CA2337452C - Process for the preparation of 4,5-diamino shikimic acid derivatives - Google Patents

Process for the preparation of 4,5-diamino shikimic acid derivatives Download PDF

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Publication number
CA2337452C
CA2337452C CA002337452A CA2337452A CA2337452C CA 2337452 C CA2337452 C CA 2337452C CA 002337452 A CA002337452 A CA 002337452A CA 2337452 A CA2337452 A CA 2337452A CA 2337452 C CA2337452 C CA 2337452C
Authority
CA
Canada
Prior art keywords
formula
compound
azide
acid
phosphoryl
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
CA002337452A
Other languages
English (en)
French (fr)
Other versions
CA2337452A1 (en
Inventor
Stefan Abrecht
Martin Karpf
Rene Trussardi
Beat Wirz
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of CA2337452A1 publication Critical patent/CA2337452A1/en
Application granted granted Critical
Publication of CA2337452C publication Critical patent/CA2337452C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
    • C07C211/40—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing only non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • 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
    • C07C229/48—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 of the same non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/26—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Catalysts (AREA)
CA002337452A 2000-02-22 2001-02-16 Process for the preparation of 4,5-diamino shikimic acid derivatives Expired - Lifetime CA2337452C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP00103673.0 2000-02-22
EP00103673 2000-02-22

Publications (2)

Publication Number Publication Date
CA2337452A1 CA2337452A1 (en) 2001-08-22
CA2337452C true CA2337452C (en) 2008-04-15

Family

ID=8167922

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002337452A Expired - Lifetime CA2337452C (en) 2000-02-22 2001-02-16 Process for the preparation of 4,5-diamino shikimic acid derivatives

Country Status (13)

Country Link
US (1) US6403824B2 (Direct)
EP (1) EP1127872B1 (Direct)
JP (1) JP4954378B2 (Direct)
KR (1) KR100743305B1 (Direct)
CN (1) CN1280258C (Direct)
AT (1) ATE316952T1 (Direct)
CA (1) CA2337452C (Direct)
DE (1) DE60116909T2 (Direct)
DK (1) DK1127872T3 (Direct)
ES (1) ES2256096T3 (Direct)
IN (1) IN192890B (Direct)
JO (1) JO2251B1 (Direct)
PT (1) PT1127872E (Direct)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6518048B2 (en) * 2000-04-10 2003-02-11 Hoffmann-La Roche Inc. Stereo-specific synthesis of shimikic acid derivatives with improved efficiency
US7122684B2 (en) 2003-03-13 2006-10-17 Roche Colorado Corporation Process for preparing 1,2-diamino compounds
EP1602730A3 (en) * 2004-06-04 2006-01-25 DSM IP Assets B.V. Biosynthetic production of 4-amino-4-deoxychorismate (ADC) and [3R,4R]-4-amino-3-hydroxycyclohexa-1,5-diene-1-carboxylic acid (3,4-CHA)
MX2007002316A (es) * 2004-09-02 2007-04-17 Hoffmann La Roche Proceso para preparacion de acido 4,5-diamino shikimico.
US7977077B2 (en) 2006-01-30 2011-07-12 Board Of Trustees Of Michigan State University Synthesis of intermediates of oseltamivir carboxylates
US20080009639A1 (en) * 2006-07-10 2008-01-10 Apotex Pharmachem Inc. Preparation of oseltamivir phosphate (Tamiflu) and intermediates starting from D-glucose or D-xylose
WO2008077809A1 (en) * 2006-12-22 2008-07-03 F. Hoffmann-La Roche Ag Process for the manufacture of 7-oxa-bicyclo derivatives
CN101801914B (zh) * 2007-09-18 2013-06-05 弗·哈夫曼-拉罗切有限公司 从莽草酸生成磷酸奥司他韦的方法
KR101049475B1 (ko) * 2008-12-22 2011-07-15 (주)팜스웰바이오 아자-바이사이클로[2.2.1]헵텐 유도체, 이의 제조방법 및 이를 이용한 오셀타미비르의 중간체의 제조방법
JP5796762B2 (ja) * 2010-10-18 2015-10-21 国立大学法人豊橋技術科学大学 光学活性なシクロヘキセン誘導体の製造方法
CN102464596A (zh) * 2010-11-10 2012-05-23 南开大学 “一锅法”获得达菲合成反应的关键中间体
US9834796B2 (en) 2011-09-07 2017-12-05 Shinshu University Method for producing useful metabolite from filamentous fungus
CN105801445B (zh) * 2016-04-13 2017-08-25 福建师范大学 一种具有抗菌活性的非蛋白质氨基酸及其制备方法
US10385010B1 (en) * 2018-03-28 2019-08-20 Georgia State University Research Foundation, Inc. Expedient synthesis of oseltamivir and related compounds via direct olefin diazidation-diamidation reaction

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998007685A1 (en) 1996-08-23 1998-02-26 Gilead Sciences, Inc. Preparation of cyclohexene carboxylate derivatives
EP1015417A1 (en) 1997-09-17 2000-07-05 Gilead Sciences, Inc. Compounds containing six-membered rings, processes for their preparation, and their use as medicaments
AU7608100A (en) 1999-10-19 2001-04-30 Abbott Laboratories 1-cyclohexene-1-carboxylic acid and 1-cyclohexene-1-carboxylates as neuraminidase inhibitors

Also Published As

Publication number Publication date
EP1127872A1 (en) 2001-08-29
US20020006960A1 (en) 2002-01-17
ES2256096T3 (es) 2006-07-16
KR20010083189A (ko) 2001-08-31
CN1310170A (zh) 2001-08-29
JP2001288152A (ja) 2001-10-16
ATE316952T1 (de) 2006-02-15
DE60116909D1 (de) 2006-04-13
IN192890B (Direct) 2004-05-29
JO2251B1 (en) 2004-10-07
DE60116909T2 (de) 2006-09-28
PT1127872E (pt) 2006-06-30
KR100743305B1 (ko) 2007-07-26
CA2337452A1 (en) 2001-08-22
DK1127872T3 (da) 2006-06-12
US6403824B2 (en) 2002-06-11
CN1280258C (zh) 2006-10-18
JP4954378B2 (ja) 2012-06-13
EP1127872B1 (en) 2006-02-01

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Effective date: 20210216