Process for the preparation of cefpodoxime proxetil

• US 20060009639A1
• Filed: 11/19/2003
• Published: 01/12/2006
• Est. Priority Date: 11/22/2002
• Status: Abandoned Application

• Current Assignee: Orchid Chemicals & Pharmaceuticals Limited (Orchid Pharma Ltd.)
• Original Assignee: Orchid Chemicals & Pharmaceuticals Limited (Orchid Pharma Ltd.)
• Inventors: Deshpande, Pandurang Balwant, Luthra, Parven Kumar, Deshpande, Pramod Narayan, Subramanian, Selvraj, Kamma, Ramakrishna, Das, Gautam Kumar
• Application Number:
  US10/535,923
• Publication Number:
  US 20060009639A1
• Time in Patent Office: Days
• US Class Current: 540/228
• 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

Abstract

An improved process for the preparation of cefpodoxime proxetil of the formula (I) the said process comprises reacting cefpodoxime acid with 1-haloethyl isopropyl carbonate of the formula (VI) where X represents halogen atom such as chlorine, bromine or iodine using a base such as tetramethylguanidine, di-isopropylethyl amine, 1,5-diazabicyclo(4.3.0)non-5-ene (DBN), 1,4-diazabicyclo[2.2.2]octane (DABCO) in the presence of a solvent at a temperature in the range of −30 ° C. to 30 ° C. to produce cefpodoxime proxetil of the formula (I) and isolating the pure cefpodoxime proxetil of the formula (I).

Claims

1. An improved process for the preparation of cefpodoxime proxetil of the formula (I)

2. The process as claimed in claim 1, wherein the solvent used in step (i) is selected from THF, dichloromethane, acetone, butan-2-one, acetonitrile, DMAc, DMF, DMSO, or a mixture thereof.

3. The process as claimed in claim 1, wherein the isolation in step (ii) is carried out by using water miscible solvent and water or an acid followed by basification.

4. The process as claimed in claim 3, wherein the water miscible solvent is selected from methanol, ethanol or iso-propanol.

5. The process as claimed in claim 3, wherein the acid is selected from hydrochloric acid or sulfuric acid.

6. The process as claimed in claim 3, wherein the base is selected from ammonia or triethyl amine.

8. The process as claimed in claim 1, wherein the compound of formula (I) obtained is a syn isomer.

9. The process as claimed in claim 1, wherein the compound of formula (I) obtained contains less percentage of Δ

³ isomer.

7. The process as claimed in claim i, wherein the compound of formula (I) obtained with reduced high molecular weight impurities.

10. An improved process for the preparation of pure cefpodoxime proxteil of formula (I) comprising purifiing the cefpodoxime proxetil using water miscible solvent and water or an acid followed by basification.

11. The process as claimed in claim 10, wherein the water miscible solvent is selected from methanol, ethanol or iso-propanol.

12. The process as claimed in claim 10, wherein the acid is selected from hydrochloric acid or sulfuric acid.

13. The process as claimed in claim 10, wherein the base is selected from ammonia or triethyl amine.

14. The process as claimed in claim 10, wherein the compound of formula (I) obtained with reduced high molecular weight impurities.