GB1364453A - Penicillanic and cepholosporanic acid derivatives - Google Patents

Penicillanic and cepholosporanic acid derivatives

Info

Publication number
GB1364453A
GB1364453A GB5304070A GB5304070A GB1364453A GB 1364453 A GB1364453 A GB 1364453A GB 5304070 A GB5304070 A GB 5304070A GB 5304070 A GB5304070 A GB 5304070A GB 1364453 A GB1364453 A GB 1364453A
Authority
GB
United Kingdom
Prior art keywords
group
formula
lower alkyl
compounds
acid
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
GB5304070A
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.)
Gist Brocades NV
Original Assignee
Gist Brocades NV
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 Gist Brocades NV filed Critical Gist Brocades NV
Priority to GB5304070A priority Critical patent/GB1364453A/en
Priority to US195482A priority patent/US3891635A/en
Priority to ES396720A priority patent/ES396720A1/en
Priority to DE2155081A priority patent/DE2155081B2/en
Priority to AU35431/71A priority patent/AU463230B2/en
Priority to BE775012A priority patent/BE775012A/en
Priority to DE19712166468 priority patent/DE2166468A1/en
Priority to CA126,985A priority patent/CA983920A/en
Priority to CH1616271A priority patent/CH573436A5/xx
Priority to JP46088177A priority patent/JPS5212200B1/ja
Priority to HUKO2471A priority patent/HU162822B/hu
Priority to NL717115231A priority patent/NL150117B/en
Priority to CH1400375A priority patent/CH572936A5/xx
Priority to DE19712166467 priority patent/DE2166467A1/en
Priority to SU1713952A priority patent/SU520050A3/en
Priority to FR7139822A priority patent/FR2112504B1/fr
Priority to CH1400275A priority patent/CH572935A5/xx
Priority to ZA717433A priority patent/ZA717433B/en
Priority to CA166,365A priority patent/CA993442A/en
Priority to ES423795A priority patent/ES423795A1/en
Publication of GB1364453A publication Critical patent/GB1364453A/en
Priority to US05/533,708 priority patent/US4010264A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D261/00Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D499/00Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1364453 Penicillins and cephalosporins GIST-BROCADES NV 5 Nov 1971 [6 Nov 1970] 53040/70 Heading C2A The invention comprises penicillanic and cephalosporanic acid derivatives of the general Formula I in which Q represents the Group II or the Group III (wherein X represents a hydrogen atom, a hydroxy group, or a lower alkanoyloxy group, or the grouping -CH 2 X and the carboxy group in Formula III are linked together to form a lactone or lactam group, R represents a lower alkyl or an adamantyl group, or an aryl group optionally carrying one or more substituents selected from chlorine and fluorine atoms, and nitro, amino and lower alkyl groups, R<SP>1</SP> represents a hydrogen or a chlorine atom, a lower alkyl group, a carbamoyl, cyano or amino group, or a carboxy group optionally esterified with a lower alkyl group or transformed into an alkali metal, alkaline earth metal or amine salt, and R<SP>2</SP> represents a hydrogen or halogen atom, a cyano or amino group, a phenyl (lower) alkoxycarbonylamino group optionally substituted on the phenyl ring, or R<SP>2</SP> represents a lower alkyl group, a carboxy group esterified with a lower alkyl or benzyl group, or a carbamoyl group optionally carrying on the nitrogen atom a lower alkyl or phenyl substituent) and alkali metal, alkaline earth metal and amine salts, esters and amides of the compounds of Formula I. The compounds of Formula I may be prepared by reacting a salt, ester or amide of a compound of Formula IV or of Formula V wherein the substituent X, if a hydroxy group is preferably protected with a 2,4-dinitrophenyl ester, p-nitrophenyl ester or N-hydroxysuccinimide ester group, with an acid of general Formula VI or an acylating derivative thereof. A further method for the preparation of compounds of Formula I comprises reacting an acid of general Formula VI in which the reactive groups R, R<SP>1</SP> and R<SP>2</SP> are suitably protected, with a 6-isocyanatopenicillanic acid or 7 - isocyanatocephalosporanic acid of formula O = C = N-Q in which carboxy and hydroxy groups if present are protected, e.g. by di- or tri-alkylsilyl group. A still further method of preparation of compounds of general Formula I comprises reacting the above isocyanato compounds with organometal compounds of formula A-Me<SP>I</SP>, A-Me<SP>II</SP>-Hal or A-Me<SP>11</SP>-A in which Me represents a metal atom whose valency is indicated by the numeral I or II. Therapeutic compositions comprise an effective amount of a penicillanic or cephalosporanic acid compound of Formula I in conjunction with a pharmaceutically acceptable carrier or excipient.
GB5304070A 1970-11-06 1970-11-06 Penicillanic and cepholosporanic acid derivatives Expired GB1364453A (en)

