KR970707135A - 실릴화 방법(Silylation process) - Google Patents

실릴화 방법(Silylation process)

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Publication number
KR970707135A
KR970707135A KR1019970703336A KR19970703336A KR970707135A KR 970707135 A KR970707135 A KR 970707135A KR 1019970703336 A KR1019970703336 A KR 1019970703336A KR 19970703336 A KR19970703336 A KR 19970703336A KR 970707135 A KR970707135 A KR 970707135A
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KR
South Korea
Prior art keywords
acid
alkyl
desacetoxy
silylated
amino
Prior art date
Application number
KR1019970703336A
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English (en)
Other versions
KR100416673B1 (ko
Inventor
빅터 센텔라스
호세 디아고
요안네스 루데셔
Original Assignee
샬러 한스, 하우스 한스 루돌프
비오케미 게젤샤프트 엠. 베. 하.
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Application filed by 샬러 한스, 하우스 한스 루돌프, 비오케미 게젤샤프트 엠. 베. 하. filed Critical 샬러 한스, 하우스 한스 루돌프
Publication of KR970707135A publication Critical patent/KR970707135A/ko
Application granted granted Critical
Publication of KR100416673B1 publication Critical patent/KR100416673B1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cephalosporin Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Silicates, Zeolites, And Molecular Sieves (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Vibration Prevention Devices (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 특정한 카복실산 에스테르에서 실릴화에 의한 6-아미노페니실란산 또는 7-아미노-데스아세톡시-세팔로스포란산의 실릴화 방법 및 6-α-아미노아실-페니실린 및 7-α-아미노아실-데스아세톡시-세팔로스포린의 제조에 있어서의 이의 용도에 관한 것이다.

Description

실릴화 방법(Silylation process)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (11)

  1. 하기 화학식 (Ⅰ)의 카복실산 에스테르에서 7-아미노-데스아세톡시-세팔로스포란산을 실릴화함으로써 실릴화된 7-아미노-데스아세톡시-세팔로스포란산을 제조하는 방법.
    X-COO-Y (Ⅰ)
    상기 화학식에서 서로 독립적으로, X는 메틸이고, Y는 탄소수 3 이상의 알킬이거나, X는 탄소수 2 이상의 알킬이고, Y는 알킬이다.
  2. N, N-비스트리메틸실릴 아세트아미드, N, N'-비스트리메틸실릴말론아미드 및 N, N'-비스트리메틸실릴 우레아 이외의 실릴화제의 존재하에 하기 화학식 (Ⅰ)의 카복실산 에스테르에서 6-아미노페니실란산을 실릴화함으로써 실릴화된 6-아미노페니실란산을 제조하는 방법.
    X-COO-Y (Ⅰ)
    상기 화학식에서 서로 독립적으로, X는 메틸이고, Y는 탄소수 3 이상의 알킬이거나, X는 탄소수 2 이상의 알킬이고, Y는 알킬이다.
  3. 제1항 또는 제2항에 있어서, 서로 독립적으로, X가 메틸이고 Y가 (C3-8)알킬 또는 (C5-6)사이클로알킬 알킬이거나, X가 탄소수 2 이상의 알킬이고 Y가 (C1-8)알킬 또는 (C5-6)사이클로알킬인 화학식 (Ⅰ)의 카복실산 에스테르를 사용함을 포함하는 방법.
  4. 제1항 또는 제3항 중의 어느 한 항에 있어서, X가 메틸이고, Y가 (C3-8)알킬인 화학식 (Ⅰ)의 카복실산 에스테르를 사용함을 포함하는 방법.
  5. 제1항 내지 제4항 중의 어느 한 항에 있어서, 카복실산 에스테르가 프로필아세테이트 또는 부틸 아세테이트인 방법.
  6. 이소-프로필아세테이트 또는 n-부틸 아세테이트에서 7-아미노-데스아세톡시-세팔로스포란산 또는 6-아미노페니실란산을 실릴화함으로써 실릴화된 7-아미노-데스아세톡시-세팔로스포린산 또는 6-아미노페니실란산을 제조하는 방법.
  7. (i) 하기 화학식 (Ⅰ)의 카복실산 에스테르에서 7-아미노-데스아세톡시-세팔로스포란산 또는 6-아미노페니실란산을 실릴화함으로써 실릴화된 7-아미노-데스아세톡시-세팔로스포란산 또는 실릴화된 6-아미노페니실란산을 생성시키고, (ii) 실릴화된 7-아미노-데스아세톡시-세팔로스포란산 또는 실릴화된 6-아미노페니실란산을 적당한 아실화제로 아실화함을 포함하여, 아목시실린을 제외한 7-아미노아실-데스아세톡시-세팔로스포린 또는 6-아미노아실-페니실린을 제조하는 방법.
    X-COO-Y (Ⅰ)
    상기 화학식에서 X는 메틸이고, Y는 탄소수 3 이상의 알킬이거나, X는 탄소수 2 이상의 알킬이고, Y는 알킬이다.
  8. (i) N, N-비스트리메틸실릴 아세트아미드, N, N'-비스트리메틸실릴말론산 아미드 및 N, N'-비스트리메틸실릴 우레아 이외의 실릴화제의 존재하에, 하기 화학식 (Ⅰ)의 카복실산 에스테르에서 7-아미노-데스아세톡시-세팔로스포란산 또는 6-아미노페니실란산을 실릴화함으로써 실릴화된 7-아미노-데스아세톡시-세팔로스포란산 또는 실릴화된 6-아미노페니실란산을 생성시키고, (ii) 실릴화된 7-아미노-데스아세톡시-세팔로스포란산 또는 실릴화된 6-아미노페니실란산을 적당한 아실화제와 혼합 카복실산 무수물로 아실화하는 단계를 포함하여, 아목시실린을 제조하는 방법.
    X-COO-Y (Ⅰ)
    상기 화학식에서 X는 메틸이고, Y는 탄소수 3 이상의 알킬이거나, X가 탄소수 2 이상의 알킬이고, Y는 알킬이다.
  9. (i) 하기 화학식 (Ⅰ)의 카복실산 에스테르에서 7-아미노-데스아세톡시-세팔로스포란산 또는 6-아미노페니실란산을 실릴화함으로써 실릴화된 7-아미노-데스아세톡시-세팔로스포란산 또는 실릴화된 6-아미노페니실란산을 생성시키고, (ii) 실릴화된 7-아미노-데스아세톡시-세팔로스포란산 또는 실릴화된 6-아미노페니실란산을 N-엔아민으로 보호되는 아민 그룹을 갖는 α-아미노산 염과 클로르카본산 에스테르 이외의 적당한 아실화제와의 반응으로 생성되는 혼합 카복실산 무수물로 아실화하는 단계를 포함하여, 아목시실린을 제조하는 방법.
    X-COO-Y (Ⅰ)
    상기 화학식에서 X는 메틸이고, Y는 탄소수 3 이상의 알킬이거나, X가 탄소수 2 이상의 알킬이고, Y는 알킬이다.
  10. 7-α-아미노아실-데스아세톡시-세팔로스포린의 제조 방법에 있어서의 제1항에 따른 방법의 용도.
  11. 6-α-아미노아실페니실린의 제조 방법에 있어서의 제2항에 따른 방법의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019970703336A 1994-11-21 1995-11-20 실릴화방법 KR100416673B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9423459A GB9423459D0 (en) 1994-11-21 1994-11-21 Silylation process
GB9423459.8 1994-11-21

