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IE780760L - Cephalosporin antibiotics - Google Patents

Cephalosporin antibiotics

Info

Publication number
IE780760L
IE780760L IE780760A IE76078A IE780760L IE 780760 L IE780760 L IE 780760L IE 780760 A IE780760 A IE 780760A IE 76078 A IE76078 A IE 76078A IE 780760 L IE780760 L IE 780760L
Authority
IE
Ireland
Prior art keywords
lower alkyl
carboxylic acids
denotes
cephalosporin antibiotics
gb1598568a
Prior art date
Application number
IE780760A
Other versions
IE46726B1 (en
Original Assignee
Glaxo Lab 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 Lab Ltd filed Critical Glaxo Lab Ltd
Publication of IE780760L publication Critical patent/IE780760L/en
Publication of IE46726B1 publication Critical patent/IE46726B1/en

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
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
    • 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
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
    • C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (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

Cephalosporin derivatives of the formula: <IMAGE> in which R<1> denotes lower alkyl and R<2> denotes hydrogen or lower alkyl. In contrast to the free carboxylic acids, these novel esters are very well absorbed by the gastrointestinal tract and then hydrolyse rapidly to give corresponding carboxylic acids having a broad spectrum antibiotic action. They are prepared by esterification of the carboxyl group in the 4-position, by N-acylation of the 7-aminocephemcarboxylic acid ester or by carbamoylation of the hydroxymethyl group in the 3-position. [GB1598568A]
IE760/78A 1977-04-19 1978-04-18 Esters of (6r,7r)-3-carbamoyloxymethyl-7-((z)-2-(fur-2-yl)-methoxyiminoacetamido)-ceph-3-em-4-carboxylic acid IE46726B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB16202/77A GB1598568A (en) 1977-04-19 1977-04-19 Esters of(6r,7r)-3-carbamoyloxymethyl-7-((z)-2-(fur-2-yl)-2-methoxyiminoacetamido)-ceph-3-em-4-carboxylic acid

Publications (2)

Publication Number Publication Date
IE780760L true IE780760L (en) 1978-10-19
IE46726B1 IE46726B1 (en) 1983-09-07

Family

ID=10073017

Family Applications (1)

Application Number Title Priority Date Filing Date
IE760/78A IE46726B1 (en) 1977-04-19 1978-04-18 Esters of (6r,7r)-3-carbamoyloxymethyl-7-((z)-2-(fur-2-yl)-methoxyiminoacetamido)-ceph-3-em-4-carboxylic acid

Country Status (20)

Country Link
JP (1) JPS53132592A (en)
KR (1) KR840000081B1 (en)
AT (1) AT363183B (en)
AU (1) AU521098B2 (en)
BE (1) BE866093A (en)
CA (1) CA1093068A (en)
CH (1) CH639096A5 (en)
DE (1) DE2816873A1 (en)
DK (1) DK147513C (en)
ES (1) ES468895A1 (en)
FR (1) FR2387988A1 (en)
GB (1) GB1598568A (en)
IE (1) IE46726B1 (en)
IL (1) IL54531A (en)
IT (1) IT1104842B (en)
NL (1) NL7804097A (en)
NZ (1) NZ186998A (en)
SE (1) SE433748B (en)
YU (1) YU90978A (en)
ZA (1) ZA782211B (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2482587A1 (en) * 1980-05-14 1981-11-20 Poudres & Explosifs Ste Nale PROCESS FOR THE SYNTHESIS OF A-CHLORINATED CHLOROFORMIATES AND NEW A-CHLORINATED CHLOROFORMIATES
AU8166182A (en) * 1981-03-23 1982-09-30 Kyoto Yakuhin Kogyo K.K. Cephalosporin derivatives
FR2532933B1 (en) * 1982-06-29 1987-11-13 Astra Laekemedel Ab IMPROVEMENTS IN THE PREPARATION OF ANTIBIOTICS
IT1190897B (en) * 1982-06-29 1988-02-24 Opos Biochimica Srl PROCEDURE FOR THE PREPARATION OF THE 1-ETHOXYCARBONYLOXYETHYL ACID ACID 6- (D (-) - ALPHA AMINOALPHA-PHENYLACETAMIDE) -PENICILLANIC
GB2123821B (en) * 1982-06-29 1987-04-23 Astra Laekemedel Ab At-halogeno diethyl carbonates and their use in the preparation of antibiotics
IL68992A (en) * 1982-06-29 1991-06-10 Astra Laekemedel Ab Alpha-bromo diethyl carbonate and process for the preparation of ethoxycarbonyloxy esters of penicillanic acids
YU44680B (en) * 1982-07-30 1990-12-31 Glaxo Lab Ltd Process for obtaining very pure amorphous form of cephuroxim axetile
US4606865A (en) * 1982-09-20 1986-08-19 Astra Lakemedel Aktiebolag Methods for the preparation of α-bromodiethylcarbonate
IL67623A (en) * 1983-01-05 1984-09-30 Teva Pharma 1'-ethoxycarbonyloxyethyl ester of valproic acid,its preparation and pharmaceutical compositions containing it
GB8320521D0 (en) * 1983-07-29 1983-09-01 Glaxo Group Ltd Chemical process
FR2551058B1 (en) * 1983-08-26 1986-09-26 Poudres & Explosifs Ste Nale PROCESS FOR THE PREPARATION OF A-CHLORINATED CHLOROFORMIATES
GB8400024D0 (en) * 1984-01-03 1984-02-08 Glaxo Group Ltd Cephalosporin antibiotics
US4612143A (en) * 1984-09-17 1986-09-16 Societe Nationale Des Poudres Et Explosifs Process for the preparation of fluoroformates
US5202454A (en) * 1986-07-11 1993-04-13 Societe Nationale Des Poudres Et Explosifs Process for the manufacture of 1-bromoalkyl hydrocarbyl carbonates
KR100342944B1 (en) 1999-11-08 2002-07-02 민경윤 Method for preparing highly pure cefpodoxime proxetil
GB0301938D0 (en) * 2003-01-28 2003-02-26 Biochemie Gmbh Organic compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1453049A (en) * 1973-08-21 1976-10-20 Glaxo Lab Ltd Cephalosporing antibiotics
CA1094545A (en) * 1976-02-16 1981-01-27 Michael Gregson Cephalosporin antibiotics
CA1093549A (en) * 1976-02-16 1981-01-13 Michael Gregson Cephalosporin antibiotics

Also Published As

Publication number Publication date
IL54531A (en) 1981-07-31
NZ186998A (en) 1981-05-01
NL7804097A (en) 1978-10-23
DK168778A (en) 1978-10-20
AU3518778A (en) 1979-10-25
SE7804400L (en) 1978-10-20
KR840000081B1 (en) 1984-02-08
DK147513B (en) 1984-09-10
ZA782211B (en) 1979-04-25
YU90978A (en) 1983-01-21
IT1104842B (en) 1985-10-28
JPS53132592A (en) 1978-11-18
DK147513C (en) 1985-03-18
CA1093068A (en) 1981-01-06
AT363183B (en) 1981-07-10
BE866093A (en) 1978-10-18
FR2387988B1 (en) 1982-06-11
FR2387988A1 (en) 1978-11-17
DE2816873A1 (en) 1978-11-02
CH639096A5 (en) 1983-10-31
IL54531A0 (en) 1978-07-31
AU521098B2 (en) 1982-03-18
GB1598568A (en) 1981-09-23
IT7848941A0 (en) 1978-04-18
ES468895A1 (en) 1978-12-01
ATA274878A (en) 1980-12-15
IE46726B1 (en) 1983-09-07
KR830000246A (en) 1983-03-30
SE433748B (en) 1984-06-12

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