CN103450119A - Cabazitaxel with crystal form W and method for preparing same - Google Patents
Cabazitaxel with crystal form W and method for preparing same Download PDFInfo
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- CN103450119A CN103450119A CN2013104404584A CN201310440458A CN103450119A CN 103450119 A CN103450119 A CN 103450119A CN 2013104404584 A CN2013104404584 A CN 2013104404584A CN 201310440458 A CN201310440458 A CN 201310440458A CN 103450119 A CN103450119 A CN 103450119A
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- 239000013078 crystal Substances 0.000 title claims abstract description 64
- BMQGVNUXMIRLCK-OAGWZNDDSA-N cabazitaxel Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC)C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=3C=CC=CC=3)C[C@]1(O)C2(C)C)C)OC)C(=O)C1=CC=CC=C1 BMQGVNUXMIRLCK-OAGWZNDDSA-N 0.000 title claims abstract description 48
- 229960001573 cabazitaxel Drugs 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 239000008367 deionised water Substances 0.000 claims abstract description 3
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- 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
- 239000002904 solvent Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 5
- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 102000029749 Microtubule Human genes 0.000 description 3
- 108091022875 Microtubule Proteins 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000035800 maturation Effects 0.000 description 3
- 210000004688 microtubule Anatomy 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910017488 Cu K Inorganic materials 0.000 description 1
- 229910017541 Cu-K Inorganic materials 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- 102000004243 Tubulin Human genes 0.000 description 1
- 108090000704 Tubulin Proteins 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001946 anti-microtubular Effects 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention provides a cabazitaxel with a crystal form W and a method for preparing the cabazitaxel with the crystal form W. Characteristic peaks 2theta of an X-ray powder diffraction pattern of the cabazitaxel with the crystal form W is 4.4 degrees+/-0.2 degrees, 7.8 degrees+/-0.2 degrees, 8.5 degrees+/-0.2 degrees, 11.4 degrees +/-0.2 degrees, 12.8 degrees +/-0.2 degrees, 15.3 degrees +/-0.2 degrees, 17.0 degrees +/-0.2 degrees, 20.4 degrees +/-0.2 degrees, 21.4 degrees +/-0.2 degrees, 22.5 degrees +/-0.2 degrees, 23.4 degrees +/-0.2 degrees, 27.8 degrees +/-0.2 degrees, 29.7 degrees +/-0.2 degrees, 29.9 degrees +/-0.2 degrees, 33.3 degrees +/-0.2 degrees and 34.3 degrees +/-0.2 degrees. The method for preparing the cabazitaxel with the crystal form W includes the steps of dissolving cabazitaxel with any crystal form into a proper amount of organic solvents, then, slowly adding deionized water to the mixture while stirring the mixture, then, lowering the temperature of the mixture to the environmental temperature, standing the mixture till recrystallization, and filtering, washing and drying the mixture to obtain the cabazitaxel with the crystal form W. Compared with cabazitaxel with a crystal form reported in a known patent document, the cabazitaxel with the crystal form W has the great advantages of being stable in crystal form, simpler in preparing process, free of the harsh requirements on the environment and devices and strong in repeatability, and thereby being beneficial to industrial production.
Description
Technical field
The invention belongs to medical technical field, particularly relate to a kind of Cabazitaxel (cabazitaxel) crystal formation W and preparation method thereof.
Background technology
Cabazitaxel (cabazitaxel) belongs to yew alkanes antitumour drug, its chemistry 4-acetoxyl group by name-2 α-benzoyloxy-5 β, 20 epoxies-1-hydroxyl-7 β, 10 β-dimethoxy-9-oxo-11-Japanese yew alkene-13 α-Ji alcohol-(2R, 3S)-3-t-butoxycarbonyl amino-PLA ester.Structural formula is as shown in the formula shown in (I):
The mechanism of anticancer action of Cabazitaxel is similar to docetaxel with characteristics, belongs to anti-microtubule class medicine.It is by with tubulin binding, promoting it to be assembled into microtubule, can stop these to assemble simultaneously microtubule disintegrate, make microtubule stable, so suppress cell mitotic division and interval cell function performance.
