KR830000246A - Development of cephalosporin antibiotics - Google Patents

Development of cephalosporin antibiotics Download PDF

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Publication number
KR830000246A
KR830000246A KR1019780001139A KR780001139A KR830000246A KR 830000246 A KR830000246 A KR 830000246A KR 1019780001139 A KR1019780001139 A KR 1019780001139A KR 780001139 A KR780001139 A KR 780001139A KR 830000246 A KR830000246 A KR 830000246A
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KR
South Korea
Prior art keywords
structural formula
compound
fur
hydrogen
oxide
Prior art date
Application number
KR1019780001139A
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Korean (ko)
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KR840000081B1 (en
Inventor
그렉손 미셀
Original Assignee
헤롤드 월티 마르틴
글락소 라보라 토리즈 리미티드
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Application filed by 헤롤드 월티 마르틴, 글락소 라보라 토리즈 리미티드 filed Critical 헤롤드 월티 마르틴
Publication of KR830000246A publication Critical patent/KR830000246A/en
Application granted granted Critical
Publication of KR840000081B1 publication Critical patent/KR840000081B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
    • 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
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
    • 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
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
    • C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings

Abstract

내용 없음No content

Description

세팔로스포린 항생제의 개발Development of cephalosporin antibiotics

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음This content is subject to disclosure, so the full text is not included.

Claims (1)

(6R,7R)-3-카리모일옥시메틸-7-[(Z)-2-(푸르-2-일)-2-메톡시이미노아세트아미도]세페-3-엠-4-카복실산(즉 세푸록심), 그의 염 또는 상응하는 1-옥사이드를 구조식(II)의 할로에스테르로 반응시키고 1-옥사이드가 형성되었을 때는 생성물을 환원시켜 구조식(I) 화합물을 생성하고 또한 구조식(III) 화합물 또는 그의 산부가염 또는 그의 N-실릴유도체를 (Z)-2-(푸르-2-일)-2-메톡시이미노아세트산에 상응하는 아실화제로 아실화시키거나 또한 구조식(IV)의 3-하이드록시메틸그룹을 카바모일화시켜서 다음 구조식(I) 화합물인 세팔로스포린 항생제를 제조하는 방법.(6R,7R)-3-carimoyloxymethyl-7-[(Z)-2-(fur-2-yl)-2-methoxyiminoacetamido]cepe-3-m-4-carboxylic acid ( In other words, cefuroxime), a salt thereof, or a corresponding 1-oxide is reacted with a haloester of structural formula (II), and when 1-oxide is formed, the product is reduced to produce a compound of structural formula (I), and a compound of structural formula (III) or Acylating its acid addition salt or its N-silyl derivative with an acylating agent corresponding to (Z)-2-(fur-2-yl)-2-methoxyiminoacetic acid or also 3-hydroxyl of formula (IV) A method of preparing a cephalosporin antibiotic which is a compound of the following structural formula (I) by carbamoylating a methyl group. t1 t1 상기 구조식에서In the above structural formula R1은 탄소수가 1 내지 6인 알킬그룹이고R 1 is an alkyl group having 1 to 6 carbon atoms R2는 수소 또는 탄소수가 1 내지 6인 알킬그룹이고R 2 is hydrogen or an alkyl group having 1 to 6 carbon atoms *표는 R2가 수소가 아닐 때는 비대칭탄소이고*The table shows asymmetric carbon when R 2 is not hydrogen X는 할로겐이다.X is halogen. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed according to the contents of the initial application.
KR7801139A 1977-04-19 1978-04-18 Process for preparing ceproxim ester KR840000081B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB16202/77 1977-04-19
GB16202/77A GB1598568A (en) 1977-04-19 1977-04-19 Esters of(6r,7r)-3-carbamoyloxymethyl-7-((z)-2-(fur-2-yl)-2-methoxyiminoacetamido)-ceph-3-em-4-carboxylic acid
GB16202/1977 1977-04-19

Publications (2)

Publication Number Publication Date
KR830000246A true KR830000246A (en) 1983-03-30
KR840000081B1 KR840000081B1 (en) 1984-02-08

Family

ID=10073017

Family Applications (1)

Application Number Title Priority Date Filing Date
KR7801139A KR840000081B1 (en) 1977-04-19 1978-04-18 Process for preparing ceproxim ester

Country Status (20)

Country Link
JP (1) JPS53132592A (en)
KR (1) KR840000081B1 (en)
AT (1) AT363183B (en)
AU (1) AU521098B2 (en)
BE (1) BE866093A (en)
CA (1) CA1093068A (en)
CH (1) CH639096A5 (en)
DE (1) DE2816873A1 (en)
DK (1) DK147513C (en)
ES (1) ES468895A1 (en)
FR (1) FR2387988A1 (en)
GB (1) GB1598568A (en)
IE (1) IE46726B1 (en)
IL (1) IL54531A (en)
IT (1) IT1104842B (en)
NL (1) NL7804097A (en)
NZ (1) NZ186998A (en)
SE (1) SE433748B (en)
YU (1) YU90978A (en)
ZA (1) ZA782211B (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2482587A1 (en) * 1980-05-14 1981-11-20 Poudres & Explosifs Ste Nale PROCESS FOR THE SYNTHESIS OF A-CHLORINATED CHLOROFORMIATES AND NEW A-CHLORINATED CHLOROFORMIATES
AU8166182A (en) * 1981-03-23 1982-09-30 Kyoto Yakuhin Kogyo K.K. Cephalosporin derivatives
FR2532933B1 (en) * 1982-06-29 1987-11-13 Astra Laekemedel Ab IMPROVEMENTS IN THE PREPARATION OF ANTIBIOTICS
GB2123821B (en) * 1982-06-29 1987-04-23 Astra Laekemedel Ab At-halogeno diethyl carbonates and their use in the preparation of antibiotics
IT1190897B (en) * 1982-06-29 1988-02-24 Opos Biochimica Srl PROCEDURE FOR THE PREPARATION OF THE 1-ETHOXYCARBONYLOXYETHYL ACID ACID 6- (D (-) - ALPHA AMINOALPHA-PHENYLACETAMIDE) -PENICILLANIC
IL68992A (en) * 1982-06-29 1991-06-10 Astra Laekemedel Ab Alpha-bromo diethyl carbonate and process for the preparation of ethoxycarbonyloxy esters of penicillanic acids
YU44680B (en) * 1982-07-30 1990-12-31 Glaxo Lab Ltd Process for obtaining very pure amorphous form of cephuroxim axetile
US4606865A (en) * 1982-09-20 1986-08-19 Astra Lakemedel Aktiebolag Methods for the preparation of α-bromodiethylcarbonate
IL67623A (en) * 1983-01-05 1984-09-30 Teva Pharma 1'-ethoxycarbonyloxyethyl ester of valproic acid,its preparation and pharmaceutical compositions containing it
GB8320521D0 (en) * 1983-07-29 1983-09-01 Glaxo Group Ltd Chemical process
FR2551058B1 (en) * 1983-08-26 1986-09-26 Poudres & Explosifs Ste Nale PROCESS FOR THE PREPARATION OF A-CHLORINATED CHLOROFORMIATES
GB8400024D0 (en) * 1984-01-03 1984-02-08 Glaxo Group Ltd Cephalosporin antibiotics
US4612143A (en) * 1984-09-17 1986-09-16 Societe Nationale Des Poudres Et Explosifs Process for the preparation of fluoroformates
US5202454A (en) * 1986-07-11 1993-04-13 Societe Nationale Des Poudres Et Explosifs Process for the manufacture of 1-bromoalkyl hydrocarbyl carbonates
KR100342944B1 (en) 1999-11-08 2002-07-02 민경윤 Method for preparing highly pure cefpodoxime proxetil
GB0301938D0 (en) * 2003-01-28 2003-02-26 Biochemie Gmbh Organic compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1453049A (en) * 1973-08-21 1976-10-20 Glaxo Lab Ltd Cephalosporing antibiotics
CA1093549A (en) * 1976-02-16 1981-01-13 Michael Gregson Cephalosporin antibiotics
CA1094545A (en) * 1976-02-16 1981-01-27 Michael Gregson Cephalosporin antibiotics

Also Published As

Publication number Publication date
BE866093A (en) 1978-10-18
FR2387988B1 (en) 1982-06-11
JPS53132592A (en) 1978-11-18
DE2816873A1 (en) 1978-11-02
ATA274878A (en) 1980-12-15
DK147513C (en) 1985-03-18
AU3518778A (en) 1979-10-25
CH639096A5 (en) 1983-10-31
DK147513B (en) 1984-09-10
YU90978A (en) 1983-01-21
IL54531A0 (en) 1978-07-31
SE7804400L (en) 1978-10-20
FR2387988A1 (en) 1978-11-17
NZ186998A (en) 1981-05-01
SE433748B (en) 1984-06-12
IL54531A (en) 1981-07-31
AT363183B (en) 1981-07-10
CA1093068A (en) 1981-01-06
ES468895A1 (en) 1978-12-01
AU521098B2 (en) 1982-03-18
GB1598568A (en) 1981-09-23
ZA782211B (en) 1979-04-25
DK168778A (en) 1978-10-20
NL7804097A (en) 1978-10-23
KR840000081B1 (en) 1984-02-08
IT7848941A0 (en) 1978-04-18
IE780760L (en) 1978-10-19
IT1104842B (en) 1985-10-28
IE46726B1 (en) 1983-09-07

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