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CRYSTALLINE FORM OF 4"-(PENTYLOXY)-[1, 1':4', 1''-TERPHENYL]-4-CARBOXYLIC ACID 2, 4-DINITROPHENYL ESTER.

IP.com Disclosure Number: IPCOM000185223D
Publication Date: 2009-Jul-16
Document File: 4 page(s) / 80K

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The IP.com Prior Art Database

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CRYSTALLINE FORM OF 4"-(PENTYLOXY)-[1, 1':4', 1''-TERPHENYL]-4- CARBOXYLIC ACID 2, 4-DINITROPHENYL ESTER.

4''-(pentyloxy)-[1, 1':4', 1''-Terphenyl]-4-carboxylic acid 2, 4-dinitrophenyl ester ("DNP- CPOT) of the following chemical structure:

O

O

  C30H26N2O7 Exact Mass: 526,17

Mol. Wt.: 526,54 ,

is an intermediate of synthesis of 1-((4R, 5R)-4, 5-Dihydroxy-N2-{[4"-(pentyloxy) (1, 1':4', 1"-terphenyl)-4-yl] carbonyl}-L-ornithine)-echinocandin B ("ADF") of the following chemical structure:

    which 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.

ADF is marketed under the trade name Ecalta (EU) and Eraxis (US) by Pfizer.Crystalline form of DNP-CPOT is described herein below.

DNP-CPOT crystalline form

O

O2N

NO2

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    The crystalline form of DNP-CPOT is characterized by data selected from a group consisting of: a powder XRD pattern having peaks at about 2.3, 4.3, 5.5, 6.4, 8.5, 9.7,
11.8, 12.8, 13.9, 14.9, 16.0, 18.1, 18.9, 19.6, 20.5, 22.5, 23.6, 25.7, 26.8, 27.9, 28.3 and
31.2 ± 0.2 degrees two-theta, and a PXRD pattern as depicted in Figure 1.

Figure 1: A PXRD pattern of DNP-CPOT crystalline form.

    The crystalline form of DNP-CPOT can be further characterized by data selected from a group consisting of:...