CA2560489C - Pyranone compounds useful to treat retroviral infections - Google Patents

Pyranone compounds useful to treat retroviral infections Download PDF

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Publication number
CA2560489C
CA2560489C CA002560489A CA2560489A CA2560489C CA 2560489 C CA2560489 C CA 2560489C CA 002560489 A CA002560489 A CA 002560489A CA 2560489 A CA2560489 A CA 2560489A CA 2560489 C CA2560489 C CA 2560489C
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CA
Canada
Prior art keywords
methyl
phenyl
formula
hydroxy
cyclopropyl
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.)
Expired - Lifetime
Application number
CA002560489A
Other languages
English (en)
French (fr)
Other versions
CA2560489A1 (en
Inventor
Karen Rene Romines
Gordon L. Bundy
Theresa M. Schwartz
Ruben A. Tommasi
Joseph Walter Strohbach
Steven Ronald Turner
Suvit Thaisrivongs
Paul Adrian Aristoff
Paul D. Johnson
Harvey Irving Skulnick
Louis L. Skaletzky
David John Anderson
Joel Morris
Ronald B. Gammill
George P. Luke
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.)
Pharmacia and Upjohn Co LLC
Original Assignee
Pharmacia and Upjohn Co LLC
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 Pharmacia and Upjohn Co LLC filed Critical Pharmacia and Upjohn Co LLC
Publication of CA2560489A1 publication Critical patent/CA2560489A1/en
Application granted granted Critical
Publication of CA2560489C publication Critical patent/CA2560489C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • A61K31/365—Lactones
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
    • 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
    • C07D405/14—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 three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CA002560489A 1994-05-06 1995-05-04 Pyranone compounds useful to treat retroviral infections Expired - Lifetime CA2560489C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US349,361 1989-05-09
US23881794A 1994-05-06 1994-05-06
US238,817 1994-05-06
US34936194A 1994-12-02 1994-12-02
CA002187523A CA2187523C (en) 1994-05-06 1995-05-04 Pyranone compounds useful to treat retroviral infections

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA002187523A Division CA2187523C (en) 1994-05-06 1995-05-04 Pyranone compounds useful to treat retroviral infections

Publications (2)

Publication Number Publication Date
CA2560489A1 CA2560489A1 (en) 1995-11-16
CA2560489C true CA2560489C (en) 2010-01-12

Family

ID=26931995

Family Applications (2)

Application Number Title Priority Date Filing Date
CA002560489A Expired - Lifetime CA2560489C (en) 1994-05-06 1995-05-04 Pyranone compounds useful to treat retroviral infections
CA002187523A Expired - Lifetime CA2187523C (en) 1994-05-06 1995-05-04 Pyranone compounds useful to treat retroviral infections

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA002187523A Expired - Lifetime CA2187523C (en) 1994-05-06 1995-05-04 Pyranone compounds useful to treat retroviral infections

Country Status (32)

Country Link
US (2) US5852195A (forum.php)
EP (1) EP0758327B1 (forum.php)
JP (1) JP3883206B2 (forum.php)
KR (1) KR100445929B1 (forum.php)
CN (2) CN1154642C (forum.php)
AT (1) ATE236894T1 (forum.php)
AU (2) AU701965B2 (forum.php)
BR (1) BR9507615A (forum.php)
CA (2) CA2560489C (forum.php)
CO (1) CO4810313A1 (forum.php)
CZ (1) CZ296515B6 (forum.php)
DE (2) DE69530294T2 (forum.php)
DK (1) DK0758327T3 (forum.php)
ES (1) ES2192201T3 (forum.php)
FI (1) FI117387B (forum.php)
FR (1) FR05C0047I2 (forum.php)
HU (1) HU228057B1 (forum.php)
IL (3) IL129871A (forum.php)
LU (1) LU91220I2 (forum.php)
MX (1) MX9605391A (forum.php)
MY (2) MY149862A (forum.php)
NL (1) NL300216I2 (forum.php)
NO (2) NO315799B1 (forum.php)
NZ (1) NZ285510A (forum.php)
PE (1) PE23196A1 (forum.php)
PL (1) PL190540B1 (forum.php)
PT (1) PT758327E (forum.php)
RU (1) RU2139284C1 (forum.php)
SI (1) SI0758327T1 (forum.php)
SK (1) SK284407B6 (forum.php)
TW (1) TW504507B (forum.php)
WO (1) WO1995030670A2 (forum.php)

