CA2878699C - Process and intermediates for preparing integrase inhibitors - Google Patents

Process and intermediates for preparing integrase inhibitors Download PDF

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Publication number
CA2878699C
CA2878699C CA2878699A CA2878699A CA2878699C CA 2878699 C CA2878699 C CA 2878699C CA 2878699 A CA2878699 A CA 2878699A CA 2878699 A CA2878699 A CA 2878699A CA 2878699 C CA2878699 C CA 2878699C
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CA
Canada
Prior art keywords
compound
formula
salt
ome
mixture
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 - Fee Related
Application number
CA2878699A
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English (en)
French (fr)
Other versions
CA2878699A1 (en
Inventor
Dominika Pcion
Carrie TOMASI
Mark Charles Whitcomb
Eric D. Dowdy
Wenyi FU
Patricia Macleod
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Gilead Sciences Inc
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Gilead Sciences Inc
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 Gilead Sciences Inc filed Critical Gilead Sciences Inc
Publication of CA2878699A1 publication Critical patent/CA2878699A1/en
Application granted granted Critical
Publication of CA2878699C publication Critical patent/CA2878699C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/20Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/257Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/29Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
    • 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
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46Friedel-Crafts reactions
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/12Preparation of carboxylic acid esters from asymmetrical anhydrides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Quinoline Compounds (AREA)
CA2878699A 2012-08-03 2013-08-01 Process and intermediates for preparing integrase inhibitors Expired - Fee Related CA2878699C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261679475P 2012-08-03 2012-08-03
US61/679,475 2012-08-03
PCT/US2013/053295 WO2014022707A1 (en) 2012-08-03 2013-08-01 Process and intermediates for preparing integrase inhibitors

Publications (2)

Publication Number Publication Date
CA2878699A1 CA2878699A1 (en) 2014-02-06
CA2878699C true CA2878699C (en) 2018-09-11

Family

ID=48980354

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2878699A Expired - Fee Related CA2878699C (en) 2012-08-03 2013-08-01 Process and intermediates for preparing integrase inhibitors

Country Status (17)

Country Link
US (1) US8877931B2 (instruction)
EP (1) EP2880017B1 (instruction)
JP (1) JP6147856B2 (instruction)
KR (1) KR20150040340A (instruction)
CN (1) CN104520275B (instruction)
AU (1) AU2013296289B2 (instruction)
BR (1) BR112015002275A2 (instruction)
CA (1) CA2878699C (instruction)
EA (1) EA026089B1 (instruction)
ES (1) ES2608860T3 (instruction)
IL (1) IL236618A (instruction)
IN (1) IN2015DN01688A (instruction)
MX (1) MX337094B (instruction)
NZ (1) NZ630199A (instruction)
PT (1) PT2880017T (instruction)
SG (1) SG11201500812QA (instruction)
WO (1) WO2014022707A1 (instruction)

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SI3067358T1 (sl) 2012-12-21 2019-12-31 Gilead Sciences, Inc. Policiklične spojine karbamoilpiridona in njihova farmacevtska uporaba
WO2015006731A1 (en) 2013-07-12 2015-01-15 Gilead Sciences, Inc. Polycyclic-carbamoylpyridone compounds and their use for the treatment of hiv infections
NO2865735T3 (instruction) 2013-07-12 2018-07-21
TW201613936A (en) 2014-06-20 2016-04-16 Gilead Sciences Inc Crystalline forms of(2R,5S,13aR)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide
NO2717902T3 (instruction) 2014-06-20 2018-06-23
TWI677489B (zh) 2014-06-20 2019-11-21 美商基利科學股份有限公司 多環型胺甲醯基吡啶酮化合物之合成
TWI738321B (zh) 2014-12-23 2021-09-01 美商基利科學股份有限公司 多環胺甲醯基吡啶酮化合物及其醫藥用途
NZ735575A (en) 2015-04-02 2018-11-30 Gilead Sciences Inc Polycyclic-carbamoylpyridone compounds and their pharmaceutical use
CA3160068A1 (en) * 2019-09-24 2021-04-01 Asymchem Laboratories (Tianjin) Co., Ltd. Continuous preparation method for benzylzinc halide and derivative thereof
CN112661698A (zh) * 2021-01-14 2021-04-16 浙江海森药业股份有限公司 一种艾维雷韦的制备方法

Family Cites Families (21)

