KR102249543B1 - 페난트로인돌리지딘 및 페난트로퀴놀리지딘 알칼로이드 유도체, 이의 광학이성질체, 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 코로나바이러스감염증-19 치료용 조성물 - Google Patents
페난트로인돌리지딘 및 페난트로퀴놀리지딘 알칼로이드 유도체, 이의 광학이성질체, 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 코로나바이러스감염증-19 치료용 조성물 Download PDFInfo
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- KR102249543B1 KR102249543B1 KR1020200108099A KR20200108099A KR102249543B1 KR 102249543 B1 KR102249543 B1 KR 102249543B1 KR 1020200108099 A KR1020200108099 A KR 1020200108099A KR 20200108099 A KR20200108099 A KR 20200108099A KR 102249543 B1 KR102249543 B1 KR 102249543B1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
도 2는 페난트로인돌리지딘 및 페난트로퀴놀리지딘 알칼로이드 유도체 화합물의 Vero CCL-81 세포에 대한 세포 독성을 나타낸 것이다.
화합물 | Effective Concentration 50 (EC50) |
[화합물 1] |
35 nM |
[화합물 2] |
13 nM |
[화합물 3] |
17 nM |
[대조군 : Antofine] |
37 nM |
[대조군 : Cryptopleurine] |
11 nM |
[대조군 3: Remdesivir] | 22.1 μM |
Cytotoxic Concentration 50 (CC50) |
Selectivity Index (SI) |
|
[화합물 1] |
1,825 nM | 52 |
[화합물 2] |
126 nM | 10 |
[화합물 3] |
317 nM | 19 |
[대조군 : Antofine] |
872 nM | 24 |
[대조군 : Cryptopleurine] |
62 nM | 6 |
[대조군 : Remdesivir] | 171.9 μM | 7.8 |
Claims (4)
- 제1항에 있어서,
상기 화학식 1로 표시되는 화합물은 하기 화합물들로 이루어진 군으로부터 선택된 하나 이상인 것을 특징으로 하는, 약학적 조성물:
(R)-N-(2,3-디메톡시-9,11,12,13,13a,14-헥사히드로디벤조-[f,h]피롤로[1,2-b]이소퀴놀린-6-일)메탄설폰아마이드;
(R)-N-(2,3-디메톡시-11,12,13,14,14a,15-헥사히드로-9H-디벤조[f,h]피리도[1,2-b]이소퀴놀린-6-일)메탄설폰아마이드;
메틸(2,3-디메톡시-11,12,13,14,14a,15-헥사히드로-9H-디벤조[f,h]피리도[1,2-b]이소퀴놀린-6-일)카바메이트;
N-(2,3-디메톡시-11,12,13,14,14a,15-헥사히드로-9H-디벤조[f,h]피리도[1,2-b]이소퀴놀린-6-일)프로판-2-설폰아마이드; 및
N-(2,3-디메톡시-11,12,13,14,14a,15-헥사히드로-9H-디벤조[f,h]피리도[1,2-b]이소퀴놀린-6-일)아세트아마이드.
- 제2항에 있어서,
상기 화학식 1로 표시되는 화합물은 하기 화합물들로 이루어진 군으로부터 선택된 하나 이상인 것을 특징으로 하는, 약학적 조성물:
(R)-N-(2,3-디메톡시-9,11,12,13,13a,14-헥사히드로디벤조-[f,h]피롤로[1,2-b]이소퀴놀린-6-일)메탄설폰아마이드;
(R)-N-(2,3-디메톡시-11,12,13,14,14a,15-헥사히드로-9H-디벤조[f,h]피리도[1,2-b]이소퀴놀린-6-일)메탄설폰아마이드; 및
메틸(2,3-디메톡시-11,12,13,14,14a,15-헥사히드로-9H-디벤조[f,h]피리도[1,2-b]이소퀴놀린-6-일)카바메이트.
