CA2647316C - Process for preparation of hiv protease inhibitors - Google Patents

Process for preparation of hiv protease inhibitors Download PDF

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Publication number
CA2647316C
CA2647316C CA2647316A CA2647316A CA2647316C CA 2647316 C CA2647316 C CA 2647316C CA 2647316 A CA2647316 A CA 2647316A CA 2647316 A CA2647316 A CA 2647316A CA 2647316 C CA2647316 C CA 2647316C
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Canada
Prior art keywords
formula
compound
combining
acid
mixture
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CA2647316A
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English (en)
French (fr)
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CA2647316A1 (en
Inventor
Kenneth R. Crawford
Eric D. Dowdy
Arnold Gutierrez
Richard P. Polniaszek
Richard Hung Chiu Yu
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Gilead Sciences Inc
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Gilead Sciences Inc
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Publication of CA2647316A1 publication Critical patent/CA2647316A1/en
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Publication of CA2647316C publication Critical patent/CA2647316C/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/38—Amides of thiocarboxylic acids
    • C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C327/42—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
    • 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
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • 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
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • 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
    • 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
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl compounds
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4084—Esters with hydroxyaryl compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Epidemiology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicinal Preparation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2647316A 2006-03-29 2007-03-29 Process for preparation of hiv protease inhibitors Active CA2647316C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US78712606P 2006-03-29 2006-03-29
US60/787,126 2006-03-29
PCT/US2007/007564 WO2007126812A2 (en) 2006-03-29 2007-03-29 Process for preparation of hiv protease inhibitors

Publications (2)

Publication Number Publication Date
CA2647316A1 CA2647316A1 (en) 2007-11-08
CA2647316C true CA2647316C (en) 2013-05-28

Family

ID=38323963

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2647316A Active CA2647316C (en) 2006-03-29 2007-03-29 Process for preparation of hiv protease inhibitors

Country Status (24)

Country Link
US (4) US8173623B2 (https=)
EP (2) EP1999133B1 (https=)
JP (2) JP5430395B2 (https=)
KR (2) KR101395377B1 (https=)
CN (2) CN101448838B (https=)
AP (2) AP2757A (https=)
AU (1) AU2007245194B2 (https=)
BR (1) BRPI0710199A2 (https=)
CA (1) CA2647316C (https=)
DK (1) DK1999133T3 (https=)
EA (2) EA016140B1 (https=)
ES (2) ES2430557T3 (https=)
HR (2) HRP20080554B1 (https=)
IL (2) IL194122A (https=)
MX (1) MX2008012398A (https=)
NO (2) NO342102B1 (https=)
NZ (2) NZ596074A (https=)
PL (1) PL1999133T3 (https=)
PT (1) PT1999133E (https=)
SG (1) SG170794A1 (https=)
SI (1) SI1999133T1 (https=)
UA (1) UA97241C2 (https=)
WO (1) WO2007126812A2 (https=)
ZA (1) ZA200808046B (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015123282A1 (en) * 2014-02-12 2015-08-20 Fotsing Joseph R Improved process for the synthesis of substituted 1-benzyl-3-(1-(isoxazol-4-ylmethyl)-1h-pyrazol-4-yl)imidazolidine-2,4-diones

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8921415B2 (en) 2009-01-29 2014-12-30 Mapi Pharma Ltd. Polymorphs of darunavir
PL2528923T3 (pl) 2010-01-28 2015-01-30 Mapi Pharma Ltd Sposób wytwarzania darunawiru i pochodnych darunawiru
CN102190638A (zh) * 2010-03-16 2011-09-21 中国科学院上海药物研究所 联芳基醇二胺类化合物、其药物组合物、制备方法及应用
CN102584748B (zh) * 2011-01-13 2015-02-11 浙江九洲药业股份有限公司 夫沙那韦中间体的制备方法
EP2702045B1 (en) * 2011-04-26 2017-10-18 Mylan Laboratories Ltd. Novel process for the preparation of etravirine
EP2634180A1 (en) 2012-03-01 2013-09-04 Lonza Ltd. Enzymatic process for the preparation of butyrolactones
SI3333173T1 (sl) 2012-10-03 2019-08-30 Gilead Sciences, Inc. Postopki za pripravo analogov protivirusnega nukleotida
CN103664976B (zh) * 2013-12-12 2015-11-04 惠州市莱佛士制药技术有限公司 一种顺式六氢呋喃并[2,3-b]呋喃-3-醇的制备方法
DK3236972T3 (en) 2014-12-26 2021-10-04 Univ Emory Antivirale N4-hydroxycytidin-derivativer
JP6435907B2 (ja) * 2015-02-16 2018-12-12 住友化学株式会社 ヘキサヒドロフロフラノール誘導体の製造方法
CN108610227B (zh) * 2016-12-10 2021-02-09 中国科学院大连化学物理研究所 一种制备双环芳香化合物的方法
JP6804790B1 (ja) 2017-12-07 2020-12-23 エモリー ユニバーシティー Ｎ４−ヒドロキシシチジンおよび誘導体ならびにそれらに関連する抗ウイルス用途
SG11202107145SA (en) 2019-01-25 2021-08-30 Univ Brown Compositions and methods for treating, preventing or reversing age-associated inflammation and disorders

