GB1265333A - - Google Patents

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Publication number
GB1265333A
GB1265333A GB1265333DA GB1265333A GB 1265333 A GB1265333 A GB 1265333A GB 1265333D A GB1265333D A GB 1265333DA GB 1265333 A GB1265333 A GB 1265333A
Authority
GB
United Kingdom
Prior art keywords
alkyl
formula
alkanoyl
hydrogen
group
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
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 filed Critical
Publication of GB1265333A publication Critical patent/GB1265333A/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
    • A61K31/54—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
    • 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
    • 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
    • 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
    • C07D501/60—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 3 and 4
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

1,265,333. Preparing #<SP>3</SP>-cephalosporins from #<SP>2</SP>-cephalosporins. ELI LILLEY & CO. 7 Feb., 1969 [7 Feb., 1968; 13 Jan., 1969 (2)], No. 33268/70. Heading C2A. #<SP>3</SP>-Cephalosporin compounds are prepared by treating a corresponding #<SP>2</SP>-cephalosporin with an oxidizing agent to convert it to the #<SP>3</SP>- cephalosporin-1-sulphoxide and then reducing the sulphoxide. The #<SP>3</SP>-cephalosporins produced have the Formula I wherein R is hydrogen, a group of formula where X is amino, protected amino, hydroxy, C 1 to C 3 alkoxy, carboxyl or C 1 to C 3 alkanoyloxy; or R is a group of formula where X is oxygen, sulphur or a chemical bond, y is 0-2 and z is 1-3; or R is a group of formula and Q in each of the aforesaid groups is hydrogen, CN, NO 2 , OH, Cl, Br, F, CF 3 , C 1 to C 3 alkyl, C 1 to C 3 alkoxy, α-amino-C 1 to C 3 alkyl, carboxymethyl or carboxamidomethyl; or R is a group of formula where Y is sulphur or oxygen and each Z is hydrogen or Z and Z together with the carbons to which they are bonded complete a benzoring; or R is a group of formula where each of R<SP>1</SP> and R<SP>2</SP> is hydrogen, methyl, 2-sydnone-3-C 1 to C 3 alkanoyl, C 1 to C 10 alkanoyl, C 3 to C 10 alkenoyl, C 3 to C 7 alkyl-X-C 1 to C 3 alkanoyl where X is O or S, C 3 to C 7 alkenyl-XC 1 to C 3 alkanoyl where X is O or S, C 2 to C 10 haloalkanoyl where halo is Cl, Br or F, or C 2 to C 10 cyanoalkanoyl; and R<SP>1</SP> is cyano or -OY where Y is C 1 to C 10 alkyl, C 3 to C 10 alkenyl, C 3 to C 10 alkynyl, C 6 to C 7 cycloalkyl, C 5 to C 7 cycloalkyl-C 1 to C 3 alkyl, C 2 to C 10 haloalkyl, C 3 to C 10 haloalkenyl or C 3 to C 10 haloalkynyl, C 1 to C 3 alkyl-X-C 2 to C 6 alkyl where X is O or S, C 2 to C 4 alkanoyloxy-C 2 to C 6 alkyl, C 2 to C 4 alkanoyl-C 2 to C 6 alkyl, furyl-C 1 to C 3 alkyl, thienyl-C 1 to C 3 alkyl, 31-tetrahydrofuryl, tetrahydrofuryl-C 1 to C 3 alkyl, or phenyl, benzyl or phenethyl optionally substituted on ring carbons with C 1 to C 3 alkyl, C 1 to C 3 alkoxy, C 1 to C 3 alkoxycarbonyl, F, Cl, Br, NO 2 , CN or CF 3 ; and R<SP>11</SP> is hydrogen, a zwitterionic charge, a cation, C 4 to C 6 tert. alkyl, C 5 to C 7 tert. alkenyl, C 5 -C 7 tert. alkynyl, benzyl, methoxybenzyl, nitrobenzyl, benzhydryl, phthalimidomethyl, succinimidomethyl, trimethylsilyl or a phenacyl ester group. The corresponding #<SP>2</SP>-cephalosporin starting materials may be prepared by the process of Specification 1,265,332. The present process preferably employs oxidation with a per-acid, e.g. m-chloroperbenzoic acid, followed by reduction with sodium bisulphite or dithionite in the presence of an activator, e.g. acetyl chloride. Examples also are given for an alternative process wherein the #<SP>2</SP>-cephalosporin is partially isomerized with a base, e.g. pyridine, to give a mixture of #<SP>2</SP>- and #<SP>2</SP>-cephalosporins. Among the compounds prepared according to the invention are novel cephalosporins having the Formula I (as above), wherein R is 2-sydnone- 3-C 1 to C 3 alkanoyl, R<SP>1</SP> is -OY where Y is C 1 to C 10 alkyl, and R<SP>11</SP> is hydrogen.
GB1265333D 1968-02-07 1969-02-07 Expired GB1265333A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US70352368A 1968-02-07 1968-02-07
US79088669A 1969-01-13 1969-01-13
US79084269A 1969-01-13 1969-01-13

Publications (1)

Publication Number Publication Date
GB1265333A true GB1265333A (en) 1972-03-01

Family

ID=27418758

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1265333D Expired GB1265333A (en) 1968-02-07 1969-02-07
GB1265332D Expired GB1265332A (en) 1968-02-07 1969-02-07

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1265332D Expired GB1265332A (en) 1968-02-07 1969-02-07

Country Status (11)

Country Link
JP (3) JPS524558B1 (en)
BE (1) BE728053A (en)
CH (1) CH534694A (en)
DK (1) DK140726B (en)
FI (1) FI56535C (en)
FR (3) FR2001491B1 (en)
GB (2) GB1265333A (en)
IL (2) IL40447A (en)
LU (1) LU57932A1 (en)
NL (1) NL173407C (en)
SE (3) SE384511B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1360860A (en) * 1970-07-08 1974-07-24 Ciba Geigy Ag Cepham compounds process for their manufacture and compositions containing them
JPS53164082U (en) * 1977-05-31 1978-12-22
JPS5899787U (en) * 1981-12-28 1983-07-07 奥野電器株式会社 lamp socket
EP0300546B1 (en) * 1987-07-10 1995-08-09 Gist-Brocades N.V. Process for the preparation of cephem compounds and cephalosporin derivatives

Also Published As

Publication number Publication date
SE7512818L (en) 1975-11-14
DK140726B (en) 1979-11-05
CH534694A (en) 1973-03-15
FI56535B (en) 1979-10-31
JPS524559B1 (en) 1977-02-04
IL41553A (en) 1976-02-29
NL173407C (en) 1984-01-16
JPS4924076B1 (en) 1974-06-20
FR2085656B1 (en) 1974-08-23
FI56535C (en) 1980-02-11
NL173407B (en) 1983-08-16
SE384511B (en) 1976-05-10
SE418616B (en) 1981-06-15
FR2085656A1 (en) 1971-12-31
FR2001491B1 (en) 1973-07-13
SE407064B (en) 1979-03-12
FR2001491A1 (en) 1969-09-26
DK140726C (en) 1980-03-31
LU57932A1 (en) 1969-09-17
IL40447A (en) 1976-02-29
FR2095486A5 (en) 1972-02-11
NL6902013A (en) 1969-08-11
GB1265332A (en) 1972-03-01
JPS524558B1 (en) 1977-02-04
BE728053A (en) 1969-08-07

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Legal Events

Date Code Title Description
PS Patent sealed
PS Patent sealed
PE20 Patent expired after termination of 20 years