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US 2002/0160942 A1Published application
Echinocandin/carbohydrate complexes
AssigneeEli Lilly and Company
InventorsLarry Arnold Larew, Nathaniel Milton, James Lawrence Sabatowski, Kenneth Philip Moder
Life of this patent
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Abstract
A complex of an echinocandin compound with a carbohydrate is described having improved thermal stability and water solubility. A process for making the echinocandin/carbohydrate complex is also described as well as the use of the complex in pharmaceutical formulations and treatments of fungal infections.
Claims27
An echinocandin/carbohydrate complex comprising a carbohydrate and an echinocandin compound represented by the following structure:
- 8
- wherein:
- R is an alkyl group, an alkenyl group, an alkynyl group, an aryl group, heteroaryl group, or combinations thereof;
- R1, R2, R3, R6, R7, and R10 are independently hydroxy or hydrogen;
- R4 is hydrogen, methyl or —CH2C(O)NH2;
- R5 and R11 are independently methyl or hydrogen;
- R8 is —OH, —OSO3H, —OPO3H2, —OPO3HRa, or —OPO2HRa, where Ra is hydroxy, C1-C6 alkyl, C1-C6 alkoxy, phenyl, phenoxy, p-halophenyl, p-halophenoxy, p-nitrophenyl, p-nitrophenoxy, benzyl, benzyloxy, p-halobenzyl, p-halobenzyloxy, p-nitrobenzyl, or p-nitrobenzyloxy;
- R9 is —H, —OH, or —OSO3H;
- and pharmaceutically acceptable salts or hydrates thereof.
6 more elements
A Echinocandin/carbohydrate complex prepared by the steps of:
- (a) providing an echinocandin compound represented by the following structure
- 11
- wherein
- R is an alkyl group, an alkenyl group, an alkynyl group, an aryl group, heteroaryl group, or combinations thereof,
- R1, R2, R3, R6, R7, and R10 are independently hydroxy or hydrogen,
- R4 is hydrogen, methyl or —CH2C(O)NH2,
- R5 and R11 are independently methyl or hydrogen,
- R8 is —OH, —OSO3H, —OPO3H2, —OPO3HR8 a, or —OPO2HRa, where Ra is hydroxy, C1-C6 alkyl, C1-C6 alkoxy, phenyl, phenoxy, p-halophenyl, p-halophenoxy, p-nitrophenyl, p-nitrophenoxy, benzyl, benzyloxy, p-halobenzyl, p-halobenzyloxy, p-nitrobenzyl, or p-nitrobenzyloxy;
- R9 is —H, —OH, or —OSO3H, and pharmaceutically acceptable salts or hydrates thereof;
- (b) mixing together said echinocandin compound of step (a) to a carbohydrate in a solvent to form a mixture;
- (c) heating said mixture to solubilize said echinocandin compound and to solubilize or disperse said carbohydrate;
- (d) allowing said mixture to cool to produce said echinocandin/carbohydrate complex;
- and
- (e) isolating said echinocandin/carbohydrate complex.
11 more elements
Dependencies are inferred from the claim text.