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(s)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-n- Solid forms and preparations of (pyridin-2-yl)benzamide

A technology of benzamide and alkynoyl, which is applied in the direction of non-active ingredient medical preparations, active ingredient-containing medical preparations, anti-inflammatory agents, etc., and can solve the problem of serum immunoglobulin reduction and other problems

Active Publication Date: 2021-07-23
ACERTA PHARMA BV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This results in an almost complete absence of B lymphocytes, leading to a marked reduction in serum immunoglobulins of all classes

Method used

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  • (s)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-n- Solid forms and preparations of (pyridin-2-yl)benzamide
  • (s)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-n- Solid forms and preparations of (pyridin-2-yl)benzamide
  • (s)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-n- Solid forms and preparations of (pyridin-2-yl)benzamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0179] Example 1. Form I (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazine-1 -yl)-N-(pyridin-2-yl)benzamide (free base) anhydrous crystals

Embodiment 11

[0180] Example 1.1. Preparation of type I anhydrous crystals

[0181] Using amorphous (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl) -N-(pyridin-2-yl)benzamide was used as starting material for crystallization studies. The amorphous character of the batch was determined by PXRD. For cooling crystallization experiments, 25 mg of amorphous formula (1) was dissolved in 300 µL of solvent, heated to 60 °C at a rate of 5 °C / hour, held at this temperature for 1 hour, and then cooled to 5 °C at the same rate. For slurrying experiments, 25 mg of amorphous form (1) was suspended in 150 µL of solvent at 20°C for 3 days. All solids were isolated for PXRD analysis. When a clear solution was obtained, the solvent was evaporated under vacuum (200 mbar). The results are summarized in Table 1.

[0182]

[0183]

[0184]

[0185]

[0186] The results show that when solids are obtained, the amorphous form of formula (1) is obtained from most solvent...

Embodiment 12

[0191] Example 1.2. Physical characterization of type I anhydrous crystals

[0192] Various techniques are used, including: Transmission PXRD ( figure 1 ), Raman ( figure 2 ) and infrared spectroscopy ( image 3 ), NMR spectra of the solution state after Type I dissolution, TG-FTIR, differential scanning calorimetry (DSC), semi-quantitative solubility tests, and dynamic vapor adsorption (DVS; also known as gravity vapor adsorption or GVS), for passing The free base Form I of formula (1) produced from crystallization from acetone in the presence of methanol (referred to herein as sample PP502-P1) was characterized.

[0193] Transmission PXRD patterns of Type I were obtained using a Stoe Stadi P high-precision double-circle goniometer equipped with a Mythen1K detector and a Cu-Kα1 radiation source, operating under the following standard measurement conditions: Tube voltage: 40 kV, tube Current: 40 mA; Arc Ge monochromator; Step size: 0.02° 2θ; Pulse time (step time): 48 seco...

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Abstract

In some embodiments, the invention relates to (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrrolidinyl) crystalline solid forms of (azin-1-yl)-N-(pyridin-2-yl)benzamide, including polymorphs, hydrates and salt forms. In some embodiments, the present invention also relates to pharmaceutical compositions comprising said crystalline solid forms, and methods of treating disorders or diseases by administering to a subject pharmaceutical compositions comprising said forms, including pharmaceutical combinations that overcome the effects of acid reducing agents things and methods. Formula (I)

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS [0002] This application, which is an international application, claims the benefit of US Provisional Application 62 / 188,468, filed July 2, 2015, and US Provisional Application 62 / 271,708, filed December 28, 2015, each of which is incorporated herein by reference in its entirety. . [0003] Field of Invention [0004] In some embodiments, the present invention relates to (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyridine Crystalline Form I of oxazin-1-yl)-N-(pyridin-2-yl)benzamide. In other embodiments, the present invention relates to pharmaceutical compositions comprising Form I, including pharmaceutical compositions that overcome the effects of acid reducing agents, and methods for treating cancer or other disorders by administering said pharmaceutical compositions to a subject method. In some embodiments, the present invention relates to (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/4985A61P35/00
CPCC07D487/04A61P35/00A61P35/02C07B2200/13A61K31/4985A61P1/04A61P13/08A61P13/12A61P17/00A61P17/04A61P17/06A61P19/00A61P19/02A61P21/00A61P27/02A61P29/00A61P31/04A61P31/18A61P37/02A61P9/00A61P9/10A61P3/10A61K45/06A61K47/36
Inventor F.布拉特T.英加莱恩拉T.巴夫E.阿雷特C.克雷萨J.埃瓦茨
Owner ACERTA PHARMA BV
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