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US 12,760,015 B2Granted
Crystal of PDE3/PDE4 dual inhibitor and use thereof
AssigneeChia Tai Tianqing Pharmaceutical Group Co., Ltd.
InventorsWenjun Yao, Yunfu Luo, Peng Zhang, Ting Yao
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Abstract
Provided are a crystal of a tricyclic compound as shown in formula (I) or a pharmaceutically acceptable salt thereof and a preparation method therefor, and the use thereof in preparing a drug for treating PDE3- and/or PDE4-related diseases.
Claims20
A crystalline form of a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein the pharmaceutically acceptable salt is sulfate, p-toluenesulfonate, methanesulfonate or maleate:
- wherein the crystalline form of the compound of formula (I) is one of the following crystalline forms:
- (1) a crystalline form comprising 4, 5, 6, 7 or 8 diffraction peaks in an X-ray powder diffraction (XRPD) pattern using Cu Kα radiation selected from the following 2θ angles:
- 4.14±0.2°, 6.56±0.2°, 6.98±0.2°, 8.20±0.2°, 11.50±0.2°, 12.66±0.2°, 13.94±0.2° and 16.35±0.2°;
- (2) a crystalline form comprising 5, 6, 7, 8, 9, 10 or 11 diffraction peaks in an X-ray powder diffraction pattern using Cu Kα radiation selected from the following 2θ angles:
- 5.81±0.2°, 8.38±0.2°, 11.16±0.2°, 13.96±0.2°, 14.47±0.2°, 15.01±0.2°, 16.76±0.2°, 17.95±0.2°, 20.83±0.2°, 24.73±0.2° and 26.13±0.2°;
- or
- (3) a crystalline form comprising 4, 5, 6, 7, 8 or 9 diffraction peaks in an X-ray powder diffraction pattern using Cu Kα radiation selected from the following 2θ angles:
- 4.57±0.2°, 6.41±0.2°, 7.18±0.2°, 11.58±0.2°, 12.84±0.2°, 13.21±0.2°, 14.34±0.2°, 16.05±0.2° and 23.41±0.2°;
- and wherein the crystalline form of the pharmaceutically acceptable salt is one of the following crystalline forms:
- (i) a crystalline form of the compound of formula (II)
- comprising 4, 5, 6, 7 or 8 diffraction peaks in an X-ray powder diffraction pattern using Cu Kα radiation selected from the following 2θ angles:
- 4.84±0.2°, 9.58±0.2°, 10.93±0.2°, 11.97±0.2°, 14.31±0.2°, 14.75±0.2°, 16.49±0.2° and 24.42±0.2°;
- (ii) a crystalline form of the compound of formula (III)
- comprising 3, 4, 5 or 6 diffraction peaks in an X-ray powder diffraction pattern using Cu Kα radiation selected from the following 2θ angles:
- 6.53±0.2°, 10.87±0.2°, 12.48±0.2°, 13.11±0.2°, 16.58±0.2° and 25.03±0.2°;
- (iii) a crystalline form of the compound of formula (IV)
- comprising 4, 5, 6, 7 or 8 diffraction peaks in an X-ray powder diffraction pattern using Cu Kα radiation selected from the following 2θ angles:
- 11.22±0.2°, 12.58±0.2°, 16.43±0.2°, 17.90±0.2°, 18.85±0.2°, 22.62±0.2°, 24.45±0.2° and 25.87±0.2°;
- or
- (iv) a crystalline form of the compound of formula (V)
- comprising 4, 5, 6, 7 or 8 diffraction peaks in an X-ray powder diffraction pattern using Cu Kα radiation selected from the following 2θ angles:
- 5.83±0.2°, 6.62±0.2°, 9.50±0.2°, 10.98±0.2°, 17.16±0.2°, 19.05±0.2°, 24.71±0.2° and 25.16±0.2°.
19 more elements
A method for preparing a compound of formula (I), comprising:
- preparing the compound of formula (I) by method 1 or method 2;
- wherein
- the method 1 comprises:
- (1) reacting compound 1-2a to give compound BB-4;
- and (2) reacting compound BB-4 with 5-hydroxy-3-methyl-1,2,3-triazole-4-carboxylic acid to give the compound of formula (I),
- the method 2 comprises:
- reacting compound 1-4b to give the compound of formula (I)
4 more elements
Dependencies are inferred from the claim text.