KR850006420A - Method for preparing cephalosporin - Google Patents

Method for preparing cephalosporin Download PDF

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Publication number
KR850006420A
KR850006420A KR1019850001887A KR850001887A KR850006420A KR 850006420 A KR850006420 A KR 850006420A KR 1019850001887 A KR1019850001887 A KR 1019850001887A KR 850001887 A KR850001887 A KR 850001887A KR 850006420 A KR850006420 A KR 850006420A
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KR
South Korea
Prior art keywords
formula
salt
group
compound
substituted
Prior art date
Application number
KR1019850001887A
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Korean (ko)
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KR870001796B1 (en
Inventor
히로유끼 이마이즈미 (외 8)
Original Assignee
원본미기재
토야마카가꾸 코오교오 가부시끼 가이샤
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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Publication date
Priority claimed from JP59054522A external-priority patent/JPS60199894A/en
Priority claimed from JP59062226A external-priority patent/JPS60208986A/en
Priority claimed from JP59066649A external-priority patent/JPS60214783A/en
Application filed by 원본미기재, 토야마카가꾸 코오교오 가부시끼 가이샤 filed Critical 원본미기재
Publication of KR850006420A publication Critical patent/KR850006420A/en
Application granted granted Critical
Publication of KR870001796B1 publication Critical patent/KR870001796B1/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
    • C07D501/20—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
    • 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
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • 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
    • C07D501/02—Preparation
    • C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
    • 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
    • C07D501/02—Preparation
    • C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
    • C07D501/06—Acylation of 7-aminocephalosporanic acid

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

내용 없음No content

Description

세팔로스포린의 제조방법Method for preparing cephalosporin

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (4)

[A] 일반식(Ⅱ)의 화합물 또는 그의 염을 탈수 반응시키거나, [B] 일반식(Ⅵ)의 화합물을 티오우레아와 에틸아세테이트, 아세톤, 디옥산, 테트라하이드로프란, 아세토니트릴, 아세트산, 디클로로메탄, 클로로포름, 벤젠 및 1,2-디메톡시에탄 중에서 선택된 용매의 존재하에 -40°내지 30℃에서 반응시킨 후, 생성된 일반식(Ⅲ)의 화합물 또는 그의 염을 할로겐화제와 반응시켜, 생성된 일반식(Ⅳ)의 화합물 또는 그의 염을 일반식(V)의 화합물 또는 그의 염과 반응시킨 다음, 생성된 일반식(II)의 화합물 또는 그의 염을 탈수 반응시키고, 원한다며 [A] 또는 [B]단계후 보호그룹을 제거하거나 카복실그룹을 보호하거나 또는 생성물을 그의 염으로 전환시킴을 특징으로 하여 일반식(I)의 세팔로스포린 또는 그의 염을 제조하는 방법.[A] The compound of formula (II) or salt thereof is dehydrated, or [B] the compound of formula (VI) is thiourea with ethyl acetate, acetone, dioxane, tetrahydrofran, acetonitrile, acetic acid, After reaction at −40 ° to 30 ° C. in the presence of a solvent selected from dichloromethane, chloroform, benzene and 1,2-dimethoxyethane, the resulting compound of general formula (III) or a salt thereof is reacted with a halogenating agent, Reacting the resulting compound of formula (IV) or a salt thereof with a compound of formula (V) or a salt thereof, followed by a dehydration reaction of the resulting compound of formula (II) or a salt thereof [A] or A process for preparing cephalosporin of formula (I) or a salt thereof characterized by removing the protecting group after step [B], protecting the carboxyl group, or converting the product to a salt thereof. 상기 식에서, R1은 카복실 또는 보호된 카복실 그룹으로 임의치환될 수 있는 저급알킬 그룹이고; R2는 수소원자 또는 카복실보호그룹이며; R3는 C-N 결합을 통해 세펨환의 3위치의 엑소메티렌 그룹에 결합된 치환된 또는 비치환 헤테로사이클릭 그룹이고; R4는 치환된 또는 비치환알킬, 아르알킬 또는 아릴그룹이며; X는 할로겐원자이고; 결합는 일반식(Ⅵ)의 화합물이 syn 이성체 또는 ant 이성체이거나 이들 이성체 혼합물임을 나타낸다.Wherein R 1 is a lower alkyl group which may be optionally substituted with a carboxyl or protected carboxyl group; R 2 is a hydrogen atom or a carboxyl protecting group; R 3 is a substituted or unsubstituted heterocyclic group bonded to the exomethylene group at the 3-position of the cefme ring via a CN bond; R 4 is substituted or unsubstituted alkyl, aralkyl or aryl group; X is a halogen atom; Combination Denotes that the compound of formula (VI) is a syn isomer or an ant isomer or a mixture of these isomers. 제1항에 있어서, R2가 아실옥시알킬 그룹인 일반식(I)의 세팔로스포린 또는 그의 염을 제조하는 방법.The process for preparing cephalosporin of formula (I) or a salt thereof according to claim 1, wherein R 2 is an acyloxyalkyl group. 제1항 또는 2항에 있어서, R3가 C-N 결합을 통해 세펨환의 3위치의 엑소메틸렌 그룹에 결합된 치환된 또는 비치환 1,2,3,4-테트라졸릴 또는 1,2,4-트티아졸릴 그룹인 일반식(I)의 세팔로스포린 또는 그의 염을 제조하는 방법. 3. A substituted or unsubstituted 1,2,3,4-tetrazolyl or 1,2,4-tet according to claim 1 or 2, wherein R 3 is bonded to the exomethylene group at the 3-position of the cefe ring via a CN bond. A process for preparing cephalosporin of formula (I) or a salt thereof, which is a thiazolyl group. 제1항 내지 3항중 어느 하나에 있어서, R4가 비치환알킬 그룹인 일반식(I)의 세팔로스포린 또는 그의 염을 제조하는 방법.The process for preparing cephalosporin of formula (I) or a salt thereof according to any one of claims 1 to 3, wherein R 4 is an unsubstituted alkyl group. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019850001887A 1984-03-23 1985-03-22 Process for preparing cephalosporins KR870001796B1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP54522/84 1984-03-23
JP59054522A JPS60199894A (en) 1984-03-23 1984-03-23 Novel preparation of cephalosporin
JP62226/84 1984-03-31
JP59062226A JPS60208986A (en) 1984-03-31 1984-03-31 Novel cephalosporin
JP59066649A JPS60214783A (en) 1984-04-05 1984-04-05 2-amino-4-hydroxythiazoline derivative and its salt
JP66649/84 1984-04-05

