CA2711852C - Process for the manufacture of epoxybutanol intermediates - Google Patents

Process for the manufacture of epoxybutanol intermediates Download PDF

Info

Publication number
CA2711852C
CA2711852C CA2711852A CA2711852A CA2711852C CA 2711852 C CA2711852 C CA 2711852C CA 2711852 A CA2711852 A CA 2711852A CA 2711852 A CA2711852 A CA 2711852A CA 2711852 C CA2711852 C CA 2711852C
Authority
CA
Canada
Prior art keywords
formula
compound
mmol
reaction
solvent
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.)
Active
Application number
CA2711852A
Other languages
English (en)
French (fr)
Other versions
CA2711852A1 (en
Inventor
Marc Muller
Lin Xu
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.)
Basilea Pharmaceutica AG
Original Assignee
Basilea Pharmaceutica AG
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 Basilea Pharmaceutica AG filed Critical Basilea Pharmaceutica AG
Publication of CA2711852A1 publication Critical patent/CA2711852A1/en
Application granted granted Critical
Publication of CA2711852C publication Critical patent/CA2711852C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
    • 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
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • 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
    • A61K31/336—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having three-membered rings, e.g. oxirane, fumagillin
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Epoxy Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyrane Compounds (AREA)
CA2711852A 2005-12-01 2006-11-29 Process for the manufacture of epoxybutanol intermediates Active CA2711852C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP05026163 2005-12-01
EP05026163.5 2005-12-01
CA2629092A CA2629092C (en) 2005-12-01 2006-11-29 Process for the manufacture of epoxybutanol intermediates

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2629092A Division CA2629092C (en) 2005-12-01 2006-11-29 Process for the manufacture of epoxybutanol intermediates

Publications (2)

Publication Number Publication Date
CA2711852A1 CA2711852A1 (en) 2007-06-07
CA2711852C true CA2711852C (en) 2011-10-04

Family

ID=36178579

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2711852A Active CA2711852C (en) 2005-12-01 2006-11-29 Process for the manufacture of epoxybutanol intermediates
CA2629092A Active CA2629092C (en) 2005-12-01 2006-11-29 Process for the manufacture of epoxybutanol intermediates

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2629092A Active CA2629092C (en) 2005-12-01 2006-11-29 Process for the manufacture of epoxybutanol intermediates

Country Status (19)

Country Link
US (2) US7816537B2 (https=)
EP (2) EP2133345A1 (https=)
JP (1) JP5329969B2 (https=)
KR (1) KR101191682B1 (https=)
CN (1) CN101321522B (https=)
AT (1) ATE444747T1 (https=)
AU (2) AU2006319657B2 (https=)
BR (1) BRPI0619120B1 (https=)
CA (2) CA2711852C (https=)
CY (1) CY1110588T1 (https=)
DE (1) DE602006009698D1 (https=)
DK (1) DK1954264T3 (https=)
ES (1) ES2333258T3 (https=)
HR (1) HRP20090675T1 (https=)
PL (1) PL1954264T3 (https=)
PT (1) PT1954264E (https=)
SI (1) SI1954264T1 (https=)
WO (1) WO2007062542A2 (https=)
ZA (1) ZA200804218B (https=)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2012003126A (es) 2009-09-21 2012-06-19 Gilead Sciences Inc Procesos e intermedios para la preparacion de analogos de 1'-carbonucleosidos sustituidos.
ES2524356T3 (es) 2010-07-22 2014-12-05 Gilead Sciences, Inc. Métodos y compuestos para tratar infecciones provocadas por virus Paramyxoviridae
CA2878361C (en) 2012-08-07 2020-09-22 Basilea Pharmaceutica Ag Process for the manufacture of isavuconazole or ravuconazole
WO2015150947A1 (en) 2014-03-29 2015-10-08 Wockhardt Limited A process for the preparation of isavuconazole and its intermediates
TWI687432B (zh) 2014-10-29 2020-03-11 美商基利科學股份有限公司 絲狀病毒科病毒感染之治療
DK3785717T3 (da) 2015-09-16 2022-03-21 Gilead Sciences Inc Fremgangsmåder til behandling af coronaviridae-infektioner
CN105367528A (zh) * 2015-11-10 2016-03-02 南通诺泰生物医药技术有限公司 一种三唑类药物中间体(d)-1-(1-环烷仲胺基)-2-(2-四氢吡喃基)氧-1-丙酮类化合物及合成方法
US10682368B2 (en) 2017-03-14 2020-06-16 Gilead Sciences, Inc. Methods of treating feline coronavirus infections
CA3059777C (en) 2017-05-01 2023-02-21 Gilead Sciences, Inc. Crystalline forms of (s)-2-ethylbutyl 2-(((s)-(((2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f] [1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy) phosphoryl)amino)propanoate
WO2019014247A1 (en) 2017-07-11 2019-01-17 Gilead Sciences, Inc. COMPOSITIONS COMPRISING POLYMERASE RNA INHIBITOR AND CYCLODEXTRIN FOR THE TREATMENT OF VIRAL INFECTIONS
CN110997646B (zh) 2017-08-10 2023-06-20 住友化学株式会社 环氧醇化合物的制造方法
JP2023512656A (ja) 2020-01-27 2023-03-28 ギリアード サイエンシーズ， インコーポレイテッド ＳＡＲＳ ＣｏＶ－２感染を治療するための方法
KR20220153619A (ko) 2020-03-12 2022-11-18 길리애드 사이언시즈, 인코포레이티드 1'-시아노 뉴클레오사이드의 제조 방법
CA3172483A1 (en) 2020-04-06 2021-10-14 Scott Ellis Inhalation formulations of 1'-cyano substituted carbanucleoside analogs
TW202203941A (zh) 2020-05-29 2022-02-01 美商基利科學股份有限公司 瑞德西韋之治療方法
PE20230618A1 (es) 2020-06-24 2023-04-14 Gilead Sciences Inc Analogos de nucleosido de 1'-ciano y usos de los mismos
IL300453A (en) 2020-08-27 2023-04-01 Gilead Sciences Inc COMPOSITIONS AND METHODS FOR THE TREATMENT OF VIRAL INFECTIONS
KR20240154647A (ko) 2022-03-02 2024-10-25 길리애드 사이언시즈, 인코포레이티드 바이러스성 감염 치료를 위한 화합물 및 방법
US12357577B1 (en) 2024-02-02 2025-07-15 Gilead Sciences, Inc. Pharmaceutical formulations and uses thereof
CN115536643A (zh) * 2022-12-05 2022-12-30 南京桦冠生物技术有限公司 一种艾沙康唑类药物关键中间体的制备方法
CN119264078B (zh) * 2024-12-09 2025-08-01 浙江世佳科技股份有限公司 一种(5s,6r)-5,6-环氧-2-十七碳炔-1-醇的合成方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3452213B2 (ja) * 1994-07-05 2003-09-29 エーザイ株式会社 抗真菌剤及びその製造方法
AU2931399A (en) * 1998-03-06 1999-09-20 F. Hoffmann-La Roche Ag 3-(4-(4-cyanophenyl)thiazol-2-y))-1-(1h-1,2,4-triazol-1-yl) -butan-2-ol derivatives having antifungal activity
US6133485A (en) * 1998-04-15 2000-10-17 Synphar Laboratories, Inc. Asymmetric synthesis of 2-(2,4-difluorophenyl)-1-heterocycl-1-yl butan-2,3-diols
US6391903B1 (en) * 1999-09-09 2002-05-21 Sankyo Company, Limited Triazole derivatives having antifungal activity
US6884892B2 (en) 2002-06-20 2005-04-26 Sumitomo Chemical Company, Limited Production methods of epoxytriazole derivative and intermediate therefor
JP4627413B2 (ja) * 2003-05-06 2011-02-09 三井化学株式会社 １−アゾール−２−フェニル−２、３−プロパンジオール誘導体の製造法

