KR20250013306A - 페오놀 및 아포시닌을 포함하는 액체 제형 - Google Patents
페오놀 및 아포시닌을 포함하는 액체 제형 Download PDFInfo
- Publication number
- KR20250013306A KR20250013306A KR1020257001687A KR20257001687A KR20250013306A KR 20250013306 A KR20250013306 A KR 20250013306A KR 1020257001687 A KR1020257001687 A KR 1020257001687A KR 20257001687 A KR20257001687 A KR 20257001687A KR 20250013306 A KR20250013306 A KR 20250013306A
- Authority
- KR
- South Korea
- Prior art keywords
- formulation
- isomer
- apocynin
- phenol
- weight ratio
- 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.)
- Pending
Links
- 239000012669 liquid formulation Substances 0.000 title claims abstract description 25
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 title claims description 164
- 229930188866 apocynin Natural products 0.000 title claims description 76
- UILPJVPSNHJFIK-UHFFFAOYSA-N Paeonol Chemical compound COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 title claims description 13
- YLTGFGDODHXMFB-UHFFFAOYSA-N isoacetovanillon Natural products COC1=CC=C(C(C)=O)C=C1O YLTGFGDODHXMFB-UHFFFAOYSA-N 0.000 title description 6
- MLIBGOFSXXWRIY-UHFFFAOYSA-N paeonol Natural products COC1=CC=C(O)C(C(C)=O)=C1 MLIBGOFSXXWRIY-UHFFFAOYSA-N 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 78
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 61
- 238000009472 formulation Methods 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 46
- 239000007788 liquid Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
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- 208000027866 inflammatory disease Diseases 0.000 claims description 4
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- 238000002844 melting Methods 0.000 description 7
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- 239000004480 active ingredient Substances 0.000 description 6
- 229930003811 natural phenol Natural products 0.000 description 6
- 229930182470 glycoside Natural products 0.000 description 5
- 150000002338 glycosides Chemical class 0.000 description 5
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- XSIQHIDJSCQWBB-QHJBZRDQSA-N [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 3-methoxy-4-[(E)-3-phenylprop-2-enoyl]oxybenzoate dihydrate Chemical compound O.O.COc1cc(ccc1OC(=O)\C=C\c1ccccc1)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O XSIQHIDJSCQWBB-QHJBZRDQSA-N 0.000 description 4
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 3
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- VZEOJJIAYZCDPI-UHFFFAOYSA-N 1-(2-hydroxy-3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(C(C)=O)=C1O VZEOJJIAYZCDPI-UHFFFAOYSA-N 0.000 description 2
- XPHIPEXPAGCEBM-UHFFFAOYSA-N 2-methoxy-4-hydroxyacetophenone Natural products COC1=CC(O)=CC=C1C(C)=O XPHIPEXPAGCEBM-UHFFFAOYSA-N 0.000 description 2
- 241000722949 Apocynum Species 0.000 description 2
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- 235000003889 Paeonia suffruticosa Nutrition 0.000 description 2
- 244000290333 Vanilla fragrans Species 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
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- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- NLSMPWTZYGSAEU-CYUNEVMDSA-N (2s,3r,4s,5s,6r)-2-[7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-5-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride Chemical compound [Cl-].C1=C(O)C(OC)=CC(C=2C(=CC=3C(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=CC(O)=CC=3[O+]=2)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1 NLSMPWTZYGSAEU-CYUNEVMDSA-N 0.000 description 1
- QUOZWMJFTQUXON-UXXRCYHCSA-N 1-[3-methoxy-4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QUOZWMJFTQUXON-UXXRCYHCSA-N 0.000 description 1
- QUOZWMJFTQUXON-UHFFFAOYSA-N Androsin Natural products COC1=CC(C(C)=O)=CC=C1OC1C(O)C(O)C(O)C(CO)O1 QUOZWMJFTQUXON-UHFFFAOYSA-N 0.000 description 1
- IRLNKOAURQPXIQ-WWWUCTDISA-N Apiopaeonoside Natural products O=C(C)c1c(O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO[C@H]3[C@H](O)[C@@](O)(CO)CO3)O2)cc(OC)cc1 IRLNKOAURQPXIQ-WWWUCTDISA-N 0.000 description 1
- 241000879217 Apocynum androsaemifolium Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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- IDZZECHGWAZTIB-NYBIBFQCSA-N Paeonolide Chemical compound COC1=CC=C(C(C)=O)C(O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]3[C@@H]([C@@H](O)[C@@H](O)CO3)O)O2)O)=C1 IDZZECHGWAZTIB-NYBIBFQCSA-N 0.000 description 1
- IDZZECHGWAZTIB-WPQJODJHSA-N Paeonolide Natural products O=C(C)c1c(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]3[C@@H](O)[C@H](O)[C@@H](O)CO3)O2)cc(OC)cc1 IDZZECHGWAZTIB-WPQJODJHSA-N 0.000 description 1
- AVIUTYMRHHBXPB-UXXRCYHCSA-N Paeonoside Natural products COC1=CC=C(C(C)=O)C(O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=C1 AVIUTYMRHHBXPB-UXXRCYHCSA-N 0.000 description 1
