CN102887829A - 芬戈莫德粘酸盐及其晶体的制备方法和用途 - Google Patents
芬戈莫德粘酸盐及其晶体的制备方法和用途 Download PDFInfo
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- CN102887829A CN102887829A CN2012103261644A CN201210326164A CN102887829A CN 102887829 A CN102887829 A CN 102887829A CN 2012103261644 A CN2012103261644 A CN 2012103261644A CN 201210326164 A CN201210326164 A CN 201210326164A CN 102887829 A CN102887829 A CN 102887829A
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- 239000013078 crystal Substances 0.000 title claims abstract description 52
- 229960000556 fingolimod Drugs 0.000 title claims abstract description 17
- KKGQTZUTZRNORY-UHFFFAOYSA-N fingolimod Chemical compound CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 KKGQTZUTZRNORY-UHFFFAOYSA-N 0.000 title claims abstract 16
- 238000000034 method Methods 0.000 title claims description 13
- 239000003814 drug Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 14
- 239000003937 drug carrier Substances 0.000 claims abstract description 4
- 239000002955 immunomodulating agent Substances 0.000 claims abstract description 3
- 229940121354 immunomodulator Drugs 0.000 claims abstract description 3
- 230000002584 immunomodulator Effects 0.000 claims abstract description 3
- DUYSYHSSBDVJSM-KRWOKUGFSA-N sphingosine 1-phosphate Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O DUYSYHSSBDVJSM-KRWOKUGFSA-N 0.000 claims abstract 4
- 230000015572 biosynthetic process Effects 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
- 230000005260 alpha ray Effects 0.000 claims description 8
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 8
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229940075993 receptor modulator Drugs 0.000 abstract 1
- SWZTYAVBMYWFGS-UHFFFAOYSA-N fingolimod hydrochloride Chemical compound Cl.CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 SWZTYAVBMYWFGS-UHFFFAOYSA-N 0.000 description 80
- 238000005755 formation reaction Methods 0.000 description 27
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 4
- 239000008108 microcrystalline cellulose Substances 0.000 description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 description 4
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- 238000001069 Raman spectroscopy Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000001237 Raman spectrum Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000000527 lymphocytic effect Effects 0.000 description 2
- 210000003563 lymphoid tissue Anatomy 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NVZOQWXXQVFFOL-UHFFFAOYSA-N CCCC(CCCC)C(C)C(C(O)O)(C)N Chemical compound CCCC(CCCC)C(C)C(C(O)O)(C)N NVZOQWXXQVFFOL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 description 1
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000001861 immunosuppressant effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Transplantation (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
芬戈莫德粘酸盐 | 2.1mg |
微晶纤维 | 115.5mg |
硬脂酸镁 | 2.4mg |
总计 | 120mg |
芬戈莫德粘酸盐 | 1.7mg |
微晶纤维 | 113.9mg |
羟丙基纤维素 | 3.6mg |
硬脂酸镁 | 1.8mg |
总计 | 120mg |
考察条件 | 样品 | 0周 | 2周 | 4周 | 6周 |
80℃/75%RH | FTY720 | 99.8% | 97.0% | 96.3% | 96.5% |
芬戈莫德粘酸盐 | 99.2% | 99.5% | 99.1% | 99.4% | |
80℃ | FTY720 | 99.8% | 99.5% | 99.3% | 99.5% |
芬戈莫德粘酸盐 | 99.2% | 99.3% | 99.4% | 99.4% |
Claims (7)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210326164.4A CN102887829B (zh) | 2012-09-05 | 2012-09-05 | 芬戈莫德粘酸盐及其晶体的制备方法和用途 |
PCT/CN2013/080393 WO2014036865A1 (zh) | 2012-09-05 | 2013-07-30 | 芬戈莫德粘酸盐及其晶体的制备方法和用途 |
Applications Claiming Priority (1)
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CN201210326164.4A CN102887829B (zh) | 2012-09-05 | 2012-09-05 | 芬戈莫德粘酸盐及其晶体的制备方法和用途 |
Publications (2)
