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New crystal form of cyclohexane formamide compound and preparation method thereof

A technology of compounds and crystal forms, applied in the field of medicinal chemistry, can solve problems such as differences in drug solubility, stability and mobile phase, affecting drug safety and effectiveness, and different clinical effects.

Inactive Publication Date: 2020-10-16
SHANGHAI ACEBRIGHT PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Different crystal forms can cause differences in the solubility, stability and flow of drugs, which will affect the safety and effectiveness of drugs, and lead to differences in clinical effects

Method used

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  • New crystal form of cyclohexane formamide compound and preparation method thereof
  • New crystal form of cyclohexane formamide compound and preparation method thereof
  • New crystal form of cyclohexane formamide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0128] (3) The preparation method of the crystal form provided by the present invention is simple and easy to operate and low in cost, and is suitable for drug research and development and industrial production.

[0129] Pharmaceutical compositions and methods of administration

[0130] Since the crystalline form or amorphous form of the present invention has excellent therapeutic and preventive effects on cancer or tumors, the crystalline form or amorphous form of the present invention and pharmaceutical compositions containing the crystalline form or amorphous form of the present invention as main active ingredients can be used For the treatment and / or prevention of anemia.

[0131] The pharmaceutical composition of the present invention comprises the crystal form of the present invention and pharmaceutically acceptable excipients or carriers within the safe and effective amount range.

[0132] Wherein, "safe and effective amount" refers to: the amount of the compound (or c...

Embodiment 1

[0145] Embodiment 1: Preparation of crystal form CM-I

[0146] Weigh 14 mg of the compound of formula (I), dissolve it in 0.5 mL of ethanol at 30° C., and filter. The filtrate was placed at 5° C. and stirred for 24 h, and a solid precipitated out, which was the crystal form CM-I of the compound of formula (I). Carry out XRPD test to the obtained solid, its X-ray powder diffraction data are as shown in table 1, and its XRPD pattern is as follows figure 1 Shown; Carry out TGA test to gained solid, its spectrogram is as figure 2 Shown; Carry out DSC test to gained solid, its spectrogram is as image 3 shown; the obtained solid was 1 H NMR test, its spectrum is as Figure 4 As shown, NMR data: 1 H NMR (400MHz, DMSO-d 6 )δ11.89(s,1H),9.51(s,1H),8.68(d,J=4.1Hz,1H),8.45(dd,J=17.2,5.1Hz,2H),7.99(dd,J=8.6 ,2.2Hz,1H),7.89(dd,J=15.6,6.4Hz,2H),5.17–4.98(m,1H),3.13(s,3H),2.62(d,J=42.2Hz,1H),2.22 (d, J=13.8Hz, 6H), 2.10–1.52 (m, 9H), 1.46 (d, J=7.0Hz, 3H).

[0147] Table 1

[014...

Embodiment 2

[0149] Embodiment 2: Preparation of crystal form CM-II

[0150] Weigh 12 mg of the compound of formula (I), mix it with 0.2 mL of methanol, filter, and place the filtrate in a 3 mL open glass vial. Add 3 mL of methyl tert-butyl ether to a 20 mL large glass bottle. Put the 3mL glass vial containing the filtrate into the 20mL glass vial containing methyl tert-butyl ether, seal the 20mL glass vial, and let it stand at 25°C until a solid is precipitated, and the obtained solid is the compound of formula (I) Crystal form CM-II. Carry out XRPD test to the obtained solid, its X-ray powder diffraction data are as shown in table 2, and its XRPD figure is as follows Figure 9 Shown; Carry out TGA test to gained solid, its spectrogram is as Figure 10 Shown; Carry out DSC test to gained solid, its spectrogram is as Figure 11 shown; the obtained solid was 1 H NMR test, its spectrum is as Figure 12 As shown, NMR data: 1 HNMR (400MHz, DMSO-d 6 )δ11.89(s,1H),9.52(s,1H),8.68(d,J=4.2...

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Abstract

The invention provides a novel crystal form of (1S, 4R)-N-((S)-1-(6-(4-fluoro-1H-pyrazol-1-yl) pyridine-3-yl) ethyl)-1-methoxy-4-(4-methyl-6-((5-methyl-1H-pyrazol-3-yl) amino) pyrimidine-2-yl) cyclohexane formamide (a compound represented by a formula (I)) and a preparation method thereof.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to (1S,4R)-N-((S)-1-(6-(4-fluoro-1H-pyrazol-1-yl)pyridin-3-yl)ethyl) -New crystal form of 1-methoxy-4-(4-methyl-6-((5-methyl-1H-pyrazol-3-yl)amino)pyrimidin-2-yl)cyclohexanecarboxamide and its preparation method. Background technique [0002] RET (Rearranged during transfection) is a relatively rare proto-oncogene, which is located on the long arm of human chromosome 10 and encodes a receptor tyrosine kinase. The receptor spans both sides of the cell membrane and completes signal transduction by forming a protein complex. RET protein plays an important role in the development of kidney and gastrointestinal system. In a variety of cancers, alterations in the RET gene lead to activation of kinases that drive tumor formation and growth. Initially, it was discovered that RET gene alterations were associated with the occurrence of papillary thyroid carcinoma; recent studies...

Claims

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Application Information

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IPC IPC(8): C07D401/14A61K31/506A61P35/00
CPCC07D401/14A61K31/506A61P35/00C07B2200/13
Inventor 彭欢张凤杰张良
Owner SHANGHAI ACEBRIGHT PHARMA CO LTD
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