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US 2026/0308146 A1Published application
Triazolyl-containing compounds
AssigneeChia Tai Tianqing Pharmaceutical Group Co., Ltd.
InventorsYan PENG, Jiawei ZHOU, Qingzhen ZHAO, Shibo ZHANG, Shuaishuai JIANG
Life of this patent
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Abstract
Triazolyl-containing compounds and a preparation method therefor. Particularly, crystals or solvates of compounds of formula I, and the use thereof in preparation of drugs for treating tumors.
Claims28
A compound of formula I, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof,
- wherein,
- R1 is selected from the group consisting of —NH2, C1-6 alkyl-O—, C1-6 alkyl-NH—, and (C1-6 alkyl)2N—;
- ring A is selected from the group consisting of a C6-10 aromatic ring group and a 5- to 10-membered heteroaromatic ring group;
- R is selected from the group consisting of halogen, CN, OH, NH2, C1-6 alkyl, C1-6 alkyl-O—, C1-6 alkyl-S—, C1-6 haloalkyl-O—, C1-6 haloalkyl-S—, C1-6 haloalkyl, C1-6 alkyl substituted with 3- to 10-membered heterocycloalkyl, RaNH—, and (Ra)2N—;
- Ra is selected from the group consisting of C1-6 alkyl, C3-10 cycloalkyl, and 3- to 10-membered heterocycloalkyl, and Ra is optionally substituted with one or more groups selected from the group consisting of halogen, CN, OH, NH2, C1-6 alkyl, C1-6 alkyl-O—, and 5- to 6-membered heterocycloalkyl;
- n is selected from the group consisting of 0, 1, 2, 3, and 4;
- R2 is selected from the group consisting of cyclopropyl and trifluoromethyl.
4 more elements
(canceled)
(canceled)
(canceled)
18-27. (canceled)
The compound of formula I, the stereoisomer thereof, or the pharmaceutically acceptable salt thereof according to claim 1514, being selected from a crystalline form of compound 3-A, wherein the crystalline form of compound 3-A has diffraction peaks in an X-ray powder diffraction (XRPD) pattern using Cu Kα radiation at 2θ angles selected from 10.48±0.20°, 19.46±0.20°, 21.56±0.20°, and 23.28±0.20°;
- alternatively, the crystalline form has diffraction peaks at 10.48±0.20°, 12.78±0.20°, 19.46±0.20°, 20.74±0.20°, 21.56±0.20°, 21.94±0.20°, or 23.28±0.20°;
- alternatively, the crystalline form has diffraction peaks at 10.48±0.20°, 12.78±0.20°, 14.68±0.20°, 18.49±0.20°, 19.07±0.20°, 19.46±0.20°, 21.02±0.20°, 20.74±0.20°, 21.56±0.20°, 21.94±0.20°, or 23.28±0.20°;
- alternatively, the crystalline form has diffraction peaks at 10.48±0.20°, 11.89±0.20°, 12.78±0.20°, 14.68±0.20°, 18.49±0.20°, 19.07±0.20°, 19.46±0.20°, 21.02±0.20°, 20.74±0.20°, 21.56±0.20°, 21.94±0.20°, 22.33±0.20°, or 23.28±0.20°;
- alternatively, the crystalline form has at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, or more characteristic diffraction peaks at 2θ values selected from the group consisting of 10.48±0.20°, 11.89±0.20°, 12.78±0.20°, 14.68±0.20°, 18.49±0.20°, 19.07±0.20°, 19.46±0.20°, 21.02±0.20°, 20.74±0.20°, 21.56±0.20°, 21.94±0.20°, 22.33±0.20°, and 23.28±0.20°;
- or the crystalline form of the solvate of compound 3-A has diffraction peaks in an X-ray powder diffraction (XRPD) pattern using Cu Kα radiation at 2θ angles selected from 7.21±0.20°, 23.03±0.20°, and 24.18±0.20°;
- alternatively, the crystalline form has diffraction peaks at 7.21±0.20°, 19.74±0.20°, 21.31±0.20°, 21.68±0.20°, 22.03±0.20°, 23.03±0.20°, or 24.18±0.20°;
- alternatively, the crystalline form has diffraction peaks at 7.21±0.20°, 12.56±0.20°, 13.47±0.20°, 13.87±0.20°, 19.74±0.20°, 21.31±0.20°, 21.68±0.20°, 22.03±0.20°, 23.03±0.20°, or 24.18±0.20°;
- alternatively, the crystalline form has diffraction peaks at 7.21±0.20°, 12.56±0.20°, 13.47±0.20°, 13.87±0.20°, 18.31±0.20°, 18.60±0.20°, 19.74±0.20°, 21.31±0.20°, 21.68±0.20°, 22.03±0.20°, 23.03±0.20°, 24.18±0.20°, or 24.95±0.20°;