- 240000001745 Rheum palmatum Species 0.000 description 1
- 235000008090 Rheum palmatum Nutrition 0.000 description 1
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- 235000017089 Scutellaria baicalensis Nutrition 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- XZGPUOQGERGURE-LUVHZPKESA-N [(2r,3s,4s,5r,6s)-6-[[(1as,1bs,2s,5ar,6s,6as)-6-hydroxy-1a-(hydroxymethyl)-2,5a,6,6a-tetrahydro-1bh-oxireno[5,6]cyclopenta[1,3-c]pyran-2-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (e)-3-phenylprop-2-enoate Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@H]1OC=C[C@H]2[C@H](O)[C@@H]3O[C@@]3([C@@H]12)CO)OC(=O)\C=C\C1=CC=CC=C1 XZGPUOQGERGURE-LUVHZPKESA-N 0.000 description 1
- IDZZECHGWAZTIB-UHFFFAOYSA-N affinoside Natural products COC1=CC=C(C(C)=O)C(OC2C(C(O)C(O)C(COC3C(C(O)C(O)CO3)O)O2)O)=C1 IDZZECHGWAZTIB-UHFFFAOYSA-N 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
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- 229940079593 drug Drugs 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- -1 for example Substances 0.000 description 1
- SCIGYBYAZUFDLA-YRWPAIAPSA-N globularin Natural products OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](O)[C@@H]4O[C@]4(COC(=O)C=Cc5ccccc5)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O SCIGYBYAZUFDLA-YRWPAIAPSA-N 0.000 description 1
- AVIUTYMRHHBXPB-UHFFFAOYSA-N glucopaeonol Natural products COC1=CC=C(C(C)=O)C(OC2C(C(O)C(O)C(CO)O2)O)=C1 AVIUTYMRHHBXPB-UHFFFAOYSA-N 0.000 description 1
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- 150000008145 iridoid glycosides Chemical class 0.000 description 1
- XFFQVRFGLSBFON-DEFKTLOSSA-N kaempferol 3,7-di-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=C(C=3C=CC(O)=CC=3)OC2=C1 XFFQVRFGLSBFON-DEFKTLOSSA-N 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229930194807 paeonin Natural products 0.000 description 1
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- KEUKDVIGAVVGLF-RUYHYXBRSA-N picroside I Natural products OC[C@]12O[C@H]1[C@@H]3O[C@@H](O[C@@H]4O[C@H](COC(=O)C=Cc5ccccc5)[C@@H](O)[C@H](O)[C@H]4O)C=C[C@@H]3[C@H]2O KEUKDVIGAVVGLF-RUYHYXBRSA-N 0.000 description 1
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Classifications
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- A61K36/18—Magnoliophyta (angiosperms)
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- A61K36/24—Apocynaceae (Dogbane family), e.g. plumeria or periwinkle
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- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
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- A61K36/18—Magnoliophyta (angiosperms)
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- A61K36/65—Paeoniaceae (Peony family), e.g. Chinese peony
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- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Mycology (AREA)
- Alternative & Traditional Medicine (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1719464.8 | 2017-11-23 | ||
| GB1719464.8A GB2568698A (en) | 2017-11-23 | 2017-11-23 | Formulation |
| PCT/EP2018/082178 WO2019101842A1 (en) | 2017-11-23 | 2018-11-22 | Liquid formulation comprising paeonol and apocynin |
| KR1020207018001A KR102758107B1 (ko) | 2017-11-23 | 2018-11-22 | 페오놀 및 아포시닌을 포함하는 액체 제형 |
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| KR1020207018001A Active KR102758107B1 (ko) | 2017-11-23 | 2018-11-22 | 페오놀 및 아포시닌을 포함하는 액체 제형 |
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| GB2568698A (en) * | 2017-11-23 | 2019-05-29 | Akl Res & Development Ltd | Formulation |
| GB202218160D0 (en) * | 2022-12-02 | 2023-01-18 | Akl Res & Development Ltd | Formulation |
| CN119033608B (zh) * | 2024-11-01 | 2025-03-25 | 深圳杉海创新技术有限公司 | 一种具有抑菌作用的低共熔溶剂、微脂囊及其制备方法与应用 |
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| KR920700613A (ko) * | 1989-05-16 | 1992-08-10 | 지구르트 퓌터 | 약제제 |
| CN100544708C (zh) * | 2004-08-18 | 2009-09-30 | 上海佰加壹医药有限公司 | 一种丹皮酚软胶囊及其制备方法 |
| GB2424833B (en) * | 2005-04-08 | 2008-12-10 | Nicholas John Larkins | Anti-inflammatory formulation comprising apocyanin and paeonol |
| GB2463080A (en) * | 2008-09-02 | 2010-03-03 | Nicholas John Larkins | Pharmaceutical preparation |
| GB201115757D0 (en) * | 2011-09-12 | 2011-10-26 | Akl Inflammatory Ltd | Formulation for the treatment of benign prostate hyperplasia |
| GB201416909D0 (en) * | 2014-09-25 | 2014-11-12 | Prosonix Ltd | Method of forming concentrated solution |
| GB2547241A (en) * | 2016-02-11 | 2017-08-16 | Akl Res & Dev Ltd | Anti-inflammatory formulation |
| GB2568698A (en) * | 2017-11-23 | 2019-05-29 | Akl Res & Development Ltd | Formulation |
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2017
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2022
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