KR860008189A - 7-amino-3-propenyl cephalosporan acid and its esters - Google Patents

7-amino-3-propenyl cephalosporan acid and its esters Download PDF

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Publication number
KR860008189A
KR860008189A KR1019860003085A KR860003085A KR860008189A KR 860008189 A KR860008189 A KR 860008189A KR 1019860003085 A KR1019860003085 A KR 1019860003085A KR 860003085 A KR860003085 A KR 860003085A KR 860008189 A KR860008189 A KR 860008189A
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KR
South Korea
Prior art keywords
compound
group
salt
lithium
amino
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KR1019860003085A
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Korean (ko)
Inventor
호시 히데끼
오쿠무라 준
아베 요시오
나이또 다까유끼
아부라끼 심페리
Original Assignee
이삭 쟈코브스키
브리스톨 마이어즈 컴파니
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.)
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Application filed by 이삭 쟈코브스키, 브리스톨 마이어즈 컴파니 filed Critical 이삭 쟈코브스키
Publication of KR860008189A publication Critical patent/KR860008189A/en
Priority to KR1019900002094A priority Critical patent/KR900004930B1/en

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Classifications

    • 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
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
    • 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
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
    • 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

Abstract

내용 없음No content

Description

7-아미노-3-프로페닐 세팔로스포란산 및 그 에스텔7-amino-3-propenyl cephalosporan acid and its esters

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (11)

일반식의 화합물 및 이것의 산부가염과With compounds of the general formula and acid addition salts thereof R이 수소인 상기 물질의 금속염.A metal salt of said material wherein R is hydrogen. 이식에서, 3-프로페닐그룹은 Z-배열이고 R은 수소이거나 통상적인 카복시-보호그룹이다.In transplantation, the 3-propenyl group is Z-configuration and R is hydrogen or a conventional carboxy-protective group. R이 수소, 메톡시메틸, 2,2,2-트리클로로에틸, 2-(트리메틸실릴)에틸, t-부틸, 벤질, 디페닐메틸, o-니트로벤질, p-니트로벤질, 트리메틸실릴, t-부틸디메틸-실릴, t-부틸디페닐실릴, 알릴 및 2-클로로알릴로부터 선택된 그룹인 청구범위 1항의 화합물 및 그 산부가염.R is hydrogen, methoxymethyl, 2,2,2-trichloroethyl, 2- (trimethylsilyl) ethyl, t-butyl, benzyl, diphenylmethyl, o-nitrobenzyl, p-nitrobenzyl, trimethylsilyl, t The compound of claim 1 and an acid addition salt thereof, wherein the compound is a group selected from -butyldimethyl-silyl, t-butyldiphenylsilyl, allyl and 2-chloroallyl. 산부가염이 염산염, 황산염, p-톨루엔슬페이트, 및 인산염으로 구성되는 그룹에서 선택되는 청구범위 제2항의 화합물.The compound of claim 2 wherein the acid addition salt is selected from the group consisting of hydrochloride, sulfate, p-toluenesulfate, and phosphate. 금속염이 나트륨, 칼륨, 칼슘 또는 알루미늄염인 청구범위 제1항의 화합물.The compound of claim 1 wherein the metal salt is a sodium, potassium, calcium or aluminum salt. 디페닐메틸 7β-아미노-3-[(Z)-1-프로펜-1-일]-3-세펨-4-카복실산염인 청구범위 제2항의 화합물 및 그 염산염.The compound of claim 2 and the hydrochloride salt thereof, which is diphenylmethyl 7β-amino-3-[(Z) -1-propen-1-yl] -3-cefe-4-carboxylic acid salt. 7β-아미노-3-[(Z)-1-프로펜-1-일]-3-세펨-4-카복실산인 청구범위 제2항의 화합물 및 그 염산염.The compound of claim 2 and a hydrochloride thereof, which is 7β-amino-3-[(Z) -1-propen-1-yl] -3-cepem-4-carboxylic acid. 소듐 7β-아미노-3-[(Z)-1-프로펜-1-일]-3-세펨-4-카복실산염인 청구범위 제4항의 화합물.The compound of claim 4 which is sodium 7β-amino-3-[(Z) -1-propen-1-yl] -3-cefe-4-carboxylic acid salt. R이 청구범위 제1항에서와 같은 의미를 가지며 ph가 페닐그룹인 다음 일반식의 중간체를,An intermediate of formula (I) wherein R has the same meaning as in claim 1 and ph is a phenyl group, 디클로로메탄, N,N'-디메틸포름아미드, 이소프로파놀 또는 그 혼합물로 이루어지는 불활성 유기반응 매질에서 0℃와 25℃사이의 반응온도로 아세트알데히드와 반응시켜서 다음 일반식의 화합물을 얻은 후,In an inert organic reaction medium consisting of dichloromethane, N, N'-dimethylformamide, isopropanol or mixtures thereof, the mixture is reacted with acetaldehyde at a reaction temperature between 0 ° C and 25 ° C to obtain a compound of the general formula 벤질리덴그룹이나 벤질리덴그룹와 카복시-보호그룹 둘다를 제거하는 것으로 이루어지며, 필요하면, 3-(Z) 및 3-(E) 이성체를 분리시켜서 R이 청구범위 제1항에서와 동일한 의미를 갖는 다음 일반식의 화합물을 얻는 것으로 이루어지는Consisting of removing both the benzylidene group or the benzylidene group and the carboxy-protecting group, if necessary, separating the 3- (Z) and 3- (E) isomers so that R has the same meaning as in claim 1 Which consists of obtaining the compound of the following general formula 청구범위 제1항에서 청구된 바와 같은 화합물을 제조하는 방법.A process for preparing a compound as claimed in claim 1. 아세트알데히드와의 반응이 할로겐화 리튬의 존재하에 진행되는 청구범위 제8항의 방법.The method of claim 8 wherein the reaction with acetaldehyde proceeds in the presence of lithium halide. 할로겐화리튬이 염화리튬, 취화리튬, 또는 요오드화리튬 청구범위 제9항의 방법.The method of claim 9 wherein lithium halide is lithium chloride, lithium embrittlement, or lithium iodide. 할로겐화리튬이 취화리튬인 청구범위 제9항의 방법.The method of claim 9 wherein the lithium halide is lithium embrittlement. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019860003085A 1985-04-22 1986-04-22 7-amino-3-propenyl cephalosporan acid and its esters KR860008189A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019900002094A KR900004930B1 (en) 1985-04-22 1990-02-21 Process for preparing 7-amino -3-prophenyl cephalosporins

