GB1445446A - Preparation of 7-substituted cephalosporins - Google Patents

Preparation of 7-substituted cephalosporins

Info

Publication number
GB1445446A
GB1445446A GB5394573A GB5394573A GB1445446A GB 1445446 A GB1445446 A GB 1445446A GB 5394573 A GB5394573 A GB 5394573A GB 5394573 A GB5394573 A GB 5394573A GB 1445446 A GB1445446 A GB 1445446A
Authority
GB
United Kingdom
Prior art keywords
cephalosporanate
benzalimino
substituted
prepared
methylthio
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
GB5394573A
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.)
ER Squibb and Sons LLC
Original Assignee
ER Squibb and Sons LLC
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 US394944A external-priority patent/US3910902A/en
Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC
Publication of GB1445446A publication Critical patent/GB1445446A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1445446 Preparation of 7-substituted cephalosporins E R SQUIBB & SONS Inc 21 Nov 1973 [6 Dec 1972 (2) 6 Sept 1973 (2)] 53945/73 Heading C2C Compounds I (R 1 is acylamino, phthalimido, benzalimino or optionally substituted benzalimino; R 3 is H a readily clearable esterifying group or a cation; R 4 is methyl, acetoxymethyl, or carbamoyloxymethyl; and R 5 is 1-6 C alkoxy, 1-6 C alkanoyloxy, benzoyloxy, α- or #-naphthoyloxy, aryloxy, azido, NH 2 or mono- or di- 1-6 C alkylamino) are prepared by replacing the R 2 group in a compound II (R 2 is 1-6 C alkanoyloxy, aroyloxy, 1-6 C alkylthio, arylthio, substituted arylthio, aryl- 1-6 C alkylthio, or substituted arylÀ1-6 C alkylthio) by reaction with an appropriate alkanol, alkanoic acid or salt thereof, benzoic acid, α- or #-naphthoic acid, phenol or salt thereof, NH 3 , amine or azide in the presence of a catalyst which is a salt of Hg, Ag, Cu, Pb or Th. Starting materials prepared are t-butyl 7α- methylthio - 7 - benzalimino - desacetoxy - cephalosporanate (by methylthiolation of the Schiff base); and t - butyl 7α - methylthio - 7 - benzalimino - cephalosporanate, p - methoxybenzyl. 7α - Phenylthio - 7 - (p - nitrobenzalimino)cephalosporanate, and t - butyl 7α - ethylthio - 7- (p - methoxybenzalimino)- desacetoxy - cephalosporanate (all prepared similarly); and tbutyl 7α - methylthio - 7 - phenylacetamido cephalosporanate or desacetoxycephalosporanate (prepared by reaction of the appropriate Schiff base above with phenylacetyl chloride).
GB5394573A 1972-12-06 1973-11-21 Preparation of 7-substituted cephalosporins Expired GB1445446A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US31247172A 1972-12-06 1972-12-06
US31243672A 1972-12-06 1972-12-06
US39494373A 1973-09-06 1973-09-06
US394944A US3910902A (en) 1972-12-06 1973-09-06 Method for preparing 7-substituted cephalosporins by replacement of oxygen containing groups

Publications (1)

Publication Number Publication Date
GB1445446A true GB1445446A (en) 1976-08-11

Family

ID=27502033

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5394573A Expired GB1445446A (en) 1972-12-06 1973-11-21 Preparation of 7-substituted cephalosporins

Country Status (5)

Country Link
JP (1) JPS4986391A (en)
CA (1) CA1018968A (en)
DE (1) DE2360945A1 (en)
FR (1) FR2209762B1 (en)
GB (1) GB1445446A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2161803A (en) * 1981-07-25 1986-01-22 Beecham Group Plc Intermediates for beta -lactam antibiotics

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JO1395B1 (en) * 1981-07-10 1986-11-30 بيتشام جروب بي ال سي Process for the preparation of penam derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2161803A (en) * 1981-07-25 1986-01-22 Beecham Group Plc Intermediates for beta -lactam antibiotics

Also Published As

Publication number Publication date
FR2209762A1 (en) 1974-07-05
CA1018968A (en) 1977-10-11
FR2209762B1 (en) 1977-02-18
DE2360945A1 (en) 1974-06-12
JPS4986391A (en) 1974-08-19

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee