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SOLID STATE FORMS OF 1-(4-METHOXYPHENYL)-7-OXO-6-[4-(2- OXOPIPERIDIN-1-YL)PHENYL]-4,5,6,7-TETRAHYDRO-1H-PYRAZOLO[3,4- C]PYRIDINE-3-CARBOXAMIDE

IP.com Disclosure Number: IPCOM000227611D
Publication Date: 2013-May-09
Document File: 5 page(s) / 39K

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   SOLID STATE FORMS OF 1-(4-METHOXYPHENYL)-7-OXO-6-[4-(2- OXOPIPERIDIN-1-YL)PHENYL]-4,5,6,7-TETRAHYDRO-1H-PYRAZOLO[3,4-


C]PYRIDINE-3-CARBOXAMIDE

1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H- pyrazolo[3,4-c]pyridine-3-carboxamide, has the following chemical structure:

NH2

O

N

Provided are process for the preparation solid state forms of 1-(4-methoxyphenyl)-7- oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine- 3-carboxamide.

Example 1:To a 25 mL round bottom flask equipped with a stirring magnet 1-(4- methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H- pyrazolo[3,4-c]pyridine-3-carboxamide (3 g) was dissolved in NMP (30 mL) at 55°C. The NMP solution was cooled to RT and then added dropwise over 30 min to MeOH (15mL), at 50°C in a 100 ml reactor. The mixture was cooled to -10oC over 3h and stirred overnight at -10oC. The mixture was filtered and washed with MeOH. The product 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7- tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide was analyzed by XRPD to give the following pattern:

O

N N O

N

O


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g

[ ]

[ g]

6000

Si

4000

2000

0


2.0


6.0


10.0


14.0


18.0


22.0


26.0


30.0


34.0


38.0

Figure 1

Main XRD peaks are: 6.8, 8.5, 9.0, 10.5, 12.4, 12.9, 13.8, 15.1, 16.3, 17.1, 17.8, 18.4,


18.9, 19.1, 19.4, 20.5, 21.2, 21.6, 22.2, 22.6, 23.0, 23.6, 23.9 24.1, 24.8, 28.1, 29.2 and


30.0 ± 0.2 degrees 2-theta. The peak at about 28.5° is attributed to silicon powder added as an internal standard.

Example 2: The resulting product of Example 1 was dried in oven vacuum at 70oC, The product 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7- tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide was analyzed by XRPD.

The XRPD pattern is presented in the following representative X-ray diffractogram):

Range: 2.000 40.000 Cont. Scan Rate: 3.000 [ /min]

Horz. Scale Unit: [deg]

6000

Si

4000

2000

0


2.0


6.0


10.0


14.0


18.0


22.0


26.0


30.0


34.0


38.0

-=Figure 2

Main XRD peaks are: 6.9, 9.0, 10.6, 11.9, 12.9, 13.8, 15.1, 16.3, 17.2, 17.5, 18.4, 19.0,


19.1, 19.5, 20.5, 21.2, 21.7, 22.2, 22.7, 23.0, 24.0, 24.6, 24.8, 25.3, 25.5, 26.4, 27.7,


28.2, 28.5, 29.2, 30.7, 31.1, 32.8, 33.5, 35.1, 35.9 and 37.2 ± 0.2 degrees 2-theta. The peak at about 28.5° is attributed to silicon powder added as an internal standard.


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Example 3: To a 25 mL round bottom flask equipped with a stirring magnet 1-(4- methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H- pyrazolo[3,4-c]pyridine-3-carboxamide (3 g) was dissolved in NMP (30 mL) at 55°C. The NMP solution was cooled to RT and then MeOH (15 ml) was added dropwise over 30 min to the NMP solution. The mixture was stirred at 20oC over night. The mixture was filtered and washed with MeOH. The product 1-(4-methoxyphenyl)-7-oxo-6-(4-(2- oxopiperidin-1-yl...