Publications (2)

Publication Number Publication Date
KR850006420A true KR850006420A (en) 1985-10-05
KR870001796B1 KR870001796B1 (en) 1987-10-12

Family

ID=27295315

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019850001887A KR870001796B1 (en) 1984-03-23 1985-03-22 Process for preparing cephalosporins

Country Status (10)

Country Link
KR (1) KR870001796B1 (en)
AR (1) AR243192A1 (en)
AT (1) AT386207B (en)
CH (2) CH673460A5 (en)
DK (1) DK132585A (en)
ES (1) ES8602814A1 (en)
FI (1) FI86184C (en)
NO (1) NO167574C (en)
PL (1) PL145915B1 (en)
PT (1) PT80154B (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CY1365A (en) * 1980-03-28 1987-08-07 Biochemie Gmbh New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production

Also Published As

Publication number Publication date
PL252525A1 (en) 1985-12-17
CH673460A5 (en) 1990-03-15
NO167574B (en) 1991-08-12
CH669383A5 (en) 1989-03-15
NO167574C (en) 1991-11-20
PT80154B (en) 1987-06-17
PL145915B1 (en) 1988-11-30
KR870001796B1 (en) 1987-10-12
AT386207B (en) 1988-07-25
AR243192A1 (en) 1993-07-30
FI86184C (en) 1992-07-27
ES541520A0 (en) 1985-12-01
ATA86985A (en) 1987-12-15
DK132585D0 (en) 1985-03-22
FI86184B (en) 1992-04-15
NO851166L (en) 1985-09-24
FI851173L (en) 1985-09-24
FI851173A0 (en) 1985-03-22
DK132585A (en) 1985-09-24
PT80154A (en) 1985-04-01
ES8602814A1 (en) 1985-12-01

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