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WO1990015810A3 - Procede ameliore de preparation d'isepamicine - Google Patents

Procede ameliore de preparation d'isepamicine Download PDF

Info

Publication number
WO1990015810A3
WO1990015810A3 PCT/US1990/003328 US9003328W WO9015810A3 WO 1990015810 A3 WO1990015810 A3 WO 1990015810A3 US 9003328 W US9003328 W US 9003328W WO 9015810 A3 WO9015810 A3 WO 9015810A3
Authority
WO
WIPO (PCT)
Prior art keywords
isoserine
improved process
isepamicin
preparing
compounds
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.)
Ceased
Application number
PCT/US1990/003328
Other languages
English (en)
Other versions
WO1990015810A2 (fr
Inventor
Chou-Hong Tann
Tiruvettipuram K Thiruvengadam
John Sze-Hung Chiu
Cesar Colon
Michael D Green
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.)
Merck Sharp and Dohme LLC
Original Assignee
Schering Corp
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 Schering Corp filed Critical Schering Corp
Priority to KR1019910700196A priority Critical patent/KR940003496B1/ko
Priority to CA002062788A priority patent/CA2062788C/fr
Priority to JP2509550A priority patent/JPH0692433B2/ja
Publication of WO1990015810A2 publication Critical patent/WO1990015810A2/fr
Publication of WO1990015810A3 publication Critical patent/WO1990015810A3/fr
Priority to FI915953A priority patent/FI96955C/fi
Priority to NO915071A priority patent/NO177349C/no
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
    • C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
    • C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
    • C07H15/236—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • 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)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Selon un procédé amélioré de conversion de gentamicine B en isépamicine, on prépare 3,6'-di-N-formylgentamicine B, on acyle le groupe 1-amine avec un composé de (S)-isosérine à N protégé et on élimine tous les groupes de blocage dans des conditions qui permettent d'obtenir des quantités élevées d'isépamicine. L'invention concerne également un nouvel agent formylant, le 2-formylmercaptobenzothiazole, et des composés intermédiaires.
PCT/US1990/003328 1989-06-21 1990-06-19 Procede ameliore de preparation d'isepamicine Ceased WO1990015810A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1019910700196A KR940003496B1 (ko) 1989-06-21 1990-06-19 이세파마이신의 개선된 제조방법
CA002062788A CA2062788C (fr) 1989-06-21 1990-06-19 Procede d'obtention d'isepamicine
JP2509550A JPH0692433B2 (ja) 1989-06-21 1990-06-19 イセパミシンを調製するための改良法
FI915953A FI96955C (fi) 1989-06-21 1991-12-18 Parannettu isepamisiinin valmistusmenetelmä
NO915071A NO177349C (no) 1989-06-21 1991-12-20 Fremgangsmåte for fremstilling av isepamicin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US36957889A 1989-06-21 1989-06-21
US369,578 1989-06-21

Publications (2)

Publication Number Publication Date
WO1990015810A2 WO1990015810A2 (fr) 1990-12-27
WO1990015810A3 true WO1990015810A3 (fr) 1991-04-04

Family

ID=23456036

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/003328 Ceased WO1990015810A2 (fr) 1989-06-21 1990-06-19 Procede ameliore de preparation d'isepamicine

Country Status (16)