- 제1항에 있어서,
상기 코로나 바이러스는 중증급성호흡기증후군 코로나바이러스 2(SARS-CoV-2)인 것을 특징으로 하는, 약학적 조성물.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200108099A KR102249543B1 (ko) | 2020-08-26 | 2020-08-26 | 페난트로인돌리지딘 및 페난트로퀴놀리지딘 알칼로이드 유도체, 이의 광학이성질체, 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 코로나바이러스감염증-19 치료용 조성물 |
PCT/KR2021/005513 WO2022045520A1 (ko) | 2020-08-26 | 2021-04-30 | 페난트로인돌리지딘 및 페난트로퀴놀리지딘 알칼로이드 유도체, 이의 광학이성질체, 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 코로나바이러스감염증-19 치료용 조성물 |
US18/042,801 US20230233538A1 (en) | 2020-08-26 | 2021-04-30 | Composition for treating coronavirus disease-19, comprising phenanthroindolizidine and phenanthroquinolizidine alkaloid derivatives, optical isomer thereof, or pharmaceutically acceptable salts thereof as active ingredient |
EP21861822.1A EP4205742A4 (en) | 2020-08-26 | 2021-04-30 | COMPOSITION FOR THE TREATMENT OF CORONAVIRUS-19 INFECTION, COMPRISING AN ALKALOID DERIVATIVE OF PHENANTHROQUINOLIZIDINE AND PHENANTHROINDOLIZIDINE, AN OPTICAL ISOMER THEREOF OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF AS ACTIVE INGREDIENT |
Applications Claiming Priority (1)
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KR1020200108099A KR102249543B1 (ko) | 2020-08-26 | 2020-08-26 | 페난트로인돌리지딘 및 페난트로퀴놀리지딘 알칼로이드 유도체, 이의 광학이성질체, 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 코로나바이러스감염증-19 치료용 조성물 |
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KR1020200108099A Active KR102249543B1 (ko) | 2020-08-26 | 2020-08-26 | 페난트로인돌리지딘 및 페난트로퀴놀리지딘 알칼로이드 유도체, 이의 광학이성질체, 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 코로나바이러스감염증-19 치료용 조성물 |
Country Status (4)
Country | Link |
---|---|
US (1) | US20230233538A1 (ko) |
EP (1) | EP4205742A4 (ko) |
KR (1) | KR102249543B1 (ko) |
WO (1) | WO2022045520A1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113230254A (zh) * | 2021-05-27 | 2021-08-10 | 广州市朝利良生物科技有限公司 | 一种抗SARS-CoV-2的药物及应用 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5583590B2 (ja) | 2008-10-23 | 2014-09-03 | 株式会社ヤクルト本社 | フェナンスロインドリジジン化合物及びこれを有効成分とするNFκB阻害剤 |
KR101708512B1 (ko) | 2008-10-23 | 2017-02-20 | 가부시키가이샤 야쿠르트 혼샤 | 페난트로인돌리지딘 유도체 및 이것을 유효 성분으로 하는 NFκB 저해제 |
US8440649B2 (en) * | 2009-02-24 | 2013-05-14 | National Health Research Institutes | Phenanthroindolizidine analogues |
KR101806487B1 (ko) | 2016-01-25 | 2017-12-08 | 서울대학교산학협력단 | 페난트로인돌리지딘 또는 페난트로퀴놀리지딘 알칼로이드 유도체 화합물, 이의 광학이성질체, 또는 이의 약학적으로 허용가능한 염, 및 이를 유효성분으로 포함하는 항암용 조성물 |
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2020
- 2020-08-26 KR KR1020200108099A patent/KR102249543B1/ko active Active
-
2021
- 2021-04-30 WO PCT/KR2021/005513 patent/WO2022045520A1/ko unknown
- 2021-04-30 EP EP21861822.1A patent/EP4205742A4/en active Pending
- 2021-04-30 US US18/042,801 patent/US20230233538A1/en active Pending
Non-Patent Citations (3)
Title |
---|
Antiviral Research, 88, 160-168, 2010.* * |
iScience, 101303, 2020. 7. 24.* * |
J, Med. Chem. 58(19), 7749-7762, 2015.* * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113230254A (zh) * | 2021-05-27 | 2021-08-10 | 广州市朝利良生物科技有限公司 | 一种抗SARS-CoV-2的药物及应用 |
CN113230254B (zh) * | 2021-05-27 | 2022-08-23 | 广州市朝利良生物科技有限公司 | 一种抗SARS-CoV-2的药物及应用 |
Also Published As
Publication number | Publication date |
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EP4205742A1 (en) | 2023-07-05 |
WO2022045520A1 (ko) | 2022-03-03 |
EP4205742A4 (en) | 2024-07-24 |
US20230233538A1 (en) | 2023-07-27 |
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