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Isolation 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: IPCOM000192087D
Publication Date: 2010-Jan-20
Document File: 3 page(s) / 113K

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Isolation 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 ADF) of the following chemical structure:

    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.

Amorphous ADF was isolated using spray dry technique as described herein

below.

Fig.1 PXRD pattern of amorphous ADF

Intensity(count

1600

900

400

100

0

5 10 15 20 25 30 35

2Theta (°)

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Fig.2 DSC thermogram of amorphous ADF

63.02°C

In

s

t

r

u

m

e

n

t

:

DS

C

Q10

0

0

V9.

8

B

u

ild

29

6

0.2

0.0

Method Log:
1: Equilibrate at 20.00°C
2: Ramp 10.00°C/min to 250.00°C 3: End of method

Hermetic, aluminum, closed pan with hole was used

-0.2

Heat Flow (W/g)

-0.4

-0.6

-0.8

179.95°C

-1.0

20 70 120 170 220

Temperature (°C)

Exo Down Universal V4.2E TA Instruments

Examples:

Example 1

170 ml of ADF solution in ethanol (about 5 g/L, a...