ES399267A1 - Antibiotics - Google Patents

Antibiotics

Info

Publication number
ES399267A1
ES399267A1 ES399267A ES399267A ES399267A1 ES 399267 A1 ES399267 A1 ES 399267A1 ES 399267 A ES399267 A ES 399267A ES 399267 A ES399267 A ES 399267A ES 399267 A1 ES399267 A1 ES 399267A1
Authority
ES
Spain
Prior art keywords
group
formula
compound
acid
see formula
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
ES399267A
Other languages
Spanish (es)
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 claimed from KR7200155A external-priority patent/KR790000084B1/en
Publication of ES399267A1 publication Critical patent/ES399267A1/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/02—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by halogen atoms
    • 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

Abstract

A procedure for the preparation of cephalosporin compounds of the formula <br/> <br/> ** (See formula) ** <br/> <br/> (where R is a hydrogen atom or an organic group, Ra is hydrogen or an acyl group, B is > S or > S > 0, and Z is a group in which 1 or 2 carbon atoms bond the core sulfur atom and the carbon atom that carries the carboxyl group) and derivatives thereof, which comprises condensing a compound of the formula <br/> <br/> ** (See formula) ** <br/> <br/> (where B and Z have the meanings defined above and R1 is hydrogen or a carboxyl blocking group) with an acylating agent corresponding to acid <br/> <br/> ** (See formula) ** <br/> <br/> (where R and Ra have the meanings defined above) or with an acylating agent corresponding to an acid that is a precursor of acid (VI) and converting the resulting precursor acyl group to the desired acyl group, after which, if necessary or if desired in each case, is carried out when Any of the following reactions: <br/> <br/> (i) conversion of a precursor from the group <br/> <br/> (see formula) desired in said group, (ii) conversion of an Δ2 isomer at the desired Δ3 isomer, (iii) removal of any carboxyl blocking groups, (iv) reduction of a compound where Z is > S → 0 to form the desired compound Z = S, and (v) recovery of the desired compound of formula (i) in the form without or anti or as a mixture containing 75% of one of such isomers.
ES399267A 1971-01-29 1972-01-28 Antibiotics Expired ES399267A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB353171A GB1389194A (en) 1971-01-29 1971-01-29 Antibiotics
GB4588571 1971-10-01
KR7200155A KR790000084B1 (en) 1971-01-29 1972-02-03 Process for preparation of antibiotics of cephalosphorin and penicillin series

Publications (1)

Publication Number Publication Date
ES399267A1 true ES399267A1 (en) 1975-06-16

Family

ID=27254286

Family Applications (2)

Application Number Title Priority Date Filing Date
ES399267A Expired ES399267A1 (en) 1971-01-29 1972-01-28 Antibiotics
ES427859A Expired ES427859A1 (en) 1971-01-29 1974-07-01 Antibiotics

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES427859A Expired ES427859A1 (en) 1971-01-29 1974-07-01 Antibiotics

Country Status (9)