Families Citing this family (74)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US5914332A (en) 1995-12-13 1999-06-22 Abbott Laboratories Retroviral protease inhibiting compounds
ES2208923T3 (es) * 1996-07-03 2004-06-16 PHARMACIA & UPJOHN COMPANY Distribucion blanco de medicamentos con la ayuda de derivados de sulfonamidas.
US5834506A (en) * 1996-11-01 1998-11-10 Warner-Lambert Company Dihydropyrones with improved antiviral activity
US6232333B1 (en) 1996-11-21 2001-05-15 Abbott Laboratories Pharmaceutical composition
ATE265847T1 (de) * 1997-07-29 2004-05-15 Upjohn Co Selbstemulgierbare formulierung enthaltend lipophile verbindungen
NZ502567A (en) 1997-07-29 2002-03-28 Upjohn Co Self-emulsifying formulation for lipophilic compounds containing a pyranone and a mixture of monoglycerides and diglycerides
NZ502566A (en) * 1997-07-29 2002-03-28 Upjohn Co Pharmaceutical composition for acidic lipophilic compounds in a form of a self-emulsifying formulation containing a pyranone and a basic amine
ATE266654T1 (de) * 1997-09-11 2004-05-15 Upjohn Co Verfahren zur herstellung von als protease inhibitoren wervollen 4-hydroxy-2-oxo-pyran- derivaten
EP1161427B1 (en) * 1999-03-18 2002-10-23 PHARMACIA & UPJOHN COMPANY Improved process for asymmetric hydrogenation
US6956048B2 (en) * 1999-03-31 2005-10-18 Pharmacia & Upjohn Company Pharmaceutical emulsions for retroviral protease inhibitors
AU1940501A (en) 2000-01-19 2001-07-31 Abbott Laboratories Improved pharmaceutical formulations
FI113942B (fi) * 2000-08-18 2004-07-15 Control Ox Oy Kasviperäisten fenolisten yhdisteiden käyttö valmistettaessa klamydiainfektion hoidossa ja ennaltaehkäisyssä käyttökelpoista farmaseuttista valmistetta, terveyteen myönteisesti vaikuttavaa ravintoainekoostumusta tai koostumusta lisättäväksi tällaisiin elintarvikkeisiin
DE10108470A1 (de) * 2001-02-22 2002-09-05 Boehringer Ingelheim Pharma Verfahren zur Herstellung optisch aktiver Dihydropyrone
US6500963B2 (en) 2001-02-22 2002-12-31 Boehringer Ingelheim Pharma Kg Process for preparing optically active dihydropyrones
AU2003209990B8 (en) * 2002-02-25 2008-10-30 Kudos Pharmaceuticals Ltd Pyranones useful as ATM inhibitors
MXPA04009672A (es) * 2002-04-01 2004-11-12 Pfizer Inhibidores de la rna polimerasa dependiente del rna del virus de la hepatitis c, y las composiciones y los tratamientos que usan los mismos.
RU2234535C2 (ru) * 2002-10-03 2004-08-20 Государственный научный центр вирусологии и биотехнологии "Вектор" Субстрат для определения активности интегразы вируса иммунодефицита человека
US8377952B2 (en) 2003-08-28 2013-02-19 Abbott Laboratories Solid pharmaceutical dosage formulation
US8025899B2 (en) 2003-08-28 2011-09-27 Abbott Laboratories Solid pharmaceutical dosage form
US8841326B2 (en) 2004-02-12 2014-09-23 Stc.Unm Therapeutic curcumin derivatives
IL161586A (en) * 2004-04-22 2015-02-26 Rafael Advanced Defense Sys Irreplaceable energetic material and reactive shielding that uses it
