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PROCESSES FOR PREPARING ERTAPENEM SODIUM

IP.com Disclosure Number: IPCOM000228661D
Publication Date: 2013-Jun-27
Document File: 12 page(s) / 70K

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Abstract

A stable ertapenem monosodium of Formula Ia, which can be stored at a temperature of 2°C to 8°C is provided.

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PROCESSES FOR PREPARING ERTAPENEM SODIUM

Abstract

A stable ertapenem monosodium of Formula Ia, which can be stored at a temperature of 2°C to 8°C is provided.


            Ertapenem sodium is a carbapenem antibiotic, which is chemically a monosodium (Formula Ia) or a di-sodium salt of 4R-[3(3S*,5S*),4α,5β,6β(R*)]-3-[[5-[[(3-carboxyphenyl)
amino]carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo
[3.2.0]hept-2-ene-2-carboxylic acid of Formula I.

FORMULA I

FORMULA Ia

            The term “stable ertapenem monosodium” of Formula Ia refers to ertapenem monosodium which can be stored at a temperature of 2°C to 8°C.  It has been formulated into a pharmaceutical composition comprising the compound of Formula II, or its salts.

FORMULA II

            Stable ertapenem monosodium having a water content of 8% (w/w) or less and an ethanol content of 1% to 7%, which can be stored at a temperature of 2°C to 8°C, is provided.  Also provided is a stable ertapenem monosodium having a water content of 9% (w/w) or less and an acetone content of 1% to 7%, which can also be stored at a temperature of 2°C to 8°C. 

            Stable ertapenem monosodium having a water content of 8% (w/w) or less and an ethanol content of 1% to 7% can be prepared by a process that comprises the following steps:

a)            treating the aqueous solution of ertapenem sodium with an alcoholic solvent;

b)            isolating ertapenem monosodium from the solution of step a); and

c)            washing ertapenem monosodium obtained from step b) with absolute ethanol to obtain ertapenem monosodium having a water content of 8% (w/w) or less and an ethanol content of 1% to 7%.

            The stable ertapenem monosodium having a water content of 8% (w/w) or less and an ethanol content of 1% (w/w) to 7% (w/w) may be further converted into a pharmaceutical composition comprising the compound of Formula II or its salts by the methods known in the prior art.

            Ertapenem monosodium can be prepared by a process which comprises the following steps:

a)            treating an aqueous solution of ertapenem sodium with an alcoholic solvent at a temperature of -2°C to -6°C;

b)            isolating ertapenem monosodium from the solution of step a); and

c)            washing ertapenem monosodium obtained from step b) with absolute ethanol to obtain ertapenem monosodium.

            Stable ertapenem monosodium having a water content of 9% (w/w) or less and an acetone content of 1% to 7%, can be prepared by a process which comprises the following steps:

a)            treating an aqueous solution of ertapenem sodium with an alcoholic solvent;

b)            isolating ertapenem monosodium from the solution of step a); and

c)            washing ertapenem monosodium obtained from step b) with acetone to obtain ertapenem monosodium having a water content of 9% (w/w) or less and an ethanol content of 1% to 7%.

For all three processes described above, the following apply:

Ertapen...