ES446353A1 - Production of cephalosporin derivative - Google Patents

Production of cephalosporin derivative

Info

Publication number
ES446353A1
ES446353A1 ES76446353A ES446353A ES446353A1 ES 446353 A1 ES446353 A1 ES 446353A1 ES 76446353 A ES76446353 A ES 76446353A ES 446353 A ES446353 A ES 446353A ES 446353 A1 ES446353 A1 ES 446353A1
Authority
ES
Spain
Prior art keywords
formula
group
reaction
lower alkyl
hydrogen
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
ES76446353A
Other languages
Spanish (es)
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.)
Pfizer Ltd
Pfizer Corp
Original Assignee
Pfizer Ltd
Pfizer Corp
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
Priority claimed from GB7512813A external-priority patent/GB1542397A/en
Application filed by Pfizer Ltd, Pfizer Corp filed Critical Pfizer Ltd
Publication of ES446353A1 publication Critical patent/ES446353A1/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
    • C07D501/14—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
    • C07D501/36—Methylene radicals, substituted by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • 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)
  • Cephalosporin Compounds (AREA)

Abstract

Procedure to prepare cephalosporins of formula: **(See formula)** where R is H or OH; Y is NH2, OH or OR4 where R is a lower alkanoyl, lower alkoxycarbonyl or benzoyl group; X is O, S, NH or NMe; Z is hydrogen, lower alkyl, benzhydryl, phenyl, indan-5-yl or a group of the formula -CH2OCO (lower alkyl), -CH (CH3) OCOO (lower alkyl) or **(See formula)** -CH2OCH2COOH, -CH2OCH2COO (lower alkyl), -CH2OCH2CONR2R3 wherein R2 and R3 are, independently, hydrogen or lower alkyl, or -CONR2R3 where R2 and R3 are defined as above; and its pharmaceutically acceptable salts; characterized in that (A) a 7-amino-3-heterocyclylthiomethyl- Δ 3-cephem derivative of the formula is reacted: **(See formula)** where X, R1 and z are defined as above, with an acylating agent of formula: **(See formula)** where R is defined as above and Y1 is a protected amino or hydroxyl group or a group of formula -OR4 where R4 is defined as above, or with its functional equivalent as acylating agent, followed by removal of the protecting group from Y1, protecting, if necessary, any free carboxyl group in (II) before the reaction, deprotecting itself after the reaction; or: (B), to prepare compounds of formula (I) in which Y is OH or NH2 and Z is H, a cephalosporin derivative of formula is reacted: **(See formula)** where R is defined as above, Y2 is OH, NH or a protected amino or hydroxyl group and R6 is a good leaving group, with a heterocyclic thiol of formula: **(See formula)** wherein R1 and X are defined as above, or with an ammonium or metal salt thereof, followed, if necessary, by removal of any protecting group from Y2; said processes (A) and (b) being optionally followed by: (i) conversion of a compound of formula (i) into a pharmaceutically acceptable acid addition or metal salt by reaction with a suitable acid or metal compound; or (ii) conversion of a compound of formula (I) in which Z is hydrogen, or an alkali metal salt thereof, into a compound of formula (I) in which Z is defined as above except hydrogen, by esterification, by protecting, if necessary, before the reaction, any free hydroxyl or amino group in Y and any free carboxyl group in R, and deprotecting itself after the reaction. (Machine-translation by Google Translate, not legally binding)
ES76446353A 1975-03-27 1976-03-25 Production of cephalosporin derivative Expired ES446353A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB7512813A GB1542397A (en) 1975-03-27 1975-03-27 Cephem compounds
GB4393575 1975-10-24

Publications (1)

Publication Number Publication Date
ES446353A1 true ES446353A1 (en) 1977-11-16

Family

ID=26249284

Family Applications (1)

Application Number Title Priority Date Filing Date
ES76446353A Expired ES446353A1 (en) 1975-03-27 1976-03-25 Production of cephalosporin derivative

Country Status (15)

Country Link
JP (1) JPS51138694A (en)
AU (1) AU1244276A (en)
DD (1) DD124601A5 (en)
DE (1) DE2612760A1 (en)
DK (1) DK132876A (en)
ES (1) ES446353A1 (en)
FI (1) FI760793A (en)
FR (1) FR2305186A1 (en)
IE (1) IE43541B1 (en)
IL (1) IL49183A0 (en)
LU (1) LU74651A1 (en)
NL (1) NL7603116A (en)
NO (1) NO761052L (en)
PT (1) PT64951B (en)
SE (1) SE7603699L (en)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA999574A (en) * 1972-06-14 1976-11-09 Smith Kline And French Canada Ltd. 7-hydroxyhalophenylacetamido-3-h heterocyclicthiomethyl cephalosporins
NL7401361A (en) * 1973-01-31 1974-08-02
US3989694A (en) * 1974-12-27 1976-11-02 Smithkline Corporation 7-Acyl-3-(substituted triazolyl thiomethyl)cephalosporins

Also Published As

Publication number Publication date
PT64951A (en) 1976-04-01
LU74651A1 (en) 1977-10-10
DK132876A (en) 1976-09-28
DD124601A5 (en) 1977-03-02
IE43541L (en) 1976-09-27
DE2612760A1 (en) 1976-10-07
NL7603116A (en) 1976-09-29
JPS51138694A (en) 1976-11-30
IL49183A0 (en) 1976-05-31
FI760793A (en) 1976-09-28
NO761052L (en) 1976-09-28
FR2305186A1 (en) 1976-10-22
PT64951B (en) 1977-08-26
FR2305186B1 (en) 1980-07-04
IE43541B1 (en) 1981-03-25
SE7603699L (en) 1976-09-28
AU1244276A (en) 1977-10-06

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