WO2006052373A2 (en) * 2004-11-08 2006-05-18 Boehringer Ingelheim International Gmbh Method for treating hiv infection through co-administration of tipranavir and etravirine
JP2008520672A (ja) * 2004-11-16 2008-06-19 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング チプラナビルとダルナビルの共投与によるｈｉｖ感染症の治療方法
US20060122220A1 (en) * 2004-11-19 2006-06-08 Boehringer Ingelheim International Gmbh Method for treating HIV infection through co-administration of tipranavir and UK-427,857
US20060128733A1 (en) * 2004-11-19 2006-06-15 Boehringer Ingelheim International Gmbh Method for treating HIV infection through co-administration of tipranavir and reverset
CA2586501A1 (en) * 2004-12-01 2006-06-08 Boehringer Ingelheim International Gmbh Method for treating hiv infection through co-administration of tipranavir and gw695634
JP2008521898A (ja) * 2004-12-01 2008-06-26 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング チプラナビル及びｇｗ８７３１４０を共に投与することを含むｈｉｖ感染症の治療方法
US20060135563A1 (en) * 2004-12-01 2006-06-22 Boehringer Ingelheim International Gmbh Method for treating HIV infection through co-administration of tipranavir and SCH-417690
CN101631568B (zh) 2007-03-12 2012-08-22 尼克塔治疗公司 低聚物-蛋白酶抑制剂偶联物
US20090062346A1 (en) * 2007-08-29 2009-03-05 Protia, Llc Deuterium-enriched tipranavir
US20100093811A1 (en) * 2007-09-25 2010-04-15 Coburn Craig A Hiv protease inhibitors
KR101076680B1 (ko) * 2007-11-01 2011-10-26 한미홀딩스 주식회사 (6ｒ)-3-헥실-4-히드록시-6-운데실-5,6-다이히드로피란-2-온의 제조방법 및 이에 사용되는 중간체
WO2009145814A2 (en) * 2008-03-10 2009-12-03 Vertex Pharmaceuticals Incorporated Pyrimidines and pyridines useful as inhibitors of protein kinases
WO2009114151A1 (en) 2008-03-12 2009-09-17 Nektar Therapeutics Oligomer-amino acid and olgomer-atazanavir conjugates
US8173621B2 (en) 2008-06-11 2012-05-08 Gilead Pharmasset Llc Nucleoside cyclicphosphates
TW201026716A (en) 2008-12-23 2010-07-16 Pharmasset Inc Nucleoside analogs
KR20110099138A (ko) 2008-12-23 2011-09-06 파마셋 인코포레이티드 뉴클레오시드 포스포르아미데이트
US8716263B2 (en) 2008-12-23 2014-05-06 Gilead Pharmasset Llc Synthesis of purine nucleosides
US8497383B2 (en) 2009-05-27 2013-07-30 Merck Sharp & Dohme Corp. HIV protease inhibitors
JP2012530069A (ja) 2009-06-12 2012-11-29 ネクター セラピューティックス プロテアーゼ阻害剤、水溶性非ペプチドオリゴマーおよび親油性部分を含む共有結合体
GEP20156325B (en) 2009-06-17 2015-07-10 Vertex Pharma Inhibitors of influenza viruses replication
KR101466245B1 (ko) * 2010-01-15 2014-12-01 한미사이언스 주식회사 테트라졸 메탄설폰산 염의 제조방법 및 이에 사용되는 신규 화합물
EP2752422B1 (en) 2010-03-31 2017-08-16 Gilead Pharmasset LLC Stereoselective synthesis of phosphorus containing actives
US8772332B2 (en) * 2010-09-09 2014-07-08 Richard H. Ebright Arylpropionyl-alpha-pyrone antibacterial agents
WO2012033846A1 (en) 2010-09-09 2012-03-15 Rutgers, The State University Of New Jersey Arylpropionyl-triketone antibacterial agents
US9133155B2 (en) 2010-09-17 2015-09-15 Rutgers, The State University Of New Jersey Antibacterial agents: high-potency myxopyronin derivatives