Publications (2)

Publication Number Publication Date
KR970707135A true KR970707135A (ko) 1997-12-01
KR100416673B1 KR100416673B1 (ko) 2004-03-18

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ID=10764738

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Application Number Title Priority Date Filing Date
KR1019970703336A KR100416673B1 (ko) 1994-11-21 1995-11-20 실릴화방법

Country Status (16)

Country Link
US (1) US5998610A (ko)
EP (1) EP0793666B1 (ko)
JP (2) JP3072857B2 (ko)
KR (1) KR100416673B1 (ko)
CN (2) CN1062272C (ko)
AT (1) ATE216702T1 (ko)
AU (1) AU4174496A (ko)
DE (1) DE69526519T2 (ko)
ES (1) ES2176349T3 (ko)
GB (1) GB9423459D0 (ko)
HU (1) HUT77102A (ko)
PL (1) PL184270B1 (ko)
PT (1) PT793666E (ko)
SI (1) SI0793666T1 (ko)
TW (1) TW432070B (ko)
WO (1) WO1996016067A1 (ko)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1447406B1 (en) * 1999-09-30 2006-08-09 Otsuka Kagaku Kabushiki Kaisha 3-Cephem derivative crystal
US20040077849A1 (en) * 2002-10-16 2004-04-22 Orchid Chemicals & Pharmaceuticals Limited Process for the preparation of cefadroxil
US20060172987A1 (en) * 2003-03-21 2006-08-03 Dsm Ip Assets B.V. Amoxicillin trihydrate
US7534781B2 (en) * 2003-03-21 2009-05-19 Dsm Ip Assets B.V. Crystalline amoxicillin trihydrate powder
ES2359600T3 (es) * 2007-07-30 2011-05-25 Dsm Ip Assets B.V. Proceso para sililar beta-lactamas.
CN101845053B (zh) * 2010-03-09 2012-07-25 河北科技大学 一种分离提纯阿莫西林三水化合物的方法
CN103183685B (zh) * 2011-12-30 2016-03-30 浙江新和成股份有限公司 6α-酰胺基青霉烷酸亚砜化合物的制备方法

