Intermediate cefdinir salts

• US 20060111566A1
• Filed: 09/26/2003
• Published: 05/25/2006
• Est. Priority Date: 10/01/2002
• Status: Active Grant

• Current Assignee: Antibiotice SA
• Original Assignee: Antibiotice SA
• Inventors: Alpegiani, Marco, Cabri, Walter, Pozzi, Giovanni, Martinez Gomez, Patricio
• Granted Patent: US 7,405,294 B2
• Time in Patent Office: Days
• US Class Current: 540/222
• CPC Class Codes: C07D 501/00 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
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

Disclosed are salts of the general formula (I) wherein R₁, R₂ and as defined in the description and a process for the preparation thereof. These salts are useful intermediates for the preparation of cefdinir.

Claims

1. Salts of formula (I)

2. Salts as claimed in claim 1 wherein R₁ is a formyl, tert-butoxycarbonyl, p-methoxybenzyloxycarbonyl, or trityl group.

3. Salts as claimed in claim 1 wherein R₂ is a tert-butyl, p-methoxybenzyl, 3,4-dimethoxybenzyl, benzhydryl, bis(p-methoxyphenyl)methyl and trityl group.

4. Salts as claimed in claim 1 wherein R₁ is hydrogen and R₂ is trityl.

5. Salts as claimed in claim 1 in which B is a primary amine selected from cyclohexylamine, 2-ethylhexylamine, benzylamine, α

-methylbenzylamine and tert-octylamine.

6. Salts as claimed in claim 1 in which B is a secondary amine selected from diethylamine, morpholine, dicyclohexylamine, N,N-methylbenzylamine or N, N¹-dibenzylethylenediamine.

7. Salts as claimed in claim 6 wherein B is dicyclohexylamine.

8. Salts as claimed in claim 1 wherein B is a tertiary amine selected from triethylamine, tributylamine, triisooctylamine, ethyldiisopropylamine, N-methylmorpholine, pyridine, 2,6-lutidine or quinoline.

9. Salts as claimed in claim 1 wherein B is 1,1,3,3-tetramethylguanidine.

10. Salts as claimed in claim 1 wherein B is 1,5-diazabicylclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU).

12. Use of salts as claimed in claim 1 for the preparation of cefdinir.

11. Salts of formula (Ia)