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L-proline complex of sodium-glucose cotransporter 2 inhibitor, monohydrate and crystal form thereof
US10301344B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10301344-B2 |
| Application number | US-201515514118-A |
| Country | US |
| Kind code | B2 |
| Filing date | Sep 8, 2015 |
| Priority date | Sep 30, 2014 |
| Publication date | May 28, 2019 |
| Grant date | May 28, 2019 |
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Abstract
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Provided are an L-proline complex of a sodium-glucose cotransporter 2 inhibitor, and a monohydrate and a crystal of the L-proline complex. Specifically, provided are 1,6-dehydrated-1-C{4-chloro-3-[(3-fluoro-4-ethoxyphenyl)methyl]phenyl}-5-C-(hydroxymethyl)-β-L-idopyranose L-proline (a compound of formula (I)), a monohydrate and a type A crystal thereof, and a preparation method therefor. The obtained type A crystal of the compound of formula (I) has good chemical stability and crystal stability, and the crystallization solvent used has low toxicity and low residue, so the type A crystal can be better used in clinical treatment.
First claim
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What is claimed is: 1. Crystal form A of a complex of formula (I): wherein the crystal is a crystal of a monohydrate, and the crystal is characterized by an X-ray powder diffraction (XRPD) spectrum comprising diffraction peaks at angles (2θ) of about 7.82, 17.28, and 18.89. 2. A preparation method of crystal form A of the complex of formula (I) according to claim 1 , comprising the following steps of: (a) dissolving 1,6-anhydro-1-C-{4-chloro-3-[(3-fluoro-4-ethoxyphenyl)methyl]phenyl}-5-C-(hydroxymethyl)-β-L-idopyranose and L-proline in a solvent to obtain a reaction solution, then cooling the reaction solution to precipitate a crystal, wherein the solvent is selected from the group consisting of an organic solvent and a mixed solvent of an organic solvent and water; and the organic solvent is one or more selected from the group consisting of alcohols, ketones, esters, ethers, hydrocarbons and nitriles having 6 or less carbon atoms; and wherein a molar ratio of L-proline and 1,6-anhydro-1-C-{4-chloro-3-[(3-fluoro-4-ethoxyphenyl)methyl]phenyl}-5-C-(hydroxymethyl)-β-L-idopyranose is less than or equal to 2:1; and (b) filtering the crystal, then drying the crystal, thereby obtaining crystal form A of the complex of formula (I). 3. The preparation method according to claim 2 , wherein the organic solvent in step (a) is methanol, ethanol, isopropanol, acetone, ethyl acetate, tetrahydrofuran, acetonitrile, or n-hexane; and the mixed solvent is methanol/water, ethanol/water, isopropanol/water, or ethanol/n-hexane. 4. The preparation method according to claim 2 , wherein the method further comprises a step of recrystallizing the crystal product resulting from drying, the recrystallization solvent is selected from the group consisting of an organic solvent and a mixed solvent of an organic solvent and water; and the organic solvent is at least one selected from the group consisting of alcohols, ketones, esters, ethers, hydrocarbons and nitriles having 6 or less carbon atoms. 5. Crystal form A of a complex of formula (I): wherein the crystal form is characterized by X-ray powder diffraction (XRPD) peaks as shown in FIG. 1 . 6. The crystal form A of the complex of formula (I) according to claim 1 , wherein the crystal form has a differential scanning calorimetry (DSC) spectrum comprising an endothermic melting peak at about 109.5° C. 7. The crystal form A of the complex of formula (I) according to claim 1 , wherein the XRPD spectrum further comprises diffraction peaks at: Angle (2θ) d-value (Angstrom) about 5.50 about 16.07 about 8.64 about 10.22 about 10.33 about 8.55 about 12.18 about 7.26 about 12.49 about 7.08 about 14.47 about 6.11 about 15.51 about 5.71 about 19.39 about 4.58 about 20.40 about 4.35 about 22.85 about 3.89 about 23.89 about 3.72 about 25.93 about 3.43 about 27.66 about 3.22 about 28.97 about 3.08 and about 31.16 about 2.87. 8. The preparation method according to claim 3 , wherein the organic solvent is ethanol and the mixed solvent is ethanol/water. 9. The preparation method according to claim 4 , wherein the organic solvent is methanol, ethanol, isopropanol, acetone, ethyl acetate, tetrahydrofuran, acetonitrile, or n-hexane; and the mixed solvent is methanol/water, ethanol/water, isopropanol/water, or ethanol/n-hexane. 10. A pharmaceutical composition comprising the crystal form A of the complex of formula (I) according to claim 1 and a pharmaceutically acceptable carrier. 11. A method of treating diabetes in a subject in need thereof, the method comprising administering to the subject the pharmaceutical composition according to claim 10 . 12. A pharmaceutical composition comprising the crystal form A of the complex of formula (I) according to claim 5 and a pharmaceutically acceptable carrier. 13. A pharmaceutical composition comprising the crystal form A of the complex of formula (I) according to claim 7 and a pharmaceutically acceptable carrier. 14. A method of treating diabetes in a subject in need thereof, the method comprising administering to the subject the pharmaceutical composition according to claim 12 . 15. A method of treating diabetes in a subject in need thereof, the method comprising administering to the subject the pharmaceutical composition according to claim 13 . 16. The preparation method according to claim 2 , wherein the reaction solution is heated to reflux, filtered, and then cooled to room temperature to precipitate the crystal. 17. The crystal form A of the complex of formula (I) according to claim 1 , wherein the crystal form has the following d-values (angstrom) at the indicated diffraction angles (2θ): Angle (2θ) d-value (Angstrom) about 7.82 about 11.30 about 17.28 about 5.13 and about 18.89 about 4.70.
Assignees
Inventors
Classifications
- C07H19/01Primary
sharing oxygen · CPC title
Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title
Crystalline forms, e.g. polymorphs · CPC title
Processes for the preparation of sugar derivatives · CPC title
for hyperglycaemia, e.g. antidiabetics · CPC title
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- What does patent US10301344B2 cover?
- Provided are an L-proline complex of a sodium-glucose cotransporter 2 inhibitor, and a monohydrate and a crystal of the L-proline complex. Specifically, provided are 1,6-dehydrated-1-C{4-chloro-3-[(3-fluoro-4-ethoxyphenyl)methyl]phenyl}-5-C-(hydroxymethyl)-β-L-idopyranose L-proline (a compound of formula (I)), a monohydrate and a type A crystal thereof, and a preparation method therefor. The ob…
- Who is the assignee on this patent?
- Jiangsu Hengrui Medicine Co
- What technology area does this patent fall under?
- Primary CPC classification C07H19/01. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue May 28 2019 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).