Country Link
EP (3) EP0405820B1 (fr)
JP (2) JPH0692433B2 (fr)
KR (1) KR940003496B1 (fr)
AT (2) ATE152094T1 (fr)
AU (1) AU629960B2 (fr)
CA (2) CA2325082A1 (fr)
DE (2) DE69008052T2 (fr)
DK (2) DK0547031T3 (fr)
ES (2) ES2063274T3 (fr)
FI (1) FI96955C (fr)
GR (1) GR3023942T3 (fr)
HK (2) HK185096A (fr)
HU (1) HU207338B (fr)
NO (1) NO177349C (fr)
RU (1) RU2120444C1 (fr)
WO (1) WO1990015810A2 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100927626B1 (ko) * 2002-09-18 2009-11-20 쯔지앙 하이썬 파머슈티컬 컴퍼니, 리미티드 이세파마이신의 제조 방법
CN101928310B (zh) * 2010-03-26 2012-09-05 常州方圆制药有限公司 3,2’,6’-三-N-乙酰基庆大霉素C1a的制备方法
CN102190690B (zh) * 2011-04-01 2015-01-21 福州博立医药科技有限公司 一种简便且高收率阿贝卡星合成方法
CN105524129B (zh) * 2015-12-25 2018-06-26 无锡济民可信山禾药业股份有限公司 一种硫酸依替米星的制备方法
RU2659032C1 (ru) * 2017-04-26 2018-06-27 Федеральное государственное бюджетное образовательное учреждение высшего образования "Удмуртский государственный университет" Способ модификации гентамицина сополимером винилпирролидона с диацеталем акролеина
CN108586313B (zh) * 2018-03-31 2019-12-27 海正药业南通有限公司 一种新型合成n-取代苯酐-(s)-异丝氨酸的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2726712A1 (de) * 1976-06-17 1977-12-22 Scherico Ltd Verfahren zur selektiven blockierung von aminogruppen
FR2441631A1 (fr) * 1978-11-11 1980-06-13 Microbial Chem Res Found Procede de preparation d'un derive n-acyle selectivement protege d'un antibiotique aminoglycosidique
EP0156771A2 (fr) * 1984-03-29 1985-10-02 Biochemie Gesellschaft M.B.H. Céphalosporines

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4230847A (en) * 1976-06-17 1980-10-28 Schering Corporation Aminoglycoside antibiotic compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2726712A1 (de) * 1976-06-17 1977-12-22 Scherico Ltd Verfahren zur selektiven blockierung von aminogruppen
FR2441631A1 (fr) * 1978-11-11 1980-06-13 Microbial Chem Res Found Procede de preparation d'un derive n-acyle selectivement protege d'un antibiotique aminoglycosidique
EP0156771A2 (fr) * 1984-03-29 1985-10-02 Biochemie Gesellschaft M.B.H. Céphalosporines

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J.P. GREENSTEIN and M. WINITZ, Chemistry of the Amino Acids, Vol. 2, John Wiley & Sons, Inc., (New York, US), pages 920-921 see part 20, Formyl Group *
T.W. GREENE, Protective Groups in Organic Synthesis, John Wiley, (New York, US), page 52 see part 1, Formate Ester *

Also Published As

Publication number Publication date
ES2063274T3 (es) 1995-01-01
EP0405820A3 (en) 1991-04-10
AU5946390A (en) 1991-01-08
JPH07133267A (ja) 1995-05-23
DK0405820T3 (da) 1994-05-16
EP0547031A1 (fr) 1993-06-16
JPH0692433B2 (ja) 1994-11-16
DE69030590T2 (de) 1997-08-07
CA2325082A1 (fr) 1990-12-22
HU906641D0 (en) 1992-03-30
JP2500059B2 (ja) 1996-05-29
EP0405820A2 (fr) 1991-01-02
DK0547031T3 (da) 1997-05-20
EP0547031B1 (fr) 1997-04-23
KR920701226A (ko) 1992-08-11
HU207338B (en) 1993-03-29
CA2062788A1 (fr) 1990-12-22
CA2062788C (fr) 2001-10-23
FI915953A0 (fi) 1991-12-18
ES2100380T3 (es) 1997-06-16
FI96955B (fi) 1996-06-14
HK185096A (en) 1996-10-11
ATE104310T1 (de) 1994-04-15
FI96955C (fi) 1996-09-25
NO915071D0 (no) 1991-12-20
JPH04502474A (ja) 1992-05-07
DE69008052D1 (de) 1994-05-19
NO177349C (no) 1995-08-30
NO177349B (no) 1995-05-22
GR3023942T3 (en) 1997-09-30
AU629960B2 (en) 1992-10-15
HK1000153A1 (en) 1998-01-02
RU2120444C1 (ru) 1998-10-20
EP0478707A1 (fr) 1992-04-08
NO915071L (no) 1991-12-20
DE69008052T2 (de) 1994-07-28
DE69030590D1 (de) 1997-05-28
WO1990015810A2 (fr) 1990-12-27
EP0405820B1 (fr) 1994-04-13
KR940003496B1 (ko) 1994-04-23
ATE152094T1 (de) 1997-05-15
HUT59934A (en) 1992-07-28

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