GB1518329A - 7-methoxycephalosporin derivatives - Google Patents

7-methoxycephalosporin derivatives

Info

Publication number
GB1518329A
GB1518329A GB3284875A GB3284875A GB1518329A GB 1518329 A GB1518329 A GB 1518329A GB 3284875 A GB3284875 A GB 3284875A GB 3284875 A GB3284875 A GB 3284875A GB 1518329 A GB1518329 A GB 1518329A
Authority
GB
United Kingdom
Prior art keywords
compounds
amino
acetoxymethyl
heterocycle
amino group
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.)
Expired
Application number
GB3284875A
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.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries Ltd
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
Priority claimed from JP49091810A external-priority patent/JPS5119765A/en
Priority claimed from JP49125130A external-priority patent/JPS596879B2/en
Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of GB1518329A publication Critical patent/GB1518329A/en
Expired legal-status Critical Current

Links

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
    • C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
    • 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
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The compounds correspond to the formula <IMAGE> in which R<2> is hydrogen or halogen and R<3> is methyl, acetoxymethyl, carbamoylmethyl, alkoxymethyl, alkylthiomethyl, 2-carboxy-1-ethenyl or -CH2S-heterocycle. They are prepared by reacting 7 beta -amino-7 alpha -(methoxy-3-R<3>)-3-cephem-4-carboxylic acid or an alkali metal or amine salt or an ester thereof with a 2-[2-amino-5(R<2>)-4-thiazolyl]-acetic acid, the amino group of which is protected, or with a reactive functional derivative thereof; after this, the amino group and the carboxyl group, if esterified, are unblocked. Resulting 3-acetoxymethyl and 3-carbamoyloxymethyl compounds can be reacted with an alkyl mercaptan or an HS-heterocycle to give correspondingly substituted thiomethyl compounds. The compounds and their salts have a broad antimicrobial spectrum and are also particularly effective against antibiotic-resistant strains of Gram-negative bacteria; they can be used to treat infectious diseases.
GB3284875A 1974-08-09 1975-08-06 7-methoxycephalosporin derivatives Expired GB1518329A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP49091810A JPS5119765A (en) 1974-08-09 1974-08-09 Aminochiazoorujudotaino seizoho
JP49125130A JPS596879B2 (en) 1974-10-29 1974-10-29 7- Methoxycephalosporin

Publications (1)

Publication Number Publication Date
GB1518329A true GB1518329A (en) 1978-07-19

Family

ID=26433249

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3284875A Expired GB1518329A (en) 1974-08-09 1975-08-06 7-methoxycephalosporin derivatives

Country Status (7)

Country Link
CH (1) CH613457A5 (en)
DE (1) DE2534850C2 (en)
DK (1) DK151027C (en)
FR (1) FR2281369A1 (en)
GB (1) GB1518329A (en)
NL (1) NL180588C (en)
SE (1) SE429757B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1041983A1 (en) * 1997-12-23 2000-10-11 Newbiotics Inc. Application of enzyme prodrugs as anti-infective agents

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE416553B (en) * 1970-06-16 1981-01-19 Merck & Co Inc PROCEDURE FOR PREPARING NEW 7ALFA-SUBSTITUTED-7BETA-ACYLAMINOCEPHALOSPORANIC ACID COMPOUNDS
GB1348985A (en) * 1970-06-16 1974-03-27 Merck & Co Inc Esters of cephalosporin compounds
NZ176206A (en) * 1973-12-25 1978-03-06 Takeda Chemical Industries Ltd Cephalosporins

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1041983A1 (en) * 1997-12-23 2000-10-11 Newbiotics Inc. Application of enzyme prodrugs as anti-infective agents
EP1041983A4 (en) * 1997-12-23 2002-09-11 Newbiotics Inc Application of enzyme prodrugs as anti-infective agents

Also Published As

Publication number Publication date
DE2534850C2 (en) 1984-03-29
DE2534850A1 (en) 1976-02-19
NL7509391A (en) 1976-02-11
AU8378875A (en) 1977-02-10
DK151027B (en) 1987-10-12
SE7508913L (en) 1976-02-10
DK341775A (en) 1976-02-10
SE429757B (en) 1983-09-26
DK151027C (en) 1988-03-07
CH613457A5 (en) 1979-09-28
FR2281369A1 (en) 1976-03-05
NL180588C (en) 1987-03-16

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Legal Events

Date Code Title Description
PS Patent sealed
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PCNP Patent ceased through non-payment of renewal fee