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Crystal form of octahydropyrrolo[3,4-c]pyrrole derivative

A crystal form and drug technology, applied in drug combinations, medical preparations containing active ingredients, allergic diseases, etc., can solve problems such as poor water solubility, poor druggability, and low oral bioavailability

Active Publication Date: 2021-06-01
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The inventor found that the compound has poor water solubility, low oral bioavailability, poor stability, and poor druggability when studying the compound, so it is necessary to find a solid form with better druggability

Method used

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  • Crystal form of octahydropyrrolo[3,4-c]pyrrole derivative
  • Crystal form of octahydropyrrolo[3,4-c]pyrrole derivative
  • Crystal form of octahydropyrrolo[3,4-c]pyrrole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0128] Embodiment 1 The crystal form I of the present invention

[0129] 1. Preparation of Form I

[0130] According to the method of Example 3 in the international application WO 2017088759 A1, the compound represented by formula (I) (307 g) was prepared, which was dissolved in DMF (614 mL), heated to 80 ° C and stirred for 0.5 h to dissolve, and then slowly cooled to room temperature , crystallization, suction filtration, the filter residue was washed with water (50mL×2), and air-dried at 70°C to obtain off-white solid powder.

[0131] 2. Identification of Form I

[0132] (1) Analysis and identification by Empyrean X-ray powder diffraction (XRPD): using Cu-Kα radiation, it has the following characteristic peaks expressed in angle 2θ: 7.44°, 7.78°, 8.24°, 12.69°, 12.95°, 14.08°, 14.75 °,15.03°,17.75°,19.71°,20.12°,20.81°,21.30°,21.89°,22.18°,23.27°,25.49°,25.85°,26.08°,26.60°,27.21°,27.44°,27.70°, 28.53°, there is an error margin of ±0.2°.

[0133] (2) Identification ...

Embodiment 2

[0134] Embodiment 2 The present invention is amorphous

[0135] 1. Preparation of Amorphous Form

[0136] Form I (500 mg) of the compound represented by formula (I) was added to DCM (5.0 mL), dissolved at room temperature, and then subjected to rotary evaporation under reduced pressure to precipitate a solid, which was dried to obtain an off-white solid powder.

[0137] 2. Identification of Amorphous Forms

[0138] Identified by Empyrean X-ray powder diffraction (XRPD) analysis: using Cu-Kα radiation, with essentially image 3 The X-ray powder diffraction (XRPD) pattern is shown.

Embodiment 3

[0139] Example 3 Crystal Form II of the present invention

[0140] 1. Preparation of Form II

[0141] Add the crystal form I (200mg) of the compound represented by formula (I) into ethyl acetate (2.0mL), heat to 75°C under stirring, suspend and stir for 24h, stop the reaction, filter with suction, and dry to obtain off-white solid powder. the target crystal form.

[0142] 2. Identification of Form II

[0143] (1) Analysis and identification by Empyrean X-ray powder diffraction (XRPD): using Cu-Kα radiation, it has the following characteristic peaks represented by angle 2θ: 10.43°, 12.31°, 13.08°, 14.49°, 15.18°, 15.92°, 16.00 °,16.61°,16.90°,17.90°,18.42°,20.52°,21.04°,21.45°,23.59°,24.00°,24.26°,24.75°,25.07°,26.26°,26.53°,26.83°,28.02°, 28.31°, 29.31°, 30.03°, 30.42°, 31.20°, 31.56°, 32.25°, 32.80°, 33.63°, 34.24°, 35.54°, 36.41°, 36.96°, 38.33°, 38.78°, there is ±0.2° margin of error.

[0144] (2) Identification by TA Q2000 Differential Scanning Calorimetry (DSC) a...

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Abstract

The invention relates to a crystal form of an octahydropyrrolo[3,4-c]pyrrole derivative. The invention also relates to a pharmaceutical composition containing the crystal form, and an application of the crystal form or the pharmaceutical composition in preparation of medicines for preventing, treating or relieving diseases related to orexin receptors.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to crystal forms of octahydropyrrolo[3,4-c]pyrrole derivatives, in particular to (5-(5-chlorobenzo[d]oxazol-2-yl)hexahydropyrrole The crystal form of [3,4-c]pyrrol-2(1H)-yl)(2-fluoro-6-(2H-1,2,3-triazol-2-yl)phenyl)methanone and Its use further relates to a pharmaceutical composition comprising the crystal form. Background technique [0002] Orexin, also known as hypocretin and orexin, includes orexin A and orexin B (or hypocretin-1 and hypocretin-2), which are secreted by the hypothalamus Its main physiological functions are as follows: 1. Regulate food intake, orexin can activate neurons that regulate food intake, significantly promote food intake, and has a dose-dependent response; 2. Participate in the regulation of energy metabolism, orexin can significantly increase metabolism 3. Participate in the regulation of sleep-wakefulness, orexin can inhibit rapid eye movement sleep, ...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/423A61P25/20A61P25/24A61P25/22A61P25/28A61P25/18A61P25/30A61P25/14A61P25/06A61P25/08A61P25/00A61P25/04A61P25/16A61P29/00A61P9/00A61P3/10A61P3/00A61P5/00A61P9/12A61P37/02
CPCC07D487/04A61P25/20A61P25/24A61P25/22A61P25/28A61P25/18A61P25/30A61P25/14A61P25/06A61P25/08A61P25/00A61P25/04A61P25/16A61P29/00A61P9/00A61P3/10A61P3/00A61P5/00A61P9/12A61P37/02C07B2200/13
Inventor 金传飞许腾飞张英俊
Owner SUNSHINE LAKE PHARM CO LTD
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