FI20000553A - Process for Preparation of 4-Hydroxy-2-Oxopyran Derivatives Useful as Protease Inhibitors - Google Patents

Process for Preparation of 4-Hydroxy-2-Oxopyran Derivatives Useful as Protease Inhibitors Download PDF

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Publication number
FI20000553A
FI20000553A FI20000553A FI20000553A FI20000553A FI 20000553 A FI20000553 A FI 20000553A FI 20000553 A FI20000553 A FI 20000553A FI 20000553 A FI20000553 A FI 20000553A FI 20000553 A FI20000553 A FI 20000553A
Authority
FI
Finland
Prior art keywords
hydroxy
oxopyran
preparation
protease inhibitors
derivatives useful
Prior art date
Application number
FI20000553A
Other languages
Finnish (fi)
Swedish (sv)
Other versions
FI120973B (en
Inventor
Robert C Kelly
James R Gage
Bradley D Hewitt
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of FI20000553A publication Critical patent/FI20000553A/en
Application granted granted Critical
Publication of FI120973B publication Critical patent/FI120973B/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • A61P31/18Antivirals for RNA viruses for HIV
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/20Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/42Unsaturated compounds containing hydroxy or O-metal groups
    • C07C59/48Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/12Heterocyclic 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

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrane Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Disclosed is a novel process and novel intermediates to prepare [R-(R*,R*)]-N-[3-[1-[5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide (XIX) which is a protease inhibitor useful in treating humans infected with the HIV virus.
FI20000553A 1997-09-11 2000-03-10 Process for Preparation of 4-Hydroxy-2-Oxopyran Derivatives Useful as Protease Inhibitors FI120973B (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US5861897P 1997-09-11 1997-09-11
US5861897 1997-09-11
PCT/US1998/017993 WO1999012919A1 (en) 1997-09-11 1998-09-03 Process to produce 4-hydroxy-2-oxo-pyrane derivates useful as protease inhibitors
US9817993 1998-09-03

Publications (2)

Publication Number Publication Date
FI20000553A true FI20000553A (en) 2000-03-10
FI120973B FI120973B (en) 2010-05-31

Family

ID=22017924

Family Applications (1)

Application Number Title Priority Date Filing Date
FI20000553A FI120973B (en) 1997-09-11 2000-03-10 Process for Preparation of 4-Hydroxy-2-Oxopyran Derivatives Useful as Protease Inhibitors

Country Status (21)

Country Link
US (2) US6077963A (en)
EP (1) EP1015441B1 (en)
JP (3) JP4462760B2 (en)
KR (1) KR100569771B1 (en)
CN (3) CN1298714C (en)
AT (1) ATE266654T1 (en)
CA (1) CA2300204C (en)
CZ (1) CZ298847B6 (en)
DE (1) DE69823844T2 (en)
DK (1) DK1015441T3 (en)
ES (1) ES2221199T3 (en)
FI (1) FI120973B (en)
HK (3) HK1030418A1 (en)
HU (1) HU228986B1 (en)
NO (1) NO321835B1 (en)
NZ (1) NZ503338A (en)
PL (1) PL193240B1 (en)
PT (1) PT1015441E (en)
RU (2) RU2223958C2 (en)
SK (1) SK284974B6 (en)
WO (1) WO1999012919A1 (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK1161427T3 (en) 1999-03-18 2003-02-24 Upjohn Co Improved method for asymmetric hydrogenation
US6552204B1 (en) * 2000-02-04 2003-04-22 Roche Colorado Corporation Synthesis of 3,6-dialkyl-5,6-dihydro-4-hydroxy-pyran-2-one
US6500963B2 (en) 2001-02-22 2002-12-31 Boehringer Ingelheim Pharma Kg Process for preparing optically active dihydropyrones
DE10108470A1 (en) * 2001-02-22 2002-09-05 Boehringer Ingelheim Pharma Process for the production of optically active dihydropyrones
US6987123B2 (en) 2001-07-26 2006-01-17 Cadila Healthcare Limited Heterocyclic compounds, their preparation, pharmaceutical compositions containing them and their use in medicine
ATE449753T1 (en) * 2002-02-07 2009-12-15 Sumitomo Chemical Co METHOD FOR PRODUCING (R)-3-HYDROXY-3-(2-PHENYLETHYL) HEXANIC ACID AND ITS INTERMEDIATE
DE10313118A1 (en) * 2003-03-24 2004-10-07 Boehringer Ingelheim Pharma Gmbh & Co. Kg Enantioselective hydrogenation of intermediates in tipranavir synthesis
US7512945B2 (en) * 2003-12-29 2009-03-31 Intel Corporation Method and apparatus for scheduling the processing of commands for execution by cryptographic algorithm cores in a programmable network processor
CN100448836C (en) * 2005-06-03 2009-01-07 浙江中贝化工有限公司 Method for preparing key intermediate of medication for anti AIDS
MX2008001541A (en) * 2005-08-24 2008-02-15 Pfizer Methods for the preparation of hcv polymerase inhibitors.
CN101878553A (en) * 2007-11-30 2010-11-03 株式会社半导体能源研究所 Light-emitting element, light-emitting device, and electronic device
US8853393B2 (en) * 2011-07-29 2014-10-07 Anhui New Star Pharmaceutical Development Co., Ltd. Intermediate for preparing tapentadol or analogues thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1355668A (en) * 1963-02-05 1964-03-20 Advanced internal combustion rotary engine
FR1355667A (en) * 1963-02-05 1964-03-20 Meci Materiel Elect Contr Tubular sheath for electrode used for pH measurement
FR2096877B1 (en) * 1970-07-09 1973-08-10 Hexachimie
JPH0665657B2 (en) * 1984-11-08 1994-08-24 日本化薬株式会社 Production of optically active mandelic acid
JPH072677B2 (en) * 1988-02-19 1995-01-18 株式会社クラレ Optical resolution of (±) -2-hydroxy-4-phenylbutanoic acid
JPH01221345A (en) * 1988-02-27 1989-09-04 Ajinomoto Co Inc Optical resolution of mandelic acid derivative
JP3084577B2 (en) * 1991-09-27 2000-09-04 山川薬品工業株式会社 Method for producing optically active atrolactic acid and intermediate for production
JP3178086B2 (en) * 1992-06-17 2001-06-18 山川薬品工業株式会社 Method for producing optically active α-methylbenzylamine
ZA938019B (en) * 1992-11-13 1995-04-28 Upjohn Co Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating HIV and other retroviruses
ATE263761T1 (en) * 1993-11-19 2004-04-15 Parke Davis & Co 5,6-DIHYDROPYRON DERIVATIVES AS PROTEASE INHIBITORS AND ANTIVIRAL AGENTS
IL129871A (en) * 1994-05-06 2003-11-23 Pharmacia & Upjohn Inc Process for preparing 4-phenyl-substituted octanoyl-oxazolidin-2-one intermediates that are useful for preparing pyran-2-ones useful for treating retroviral infections

Also Published As

Publication number Publication date
CN100471832C (en) 2009-03-25
AU9296598A (en) 1999-03-29
CN1298714C (en) 2007-02-07
JP2001515895A (en) 2001-09-25
NO20001274L (en) 2000-05-10
PL193240B1 (en) 2007-01-31
ATE266654T1 (en) 2004-05-15
NO321835B1 (en) 2006-07-10
SK284974B6 (en) 2006-03-02
HU228986B1 (en) 2013-07-29
JP2010090157A (en) 2010-04-22
CN1284763C (en) 2006-11-15
JP5016621B2 (en) 2012-09-05
PT1015441E (en) 2004-08-31
WO1999012919A1 (en) 1999-03-18
CN1511820A (en) 2004-07-14
JP5266194B2 (en) 2013-08-21
HUP0003593A3 (en) 2002-12-28
DK1015441T3 (en) 2004-07-26
DE69823844D1 (en) 2004-06-17
NZ503338A (en) 2002-03-01
HK1030418A1 (en) 2001-05-04
KR100569771B1 (en) 2006-04-11
SK2262000A3 (en) 2000-10-09
CA2300204A1 (en) 1999-03-18
RU2003131081A (en) 2005-04-10
CN1268947A (en) 2000-10-04
CN1990452A (en) 2007-07-04
ES2221199T3 (en) 2004-12-16
FI120973B (en) 2010-05-31
JP4462760B2 (en) 2010-05-12
RU2223958C2 (en) 2004-02-20
RU2263106C2 (en) 2005-10-27
CA2300204C (en) 2006-12-12
CZ298847B6 (en) 2008-02-27
US6265604B1 (en) 2001-07-24
DE69823844T2 (en) 2005-04-14
EP1015441B1 (en) 2004-05-12
HK1063776A1 (en) 2005-01-14
US6077963A (en) 2000-06-20
NO20001274D0 (en) 2000-03-10
PL339138A1 (en) 2000-12-04
AU743496B2 (en) 2002-01-24
CZ2000804A3 (en) 2000-08-16
KR20010023864A (en) 2001-03-26
JP2009138002A (en) 2009-06-25
HUP0003593A2 (en) 2001-02-28
HK1104027A1 (en) 2008-01-04
EP1015441A1 (en) 2000-07-05

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