JP2014501282A5 - - Google Patents
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- Publication number
- JP2014501282A5 JP2014501282A5 JP2013547653A JP2013547653A JP2014501282A5 JP 2014501282 A5 JP2014501282 A5 JP 2014501282A5 JP 2013547653 A JP2013547653 A JP 2013547653A JP 2013547653 A JP2013547653 A JP 2013547653A JP 2014501282 A5 JP2014501282 A5 JP 2014501282A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropylnaphthalen
- ylthio
- bromo
- acetic acid
- triazol
- 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
- 238000000034 method Methods 0.000 claims 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- FGQFOYHRJSUHMR-UHFFFAOYSA-N lesinurad Chemical compound OC(=O)CSC1=NN=C(Br)N1C(C1=CC=CC=C11)=CC=C1C1CC1 FGQFOYHRJSUHMR-UHFFFAOYSA-N 0.000 claims 9
- -1 4-cyclopropylnaphthalen-1-yl Chemical group 0.000 claims 5
- 239000012044 organic layer Substances 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000013078 crystal Substances 0.000 claims 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 3
- 239000011707 mineral Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000012074 organic phase Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PMDOHKUQNFWVPM-UHFFFAOYSA-N [Na].OC(=O)CSc1nnc(Br)n1-c1ccc(C2CC2)c2ccccc12 Chemical compound [Na].OC(=O)CSc1nnc(Br)n1-c1ccc(C2CC2)c2ccccc12 PMDOHKUQNFWVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061428660P | 2010-12-30 | 2010-12-30 | |
| US61/428,660 | 2010-12-30 | ||
| PCT/US2011/067657 WO2012092395A2 (en) | 2010-12-30 | 2011-12-28 | Polymorphic forms of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-ylthio) acetic acid and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015088794A Division JP2015172053A (ja) | 2010-12-30 | 2015-04-23 | 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）酢酸の多形形態およびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014501282A JP2014501282A (ja) | 2014-01-20 |
| JP2014501282A5 true JP2014501282A5 (enExample) | 2014-10-02 |
| JP5781627B2 JP5781627B2 (ja) | 2015-09-24 |
Family
ID=46381300
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013547653A Expired - Fee Related JP5781627B2 (ja) | 2010-12-30 | 2011-12-28 | 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）酢酸の多形形態およびその使用 |
| JP2015088794A Pending JP2015172053A (ja) | 2010-12-30 | 2015-04-23 | 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）酢酸の多形形態およびその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015088794A Pending JP2015172053A (ja) | 2010-12-30 | 2015-04-23 | 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）酢酸の多形形態およびその使用 |
Country Status (29)
| Country | Link |
|---|---|
| US (6) | US8546436B2 (enExample) |
| EP (1) | EP2658846B1 (enExample) |
| JP (2) | JP5781627B2 (enExample) |
| KR (1) | KR101541629B1 (enExample) |
| CN (1) | CN103298796B (enExample) |
| AR (1) | AR084639A1 (enExample) |
| AU (1) | AU2011352129B2 (enExample) |
| BR (1) | BR112013016982A2 (enExample) |
| CA (1) | CA2817249C (enExample) |
| CY (1) | CY1118621T1 (enExample) |
| DK (1) | DK2658846T3 (enExample) |
| EA (1) | EA022301B1 (enExample) |
| ES (1) | ES2614914T3 (enExample) |
| HR (1) | HRP20170187T1 (enExample) |
| HU (1) | HUE031766T2 (enExample) |
| IL (1) | IL226367A (enExample) |
| LT (1) | LT2658846T (enExample) |
| MX (1) | MX2013007505A (enExample) |
| MY (1) | MY172534A (enExample) |
| NZ (1) | NZ610104A (enExample) |
| PL (1) | PL2658846T3 (enExample) |
| PT (1) | PT2658846T (enExample) |
| RS (1) | RS55667B1 (enExample) |
| SG (1) | SG190902A1 (enExample) |
| SI (1) | SI2658846T1 (enExample) |
| TW (1) | TWI452037B (enExample) |
| UA (1) | UA109172C2 (enExample) |
| WO (1) | WO2012092395A2 (enExample) |
| ZA (1) | ZA201303253B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5696346B2 (ja) | 2010-01-08 | 2015-04-08 | アルデア バイオサイエンシーズ インク． | 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 |
| CA2794798C (en) | 2010-03-30 | 2017-05-30 | Ardea Biosciences, Inc. | Treatment of gout |
| HRP20180780T1 (hr) * | 2010-06-15 | 2018-07-13 | Ardea Biosciences, Inc. | Liječenje gihta i hiperurikemije |
