CN102746258B - 卡巴他赛的结晶形式及其制备方法 - Google Patents
卡巴他赛的结晶形式及其制备方法 Download PDFInfo
- Publication number
- CN102746258B CN102746258B CN201210259595.3A CN201210259595A CN102746258B CN 102746258 B CN102746258 B CN 102746258B CN 201210259595 A CN201210259595 A CN 201210259595A CN 102746258 B CN102746258 B CN 102746258B
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- Prior art keywords
- cabazitaxel
- preparation
- crystal formation
- ethyl acetate
- carbonatoms
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- 229960001573 cabazitaxel Drugs 0.000 title claims abstract description 93
- 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 88
- 239000013078 crystal Substances 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- -1 ester compound Chemical class 0.000 claims abstract description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 47
- 230000015572 biosynthetic process Effects 0.000 claims description 46
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000012065 filter cake Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000002411 thermogravimetry Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 238000000967 suction filtration Methods 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- CHVARVMIVJJZTG-JVXKREHESA-N [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1-hydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate hydrate Chemical group O.CO[C@H]1C[C@H]2OC[C@@]2(OC(C)=O)[C@H]2[C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)c4ccccc4)C(C)=C([C@@H](OC)C(=O)[C@]12C)C3(C)C CHVARVMIVJJZTG-JVXKREHESA-N 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 15
- 230000001629 suppression Effects 0.000 abstract description 3
- 230000004913 activation Effects 0.000 abstract description 2
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- 230000001988 toxicity Effects 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000003915 cell function Effects 0.000 abstract 1
- 230000011278 mitosis Effects 0.000 abstract 1
- 201000007094 prostatitis Diseases 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 239000008213 purified water Substances 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 206010060862 Prostate cancer Diseases 0.000 description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000008859 change Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 229960003668 docetaxel Drugs 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 102000029749 Microtubule Human genes 0.000 description 2
- 108091022875 Microtubule Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 229960003328 benzoyl peroxide Drugs 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
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- 239000000976 ink Substances 0.000 description 2
- 230000016507 interphase Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 210000004688 microtubule Anatomy 0.000 description 2
- 230000000394 mitotic effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 239000003340 retarding agent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010062904 Hormone-refractory prostate cancer Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 206010027336 Menstruation delayed Diseases 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- 102000004243 Tubulin Human genes 0.000 description 1