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US72587185A 1985-04-22 1985-04-22
US725,871 1985-04-22

Related Child Applications (1)

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KR1019900002094A Division KR900004930B1 (en) 1985-04-22 1990-02-21 Process for preparing 7-amino -3-prophenyl cephalosporins

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KR860008189A true KR860008189A (en) 1986-11-12

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JP (1) JPS61249989A (en)
KR (1) KR860008189A (en)
CN (1) CN1015714B (en)
AR (1) AR242581A1 (en)
AT (1) AT392072B (en)
AU (1) AU589170B2 (en)
BE (1) BE904646A (en)
CA (1) CA1273629A (en)
CH (1) CH671399A5 (en)
CS (1) CS270435B2 (en)
CY (1) CY1571A (en)
DD (1) DD244557A5 (en)
DE (1) DE3613365A1 (en)
DK (1) DK163584C (en)
EG (1) EG18001A (en)
ES (1) ES8800236A1 (en)
FI (1) FI84268C (en)
FR (1) FR2580652B1 (en)
GB (1) GB2173798B (en)
GR (1) GR861065B (en)
HK (1) HK106290A (en)
HU (1) HU195223B (en)
IE (1) IE59014B1 (en)
IT (1) IT1228241B (en)
LU (1) LU86402A1 (en)
MY (1) MY100694A (en)
NL (1) NL192205C (en)
NO (1) NO164659C (en)
NZ (1) NZ215717A (en)
OA (1) OA08245A (en)
PT (1) PT82436B (en)
SE (1) SE500217C2 (en)
SG (1) SG90890G (en)
SU (1) SU1435155A3 (en)
YU (1) YU43697B (en)
ZA (1) ZA862985B (en)
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Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4708955A (en) * 1985-06-24 1987-11-24 Bristol-Myers Company 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof
US4870168A (en) * 1987-02-26 1989-09-26 Bristol-Myers Company 3-Unsaturated alkyl cephems from 3-triflyl cephems
DE3933934A1 (en) * 1989-10-03 1991-04-11 Bayer Ag METHOD FOR PRODUCING 7-AMINO-3 - ((Z) -1-PROPEN-1-YL) -3-CEPHEM-4-CARBONIC ACID
PT503453E (en) * 1991-03-08 2001-10-31 Biochemie Gmbh NEW PROCESS FOR THE PRODUCTION OF CEFALOSPORINAS AND NEW INTERMEDIARIES IN THIS PROCESS
ATE253583T1 (en) 1992-02-05 2003-11-15 Biochemie Gmbh METHOD FOR PRODUCING A 3-CEPHEM-4-CARBOXYLIC ACID DERIVATIVE
AT399876B (en) * 1992-02-05 1995-08-25 Biochemie Gmbh Purificn. of 7-amino-3-((z)-1-propen-1-yl)-3 -cephem-4-carboxylic acid - useful in prodn. of broadband antibiotics
JPH07173168A (en) * 1993-07-14 1995-07-11 Sumitomo Chem Co Ltd Cephem compound, its production and utilization of the compound for production of cephem antibiotic substance
AU2003267733A1 (en) * 2002-10-08 2004-05-04 Ranbaxy Laboratories Limited Process for the preparation of (z)-isomer enriched 7-amino-3-propen-1-yl-3-cephem-4- carboxylic acid
WO2005042543A1 (en) 2003-10-30 2005-05-12 Cj Corporation Processes for the preparation of cephem derivatives
JP4046708B2 (en) * 2004-06-04 2008-02-13 明治製菓株式会社 Method for producing 3-alkenylcephem compound
DE602004025631D1 (en) * 2004-11-01 2010-04-01 Hetero Drugs Ltd ISCHENPRODUKTS
CN103183686B (en) * 2011-12-30 2016-06-29 浙江新和成股份有限公司 The preparation method of 7 beta-amino-7 α-methoxyl group-3-cephem compounds

