GB1416503A - 7-hydroxyhalophenylacetamido-3-heterocyclicthiomethyl cephalos porins - Google Patents

7-hydroxyhalophenylacetamido-3-heterocyclicthiomethyl cephalos porins

Info

Publication number
GB1416503A
GB1416503A GB2779473A GB2779473A GB1416503A GB 1416503 A GB1416503 A GB 1416503A GB 2779473 A GB2779473 A GB 2779473A GB 2779473 A GB2779473 A GB 2779473A GB 1416503 A GB1416503 A GB 1416503A
Authority
GB
United Kingdom
Prior art keywords
amino
fluoro
ylthiomethyl
cephem
acetamido
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
GB2779473A
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
Application filed by SmithKline Corp filed Critical SmithKline Corp
Publication of GB1416503A publication Critical patent/GB1416503A/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
    • C07D501/36—Methylene radicals, substituted by sulfur 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
    • 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
    • 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

1416503 Cephalosporins SMITHKLINE CORP 12 June 1973 [14 June 1972 15 Sept 1972 11 May 1973] 27794/73 Heading C2C Novel cephalosporins, having antibacterial activity, of formula wherein M is hydrogen, alkali metal or NH 4 , X is F, Cl or Br and Het is a 5- or 6-membered heterocyclic ring containing carbon and up to four N, O or S atoms, the heterocyclic moiety being substituted with up to 2 C 1 -C 4 alkyl, C 1 -C 4 alkenyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, CF 3 , OH, halogen, hydroxy- (C 1 -C 4 )alkyl or SR, R being hydrogen or C 1 -C 4 alkyl, are prepared by acylation of the appropriate 7-amino-3-heterocyclicthiomethyl cephalosporin with a 3-halo-4-hydroxyphenylglycine in which the amino group is protected with a removable protecting group such as t-butoxycarbonyl. Following acylation, the protective group may be removed by trifluoroacetic acid, and the resulting salt converted to the Zwitterionic product by means of a basic ion exchange resin. The compounds of Formula I may also be prepared by displacement of the 3-acetoxy group of a 7- acylated - 3 - acetoxymethylcephalosporin with a suitable mercapto-heterocyclic compound under basic conditions. The preparation of 7-[DL-α-amino-α-(3-fluoro-4-hydroxyphenyl) acetamido] - 3 - (5 - methyl - 1,3,4 - thiadiazol- 2 - ylthiomethyl - 3 - cephem - 4 - carboxylic acid, 7 - [DL - α - amino - α - (3 - fluoro - 4- hydroxyphenyl)acetamido] - 3 - (1 - methyl- 1,2,3,4 - tetrazol - 5 - ylthiomethyl) - 3 - cephem- 4 - carboxylic acid, 7 - [DL - α - amino - α- (3 - fluoro - 4 - hydroxyphenyl)acetamido] - 3- (1,2,3 - triazol - 4 - ylthiomethyl) - 3 - cephem- 4 - carboxylic acid and 7 - [DL - α - amino - α- (3 - chloro - 4 - hydroxyphenyl)acetamido] - 3- (1 - methyl - 1,2,3,4 - tetrazol - 5 - ylthiomethyl)- 3 - cephem - 4 - carboxylic acid is described (Examples 6 to 9). N - t - butoxycarbonyl - 3 - fluoro - 4 - hydroxyphenylglycine is prepared by reacting 3-fluoro - 4-hydroxyphenylglyeine with t-butoxycarbonyl azide in the presence of magnesium oxide. The corresponding 3-chloro and 3-bromo cornpounds are prepared in a similar manner.
GB2779473A 1972-06-14 1973-06-12 7-hydroxyhalophenylacetamido-3-heterocyclicthiomethyl cephalos porins Expired GB1416503A (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
US35956773A 1973-05-11 1973-05-11

Publications (1)

Publication Number Publication Date
GB1416503A true GB1416503A (en) 1975-12-03

Family

ID=27401552

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2779473A Expired GB1416503A (en) 1972-06-14 1973-06-12 7-hydroxyhalophenylacetamido-3-heterocyclicthiomethyl cephalos porins

Country Status (10)

Country Link
JP (1) JPS4949984A (en)
AU (1) AU474443B2 (en)
CA (1) CA999574A (en)
CH (1) CH585228A5 (en)
DE (1) DE2330307C2 (en)
ES (1) ES415874A1 (en)
FR (1) FR2187305B1 (en)
GB (1) GB1416503A (en)
IE (1) IE37793B1 (en)
NL (1) NL7308199A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2215942B1 (en) * 1973-01-31 1978-12-22 Bristol Myers Co
AR207752A1 (en) 1973-03-30 1976-10-29 Fujisawa Pharmaceutical Co PROCEDURE FOR OBTAINING 7-AMINO-SUBSTITUTED-3-THIOMETHYL SUBSTITUTED-3-CEFEM-4-CARBOXYL ACIDS
CA1074784A (en) * 1974-09-06 1980-04-01 Sumitomo Chemical Company N-ACYLAMINO-.alpha.-ARYLACETAMIDO CEPHALOSPORINS
IL49183A0 (en) * 1975-03-27 1976-05-31 Pfizer Novel cephalosporin derivatives,their preparation and pharmaceutical compositions containing them
JPS5346995A (en) * 1976-10-12 1978-04-27 Sangyo Kagaku Kenkyu Kyokai Antibacterial agents
WO2010087425A1 (en) 2009-01-30 2010-08-05 国立大学法人京都大学 Prostate cancer progression inhibitor and progression inhibition method

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3641021A (en) * 1969-04-18 1972-02-08 Lilly Co Eli 3 7-(ring-substituted) cephalosporin compounds

Also Published As

Publication number Publication date
IE37793B1 (en) 1977-10-12
AU474443B2 (en) 1976-07-22
CH585228A5 (en) 1977-02-28
JPS4949984A (en) 1974-05-15
IE37793L (en) 1973-12-14
NL7308199A (en) 1973-12-18
AU5695273A (en) 1974-12-19
DE2330307A1 (en) 1974-01-03
DE2330307C2 (en) 1983-03-10
ES415874A1 (en) 1976-02-01
FR2187305A1 (en) 1974-01-18
CA999574A (en) 1976-11-09
FR2187305B1 (en) 1976-12-03

Similar Documents

Publication Publication Date Title
ES8101596A1 (en) Antibacterial beta-lactams, pharmaceuticals thereof and methods of using them
JPS61267583A (en) Novel beta-lactam antibiotic
ES8107231A1 (en) Cephem and cepham compounds, processes for their preparation, pharmaceutical compositions containing them.
ES8704955A1 (en) New cephalosporin compounds and the production thereof.
ES8306160A1 (en) New cephem compounds, processes for their preparation, pharmaceutical compositions containing them and their starting compounds.
ES8608526A1 (en) New cephem compounds, processes for preparation thereof and pharmaceutical compositions containing them.
ES8200685A1 (en) 3-optionally substituted methyl-2- penem derivatives
ES8307824A1 (en) New cephem compounds and processes for preparation thereof.
GB1416503A (en) 7-hydroxyhalophenylacetamido-3-heterocyclicthiomethyl cephalos porins
ES412859A1 (en) Process for preparing 7-(alpha-hydroxy-alpha-phenyl)acetamido-3-(1-methyl-1h-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid and derivatives thereof
JPS5692893A (en) Novel cephem compound, its preparation, and preventive and remedy for bacteriosis containing said compound as effective component
GB1260882A (en) New penicillins
GB1573004A (en) Cephalosporin compounds
US3880848A (en) 7-Trifluorome thylsulfinylacetamido cephalosporins
ES403305A1 (en) Cephalosporins
GB1363833A (en) 3-heterocyclic thiomethylcephalosporins
JPS5533500A (en) 3,7-disubstituted-3-cephem-4-carboxylic acid, its salt, their preparation, and preventive and remedy for microbism
US3884915A (en) 7-Alkylmercaptoacetamido cephalosporins
ES8104306A1 (en) N-(6-((acylaminoacylamino or aminoacylamino)phenyl)-1,2-dihydro-2-oxonicotinyl) cephalosporin compounds, processes for their production, and compositions containing the same.
US3929781A (en) Certain cephalosporanic acid derivatives
US4144241A (en) 5-Sulfomethyl-1,3,4-thiadiazole-2-thiol
GB1427211A (en) P-hydroxymethylphenylacetamido-cephalosporins
GB1472174A (en) Dihydroxy amino cephalosporins
US4133882A (en) 7-Hydroxyhalophenylacetamido-3-heterocyclicthiomethyl cephalosporins
GB1420728A (en) Cephalosporins

Legal Events

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