CN100546985C - 非布他特微晶及其组合物 - Google Patents
非布他特微晶及其组合物 Download PDFInfo
- Publication number
- CN100546985C CN100546985C CNB2007100431784A CN200710043178A CN100546985C CN 100546985 C CN100546985 C CN 100546985C CN B2007100431784 A CNB2007100431784 A CN B2007100431784A CN 200710043178 A CN200710043178 A CN 200710043178A CN 100546985 C CN100546985 C CN 100546985C
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- China
- Prior art keywords
- febuxotat
- microcrystal
- preparation
- composition
- dissolution rate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 239000013081 microcrystal Substances 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000007787 solid Substances 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000002245 particle Substances 0.000 claims description 8
- 239000002775 capsule Substances 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 6
- 238000002050 diffraction method Methods 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 238000001228 spectrum Methods 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 229910002483 Cu Ka Inorganic materials 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 abstract description 15
- 238000004090 dissolution Methods 0.000 abstract description 15
- 239000010419 fine particle Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 3
- 239000012467 final product Substances 0.000 abstract description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 13
- 239000013078 crystal Substances 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 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 3
- 238000004458 analytical method Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910017488 Cu K Inorganic materials 0.000 description 2
- 229910017541 Cu-K Inorganic materials 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000011194 food seasoning agent Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 229940032147 starch Drugs 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 1
- 229920002785 Croscarmellose sodium 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
- 239000001828 Gelatine Substances 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 229920003081 Povidone K 30 Polymers 0.000 description 1
- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- BQSJTQLCZDPROO-UHFFFAOYSA-N febuxostat Chemical group C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)S1 BQSJTQLCZDPROO-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical class OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000008201 pharmaceutical excipient composition Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000001253 polyvinylpolypyrrolidone Substances 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 235000020985 whole grains Nutrition 0.000 description 1
- 239000003064 xanthine oxidase inhibitor Substances 0.000 description 1
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Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2007100431784A CN100546985C (zh) | 2007-06-29 | 2007-06-29 | 非布他特微晶及其组合物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2007100431784A CN100546985C (zh) | 2007-06-29 | 2007-06-29 | 非布他特微晶及其组合物 |
Publications (2)
Publication Number | Publication Date |
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CN101085761A CN101085761A (zh) | 2007-12-12 |
CN100546985C true CN100546985C (zh) | 2009-10-07 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CNB2007100431784A Expired - Fee Related CN100546985C (zh) | 2007-06-29 | 2007-06-29 | 非布他特微晶及其组合物 |
Country Status (1)
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CN (1) | CN100546985C (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010144685A1 (en) | 2009-06-10 | 2010-12-16 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of febuxostat |
WO2012007487A1 (en) | 2010-07-13 | 2012-01-19 | Interquim, S.A. | Process for preparing the crystalline form ii of febuxostat |
WO2013088449A1 (en) | 2011-12-16 | 2013-06-20 | Natco Pharma Limited | Stable crystal form of febuxostat and process for the preparation thereof |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101716132B (zh) * | 2008-10-09 | 2012-01-11 | 北京方策方程医药科技有限公司 | 非布索坦肠溶制剂 |
CN101781270B (zh) * | 2009-01-20 | 2013-03-27 | 重庆医药工业研究院有限责任公司 | 一种高纯度的非布司他及其制备方法 |
