GB1277578A - Penicillins - Google Patents

Penicillins

Info

Publication number
GB1277578A
GB1277578A GB31884/68A GB3188468A GB1277578A GB 1277578 A GB1277578 A GB 1277578A GB 31884/68 A GB31884/68 A GB 31884/68A GB 3188468 A GB3188468 A GB 3188468A GB 1277578 A GB1277578 A GB 1277578A
Authority
GB
United Kingdom
Prior art keywords
acid
methyl
acetic acid
produced
sulphonyl
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
GB31884/68A
Inventor
Erik Falch
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.)
Pharmacia AS
Original Assignee
Pharmacia AS
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 Pharmacia AS filed Critical Pharmacia AS
Priority to GB31884/68A priority Critical patent/GB1277578A/en
Priority to CH997069A priority patent/CH532613A/en
Priority to SE6909368A priority patent/SE394679B/en
Priority to FR6922351A priority patent/FR2012283B1/fr
Priority to DE1933629A priority patent/DE1933629C3/en
Priority to AT633169A priority patent/AT303957B/en
Priority to NO2787/69A priority patent/NO140103C/en
Priority to CA055,997A priority patent/CA1024982A/en
Priority to DK362069A priority patent/DK131862C/en
Priority to FI1979/69A priority patent/FI53215C/fi
Priority to NL6910336.A priority patent/NL156320B/en
Priority to JP5278469A priority patent/JPS536157B1/ja
Publication of GB1277578A publication Critical patent/GB1277578A/en
Priority to DK272275A priority patent/DK272275A/da
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
    • 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
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1277578 Sulphonyl benzylpenicillins PHARMACIA SA 26 June 1969 [4 July 1968] 31884/68 Headings C2A and C2C The invention comprises α-sulphonyl benzyl penicillins of Formula I wherein R<SP>1</SP> is H, alkyl, aryl, aralkyl, cycloalkyl or heterocyclyl; R<SP>2</SP> is OH, alkyl, aryl, aralkyl, cycloalkyl or heterocyclyl; X, Y and Z are the same or different and each represents H, halogen, alkyl, aryl, aralkyl, cycloalkyl, heterocyclyl, alkoxy, aryloxy, trifluoromethyl, OH, NO 2 , acyloxy, acylamino, dialkylamino or a sulphonylamino group; and salts and esters thereof. The penicillins are prepared by reacting 6-aminopenicillanic acid or an ester thereof with an acid of Formula II wherein R<SP>1</SP>, R<SP>2</SP>, X, Y and Z have the above meanings, or a reactive derivative thereof, and if appropriate, salifying or esterifying the N- acylated product or converting it to the free penicillin. The salts may be sodium, potassium, calcium, aluminium, ammonium or amine salts e.g. procaine and triethanol-amine salts. The esters may be ethyl, benzyl or acetoxy-methyl esters. α-Methyl sulphonyl phenyl acetic acid is produced by oxidizing α-methylthiophenylacetic acid with hydrogen peroxide in glacial acetic acid. The 2-, 3-, or 4-chloro-, 4-fluoro-, 2- or 4- methyl or 2-methoxy-phenyl substituted compounds are produced from the corresponding α- methylthio-substituted phenyl acetic acids in a similar manner. α-Iso-butyl sulphonyl phenyl acetic acid is produced by oxidizing α-isobutylthiophenyl. acetic acid with hydrogen peroxide in glacial acetic acid. The α-methyl thio-substituted phenyl acetic acids or the α-iso-butylthiophenylacetic acid are produced from the corresponding α-halo phenyl acetic acids by reaction with sodium methyl mercaptan or sodium isobutyl mercaptan in methanol.
GB31884/68A 1968-07-04 1968-07-04 Penicillins Expired GB1277578A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
GB31884/68A GB1277578A (en) 1968-07-04 1968-07-04 Penicillins
CH997069A CH532613A (en) 1968-07-04 1969-06-30 Process for the preparation of benzyl penicillins
SE6909368A SE394679B (en) 1968-07-04 1969-07-02 WAY TO PRODUCE NEW PENICILLINES
FR6922351A FR2012283B1 (en) 1968-07-04 1969-07-02
DE1933629A DE1933629C3 (en) 1968-07-04 1969-07-02 Alpha-substituted benzyl penicillins and processes for their preparation
AT633169A AT303957B (en) 1968-07-04 1969-07-02 Process for the preparation of new benzyl penicillins
CA055,997A CA1024982A (en) 1968-07-04 1969-07-03 Penicillins
NO2787/69A NO140103C (en) 1968-07-04 1969-07-03 ANALOGICAL PROCEDURE FOR THE PREPARATION OF THERAPEUTICALLY EFFECTIVE PENICILLINES
DK362069A DK131862C (en) 1968-07-04 1969-07-03 ANALOGICAL PROCEDURE FOR THE PREPARATION OF PENICILLINS OR SALTS THEREOF
FI1979/69A FI53215C (en) 1968-07-04 1969-07-03
NL6910336.A NL156320B (en) 1968-07-04 1969-07-04 PROCESS FOR THE PREPARATION OF BENZYLPENICILLIN DERIVATIVES, PROCESS FOR THE PREPARATION OF PHARMACEUTICAL PREPARATIONS, AND THE PREPARATIONS THEREFORE OBTAINED.
JP5278469A JPS536157B1 (en) 1968-07-04 1969-07-04
DK272275A DK272275A (en) 1968-07-04 1975-06-17