Crystal formation is one of important factor affected drug quality, curative effect and preparation processing performance.In view of the good curative effect of Cabazitaxel, people have carried out a lot of research to it, and have developed a lot of crystal formations.The Cabazitaxel crystal formation of existing bibliographical information is summed up roughly following a few class: solvate, anhydride, hydrate and amorphous article etc.At Cabazitaxel, in known crystal formation, WO2005028462 has reported crystal form A the earliest, and it is the acetone solvate form of Cabazitaxel, and the shortcoming of this crystal formation is unstable, and easily part removes acetone; Reported crystal form B, C, D, E, F in Chinese patent CN101918385 subsequently, all can be transformed by crystal form A.Wherein the B crystal form samples be the A crystal form samples at high temperature de-acetone obtain, the C crystal form samples is that A or B crystal form samples are carried out to maturation process in water, then under low humidity 0-5%RH condition, in 50 ℃ of heat dryings, obtains keeping; The D crystal form samples be the A crystal form samples in oil (neutral oil particularly, as: median chain triglyceride oil Miglyol) through heat treated, turn the crystal formation gained; The E crystal form samples is A crystal form samples maturation process in ethanol/water, then high temperature removal solvation gained; The F crystal form samples be by the A crystal form samples in the ethanol/water equal solvent through maturation process, then dryly under low moisture conditions remove that solvent obtains.Also reported the solvate of ethanol in Chinese patent CN101918385, the B of different crystal forms, D, E, F Cabazitaxel, in the saturated environment of alcohol vapour, through processing, obtain respectively B, D, E, the F new crystal of alcohol solvent simultaneously; This patent has also been reported the Cabazitaxel of monohydrate and dihydrate, by the C crystal form samples, under different ambient moisturies, obtains.Unformed Cabazitaxel, by Chinese patent CN102659722 report, is described according to this patent, and unformed Cabazitaxel can be transformed and obtain by the method for dissolving crystallization by the Cabazitaxel of any crystal formation.
In sum, we can find out that the preparation of all crystal formations of Cabazitaxel all needs specific environment to realize, be unfavorable for like this industrialization prepared by crystal formation, and in the preparation process of some crystal formation, adopt can cause the decline of product purity such as operations such as high temperature desolventizings, and some crystal formation itself is not just very stable, be easy to occur polymorphism, thereby can directly affect the preparation processing performance of medicine, and affect solubleness, stability and the bioavailability of medicine, and then have influence on quality, security, validity and the application of medicine.
Summary of the invention
In order to address the above problem, to the object of the present invention is to provide a kind of good stability and be beneficial to Cabazitaxel crystal formation W of suitability for industrialized production and preparation method thereof.
In order to achieve the above object, X-ray powder diffraction characteristic peak 2 θ of Cabazitaxel crystal formation W provided by the invention are 4.4,7.8,8.5,11.4,12.8,15.3,17.0,20.4,21.4,22.5,23.4,27.8, and 29.7,29.9,33.3 and 34.3 ± 0.2 °.
The preparation method of Cabazitaxel crystal formation W provided by the invention comprises the following step carried out in order:
1) Cabazitaxel of any crystal formation is dissolved in appropriate organic solvent, then slowly add wherein while stirring deionized water, organic solvent is selected from least one in methyl alcohol, ethanol, Virahol or acetonitrile, the volume ratio of organic solvent and water is 55:45-85:15, then be down to envrionment temperature, standing crystallization;
2) above-mentioned mixed solution filtration, washing drying are obtained to Cabazitaxel crystal formation W.
Described step 2) cleaning solvent in is water or water and pure mixed solvent, and drying temperature is 40-50 ℃.
Cabazitaxel crystal formation W provided by the invention compares aspect stable crystal form and has great advantage with the crystal formation of known patent bibliographical information, and the preparation process of this crystal formation is fairly simple, environment and equipment are not had to harsh requirement, repeatable strong, therefore be beneficial to suitability for industrialized production.
The accompanying drawing explanation
The X-ray powder diffraction that Fig. 1 is Cabazitaxel crystal formation W provided by the invention.
The DSC collection of illustrative plates that Fig. 2 is Cabazitaxel crystal formation W provided by the invention.
Embodiment
Detailed explanation the present invention below with reference to example, embodiments of the invention are only for technology bill of the present invention is described, and non-limiting the spirit and scope of the invention.
