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GB1496757A - Cephalosporin derivatives - Google Patents

Cephalosporin derivatives

Info

Publication number
GB1496757A
GB1496757A GB59517/73A GB5951773A GB1496757A GB 1496757 A GB1496757 A GB 1496757A GB 59517/73 A GB59517/73 A GB 59517/73A GB 5951773 A GB5951773 A GB 5951773A GB 1496757 A GB1496757 A GB 1496757A
Authority
GB
United Kingdom
Prior art keywords
compounds
isocyanate
syn isomers
labile substituent
cephalosporin derivatives
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
GB59517/73A
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 GB59517/73A priority Critical patent/GB1496757A/en
Priority to PH16670A priority patent/PH11646A/en
Priority to DK674674A priority patent/DK674674A/da
Priority to CA216,571A priority patent/CA1059991A/en
Priority to SE7416195A priority patent/SE7416195L/en
Priority to CH1708674A priority patent/CH617703A5/en
Priority to ZA00748146A priority patent/ZA748146B/en
Priority to HU74GA00001174A priority patent/HU172234B/en
Priority to BE151755A priority patent/BE823651A/en
Priority to FI3713/74A priority patent/FI65258C/en
Priority to IE2639/74A priority patent/IE42144B1/en
Priority to NO744621A priority patent/NO744621L/no
Priority to JP49147519A priority patent/JPS5844675B2/en
Priority to LU71550A priority patent/LU71550A1/xx
Priority to IL46302A priority patent/IL46302A/en
Priority to DE2460537A priority patent/DE2460537C2/en
Priority to AT1020174A priority patent/AT344888B/en
Priority to NL7416665A priority patent/NL7416665A/en
Priority to AU76735/74A priority patent/AU486433B2/en
Priority to ES433226A priority patent/ES433226A1/en
Priority to FR7442541A priority patent/FR2255076B1/fr
Priority to MX608775U priority patent/MX5478E/en
Priority to US05/668,245 priority patent/US4144393A/en
Priority to US05/668,246 priority patent/US4060686A/en
Priority to US05/668,244 priority patent/US4095021A/en
Priority to US05/668,529 priority patent/US4103084A/en
Priority to US05/696,438 priority patent/US4144392A/en
Priority to ES451604A priority patent/ES451604A1/en
Priority to AT832076A priority patent/AT362500B/en
Priority to FR7725559A priority patent/FR2355849A1/en
Priority to US05/832,956 priority patent/US4162360A/en
Publication of GB1496757A publication Critical patent/GB1496757A/en
Priority to CA314,938A priority patent/CA1067068A/en
Priority to CA314,937A priority patent/CA1067067A/en
Priority to AT51179A priority patent/ATA51179A/en
Priority to AT51279A priority patent/ATA51279A/en
Priority to AT13680A priority patent/AT367061B/en
Priority to CH449880A priority patent/CH626370A5/en
Priority to JP13056680A priority patent/JPS5655392A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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 is thienyl or furyl and R' is hydrogen or C1-C4-alkyl, and the other symbols have the meanings stated in Claim 1; they are in the form of syn isomers or of mixtures containing at least 90% syn isomers. They are prepared starting from appropriate 3-hydroxymethyl compounds by a carbamoylation reaction, in particular with cyanic acid or an isocyanate R<e>-NCO in which R<e> is a labile substituent, e.g. with chlorosulphonyl isocyanate. Any carboxyl protective groups or the labile substituent on the carbamoyl nitrogen atom are then eliminated. The compounds are antibiotics with a broad spectrum of action and particularly high activity on Gram-negative microorganisms, including those which produce 2-lactamase.
GB59517/73A 1973-12-21 1973-12-21 Cephalosporin derivatives Expired GB1496757A (en)

Priority Applications (38)