US9079834B2 (en) 2010-10-28 2015-07-14 Merck Canada Inc. HIV protease inhibitors
CA2822057A1 (en) 2010-12-16 2012-06-21 Vertex Pharmaceuticals Incorporated Inhibitors of influenza viruses replication
UA118010C2 (uk) * 2011-08-01 2018-11-12 Вертекс Фармасьютікалз Інкорпорейтед Інгібітори реплікації вірусів грипу
US9133157B2 (en) 2011-10-26 2015-09-15 Merck Canada Inc. HIV protease inhibitors
US9517994B2 (en) 2012-01-05 2016-12-13 Rutgers, The State University Of New Jersey Antibacterial agents: phloroglucinol derivatives
WO2014043019A1 (en) 2012-09-11 2014-03-20 Merck Sharp & Dohme Corp. Hiv protease inhibitors
EP2912047B1 (en) 2012-10-29 2016-08-24 Cipla Limited Antiviral phosphonate analogues and process for preparation thereof
WO2015013835A1 (en) 2013-07-31 2015-02-05 Merck Sharp & Dohme Corp. Piperazine derivatives as hiv protease inhibitors
HRP20191525T1 (hr) 2013-11-13 2019-11-29 Vertex Pharma Inhibitori replikacije virusa influence
HUE052178T2 (hu) 2013-11-13 2021-04-28 Vertex Pharma Eljárások influenzavírus-replikáció inhibitorainak elõállítására
WO2015095265A1 (en) 2013-12-19 2015-06-25 Merck Sharp & Dohme Corp. Hiv protease inhibitors
US9834526B2 (en) 2013-12-19 2017-12-05 Merck Sharp & Dohme Corp. HIV protease inhibitors
EP3113780B1 (en) 2014-03-06 2019-08-14 Merck Sharp & Dohme Corp. Hiv protease inhibitors
EP3116862B1 (en) 2014-03-10 2019-04-17 Merck Sharp & Dohme Corp. Piperazine derivatives as hiv protease inhibitors
EP3212196A4 (en) 2014-10-29 2018-07-11 Wisconsin Alumni Research Foundation Boronic acid inhibitors of hiv protease
JP6704416B2 (ja) 2015-05-13 2020-06-03 バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ インフルエンザウイルスの複製の阻害剤を調製する方法
MA42422A (fr) 2015-05-13 2018-05-23 Vertex Pharma Inhibiteurs de la réplication des virus de la grippe
US10450292B2 (en) 2015-12-10 2019-10-22 Rutgers, The State University of New Jersesy Inhibitors of bacterial RNA polymerase: arylpropanoyl, arylpropenoyl, and arylcyclopropanecarboxyl phloroglucinols
WO2017156458A1 (en) * 2016-03-11 2017-09-14 University Of South Florida Beta-lactamase inhibitors, formulations, and uses thereof
US11993590B2 (en) * 2016-12-04 2024-05-28 712 North Inc. Pyranone compounds useful to modulate OMA1 protease
CN112118837B (zh) 2018-02-13 2024-07-09 罗格斯新泽西州立大学 抗菌剂：o-烷基氘化派洛宁
US12209082B2 (en) 2018-02-13 2025-01-28 Rutgers, The State University Of New Jersey Antibacterial agents: soluble salts and aqueous formulations of pyronins
US11572337B2 (en) 2018-03-06 2023-02-07 Rutgers, The State University Of New Jersey Antibacterial agents: arylalkylcarboxamido phloroglucinols
CN110551090B (zh) * 2019-10-21 2021-06-18 扬州工业职业技术学院 一种超声波提取中药狗脊中抗肿瘤活性成分的方法
WO2021209563A1 (en) 2020-04-16 2021-10-21 Som Innovation Biotech, S.A. Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus
WO2024130166A2 (en) * 2022-12-16 2024-06-20 Denali Therapeutics Inc. Compounds, compositions, and methods
CN116730993A (zh) * 2023-04-25 2023-09-12 浙江科技学院 一种替拉那韦中间体及替拉那韦的制备方法

Family Cites Families (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB193507A (en) 1921-11-25 1923-02-26 English Electric Co Ltd Improvements in and connected with hydraulic impulse turbines
NL80964C (forum.php) * 1952-03-08
NL83407C (forum.php) * 1952-05-16
US2723277A (en) * 1952-08-26 1955-11-08 Hoffmann La Roche Malonic acid derivatives and process for the manufacture thereof
US2872457A (en) * 1956-04-19 1959-02-03 Wisconsin Alumni Res Found Process for the preparation of 4-hydroxycoumarin derivatives
GB836740A (en) * 1956-04-25 1960-06-09 Bayer Ag Coumarin derivatives and their production
FR1276654A (fr) * 1958-10-01 1961-11-24 Nouveaux dérivés de l'hydroxy-4-alpha-2-pyrone
FR1463767A (fr) * 1963-04-03 1966-07-22 Clin Byla Ets Dérivés de la coumarine et leur préparation
BE674997A (forum.php) * 1965-01-13 1966-07-12
FR1559595A (forum.php) * 1966-12-13 1969-03-14
US3489774A (en) * 1967-04-24 1970-01-13 Dow Chemical Co 3-(beta-aryl-beta-(arylthio) (or arylseleno) propionyl)-coumarin products
US3493586A (en) * 1969-01-23 1970-02-03 Dow Chemical Co 3-(beta-aryl-beta-(arylthio) (or arylseleno)-propionyl)pyrone products
JPS4823942B1 (forum.php) * 1969-02-14 1973-07-17
US3764693A (en) * 1969-11-21 1973-10-09 Lipha A rodenticidal compositions containing 4-hydroxy coumarins
US3835161A (en) * 1972-10-24 1974-09-10 Realisations Scient S E Res C 3-substituted-4-hydroxy-coumarins
US3931235A (en) * 1972-12-18 1976-01-06 The Dow Chemical Company Process for preparing sulfur-containing hydroxy pyrones
JPS53147073A (en) * 1977-05-24 1978-12-21 Sankyo Co Ltd Mevalonolactone derivatives
NZ194557A (en) * 1979-08-17 1984-09-28 Merck & Co Inc Substituted pyranone derivatives;dihydroxy acids therefrom;pharmaceutical compositions
CA1171424A (en) * 1981-06-17 1984-07-24 Alvin K. Willard ( )-(4r, 6s) - (e)-6-[2-(4'fluro-3,3', 5-trimethyl- [l,l'-biphenyl]-2-yl)ethenyl]-3,4,5,6- tetrahydro-4-hydroxy-2h-pyran-2-one
JPS634652A (ja) * 1986-06-25 1988-01-09 Hitachi Ltd 半導体装置
WO1988004652A1 (en) 1986-12-17 1988-06-30 Nippon Soda Co., Ltd. Heterocyclic compounds having triketo skeleton
US4900754A (en) * 1987-12-21 1990-02-13 Rorer Pharmaceutical Corp. HMG-COA reductase inhibitors
WO1989007939A2 (en) * 1988-03-01 1989-09-08 The Upjohn Company Coumarins to inhibit reverse transcriptase in humans
DE3929913A1 (de) * 1989-09-08 1991-04-04 Hoechst Ag 4-hydroxytetrahydropyran-2-one sowie die entsprechenden dihydroxycarbonsaeurederivate, salze und ester, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate sowie vorprodukte
EP0494231A4 (en) * 1989-09-26 1992-09-16 The Regents Of The University Of California 6-amino-1,2-benzopyrones useful for treatment of viral diseases
JPH05501879A (ja) * 1989-10-27 1993-04-08 ジ・アップジョン・カンパニー Ｈｉｖおよび他のレトロウイルスを処理する方法およびそれに有用な化合物
JPH03227923A (ja) 1990-01-30 1991-10-08 Sawai Seiyaku Kk ひと免疫不全ウイルス疾患処置剤
SE9000624D0 (sv) * 1990-02-22 1990-02-22 Pharmacia Ab New use
CA2035972C (en) * 1990-02-23 2006-07-11 Martin Karpf Process for the preparation of oxetanones
AU8448491A (en) * 1990-09-07 1992-03-30 Schering Corporation Antiviral compounds and antihypertensive compounds
DE69128481T2 (de) * 1990-09-07 1998-04-09 Schering Corp Antivirale und antihypertensive verbindungen
WO1992004326A1 (en) * 1990-09-07 1992-03-19 Schering Corporation Antiviral compounds
US5484951A (en) * 1990-10-19 1996-01-16 Octamer, Incorporated 5-iodo-6-amino-6-nitroso-1,2-benzopyrones useful as cytostatic and antiviral agents
AU1748792A (en) * 1991-04-04 1992-11-02 Upjohn Company, The Phosphorus containing compounds as inhibitors of retroviruses
ES2104946T3 (es) * 1991-10-11 1997-10-16 Du Pont Merck Pharma Ureas ciclicas y similares utiles como inhibidores de la proteasa retrovirica.
AU676992B2 (en) * 1991-10-22 1997-04-10 Emory University Adenosine diphosphoribose polymerase binding nitroso aromatic compounds useful as anti-tumor and anti-retroviral agents
DE4308451A1 (de) * 1992-09-10 1994-04-14 Bayer Ag 3-Aryl-pyron-Derivate
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
IL108459A0 (en) * 1993-02-05 1994-04-12 Opjohn Company 4-Hydroxy-benzopyran-2-ones and 4-hydroxy-cycloalkyl [B] pyran-2-ones useful for treating infections due to hiv and other retroviruses
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

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