Test testing tool used:
1, x-ray diffraction pattern
Instrument model: Bruker D8 type X-ray powder diffraction instrument
Ray: Cu-K α
1(λ=1.54056)
Scan mode: 2 θ=2-40 °, 0.01 °/1sec
Voltage: 40KV-40mA
2, DCS instrument
Instrument model: TA instrument differential scanning calorimeter
Purging device: platinum dish, constant nitrogen gas stream
Temperature rise rate: 5 ℃/min
Temperature range: 30-300 ℃
Embodiment 1:
Taking Cabazitaxel pressed powder 500mg is dissolved in 10mL methyl alcohol, dropwise add wherein 5mL water under stirring, then be cooled to envrionment temperature, standing 24 hours crystallize outs, suction filtration, wash filter cake with water, obtains afterwards solid sample 490mg at the temperature of 40 ℃ after vacuum-drying, purity 99.7%, yield 95.6%.Utilize above-mentioned testing tool to be tested the X-ray of this sample, the X-ray diffraction spectrogram is shown in Fig. 1, the PXRD spectral characterization shows the characteristic peak that is positioned at 4.4,7.8,8.5,11.4,12.8,15.3,17.0,20.4,21.4,22.5,23.4,27.8,29.7,29.9,33.3 and 34.3 ± 0.2 ° of 2 θ, and being judged as this compound is Cabazitaxel crystal formation W.Its fusing point adopts the DSC instrument to measure, and the DSC spectrogram is shown in Fig. 2, and its fusing point is 153.78 ℃.
Embodiment 2:
Taking Cabazitaxel pressed powder 500mg is dissolved in 10mL ethanol, dropwise add wherein 5mL water under stirring, then be cooled to envrionment temperature, standing 24 hours crystallize outs, suction filtration, wash filter cake with water, obtains afterwards solid sample 492mg at the temperature of 45 ℃ after vacuum-drying, purity 99.2%, yield 98.4%.The X-ray diffraction spectrogram of this sample and DSC spectrogram, through comparative study, determine that this compound is Cabazitaxel crystal formation W.
Embodiment 3:
Taking Cabazitaxel pressed powder 500mg is dissolved in the 10mL Virahol, dropwise add wherein 5mL water under stirring, then be cooled to envrionment temperature, standing 24 hours crystallize outs, suction filtration, wash filter cake with water, obtains afterwards solid sample 460mg at the temperature of 50 ℃ after vacuum-drying, purity 99.3%, yield 92.0%.The X-ray diffraction spectrogram of this sample and DSC spectrogram, through comparative study, determine that this compound is Cabazitaxel crystal formation W.
Embodiment 4:
Taking Cabazitaxel pressed powder 500mg is dissolved in the 10mL acetonitrile, dropwise add wherein 5mL water under 50 ℃, then be cooled to envrionment temperature, standing 24 hours crystallize outs, suction filtration, wash filter cake with water, obtains afterwards solid sample 482mg at the temperature of 40 ℃ after vacuum-drying, purity 98.9%, yield 96.4%.The X-ray diffraction spectrogram of this sample and DSC spectrogram, through comparative study, determine that this compound is Cabazitaxel crystal formation W.
The Cabazitaxel crystal formation W outward appearance made by above-described embodiment is water white acicular crystals, and chemical stability is good, and after heat treated, the physical and chemical states of crystal and X-diffracting spectrum have no considerable change.The X-diffracting spectrum characteristic peak of this Cabazitaxel crystal formation W and known patent bibliographical information crystal formation and fusing point are compared and are seen following table 1.
Table 1
Claims (3)
1. a Cabazitaxel crystal formation W, it is characterized in that: X-ray powder diffraction characteristic peak 2 θ of described Cabazitaxel crystal formation W are 4.4,7.8,8.5,11.4,12.8,15.3,17.0,20.4,21.4,22.5,23.4,27.8,29.7,29.9,33.3 and 34.3 ± 0.2 °.
2. the preparation method of a Cabazitaxel crystal formation W claimed in claim 1, it is characterized in that: described preparation method comprises the following step carried out in order:
1) Cabazitaxel of any crystal formation is dissolved in appropriate organic solvent, then slowly add wherein while stirring deionized water, organic solvent is selected from least one in methyl alcohol, ethanol, Virahol or acetonitrile, the volume ratio of organic solvent and water is 55:45-85:15, then be down to envrionment temperature, standing crystallization;
2) above-mentioned mixed solution filtration, washing drying are obtained to Cabazitaxel crystal formation W.