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US3769277A (en) * 1970-01-23 1973-10-30 Glaxo Lab Ltd Preparation of delta3-4 carboxy cephalosporins having a 3-vinyl or substituted 3-vinyl group
GB1342241A (en) * 1970-01-23 1974-01-03 Glaxo Lab Ltd Cephalosporin compounds
US4110534A (en) * 1970-01-23 1978-08-29 Glaxo Laboratories Limited Process for the preparation of 3-vinyl and substituted vinyl cephalosporins
US4065620A (en) * 1971-06-14 1977-12-27 Eli Lilly And Company 3-(Substituted) vinyl cephalosporins
US4409214A (en) * 1979-11-19 1983-10-11 Fujisawa Pharmaceutical, Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof
US4520022A (en) * 1983-01-28 1985-05-28 Bristol-Myers Company Substituted vinyl cephalosporins
AU566944B2 (en) * 1983-10-07 1987-11-05 Gist-Brocades N.V. Preparation of 3-cephem derivatives

Also Published As

Publication number Publication date
FI861634A0 (en) 1986-04-17
FI84268C (en) 1991-11-11
CH671399A5 (en) 1989-08-31
HK106290A (en) 1990-12-28
IE861048L (en) 1986-10-22
JPH0327554B2 (en) 1991-04-16
SG90890G (en) 1991-01-18
AU589170B2 (en) 1989-10-05
DE3613365A1 (en) 1987-01-02
ZW9086A1 (en) 1986-12-03
GB2173798B (en) 1988-11-30
PT82436A (en) 1986-05-01
HU195223B (en) 1988-04-28
NZ215717A (en) 1989-06-28
FR2580652B1 (en) 1989-01-06
ES8800236A1 (en) 1987-10-16
SE500217C2 (en) 1994-05-09
SE8601825D0 (en) 1986-04-21
ES554215A0 (en) 1987-10-16
CS270435B2 (en) 1990-06-13
SE8601825L (en) 1986-10-23
ZM4286A1 (en) 1989-03-27
GB2173798A (en) 1986-10-22
FI84268B (en) 1991-07-31
CA1273629A (en) 1990-09-04
DK182486D0 (en) 1986-04-21
IE59014B1 (en) 1993-12-15
PT82436B (en) 1988-11-30
GR861065B (en) 1986-09-01
NO164659B (en) 1990-07-23
DK163584C (en) 1992-08-10
HUT41033A (en) 1987-03-30
FR2580652A1 (en) 1986-10-24
EG18001A (en) 1991-11-30
DK182486A (en) 1986-10-23
ATA106786A (en) 1990-07-15
LU86402A1 (en) 1986-11-05
NL8601011A (en) 1986-11-17
NO861430L (en) 1986-10-23
JPS61249989A (en) 1986-11-07
NL192205C (en) 1997-03-04
FI861634A (en) 1986-10-23
SU1435155A3 (en) 1988-10-30
CN86102630A (en) 1987-02-04
AT392072B (en) 1991-01-25
DE3613365C2 (en) 1989-06-15
CY1571A (en) 1991-12-20
AU5616886A (en) 1986-11-06
BE904646A (en) 1986-10-21
DK163584B (en) 1992-03-16
MY100694A (en) 1991-01-17
NL192205B (en) 1996-11-01
GB8609661D0 (en) 1986-05-29
OA08245A (en) 1987-10-30
DD244557A5 (en) 1987-04-08
CN1015714B (en) 1992-03-04
CS287286A2 (en) 1989-11-14
YU43697B (en) 1989-10-31
YU65986A (en) 1987-12-31
AR242581A1 (en) 1993-04-30
IT1228241B (en) 1991-06-05
NO164659C (en) 1990-10-31
IT8620162A0 (en) 1986-04-21
ZA862985B (en) 1986-12-30

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