GB1442993A - Penicillin and cephalosporin r-sulphoxides - Google Patents

Penicillin and cephalosporin r-sulphoxides

Info

Publication number
GB1442993A
GB1442993A GB3359672A GB3359672A GB1442993A GB 1442993 A GB1442993 A GB 1442993A GB 3359672 A GB3359672 A GB 3359672A GB 3359672 A GB3359672 A GB 3359672A GB 1442993 A GB1442993 A GB 1442993A
Authority
GB
United Kingdom
Prior art keywords
sulphoxides
cephalosporin
group
penicillin
oxidation
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
GB3359672A
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.)
Gist Brocades NV
Original Assignee
Gist Brocades NV
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 Gist Brocades NV filed Critical Gist Brocades NV
Priority to GB3359672A priority Critical patent/GB1442993A/en
Priority to JP8242073A priority patent/JPS4980089A/ja
Priority to FR7326172A priority patent/FR2192805B1/fr
Priority to DE19732336344 priority patent/DE2336344A1/en
Priority to AT626873A priority patent/AT341665B/en
Priority to HUGI000193 priority patent/HU170698B/hu
Priority to NL7309918A priority patent/NL7309918A/xx
Priority to US05/633,006 priority patent/US4075337A/en
Publication of GB1442993A publication Critical patent/GB1442993A/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
    • C07D501/02—Preparation
    • C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • A61K31/43—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
    • 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
    • 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
    • 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
    • C07D499/04—Preparation
    • 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
    • C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6

Abstract

1442993 Penicillin and cephalosporin R-sulphoxides GIST-BROCADES NV 17 July 1973 [18 July 1972 23 Oct 1972] 33596/72 and 48270/72 Heading C2C The invention is directed to R-sulphoxides of 6-substituted amino penicillanic acids and 7- substituted amino cephalosporanic acids and derivatives and esters and salts thereof, these R-sulphoxides being free from association with S-sulphoxides of such penicillin or cephalosporin compounds. These R-sulphoxides have the formula wherein X is hydrogen, hydroxyl, alkanoyloxy or a nucleophilic group and the group represents a usual penicillin or cephalosporin amide group The R-sulphoxides may be prepared by the oxidation of the corresponding penicillins and cephalosporins to convert the sulphur atom to a sulphoxide group by the generation of a singlet oxygen species, and separating the R-sulphoxide from the reaction mixture. This oxidation is preferably carried out by irradiating a mixture of a sensitizer and a cephalosporin starting material in an inert organic solvent, said irradiation being carried out with light at below ambient temperature, air or oxygen being continuously passed through the solvent The solvent may be methanol, the reaction temperature - 30‹ to - 10‹ C. and the sensitizer methylene blue, cosine, fluoresceine, rhodamine B or a mixture thereof. The invention further comprises compounds of the general formula wherein X is as defined above and Q 1 <SP>1</SP> and Q 2 1 together with the nitrogen atom to which they are attached comprise a protected amine group. These compounds may be prepared by the oxidation of the corresponding penicillin and cephalosporin materials with perbenzoic acid in an inert solvent under anhydrous conditions. The protected amine group may be replaced by a free amino group by hydrolysis, preferably under acid conditions. The R-sulphoxides may be incorporated with physiologically acceptable carriers or diluents to form antibacterial compositions.
GB3359672A 1972-07-18 1972-07-18 Penicillin and cephalosporin r-sulphoxides Expired GB1442993A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB3359672A GB1442993A (en) 1972-07-18 1972-07-18 Penicillin and cephalosporin r-sulphoxides
JP8242073A JPS4980089A (en) 1972-07-18 1973-07-17
FR7326172A FR2192805B1 (en) 1972-07-18 1973-07-17
DE19732336344 DE2336344A1 (en) 1972-07-18 1973-07-17 PENICILLIN AND CEPHALOSPORIN RSULFOXIDES, THEIR SALTS AND ESTERS, THE PROCESS FOR THEIR MANUFACTURING AND THE MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
AT626873A AT341665B (en) 1972-07-18 1973-07-17 PROCESS FOR THE PREPARATION OF NEW R-SULFOXYDE FROM 7-AMINO-CEPHALOSPORANIC ACIDS
HUGI000193 HU170698B (en) 1972-07-18 1973-07-17
NL7309918A NL7309918A (en) 1972-07-18 1973-07-17
US05/633,006 US4075337A (en) 1972-07-18 1975-11-18 Methods of combatting bacterial infections in warm-blooded animal with cephalsporin R-sulfoxide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3359672A GB1442993A (en) 1972-07-18 1972-07-18 Penicillin and cephalosporin r-sulphoxides
GB4872072 1972-10-23

Publications (1)

Publication Number Publication Date
GB1442993A true GB1442993A (en) 1976-07-21

Family

ID=26261933

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3359672A Expired GB1442993A (en) 1972-07-18 1972-07-18 Penicillin and cephalosporin r-sulphoxides

Country Status (7)

Country Link
JP (1) JPS4980089A (en)
AT (1) AT341665B (en)
DE (1) DE2336344A1 (en)
FR (1) FR2192805B1 (en)
GB (1) GB1442993A (en)
HU (1) HU170698B (en)
NL (1) NL7309918A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017419A1 (en) * 1979-03-26 1980-10-15 Eli Lilly And Company Process for preparing penicillin sulfoxides

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6019316B2 (en) * 1976-01-29 1985-05-15 塩野義製薬株式会社 penicillin oxide
DE2716677C2 (en) * 1977-04-15 1985-10-10 Hoechst Ag, 6230 Frankfurt Cephem derivatives and processes for their preparation
JPS58986A (en) * 1981-05-07 1983-01-06 Fujisawa Pharmaceut Co Ltd 7-acylamino-3-vinylcephalosporanic acid derivative and its preparation
US5442058A (en) * 1989-10-16 1995-08-15 Akzo Nobel N.V. Conversion of penicillins and cephalosporins to 1-(S)-sulfoxides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017419A1 (en) * 1979-03-26 1980-10-15 Eli Lilly And Company Process for preparing penicillin sulfoxides

Also Published As

Publication number Publication date
AT341665B (en) 1978-02-27
ATA626873A (en) 1977-06-15
NL7309918A (en) 1974-01-22
DE2336344A1 (en) 1974-03-14
FR2192805B1 (en) 1976-09-03
HU170698B (en) 1977-08-28
JPS4980089A (en) 1974-08-02
FR2192805A1 (en) 1974-02-15

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Legal Events

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