CA2544560C - Processes for preparing bicyclo [3.1.0] hexane derivatives, and intermediates thereto - Google Patents

Processes for preparing bicyclo [3.1.0] hexane derivatives, and intermediates thereto Download PDF

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Publication number
CA2544560C
CA2544560C CA2544560A CA2544560A CA2544560C CA 2544560 C CA2544560 C CA 2544560C CA 2544560 A CA2544560 A CA 2544560A CA 2544560 A CA2544560 A CA 2544560A CA 2544560 C CA2544560 C CA 2544560C
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CA
Canada
Prior art keywords
alkyl
alkoxy
unsubstituted
substituted
halogen
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
CA2544560A
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English (en)
French (fr)
Other versions
CA2544560A1 (en
Inventor
Frederick W. Hartner
Lushi Tan
Nobuyoshi Yasuda
Naoki Yoshikawa
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.)
Taisho Pharmaceutical Co Ltd
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Taisho Pharmaceutical Co Ltd
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Filing date
Publication date
Application filed by Taisho Pharmaceutical Co Ltd filed Critical Taisho Pharmaceutical Co Ltd
Publication of CA2544560A1 publication Critical patent/CA2544560A1/en
Application granted granted Critical
Publication of CA2544560C publication Critical patent/CA2544560C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C229/50—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms being part of the same condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • 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
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • 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
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2544560A 2003-11-07 2004-11-03 Processes for preparing bicyclo [3.1.0] hexane derivatives, and intermediates thereto Expired - Fee Related CA2544560C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US51839103P 2003-11-07 2003-11-07
US60/518,391 2003-11-07
PCT/US2004/036574 WO2005047215A2 (en) 2003-11-07 2004-11-03 Processes for preparing bicyclo [3.1.0] hexane derivatives, and intermediates thereto

Publications (2)

Publication Number Publication Date
CA2544560A1 CA2544560A1 (en) 2005-05-26
CA2544560C true CA2544560C (en) 2014-01-07

Family

ID=34590258

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2544560A Expired - Fee Related CA2544560C (en) 2003-11-07 2004-11-03 Processes for preparing bicyclo [3.1.0] hexane derivatives, and intermediates thereto

Country Status (10)

Country Link
US (1) US7786314B2 (enExample)
EP (1) EP1689727A4 (enExample)
JP (1) JP4742239B2 (enExample)
KR (1) KR101204145B1 (enExample)
CN (2) CN100475800C (enExample)
AU (1) AU2004289652B8 (enExample)
CA (1) CA2544560C (enExample)
RU (1) RU2388747C2 (enExample)
TW (1) TWI347316B (enExample)
WO (1) WO2005047215A2 (enExample)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5309680B2 (ja) * 2008-05-09 2013-10-09 大正製薬株式会社 フッ素化エステル化合物の製造方法及びその中間体
WO2009142184A1 (ja) * 2008-05-21 2009-11-26 大正製薬株式会社 酵素を用いたビシクロ［３．１．０］ヘキサン誘導体の製造方法
US8742161B2 (en) * 2009-11-18 2014-06-03 Taisho Pharmaceutical Co., Ltd Process for producing optically active bicyclo [3.1.0] hexane derivative using enzyme
CN112074505B (zh) 2018-03-08 2024-04-05 因赛特公司 作为PI3K-γ抑制剂的氨基吡嗪二醇化合物
US11046658B2 (en) 2018-07-02 2021-06-29 Incyte Corporation Aminopyrazine derivatives as PI3K-γ inhibitors

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2152925C1 (ru) * 1994-08-12 2000-07-20 Эли Лилли Энд Компани Производные аминобицикло[3.1.0]гексан-2,6-дикарбоновой кислоты и фармацевтическая композиция
US5661184A (en) 1994-08-12 1997-08-26 Eli Lilly And Company Psychiatric agents
ZA983930B (en) * 1997-05-14 1999-11-08 Lilly Co Eli Excitatory amino acid receptor modulators.
JP2000072731A (ja) * 1998-08-31 2000-03-07 Taisho Pharmaceut Co Ltd ４−置換−２−アミノビシクロ［３．１．０］ヘキサン−２，６−ジカルボン酸誘導体及び製薬用組成物
JP4194715B2 (ja) * 1998-08-31 2008-12-10 大正製薬株式会社 ６−フルオロビシクロ［３．１．０］ヘキサン誘導体
CN1247527C (zh) * 1998-08-31 2006-03-29 大正制药株式会社 6－氟双环[3.1.0]己烷衍生物
PE20001236A1 (es) 1998-11-13 2000-11-10 Lilly Co Eli Moduladores del receptor de aminoacidos excitadores
US6479674B1 (en) * 1999-03-25 2002-11-12 Taisho Pharmaceutical Co., Ltd. Carboxylic acid derivatives and process for producing same
AU6785501A (en) 2000-06-28 2002-01-08 Taisho Pharmaceutical Co Ltd Intermediate and process for producing fluorinated carboxylic acid derivative from the same
CA2441127A1 (en) * 2001-03-14 2002-09-19 Taisho Pharmaceutical Co., Ltd. Process for producing bicyclocarboxylic acid derivative

Also Published As

Publication number Publication date
EP1689727A2 (en) 2006-08-16
US20070112030A1 (en) 2007-05-17
JP4742239B2 (ja) 2011-08-10
CA2544560A1 (en) 2005-05-26
HK1096971A1 (en) 2007-06-15
RU2006119924A (ru) 2007-12-27
EP1689727A4 (en) 2008-12-31
TW200530178A (en) 2005-09-16
KR101204145B1 (ko) 2012-11-22
WO2005047215A2 (en) 2005-05-26
CN100475800C (zh) 2009-04-08
JP2007513070A (ja) 2007-05-24
CN101654410B (zh) 2013-03-06
CN1898224A (zh) 2007-01-17
AU2004289652B8 (en) 2011-01-20
CN101654410A (zh) 2010-02-24
TWI347316B (en) 2011-08-21
US7786314B2 (en) 2010-08-31
AU2004289652A1 (en) 2005-05-26
KR20060131771A (ko) 2006-12-20
HK1139124A1 (en) 2010-09-10
AU2004289652B2 (en) 2010-09-16
RU2388747C2 (ru) 2010-05-10
WO2005047215A3 (en) 2005-07-14

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