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Purification of 1-((4R,5R)-4,5-dihydroxy-N2-{[4"-(pentyloxy)(1,1':4',1"-terphenyl)-4-yl]carbonyl}-L-ornithine)-echinocandin B

IP.com Disclosure Number: IPCOM000206432D
Publication Date: 2011-Apr-26
Document File: 2 page(s) / 58K

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Purification of 1-((4R,5R)-4,5-dihydroxy-N2-{[4"-(pentyloxy)(1,1':4',1"- terphenyl)-4-yl]carbonyl}-L-ornithine)-echinocandin B

1-((4R,5R)-4,5-Dihydroxy-N2-{[4"-(pentyloxy)(1,1':4',1"-terphenyl)-4-yl]carbonyl}- L-ornithine)-echinocandin B (referred as compound 1) of the following chemical structure:

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    is a semi-synthetic cyclic lipopeptide of the echinocandin B class, synthesized from Echinocandin B, a fermentation product of Aspergillus nidulans. It is an antifungal drug that inhibits the synthesis of β (1,3)-D-glucan, an essential component of fungal cell walls. It is indicated for the treatment of candidemia, esophageal candidiasis, and other forms of candida infections.

Compound 1 was purified using chromatography technique as described

herein below.

Gradient HPLC method

Column: C18 150 x 4.6 mm
Eluent: 0.01 V/V% TFA/Acetonitrile Flow rate: 1.5 ml/min
Run time: 50 min
Detection wavelength: 220 nm
Diluent: methanol

Example 1. Purification of Compound 1 by chromatography

Column was equilibrated with water-acetone-THF mixture.
30 g Compound 1 (96.1 A% pure by HPLC) was dissolved in 60 ml eluent, and loaded on column. Elution was carried out with water:acetone:THF mixture. Fractions


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were analyzed by HPLC. 16.23 g purified Compound 1 (99.07 A% pure by HPLC) was isolated from selected fractions, yield was 64.5 %.