JP2013516473A5 - - Google Patents
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- Publication number
- JP2013516473A5 JP2013516473A5 JP2012548092A JP2012548092A JP2013516473A5 JP 2013516473 A5 JP2013516473 A5 JP 2013516473A5 JP 2012548092 A JP2012548092 A JP 2012548092A JP 2012548092 A JP2012548092 A JP 2012548092A JP 2013516473 A5 JP2013516473 A5 JP 2013516473A5
- Authority
- JP
- Japan
- Prior art keywords
- acetate
- cyclopropylnaphthalen
- ylthio
- triazol
- bromo
- 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.)
- Granted
Links
- 239000004480 active ingredient Substances 0.000 claims 28
- FVYMVLTWIBGEMC-UHFFFAOYSA-M sodium;2-[[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-1,2,4-triazol-3-yl]sulfanyl]acetate Chemical compound [Na+].[O-]C(=O)CSC1=NN=C(Br)N1C(C1=CC=CC=C11)=CC=C1C1CC1 FVYMVLTWIBGEMC-UHFFFAOYSA-M 0.000 claims 27
- 238000000634 powder X-ray diffraction Methods 0.000 claims 17
- 239000007787 solid Substances 0.000 claims 16
- -1 4-cyclopropylnaphthalen-1-yl Chemical group 0.000 claims 11
- 238000000113 differential scanning calorimetry Methods 0.000 claims 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 8
- 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 claims 8
- 239000011734 sodium Substances 0.000 claims 8
- 229910052708 sodium Inorganic materials 0.000 claims 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 201000005569 Gout Diseases 0.000 claims 2
- 201000001431 Hyperuricemia Diseases 0.000 claims 2
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229940116269 uric acid Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29360210P | 2010-01-08 | 2010-01-08 | |
| US61/293,602 | 2010-01-08 | ||
| PCT/US2011/020233 WO2011085009A2 (en) | 2010-01-08 | 2011-01-05 | Polymorphic, crystalline and mesophase forms of sodium 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-ylthio)acetate, and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013516473A JP2013516473A (ja) | 2013-05-13 |
| JP2013516473A5 true JP2013516473A5 (enExample) | 2013-07-25 |
| JP5696346B2 JP5696346B2 (ja) | 2015-04-08 |
Family
ID=44306123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012548092A Expired - Fee Related JP5696346B2 (ja) | 2010-01-08 | 2011-01-05 | ナトリウム２−（５−ブロモ−４−（４−シクロプロピルナフタレン−１−イル）−４ｈ−１，２，４−トリアゾル−３−イルチオ）アセテートの多形性、結晶性、および、中間相の形態と、その使用 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US8524754B2 (enExample) |
| EP (1) | EP2521716B1 (enExample) |
| JP (1) | JP5696346B2 (enExample) |
| KR (1) | KR20120104627A (enExample) |
| CN (1) | CN102741234B (enExample) |
| AU (1) | AU2011203708B2 (enExample) |
| BR (1) | BR112012016795A2 (enExample) |
| CA (1) | CA2785200C (enExample) |
| CL (1) | CL2012001841A1 (enExample) |
| CO (1) | CO6561780A2 (enExample) |
| EA (1) | EA020183B1 (enExample) |
| ES (1) | ES2563207T3 (enExample) |
| MX (1) | MX2012007925A (enExample) |
| MY (1) | MY161482A (enExample) |
| NZ (1) | NZ600984A (enExample) |
| PH (1) | PH12012501391A1 (enExample) |
| SG (1) | SG182404A1 (enExample) |
| TW (1) | TWI451867B (enExample) |
