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Crystalline form of 6-(4-aminophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide and salts thereof

IP.com Disclosure Number: IPCOM000236860D
Publication Date: 2014-May-20
Document File: 2 page(s) / 74K

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Crystalline form of 6-(4-aminophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-

tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide and salts thereof

Disclosed herein after is crystalline Form J of 6-(4-aminophenyl)-1-(4- methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3- carboxamide ("compound I").

Figure 1: a powder XRD pattern of crystalline Form J of compound I:

CPS

Main XRD peaks of crystalline Form J of compound I are: 4.9, 7.0, 8.1, 8.5,
11.1, 11.4, 13.9, 14.3, 15.6, 16.0, 16.8, 18.9, 19.5, 21.0, 21.6, 23.1, 24.2, 24.7,
26.0, 26.7, 27.9, 28.1, 28.9 and 29.6 ± 0.2 degrees 2-theta.

X-Ray Power Diffraction:

The analysis was performed on ARL (SCINTAG) powder X-Ray diffractometer model X'TRA equipped with a solid state detector. Copper radiation of 1.5418 Å was used. Scanning parameters: range: 2-40 degrees two-theta; scan mode: continuous scan; step size: 0.05°.; and a rate of 3 deg/min.

Example:

Ethyl 1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-4,5,6,7-tetrahydro-1H- pyrazolo[3,4-c]pyridine-3-carboxylate (4 g), methanol (108 mL) and Pd/C (0.1
g) were charged in the reactor. The mixture was pressurized with hydrogen 3 bar and heated to reflux and stirred until reaction completion. Then the hydrogen was released and the mixture was filtrated and the cake was washed with methanol. The solution was cooled to 0-15°C and ammonia (13.6 g) was

degrees 2-theta


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added. The reactor was sealed and heated to 67-73°C. After reaction completion, t...