CN102321077A - 经色原烷取代的苯并咪唑类和它们作为酸泵抑制剂的用途 - Google Patents
经色原烷取代的苯并咪唑类和它们作为酸泵抑制剂的用途 Download PDFInfo
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- CN102321077A CN102321077A CN2011101399640A CN201110139964A CN102321077A CN 102321077 A CN102321077 A CN 102321077A CN 2011101399640 A CN2011101399640 A CN 2011101399640A CN 201110139964 A CN201110139964 A CN 201110139964A CN 102321077 A CN102321077 A CN 102321077A
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- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 11
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110225929A (zh) * | 2016-12-20 | 2019-09-10 | 埃克森美孚化学专利公司 | 聚合方法 |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JOP20190198A1 (ar) * | 2018-08-28 | 2020-02-28 | Hk Inno N Corp | تركيبة صيدلانية تشتمل على عامل مضاد للصفيحات ومثبط إفراز حمض معدي |
| JOP20190201A1 (ar) * | 2018-08-29 | 2020-02-29 | Hk Inno N Corp | تركيبة لاستئصال الملوية البوابية |
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| CN118355013A (zh) * | 2021-12-08 | 2024-07-16 | 制药基因科学株式会社 | 苯并咪唑衍生物化合物及其用途 |
| KR102708701B1 (ko) * | 2021-12-27 | 2024-09-24 | 에이치케이이노엔 주식회사 | 벤즈이미다졸 유도체의 제조방법 |
| CN114805317A (zh) * | 2022-05-20 | 2022-07-29 | 江苏威奇达药业有限公司 | 一种特戈拉赞的制备方法 |
| US12060148B2 (en) | 2022-08-16 | 2024-08-13 | Honeywell International Inc. | Ground resonance detection and warning system and method |
| KR20240028127A (ko) | 2022-08-24 | 2024-03-05 | 위더스제약주식회사 | 테고프라잔 고체분산체 조성물 |
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| WO2024087155A1 (zh) * | 2022-10-28 | 2024-05-02 | 深圳市华先医药科技有限公司 | 一种合成4-羟基-n,n,2-三甲基苯并咪唑-6-甲酰胺的方法 |
| WO2024087156A1 (zh) * | 2022-10-28 | 2024-05-02 | 深圳市华先医药科技有限公司 | 4-羟基-n,n,2-三甲基苯并咪唑-6-甲酰胺的可放大生产方法 |
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| CN118724858B (zh) * | 2023-03-31 | 2025-09-19 | 上海医药工业研究院有限公司 | 一种(r)-苯并吡喃-4-醇类化合物的制备方法 |
| KR20250164238A (ko) * | 2023-04-07 | 2025-11-24 | 제이더블유중외제약 주식회사 | 벤즈이미다졸 유도체의 염 |
| CN116621821A (zh) * | 2023-05-29 | 2023-08-22 | 宙晟智维生命科学(上海)有限公司 | 一种无定形的苯并咪唑基化合物及固体分散体 |
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| CN116789654A (zh) * | 2023-07-10 | 2023-09-22 | 杭州小蓓医药科技有限公司 | 一种特戈拉赞的制备方法 |
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| KR20250066641A (ko) | 2023-11-07 | 2025-05-14 | 엠에프씨 주식회사 | 테고프라잔 말리에이트염 1수화물 결정형 및 이의 제조방법 |
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| KR20250118583A (ko) | 2024-01-30 | 2025-08-06 | 진양제약주식회사 | 테고프라잔을 포함하는 제약 조성물 |
| KR102825970B1 (ko) | 2024-02-16 | 2025-06-26 | 스마트바이오팜 주식회사 | 테고프라잔 중간체를 제조하는 방법 및 이에 사용되는 신규 중간체 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| SE8604566D0 (sv) * | 1986-10-27 | 1986-10-27 | Haessle Ab | Novel compunds |
| US5444775A (en) | 1993-11-09 | 1995-08-22 | Tobish; John J. | Telephone key selection aid |
| SE9602286D0 (sv) * | 1996-06-10 | 1996-06-10 | Astra Ab | New compounds |
| GB9914022D0 (en) | 1999-06-17 | 1999-08-18 | Zeneca Ltd | Chemical compounds |
| AR043063A1 (es) * | 2002-12-13 | 2005-07-13 | Altana Pharma Ag | Bencimidazoles 6-sustituidos y su uso como inhibidores de secreciones gastricas |
| AR049168A1 (es) * | 2004-05-18 | 2006-07-05 | Altana Pharma Ag | Derivados de benzimidazol |
| EP1893197B1 (en) * | 2005-06-14 | 2009-09-09 | RaQualia Pharma Inc | Chromane substituted benzimidazole derivatives as acid pump antagonists |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110225929A (zh) * | 2016-12-20 | 2019-09-10 | 埃克森美孚化学专利公司 | 聚合方法 |
| CN110225929B (zh) * | 2016-12-20 | 2021-09-24 | 埃克森美孚化学专利公司 | 聚合方法 |
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| BR122020004679B1 (pt) | 2021-09-21 |
| GT200600514A (es) | 2007-07-17 |
| KR20080080195A (ko) | 2008-09-02 |
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