FR2421904A2 - 3-Carbamoyloxy-methyl-7-thiazolyl-acetamido cephalosporin derivs. - prepd. from 3-acetoxymethyl cpd. by enzymatic de-acetylation and reaction with isocyanate, useful as antibiotics - Google Patents

3-Carbamoyloxy-methyl-7-thiazolyl-acetamido cephalosporin derivs. - prepd. from 3-acetoxymethyl cpd. by enzymatic de-acetylation and reaction with isocyanate, useful as antibiotics

Info

Publication number
FR2421904A2
FR2421904A2 FR7726059A FR7726059A FR2421904A2 FR 2421904 A2 FR2421904 A2 FR 2421904A2 FR 7726059 A FR7726059 A FR 7726059A FR 7726059 A FR7726059 A FR 7726059A FR 2421904 A2 FR2421904 A2 FR 2421904A2
Authority
FR
France
Prior art keywords
thiazolyl
reaction
enzymatic
antibiotics
hydrolysis
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.)
Granted
Application number
FR7726059A
Other languages
French (fr)
Other versions
FR2421904B2 (en
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to FR7726059A priority Critical patent/FR2421904A2/en
Publication of FR2421904A2 publication Critical patent/FR2421904A2/en
Application granted granted Critical
Publication of FR2421904B2 publication Critical patent/FR2421904B2/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • C07D277/587—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 aliphatic hydrocarbon radicals substituted by 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, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

Parent patent describes new cephalosporins of formula (I), syn or anti, where R = H or gp. easily removed by acid hydrolysis or hydrogenolysis. R1 = 1-4C, opt. unsatd. alkyl. A = H or an equiv. of an alkali, alkaline earth, Mg or amine cation. This addition describes the prodn. of (I) from cpds. (V) (where R1 = R other than H) by (i) enzymatic deacetylation; (ii) reaction with R2NCO (R2 = gp. easily removed by hydrolysis) then (iii) hydrolysis to give (I; R = R1), opt. followed by removal of R1 to give (I; R = H). In an alternative R1 is replaced by chloroacetyl which is removed in the final stage with thiourea. Also new are the Na salt of the syn isomer of 3-carbamoyloxymethyl-7- 2-(2-amino-4-thiazolyl)-2-methoxyimino-ac- etamido -ceph-3-en-4-carboxylic acid. (Ia); and intermediates of formula (II) (where Q is chloroacetyl and D is H or CONHR2, R2' = H or R2; or, Q is R1 and D is H or CONHR2). (I) are antibiotics useful against Gram positive or negative bacteria, including penicillin-resistant Staphylococci.
FR7726059A 1977-08-26 1977-08-26 3-Carbamoyloxy-methyl-7-thiazolyl-acetamido cephalosporin derivs. - prepd. from 3-acetoxymethyl cpd. by enzymatic de-acetylation and reaction with isocyanate, useful as antibiotics Granted FR2421904A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7726059A FR2421904A2 (en) 1977-08-26 1977-08-26 3-Carbamoyloxy-methyl-7-thiazolyl-acetamido cephalosporin derivs. - prepd. from 3-acetoxymethyl cpd. by enzymatic de-acetylation and reaction with isocyanate, useful as antibiotics

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7726059A FR2421904A2 (en) 1977-08-26 1977-08-26 3-Carbamoyloxy-methyl-7-thiazolyl-acetamido cephalosporin derivs. - prepd. from 3-acetoxymethyl cpd. by enzymatic de-acetylation and reaction with isocyanate, useful as antibiotics

Publications (2)

Publication Number Publication Date
FR2421904A2 true FR2421904A2 (en) 1979-11-02
FR2421904B2 FR2421904B2 (en) 1983-04-29

Family

ID=9194805

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7726059A Granted FR2421904A2 (en) 1977-08-26 1977-08-26 3-Carbamoyloxy-methyl-7-thiazolyl-acetamido cephalosporin derivs. - prepd. from 3-acetoxymethyl cpd. by enzymatic de-acetylation and reaction with isocyanate, useful as antibiotics

Country Status (1)

Country Link
FR (1) FR2421904A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0155103A2 (en) * 1984-02-24 1985-09-18 Kureha Kagaku Kogyo Kabushiki Kaisha Cephalosporin derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0155103A2 (en) * 1984-02-24 1985-09-18 Kureha Kagaku Kogyo Kabushiki Kaisha Cephalosporin derivatives
EP0155103A3 (en) * 1984-02-24 1986-07-23 Kureha Kagaku Kogyo Kabushiki Kaisha Cephalosporin derivatives
US4734409A (en) * 1984-02-24 1988-03-29 Kureha Kagaku Kogyo Kabushiki Kaisha Cephalosporin derivative, process for producing the same and pharmaceutical composition containing the same

Also Published As

Publication number Publication date
FR2421904B2 (en) 1983-04-29

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