ES8107229A1 - Novel thiol esters and manufacture - Google Patents

Novel thiol esters and manufacture

Info

Publication number
ES8107229A1
ES8107229A1 ES496194A ES496194A ES8107229A1 ES 8107229 A1 ES8107229 A1 ES 8107229A1 ES 496194 A ES496194 A ES 496194A ES 496194 A ES496194 A ES 496194A ES 8107229 A1 ES8107229 A1 ES 8107229A1
Authority
ES
Spain
Prior art keywords
alkyl
active against
staph
dioxo
opt
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
ES496194A
Other languages
Spanish (es)
Other versions
ES496194A0 (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.)
Rhone Poulenc Industries SA
Original Assignee
Rhone Poulenc Industries 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 Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA
Publication of ES8107229A1 publication Critical patent/ES8107229A1/en
Publication of ES496194A0 publication Critical patent/ES496194A0/en
Granted 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
    • C07D501/24—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

Landscapes

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

Abstract

3-Thiovinyl-cephalosporin of formula (I) having syn or anit, E or Z forms and their mixtures including their acid addition, metallic and N-base addition salts are new. In (I) R is e.g. alkyl, L-2-amino-2-carboxy-ethyl phenyl 2-, 3- or 4-pyridyl and their (N-oxides) 2-pyrimidinyl 3-pyridazinyl substd. in position 6 and opt. N-oxidised or tetrazolo(4,5-b)pyridazin-6-cyl 4) 1,4-dialkyl or 1-alkyl-5,6-dioxo 1,4,5,6-tetrahydro-1, 2,4-trazin-3-yl or 2-alkyl-5,6-dioxo-1,2,5,6-dioxi-1,2,5,6-tetrahydro-1,2,4-triazin-- 3-yl 6) Ro is H, alkyl, vinyl or cyanomethyl R1 is H or a group-CH(R2)(OOCR3) (easily removed by enzymes) (where R2=H or alkyl and R3= alkyl or cyclohexyl. The alkyl and acyl radicals above except where specifically specified are opt-branched and contain 1-4C atoms). (I) are a antibacterials active against gram-negative and gram-positive. In vitro tests show (I) are active against penicillin G sensitive Staph aireus (Staph aureus Smith) at 0.5-15 mg/cc and against penicillin G resistant strains (Staph. aureus MB 9) at 1-30 ug/cc. They are active against E. coli Monod at 0.001-ug/cc and against Kledsiella pneumonae at 0.06-30 ug/cc. Some cpds. are active against Proteus morganii (0.01-30ug/cc) and Enterobacter aerogenes (0.1-30ug/cc)sub-cultaneous LD50 of (I) in mice is 1.5-2.5 g/kg. Admin. may be oral, rectat, parenteral or topical.
ES496194A 1980-02-12 1980-10-23 PROCEDURE FOR OBTAINING THIOVINYL-3 CEPHALOSPORINS Granted ES496194A0 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8003057A FR2475545A1 (en) 1980-02-12 1980-02-12 7-Amino-thiazolyl methoxy-imino acetamido 3-thio-vinyl-cephalosporin - antibacterials active against Gram negative and Gram positive bacteria

Publications (2)

Publication Number Publication Date
ES8107229A1 true ES8107229A1 (en) 1981-10-01
ES496194A0 ES496194A0 (en) 1981-10-01

Family

ID=9238493

Family Applications (1)

Application Number Title Priority Date Filing Date
ES496194A Granted ES496194A0 (en) 1980-02-12 1980-10-23 PROCEDURE FOR OBTAINING THIOVINYL-3 CEPHALOSPORINS

Country Status (6)

Country Link
JP (1) JPS56127375A (en)
ES (1) ES496194A0 (en)
FR (1) FR2475545A1 (en)
PL (1) PL127301B1 (en)
SU (1) SU1098522A3 (en)
YU (1) YU58483A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2346014A1 (en) * 1976-01-23 1977-10-28 Roussel Uclaf Amino-thiazolyl-hydroxyimino-acetamido-cephalosporanic acids - with antibacterial activity
DE2804040C3 (en) * 1978-01-31 1981-03-19 Hoechst Ag, 6000 Frankfurt Process for the preparation of cephem compounds

Also Published As

Publication number Publication date
PL127301B1 (en) 1983-10-31
YU58483A (en) 1984-02-29
ES496194A0 (en) 1981-10-01
FR2475545B1 (en) 1983-09-30
JPS56127375A (en) 1981-10-06
SU1098522A3 (en) 1984-06-15
FR2475545A1 (en) 1981-08-14

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19990601