Claims
- 1. Tert-octylamine salt of 7-[2-(2-aminothiazol4-yl)-2-((aryl-or alk)-oxycarbonylmethoxyimino)acetamido]-3-vinyl-3-ceph-3-em-4-carboxylic acid of formula wherein the amine group attached to the thiazolyl ring is free or protected, and wherein the tert-octylamine has the formula: and wherein R denotes alkyl or aryl.
- 2. The tert-octylamine salt of a compound of formula V according to claim 1 wherein R is methyl.
- 3. A process for the production of a tert-octylamine salt of a compound of formula wherein the amine group attached to the thiazolyl ring is free or protected, and wherein the tert-octylamine has the formula and wherein R denotes alkyl or aryl, comprising the steps(I) reacting a compound of formula III in free form or in the form of a salt, with an activated ester of 2-(2-amino-4-thiazolyl)-(Z)-2-((aryl- or alk)-oxycarbonyl)-methoxyimino)acetic acid, to obtain a compound of formula V in free form, or in the form of a salt and converting a compound of formula V in the form of a salt into a compound of formula V in a free form, and (II) reacting a compound of formula V in free form obtained in step (i) with tert. octylamine.
- 4. A process according to claim 3, wherein an activated ester of 2-(2-amino-4-thiazolyl)-(Z)-2-((aryl-or alk)-oxycarbonyl)-methoxyimino)acetic acid is used without isolation from its production process.
- 5. A process for the production of a tert-octylamine salt of a compound of formula wherein the amine group attached to the thiazolyl ring is free or protected, and wherein the tert-octylamine the tile formula and wherein R denotes alkyl or aryl, comprising the steps(I) acylating a compound of formula III in free form or salt form, with an activated form of 4-halo-2-[((aryl- or alk)oxycarbonyl)methoxyimino]-3-oxo-butyric acid, to obtain a 7-(2-(halomethylcarbonyl)-2-((Z)(aryl-or alk)-oxycarbonyl)methoxyimino)-acetamido)-3-vinyl-ceph-3-em-4-carboxylic acid in free form, wherein the carboxylic acid group in position 4 of the ring system is unprotected, or in the form of a salt, and (II) reacting the 7-(2-(halomethylcarbonyl)-2-((Z)(aryl-or alk)-oxycarbonyl)methoxyimino)-acetamido)-3-vinyl-ceph-3-em-4-carboxylic acid in free form, wherein the carboxylic acid group in position 4 of the ring system is unprotected, or in the form of a salt, as obtained in step (i), with thiourea to obtain a compound of formula V in free form, or in the form of a salt and converting a salt of a compound of formula V into a free form of a compound of formula V, and (III) reacting a compound of formula V obtained in step (ii) with tert.octylamine.
- 6. The process according to claim 5 where halo is chloro.
- 7. A process according to claim 5, wherein in step (i) 4-halo-3-oxo-2-(aryl-or alk)-oxycarbonyl-methoxyimino butyric acid in an activated form is used without isolation from its activation production process.
- 8. A process for the production of a tert-octylamine salt of a compound of formula wherein the amine group attached to the thiazolyl ring is free or protected, and wherein the tert-octylamine has the formula: and wherein R denote, alkyl or aryl, comprising the steps(1) reacting a compound of formula III in protected form, with an activated ester of 2-(2-amino-4-thiazolyl)-(Z)-2-((aryl- or alk)-oxycarbonyl)-methoxyimino)acetic acid, to obtain a compound of formula V, in protected form, and splitting off protecting groups, and (ii) reacting a compound of formula V in free form obtained in step (i) with tert. octylamine as defined above.
- 9. A process according to claim 8, wherein an activated ester of 2-(2-amino-4-thiazolyl)-(Z)-2-((aryl-or alk)-oxycarbonyl)-methoxyimino)acetic acid is used without isolation from its production process.
- 10. A process for the production of a tert-octylamine salt of a compound of formula wherein the amine group attached to the thiazolyl ring is free or protected, and wherein the tert-octylamine has the formula and wherein R denotes alkyl or aryl, comprising the steps(i) acylating a compound of formula III in protected form, with an activated form of 4-halo-2-[((aryl- or alk)oxycarbonyl)methoxyimino]-3-oxo-butyric acid, to obtain a 7-(2-(halomethylcarbonyl)-2-((Z)((aryl-or alk)-oxycarbonyl)methoxyimino)-acetamido)-3-vinyl-ceph-3-em-4-carboxylic acid, wherein the carboxylic acid group in position 4 of the ring system is protected, and (ii) reacting the 7-(2-(halomethylcarbonyl)-2-((Z)((aryl-or alk)-oxycarbonyl)methoxyimino)-acetamido)-3-vinyl-ceph-3-em-4-carboxylic acid wherein the carboxylic acid group in position 4 of the ring system is protected as obtained in step (i), with thiourea to obtain a compound of formula V as defined in claim 1wherein the carboxylic acid group in position 4 is protected, and splitting off the protecting group, and(iii) reacting a compound of formula V obtained in step (ii) with tert.octylamine.
- 11. A process according to claim 10, wherein in step (i) 4-halo-3-oxo-2-(aryl -or alk)-oxycarbonyl-methoxyimino butyric acid in an activated form is used without isolation from its activation production process.
- 12. The process according to claim 10 wherein halo is chloro.
- 13. A process for the preparation of a product which is the tert-octylamine salt of a compound of formula V: wherein the amine group attached to the thiazolyl ring is free or protected, and wherein the tert-octylamine has the formula: and wherein R denotes alkyl or aryl, comprising the steps(i) reacting a compound of formula V, above, (ii) with tert-octylamine as defined above, in solution with an organic solvent; then (iii) followed by addition of a non-solvent for the product to crystallize the product.
Priority Claims (1)
Number |
Date |
Country |
Kind |
575/98 |
Apr 1998 |
AT |
|
Parent Case Info
This is a continuation of U.S. application U.S. Ser. No. 09/669,645, filed Sep. 26, 2000, now abandoned; which in turn a continuation of International Application No. PCT/EP99/02222, filed Mar. 31, 1999.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4816582 |
Furlenmeier et al. |
Mar 1989 |
A |
5359057 |
Furlenmeier et al. |
Oct 1994 |
A |
Foreign Referenced Citations (6)
Number |
Date |
Country |
0 658 558 |
Jun 1995 |
EP |
0 831 093 |
Mar 1998 |
EP |
0 093 376 |
Apr 1999 |
EP |
WO 9707121 |
Feb 1997 |
WO |
WO 9806723 |
Feb 1998 |
WO |
WO 9831685 |
Jul 1998 |
WO |
Non-Patent Literature Citations (2)
Entry |
Yamanaka et al., Studies on beta-lactam antibiotics, Synthesis and biologigal activity of a new orally active cephalosporing, cefixime (FK027), The Journal of Antibiotics, pp 1738-1751 (1985). |
International Search Report. |
Continuations (2)
|
Number |
Date |
Country |
Parent |
09/669645 |
Sep 2000 |
US |
Child |
10/261748 |
|
US |
Parent |
PCT/EP99/02222 |
Mar 1999 |
US |
Child |
09/669645 |
|
US |