Publication Number | Publication Date |
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CN102887829A true CN102887829A (zh) | 2013-01-23 |
CN102887829B CN102887829B (zh) | 2014-07-02 |
Family
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CN201210326164.4A Active CN102887829B (zh) | 2012-09-05 | 2012-09-05 | 芬戈莫德粘酸盐及其晶体的制备方法和用途 |
Country Status (2)
Country | Link |
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CN (1) | CN102887829B (zh) |
WO (1) | WO2014036865A1 (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014036865A1 (zh) * | 2012-09-05 | 2014-03-13 | 中国科学院上海药物研究所 | 芬戈莫德粘酸盐及其晶体的制备方法和用途 |
CN104146991A (zh) * | 2014-04-04 | 2014-11-19 | 施福东 | 芬戈莫德及其结构类似物用于制备治疗脑梗死药物的应用 |
CN110612292A (zh) * | 2017-04-07 | 2019-12-24 | 杭州领业医药科技有限公司 | 奥扎莫德加成盐晶型、制备方法及药物组合物和用途 |
WO2022253077A1 (zh) * | 2021-05-31 | 2022-12-08 | 上海博志研新药物技术有限公司 | 芬戈莫德药用盐、制备方法、含其的药物组合物及应用 |
Citations (6)
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---|---|---|---|---|
CN101068536A (zh) * | 2004-11-29 | 2007-11-07 | 诺瓦提斯公司 | S1p受体激动剂的剂量方案 |
WO2008000419A1 (en) * | 2006-06-27 | 2008-01-03 | Novartis Ag | S1p receptor modulators for treating multiple sclerosis |
WO2010055027A2 (en) * | 2008-11-11 | 2010-05-20 | Novartis Ag | Organic compounds |
CN102120720A (zh) * | 2011-01-25 | 2011-07-13 | 上海华升生物科技有限公司 | 盐酸芬戈莫德的合成新方法 |
WO2012071524A1 (en) * | 2010-11-24 | 2012-05-31 | Ratiopharm Gmbh | Arylsulfonate salts of fingolimod and processes for preparation thereof |
WO2012070059A1 (en) * | 2010-11-25 | 2012-05-31 | Shilpa Medicare Limited | Fingolimod polymorphs and their processes |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8318812B2 (en) * | 2006-06-02 | 2012-11-27 | The Ohio State University Research Foundation | Therapeutic agents for the treatment of lymphoid malignancies |
EP2356090B1 (en) * | 2008-11-11 | 2017-07-05 | Novartis AG | Crystalline forms of fingolimod hcl |
PT2621889T (pt) * | 2010-10-01 | 2019-10-30 | Synthon Bv | Processo para produzir cristais de cloridrato de fingolimod |
CN102887829B (zh) * | 2012-09-05 | 2014-07-02 | 中国科学院上海药物研究所 | 芬戈莫德粘酸盐及其晶体的制备方法和用途 |
-
2012
- 2012-09-05 CN CN201210326164.4A patent/CN102887829B/zh active Active
-
2013
- 2013-07-30 WO PCT/CN2013/080393 patent/WO2014036865A1/zh active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101068536A (zh) * | 2004-11-29 | 2007-11-07 | 诺瓦提斯公司 | S1p受体激动剂的剂量方案 |
WO2008000419A1 (en) * | 2006-06-27 | 2008-01-03 | Novartis Ag | S1p receptor modulators for treating multiple sclerosis |
WO2010055027A2 (en) * | 2008-11-11 | 2010-05-20 | Novartis Ag | Organic compounds |
WO2012071524A1 (en) * | 2010-11-24 | 2012-05-31 | Ratiopharm Gmbh | Arylsulfonate salts of fingolimod and processes for preparation thereof |
WO2012070059A1 (en) * | 2010-11-25 | 2012-05-31 | Shilpa Medicare Limited | Fingolimod polymorphs and their processes |
CN102120720A (zh) * | 2011-01-25 | 2011-07-13 | 上海华升生物科技有限公司 | 盐酸芬戈莫德的合成新方法 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014036865A1 (zh) * | 2012-09-05 | 2014-03-13 | 中国科学院上海药物研究所 | 芬戈莫德粘酸盐及其晶体的制备方法和用途 |
CN104146991A (zh) * | 2014-04-04 | 2014-11-19 | 施福东 | 芬戈莫德及其结构类似物用于制备治疗脑梗死药物的应用 |
CN110612292A (zh) * | 2017-04-07 | 2019-12-24 | 杭州领业医药科技有限公司 | 奥扎莫德加成盐晶型、制备方法及药物组合物和用途 |
WO2022253077A1 (zh) * | 2021-05-31 | 2022-12-08 | 上海博志研新药物技术有限公司 | 芬戈莫德药用盐、制备方法、含其的药物组合物及应用 |
CN115477590A (zh) * | 2021-05-31 | 2022-12-16 | 上海博志研新药物技术有限公司 | 芬戈莫德药用盐、制备方法、含其的药物组合物及应用 |
CN115477590B (zh) * | 2021-05-31 | 2023-12-12 | 上海云晟研新生物科技有限公司 | 芬戈莫德药用盐、制备方法、含其的药物组合物及应用 |
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CN102887829B (zh) | 2014-07-02 |
WO2014036865A1 (zh) | 2014-03-13 |
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