| WO (1) | WO2011085009A2 (enExample) |
| ZA (1) | ZA201204938B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9402827B2 (en) | 2010-03-30 | 2016-08-02 | Ardea Biosciences, Inc. | Treatment of gout |
| US9216179B2 (en) * | 2010-06-15 | 2015-12-22 | Ardea Biosciences, Inc. | Treatment of gout and hyperuricemia |
| EP2658846B1 (en) * | 2010-12-30 | 2016-12-14 | Ardea Biosciences, Inc. | Polymorphic forms of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-ylthio) acetic acid and uses thereof |
| EP2776028B1 (en) | 2011-11-03 | 2018-10-17 | Ardea Biosciences, Inc. | 3,4-di-substituted pyridine compound, methods of using and compositions comprising the same |
| AR091651A1 (es) * | 2012-07-03 | 2015-02-18 | Ardea Biosciences Inc | Elaboracion de acido 2-(5-bromo-4-(4-ciclopropilnaftalen-1-il)-4h-1,2,4-triazol-3-iltio)acetico |
| CN103524440B (zh) * | 2013-10-15 | 2015-09-09 | 苏州鹏旭医药科技有限公司 | 痛风治疗药Lesinurad的制备方法及Lesinurad中间体 |
| CN103588716A (zh) * | 2013-11-22 | 2014-02-19 | 苏州晶云药物科技有限公司 | 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1，2，4-三唑-3-基硫基)乙酸的新晶型及其制备方法 |
| US10351536B2 (en) * | 2013-11-22 | 2019-07-16 | Crystal Pharmatech Co., Ltd. | Crystalline forms of lesinurad and its sodium salt |
| CN103613552A (zh) * | 2013-12-02 | 2014-03-05 | 苏州晶云药物科技有限公司 | 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1，2，4-三唑-3-基硫基)乙酸钠的新晶型及其制备方法 |
| CN103755651A (zh) * | 2013-12-23 | 2014-04-30 | 苏州晶云药物科技有限公司 | 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1，2，4-三唑-3-基硫基)乙酸的盐的新晶型及其制备方法 |
| WO2015095703A1 (en) | 2013-12-20 | 2015-06-25 | Crystal Pharmatech, Inc. | Novel salts and co-crystals of lesinurad |
| CN103626710A (zh) * | 2013-12-20 | 2014-03-12 | 苏州晶云药物科技有限公司 | 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1，2，4-三唑-3-基硫基)乙酸的共晶及其制备方法 |
| CN105315218A (zh) * | 2014-07-17 | 2016-02-10 | 天津药物研究院 | 一种制备lesinurad中间体1-萘基三唑硫酮的方法 |
| CN105622427A (zh) * | 2014-10-31 | 2016-06-01 | 天津药物研究院有限公司 | 一种制备lesinurad中间体4-环丙基-1-萘胺的方法 |
| CN105820130B (zh) * | 2015-01-08 | 2018-06-22 | 天津药物研究院有限公司 | 三氮唑正丙酸类urat1抑制剂、制备方法及其在高尿酸血症和痛风治疗上的用途 |
| CN105985296B (zh) * | 2015-02-13 | 2018-10-16 | 天津药物研究院有限公司 | 一种可以工业化的lesinurad中间体1-萘基三唑硫酮的精制工艺 |
| CN105622531A (zh) | 2015-04-03 | 2016-06-01 | 南京明德新药研发股份有限公司 | 轴手性异构体及其制备方法和制药用途 |
| CN104817509B (zh) * | 2015-04-13 | 2019-05-17 | 安徽省逸欣铭医药科技有限公司 | Lesinurad类似物及其制备方法和医药用途 |
| CN106187926B (zh) | 2015-04-30 | 2018-11-27 | 天津药物研究院有限公司 | 含二芳基甲烷结构的羧酸类urat1抑制剂、制备方法及其在高尿酸血症和痛风治疗上的用途 |
| EP3112334A1 (en) | 2015-06-29 | 2017-01-04 | DPx Fine Chemicals Austria GmbH & CoKG | Process for manufacturing 1-cyclopropyl-naphthalenes |
| CN104987311A (zh) * | 2015-06-30 | 2015-10-21 | 安徽万邦医药科技有限公司 | 一种[4-(4-环丙基萘-1-基)-5-硝基- 4h-[1,2,4]三唑-3-基硫烷基]-乙酸乙酯的制备方法及其中间体(5-硝基-4h-[1,2,4]三唑-3-基硫基)-乙酸乙酯 |
| CN105017168A (zh) * | 2015-07-01 | 2015-11-04 | 安徽万邦医药科技有限公司 | 一种[5-溴-4-(4-环丙基萘-1-基)-4h-[1,2,4]三唑-3-基硫烷基]-乙酸甲酯的新制备方法 |
| CN105153056A (zh) * | 2015-07-01 | 2015-12-16 | 安徽万邦医药科技有限公司 | 一种[5-溴-4-(4-环丙基萘-1-基)-4h-[1,2,4]三唑-3-基硫烷基]-乙酸甲酯的新制备方法 |
| WO2017036884A1 (en) | 2015-08-28 | 2017-03-09 | Sandoz Ag | A lesinurad, free form / lesinurad ethyl ester co-crystal |