- 108090000704 Tubulin Proteins 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001946 anti-microtubular Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000004683 dihydrates Chemical group 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229940014259 gelatin Drugs 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 239000003667 hormone antagonist Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 150000004682 monohydrates Chemical group 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 230000012106 negative regulation of microtubule depolymerization Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 230000004304 visual acuity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210259595.3A CN102746258B (zh) | 2012-07-25 | 2012-07-25 | 卡巴他赛的结晶形式及其制备方法 |
| CA2870569A CA2870569A1 (en) | 2012-07-25 | 2013-07-18 | Crystal form of cabazitaxel and preparation method thereof |
| EP16162975.3A EP3067348A1 (en) | 2012-07-25 | 2013-07-18 | Crystal form of cabazitaxel and preparation method thereof |
| PCT/CN2013/079575 WO2014015760A1 (zh) | 2012-07-25 | 2013-07-18 | 卡巴他赛的结晶形式及其制备方法 |
| CA2909500A CA2909500C (en) | 2012-07-25 | 2013-07-18 | Crystal form of cabazitaxel and preparation method thereof |
| US14/399,513 US9353076B2 (en) | 2012-07-25 | 2013-07-18 | Crystal form of cabazitaxel and preparation method thereof |
| EP13822828.3A EP2835369B1 (en) | 2012-07-25 | 2013-07-18 | Crystal form of cabazitaxel and preparation method thereof |
| IN1962MUN2014 IN2014MN01962A (enExample) | 2012-07-25 | 2013-07-18 | |
| JP2015514346A JP6329135B2 (ja) | 2012-07-25 | 2013-07-18 | カバジタキセルの結晶形態を有する結晶、その調製方法およびその使用 |
| AU2013295924A AU2013295924B2 (en) | 2012-07-25 | 2013-07-18 | Crystal form of cabazitaxel and preparation method thereof |
| AU2016200343A AU2016200343B2 (en) | 2012-07-25 | 2016-01-21 | Crystal form of cabazitaxel and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210259595.3A CN102746258B (zh) | 2012-07-25 | 2012-07-25 | 卡巴他赛的结晶形式及其制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102746258A CN102746258A (zh) | 2012-10-24 |
| CN102746258B true CN102746258B (zh) | 2015-02-04 |
Family
ID=47026807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210259595.3A Active CN102746258B (zh) | 2012-07-25 | 2012-07-25 | 卡巴他赛的结晶形式及其制备方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9353076B2 (enExample) |
| EP (2) | EP2835369B1 (enExample) |
| JP (1) | JP6329135B2 (enExample) |
| CN (1) | CN102746258B (enExample) |
| AU (2) | AU2013295924B2 (enExample) |
| CA (2) | CA2870569A1 (enExample) |
| IN (1) | IN2014MN01962A (enExample) |
| WO (1) | WO2014015760A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2688877B1 (en) | 2011-04-12 | 2017-03-08 | Teva Pharmaceuticals International GmbH | Solid state forms of cabazitaxel and processes for preparation thereof |
| CN104220431A (zh) * | 2012-03-08 | 2014-12-17 | 伊瓦克斯国际有限责任公司 | 卡巴他赛的固态形式及其制备方法 |
| CN102746258B (zh) * | 2012-07-25 | 2015-02-04 | 重庆泰濠制药有限公司 | 卡巴他赛的结晶形式及其制备方法 |
| CN103804323A (zh) * | 2012-11-14 | 2014-05-21 | 上海希迈医药科技有限公司 | 一种卡巴他赛溶剂化物及其制备方法和应用 |
| CN103819428B (zh) * | 2012-11-19 | 2016-01-13 | 齐鲁制药有限公司 | 7β,10β-二甲氧基多西紫杉醇的溶剂化物的晶型及其制备方法 |
| CN103058960B (zh) * | 2012-12-12 | 2014-12-10 | 江苏奥赛康药业股份有限公司 | 卡巴他赛多晶型形式及其制备方法 |
| KR101429543B1 (ko) | 2012-12-13 | 2014-08-14 | 주식회사 삼양바이오팜 | 카바지탁셀의 신규 결정형 및 그 제조방법 |
| CN103044364B (zh) * | 2013-01-07 | 2016-01-20 | 重庆泰濠制药有限公司 | 一种卡巴他赛无定形晶及其制备方法 |
| WO2014128728A2 (en) * | 2013-02-25 | 2014-08-28 | Laurus Labs Private Limited | Solid forms of cabazitaxel and processes for preparation thereof |
