003-05-08 2003-06-11 Leuven K U Res & Dev Peptidic prodrugs
AU2005222435B2 (en) 2004-03-11 2012-03-15 Sequoia Pharmaceuticals, Inc. Resistance-repellent retroviral protease inhibitors
JP5073480B2 (en) 2004-05-07 2012-11-14 セコイア、ファーマシューティカルズ、インコーポレイテッド Antiviral resistance retroviral protease inhibitors
ATE440848T1 (en) 2005-02-25 2009-09-15 Tibotec Pharm Ltd SYNTHESIS OF PROTEASE INHIBITOR PRECURSORS
WO2007002172A2 (en) * 2005-06-22 2007-01-04 University Of Massachusetts Hiv-1 protease 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
AU2007277253A1 (en) * 2006-07-24 2008-01-31 Gilead Sciences, Inc. Bisfuranyl protease inhibitors
US8153829B2 (en) 2006-11-09 2012-04-10 Janssen Pharmaceutica N.V. Methods for the preparation of hexahydrofuro[2,3-B]furan-3-ol
EP2491785A1 (en) * 2006-11-21 2012-08-29 Purdue Research Foundation Method and compositions for treating HIV infections
CA2681718A1 (en) * 2007-03-23 2008-10-02 University Of Massachusetts Hiv-1 protease inhibitors
BRPI0810609A2 (en) 2007-04-27 2014-10-21 Tibotec Pharm Ltd METHODS FOR PREPARING N-ISOBUTIL-N- (2-HYDROXY-A-AMINO-4-PHENYLBUTIL) -P-NITROBE NZENOSULFONILAMIDE DERIVATIVES
GT200800303A (en) 2007-12-24 2009-09-18 ANTI-RETROVIRAL COMBINATION
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US8791135B2 (en) 2008-07-01 2014-07-29 Purdue Research Foundation Nonpeptide HIV-1 protease inhibitors
EP2304043A4 (en) 2008-07-09 2012-05-30 Purdue Research Foundation HIV PROTEASE INHIBITORS AND METHODS OF USE
TWI482775B (en) * 2008-09-01 2015-05-01 Tibotec Pharm Ltd Process for the preparation of (3r,3as,6ar)-hexahydrofuro2,3-bfuran-3-yl(1s,2r)-3-(4-aminophenyl)sulfonyl(isobutyl)amino-1-benzyl-2-hydroxypropylcarbamate
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JP2013518096A (en) 2010-01-28 2013-05-20 マピ ファーマ リミテッド Process for the preparation of darunavir and darunavir intermediates
CN102584844B (en) * 2011-01-11 2016-04-13 浙江九洲药业股份有限公司 A kind of Prezista crystal formation and preparation method thereof
WO2013011485A1 (en) 2011-07-20 2013-01-24 Ranbaxy Laboratories Limited Process for the preparation of sulfonamides useful as retroviral protease inhibitors
WO2013105118A1 (en) 2012-01-10 2013-07-18 Council Of Scientific & Industrial Research A process for synthesis of syn azido epoxide and its use as intermediate the synthesis of amprenavir & saquinavir
US12083099B2 (en) 2020-10-28 2024-09-10 Accencio LLC Methods of treating symptoms of coronavirus infection with viral protease inhibitors

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WO1994014793A1 (en) * 1992-12-29 1994-07-07 G. D. Searle & Co. Cyclic sulfone containing retroviral protease inhibitors
WO1995006030A1 (en) * 1993-08-24 1995-03-02 G.D. Searle & Co. Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors
US5502060A (en) * 1991-10-23 1996-03-26 Merck & Co., Inc. HIV protease inhibitors
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WO1997019055A1 (en) * 1995-11-21 1997-05-29 Novartis Ag Azahexane derivatives as substrate isosters of retroviral asparate proteases
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US5705500A (en) * 1995-03-10 1998-01-06 G.D. Searle & Co. Sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors
US5723490A (en) * 1992-09-08 1998-03-03 Vertex Pharmaceuticals Incorporated THF-containing sulfonamide inhibitors of aspartyl protease
US5728718A (en) * 1994-12-20 1998-03-17 The United States Of America As Represented By The Department Of Health And Human Services 2,5-diamino-3,4-disubstituted-1,6-diphenylhexane isosteres comprising benzamide, sulfonamide and anthranilamide subunits and methods of using same
US5753660A (en) * 1995-11-15 1998-05-19 G. D. Searle & Co. Substituted sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors

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US5502060A (en) * 1991-10-23 1996-03-26 Merck & Co., Inc. HIV protease inhibitors
US5723490A (en) * 1992-09-08 1998-03-03 Vertex Pharmaceuticals Incorporated THF-containing sulfonamide inhibitors of aspartyl protease
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US5728718A (en) * 1994-12-20 1998-03-17 The United States Of America As Represented By The Department Of Health And Human Services 2,5-diamino-3,4-disubstituted-1,6-diphenylhexane isosteres comprising benzamide, sulfonamide and anthranilamide subunits and methods of using same
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US5705500A (en) * 1995-03-10 1998-01-06 G.D. Searle & Co. Sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
AU4828199A (en) 2000-01-10
WO1999067254A2 (en) 1999-12-29

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