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US 9,163,034 B2Granted
Crystalline (6R,7R)-7-{2-(5-amino-[1,2,4] thiadiazol-3-yl)-2-[(Z)-trityloxyimino]-acetylamino}-3-[(R)-1′-tert-butoxycarbonyl-2-oxo-[1,3′]bipyrrolidinyl-(3E)-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester; its manufacture and use
AssigneeBasilea Pharmaceutica AG
InventorsMarco Alpegiani, Jr., Walter Cabri, Markus Heubes, Davide Longoni, Michael Schleimer
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Abstract
A solid DMSO solvate of a compound of formula (I) is described, which is a useful intermediate for preparing the broad spectrum antibiotics Ceftobiprole and Ceftobiprole Medocaril.
Claims11
A process for the manufacture of a purified form of a compound of formula (I):
- from a raw form of said compound, comprising the steps of:
- converting said raw compound of formula (I) into a solid DMSO solvate;
- isolating said DMSO solvate;
- re-dissolving said isolated DMSO solvate in methylene chloride in which said compound of formula (I) precipitates;
- and
- isolating said precipitated purified compound of formula (I).
3 more elements
A process for the manufacture of a solid DMSO solvate of the compound of formula (I)
- comprising the steps of:
- suspending a raw compound of formula (I) in ethyl acetate;
- adding DMSO to said suspension in an amount sufficient to dissolve the compound of formula (I) into a DMSO solvate;
- separating said DMSO solvate of the compound of formula (I) from the liquid phase;
- and
- processing said DMSO solvate without previously drying it.
3 more elements
A process for the manufacture of a solid DMSO solvate of the compound of formula (I):
- comprising the steps of:
- suspending raw compound of formula (I) in ethyl acetate;
- adding DMSO to said suspension in an amount sufficient to dissolve the compound of formula (I) to form a DMSO solvate;
- and
- separating said DMSO solvate from the liquid phase, wherein the raw compound of formula (I) is manufactured by reacting (1′-tert-butoxycarbonyl-2-oxo-[1,3′]-(R)-bipyrrolidinyl-3-(R,S)-yl)-triphenyl-phosphonium bromide with 7-[2-(5-amino-[1,2,4]thia-diazol-3-yl)-2-trityloxyimino-acetylamino]-3-formyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester in a mixture of methylene chloride/toluene/THF in presence of t-C4H9OK.
2 more elements
Dependencies are inferred from the claim text.