Priority Applications (21)

Application Number Priority Date Filing Date Title
GB5304070A GB1364453A (en) 1970-11-06 1970-11-06 Penicillanic and cepholosporanic acid derivatives
US195482A US3891635A (en) 1970-11-06 1971-11-03 7-{8 3-(Phenyl)-isoxazol-5-yl{9 acetamido-cephalosporanic acids
NL717115231A NL150117B (en) 1970-11-06 1971-11-05 PROCESS FOR THE PREPARATION OF 6-ACYLAMINOPENICILLAN ACID AND 7-ACYLAMINOCEPHALOSSPORANIC ACID DERIVATIVES AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE PENICILLINS AND / OR CEPHALOSPORINS.
DE19712166467 DE2166467A1 (en) 1970-11-06 1971-11-05 NEW PENICILLANIC ACID DERIVATIVES, THEIR MANUFACTURING PROCESS AND THE PHARMACEUTICAL COMPOSITIONS THEREOF
AU35431/71A AU463230B2 (en) 1970-11-06 1971-11-05 Penicillanic and cephalosporanic acid derivatives
BE775012A BE775012A (en) 1970-11-06 1971-11-05 NEW HETEROCYCLIC COMPOUNDS
DE19712166468 DE2166468A1 (en) 1970-11-06 1971-11-05 NEW ISOXAZOLYL DERIVATIVES AND PROCESS FOR THEIR PRODUCTION
CA126,985A CA983920A (en) 1970-11-06 1971-11-05 Heterocyclic compounds
CH1616271A CH573436A5 (en) 1970-11-06 1971-11-05
JP46088177A JPS5212200B1 (en) 1970-11-06 1971-11-05
HUKO2471A HU162822B (en) 1970-11-06 1971-11-05
ES396720A ES396720A1 (en) 1970-11-06 1971-11-05 7-{8 3-(Phenyl)-isoxazol-5-yl{9 acetamido-cephalosporanic acids
CH1400375A CH572936A5 (en) 1970-11-06 1971-11-05
DE2155081A DE2155081B2 (en) 1970-11-06 1971-11-05 7- (Isoxazol-5-yl-acetamido) cephalosporanic acid derivatives, processes for their preparation and pharmaceutical compositions containing them
SU1713952A SU520050A3 (en) 1970-11-06 1971-11-05 The method of obtaining derivatives of penicillin or cephalosporin
FR7139822A FR2112504B1 (en) 1970-11-06 1971-11-05
CH1400275A CH572935A5 (en) 1970-11-06 1971-11-05
ZA717433A ZA717433B (en) 1970-11-06 1971-11-05 New penicillanic and cephalosporanic acid derivatives
CA166,365A CA993442A (en) 1970-11-06 1973-03-19 Heterocyclic compounds
ES423795A ES423795A1 (en) 1970-11-06 1974-03-01 7-{8 3-(Phenyl)-isoxazol-5-yl{9 acetamido-cephalosporanic acids
US05/533,708 US4010264A (en) 1970-11-06 1974-12-17 7-[3-Substituted isoxazol-5-yl]-acetamido-cephalosporanic acids and their anti-bacterial use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5304070A GB1364453A (en) 1970-11-06 1970-11-06 Penicillanic and cepholosporanic acid derivatives

Publications (1)

Publication Number Publication Date
GB1364453A true GB1364453A (en) 1974-08-21

Family

ID=10466394

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5304070A Expired GB1364453A (en) 1970-11-06 1970-11-06 Penicillanic and cepholosporanic acid derivatives

Country Status (14)

