ECSP941095A - A PROCEDURE FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS - Google Patents

A PROCEDURE FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS

Info

Publication number
ECSP941095A
ECSP941095A ECSP941095A ECSP941095A EC SP941095 A ECSP941095 A EC SP941095A EC SP941095 A ECSP941095 A EC SP941095A EC SP941095 A ECSP941095 A EC SP941095A
Authority
EC
Ecuador
Prior art keywords
group
compound
formula
toxic
graph
Prior art date
Application number
Other languages
Spanish (es)
Inventor
Cynthia Hilda O'callaghan
Hubert David George Livermore
Christopher Earle Newall
Original Assignee
Glaxo Group Ltd
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 Glaxo Group Ltd filed Critical Glaxo Group Ltd
Publication of ECSP941095A publication Critical patent/ECSP941095A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by 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, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

Un procedimiento para la preparación de antibióticos de cefalosporinas de la fórmula general (gráfico), (en que Ra y Rb, pueden ser iguales o diferentes, representan cada uno un grupo alcohilo de 1 a 4 átomos de carbono o Ra y Rb juntamente con el átomo de carbono al que están unidos, 20 forman un grupo cicloalcohilideno de 3 a 7 átomos de carbono; y R4 representa hidrógeno o un grupo 3- o 4 carbamoilo) y sales no tóxicas y ésteres metabólicamente inestables no tóxicos de los mismo, caracterizados porque se acila un compuesto de fórmula (gráfico), (en que B es S ó S o; R4 representa hidrógeno o un grupo 3 ó 4-carbomoilo; y la linea de puntos que une las posiciones 2,3 y 4 indica que el compuesto es un compuesto de cef-2-em 10 o de cef-3-em), o una sal o derivado N-sílisico del mismo o un correspondiente compuesto que tiene un grupo de fórmula -COOR5 en la posición 4 (en donde R5 es un átomo de hidrógeno o un grupo bloqueador de hidroxilo) y que tiene un anión asociado a, con ácido de fórmula (gráfico), (en que Ra y Rb son como antes se defienen; R6 representa un grupo bloqueador de carboxilo; y R7 es un grupo amino o bien amino protegido), o cin un agente acilante correspondiente a éste; después de ello, si es necesario y/o 5 se desea en cada caso, se lleva a cabo cualquiera de las siguientes reacciones en cualquier sucesión apropiada: i) conversión de un isómero en el deseado isómero 3. ii) reducción de un compuesto en que B es para formar un compuesto en que B es S, iii) conversión de un grupo 10 carboxilo en una sal no tóxica o una función éster metabólicamente inestable no tóxica; y iv) eliminación de caulquiera grupos bloqueadores de carboxilo y/o protectores de N.A procedure for the preparation of cephalosporin antibiotics of the general formula (graph), (in which Ra and Rb, may be the same or different, each represent an alcohol group of 1 to 4 carbon atoms or Ra and Rb together with the carbon atom to which they are attached, 20 form a cycloalcohilidene group of 3 to 7 carbon atoms; and R4 represents hydrogen or a 3- or 4 carbamoyl group) and non-toxic salts and metabolically unstable non-toxic esters thereof, characterized in that a compound of formula (graph) is acylated, (in which B is S or S or; R4 represents hydrogen or a 3 or 4-carbomoyl group; and the dotted line joining positions 2,3 and 4 indicates that the compound is a compound of cef-2-em 10 or cef-3-em), or a N-sylisic salt or derivative thereof or a corresponding compound having a group of formula -COOR5 at position 4 (wherein R5 is a hydrogen atom or a hydroxyl blocking group) and having an as anion ociated to, with acid of formula (graph), (in which Ra and Rb are as before are defended; R6 represents a carboxyl blocking group; and R7 is an amino or protected amino group), or an acylating agent corresponding thereto; thereafter, if necessary and / or desired in each case, any of the following reactions are carried out in any appropriate sequence: i) conversion of an isomer to the desired 3-isomer. ii) reduction of a compound in that B is to form a compound in which B is S, iii) conversion of a carboxyl group into a non-toxic salt or a non-toxic metabolically unstable ester function; and iv) removal of any carboxyl-blocking and / or N-protecting groups.

ECSP941095 1978-05-26 1994-05-26 A PROCEDURE FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS ECSP941095A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2291378 1978-05-26

Publications (1)

Publication Number Publication Date
ECSP941095A true ECSP941095A (en) 1995-01-16

Family

ID=10187096

Family Applications (1)

Application Number Title Priority Date Filing Date
ECSP941095 ECSP941095A (en) 1978-05-26 1994-05-26 A PROCEDURE FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS

Country Status (2)

Country Link
AT (1) AT366698B (en)
EC (1) ECSP941095A (en)

Also Published As

Publication number Publication date
AT366698B (en) 1982-04-26
ATA383579A (en) 1981-09-15

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