US 7,459,550 B2Granted

Process for the preparation of Cefditoren

AssigneeOrchid Chemicals & Pharmaceuticals Limited

InventorsKumar Sahoo Prabhat, Anandam Vempali, Sivakumaran Sundaravadivelan, Nagesh Ganesh Praveen, Manikrao Waghdare Vittal, Balawant Deshpande Pandurang, Kumar Luthra Parven, Ramesh Sathe Pratik

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Abstract

The present invention relates to an improved process for the preparation of Cefditoren of formula (I), the said process comprising the steps of: i) converting the compound of formula (II) to a compound of the formula (III) using TPP and sodium iodide in the presence of THF, water, and base; ii) reacting the compound of formula (III) with 4-methyl-5-formyl-thiazole to produce a compound of formula (IV); iii) deesterifying the compound of the formula (IV) to yield compound of formula (V); iv) converting the compound of formula (V) to compound of formula (VI) in the presence of a base and solvent; v) converting the compound of formula (VI) into compound of formula (VII) by enzymatic hydrolysis; and vi) reacting compound of formula (VII) with compound of formula (VIII) in the presence of solvent and base to produce compound of formula (I).

Claims14

Dependent claims

A process for the preparation of Cefditoren of formula (I) or its ester or pharmaceutically acceptable salts there of

which comprising the steps of:
i) converting the compound of formula (II)
wherein R1 represents carboxy protecting group to a compound of the formula (III)
using triphenylphosphine and alkali iodide in the presence of aprotic solvent, water and base,
ii) reacting the compound of formula (III) with 4-methyl-5-formyl-thiazole in the presence of aprotic solvent, water and base to produce a compound of formula (IV)
wherein R1 is as defined above,
iii) deesterifying the carboxy protecting group of compound of the formula (IV) using an acid in the presence of solvent to yield compound of formula (V),
iv) converting the compound of formula (V) to compound of formula (VI)
wherein X represents a counter ion which forms a salt;
in the presence of a base and solvent,
v) converting the compound of formula (VI) into compound of formula (VII)
by enzymatic hydrolysis, and
vi) reacting compound of formula (VIII) with compound of formula (VII)
wherein Y is selected from halogen, and 2-mercaptobenzothiazole (MBT), and in the presence of solvent and in presence or absence of base to produce compound of formula (I).

11 more elements

Dependencies are inferred from the claim text.