Country Link
US (1) US3891635A (en)
JP (1) JPS5212200B1 (en)
AU (1) AU463230B2 (en)
BE (1) BE775012A (en)
CA (1) CA983920A (en)
CH (3) CH573436A5 (en)
DE (3) DE2166468A1 (en)
ES (2) ES396720A1 (en)
FR (1) FR2112504B1 (en)
GB (1) GB1364453A (en)
HU (1) HU162822B (en)
NL (1) NL150117B (en)
SU (1) SU520050A3 (en)
ZA (1) ZA717433B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1459392A (en) * 1972-12-22 1976-12-22 Gist Brocades Nv Heterocyclic compounds
FR2219775A1 (en) * 1973-03-02 1974-09-27 Gist Brocades Nv Isoxazolylacetamido penicillanic and cephalosporanic acids - partic. active against Gram-positive bacteria
JPS5760345B2 (en) * 1974-12-19 1982-12-18 Takeda Chemical Industries Ltd
DK154939C (en) * 1974-12-19 1989-06-12 Takeda Chemical Industries Ltd METHOD OF ANALOGUE FOR THE PREPARATION OF THIAZOLYLACETAMIDO-CEPHEM COMPOUNDS OR PHARMACEUTICAL ACCEPTABLE SALTS OR ESTERS THEREOF
CA1088049A (en) * 1975-06-03 1980-10-21 Takashi Masugi 3-substituted-7-substituted alkanamido-3-cephem-4- carboxylic acid compounds and processes for preparation thereof
MD227C2 (en) * 1976-01-23 1995-11-30 Roussel Uclaf, Societe Anonyme Method of 7-(2-(2-aminothiazolyl-4)-2-oxyiminoacetamido)-3-acetoxymethyl-3-cefem-4-carbonic acid preparation in the form of sin-isomers
JPS6052713B2 (en) * 1978-04-11 1985-11-20 三共株式会社 7-Methoxycephalosporin compound, its production method, and antibacterial agent containing the compound as a main ingredient
CA1128526A (en) * 1979-10-05 1982-07-27 Cdc Life Sciences Inc. 3,4-diarylisoxazol-5-acetic acids
US4526977A (en) * 1981-10-07 1985-07-02 American Home Products Corporation 2-(3-Amino-5-isoxazolyl)-2-oxyimino-acetic acids
JPS60141367U (en) * 1984-02-29 1985-09-19 タキロン株式会社 skylight locking device
US4562187A (en) * 1985-01-22 1985-12-31 Hoechst-Roussel Pharmaceuticals Inc. (Isoxazol-3-yl)arylmethanones, compositions and pharmaceutical use
US7427680B2 (en) * 2001-01-12 2008-09-23 The Regents Of The University Of California Fluorogenic substrates for BETA-lactamase gene expression
AU2002251755C1 (en) * 2001-01-12 2008-07-10 The Regents Of The University Of California Beta-lactamase substrates having phenolic ethers

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3218318A (en) * 1962-08-31 1965-11-16 Lilly Co Eli 7-heterocyclic-substituted-acylamido cephalosporins
US3459746A (en) * 1965-10-04 1969-08-05 Lilly Co Eli 7 - heteromonocyclic-substituted acylamido derivatives of desacetyl cephalosporanic acid

Also Published As

Publication number Publication date
DE2166468A1 (en) 1974-02-14
CA983920A (en) 1976-02-17
ES423795A1 (en) 1976-12-16
FR2112504B1 (en) 1975-10-31
BE775012A (en) 1972-05-05
AU463230B2 (en) 1975-07-17
AU3543171A (en) 1973-05-10
US3891635A (en) 1975-06-24
DE2155081C3 (en) 1975-12-18
CH573436A5 (en) 1976-03-15
NL7115231A (en) 1972-05-09
ES396720A1 (en) 1975-04-16
SU520050A3 (en) 1976-06-30
HU162822B (en) 1973-04-28
FR2112504A1 (en) 1972-06-16
DE2155081B2 (en) 1975-05-15
ZA717433B (en) 1972-07-26
CH572935A5 (en) 1976-02-27
DE2155081A1 (en) 1972-05-10
DE2166467A1 (en) 1974-02-14
JPS5212200B1 (en) 1977-04-05
NL150117B (en) 1976-07-15
CH572936A5 (en) 1976-02-27

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee