SE7512818L - PROCEDURE FOR PREPARING DELTA? 723-CEPHALOSPORIN ASSOCIATIONS - Google Patents

PROCEDURE FOR PREPARING DELTA? 723-CEPHALOSPORIN ASSOCIATIONS

Info

Publication number
SE7512818L
SE7512818L SE7512818A SE7512818A SE7512818L SE 7512818 L SE7512818 L SE 7512818L SE 7512818 A SE7512818 A SE 7512818A SE 7512818 A SE7512818 A SE 7512818A SE 7512818 L SE7512818 L SE 7512818L
Authority
SE
Sweden
Prior art keywords
alkyl
formula
alkanoyl
cephalosporin
hydrogen
Prior art date
Application number
SE7512818A
Other languages
Swedish (sv)
Other versions
SE418616B (en
Inventor
J A Webber
Heyningen E M Van
Original Assignee
Lilly Co Eli
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 Lilly Co Eli filed Critical Lilly Co Eli
Publication of SE7512818L publication Critical patent/SE7512818L/en
Publication of SE418616B publication Critical patent/SE418616B/en

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)

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, &alpha;-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.
SE7512818A 1968-02-07 1975-11-14 PROCEDURE FOR PREPARATION OF DELTA? 723-CEPHALOSPORINE COMPOUNDS FROM 7-PROTECTED AMINO-DELTA? 722-CEPHALOSPORINE ESTERS SE418616B (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 (2)

Publication Number Publication Date
SE7512818L true SE7512818L (en) 1975-11-14
SE418616B SE418616B (en) 1981-06-15

Family

ID=27418758

Family Applications (3)

Application Number Title Priority Date Filing Date
SE6901500A SE384511B (en) 1968-02-07 1969-02-05 7-PROTECTED AMINO-DELTA? 722? 71-CEPHALOSPORANIC ACID, FOR USE AS INTERMEDIATE IN THE MANUFACTURE OF DELTA? 723? 71-CEPHALOSPORINE ANTIBIOTICS
SE7200411A SE407064B (en) 1968-02-07 1972-01-14 IN 7-FRAME PROTECTED 3-BROMOMETHYL-DELTAŸ2-CEPHALOSPORANIC ACID RESIDUES FOR USE AS AN INTERMEDIATE IN THE PRESENTATION OF ANTIBIOTIC ACTIVE DELTAŸ3-CEPHALOSPORANIC ACID DERIVATIVES
SE7512818A SE418616B (en) 1968-02-07 1975-11-14 PROCEDURE FOR PREPARATION OF DELTA? 723-CEPHALOSPORINE COMPOUNDS FROM 7-PROTECTED AMINO-DELTA? 722-CEPHALOSPORINE ESTERS

Family Applications Before (2)

Application Number Title Priority Date Filing Date
SE6901500A SE384511B (en) 1968-02-07 1969-02-05 7-PROTECTED AMINO-DELTA? 722? 71-CEPHALOSPORANIC ACID, FOR USE AS INTERMEDIATE IN THE MANUFACTURE OF DELTA? 723? 71-CEPHALOSPORINE ANTIBIOTICS
SE7200411A SE407064B (en) 1968-02-07 1972-01-14 IN 7-FRAME PROTECTED 3-BROMOMETHYL-DELTAŸ2-CEPHALOSPORANIC ACID RESIDUES FOR USE AS AN INTERMEDIATE IN THE PRESENTATION OF ANTIBIOTIC ACTIVE DELTAŸ3-CEPHALOSPORANIC ACID DERIVATIVES

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) GB1265332A (en)
IL (2) IL41553A (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
DK140726C (en) 1980-03-31
DK140726B (en) 1979-11-05
FR2085656A1 (en) 1971-12-31
JPS524558B1 (en) 1977-02-04
CH534694A (en) 1973-03-15
FI56535C (en) 1980-02-11
SE407064B (en) 1979-03-12
GB1265332A (en) 1972-03-01
FR2085656B1 (en) 1974-08-23
IL40447A (en) 1976-02-29
FR2001491A1 (en) 1969-09-26
NL173407B (en) 1983-08-16
FI56535B (en) 1979-10-31
IL41553A (en) 1976-02-29
FR2001491B1 (en) 1973-07-13
SE418616B (en) 1981-06-15
LU57932A1 (en) 1969-09-17
GB1265333A (en) 1972-03-01
FR2095486A5 (en) 1972-02-11
NL6902013A (en) 1969-08-11
JPS4924076B1 (en) 1974-06-20
SE384511B (en) 1976-05-10
JPS524559B1 (en) 1977-02-04
NL173407C (en) 1984-01-16
BE728053A (en) 1969-08-07

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