| HRP20170187T1 (hr) | 2010-12-30 | 2017-03-24 | Ardea Biosciences, Inc. | Polimorfni oblici 2-(5-brom-4-(4-ciklopropilnaftalen-1-il)-4h-1,2,4-triazol-3-iltio) octene kiseline i njihova upotreba |
| 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 |
| JP6026914B2 (ja) | 2013-02-12 | 2016-11-16 | ルネサスエレクトロニクス株式会社 | 半導体装置の製造方法 |
| CN104447589B (zh) * | 2013-11-20 | 2017-01-11 | 广东东阳光药业有限公司 | 一种尿酸调节剂的制备方法及其中间体 |
| 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 |
| 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 |
| CA2931430A1 (en) * | 2013-11-22 | 2015-05-28 | Crystal Pharmatech Co., Ltd. | Crystalline forms of lesinurad and its sodium salt |
| US9969701B2 (en) | 2013-12-20 | 2018-05-15 | Crystal Pharmatech Co., Ltd. | Salts and co-crystals of lesinurad |
| 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 |
| 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 |
| CN104557748A (zh) * | 2014-01-25 | 2015-04-29 | 广东东阳光药业有限公司 | 硫代-1,2,4-三唑衍生物的新的固体形态 |
| 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 |
| WO2016203436A1 (en) * | 2015-06-19 | 2016-12-22 | Dr. Reddy's Laboratories Limited | Amorphous and amorphous solid dispersion of lesinurad and their preparation |
| EP3112334A1 (en) | 2015-06-29 | 2017-01-04 | DPx Fine Chemicals Austria GmbH & CoKG | Process for manufacturing 1-cyclopropyl-naphthalenes |
| CN105017169A (zh) * | 2015-06-30 | 2015-11-04 | 安徽万邦医药科技有限公司 | 一种4-（4-环丙基萘-1-基）-5-硫代-[1,2,4]三唑烷-3-酮的制备方法及其中间体（4-环丙基萘-1-基）-氨基甲酸乙酯 |
| WO2017036884A1 (en) | 2015-08-28 | 2017-03-09 | Sandoz Ag | A lesinurad, free form / lesinurad ethyl ester co-crystal |
| CN107176930B (zh) * | 2016-03-11 | 2020-12-01 | 广东赛烽医药科技有限公司 | 2-[5-溴-4-(4-氟代环丙基萘-1-基)-4h-1，2，4-三唑-3-基硫基]乙酸化合物及其应用 |
| CN107266377A (zh) * | 2016-04-08 | 2017-10-20 | 浙江京新药业股份有限公司 | 一种urat1抑制剂的轴手性对映体的多晶型 |
| CN107298657A (zh) * | 2016-04-15 | 2017-10-27 | 浙江京新药业股份有限公司 | 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1,2,4-三唑-3-基硫基)乙酸轴手性对映体的晶型ii |
| CN107298658A (zh) * | 2016-04-15 | 2017-10-27 | 浙江京新药业股份有限公司 | 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1,2,4-三唑-3-基硫基)乙酸轴手性对映体的晶型v |
| CN107298660A (zh) * | 2016-04-15 | 2017-10-27 | 浙江京新药业股份有限公司 | 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1,2,4-三唑-3-基硫基)乙酸轴手性对映体的晶型iii |
| CN107298659A (zh) * | 2016-04-15 | 2017-10-27 | 浙江京新药业股份有限公司 | 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1,2,4-三唑-3-基硫基)乙酸轴手性对映体的晶型iv |
| 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 |
| EP3492083B1 (en) | 2016-07-29 | 2026-01-21 | Toray Industries, Inc. | Solid preparation of nalfurafine having improved light stability |
| 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 |
| WO2018085932A1 (en) * | 2016-11-10 | 2018-05-17 | Apotex Inc. | Novel crystalline forms of lesinurad |
| EP3372592A1 (en) | 2017-03-07 | 2018-09-12 | Zentiva, k.s. | Solid forms of lesinurad amine salts |
| CN106905250A (zh) * | 2017-03-07 | 2017-06-30 | 江苏艾立康药业股份有限公司 | 一种雷西纳德的新晶型 |
| EP3315494A1 (en) | 2017-04-19 | 2018-05-02 | Química Sintética, S.A. | Amorphous form of lesinurad and processes for its preparation |
| WO2018211532A1 (en) * | 2017-05-18 | 2018-11-22 | Msn Laboratories Private Limited, R&D Center | Novel solid state forms of 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4h-1,2,4-triazol-3-yl)thio)acetic acid and its process for preparation thereof |
| WO2019001325A1 (zh) * | 2017-06-28 | 2019-01-03 | 苏州科睿思制药有限公司 | 雷西纳得的晶型xv及其制备方法 |
| EP3498697A1 (en) | 2017-12-12 | 2019-06-19 | Química Sintética, S.A. | Novel salts and polymorphs of lesinurad |
| JP7282780B2 (ja) * | 2017-12-15 | 2023-05-29 | ジアンスー カニョン ファーマシューティカル カンパニー リミテッド | ４－（ナフタレン－１－イル）－４ｈ－１，２，４－トリアゾール系化合物の結晶形、塩形態及びその製造方法 |
| CN109970667A (zh) * | 2017-12-27 | 2019-07-05 | 徐州万邦金桥制药有限公司 | 一种雷西纳德的精制方法 |
| CN111153862B (zh) * | 2020-01-19 | 2021-07-06 | 北京鑫开元医药科技有限公司海南分公司 | 一种雷西纳德的精制方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004123642A (ja) | 2002-10-04 | 2004-04-22 | Shimizu Pharmaceutical Co Ltd | 電解質組成物 |
| US20050100637A1 (en) | 2003-11-12 | 2005-05-12 | Robert Murray | Carbohydrate and electrolyte replacement composition |
