GB1427211A - P-hydroxymethylphenylacetamido-cephalosporins - Google Patents

P-hydroxymethylphenylacetamido-cephalosporins

Info

Publication number
GB1427211A
GB1427211A GB2779573A GB2779573A GB1427211A GB 1427211 A GB1427211 A GB 1427211A GB 2779573 A GB2779573 A GB 2779573A GB 2779573 A GB2779573 A GB 2779573A GB 1427211 A GB1427211 A GB 1427211A
Authority
GB
United Kingdom
Prior art keywords
amino
hydroxymethylphenylacetamido
ylthiomethyl
cephem
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
GB2779573A
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.)
GlaxoSmithKline LLC
Original Assignee
SmithKline Corp
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 US262903A external-priority patent/US3867380A/en
Priority claimed from US00289499A external-priority patent/US3855213A/en
Priority claimed from US359566A external-priority patent/US3891634A/en
Application filed by SmithKline Corp filed Critical SmithKline Corp
Publication of GB1427211A publication Critical patent/GB1427211A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545—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, cefaclor, or cephalexine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • 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
    • C07D501/36—Methylene radicals, substituted by sulfur atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

1427211 Cephalosporins SMITHKLINE CORP 12 June 1973 [14 June 1972 15 Sept 1972 11 May 1973] 27795/73 Heading C2C Novel cephalosporins, having antibacterial activity, of Formula I wherein A is hydrogen, acetoxy, methoxy, methylthio or monocyclic heterocyclic thio, and pharmaceutically acceptable salts thereof, are prepared by acylating a compound of formula wherein A is as defined above, with p-hydroxymethylphenylglycine or an activated derivative thereof, the amino group being protected with a removable protecting group. Following acylation, the protective groups may be removed with trifluoroacetic acid and the resulting salt may be converted to the zwitterionic compound by means of basic ion exchange resin. The preparation of 7-(α-amino-p-hydroxymethylphenylacetamido) cephalosporanic acid, 7-(α- amino - p - hydroxymethylphenylacetamido)- 3 - desacetoxy cephalosporanic acid, 7 - (α- amino - p - hydroxymethyl - phenylacetamido)- 3 - (1 - methyl - 1,2,3,4 - tetrazol - 5 - ylthiomethyl) - 3 - cephem - 4 - carboxylic acid, 7- (α - amino - p - hydroxymethylphenylacetamido) - 3 - (1,2,3 - triazol - 5 - ylthiomethyl)- 3 - cephem - 4 - carboxylic acid and 7 - (α- amino - p - hydroxymethylphenylacetamido)- 3 - (5 - methyl - 1,3,4 - thiadiazol - 2 - ylthiomethyl) - 3 - cephem - 4 - carboxylic acid is described in the examples. Antibacterial compositions, suitable for injection or oral administration, comprise a compound of Formula I and a pharmaceutically acceptable carrier.
GB2779573A 1972-06-14 1973-06-12 P-hydroxymethylphenylacetamido-cephalosporins Expired GB1427211A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US262903A US3867380A (en) 1971-02-18 1972-06-14 3-Heterocyclic thiomethylcephalosporins
US00289499A US3855213A (en) 1971-02-18 1972-09-15 3-heterocyclic thiomethyl-cephalosporins
US359566A US3891634A (en) 1970-12-17 1973-05-11 P-Hydroxymethylphenylacetamidocephalosporins

Publications (1)

Publication Number Publication Date
GB1427211A true GB1427211A (en) 1976-03-10

Family

ID=27401551

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2779573A Expired GB1427211A (en) 1972-06-14 1973-06-12 P-hydroxymethylphenylacetamido-cephalosporins

Country Status (6)

Country Link
JP (1) JPS4949983A (en)
AU (1) AU470357B2 (en)
CA (1) CA1003405A (en)
DE (1) DE2330296A1 (en)
FR (1) FR2187306B1 (en)
GB (1) GB1427211A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1074784A (en) * 1974-09-06 1980-04-01 Sumitomo Chemical Company N-ACYLAMINO-.alpha.-ARYLACETAMIDO CEPHALOSPORINS
JPH01157988A (en) * 1987-12-12 1989-06-21 Microbial Chem Res Found Oral cephalosporin derivative
GB9325360D0 (en) * 1993-12-10 1994-02-16 Univ Bristol Organic compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1524225A (en) * 1966-09-14 1968-05-10 Lilly Co Eli Process for the preparation of 7-alpha-aminobenzyl-3-methyl cephalosporin analogs

Also Published As

Publication number Publication date
FR2187306B1 (en) 1976-12-31
FR2187306A1 (en) 1974-01-18
JPS4949983A (en) 1974-05-15
AU5695173A (en) 1974-12-19
AU470357B2 (en) 1976-03-11
DE2330296A1 (en) 1974-01-03
CA1003405A (en) 1977-01-11

Similar Documents

Publication Publication Date Title
GB1221855A (en) Penicillin and cephalosporin derivatives
ES8107231A1 (en) Cephem and cepham compounds, processes for their preparation, pharmaceutical compositions containing them.
GB1405886A (en) Synergistic compositions comprising penicillin and cephalosporin antibiotics
ES8608526A1 (en) New cephem compounds, processes for preparation thereof and pharmaceutical compositions containing them.
ES8506730A1 (en) New cephem compounds and processes for preparation thereof.
SE8004329L (en) PROCEDURE FOR THE PREPARATION OF ANTIBACTERIAL SUBSTANCES
DK0395219T3 (en) Cephalosporins and their homologs, methods of their preparation and pharmaceutical preparations
GB1456144A (en) Ureido-aryl cephalosporin compounds
KR850002992A (en) Method for preparing 3-bicyclic pyridinium-methyl sephalosporin
ATE87313T1 (en) CEPHEM COMPOUNDS, PROCESSES FOR THEIR PRODUCTION AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM.
KR840007731A (en) Process for preparing cephalosporin compound
GB1427211A (en) P-hydroxymethylphenylacetamido-cephalosporins
ES8800235A1 (en) Syn-isomer of 7-substituted-3-vinyl-3-cephem compounds, processes for production thereof and pharmaceutical compositions containing them.
EP0359536A3 (en) Cephalosporin compounds, process for their preparation and pharmaceutical compositions
IE40671L (en) Antibiotic composition containing a cephalosporin
GB1229453A (en)
GB1277415A (en) Improvements in or relating to cephalosporin derivatives
GB1460916A (en) Preparation of 3-thiolated-7-acylamido-cephalosporanic acid derivatives
IE37793L (en) 7-(hydroxy-halophenyl)acetamido-3-heterocyclicthiomethyl¹cephalosporins
GB1468102A (en) Cephalosporin derivatives their preparation and compositions containing them
IE43346L (en) Cephalosporin derivatives.
ATE32724T1 (en) CEPHALOSPORIN COMPOUNDS, PROCESSES FOR THEIR PRODUCTION AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM.
IE40517L (en) 3 - heterocyclic thiomethyl cephalosporins
US3891634A (en) P-Hydroxymethylphenylacetamidocephalosporins
ES8200371A1 (en) N-substituted thiazolyl derivatives of oxy-imino-substituted cephalosporins useful as anti-bacterial agents

Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee