CN105693695A - Delafloxacin meglumine salt crystal form, and preparation method thereof - Google Patents
Delafloxacin meglumine salt crystal form, and preparation method thereof Download PDFInfo
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- CN105693695A CN105693695A CN201410681562.7A CN201410681562A CN105693695A CN 105693695 A CN105693695 A CN 105693695A CN 201410681562 A CN201410681562 A CN 201410681562A CN 105693695 A CN105693695 A CN 105693695A
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- meglumine salt
- lasha star
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- meglumine
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- 239000013078 crystal Substances 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title abstract description 14
- AHJGUEMIZPMAMR-WZTVWXICSA-N 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxoquinoline-3-carboxylic acid;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C1=C(F)C(N)=NC(N2C3=C(Cl)C(N4CC(O)C4)=C(F)C=C3C(=O)C(C(O)=O)=C2)=C1F AHJGUEMIZPMAMR-WZTVWXICSA-N 0.000 title abstract 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 17
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 229960003194 meglumine Drugs 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- 239000012296 anti-solvent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 3
- 238000012360 testing method Methods 0.000 description 15
- 238000005755 formation reaction Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- -1 meglumine salt trihydrate Chemical class 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 108020000946 Bacterial DNA Proteins 0.000 description 1
- 108090000323 DNA Topoisomerases Proteins 0.000 description 1
- 102000003915 DNA Topoisomerases Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- QOPAMSBHSSXKGC-UHFFFAOYSA-N [F].C1=CC=C2NC(=O)C=CC2=C1 Chemical class [F].C1=CC=C2NC(=O)C=CC2=C1 QOPAMSBHSSXKGC-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- DYDCPNMLZGFQTM-UHFFFAOYSA-N delafloxacin Chemical compound C1=C(F)C(N)=NC(N2C3=C(Cl)C(N4CC(O)C4)=C(F)C=C3C(=O)C(C(O)=O)=C2)=C1F DYDCPNMLZGFQTM-UHFFFAOYSA-N 0.000 description 1
- 229950006412 delafloxacin Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 208000001786 gonorrhea Diseases 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a delafloxacin meglumine salt novel crystal form, and a preparation method thereof. The delafloxacin meglumine salt novel crystal form is characterized in that characteristic diffraction peaks can be observed at 2theta of about 6.0 DEG, 7.9 DEG, 9.4 DEG, 13.0 DEG, 17.1 DEG, 19.2 DEG, 20.9 DEG, 22.0 DEG, 23.0 DEG, 23.8 DEG, 25.4 DEG, 26.6 DEG, and 29.7 DEG in the X-ray powder diffraction pattern of the delafloxacin meglumine salt novel crystal form. The delafloxacin meglumine salt novel crystal form is high in purity, and stability.
Description
Technical field
The present invention relates to medicinal chemistry arts, be specifically related to novel crystal forms of a kind of De Lasha star meglumine salt and preparation method thereof。
Background technology
De Lasha star (Delafloxacin), chemistry is by name: 1-(6-amino-3,5-difluoro pyridine-2-base) the fluoro-7-of the chloro-6-of-8-(3-hydroxy azetidine-1-base)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, structure shown in formula I, can be prepared by the method disclosed in patent WO0250043:
De Lasha star is a kind of fluorine quinolone compounds developed by Wakunaga pharmaceutical Co. Ltd of Japan, Abbott company of the U.S. once obtained its exploitation license, treated company's (predecessor is RIB-X pharmacy) by Melinta at present to develop, be in III phase clinical investigation phase。Its mechanism of action is identical with other fluoroquinolones, act on Bacterial DNA gyrase and topoisomerase I V, prominent Inhibiting enzyme activity can reduce the selectivity of bacterial resistance sudden change, is expected to become the drug candidate of the diseases such as treatment respiratory tract, urinary tract infection and Simple gonorrhea, acute bacterial skin and skin structure infection。
De Lasha star belongs to slightly water-soluble compound, and the research of its crystal formation is of great significance。
Patent US7728143 discloses crystal formation of a kind of De Lasha star meglumine salt and a kind of De Lasha star meglumine salt trihydrate and preparation method thereof, and disclose X-ray powder diffraction, but the inventors discovered that both crystal formations also less stable, the easy moisture absorption of anhydrous crystal forms。
The present inventor is found that the novel crystal forms of a kind of De Lasha star meglumine salt in the process that De Lasha star meglumine salt is studied, and this novel crystal forms preparation method is simple, good stability, it is adaptable to the manufacture of several formulations。
Summary of the invention
It is an object of the invention to provide novel crystal forms of a kind of De Lasha star meglumine salt and preparation method thereof, this crystal formation preparation technology is simple, and the not easily moisture absorption or dehydration, good stability is suitable to the manufacture process of industrialized production and preparation。
For realizing the purpose of the present invention, the invention provides the crystal formation of a kind of De Lasha star meglumine salt, herein this crystal formation is defined as " De Lasha star meglumine salt crystal form A "。
In one embodiment, a kind of De Lasha star meglumine salt crystal form A of the present invention, its X-ray powder diffraction is about the position of 6.0 °, 7.9 °, 9.4 °, 13.0 °, 17.1 °, 19.2 °, 20.9 °, 22.0 °, 23.0 °, 23.8 °, 25.4 °, 26.6 °, 29.7 ° to there being characteristic diffraction peak in 2 θ values。
In the above-described embodiment, the De Lasha star meglumine salt crystal form A of the present invention, may further include 2 θ values and is about the position of 7.4 °, 11.8 °, 13.9 °, 15.1 °, 15.8 °, 16.2 °, 18.9 °, 21.2 °, 22.4 °, 24.9 °, 26.0 °, 27.3 °, 28.0 °, 28.4 °, 29.4 °, 30.5 °, 31.1,31.9 °, 32.5 °, 36.4 °, 37.7 °, 42.4 ° to there being characteristic diffraction peak。
In the above-described embodiment, the De Lasha star meglumine salt crystal form A of the present invention, there is X-ray powder diffraction characteristic peak as shown in Figure 1。
In the above-described embodiment, the De Lasha star meglumine salt crystal form A of the present invention, its DSC scans the scope of first endothermic peak between 60 ~ 105 DEG C, particularly reaches peak value at about 88 DEG C；Second endothermic peak scope, between 170 ~ 190 DEG C, particularly reaches peak value at about 178 DEG C；Its TGA there are about the weightlessness of 7.8% 50 ~ 100 DEG C of scopes。
The De Lasha star meglumine salt crystal form A of the present invention has the characteristic peak representated by X-ray powder diffraction as shown in Figure 1。
The De Lasha star meglumine salt crystal form A of the present invention has the characteristic peak representated by DSC-TGA collection of illustrative plates as shown in Figure 2。
The De Lasha star meglumine salt crystal form A of the present invention, its water content is about 7.0～9.0%, is the trihydrate of De Lasha star meglumine salt。
The powder diffraction test of the De Lasha star meglumine salt crystal form A of the present invention is under ambient temperature and ambient humidity, through CuK α (α=1.54059 of X, PertProMPDX-x ray diffractometer x?) measured。" ambient temperature " is usually 0～40 DEG C, and ambient humidity is usually the relative humidity of 30% ~ 80%。" representational X-ray powder diffraction " refers to that the X-ray powder diffraction feature of this crystal formation meets the overall complexion of this collection of illustrative plates display, it is understandable that, in test process, owing to being subject to the impact of many factors (during such as the granularity of test sample, test the processing method of sample, instrument, test parameter, test operation etc.), the X-ray powder diffraction measured by same crystal formation go out peak position or peak intensity has certain difference。In X-ray powder diffraction, the experimental error of diffraction maximum 2 θ value can be ± 0.2 °, and therefore, in the crystal formation of the present invention, in " 2 θ values are about ", " about " word and Representative errors are ± 0.2 °。
The DSC-TGA test condition of the De Lasha star meglumine salt crystal form A of the present invention is under ambient temperature and ambient humidity, completes through Switzerland Mettler1100LF type instrument test。High-purity Ar gas purges with the flow velocity of 50ml/min, carries out temperature programming with the speed of 10 DEG C/min, and temperature elevating range is that room temperature is to 350 DEG C。" ambient temperature " is usually 0～40 DEG C；" ambient humidity " is usually the relative humidity of 30%～80%。
The purpose of the present invention additionally provides a kind of method preparing De Lasha star meglumine salt crystal form A, and its reaction equation is as follows:
In one embodiment, a kind of method preparing De Lasha star meglumine salt crystal formation of the present invention, comprise the following steps:
1) De Lasha star and meglumine are mixed in water, stirring and dissolving；
2) cooling crystallize/or add anti-solvent and lower the temperature again crystallize；
3) filter or centrifugation goes out crystal, be drying to obtain。
In the above-described embodiment, the method for the present invention, the molar ratio range of De Lasha star and meglumine is 1:0.8～1:1.5, it is preferred to 1:1～1:1.4；Described anti-solvent includes methanol, ethanol, isopropanol, acetone, oxolane, acetonitrile etc. or their mixture, it is preferred to ethanol, isopropanol or their mixture；Described dry, its baking temperature is 0～60 DEG C, it is preferred to 20～50 DEG C, and described drying carries out under normal pressure or reduced pressure, and described reduced pressure vacuum is generally 300～760mmHg, it is preferable that 600～760mmHg。
In one embodiment, the method preparing De Lasha star meglumine salt crystal form A of the present invention, comprise the steps of
1). by De Lasha star and the meglumine water dissolution being suitable for, obtaining De Lasha star meglumine solution, wherein, solution temperature is 0～100 DEG C, it is preferable that 20～60 DEG C；
2). upper step De Lasha star meglumine salt solution carrying out cooling crystallization, or upwards adds suitable anti-solvent, cooling crystallization in step De Lasha star meglumine salt solution, recrystallization temperature is-20～50 DEG C, it is preferable that 0～20 DEG C；
3). the crystal of precipitation is filtered or centrifugation；
4). optional, it is dried separating the crystal drawn, baking temperature is 0～60 DEG C, it is preferable that 20～50 DEG C, it is possible to constant pressure and dry, it is also possible to drying under reduced pressure, during decompression, vacuum is generally 300～760mmHg, it is preferable that 600～760mmHg。
In above-mentioned specific embodiments, the method of the present invention, in step 1), the molar ratio range of De Lasha star and meglumine is 1:0.8～1:1.5, preferred 1:1～1:1.2, in step 2, described suitable anti-solvent includes methanol, ethanol, isopropanol, acetone, oxolane, acetonitrile etc. or their mixture, it is preferable that ethanol, isopropanol or their mixture。
In the above-described embodiment, the method for the present invention, the crystallize mode of De Lasha star meglumine salt crystal form A can be stirring for crystallize, it is also possible to is stand crystallize。
For investigating the stability of above-mentioned De Lasha star meglumine salt crystal form A, the De Lasha star meglumine salt crystal form A of embodiment gained having been carried out influence factor's test, result is shown in table 1 below:
Above-mentioned result of the test shows, De Lasha star meglumine salt crystal form A of the present invention has stable physicochemical properties, is suitable to long storage periods and is applied to preparation。
Beneficial effect: De Lasha star meglumine salt crystal form A provided by the present invention is clearly distinguishable from existing crystal formation, is the crystal habit that De Lasha star meglumine salt is new。The features such as it is simple that the De Lasha star meglumine salt crystal form A of the present invention possesses preparation method, excellent in stability, are suitable for the manufacture of industrialized production and its preparation。
Accompanying drawing explanation
Fig. 1 is the X-ray powder diffraction of De Lasha star meglumine salt crystal form A
Fig. 2 is the DSC-TGA collection of illustrative plates of De Lasha star meglumine salt crystal form A
Detailed description of the invention
Below in conjunction with embodiment, the invention will be further described, it is possible to makes those skilled in the art be more completely understood by the present invention, but the scope not limited the present invention in any way。
Embodiment 1
The preparation of De Lasha star meglumine salt crystal form A
Weigh De Lasha star 20g, meglumine 11g adds in 100ml pure water, it is warming up to 50 DEG C of stirring 6h, slowly cools to 10 DEG C of stirring and crystallizing 5h, sucking filtration, filter cake is drying under reduced pressure get De Lasha star meglumine salt crystal form A 25g under 30～40 DEG C of conditions, test X-ray powder diffraction, result is shown in Fig. 1, and main test data values such as table 2 below (lists the relative intensity test data be more than or equal to 10%), test DSC-TGA, result is shown in Fig. 2.
The XRPD of table 1 De Lasha star meglumine salt crystal form A tests data result
Table 1 is transferred nextpage
Embodiment 2:
The preparation of De Lasha star meglumine salt crystal form A
Weigh De Lasha star 20g, meglumine 10.5g adds in 40ml pure water, it is warming up to 45 DEG C of stirring and dissolving, isopropanol 120ml is added after 2h, about 5 DEG C stirring and crystallizing 3h are slowly cooled to after stirring 30min, sucking filtration, filter cake is drying under reduced pressure get De Lasha star meglumine salt crystal form A 27g under 20 ~ 30 DEG C of conditions, and its X-ray powder diffraction pattern (XRPD) is consistent with Fig. 1 in range of error。
Embodiment 3:
Weigh De Lasha star 20g, meglumine 10.0g adds in 50ml pure water, ethanol 100ml is added after being warming up to 40 DEG C of stirring 2h, about 5 DEG C stirring and crystallizing 3h are slowly cooled to after stirring 30min, sucking filtration, filter cake is drying under reduced pressure get De Lasha star meglumine salt crystal form A 22g under 20～30 DEG C of conditions, and its X-ray powder diffraction pattern is consistent with Fig. 1 in range of error。
Above detail the present invention, including its preferred embodiment。However, it should be understood that consider present disclosure, the present invention can be changed in the spirit of invention and/or improve by those skilled in the art, falls within the scope of the present invention。
Claims (10)
1. Yi Zhong De Lasha star meglumine salt crystal formation, it is characterised in that: its X-ray powder diffraction is about the position of 6.0 °, 7.9 °, 9.4 °, 13.0 °, 17.1 °, 19.2 °, 20.9 °, 22.0 °, 23.0 °, 23.8 °, 25.4 °, 26.6 °, 29.7 ° to there being characteristic diffraction peak in 2 θ values。
2. De Lasha star meglumine salt novel crystal forms as claimed in claim 1, its X-ray powder diffraction may further include 2 θ values and is about the position of 7.4 °, 11.8 °, 13.9 °, 15.1 °, 15.8 °, 16.2 °, 18.9 °, 21.2 °, 22.4 °, 24.9 °, 26.0 °, 27.3 °, 28.0 °, 28.4 °, 29.4 °, 30.5 °, 31.1,31.9 °, 32.5 °, 36.4 °, 37.7 °, 42.4 ° to there being characteristic diffraction peak。
3. the method preparing De Lasha star meglumine salt crystal formation described in claim 1 or 2, comprises the following steps:
1) De Lasha star and meglumine are mixed in water, stirring and dissolving；
2) cooling crystallize/or add anti-solvent and lower the temperature again crystallize；
3) filter or centrifugation goes out crystal, be drying to obtain。
4. method as claimed in claim 3, the molar ratio range of De Lasha star and meglumine is 1:0.8～1:1.5。
5. method as claimed in claim 4, the molar ratio range of De Lasha star and meglumine is 1:1～1:1.4。
6. method as claimed in claim 3, described anti-solvent includes methanol, ethanol, isopropanol, acetone, oxolane, acetonitrile etc. or their mixture。
7. method as claimed in claim 6, described anti-solvent is ethanol, isopropanol or their mixture。
8. method as claimed in claim 3, described dry, its baking temperature is 0～60 DEG C。
9. method as claimed in claim 8, described baking temperature is 20～50 DEG C。
10. method as claimed in claim 3, described drying carries out under normal pressure or vacuum condition。
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017223A (en) * | 2015-07-08 | 2015-11-04 | 扬子江药业集团有限公司 | Delafloxacin meglumine crystal form I and preparation method thereof |
| CN110467600A (en) * | 2018-05-10 | 2019-11-19 | 上海度德医药科技有限公司 | A kind of De Lasha star meglumine salt crystal form L and preparation method thereof |
| CN111718329A (en) * | 2019-03-23 | 2020-09-29 | 南京海润医药有限公司 | A kind of delafloxacin impurity IV and product refining method |
| CN111718330A (en) * | 2019-03-23 | 2020-09-29 | 南京海润医药有限公司 | A kind of delafloxacin impurity III and product refining method |
| CN111718331A (en) * | 2019-03-23 | 2020-09-29 | 南京海润医药有限公司 | Impurities I and II of Delafloxacin and product refining method |
| CN113527262A (en) * | 2021-06-22 | 2021-10-22 | 安徽普利药业有限公司 | Refining method of delafloxacin and meglumine salt thereof |
| WO2023137966A1 (en) * | 2022-01-20 | 2023-07-27 | 海南普利制药股份有限公司 | New crystal form of delafloxacin meglumine and preparation method therefor |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017223A (en) * | 2015-07-08 | 2015-11-04 | 扬子江药业集团有限公司 | Delafloxacin meglumine crystal form I and preparation method thereof |
| CN110467600A (en) * | 2018-05-10 | 2019-11-19 | 上海度德医药科技有限公司 | A kind of De Lasha star meglumine salt crystal form L and preparation method thereof |
| CN111718329A (en) * | 2019-03-23 | 2020-09-29 | 南京海润医药有限公司 | A kind of delafloxacin impurity IV and product refining method |
| CN111718330A (en) * | 2019-03-23 | 2020-09-29 | 南京海润医药有限公司 | A kind of delafloxacin impurity III and product refining method |
| CN111718331A (en) * | 2019-03-23 | 2020-09-29 | 南京海润医药有限公司 | Impurities I and II of Delafloxacin and product refining method |
| CN113527262A (en) * | 2021-06-22 | 2021-10-22 | 安徽普利药业有限公司 | Refining method of delafloxacin and meglumine salt thereof |
| WO2023137966A1 (en) * | 2022-01-20 | 2023-07-27 | 海南普利制药股份有限公司 | New crystal form of delafloxacin meglumine and preparation method therefor |
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