FR2388814A1 - 9-Amino-de:oxy-clavulanic acid and acylated derivs. - antibacterials and beta-lactamase inhibitors - Google Patents

9-Amino-de:oxy-clavulanic acid and acylated derivs. - antibacterials and beta-lactamase inhibitors

Info

Publication number
FR2388814A1
FR2388814A1 FR7812329A FR7812329A FR2388814A1 FR 2388814 A1 FR2388814 A1 FR 2388814A1 FR 7812329 A FR7812329 A FR 7812329A FR 7812329 A FR7812329 A FR 7812329A FR 2388814 A1 FR2388814 A1 FR 2388814A1
Authority
FR
France
Prior art keywords
cor8
clavulanic acid
cor4
esp
antibacterials
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.)
Withdrawn
Application number
FR7812329A
Other languages
French (fr)
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.)
Beecham Group PLC
Original Assignee
Beecham Group PLC
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 GB17660/77A external-priority patent/GB1603208A/en
Application filed by Beecham Group PLC filed Critical Beecham Group PLC
Publication of FR2388814A1 publication Critical patent/FR2388814A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Clavulanic acid derivs. of formula (I) are new: A is H, salt forming cation or ester gp. R1 is H, CO2R3, COR4 or OR5, R2 is H, CO2R7 or COR8. R3, R4, R7 and R8 are lower alkyl or alkenyl, lower alkylaryl or aryl, R5 is CO2R6, COR6 or SO2R6, R6 is as R3. When R1 is COR4 and R2 is COR8, R4+R8 can combine so that N(COR4)COR8 is a 5-7 membered heterocycle opt. condensed to a benzene ring which can be substd. by 1 or 2, lower alkyl or alkoxy, F or Cl. Also, when R1 is OR5 and R2 is COR8, R5+R8 can combine so that N(OR5)COR8 is a 5-7 membered heterocycle. They are made by reacting a clavulanic acid ester with HNR1'R2' (R1' and R2' as R1 and R2 but not H), R14OCO.N=N.COOR15 (R14 and R15 = alkyl, alkaryl or aryl) and e.g. a trialkyl phosphite. (I) are antibacterials and inhibitors of beta-lactamase produced by Gram positive and negative bacteria. They can be used alone or esp. combined with another cephalosporin or penicillin (specifically amoxycillin or ampicillin) at ratio (I) other antibiotic of 3:1-1:10 esp. 1:1-1:8. They are esp. useful for treating infections of the respiratory and urinary tracts, or of the soft tissues, and for treating mastitis in cattle.
FR7812329A 1977-04-27 1978-04-26 9-Amino-de:oxy-clavulanic acid and acylated derivs. - antibacterials and beta-lactamase inhibitors Withdrawn FR2388814A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB17660/77A GB1603208A (en) 1977-04-27 1977-04-27 Aminodeoxyclavulanic acid and acyl derivatives threreof
GB3283577 1977-08-05
GB4793477 1977-11-15

Publications (1)

Publication Number Publication Date
FR2388814A1 true FR2388814A1 (en) 1978-11-24

Family

ID=27257530

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7812329A Withdrawn FR2388814A1 (en) 1977-04-27 1978-04-26 9-Amino-de:oxy-clavulanic acid and acylated derivs. - antibacterials and beta-lactamase inhibitors

Country Status (1)

Country Link
FR (1) FR2388814A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997010247A1 (en) * 1995-09-15 1997-03-20 Smithkline Beecham P.L.C. Clavulanic acid derivatives for treating atherosclerosis

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2353556A1 (en) * 1976-06-04 1977-12-30 Glaxo Lab Ltd CLAVULANIC ACID DERIVATIVES, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTIC APPLICATION
US4078067A (en) * 1976-04-12 1978-03-07 Merck & Co., Inc. 3-(.beta.-Aminoethylidene)-7-oxo-4-oxaazabicyclo[3.2.0]heptane-2-carboxylic acid and derivatives thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4078067A (en) * 1976-04-12 1978-03-07 Merck & Co., Inc. 3-(.beta.-Aminoethylidene)-7-oxo-4-oxaazabicyclo[3.2.0]heptane-2-carboxylic acid and derivatives thereof
FR2353556A1 (en) * 1976-06-04 1977-12-30 Glaxo Lab Ltd CLAVULANIC ACID DERIVATIVES, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTIC APPLICATION

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997010247A1 (en) * 1995-09-15 1997-03-20 Smithkline Beecham P.L.C. Clavulanic acid derivatives for treating atherosclerosis

Similar Documents

Publication Publication Date Title
GB2000138A (en) Therapeutic agents
ES452361A1 (en) Process for manufacture of 9-amino-9-deoxyclavulanates
ES476856A1 (en) Penicillins, per se and for use as antibacterially active antibiotics and their production.
FR2388814A1 (en) 9-Amino-de:oxy-clavulanic acid and acylated derivs. - antibacterials and beta-lactamase inhibitors
IT1156890B (en) 9-Amino-de:oxy-clavulanic acid and acylated derivs. - antibacterials and beta-lactamase inhibitors
NL7807413A (en) 9-Amino-de:oxy-clavulanic acid and acylated derivs. - antibacterials and beta-lactamase inhibitors
SE7713901L (en) TIOOXIMCEPHALOSPORIN AND PENICILLIN DERIVATIVES
ES442217A1 (en) 1,4-Dihydro-4-oxo-pyridylacetamido cephalosporins and their utilization as medicinal agents for combating bacterial infections
ES461691A1 (en) Beta-lactam antibiotics
ES469182A1 (en) Antibacterial agents
GB1390754A (en) Penicillin and cephalosporin esters
FR2285134A1 (en) 7-(2-(4-hydroxy-3-nitrophenyl)-2-aminoacetamido)-cephalosporins - with broad-spectrum antibacterial activity
NL7601632A (en) Antibacterial 1,8-naphthyridine derivs - viz. 7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acids, by ylid hydrolysis
FR2336130A1 (en) Antibacterial deoxy-clavulanic and isodeoxy-clavulanic acids - antibacterials used in treating urinary tract infections respiratory, illness, non-muscular tissue infections etc.
FR2372630A1 (en) Antibacterial cephalosporin type cpds - eg 7-beta-(substd-acetamido)-3-(3-heterocyclyl prop-1-enyl)-ceph-3-em-4-carboxylic acids
ES476259A1 (en) Penicillanic acid derivatives, processes for their preparation and pharmaceutical compositions containing them.
FR2429221A1 (en) 3-Carbamoyloxy:methyl cephalosporin antibiotics prodn. - from 3-hydroxymethyl cpd. and di:halo-phosphinyl isocyanate, and new intermediates
GB1074331A (en) Penicillins
GB1476432A (en) Pharmaceutical compositions containing penicillin salts
FR2264019A1 (en) Penicillins and cephalosporins prepn. - from amino penicillanic acids or cephemes and a mixed anhydride and hydrolysing
ES441744A1 (en) Cephalosporin derivatives, and compositions containing them
GB1477672A (en) Penicillin compositions
GB1476312A (en) Penicillins and cephalosporins
FR2375240A1 (en) 1,2,4-Thiazolidine 1,1-di:oxide penicillin and cephalosporin derivs. - with antibacterial and growth-promoting activity
ES452779A1 (en) 7-(alpha-(2-oxo-imidazolidin-1-yl-carbonylamino)-phenylacetamido)-cephalosporins processes for their preparation and their use as medicaments

Legal Events

Date Code Title Description
ST Notification of lapse