Application Number Priority Date Filing Date Title
GB59517/73A GB1496757A (en) 1973-12-21 1973-12-21 Cephalosporin derivatives
PH16670A PH11646A (en) 1973-12-21 1974-12-17 7-(carboxy substituted-etherified oximino arylacetamido)cephalosporins
ES433226A ES433226A1 (en) 1973-12-21 1974-12-20 A process for the preparation of cephalosporin antibiotic compounds. (Machine-translation by Google Translate, not legally binding)
DE2460537A DE2460537C2 (en) 1973-12-21 1974-12-20 7-β-Acylamido-3-em-4-carboxylic acid antibiotics
SE7416195A SE7416195L (en) 1973-12-21 1974-12-20 PROCEDURE FOR THE PREPARATION OF CEPHALOSPORINS.
CH1708674A CH617703A5 (en) 1973-12-21 1974-12-20 Process for the preparation of the syn-isomer or of a mixture of syn- and anti-isomers of novel antibiotically active 7 beta -acylamino-ceph-3-em-4-carboxylic acids
ZA00748146A ZA748146B (en) 1973-12-21 1974-12-20 Improvements in or relating to antibiotics
HU74GA00001174A HU172234B (en) 1973-12-21 1974-12-20 Process for producing new derivatives of 7-beta-acylamido-ceph-3-eme-4-carboxylic acid
BE151755A BE823651A (en) 1973-12-21 1974-12-20 NEW CEPHALOSPORINS
FI3713/74A FI65258C (en) 1973-12-21 1974-12-20 FORM OF ANTIBIOTICS VERKANDE 7-ETA-ACYLAMIDOCEF-3-EM-4-CARBOXYLSYRA
IE2639/74A IE42144B1 (en) 1973-12-21 1974-12-20 Improvements in or relating to antibiotics
NO744621A NO744621L (en) 1973-12-21 1974-12-20
JP49147519A JPS5844675B2 (en) 1973-12-21 1974-12-20 The best way to go about it
LU71550A LU71550A1 (en) 1973-12-21 1974-12-20
IL46302A IL46302A (en) 1973-12-21 1974-12-20 7 -( -(etherified oxyimino)-acylamido)cephalosporanic acid derivatives
CA216,571A CA1059991A (en) 1973-12-21 1974-12-20 CEPHALOSPORINS HAVING A 7-(CARBOXY SUBSTITUTED .alpha.-ETHERIFIED OXIMINOARYLACETAMIDO) GROUP
AT1020174A AT344888B (en) 1973-12-21 1974-12-20 PROCESS FOR THE MANUFACTURING OF NEW CEPHALOSPORIN ANTIBIOTICS
NL7416665A NL7416665A (en) 1973-12-21 1974-12-20 METHOD FOR PREPARING CEPHALOSPORIN COMPOUNDS.
AU76735/74A AU486433B2 (en) 1973-12-21 1974-12-20 7-acylamidoceph-3-em-4-carboxylic acid antibiotics
DK674674A DK674674A (en) 1973-12-21 1974-12-20
FR7442541A FR2255076B1 (en) 1973-12-21 1974-12-23
MX608775U MX5478E (en) 1973-12-21 1975-01-02 PROCEDURE FOR THE PREPARATION OF CEPHALOSPORIN COMPOUNDS
US05/668,244 US4095021A (en) 1973-12-21 1976-03-18 3-Carbamoyloxymethyl or N-methyl-carbamoyloxymethyl-7-[2-carboxymethoxyimino-2-(fur-2-yl or thien-2-yl)acetamido]ceph-3-em-4-carboxylic acids and derivatives thereof
US05/668,245 US4144393A (en) 1973-12-21 1976-03-18 3-Acetoxymethyl cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyiminoarylacetamido group
US05/668,246 US4060686A (en) 1973-12-21 1976-03-18 Cephalosporins having a 7-(carboxy substituted α-etherified oximinoarylacetamido) group
US05/668,529 US4103084A (en) 1973-12-21 1976-03-19 7-(Carboxy substituted α-etherified oximino arylacetamido) cephalosporins having a 3-vinyl or substituted vinyl group
US05/696,438 US4144392A (en) 1973-12-21 1976-06-15 Cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyimino-arylacetamido group and at position-3 the residue of a sulphur nucleophile
ES451604A ES451604A1 (en) 1973-12-21 1976-09-16 A procedure for preparation. (Machine-translation by Google Translate, not legally binding)
AT832076A AT362500B (en) 1973-12-21 1976-11-09 METHOD FOR PRODUCING NEW CEPHALOS-PORIN ANTIBIOTICS
FR7725559A FR2355849A1 (en) 1973-12-21 1977-08-22 7 B-ACYLAMIDOCEPH-3-EME 4-CARBOXYL ACID DERIVATIVES, THEIR PROCESS OF PREPARATION AND THERAPEUTIC APPLICATION
US05/832,956 US4162360A (en) 1973-12-21 1977-09-13 3-Carbamoyloxymethyl-7-substituted oximino acetamido cephalosporanic acid derivatives
CA314,938A CA1067068A (en) 1973-12-21 1978-10-30 3-CARBAMOYLOXYMETHYL-7-(.alpha.-(1-CARBOXYCYCLOBUT-1-OXYIMINO)-.alpha.-(FUR-2-YL) ACETAMIDO) CEPH-3-EM-4-CARBOXYLIC ACID
CA314,937A CA1067067A (en) 1973-12-21 1978-10-30 3-CARBAMOYLOXYMETHYL-7-(.alpha.-CARBOXYMETHOXYIMINO-.alpha.(FUR-2-YL)ACETAMIDO)CEPH-3-EM-4-CARBOXYLIC ACID
AT51179A ATA51179A (en) 1973-12-21 1979-01-24 METHOD FOR PRODUCING NEW CEPHALOS PORINANTIBIOTICS
AT51279A ATA51279A (en) 1973-12-21 1979-01-24 METHOD FOR PRODUCING NEW CEPHALOS PORINANTIBIOTICS
AT13680A AT367061B (en) 1973-12-21 1980-01-11 METHOD FOR PRODUCING NEW ANTIBIOTIC COMPOUNDS
CH449880A CH626370A5 (en) 1973-12-21 1980-06-11 Process for the preparation of the syn isomer or of a mixture of syn and anti isomers of 7beta-acylamidoceph-3-em-4-carboxylic acids with antibiotic activity
JP13056680A JPS5655392A (en) 1973-12-21 1980-09-18 Manufacture of antibiotic compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB59517/73A GB1496757A (en) 1973-12-21 1973-12-21 Cephalosporin derivatives

Publications (1)

Publication Number Publication Date
GB1496757A true GB1496757A (en) 1978-01-05

Family

ID=10483908

Family Applications (1)

Application Number Title Priority Date Filing Date
GB59517/73A Expired GB1496757A (en) 1973-12-21 1973-12-21 Cephalosporin derivatives

Country Status (8)

Country Link
JP (1) JPS5655392A (en)
BE (1) BE823651A (en)
CA (1) CA1059991A (en)
CH (1) CH626370A5 (en)
FR (1) FR2355849A1 (en)
GB (1) GB1496757A (en)
PH (1) PH11646A (en)
ZA (1) ZA748146B (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0007633A2 (en) * 1978-07-31 1980-02-06 Fujisawa Pharmaceutical Co., Ltd. Cephem compounds, processes for their preparation and pharmaceutical compositions containing them
FR2439786A1 (en) * 1978-10-27 1980-05-23 Glaxo Group Ltd NOVEL CEPHALOSPORINS, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATIONS
US4258041A (en) 1978-05-26 1981-03-24 Glaxo Group Limited (6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-pyridiniummethyl)-ceph-3-em-4-carboxylate and salts thereof
US4464368A (en) * 1978-11-15 1984-08-07 Glaxo Group Limited Cephalosporin antibiotics
US5017569A (en) * 1986-11-12 1991-05-21 Ici Pharma Cephalosporin derivatives
US5057511A (en) * 1986-12-23 1991-10-15 Ici Pharma 3-heterocyclic thiomethyl cephalosporins
US5412093A (en) * 1986-12-23 1995-05-02 Ici Pharma 3-heterocyclic thiomethyl cephalosporins
US7211366B2 (en) 2003-02-21 2007-05-01 Az Electronic Materials Usa Corp. Photoresist composition for deep ultraviolet lithography
US10047066B2 (en) 2007-11-30 2018-08-14 Newlink Genetics Corporation IDO inhibitors

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO760358L (en) * 1975-02-04 1976-08-05 Fujisawa Pharmaceutical Co

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4258041A (en) 1978-05-26 1981-03-24 Glaxo Group Limited (6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-pyridiniummethyl)-ceph-3-em-4-carboxylate and salts thereof
US4600772A (en) * 1978-05-26 1986-07-15 Glaxo Group Limited Cephalosporin antibiotics
EP0007633A2 (en) * 1978-07-31 1980-02-06 Fujisawa Pharmaceutical Co., Ltd. Cephem compounds, processes for their preparation and pharmaceutical compositions containing them
EP0007633A3 (en) * 1978-07-31 1980-06-25 Fujisawa Pharmaceutical Co. Ltd. Cephem compounds, processes for their preparation, pharmaceutical compositions containing them, their starting derivatives and their preparation
FR2439786A1 (en) * 1978-10-27 1980-05-23 Glaxo Group Ltd NOVEL CEPHALOSPORINS, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATIONS
US4464368A (en) * 1978-11-15 1984-08-07 Glaxo Group Limited Cephalosporin antibiotics
US5017569A (en) * 1986-11-12 1991-05-21 Ici Pharma Cephalosporin derivatives
US5057511A (en) * 1986-12-23 1991-10-15 Ici Pharma 3-heterocyclic thiomethyl cephalosporins
US5412093A (en) * 1986-12-23 1995-05-02 Ici Pharma 3-heterocyclic thiomethyl cephalosporins
US7211366B2 (en) 2003-02-21 2007-05-01 Az Electronic Materials Usa Corp. Photoresist composition for deep ultraviolet lithography
US10047066B2 (en) 2007-11-30 2018-08-14 Newlink Genetics Corporation IDO inhibitors

Also Published As

Publication number Publication date
JPS5655392A (en) 1981-05-15
ZA748146B (en) 1976-01-28
FR2355849B1 (en) 1980-10-17
CA1059991A (en) 1979-08-07
PH11646A (en) 1978-05-08
BE823651A (en) 1975-06-20
CH626370A5 (en) 1981-11-13
FR2355849A1 (en) 1978-01-20

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Legal Events

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