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SE9904108D0 (sv) * 1999-11-15 1999-11-15 New Pharma Research Ab Nya föreningar
AU2002229057B2 (en) 2000-12-14 2005-04-21 Warner Chilcott Company, Llc Cyclization process step in the making of quinolones and naphthyridines
TW200300349A (en) 2001-11-19 2003-06-01 Sankyo Co A 4-oxoqinoline derivative
JPWO2003101916A1 (ja) 2002-05-31 2005-09-29 萬有製薬株式会社 ハロゲン−金属交換反応による置換基の導入法
US6803469B2 (en) 2002-08-05 2004-10-12 The Procter & Gamble Company Process for preparing quinolone antibiotic intermediates
TW200409759A (en) 2002-09-25 2004-06-16 Wyeth Corp Substituted 4-(indazol-3-yl)phenols
AU2003302029B8 (en) 2002-11-20 2006-08-17 Japan Tobacco Inc. 4-oxoquinoline compound and utilization thereof as HIV integrase inhibitor
EP1582523A1 (en) 2004-04-02 2005-10-05 Ludwig-Maximilians-Universität München Method of preparing organomagnesium compounds
EP1582524B1 (en) 2004-04-02 2008-08-13 Ludwig Maximilians Universität Method of preparing organomagnesium compounds
MY134672A (en) 2004-05-20 2007-12-31 Japan Tobacco Inc Stable crystal of 4-oxoquinoline compound
US7531554B2 (en) 2004-05-20 2009-05-12 Japan Tobacco Inc. 4-oxoquinoline compound and use thereof as HIV integrase inhibitor
JP4629104B2 (ja) 2004-05-21 2011-02-09 日本たばこ産業株式会社 4−オキソキノリン誘導体および抗hiv剤を含む併用剤
WO2007063869A1 (ja) 2005-11-30 2007-06-07 Japan Tobacco Inc. 高純度キノロン化合物の製造方法
US20090233964A1 (en) 2005-12-30 2009-09-17 Gilead Sciences, Inc. Methods for improving the pharmacokinetics of hiv integrase inhibitors
EA017861B9 (ru) 2006-03-06 2014-05-30 Джапан Тобакко Инк. Способ получения 4-оксохинолинового соединения
IN2014CN00532A (instruction) 2006-03-06 2015-04-03 Japan Tobacco Inc
TW200811153A (en) 2006-06-23 2008-03-01 Japan Tobacco Inc 6-(heterocyclyl-substituted benzyl)-4-oxoquinoline compound and use thereof as HIV integrase inhibitor
EP2644587A3 (en) 2006-09-12 2013-10-23 Gilead Sciences, Inc. Process and intermediates for preparing integrase inhibitors
CA2692101A1 (en) 2007-06-29 2009-01-08 Gilead Sciences, Inc. Combination of 6-(3-chloro-2-fluorobenzyl)-1-[(2s)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and a compound that inhibits a ugt pathway or ugt metabolism
MX2009013828A (es) 2007-06-29 2010-03-10 Gilead Sciences Inc Composiciones terapeuticas y su uso.
AR068403A1 (es) 2007-09-11 2009-11-18 Gilead Sciences Inc Proceso e intermediarios para la preparacion de inhibidores de integrasa

Also Published As

Publication number Publication date
IL236618A (en) 2017-04-30
JP2015524822A (ja) 2015-08-27
WO2014022707A1 (en) 2014-02-06
HK1209415A1 (en) 2016-04-01
NZ630199A (en) 2016-12-23
EP2880017B1 (en) 2016-10-05
AU2013296289A1 (en) 2015-02-19
KR20150040340A (ko) 2015-04-14
MX337094B (es) 2016-02-10
US20140039194A1 (en) 2014-02-06
BR112015002275A2 (pt) 2017-07-04
CN104520275B (zh) 2016-11-02
SG11201500812QA (en) 2015-04-29
PT2880017T (pt) 2016-12-14
JP6147856B2 (ja) 2017-06-14
IN2015DN01688A (instruction) 2015-07-03
CA2878699A1 (en) 2014-02-06
MX2015001506A (es) 2015-04-08
AU2013296289B2 (en) 2017-10-05
US8877931B2 (en) 2014-11-04
EA026089B1 (ru) 2017-02-28
EP2880017A1 (en) 2015-06-10
IL236618A0 (en) 2015-02-26
ES2608860T3 (es) 2017-04-17
EA201590018A1 (ru) 2015-05-29
CN104520275A (zh) 2015-04-15
HK1209748A1 (en) 2016-04-08

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Effective date: 20160801

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Effective date: 20200831