ECSP941095A - A PROCEDURE FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS - Google Patents
A PROCEDURE FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICSInfo
- 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
Links
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 239000003242 anti bacterial agent Substances 0.000 title abstract 2
- 229940088710 antibiotic agent Drugs 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- 150000001780 cephalosporins Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- 231100000252 nontoxic Toxicity 0.000 abstract 4
- 230000003000 nontoxic effect Effects 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 230000000903 blocking effect Effects 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
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.
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) |
-
1979
- 1979-05-25 AT AT383579A patent/AT366698B/en not_active IP Right Cessation
-
1994
- 1994-05-26 EC ECSP941095 patent/ECSP941095A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATA383579A (en) | 1981-09-15 |
| AT366698B (en) | 1982-04-26 |
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