| EA015846B1 (ru) | 2004-08-25 | 2011-12-30 | Ардеа Байосайенсиз, Инк. | 2-[5-бром-4-(4-циклопропилнафталин-1-ил)-4н-[1,2,4]триазол-3-илсульфанил]уксусная кислота и ее метиловый эфир |
| 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 |
| WO2009070740A2 (en) | 2007-11-27 | 2009-06-04 | Ardea Biosciences Inc. | Novel compounds and compositions and methods of use |
| US8193234B2 (en) * | 2008-09-04 | 2012-06-05 | Ardea Biosciences, Inc. | Compounds, compositions and methods of using same for modulating uric acid levels |
| US8173690B2 (en) * | 2008-09-04 | 2012-05-08 | Ardea Biosciences, Inc. | Compounds, compositions and methods of using same for modulating uric acid levels |
| US8242154B2 (en) | 2008-09-04 | 2012-08-14 | Ardea Biosciences, Inc. | Compounds, compositions and methods of using same for modulating uric acid levels |
| JP5696346B2 (ja) | 2010-01-08 | 2015-04-08 | アルデア バイオサイエンシーズ インク． | 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 |
| HRP20170187T1 (hr) | 2010-12-30 | 2017-03-24 | Ardea Biosciences, Inc. | Polimorfni oblici 2-(5-brom-4-(4-ciklopropilnaftalen-1-il)-4h-1,2,4-triazol-3-iltio) octene kiseline i njihova upotreba |
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2011
- 2011-12-28 HR HRP20170187TT patent/HRP20170187T1/hr unknown
- 2011-12-28 DK DK11853861.0T patent/DK2658846T3/en active
- 2011-12-28 RS RS20170125A patent/RS55667B1/sr unknown
- 2011-12-28 EP EP11853861.0A patent/EP2658846B1/en active Active
- 2011-12-28 LT LTEP11853861.0T patent/LT2658846T/lt unknown
- 2011-12-28 WO PCT/US2011/067657 patent/WO2012092395A2/en not_active Ceased
- 2011-12-28 KR KR1020137019939A patent/KR101541629B1/ko not_active Expired - Fee Related
- 2011-12-28 UA UAA201309551A patent/UA109172C2/uk unknown
- 2011-12-28 AU AU2011352129A patent/AU2011352129B2/en not_active Ceased
- 2011-12-28 PL PL11853861T patent/PL2658846T3/pl unknown
- 2011-12-28 CN CN201180063328.2A patent/CN103298796B/zh not_active Expired - Fee Related
- 2011-12-28 MY MYPI2013001959A patent/MY172534A/en unknown
- 2011-12-28 MX MX2013007505A patent/MX2013007505A/es active IP Right Grant
- 2011-12-28 ES ES11853861.0T patent/ES2614914T3/es active Active
- 2011-12-28 US US13/339,283 patent/US8546436B2/en active Active
- 2011-12-28 AR ARP110104990 patent/AR084639A1/es unknown
- 2011-12-28 SG SG2013040894A patent/SG190902A1/en unknown
- 2011-12-28 BR BR112013016982A patent/BR112013016982A2/pt not_active IP Right Cessation
- 2011-12-28 HU HUE11853861A patent/HUE031766T2/en unknown
- 2011-12-28 NZ NZ610104A patent/NZ610104A/en not_active IP Right Cessation
- 2011-12-28 SI SI201131098A patent/SI2658846T1/sl unknown
- 2011-12-28 PT PT118538610T patent/PT2658846T/pt unknown
- 2011-12-28 JP JP2013547653A patent/JP5781627B2/ja not_active Expired - Fee Related
- 2011-12-28 EA EA201370150A patent/EA022301B1/ru not_active IP Right Cessation
- 2011-12-28 CA CA2817249A patent/CA2817249C/en not_active Expired - Fee Related
- 2011-12-30 TW TW100149991A patent/TWI452037B/zh not_active IP Right Cessation
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2013
- 2013-05-06 ZA ZA2013/03253A patent/ZA201303253B/en unknown
- 2013-05-16 IL IL226367A patent/IL226367A/en active IP Right Grant
- 2013-08-14 US US13/967,255 patent/US20130331403A1/en not_active Abandoned
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2014
- 2014-12-19 US US14/577,129 patent/US20150105410A1/en not_active Abandoned
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2015
- 2015-04-23 JP JP2015088794A patent/JP2015172053A/ja active Pending
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2016
- 2016-05-09 US US15/150,053 patent/US9956205B2/en active Active
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2017
- 2017-02-08 CY CY20171100177T patent/CY1118621T1/el unknown
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2018
- 2018-04-20 US US15/958,333 patent/US20180235939A1/en not_active Abandoned
- 2018-12-13 US US16/218,856 patent/US20190111028A1/en not_active Abandoned