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Mesylate salt of (3Z)-2,3-dihydro-3-[[[4-[methyl[2-(4-methyl-1-piperazinyl) acetyl]amino]phenyl]amino]phenylmethylene]-2-oxo-1H-indole-6-carboxylic acid methyl ester

IP.com Disclosure Number: IPCOM000245261D
Publication Date: 2016-Feb-23
Document File: 3 page(s) / 83K

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The IP.com Prior Art Database

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Mesylate salt of (3Z)-2,3-dihydro-3-[[[4-[methyl[2-(4-methyl-1-piperazinyl) acetyl]amino]phenyl]amino]phenylmethylene]-2-oxo-1H-indole-6-carboxylic acid methyl ester

(3Z)-2,3-dihydro-3-[[[4-[methyl[2-(4-methyl-1-piperazinyl)acetyl]amino]phenyl]aminophenyl methylene]-2-oxo-1H-indole-6-carboxylic acid methyl ester is referred to herein as Compound 1. Enclosed herein after are crystalline forms of the mesylate salt of compound 1.

Crystalline form 1:

    Main PXRD peaks: 9.4, 12.8, 13.6, 15.5, 17.3, 19.2, 19.6, 20.5, 20.8 and 21.4 degrees 2- theta ± 0.2 degrees 2- theta

Example 1: preparation of crystalline form 1:

    A suspension of Compound 1 (free base, 5.00 g) in methanol (35 mL) was heated to 65 °C. 70% aqueous methane sulfonic acid (1.3 g) was added and the resulting solution was cooled to 50 °C. Isopropyl alcohol (40 mL) was added drop-wise in about 30 minutes. The obtained suspension was cooled to 0 °C and stirred for one hour at the same temperature. The product was isolated by filtration and dried at 50 °C until constant weight. Compound 1 mesylate was obtained as a bright yellow solid
(5.6 g, 96 % yield,99.79% purity). The product was analyzed by PXRD.

Intensity (counts)

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10 15 20 25 30 35

2Theta (°)


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Crystalline form 2:

Hemihydrate form of compound 1 mesylate salt is described by unit cell parameters in US 2009/0318471 A1.

Single crystal analysis of crystalline form 2 of compound 1 meslyate gave corresponding unit...