KR20240082359A - 트라이아진 유도체를 함유하는 의약 조성물 - Google Patents
트라이아진 유도체를 함유하는 의약 조성물 Download PDFInfo
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- KR20240082359A KR20240082359A KR1020247013026A KR20247013026A KR20240082359A KR 20240082359 A KR20240082359 A KR 20240082359A KR 1020247013026 A KR1020247013026 A KR 1020247013026A KR 20247013026 A KR20247013026 A KR 20247013026A KR 20240082359 A KR20240082359 A KR 20240082359A
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Images
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Veterinary Medicine (AREA)
- Public Health (AREA)
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- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| LT4122926T (lt) * | 2021-04-14 | 2025-07-25 | Shionogi & Co., Ltd. | Triazino dariniai, turintys virusų replikaciją slopinantį poveikį, ir juos apimanti farmacinė kompozicija |
| WO2023054732A2 (ja) * | 2022-01-19 | 2023-04-06 | 塩野義製薬株式会社 | 新型コロナウイルス感染症治療用医薬 |
| WO2024193451A1 (en) * | 2023-03-17 | 2024-09-26 | Ascletis BioScience Co., Ltd | Triazine derivatives, method of making and method of using thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010092966A1 (ja) | 2009-02-13 | 2010-08-19 | 塩野義製薬株式会社 | 新規トリアジン誘導体およびそれを含有する医薬組成物 |
| WO2012020749A1 (ja) | 2010-08-10 | 2012-02-16 | 塩野義製薬株式会社 | トリアジン誘導体およびそれを含有する鎮痛作用を有する医薬組成物 |
| WO2013089212A1 (ja) | 2011-12-15 | 2013-06-20 | 塩野義製薬株式会社 | 置換トリアジン誘導体およびそれらを含有する医薬組成物 |
| WO2014200078A1 (ja) | 2013-06-14 | 2014-12-18 | 塩野義製薬株式会社 | アミノトリアジン誘導体およびそれらを含有する医薬組成物 |
| WO2021205298A1 (en) | 2020-04-05 | 2021-10-14 | Pfizer Inc. | Compounds and methods for the treatment of covid-19 |
| WO2021250648A1 (en) | 2020-09-03 | 2021-12-16 | Pfizer Inc. | Nitrile-containing antiviral compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999036410A1 (en) * | 1998-01-13 | 1999-07-22 | Scriptgen Pharmaceuticals, Inc. | Triazine antiviral compounds |
| WO2019087884A1 (ja) * | 2017-10-31 | 2019-05-09 | 富士フイルム株式会社 | 組成物、抗菌組成物、抗ウイルス用組成物、抗ノロウイルス用組成物、スプレー、ワイパー |
| EP4282420A4 (en) * | 2021-01-20 | 2024-11-27 | National University Corporation Hokkaido University | ANTIVIRAL AGENT |
| EP4313097A4 (en) * | 2021-03-29 | 2025-03-19 | Shireen Nature Company for General Trading, Ltd. | Willow extract and its use in treating coronavirus infection, inflammation, and associated medical conditions |
| LT4122926T (lt) * | 2021-04-14 | 2025-07-25 | Shionogi & Co., Ltd. | Triazino dariniai, turintys virusų replikaciją slopinantį poveikį, ir juos apimanti farmacinė kompozicija |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010092966A1 (ja) | 2009-02-13 | 2010-08-19 | 塩野義製薬株式会社 | 新規トリアジン誘導体およびそれを含有する医薬組成物 |
| WO2012020749A1 (ja) | 2010-08-10 | 2012-02-16 | 塩野義製薬株式会社 | トリアジン誘導体およびそれを含有する鎮痛作用を有する医薬組成物 |
| WO2013089212A1 (ja) | 2011-12-15 | 2013-06-20 | 塩野義製薬株式会社 | 置換トリアジン誘導体およびそれらを含有する医薬組成物 |
| WO2014200078A1 (ja) | 2013-06-14 | 2014-12-18 | 塩野義製薬株式会社 | アミノトリアジン誘導体およびそれらを含有する医薬組成物 |
| WO2021205298A1 (en) | 2020-04-05 | 2021-10-14 | Pfizer Inc. | Compounds and methods for the treatment of covid-19 |
| WO2021250648A1 (en) | 2020-09-03 | 2021-12-16 | Pfizer Inc. | Nitrile-containing antiviral compounds |
Non-Patent Citations (14)
| Title |
|---|
| "Pfizer's Novel COVID-19 Oral Antiviral Treatment Candidate Reduced Risk Of Hospitalization Or Death By 89% In Interim Analysis Of Phase 2/3 EPIC-HR Study", [online], 2021년 11월 5일, Pfizer Press Release, [2022년 9월 21일 검색], 인터넷<URL: https://www.pfizer.com/news/press-release/press-release-detail/pfizers-novel-covid-19-oral-antiviral-treatment-candidate> |
| "A comparative analysis of SARS-CoV-2 antivirals characterizes 3CLpro inhibitor PF-00835231 as a potential new treatment for COVID-19", Journal of Virology, [online], 2021년 2월 23일, [2022년 9월 21일 검색], 인터넷<URL: https://jvi.asm.org/content/early/2021/02/19/JVI.01819-20><doi: 10.1128/JVI.01819-20> |
| "COVID-19 Dashboard by the Center for Systems Science and Engineering at Johns Hopkins University", [online], Johns Hopkins University, [2022년 9월 21일 검색], 인터넷<URL:https://coronavirus.jhu.edu/map.html> |
| "Report of the WHO-China Joint Mission on Coronavirus Disease 2019 (COVID-19)", [online], 2020년 2월 28일, WHO, [2022년 9월 21일 검색], 인터넷<URL:https://www.who.int/docs/default-source/coronaviruse/who-china-joint-mission-on-covid-19-final-report.pdf> |
| 261st Am Chem Soc (ACS) Natl Meet · 2021-04-05 / 2021-04-16 · Virtual, N/A · Abst 243 |
| ACS Central Science(2021년), 7권, 3호, 467~475페이지 |
| Arzneimittel-Forschung(1984년), 11권, 6호, 663~668페이지 |
| Cancer Treatment Reviews(1984년), 11권, Supplement 1, 99~110페이지 |
| Cell Research(2020년), 30권, 678~692페이지 |
| Contributions to Oncology(1984년), 18권, 221~234페이지 |
| Science(2003년), 300권, 1763~1767페이지 |
| Science(2020년), 368권, 409~412페이지 |
| Science(2021년), 374권, 1586~1593페이지 |
| The NEW ENGLAND JOURNAL of MEDICINE(2020년), 382권, 1564~1567페이지 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN119818502A (zh) | 2025-04-15 |
| JP7236065B1 (ja) | 2023-03-09 |
| MX2024003600A (es) | 2024-04-09 |
| CA3233206A1 (en) | 2023-04-06 |
| AU2022353486A1 (en) | 2024-05-02 |
| US20250127788A1 (en) | 2025-04-24 |
| EP4410292A4 (en) | 2025-09-03 |
| JPWO2023054292A1 (https=) | 2023-04-06 |
| EP4410292A1 (en) | 2024-08-07 |
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