GB1412721A - Antibacterial agents and processes for their preparation - Google Patents

Antibacterial agents and processes for their preparation

Info

Publication number
GB1412721A
GB1412721A GB4096273A GB4096273A GB1412721A GB 1412721 A GB1412721 A GB 1412721A GB 4096273 A GB4096273 A GB 4096273A GB 4096273 A GB4096273 A GB 4096273A GB 1412721 A GB1412721 A GB 1412721A
Authority
GB
United Kingdom
Prior art keywords
acid
ylaminomethyl
compound
formula
carbomethoxypropen
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
GB4096273A
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.)
Bristol Myers Co
Original Assignee
Bristol Myers Co
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 US00285764A external-priority patent/US3813376A/en
Priority claimed from US00286630A external-priority patent/US3813390A/en
Priority claimed from US00286792A external-priority patent/US3823141A/en
Application filed by Bristol Myers Co filed Critical Bristol Myers Co
Publication of GB1412721A publication Critical patent/GB1412721A/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
    • 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
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
    • C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/24—Oxygen 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

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

1412721 Cephen compounds BRISTOLMYERS CO 30 Aug 1973 [31 Aug 1972 6 Sept 1972 (2)] 40962/73 Heading C2C Novel cephalosporin compounds having the general Formula (I): wherein Z is H or a group of formula in which X is H or OH and m is 0 or 1, provided that when X is OH, m is 0, and salts thereof, esters thereof and N-protected derivatives thereof, are prepared by reacting 7-aminocephalosporanic acid or a salt thereof, with a thiol of formula or a salt thereof, to give a compound (I) wherein Z is H, and, if desired, converting said compound into a salt or ester thereof, and, if required, reacting the compound (I) wherein Z is H with an acid of formula or an N-acylating derivative thereof, wherein B is an amino-protecting group and X and m are as defined above, to give a corresponding N-acyl compound (I), and, if desired, removing the amino-protecting group, and optionally salifying or esterifying the said compound. The following starting materials and intermediates are also prepared :-2-cyano-4-methoxyphenylacetic acid; 2 - aminomethyl - 4 - methoxyphenylacetic acid, and its hydrochloride; 2- aminomethyl - 4 - hydroxyphenylacetic acid; 2- t - butoxycarbonylaminomethyl - 4 - hydroxyphenylacetic acid; potassium o - [1 - carbomethoxypropen - 2 - ylaminomethyl] - p - hydroxyphenyl acetate; sodium o-(l-ethoxycarbonyl-lpropen - 2 - ylaminomethyl) - p - hydroxyphenylacetate; t - butoxycarbonyl azide; 3 - chloro - 6- hydroxypyridazine; 3 - hydroxy - 6 - mercaptopyridazine; 3,6 - dihydroxypyridazine; 3,6 - dichloropyridazine; 6 - chloro - 3 - hydroxypyridazine; potassium o - (1 - carbomethoxypropen - 2- ylaminomethyl)phenylthioacetate; sodium o - (1- ethoxycarbonyl - 1 - propen - 2 - ylaminomethyl)- phenylthioacetate; methyl o - bromomethylphenylacetate; o - azidomethylphenylacetic acid; oaminomethylphenylacetic acid; o-t-butoxycarbonylaminomethylphenylacetic acid; 2,4 - dinitrophenyl - o - t - butoxycarbonylaminophenylacetate o - aminomethylphenylacetic acid hydrochloride and #-lactam; 2-indanone; o-nitrophenylacetic acid; o-cyanophenylacetic acid; potassium o-(1- carbomethoxypropen - 2 - ylaminomethyl)phenylacetate; sodium o - (I - ethoxycarbonyl - 1 - propen - 2 - ylaminomethyl)phenylacetate; and 2,4- dinitro - o - t - butoxycarbonylaminomethylphenylacetate. The compounds (I) wherein Z is other than H have antibacterial activity and may be admixed with a pharmaceutically acceptable diluent or carrier to provide pharmaceutical compositions.
GB4096273A 1972-08-31 1973-08-30 Antibacterial agents and processes for their preparation Expired GB1412721A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US00285764A US3813376A (en) 1972-08-31 1972-08-31 7-(o-aminomethylphenyl-acetamido)-3-(3-hydroxypyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid
US00286630A US3813390A (en) 1972-09-06 1972-09-06 7-(o-aminomethylphenylthioacetamido)-3-(3-hydroxypyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid
US00286792A US3823141A (en) 1972-09-06 1972-09-06 7-(o-aminomethyl-p-hydroxy-phenylacetamido)-3-(3-hydroxy-pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid

Publications (1)

Publication Number Publication Date
GB1412721A true GB1412721A (en) 1975-11-05

Family

ID=27403558

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4096273A Expired GB1412721A (en) 1972-08-31 1973-08-30 Antibacterial agents and processes for their preparation

Country Status (10)

Country Link
JP (1) JPS5930716B2 (en)
AU (1) AU476592B2 (en)
DE (1) DE2344095A1 (en)
DK (1) DK145465C (en)
ES (1) ES418328A1 (en)
FI (1) FI57420C (en)
FR (1) FR2279408A1 (en)
GB (1) GB1412721A (en)
NL (1) NL7312062A (en)
SE (1) SE415980B (en)

Also Published As

Publication number Publication date
NL7312062A (en) 1974-03-04
AU5974273A (en) 1975-03-06
SE415980B (en) 1980-11-17
JPS5930716B2 (en) 1984-07-28
FR2279408A1 (en) 1976-02-20
FI57420C (en) 1980-08-11
DK145465B (en) 1982-11-22
AU476592B2 (en) 1976-09-30
JPS4992091A (en) 1974-09-03
DE2344095A1 (en) 1974-04-18
ES418328A1 (en) 1976-09-01
DK145465C (en) 1983-04-18
FR2279408B1 (en) 1978-07-28
FI57420B (en) 1980-04-30

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Legal Events

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