| CN103450119B (zh) * | 2013-09-24 | 2015-06-17 | 天津炜捷制药有限公司 | 一种卡巴他赛晶型w及其制备方法 |
| EP2865674A1 (en) * | 2013-10-23 | 2015-04-29 | INDENA S.p.A. | Crystalline solvate forms of Cabazitaxel |
| CN105461664A (zh) * | 2014-08-21 | 2016-04-06 | 中国医学科学院药物研究所 | 卡巴他赛晶n5型物质及制备方法和其组合物与用途 |
| CN105461665A (zh) * | 2014-08-21 | 2016-04-06 | 中国医学科学院药物研究所 | 卡巴他赛晶n6型物质及制备方法和其组合物与用途 |
| CA3010514A1 (en) | 2016-01-15 | 2017-07-20 | Zhuhai Beihai Biotech Co., Ltd. | Compositions and formulations including cabazitaxel and human serum albumin |
| EP3509569A1 (en) * | 2016-09-07 | 2019-07-17 | Cadila Healthcare Limited | Sterile injectable compositions comprising drug micelles |
| CN112055588B (zh) | 2018-04-20 | 2023-09-08 | 珠海贝海生物技术有限公司 | 卡巴他赛的制剂和组合物 |
| CN113429369B (zh) * | 2021-07-23 | 2022-12-02 | 无锡紫杉药业有限公司 | 一种高效的卡巴他赛纯化方法 |
Family Cites Families (19)
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|---|---|---|---|---|
| SK9742002A3 (en) | 2000-01-07 | 2003-02-04 | Transform Pharmaceuticals Inc | High-throughput formation, identification, and analysis of diverse solid-forms |
| FR2859996B1 (fr) * | 2003-09-19 | 2006-02-03 | Aventis Pharma Sa | Solvat acetonique du dimethoxy docetaxel et son procede de preparation |
| FR2926551A1 (fr) * | 2008-01-17 | 2009-07-24 | Aventis Pharma Sa | Formes cristallines du dimethoxy docetaxel et leurs procedes de preparation |
| CN101525321B (zh) * | 2008-03-06 | 2012-03-07 | 上海希迪制药有限公司 | 多烯紫杉醇倍半水结晶体及其制备方法 |
| PL388144A1 (pl) | 2009-05-29 | 2010-12-06 | Przedsiębiorstwo Produkcyjno-Wdrożeniowe Ifotam Spółka Z Ograniczoną Odpowiedzialnością | Solwaty (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylopropionianu 4-acetoksy-2α-benzoiloksy -5β,20-epoksy-1,7β,10β-trihydroksy-9-okso-taks-11-en-13α-ylu, sposób ich otrzymywania i zastosowanie |
| CN102060815B (zh) * | 2010-12-24 | 2012-09-26 | 重庆泰濠制药有限公司 | 一种紫杉烷类化合物的制备方法 |
| EP2688877B1 (en) * | 2011-04-12 | 2017-03-08 | Teva Pharmaceuticals International GmbH | Solid state forms of cabazitaxel and processes for preparation thereof |
| TWI526437B (zh) | 2011-09-09 | 2016-03-21 | 台灣神隆股份有限公司 | 卡巴他賽之結晶型 |
| CN102336726B (zh) * | 2011-09-30 | 2014-11-26 | 重庆泰濠制药有限公司 | 一种卡巴他赛的制备方法 |
| US9772339B2 (en) * | 2011-09-30 | 2017-09-26 | Life Technologies Corporation | Methods and systems for image analysis identification |
| CN102503913B (zh) * | 2011-10-20 | 2014-03-26 | 江苏红豆杉生物科技股份有限公司 | 直接用于x射线单晶衍射分析的二甲氧基紫杉烷类化合物单晶晶体的制备方法 |
| DE112012004569T5 (de) * | 2011-11-01 | 2014-08-14 | Fresenius Kabi Oncology Ltd. | Amorphe Form von Cabazitaxel und Verfahren zum Herstellen davon |
| PL2785701T3 (pl) * | 2011-11-28 | 2019-08-30 | Fresenius Kabi Oncology Limited | Krystaliczna postać kabazytakselu i sposób jej otrzymywania |
| JP6025861B2 (ja) * | 2011-12-13 | 2016-11-16 | アベンティス・ファーマ・ソシエテ・アノニム | カバジタキセルの結晶形およびこれを調製するための方法 |
| CN104220431A (zh) * | 2012-03-08 | 2014-12-17 | 伊瓦克斯国际有限责任公司 | 卡巴他赛的固态形式及其制备方法 |
| CN102746258B (zh) | 2012-07-25 | 2015-02-04 | 重庆泰濠制药有限公司 | 卡巴他赛的结晶形式及其制备方法 |
| CN104583189A (zh) * | 2012-07-31 | 2015-04-29 | 永信药品工业股份有限公司 | 非晶型的卡巴利他索 |
| CN102898406B (zh) * | 2012-11-02 | 2014-12-03 | 上海金和生物技术有限公司 | 一种卡巴他赛晶体及其制备方法 |
| CN103058960B (zh) * | 2012-12-12 | 2014-12-10 | 江苏奥赛康药业股份有限公司 | 卡巴他赛多晶型形式及其制备方法 |
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| JP6329135B2 (ja) | 2018-05-23 |
| CA2909500C (en) | 2018-01-09 |
| EP2835369A1 (en) | 2015-02-11 |
| AU2016200343A1 (en) | 2016-02-11 |
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