RU2505543C2 - Твердые формы (2s,3r,4r,5s,6r)-2-(4-хлор-3-(4-этоксибензил)фенил)-6-(метилтио)тетрагидро-2н-пиран-3,4,5-триола и способы их применения - Google Patents
Твердые формы (2s,3r,4r,5s,6r)-2-(4-хлор-3-(4-этоксибензил)фенил)-6-(метилтио)тетрагидро-2н-пиран-3,4,5-триола и способы их применения Download PDFInfo
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- RU2505543C2 RU2505543C2 RU2011105797/04A RU2011105797A RU2505543C2 RU 2505543 C2 RU2505543 C2 RU 2505543C2 RU 2011105797/04 A RU2011105797/04 A RU 2011105797/04A RU 2011105797 A RU2011105797 A RU 2011105797A RU 2505543 C2 RU2505543 C2 RU 2505543C2
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- RU
- Russia
- Prior art keywords
- crystalline form
- phenyl
- pyran
- tetrahydro
- methylthio
- Prior art date
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| CN102453026A (zh) | 2010-10-27 | 2012-05-16 | 上海艾力斯医药科技有限公司 | C-芳基葡糖苷衍生物、制备方法及其应用 |
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| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| ES2728246T3 (es) | 2012-11-20 | 2019-10-23 | Lexicon Pharmaceuticals Inc | Inhibidores del cotransportador 1 de sodio-glucosa |
| WO2015069441A1 (en) | 2013-10-18 | 2015-05-14 | Medivation Technologies, Inc. | Pyrazolo-, imidazolo- and pyrrolo-pyridine or -pyrimidine derivatives as inhibitors o brutons kinase (btk) |
| EP3057970A1 (en) | 2013-10-18 | 2016-08-24 | Medivation Technologies, Inc. | Heterocyclic compounds and methods of use |
| JP6938376B2 (ja) | 2015-07-30 | 2021-09-22 | 公益財団法人微生物化学研究会 | 多剤耐性菌に有効な新規アミノグリコシド抗生物質 |
| JP6727419B2 (ja) * | 2016-05-25 | 2020-07-22 | クリスタル ファーマシューティカル（スーチョウ）カンパニー，リミテッド | ナトリウム−グルコース共輸送体阻害薬の新規な結晶形及びその製造方法並びに用途 |
| WO2018067805A1 (en) | 2016-10-06 | 2018-04-12 | Teva Pharmaceutical Industries Ltd. | Solid state forms of sotagliflozin |
| MX2019004549A (es) | 2016-10-19 | 2019-06-12 | Boehringer Ingelheim Int | Combinaciones que comprenden un inhibidor ssao/vap-1 y un inhibidor sglt2 y usos de los mismos. |
| US20210113561A1 (en) | 2018-04-17 | 2021-04-22 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| CN110818722B (zh) * | 2018-08-14 | 2022-12-02 | 苏州鹏旭医药科技有限公司 | 三种化合物及其制备方法和在合成索格列净中的用途 |
| CN112218877B (zh) | 2018-08-27 | 2025-07-25 | 瑞泽恩制药公司 | 拉曼光谱在下游纯化中的应用 |
| BR112021004839A2 (pt) * | 2018-09-26 | 2021-06-08 | Lexicon Pharmaceuticals, Inc. | formas cristalinas de n-(1-((2-(dimetilamino)etil)amino)-2-metil-1-oxopropan-2-il)-4-(4-(2-metil-5-((2s,3r,4r,5s,6r)-3,4,5-triidróxi-6-(metiltio)tetraidro-2h-piran-2-il)benzil)fenil)butanamida e métodos de sua síntese |
| WO2020089025A1 (en) | 2018-10-29 | 2020-05-07 | Boehringer Ingelheim International Gmbh | Pyridinyl sulfonamide derivatives, pharmaceutical compositions and uses thereof |
| KR102812426B1 (ko) | 2018-10-29 | 2025-05-26 | 베링거 인겔하임 인터내셔날 게엠베하 | 피리디닐 설폰아미드 유도체, 약제학적 조성물 및 이의 용도 |
| CN109824687B (zh) * | 2019-03-26 | 2022-03-22 | 上海凌凯医药科技有限公司 | 呋喃木糖衍生物的新合成方法 |
| CN113993865B (zh) * | 2019-07-05 | 2023-09-22 | 山东丹红制药有限公司 | 一种SGLTs抑制剂的晶型及其应用 |
| EP3771480A1 (en) * | 2019-08-01 | 2021-02-03 | Lexicon Pharmaceuticals, Inc. | Continuous process for preparing the crystalline form ii of sotagliflozin |
| EP3771718A1 (en) * | 2019-08-01 | 2021-02-03 | Lexicon Pharmaceuticals, Inc. | Process for preparing the crystalline form ii of sotagliflozin |
| WO2022144465A1 (en) | 2021-01-04 | 2022-07-07 | Charité-Universitätsmedizin Berlin | Sotagliflozin for improving left atrial function |
| US20220370485A1 (en) | 2021-01-14 | 2022-11-24 | Lexicon Pharmaceuticals, Inc. | Compounds and methods for treating or preventing cardiovascular diseases and conditions |
| CN113880701A (zh) * | 2021-10-10 | 2022-01-04 | 浙江司太立制药股份有限公司 | 一种抗糖尿病药物中间体及其制备方法 |
| US20250108032A1 (en) | 2023-09-28 | 2025-04-03 | Lexicon Pharmaceuticals, Inc. | Methods of treating type 1 diabetes and kidney disease |
| WO2025076165A1 (en) | 2023-10-06 | 2025-04-10 | Lexicon Pharmaceuticals, Inc. | Methods of reducing the risk of cardiovascular events in patients with left ventricular hypertrophy |
| PL446852A1 (pl) * | 2023-11-27 | 2025-06-02 | Politechnika Rzeszowska im. Ignacego Łukasiewicza | Układ doprowadzający wodę do pralki |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU944506A3 (ru) * | 1973-03-06 | 1982-07-15 | Те Апджон Компани (Фирма) | Способ получени производных @ -тиолинкозаминида |
| WO2008042688A2 (en) * | 2006-09-29 | 2008-04-10 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
Family Cites Families (7)
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| EP1248869A2 (en) * | 2000-01-07 | 2002-10-16 | Transform Pharmaceuticals, Inc. | High-throughput formation, identification, and analysis of diverse solid-forms |
| WO2006018150A1 (de) | 2004-08-11 | 2006-02-23 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-phenyl-substituierte cyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| DE602006009772D1 (de) | 2005-02-23 | 2009-11-26 | Boehringer Ingelheim Int | Glucopyranosylsubstituierte ((hetero)arylethynyl-benzyl)-benzenderivative und deren verwendung als inhibitoren des natriumabhängigen glucose-cotransporters typ 2 (sglt2) |
| CN1820858A (zh) * | 2006-03-10 | 2006-08-23 | 广西中医学院制药厂 | 多相物料喷雾方法及装置 |
| WO2008109591A1 (en) * | 2007-03-08 | 2008-09-12 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
| PT2183263E (pt) * | 2007-07-26 | 2012-01-11 | Lexicon Pharmaceuticals Inc | Processos e compostos úteis na preparação de inibidores do co-transportador 2 de glucose e sódio |
| TWI472521B (zh) | 2008-07-17 | 2015-02-11 | Lexicon Pharmaceuticals Inc | （２ｓ，３ｒ，４ｒ，５ｓ，６ｒ）－２－（４－氯－３－（４－乙氧苄基）苯基）－６－（甲硫）四氫－２ｈ－哌喃－３，４，５－三醇的固體形態與其使用方法 |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU944506A3 (ru) * | 1973-03-06 | 1982-07-15 | Те Апджон Компани (Фирма) | Способ получени производных @ -тиолинкозаминида |
| WO2008042688A2 (en) * | 2006-09-29 | 2008-04-10 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
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