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Crystalline forms of 3-{4-[(2r)-2-aminopropoxy]phenyl}-N-[(1R)-1-(3-fluorophenyl)ethyl]imidazo[1, 2-b]pyridazin-6-amine and salts thereof

A technology of aminopropoxy and fluorophenyl, applied in 3-{4-[(2R)-2-aminopropoxy]phenyl}-N-[(1R)-1-(3-fluorobenzene Base) ethyl] imidazo [1,2-b] pyridazin-6-amine and its salt crystal form field

Pending Publication Date: 2021-12-14
ANHEART THERAPEUTICS (HANGZHOU) CO LTD
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Problems solved by technology

However, all subtypes of the NTRK receptor and its ligands are overexpressed in advanced androgen-independent prostate cancer

Method used

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  • Crystalline forms of 3-{4-[(2r)-2-aminopropoxy]phenyl}-N-[(1R)-1-(3-fluorophenyl)ethyl]imidazo[1, 2-b]pyridazin-6-amine and salts thereof
  • Crystalline forms of 3-{4-[(2r)-2-aminopropoxy]phenyl}-N-[(1R)-1-(3-fluorophenyl)ethyl]imidazo[1, 2-b]pyridazin-6-amine and salts thereof
  • Crystalline forms of 3-{4-[(2r)-2-aminopropoxy]phenyl}-N-[(1R)-1-(3-fluorophenyl)ethyl]imidazo[1, 2-b]pyridazin-6-amine and salts thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Example 1: Preparation and Characterization of Form A of Compound 1 Adipate

[0140] An appropriate amount of the amorphous form of compound 1 adipate was dissolved in 0.5 mL of solvent to form a solution. Anti-solvent was added to the thus obtained solution to obtain a solid, which was confirmed to be Form A of compound 1 adipate salt. If a solid does not form after adding the anti-solvent, remove the solvent and anti-solvent by blow drying to obtain a solid. A variety of solvents and anti-solvents were used in the above experiments and are summarized in Table 2 below.

[0141] Table 2

[0142]

[0143] As shown in Table 2, most solvent / anti-solvent combinations form Form A of Compound 1 adipate salt, except some solvent / anti-solvent combinations form the amorphous form, or Form C, of ​​Compound 1 adipate salt or D.

[0144] The NMR data of Form A of compound 1 adipate salt are as follows: 1H NMR (500MHz, DMSO) δ1.13-1.14 (d, J=5.0Hz, 3H), 1.47-1.48 (d, J=5.0H...

Embodiment 2

[0171] Example 2: Preparation and characteristics of crystal form B of compound 1 adipate

[0172] 12 mg of the amorphous form of compound 1 adipate was placed in a 30 mL beaker. 1 mL of a 1:1 by volume mixture of dichloromethane and methanol was added to the beaker to dissolve the amorphous form of Compound 1 adipate. The solvent was allowed to evaporate slowly at room temperature. After complete evaporation of the solvent, a solid was obtained and confirmed to be Form B of compound 1 adipate salt.

[0173] The NMR data of Form B of compound 1 adipate is as follows: 1H NMR (500MHz, DMSO) δ1.15(br, 3H), 1.48(br, 7H), 2.17(br, 4H), 3.28(br, 1H ), 3.85(br, 2H), 4.823(br, 1H), 6.77(br, 1H), 6.94(br, 2H), 7.03(br, 1H), 7.26(br, 2H), 7.40(br, 1H) , 7.65 (br, 1H), 7.74 (br, 4H).

[0174] The IR data of the crystal form B of compound 1 adipate is as follows: IR (cm -1 ): 3274, 3058, 2972, 2937, 2868, 1700, 1612, 1574, 1333, 1245, 1111, 829, 821.

[0175] A representative XRPD...

Embodiment 3

[0183] Example 3: Preparation and Characterization of Form C of Compound 1 Adipate

[0184] 10 mg of the amorphous form of compound 1 adipate was placed in a 30 mL beaker. 0.5 mL of ethanol was added to the beaker to dissolve the amorphous form of compound 1 adipate. After adding 5 mL of acetone to the beaker, the solution was stirred at room temperature for one day. Then, the solvent was removed by blowing nitrogen gas through the solution to obtain a solid, which was confirmed to be Form C of compound 1 adipate salt.

[0185] The NMR data of Form C of compound 1 adipate salt are as follows: 1H NMR (500MHz, DMSO) δ1.13-1.14 (d, J=5.0Hz, 3H), 1.47-1.48 (d, J=5.0Hz, 7H ), 2.14-2.18(t, J=5.0Hz, J=10.0Hz, 4H), 3.25-3.29(m, 1H), 3.81-3.88(m, 2H), 4.81-4.86(m, 1H), 6.76- 6.78(d, J=10.0Hz, 1H), 6.93-6.94(d, J=5.0Hz, 2H), 7.01-7.05(t, J=10.0Hz, 1H), 7.23-7.28(m, 2H), 7.37 -7.42 (m, 1H), 7.64-7.65 (d, J=5.0Hz, 1H), 7.72-7.76 (t, J=10.0Hz, 4H).

[0186] The IR data of the crysta...

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Abstract

The present disclosure relates to crystalline forms of 3-{4-[(2R)-2-aminopropoxy]phenyl}-N-[(1R)-1-(3-fluorophenyl)ethyl]imidazo[1, 2-b]pyridazin-6-amine and salts thereof, and a preparation method and a using method of the crystalline forms.

Description

technical field [0001] The present disclosure relates to 3-{4-[(2R)-2-aminopropoxy]phenyl}-N-[(1R)-1-(3-fluorophenyl)ethyl]imidazo[1,2- b] Crystal forms of pyridazin-6-amine and salts thereof, and methods for preparing and using such crystal forms. Background technique [0002] 3-{4-[(2R)-2-aminopropoxy]phenyl}-N-[(1R)-1-(3-fluorophenyl)ethyl]-imidazo[1,2-b] Pyridazin-6-amine (Compound 1) is a known ROS1 receptor tyrosine kinase inhibitor and neurotrophic tyrosine receptor kinase (NTRK) inhibitor and has the following chemical structure: [0003] [0004] The ROS1 gene encodes a receptor tyrosine kinase that was found to be the human ortholog of the v-ros cancer gene product of the avian sarcoma virus UR2 (University of Rochester Tumor Virus 2). A ROS1 fusion gene resulting from a chromosomal rearrangement involving the ROS1 gene followed by fusion of the ROS1 gene to another gene was found in the glioblastoma cell line U118MG. In U118MG cells, the gene encoding the Go...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07C55/14C07C51/41C07C51/43A61P35/00A61K31/5025
CPCC07D487/04C07C55/14C07C51/412C07C51/43A61P35/00C07B2200/13C07B2200/07
Inventor 周凤儿陈达刚李平卢静雯薛君
Owner ANHEART THERAPEUTICS (HANGZHOU) CO LTD
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