3. preparation method according to claim 2 is characterized in that: the cleaning solvent described step 2) is water or water and pure mixed solvent, and drying temperature is 40-50 ℃.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105367521A (en) * | 2014-08-21 | 2016-03-02 | 中国医学科学院药物研究所 | Cabazitaxel N4 crystal form substance, and preparation method, composition and use thereof |
| CN105461665A (en) * | 2014-08-21 | 2016-04-06 | 中国医学科学院药物研究所 | Cabazitaxel N6 crystal form substance, and preparation method, composition and use thereof |
| CN105461664A (en) * | 2014-08-21 | 2016-04-06 | 中国医学科学院药物研究所 | Cabazitaxel N5 crystal form substance, and preparation method, composition and use thereof |
| CN108409691A (en) * | 2018-02-12 | 2018-08-17 | 江苏红豆杉药业有限公司 | A kind of Cabazitaxel crystal form HDC-1 and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101918385A (en) * | 2008-01-17 | 2010-12-15 | 安万特医药股份有限公司 | Crystalline forms of dimethoxy docetaxel and methods for preparing same |
| CN102746258A (en) * | 2012-07-25 | 2012-10-24 | 重庆泰濠制药有限公司 | Crystal forms of cabazitaxel and preparation method thereof |
| CN102898406A (en) * | 2012-11-02 | 2013-01-30 | 上海金和生物技术有限公司 | Cabazitaxel crystal and preparation method thereof |
| CN103058960A (en) * | 2012-12-12 | 2013-04-24 | 江苏奥赛康药业股份有限公司 | Cabazitaxel polymorphic form and preparation method thereof |
-
2013
- 2013-09-24 CN CN201310440458.4A patent/CN103450119B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101918385A (en) * | 2008-01-17 | 2010-12-15 | 安万特医药股份有限公司 | Crystalline forms of dimethoxy docetaxel and methods for preparing same |
| CN102746258A (en) * | 2012-07-25 | 2012-10-24 | 重庆泰濠制药有限公司 | Crystal forms of cabazitaxel and preparation method thereof |
| CN102898406A (en) * | 2012-11-02 | 2013-01-30 | 上海金和生物技术有限公司 | Cabazitaxel crystal and preparation method thereof |
| CN103058960A (en) * | 2012-12-12 | 2013-04-24 | 江苏奥赛康药业股份有限公司 | Cabazitaxel polymorphic form and preparation method thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105367521A (en) * | 2014-08-21 | 2016-03-02 | 中国医学科学院药物研究所 | Cabazitaxel N4 crystal form substance, and preparation method, composition and use thereof |
| CN105461665A (en) * | 2014-08-21 | 2016-04-06 | 中国医学科学院药物研究所 | Cabazitaxel N6 crystal form substance, and preparation method, composition and use thereof |
| CN105461664A (en) * | 2014-08-21 | 2016-04-06 | 中国医学科学院药物研究所 | Cabazitaxel N5 crystal form substance, and preparation method, composition and use thereof |
| CN108409691A (en) * | 2018-02-12 | 2018-08-17 | 江苏红豆杉药业有限公司 | A kind of Cabazitaxel crystal form HDC-1 and preparation method thereof |
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| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20171018 Granted publication date: 20150617 Pledgee: Bank of Tianjin, Limited by Share Ltd, Tianma subbranch Pledgor: Tianjin Weijie Technology Co., Ltd.|Tianjin Weijie Pharmaceutical Co., Ltd. Registration number: 2016990000880 |
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| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Cabazitaxel with crystal form W and method for preparing same Effective date of registration: 20171018 Granted publication date: 20150617 Pledgee: Bank of Tianjin, Limited by Share Ltd, Tianma subbranch Pledgor: Tianjin Weijie Technology Co., Ltd.|Tianjin Weijie Pharmaceutical Co., Ltd. Registration number: 2017990000966 |
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| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20181018 Granted publication date: 20150617 Pledgee: Bank of Tianjin, Limited by Share Ltd, Tianma subbranch Pledgor: Tianjin Weijie Technology Co., Ltd.|Tianjin Weijie Pharmaceutical Co., Ltd. Registration number: 2017990000966 |
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| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Cabazitaxel with crystal form W and method for preparing same Effective date of registration: 20181018 Granted publication date: 20150617 Pledgee: Bank of Tianjin, Limited by Share Ltd, Tianma subbranch Pledgor: Tianjin Weijie Technology Co., Ltd.|Tianjin Weijie Pharmaceutical Co., Ltd. Registration number: 2018990000977 |
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| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PM01 | Change of the registration of the contract for pledge of patent right |
Change date: 20210930 Registration number: 2018990000977 Pledgee after: Bank of Tianjin Co.,Ltd. second center sub branch Pledgee before: Bank of Tianjin Limited by Share Ltd. Tianma subbranch |
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| PM01 | Change of the registration of the contract for pledge of patent right |