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE311519B (ko) * 1962-12-14 1969-06-16 Astra Ab
US4093803A (en) * 1971-05-14 1978-06-06 Glaxo Laboratories Limited 7β-[2-Etherified oximino-2-(thienyl-, furyl- or pyridylacetamido)] cephalosporins
US4138555A (en) * 1971-05-14 1979-02-06 Glaxo Laboratories, Limited (6R,7R)-7-[2-aryl-2-(etherified oximino)acetamido]-3-carbamoyloxymethylceph-3-em-4-carboxylic acid 1-oxides
DK154939C (da) * 1974-12-19 1989-06-12 Takeda Chemical Industries Ltd Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf
GB1459807A (en) * 1975-05-27 1976-12-31 Proter Spa Process for the production of 7-d-a-amino-phenyl-acetamido-3- desacetoxy-cephalosporanic acid
US4196205A (en) * 1976-01-23 1980-04-01 Roussel Uclaf 3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives
US5336776A (en) * 1976-01-23 1994-08-09 Roussel Uclaf 3-acetoxymethyl-7-(iminoacetamideo)-cephalosporanic acid
US5079369A (en) * 1976-04-12 1992-01-07 Fujisawa Pharmaceutical Company, Ltd. Syn-isomer of 3,7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof
GR63088B (en) * 1976-04-14 1979-08-09 Takeda Chemical Industries Ltd Preparation process of novel cephalosporins
GB1532682A (en) * 1976-04-27 1978-11-22 Bristol Myers Co Process for the preparation of cephadroxil
DE2714880A1 (de) * 1977-04-02 1978-10-26 Hoechst Ag Cephemderivate und verfahren zu ihrer herstellung
GB2001985B (en) * 1977-08-05 1982-07-07 Lark Spa Process for the preparation of penicillanic and cephalosporanic acid derivatives
FR2400519A1 (fr) * 1977-08-17 1979-03-16 Roussel Uclaf Forme cristalline du sel de sodium d'un derive oximine de l'acide 7-amino-thiazolyl acetamido cephalosporanique, son procede de preparation et son application comme medicament
NL162387C (nl) * 1977-09-06 1980-05-16 Gist Brocades Nv Werkwijze voor het bereiden van 6-(d-alpha-amino-p- -hydroxyfenylacetamido)penicillanzuur.
JPS5459296A (en) * 1977-10-14 1979-05-12 Toshin Chemical Co Production of alphaaaminoo paraahydroxybenzylpeniciline
CA1125745A (en) * 1978-11-20 1982-06-15 Joseph Kaspi PROCESS FOR PREPARING .beta.-LACTAM ANTIBIOTICS
IT1126544B (it) * 1979-12-07 1986-05-21 Dobfar Spa Procedimento per la preparazione di derivati dell'acido 7-amino-desacetossi cefalosporanico
EP0037380B1 (en) * 1980-03-28 1984-09-12 BIOCHEMIE Gesellschaft m.b.H. New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production
IT1180207B (it) * 1984-07-30 1987-09-23 Istituto Biochimico Italiano Procedimento per la preparazione, con resa e purezza elevate, di antibiotici beta-lattamici
DE3539901A1 (de) * 1985-11-11 1987-05-14 Hoechst Ag Cephalosporinderivate und verfahren zu ihrer herstellung
IT1214587B (it) * 1986-12-23 1990-01-18 Giovanni Bonfanti Metodo per la produzione diprodotti cristallini puri.
ES2006988A6 (es) * 1988-06-20 1989-05-16 Gema Sa Procedimiento de preparar hidrocloruro cloruro-2-(2-aminotiazol-4-il)-2-metoxiiminoacetil-sulfito-dimetilformiminio y procedimiento de utilizacion del mismo para obtencion de amidas.
US5034522A (en) * 1988-08-02 1991-07-23 Biocraft Laboratories, Inc. Method for the production of 3-methyl cephem derivatives
GB2240102B (en) * 1990-01-22 1993-10-20 Biochemie Gmbh Improvements in or relating to beta lactam production
CA2033692A1 (en) * 1990-01-25 1991-07-26 Wilhelm Bannwarth Energy transfer systems
US5142043A (en) * 1990-05-10 1992-08-25 Biocraft Laboratories, Inc. Process for preparing cephalexin monohydrate
US5574154A (en) * 1994-09-29 1996-11-12 Alnejma Bulk Pharmaceutical Co. A.B.P.C. Process for the preparation of cephalosporanic compounds

Also Published As

Publication number Publication date
CN1124277C (zh) 2003-10-15
PT793666E (pt) 2002-09-30
ES2176349T3 (es) 2002-12-01
US5998610A (en) 1999-12-07
CN1164235A (zh) 1997-11-05
DE69526519D1 (de) 2002-05-29
WO1996016067A1 (en) 1996-05-30
SI0793666T1 (en) 2002-10-31
AU4174496A (en) 1996-06-17
JP2000229986A (ja) 2000-08-22
KR100416673B1 (ko) 2004-03-18
EP0793666B1 (en) 2002-04-24
PL319752A1 (en) 1997-08-18
GB9423459D0 (en) 1995-01-11
CN1280982A (zh) 2001-01-24
EP0793666A1 (en) 1997-09-10
DE69526519T2 (de) 2002-10-31
JPH10507773A (ja) 1998-07-28
PL184270B1 (pl) 2002-09-30
ATE216702T1 (de) 2002-05-15
HUT77102A (hu) 1998-03-02
CN1062272C (zh) 2001-02-21
TW432070B (en) 2001-05-01
JP3072857B2 (ja) 2000-08-07

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