GB1522140A - Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them - Google Patents

Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them

Info

Publication number
GB1522140A
GB1522140A GB55213/74A GB5521374A GB1522140A GB 1522140 A GB1522140 A GB 1522140A GB 55213/74 A GB55213/74 A GB 55213/74A GB 5521374 A GB5521374 A GB 5521374A GB 1522140 A GB1522140 A GB 1522140A
Authority
GB
United Kingdom
Prior art keywords
compounds
syn isomer
resulting
syn
group
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
GB55213/74A
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 GB55213/74A priority Critical patent/GB1522140A/en
Priority to IE2786/75A priority patent/IE42458B1/en
Priority to NZ179598A priority patent/NZ179598A/en
Priority to DK582775A priority patent/DK582775A/en
Priority to JP50150664A priority patent/JPS5191287A/ja
Priority to BE162939A priority patent/BE836872R/en
Priority to AU87744/75A priority patent/AU506951B2/en
Priority to CA242,140A priority patent/CA1074297A/en
Priority to DE19752557397 priority patent/DE2557397A1/en
Priority to SE7514475A priority patent/SE7514475L/en
Priority to NL7514847A priority patent/NL7514847A/en
Priority to CH1655375A priority patent/CH627758A5/en
Priority to FR7539200A priority patent/FR2294707A1/en
Priority to ZA757890A priority patent/ZA757890B/en
Priority to AT970175A priority patent/AT343804B/en
Priority to US05/888,242 priority patent/US4200746A/en
Publication of GB1522140A publication Critical patent/GB1522140A/en
Priority to CH396880A priority patent/CH629211A5/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
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings

Abstract

Compounds with antibiotic activity and the formula I <IMAGE> in which the symbols B, R<1>, R<2> and R<3> have the meaning stated in Claim 1, are prepared in the form of the syn isomer or a mixture of syn isomer and anti isomer, where the content of the syn isomer is at least 90%, by reacting a corresponding ceph-3-em-4-carboxylic acid which is substituted in position 3 by a group -CH2X where X is a substituent which can be replaced by the pyridine residue, where appropriate with intermediate protection of the 4-carboxyl group, with an R<3>-substituted pyridine and, if the precursor has an R<1>COCONH group in position 7, converting the resulting compound into the corresponding ceph-3-em compound I by reaction with a hydroxylamine R<2>ONH2. Resulting compounds I in which B is &rdurule& S->O can subsequently be reduced to the corresponding, preferred, compounds in which B is &rdurule& S. In another process, the resulting carboxylic acids (I) are esterified. The compounds are distinguished by an antibiotic activity with a broad spectrum of action, especially by a high activity against Gram-negative microorganisms including those which produce beta -lactamases, and furthermore have a high stability to beta -lactamases produced by some Gram-negative organisms, and to esterases.
GB55213/74A 1974-12-20 1974-12-20 Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them Expired GB1522140A (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
GB55213/74A GB1522140A (en) 1974-12-20 1974-12-20 Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them
SE7514475A SE7514475L (en) 1974-12-20 1975-12-19 CEPHALOSPORINER
NL7514847A NL7514847A (en) 1974-12-20 1975-12-19 PROCEDURE FOR THE PREPARATION OF NEW ANTIBIOTICA, PROCEDURE FOR THE PREPARATION OF PHARMACEUTICAL PREPARATIONS CONTAINING THEM, AS WELL AS FORMED PREPARATIONS OBTAINED ACCORDING TO THIS PROCESS.
DK582775A DK582775A (en) 1974-12-20 1975-12-19 CEPHALOSPORINE DERIVATIVES AND PROCEDURES
JP50150664A JPS5191287A (en) 1974-12-20 1975-12-19
BE162939A BE836872R (en) 1974-12-20 1975-12-19 ANTIFIOTICS IMPROVEMENTS
AU87744/75A AU506951B2 (en) 1974-12-20 1975-12-19 Cephalosporins
CA242,140A CA1074297A (en) 1974-12-20 1975-12-19 Cephalosporins
DE19752557397 DE2557397A1 (en) 1974-12-20 1975-12-19 CEPHALOSPORIN ANTIBIOTICS
IE2786/75A IE42458B1 (en) 1974-12-20 1975-12-19 Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl-cephalosporins, methods for their preparation and compositions containing them
NZ179598A NZ179598A (en) 1974-12-20 1975-12-19 Cephalosporins and pharmaceutical compositions
CH1655375A CH627758A5 (en) 1974-12-20 1975-12-19 Process for the preparation of the syn isomer or a mixture of the syn isomer and anti isomer of 7beta-acylamidoceph-3-em-4-carboxylic acids with the antibiotic activity
FR7539200A FR2294707A1 (en) 1974-12-20 1975-12-19 IMPROVEMENTS IN ANTIBIOTICS OF THE CEPHALOSPORIN SERIES
ZA757890A ZA757890B (en) 1974-12-20 1975-12-19 Improvements in or relating to antibiotics
AT970175A AT343804B (en) 1974-12-20 1975-12-19 METHOD FOR PRODUCING NEW CEPHALOSPORINE ANTIBIOTICS
US05/888,242 US4200746A (en) 1974-12-20 1978-03-20 Cephalosporins
CH396880A CH629211A5 (en) 1974-12-20 1980-05-16 Process for the preparation of the syn isomer or a mixture of syn isomer and anti isomer of 7beta-acylamido-ceph-3-em-4-carboxylic acids with antibiotic activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB55213/74A GB1522140A (en) 1974-12-20 1974-12-20 Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them