- alternatively, the crystalline form has at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, or more characteristic diffraction peaks at 2θ values selected from the group consisting of 7.21±0.20°, 12.56±0.20°, 13.47±0.20°, 13.87±0.20°, 18.31±0.20°, 18.60±0.20°, 19.74±0.20°, 21.31±0.20°, 21.68±0.20°, 22.03±0.20°, 23.03±0.20°, 24.18±0.20° and 24.95±0.20°;
- optionally, the crystalline form of the solvate of compound 3-A is a crystalline form of a 1,4-dioxane solvate of compound 3-A;
- optionally, in the crystalline form of the 1,4-dioxane solvate of compound 3-A, a molar ratio of compound 3-A to 1,4-dioxane is selected from the group consisting of about 1:0.2-2, about 1:0.2-1, about 1:0.3-0.8, and about 1:0.5;
- or the crystalline form of the solvate of compound 3-A has diffraction peaks in an X-ray powder diffraction (XRPD) pattern using Cu Kα radiation at 2θ angles selected from 8.40±0.20°, 19.29±0.20°, 22.11±0.20°, and 22.89±0.20°;
- alternatively, the crystalline form has diffraction peaks at 8.40±0.20°, 18.62±0.20°, 19.29±0.20°, 20.35±0.20°, 21.30±0.20°, 22.11±0.20°, 22.89±0.20°, or 26.27±0.20°;
- alternatively, the crystalline form has diffraction peaks at 8.40±0.20°, 14.87±0.20°, 16.83±0.20°, 17.10±0.20°, 18.62±0.20°, 19.29±0.20°, 20.35±0.20°, 21.30±0.20°, 22.11±0.20°, 22.89±0.20°, or 26.27±0.20°;
- alternatively, the crystalline form has diffraction peaks at 8.40±0.20°, 13.08±0.20°, 14.58±0.20°, 14.87±0.20°, 16.83±0.20°, 17.10±0.20°, 18.62±0.20°, 19.29±0.20°, 20.35±0.20°, 21.30±0.20°, 22.11±0.20°, 22.89±0.20°, 23.47±0.20°, 25.43±0.20°, or 26.27±0.20°;
- alternatively, the crystalline form has at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, or more characteristic diffraction peaks at 2θ values selected from the group consisting of 8.40±0.20°, 13.08±0.20°, 14.58±0.20°, 14.87±0.20°, 16.83±0.20°, 17.10±0.20°, 18.62±0.20°, 19.29±0.20°, 20.35±0.20°, 21.30±0.20°, 22.11±0.20°, 22.89±0.20°, 23.47±0.20°, 25.43±0.20°, and 26.27±0.20°;
- optionally, the crystalline form of the solvate of compound 3-A is a crystalline form of a tetrahydrofuran solvate of compound 3-A;
- optionally, in the crystalline form of the tetrahydrofuran solvate of compound 3-A, a molar ratio of compound 3-A to tetrahydrofuran is selected from the group consisting of:
- about 1:0.2-2, about 1:0.2-1, about 1:0.3-0.8, and about 1:0.5.
16 more elements
(canceled)
(canceled)
The compound of formula I, the stereoisomer thereof, or the pharmaceutically acceptable salt thereof according to claim 1514, being selected from a crystalline form of compound 15-A, wherein the crystalline form of compound 15-A has diffraction peaks in an X-ray powder diffraction (XRPD) pattern using Cu Kα radiation at 2θ angles selected from 8.13±0.20°, 17.08±0.20°, 20.23±0.20°, and 20.97±0.20°;
- alternatively, the crystalline form has diffraction peaks at 8.13±0.20°, 15.63±0.20°, 17.08±0.20°, 19.94±0.20°, 20.23±0.20°, 20.97±0.20°, 21.87±0.20°, or 23.63±0.20°;
- alternatively, the crystalline form has diffraction peaks at 8.13±0.20°, 9.63±0.20°, 14.27±0.20°, 15.63±0.20°, 17.08±0.20°, 19.22±0.20°, 19.94±0.20°, 20.23±0.20°, 20.97±0.20°, 21.32±0.20°, 21.87±0.20°, 22.48±0.20°, or 23.63±0.20°;
- alternatively, the crystalline form has diffraction peaks at 8.13±0.20°, 9.63±0.20°, 11.78±0.20°, 13.36±0.20°, 14.27±0.20°, 15.63±0.20°, 17.08±0.20°, 19.22±0.20°, 19.94±0.20°, 20.23±0.20°, 20.97±0.20°, 21.32±0.20°, 21.87±0.20°, 22.48±0.20°, 23.63±0.20°, 24.26±0.20°, or 25.05±0.20°;