CN101780073B (zh) * | 2009-01-21 | 2013-07-03 | 重庆圣华曦药业股份有限公司 | 非布司他分散片药物及其制备方法 |
CN103936689B (zh) * | 2009-07-17 | 2016-08-17 | 北京利乐生制药科技有限公司 | 2-[3-氰基-4-异丁氧基苯基]-4-甲基噻唑-5-甲酸晶型及其制备方法 |
CN101817801A (zh) * | 2009-08-12 | 2010-09-01 | 北京红惠新医药科技有限公司 | 2-(3-氰基-4-异丁氧基苯基)-4-甲基-5-噻唑甲酸新晶型k及其他晶型的制备方法 |
CN102070558B (zh) * | 2009-11-23 | 2012-08-22 | 欣凯医药化工中间体(上海)有限公司 | 非布索坦的新晶型及其制备方法 |
WO2011080651A2 (en) | 2009-12-31 | 2011-07-07 | Ranbaxy Laboratories Limited | Polymorphic forms of febuxostat |
CA2792036A1 (en) | 2010-03-04 | 2011-09-09 | Ranbaxy Laboratories Limited | Polymorph of 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid |
CN101824005B (zh) * | 2010-04-27 | 2012-06-27 | 上海凯米侬医药科技有限公司 | 一种非布索坦的晶型q及其制备方法 |
TW201217347A (en) * | 2010-07-13 | 2012-05-01 | Interquim Sa | Process for preparing the crystalline form a of febuxostat |
US20130190368A1 (en) | 2010-09-24 | 2013-07-25 | Hetero Research Foundation | Novel polymorphs of febuxostat |
US20140112992A1 (en) | 2011-06-06 | 2014-04-24 | Hetero Research Foundation | Process for febuxostat |
JP2014533297A (ja) * | 2011-11-15 | 2014-12-11 | マイラン ラボラトリーズ リミテッドMylan Laboratories Limited | フェブキソスタットの多形の調製方法 |
EP2692342A1 (en) | 2012-07-30 | 2014-02-05 | Interquim, S.A. | Process for the preparation of pharmaceutical compositions comprising febuxostat in the form of tablets |
EP3153158A1 (de) | 2015-10-09 | 2017-04-12 | Stada Arzneimittel Ag | Orale febuxostat-tablette |
-
2007
- 2007-06-29 CN CNB2007100431784A patent/CN100546985C/zh not_active Expired - Fee Related
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010144685A1 (en) | 2009-06-10 | 2010-12-16 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of febuxostat |
JP2012529537A (ja) * | 2009-06-10 | 2012-11-22 | テバ ファーマシューティカル インダストリーズ リミティド | フェブキソスタットの結晶形 |
EP2532654A1 (en) | 2009-06-10 | 2012-12-12 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of febuxostat |
US8415481B2 (en) | 2009-06-10 | 2013-04-09 | Teva Pharmaceuticals Usa, Inc. | Crystalline form of febuxostat |
US8609856B2 (en) | 2009-06-10 | 2013-12-17 | Teva Pharmaceuticals Usa, Inc. | Crystalline forms of Febuxostat |
US8742129B2 (en) | 2009-06-10 | 2014-06-03 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of febuxostat |
WO2012007487A1 (en) | 2010-07-13 | 2012-01-19 | Interquim, S.A. | Process for preparing the crystalline form ii of febuxostat |
WO2013088449A1 (en) | 2011-12-16 | 2013-06-20 | Natco Pharma Limited | Stable crystal form of febuxostat and process for the preparation thereof |
Also Published As
Publication number | Publication date |
---|---|
CN101085761A (zh) | 2007-12-12 |
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EE01 | Entry into force of recordation of patent licensing contract |
Assignee: QIDONG HUATUO PHARMACEUTICAL Co.,Ltd. Assignor: Shanghai Huatuo Medical Science Co.,Ltd. Contract record no.: 2011310000023 Denomination of invention: Febuxotat microcrystal and compositions thereof Granted publication date: 20091007 License type: Exclusive License Open date: 20071212 Record date: 20110323 |
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C56 | Change in the name or address of the patentee |
Owner name: SHANGHAI HUATUO MEDICINE SCI-TECH DEVELOPMENT CO., Free format text: FORMER NAME: SHANGHAI HUATUO MEDICAL SCIENCE CO., LTD. |
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Address after: 200093 No. 90, Shulan Road, Shanghai, Yangpu District Patentee after: SHANGHAI HOTMED SCIENCES Co.,Ltd. Address before: 200093 No. 90, Shulan Road, Shanghai, Yangpu District Patentee before: Shanghai Huatuo Medical Science Co.,Ltd. |
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Change date: 20150226 Contract record no.: 2011310000023 Assignor after: SHANGHAI HOTMED SCIENCES Co.,Ltd. Assignor before: Shanghai Huatuo Medical Science Co.,Ltd. |
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Effective date of registration: 20181128 Address after: 226221 No. 88 Jiangsu Road, Binjiang Fine Chemical Park, Qidong Economic Development Zone, Nantong City, Jiangsu Province Patentee after: QIDONG HUATUO PHARMACEUTICAL Co.,Ltd. Address before: 200093 No. 90, Shulan Road, Shanghai, Yangpu District Patentee before: SHANGHAI HOTMED SCIENCES Co.,Ltd. |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20091007 |