| CN105566237B (zh) * | 2016-03-01 | 2018-05-18 | 山东大学 | 一种治疗痛风的三唑巯乙酸类化合物的制备方法 |
| CN107337649B (zh) * | 2016-04-29 | 2020-10-16 | 四川科伦药物研究院有限公司 | 一种乙酸钠水合物无定型及其制备方法和用途 |
| EP3281941B1 (en) | 2016-08-11 | 2019-07-24 | Zentiva K.S. | Process for preparing 2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4h-1,2,4-triazol-3-ylthio)acetic acid |
| US10513500B2 (en) | 2016-11-10 | 2019-12-24 | Apotex Inc. | Crystalline forms of Lesinurad |
| CN106632108A (zh) * | 2016-12-14 | 2017-05-10 | 湖南欧亚生物有限公司 | 一种来司诺雷的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE528001T1 (de) | 2004-08-25 | 2011-10-15 | Ardea Biosciences Inc | S-triazolyl-alpha-mercaptoacetanilide als inhibitoren von hiv-umkehrtranskriptase |
| WO2007050087A1 (en) | 2004-08-25 | 2007-05-03 | Ardea Biosciences, Inc. | N[S(4-aryl-triazol-3-yl)α -mercaptoacetyl]-p-amino benozoic acids AS HIV REVERSE TRANSCRIPTASE INHIBITORS |
| NZ595035A (en) | 2007-11-27 | 2012-11-30 | Ardea Biosciences Inc | Substituted diazole and triazole compounds and compositions and methods of use |
| JP2012502049A (ja) | 2008-09-04 | 2012-01-26 | アルディア バイオサイエンス，インク． | 尿酸値を調節するための化合物、組成物及びそれを使用する方法。 |
| EP2658846B1 (en) | 2010-12-30 | 2016-12-14 | Ardea Biosciences, Inc. | Polymorphic forms of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-ylthio) acetic acid and uses thereof |
-
2011
- 2011-01-05 SG SG2012050100A patent/SG182404A1/en unknown
- 2011-01-05 NZ NZ600984A patent/NZ600984A/xx not_active IP Right Cessation
- 2011-01-05 ES ES11732089.5T patent/ES2563207T3/es active Active
- 2011-01-05 CN CN201180005688.7A patent/CN102741234B/zh not_active Expired - Fee Related
- 2011-01-05 EP EP11732089.5A patent/EP2521716B1/en active Active
- 2011-01-05 PH PH1/2012/501391A patent/PH12012501391A1/en unknown
- 2011-01-05 AU AU2011203708A patent/AU2011203708B2/en not_active Ceased
- 2011-01-05 BR BR112012016795-2A patent/BR112012016795A2/pt not_active Application Discontinuation
- 2011-01-05 MY MYPI2012003108A patent/MY161482A/en unknown
- 2011-01-05 US US13/375,607 patent/US8524754B2/en not_active Expired - Fee Related
- 2011-01-05 EA EA201270676A patent/EA020183B1/ru not_active IP Right Cessation
- 2011-01-05 CA CA2785200A patent/CA2785200C/en not_active Expired - Fee Related
- 2011-01-05 KR KR1020127020834A patent/KR20120104627A/ko not_active Ceased
- 2011-01-05 JP JP2012548092A patent/JP5696346B2/ja not_active Expired - Fee Related
- 2011-01-05 MX MX2012007925A patent/MX2012007925A/es active IP Right Grant
- 2011-01-05 WO PCT/US2011/020233 patent/WO2011085009A2/en not_active Ceased
- 2011-01-07 TW TW100100688A patent/TWI451867B/zh not_active IP Right Cessation
-
2012
- 2012-06-29 CO CO12109744A patent/CO6561780A2/es not_active Application Discontinuation
- 2012-07-02 ZA ZA2012/04938A patent/ZA201204938B/en unknown
- 2012-07-06 CL CL2012001841A patent/CL2012001841A1/es unknown
-
2013
- 2013-07-30 US US13/954,736 patent/US20130345271A1/en not_active Abandoned
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