- alternatively, the crystalline form has at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, or more characteristic diffraction peaks at 2θ values selected from the group consisting of 8.13±0.20°, 9.63±0.20°, 11.78±0.20°, 13.36±0.20°, 14.27±0.20°, 15.63±0.20°, 17.08±0.20°, 19.22±0.20°, 19.94±0.20°, 20.23±0.20°, 20.97±0.20°, 21.32±0.20°, 21.87±0.20°, 22.48±0.20°, 23.63±0.20°, 24.26±0.20°, and 25.05±0.20°;
- or the crystalline form of the solvate of compound 15-A has diffraction peaks in an X-ray powder diffraction (XRPD) pattern using Cu Kα radiation at 2θ angles selected from 6.30±0.20°, 16.79±0.20°, and 24.00±0.20°;
- alternatively, the crystalline form has diffraction peaks at 6.30±0.20°, 7.85±0.20°, 16.79±0.20°, 18.43±0.20°, 22.85±0.20°, or 24.00±0.20°;
- alternatively, the crystalline form has diffraction peaks at 6.30±0.20°, 7.85±0.20°, 10.18±0.20°, 12.21±0.20°, 15.69±0.20°, 16.79±0.20°, 17.69±0.20°, 18.43±0.20°, 18.80±0.20°, 22.85±0.20°, or 24.00±0.20°;
- alternatively, the crystalline form has diffraction peaks at 6.30±0.20°, 7.85±0.20°, 10.18±0.20°, 12.21±0.20°, 14.71±0.20°, 15.69±0.20°, 16.79±0.20°, 17.69±0.20°, 18.43±0.20°, 18.80±0.20°, 22.85±0.20°, 24.00±0.20°, or 26.08±0.20°;
- alternatively, the crystalline form has diffraction peaks at 6.30±0.20°, 7.85±0.20°, 10.18±0.20°, 12.21±0.20°, 14.71±0.20°, 15.69±0.20°, 16.79±0.20°, 17.69±0.20°, 18.43±0.20°, 18.80±0.20°, 21.23±0.20°, 22.85±0.20°, 24.00±0.20°, 26.08±0.20°, or 26.72±0.20°;
- alternatively, the crystalline form has at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, or more characteristic diffraction peaks at 2θ values selected from the group consisting of 6.30±0.20°, 7.85±0.20°, 10.18±0.20°, 12.21±0.20°, 14.71±0.20°, 15.69±0.20°, 16.79±0.20°, 17.69±0.20°, 18.43±0.20°, 18.80±0.20°, 21.23±0.20°, 22.85±0.20°, 24.00±0.20°, 26.08±0.20°, and 26.72±0.20°;
- optionally, the crystalline form of the solvate of compound 15-A is a crystalline form of an acetonitrile solvate of compound 15-A;
- optionally, in the crystalline form of the acetonitrile solvate of compound 15-A, a molar ratio of compound 15-A to acetonitrile is selected from the group consisting of:
- 1:0.2-2, 1:0.5-1.5, 1:0.5-1, and 1:1.
10 more elements
(canceled)
The compound of formula I, the stereoisomer thereof, or the pharmaceutically acceptable salt thereof according to claim 1514, being selected from a crystalline form of compound 25-A, wherein the crystalline form of compound 25-A has diffraction peaks in an X-ray powder diffraction (XRPD) pattern using Cu Kα radiation at 2θ angles selected from 4.53±0.20°, 7.13±0.20°, 16.30±0.20°, and 20.50±0.20°;
- alternatively, the crystalline form has diffraction peaks at 4.53±0.20°, 7.13±0.20°, 9.04±0.20°, 16.30±0.20°, 19.21±0.20°, 20.50±0.20°, 20.87±0.20°, 24.54±0.20°, or 25.92±0.20°;
- alternatively, the crystalline form has diffraction peaks at 4.53±0.20°, 7.13±0.20°, 9.04±0.20°, 11.29±0.20°, 16.30±0.20°, 17.24±0.20°, 17.65±0.20°, 19.21±0.20°, 20.50±0.20°, 20.87±0.20°, 22.29±0.20°, 24.54±0.20°, or 25.92±0.20°;
- alternatively, the crystalline form has diffraction peaks at 4.53±0.20°, 7.13±0.20°, 9.04±0.20°, 11.29±0.20°, 16.30±0.20°, 17.24±0.20°, 17.65±0.20°, 18.12±0.20°, 19.21±0.20°, 20.50±0.20°, 20.87±0.20°, 22.29±0.20°, 24.54±0.20°, 25.29±0.20°, 25.92±0.20°, or 30.47±0.20°;
- alternatively, the crystalline form has at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, or more characteristic diffraction peaks at 2θ values selected from the group consisting of 4.53±0.20°, 7.13±0.20°, 9.04±0.20°, 11.29±0.20°, 16.30±0.20°, 17.24±0.20°, 17.65±0.20°, 18.12±0.20°, 19.21±0.20°, 20.50±0.20°, 20.87±0.20°, 22.29±0.20°, 24.54±0.20°, 25.29±0.20°, 25.92±0.20°, and 30.47±0.20°.
1 more element
(canceled)
Dependencies are inferred from the claim text.