Publications (1)

Publication Number Publication Date
GB1522140A true GB1522140A (en) 1978-08-23

Family

ID=10473287

Family Applications (1)

Application Number Title Priority Date Filing Date
GB55213/74A Expired GB1522140A (en) 1974-12-20 1974-12-20 Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them

Country Status (15)

Country Link
JP (1) JPS5191287A (en)
AT (1) AT343804B (en)
AU (1) AU506951B2 (en)
BE (1) BE836872R (en)
CA (1) CA1074297A (en)
CH (2) CH627758A5 (en)
DE (1) DE2557397A1 (en)
DK (1) DK582775A (en)
FR (1) FR2294707A1 (en)
GB (1) GB1522140A (en)
IE (1) IE42458B1 (en)
NL (1) NL7514847A (en)
NZ (1) NZ179598A (en)
SE (1) SE7514475L (en)
ZA (1) ZA757890B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198504A (en) 1978-11-02 1980-04-15 Bristol-Myers Company [3-(Pyridinium)-7-(naphthyiridinyl carbonylamino)acetamido]cephalosporanic acid derivatives
US4369313A (en) 1979-05-25 1983-01-18 Glaxo Group Limited Intermediates for use in the preparation of cephalosporin antibiotics
US4603129A (en) * 1980-02-23 1986-07-29 Hoechst Aktiengesellschaft Cephalosporin derivatives
US5202315A (en) * 1989-05-11 1993-04-13 Lucky, Ltd. Cephalosporin compounds

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4963542A (en) * 1976-09-08 1990-10-16 Takeda Chemical Industries, Ltd. Cephalosporin derivatives
JPS5657790A (en) * 1979-10-02 1981-05-20 Glaxo Group Ltd Cephalosporin antibiotic

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

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198504A (en) 1978-11-02 1980-04-15 Bristol-Myers Company [3-(Pyridinium)-7-(naphthyiridinyl carbonylamino)acetamido]cephalosporanic acid derivatives
US4369313A (en) 1979-05-25 1983-01-18 Glaxo Group Limited Intermediates for use in the preparation of cephalosporin antibiotics
US4433141A (en) * 1979-05-25 1984-02-21 Glaxo Group Limited Intermediate for use in the preparation of cephalosporin antibiotics
US4603129A (en) * 1980-02-23 1986-07-29 Hoechst Aktiengesellschaft Cephalosporin derivatives
US5202315A (en) * 1989-05-11 1993-04-13 Lucky, Ltd. Cephalosporin compounds

Also Published As

Publication number Publication date
CH627758A5 (en) 1982-01-29
BE836872R (en) 1976-06-21
FR2294707B1 (en) 1978-09-29
SE7514475L (en) 1976-06-21
AU506951B2 (en) 1980-01-31
IE42458B1 (en) 1980-08-13
NZ179598A (en) 1978-04-03
JPS5191287A (en) 1976-08-10
AU8774475A (en) 1977-06-23
NL7514847A (en) 1976-06-22
ATA970175A (en) 1977-10-15
IE42458L (en) 1976-06-20
DE2557397A1 (en) 1976-06-24
CA1074297A (en) 1980-03-25
CH629211A5 (en) 1982-04-15
ZA757890B (en) 1976-11-24
DK582775A (en) 1976-06-21
AT343804B (en) 1978-06-26
FR2294707A1 (en) 1976-07-16

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Legal Events

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