Country Link
AT (2) AT326814B (en)
AU (1) AU474062B2 (en)
BE (2) BE778631A (en)
CH (2) CH598261A5 (en)
DE (3) DE2204060A1 (en)
ES (2) ES399267A1 (en)
FR (1) FR2123544B1 (en)
GB (1) GB1389194A (en)
NL (2) NL7201156A (en)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4064346A (en) * 1971-05-14 1977-12-20 Glaxo Laboratories Limited 3-Acetoxymethyl-7β-(2-carboxy-methoxyimino-2-arylacetamido)ceph-3-em-4-carboxylic acids and salts thereof
GB1443950A (en) * 1972-10-25 1976-07-28 Glaxo Lab Ltd Acylamido-penam-carboxylic acids and their derivatives
US4033950A (en) * 1971-05-14 1977-07-05 Glaxo Laboratories Limited 3-Hydroxymethyl-7β-(2-alkoxy-or benzyloxyimino-2-arylacetamido)ceph-3-em-4-carboxylic acids and salts thereof
US4079178A (en) * 1971-05-14 1978-03-14 Glaxo Laboratories Limited Cephalosporins having (α-etherified oximino) acylamido groups at the 7-position
GB1447114A (en) * 1973-02-20 1976-08-25 Glaxo Lab Ltd Process for the preparation of 2-aryl-2-hydroxyiminoacetic acid
GB1472534A (en) * 1973-07-06 1977-05-04 Glaxo Lab Ltd 7beta-hydroxyiminoacylamido-cephalosporins
US4144393A (en) 1973-12-21 1979-03-13 Glaxo Laboratories Limited 3-Acetoxymethyl cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyiminoarylacetamido group
US4144392A (en) 1973-12-21 1979-03-13 Glaxo Laboratories Limited Cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyimino-arylacetamido group and at position-3 the residue of a sulphur nucleophile
US4020058A (en) * 1974-10-03 1977-04-26 Glaxo Laboratories Limited Improvements in or relating to cephalosporin antibiotics
US4200746A (en) 1974-12-20 1980-04-29 Glaxo Laboratories, Ltd. Cephalosporins
FI66005C (en) * 1975-02-04 1984-08-10 Fujisawa Pharmaceutical Co FRUIT PROTECTION FOR ANTIBACTERIAL VERIFICATION OF 7-ALPHA ALPHA-DISUBSTITUTE-ACETAMIDO) -3-SUBSTITUTER-3-CEFE M - CARBOXYL SYRINE SYN-ISOMER
GB1555471A (en) * 1975-06-19 1979-11-14 Glaxo Lab Ltd 7 carbamoylalkoxyimino acetamido 3 em 4 carboxylic acidsand derivatives thereof
US4165430A (en) 1976-03-19 1979-08-21 Glaxo Laboratories Limited Cephalosporins having a 7-carboxy substituted α-etherified oximinoarylacetamido) group
US4166115A (en) * 1976-04-12 1979-08-28 Fujisawa Pharmaceutical Co., Ltd. Syn 7-oxoimino substituted derivatives of cephalosporanic acid
FR2384779A1 (en) * 1977-03-25 1978-10-20 Roussel Uclaf NEW OXIMES DERIVED FROM 3-CHLORO OR 3-METHOXY 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICINAL PRODUCTS
DE2716677C2 (en) 1977-04-15 1985-10-10 Hoechst Ag, 6230 Frankfurt Cephem derivatives and processes for their preparation
DE2714880A1 (en) * 1977-04-02 1978-10-26 Hoechst Ag CEPHEMDER DERIVATIVES AND PROCESS FOR THEIR PRODUCTION
FR2418233A2 (en) * 1978-02-22 1979-09-21 Roussel Uclaf Antibiotic syn isomers of oxime(s) - of 3-alkylthio or acylamino 7-amino thiazolyl acetamido cephalosporanic acids
US4409214A (en) 1979-11-19 1983-10-11 Fujisawa Pharmaceutical, Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof
US4409215A (en) * 1979-11-19 1983-10-11 Fujisawa Pharmaceutical Co., Ltd. 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof
IL63207A (en) * 1980-07-24 1985-09-29 Lonza Ag Process for the preparation of 2-(2-aminothiazole-4-yl)-2-(syn)-methoxyiminoacetic acid esters
US4443374A (en) * 1982-02-01 1984-04-17 E. R. Squibb & Sons, Inc. Process for preparing (3S)-3-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]-acetyl]amino]-2-oxo-1-azetidinesulfonic acid, and 4-substituted derivatives
EP0201999A1 (en) * 1985-04-16 1986-11-20 Imperial Chemical Industries Plc Substituted 2-cyano-2-oximino-acetamides, processes for their production and their use as fungicides
GB8927871D0 (en) * 1989-12-08 1990-02-14 Beecham Group Plc Novel compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1159449B (en) * 1961-03-22 1963-12-19 Gruenenthal Chemie Process for the preparation of 6-acylaminopenicillanic acids and their salts
SE311519B (en) * 1962-12-14 1969-06-16 Astra Ab
GB1208014A (en) * 1967-03-23 1970-10-07 Glaxo Lab Ltd Cephalosporins
GB1208015A (en) * 1967-03-23 1970-10-07 Glaxo Lab Ltd Cephalosporins

Also Published As

Publication number Publication date
BE778631A (en) 1972-07-28
AT326814B (en) 1975-12-29
FR2123544B1 (en) 1975-10-10
DE2204108A1 (en) 1972-08-24
AU3845072A (en) 1973-08-02
AU474062B2 (en) 1976-07-15
NL7201157A (en) 1972-08-01
FR2123544A1 (en) 1972-09-08
CH598261A5 (en) 1978-04-28
DE2204060A1 (en) 1972-08-10
ATA70272A (en) 1975-04-15
CH621790A5 (en) 1981-02-27
BE778630A (en) 1972-07-28
GB1389194A (en) 1975-04-03
DE2264676A1 (en) 1974-08-08
ES427859A1 (en) 1976-08-01
ATA70172A (en) 1975-03-15
AT327375B (en) 1976-01-26
NL7201156A (en) 1972-08-01

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