Also Published As

Publication number Publication date
AU2010203301B2 (en) 2012-06-21
WO2007062542A2 (en) 2007-06-07
KR20080075014A (ko) 2008-08-13
CY1110588T1 (el) 2015-04-29
AU2010203301A1 (en) 2010-08-12
ES2333258T3 (es) 2010-02-18
PL1954264T3 (pl) 2010-02-26
HRP20090675T1 (hr) 2010-01-31
CA2629092C (en) 2012-01-03
BRPI0619120A2 (pt) 2011-09-13
CA2711852A1 (en) 2007-06-07
DE602006009698D1 (de) 2009-11-19
JP2009517413A (ja) 2009-04-30
CN101321522B (zh) 2012-05-30
AU2006319657B2 (en) 2010-08-12
EP1954264B1 (en) 2009-10-07
JP5329969B2 (ja) 2013-10-30
WO2007062542A3 (en) 2007-11-01
ATE444747T1 (de) 2009-10-15
US20110021794A1 (en) 2011-01-27
BRPI0619120B1 (pt) 2023-10-10
DK1954264T3 (da) 2010-01-11
CA2629092A1 (en) 2007-06-07
CN101321522A (zh) 2008-12-10
US8076494B2 (en) 2011-12-13
EP2133345A1 (en) 2009-12-16
US7816537B2 (en) 2010-10-19
EP1954264A2 (en) 2008-08-13
ZA200804218B (en) 2009-01-28
AU2006319657A1 (en) 2007-06-07
SI1954264T1 (sl) 2010-01-29
KR101191682B1 (ko) 2012-10-16
US20090299073A1 (en) 2009-12-03
PT1954264E (pt) 2009-12-23

Similar Documents

Publication Publication Date Title
US8076494B2 (en) Process for the manufacture of epoxy triazole derivatives
JP2009517413A5 (https=)
CN101180284B (zh) 从四氢吡喃-3-酮制备四氢吡喃的方法
EP1368334B1 (en) Process for preparing intermediates for the manufacture of discodermolide and discodermolide analogues
RU2656600C2 (ru) Способ получения производного фторлактона
JP2002511434A5 (https=)
JPH0641114A (ja) 新規メバロノラクトン類とその製法
KR20140065036A (ko) 고순도 보센탄의 개선된 제조방법
JPH1017561A (ja) アリルアルコール類およびその製造方法
EP1718591A1 (en) A process for the preparation of optically active cyclohexenones
JP2710837B2 (ja) 光学活性β―ヒドロキシチオエステルの製造方法
JPH0249311B2 (https=)
HU189674B (en) Improved process for preparing hydroxyethyl-tetrazole-thiol
KR20160126700A (ko) 스타틴의 중간체, 이의 제조방법 및 이를 이용한 로수바스타틴의 제조방법
WO2006083010A1 (ja) ４−アセチルピリミジン化合物の製造方法およびその結晶
JPH0597735A (ja) 光学活性二級アルコ−ルの製造方法
JPH0651694B2 (ja) 光学活性化合物
CA2435801A1 (en) Styrene derivative and process for preparing the same
HK1060882B (en) Process for preparing intermediates for the manufacture of discodermolide and discodermolide analogues
CZ86799A3 (cs) Způsob výroby substituovaných derivátů chromanolu a meziprodukty pro tyto způsoby
JPH0651691B2 (ja) 光学活性化合物

Legal Events

Date Code Title Description
EEER Examination request
W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20251029

H13 Ip right lapsed

Free format text: ST27 STATUS EVENT CODE: N-4-6-H10-H13-H100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE AND LATE FEE NOT PAID BY DEADLINE OF NOTICE

Effective date: 20260209

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: N-6-6-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260210