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB31884/68A GB1277578A (en) 1968-07-04 1968-07-04 Penicillins

Publications (1)

Publication Number Publication Date
GB1277578A true GB1277578A (en) 1972-06-14

Family

ID=10329836

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31884/68A Expired GB1277578A (en) 1968-07-04 1968-07-04 Penicillins

Country Status (12)

Country Link
JP (1) JPS536157B1 (en)
AT (1) AT303957B (en)
CA (1) CA1024982A (en)
CH (1) CH532613A (en)
DE (1) DE1933629C3 (en)
DK (1) DK131862C (en)
FI (1) FI53215C (en)
FR (1) FR2012283B1 (en)
GB (1) GB1277578A (en)
NL (1) NL156320B (en)
NO (1) NO140103C (en)
SE (1) SE394679B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2119363A (en) * 1981-05-22 1983-11-16 Beecham Group Plc Penicillanic acid derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT290728B (en) * 1968-09-28 1971-05-15 Takeda Chemical Industries Ltd METHOD FOR MANUFACTURING NEW PENICILLIN

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3382238A (en) * 1967-04-27 1968-05-07 Squibb & Sons Inc Penicillin and cephalosporin derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2119363A (en) * 1981-05-22 1983-11-16 Beecham Group Plc Penicillanic acid derivatives

Also Published As

Publication number Publication date
NO140103C (en) 1979-07-04
DE1933629C3 (en) 1975-07-31
DE1933629A1 (en) 1970-09-03
CH532613A (en) 1973-01-15
SE394679B (en) 1977-07-04
DK131862C (en) 1976-07-19
NO140103B (en) 1979-03-26
CA1024982A (en) 1978-01-24
FR2012283A1 (en) 1970-03-20
FI53215B (en) 1977-11-30
NL6910336A (en) 1970-01-06
DE1933629B2 (en) 1974-12-19
AT303957B (en) 1972-12-27
FR2012283B1 (en) 1973-12-21
NL156320B (en) 1978-04-17
JPS536157B1 (en) 1978-03-04
DK131862B (en) 1975-09-15
FI53215C (en) 1978-03-10

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Legal Events

Date Code Title Description
PS Patent sealed
PLE Entries relating assignments, transmissions, licences in the register of patents
PE20 Patent expired after termination of 20 years