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU6828894A (en) * 1993-05-14 1994-12-12 Merck & Co., Inc. Hiv protease inhibitors
AU1369001A (en) * 1995-12-13 2001-03-22 Abbott Laboratories Retroviral protease inhibiting compounds
EP2314563A3 (en) 1999-12-23 2012-04-04 Ampac Fine Chemicals LLC Improved preparation of 2S,3S-N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide hydrochloride and other derivatives of 2-hydroxy-1,3-diamines
AU2002255473A1 (en) * 2000-10-24 2002-09-04 Glaxo Group Limited Process for preparing intermediates of hiv protease inhibitors
CN1561570A (zh) 2001-07-20 2005-01-05 皇家菲利浦电子有限公司 振荡电路、具有这种振荡电路的变换器以及具有这种变换器的预调节器
AU2003231765B9 (en) * 2002-04-26 2010-01-28 Gilead Sciences, Inc. Cellular accumulation of phosphonate analogs of HIV protease inhibitor compounds and the compounds as such
US20050239054A1 (en) * 2002-04-26 2005-10-27 Arimilli Murty N Method and compositions for identifying anti-HIV therapeutic compounds
US7273716B2 (en) * 2003-04-25 2007-09-25 Gilead Sciences, Inc. Methods and compositions for identifying therapeutic compounds with GS-7340 ester hydrolase

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015123282A1 (en) * 2014-02-12 2015-08-20 Fotsing Joseph R Improved process for the synthesis of substituted 1-benzyl-3-(1-(isoxazol-4-ylmethyl)-1h-pyrazol-4-yl)imidazolidine-2,4-diones

Also Published As

Publication number Publication date
NZ571302A (en) 2011-11-25
PL1999133T3 (pl) 2014-01-31
EA020088B1 (ru) 2014-08-29
EA200802074A1 (ru) 2009-02-27
NO20180086A1 (no) 2008-12-22
US20080004242A1 (en) 2008-01-03
PT1999133E (pt) 2013-10-16
AP2008004641A0 (en) 2008-10-31
WO2007126812A3 (en) 2007-12-21
HRP20140626A2 (hr) 2014-11-07
NZ596074A (en) 2013-03-28
KR20080108322A (ko) 2008-12-12
IL225167A (en) 2016-03-31
HRP20080554B1 (hr) 2014-11-21
AU2007245194A1 (en) 2007-11-08
UA97241C2 (uk) 2012-01-25
CN101448838B (zh) 2012-07-04
SG170794A1 (en) 2011-05-30
EP2570416A1 (en) 2013-03-20
AP2013006690A0 (en) 2013-01-31
CN102516259A (zh) 2012-06-27
CN102516259B (zh) 2014-12-10
US8173623B2 (en) 2012-05-08
SI1999133T1 (sl) 2013-10-30
ES2572001T3 (es) 2016-05-27
KR101395377B1 (ko) 2014-05-14
JP5430395B2 (ja) 2014-02-26
CN101448838A (zh) 2009-06-03
EA016140B1 (ru) 2012-02-28
CA2647316A1 (en) 2007-11-08
US20120258935A1 (en) 2012-10-11
US8431745B2 (en) 2013-04-30
JP2013082717A (ja) 2013-05-09
ZA200808046B (en) 2009-06-24
EP1999133A2 (en) 2008-12-10
NO342102B1 (no) 2018-03-26
DK1999133T3 (da) 2013-11-25
US20130172295A1 (en) 2013-07-04
ES2430557T3 (es) 2013-11-21
NO342965B1 (no) 2018-09-10
BRPI0710199A2 (pt) 2012-03-06
AP2757A (en) 2013-09-30
JP2009531441A (ja) 2009-09-03
MX2008012398A (es) 2008-12-17
IL194122A (en) 2016-08-31
NO20084547L (no) 2008-12-22
KR101429300B1 (ko) 2014-08-11
WO2007126812A2 (en) 2007-11-08
HRP20080554A2 (hr) 2009-02-28
EA201100994A1 (ru) 2012-03-30
AU2007245194B2 (en) 2013-03-14
KR20140021047A (ko) 2014-02-19
US20110065631A1 (en) 2011-03-17
HK1180311A1 (en) 2013-10-18
HK1126756A1 (en) 2009-09-11
EP2570416B1 (en) 2016-03-16
EP1999133B1 (en) 2013-08-21

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