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GB1512957A - Gephalosporin antibiotics - Google Patents

Gephalosporin antibiotics

Info

Publication number
GB1512957A
GB1512957A GB37197/74A GB3719774A GB1512957A GB 1512957 A GB1512957 A GB 1512957A GB 37197/74 A GB37197/74 A GB 37197/74A GB 3719774 A GB3719774 A GB 3719774A GB 1512957 A GB1512957 A GB 1512957A
Authority
GB
United Kingdom
Prior art keywords
denotes
syn
phenyl
formula
rdurule
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
GB37197/74A
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories 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
Application filed by Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB37197/74A priority Critical patent/GB1512957A/en
Priority to DK378975A priority patent/DK147338C/en
Priority to AU84217/75A priority patent/AU501819B2/en
Priority to NL7509948A priority patent/NL7509948A/en
Priority to AT651575A priority patent/AT343280B/en
Priority to JP50101973A priority patent/JPS5143794A/en
Priority to ZA755392A priority patent/ZA755392B/en
Priority to CA233,953A priority patent/CA1070673A/en
Priority to DE19752537558 priority patent/DE2537558A1/en
Priority to SE7509403A priority patent/SE433355B/en
Priority to CH1091375A priority patent/CH620215A5/en
Priority to FR7526009A priority patent/FR2282275A1/en
Priority to BE159381A priority patent/BE832651R/en
Priority to US05/749,299 priority patent/US4122259A/en
Priority to AT362677A priority patent/AT343815B/en
Publication of GB1512957A publication Critical patent/GB1512957A/en
Priority to CH582679A priority patent/CH626087A5/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
    • C07D501/24—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
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

Syn-isomers or mixtures of syn- and anti-isomers, the amount of the syn-isomer being at least 90%, of novel antibiotically active 7 beta -acylamidoceph-3-em-4-carboxylic acids of the formula I, in which R denotes furyl, thienyl or phenyl; R<a> denotes C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C7-cycloalkyl or phenyl; R<s> denotes C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C7-cycloalkyl, benzyl or phenyl; and B denotes &rdurule& S or &rdurule& S->O are prepared by reacting an appropriate 3-hydroxymethyl compound, optionally with intermediate protection of the 4-carboxyl group, with an isocyanate of the formula R<s>-NCO. Resulting 1-sulphoxides of the formula I can be reduced to the corresponding 1-sulphides. Resulting ceph-2-em compounds are isomerised to the corresponding ceph-3-em compounds. The process products are distinguished by a broad spectrum of antibiotic action in combination with high beta -lactamase stability and by a good stability in vivo. <IMAGE>
GB37197/74A 1974-08-23 1974-08-23 Gephalosporin antibiotics Expired GB1512957A (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
GB37197/74A GB1512957A (en) 1974-08-23 1974-08-23 Gephalosporin antibiotics
CA233,953A CA1070673A (en) 1974-08-23 1975-08-22 7.beta.-(2-ARYL-2-(ETHERIFIED OXIMINO) ACETAMIDO) -3-N-SUBSTITUTED CARBAMOYLOXYMETHYLCEPH-3-EM-4-CARBOXYLIC ACIDS
CH1091375A CH620215A5 (en) 1974-08-23 1975-08-22 Process for the preparation of a syn-isomer or a mixture of syn- and anti-isomers of novel antibiotically active 7-beta-acylamidoceph-3-em-4-carboxylic acids
NL7509948A NL7509948A (en) 1974-08-23 1975-08-22 PROCESS FOR THE PREPARATION OF ANTIBIOTICS.
AT651575A AT343280B (en) 1974-08-23 1975-08-22 METHOD FOR PRODUCING NEW CEPHALOSPORINE COMPOUNDS
JP50101973A JPS5143794A (en) 1974-08-23 1975-08-22 Sefuarosuhorinno seiho
ZA755392A ZA755392B (en) 1974-08-23 1975-08-22 Improvements in or relating to antibiotics
DK378975A DK147338C (en) 1974-08-23 1975-08-22 METHOD OF ANALOGUE FOR THE PREPARATION OF CEPHALOSPOR COMPOUNDS OR SALTS OR BIOLOGICAL ACCEPTABLE ESTERS THEREOF
DE19752537558 DE2537558A1 (en) 1974-08-23 1975-08-22 CEPHALOSPORIN ANTIBIOTICS
SE7509403A SE433355B (en) 1974-08-23 1975-08-22 PROCEDURE FOR THE PRODUCTION OF CEPHALOSPORINE DERIVATIVES
AU84217/75A AU501819B2 (en) 1974-08-23 1975-08-22 Cephalosporins
FR7526009A FR2282275A1 (en) 1974-08-23 1975-08-22 IMPROVEMENTS RELATED TO ANTIBIOTICS
BE159381A BE832651R (en) 1974-08-23 1975-08-22 IMPROVEMENTS RELATED TO ANTIBIOTICS
US05/749,299 US4122259A (en) 1974-08-23 1976-12-10 7β-[2-Aryl-2-(etherified oximino)acetamido]-3-N-substituted carbamoyloxymethylceph-3-em-4-carboxylic acids
AT362677A AT343815B (en) 1974-08-23 1977-05-20 PROCESS FOR PRODUCING NEW CEPHALOSPORIN COMPOUNDS
CH582679A CH626087A5 (en) 1974-08-23 1979-06-21 Process for the preparation of a syn isomer or a mixture of syn and anti isomers of 7beta-acylamidoceph-3-em-4-carboxylic acids with antibiotic activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB37197/74A GB1512957A (en) 1974-08-23 1974-08-23 Gephalosporin antibiotics

Publications (1)

Publication Number Publication Date
GB1512957A true GB1512957A (en) 1978-06-01

Family

ID=10394577

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37197/74A Expired GB1512957A (en) 1974-08-23 1974-08-23 Gephalosporin antibiotics

Country Status (13)

Country Link
JP (1) JPS5143794A (en)
AT (1) AT343280B (en)
AU (1) AU501819B2 (en)
BE (1) BE832651R (en)
CA (1) CA1070673A (en)
CH (2) CH620215A5 (en)
DE (1) DE2537558A1 (en)
DK (1) DK147338C (en)
FR (1) FR2282275A1 (en)
GB (1) GB1512957A (en)
NL (1) NL7509948A (en)
SE (1) SE433355B (en)
ZA (1) ZA755392B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4278887A (en) * 1980-02-04 1981-07-14 Technicon Instruments Corporation Fluid sample cell

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1399086A (en) * 1971-05-14 1975-06-25 Glaxo Lab Ltd Cephalosporin compounds

Also Published As

Publication number Publication date
NL7509948A (en) 1976-02-25
JPS5143794A (en) 1976-04-14
AU8421775A (en) 1977-03-03
CH626087A5 (en) 1981-10-30
CH620215A5 (en) 1980-11-14
AT343280B (en) 1978-05-26
DK147338B (en) 1984-06-25
SE433355B (en) 1984-05-21
FR2282275A1 (en) 1976-03-19
BE832651R (en) 1976-02-23
FR2282275B2 (en) 1979-06-15
ATA651575A (en) 1977-09-15
DK378975A (en) 1976-02-24
DE2537558A1 (en) 1976-03-04
DK147338C (en) 1985-01-02
AU501819B2 (en) 1979-06-28
ZA755392B (en) 1977-04-27
CA1070673A (en) 1980-01-29

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Legal Events

Date Code Title Description
PS Patent sealed