GB1348198A - Acyl aminopenicillanic acid derivatives - Google Patents

Acyl aminopenicillanic acid derivatives

Info

Publication number
GB1348198A
GB1348198A GB160273A GB160273A GB1348198A GB 1348198 A GB1348198 A GB 1348198A GB 160273 A GB160273 A GB 160273A GB 160273 A GB160273 A GB 160273A GB 1348198 A GB1348198 A GB 1348198A
Authority
GB
United Kingdom
Prior art keywords
acid
formula
furyl
thienyl
alkoxy
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
GB160273A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1348198A publication Critical patent/GB1348198A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1348198 Penicillins F HOFFMAN-LA ROCHE & CO AG 11 Jan 1973 [12 Jan 1972] 1602/73 Headings C2A and C2C Novel penicillins having the general Formula (I) and salts thereof, wherein R<SP>1</SP> is a hydrogen atom or a C 1-6 alkyl group and R<SP>2</SP> is phenyl, halophenyl, nitrophenyl, C 1-6 alkoxy-phenyl, thienyl, C 1-6 alkyl-thienyl, C 1-6 alkoxy-thienyl, furyl, C 1-6 alkyl-furyl or C 1-6 alkoxy-furyl, are prepared by N-acylating 6-aminopenicillanic acid (having the carboxyl group protected) with an acid of Formula (II) wherein R<SP>1</SP> and R<SP>2</SP> have the aforesaid meanings, or with an N-acylating functional derivative thereof, and cleaving off the carboxyl-protecting group. The carboxyl group may be protected by saltformation or esterification. Functional derivatives of the acid (II) are, e.g. halides, azides, anhydrides, reactive esters and active amides. When the acid itself is used, a condensing agent such as dicyclohexylcarbodiimide is preferably present. The reaction is usually performed in an inert solvent. Acids of Formula (II) above, which are said to be novel, are prepared by reacting the (optionally substituted) aromatic thiocarboxylic acid: R<SP>2</SP>COSH with an α-bromo derivative of the aliphatic carboxylic acid: R<SP>1</SP>CH.COOH in aqueous Na 2 CO 3 solution. The acid II is converted to the corresponding acid chloride by treatment with thionyl chloride. Pharmaceutical compositions with antibiotic activity against Gram-positive and -negative bacteria comprise a penicillin of Formula (I) hereinbefore or a salt or hydrate thereof in association with a compatible pharmaceutical carrier.
GB160273A 1972-01-12 1973-01-11 Acyl aminopenicillanic acid derivatives Expired GB1348198A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH43372A CH564021A5 (en) 1972-01-12 1972-01-12

Publications (1)

Publication Number Publication Date
GB1348198A true GB1348198A (en) 1974-03-13

Family

ID=4186906

Family Applications (1)

Application Number Title Priority Date Filing Date
GB160273A Expired GB1348198A (en) 1972-01-12 1973-01-11 Acyl aminopenicillanic acid derivatives

Country Status (10)

Country Link
JP (1) JPS4880586A (en)
AU (1) AU5038572A (en)
BE (1) BE793884A (en)
CH (1) CH564021A5 (en)
DE (1) DE2301545A1 (en)
FR (1) FR2181665B1 (en)
GB (1) GB1348198A (en)
IL (1) IL41140A0 (en)
NL (1) NL7300132A (en)
ZA (1) ZA728925B (en)

Also Published As

Publication number Publication date
ZA728925B (en) 1973-09-26
AU5038572A (en) 1974-06-27
CH564021A5 (en) 1975-07-15
IL41140A0 (en) 1973-02-28
JPS4880586A (en) 1973-10-29
DE2301545A1 (en) 1973-07-19
FR2181665B1 (en) 1976-07-02
BE793884A (en) 1973-07-11
NL7300132A (en) 1973-07-16
FR2181665A1 (en) 1973-12-07

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees