JPS60243016A - 抗インフルエンザウイルス剤 - Google Patents
抗インフルエンザウイルス剤Info
- Publication number
- JPS60243016A JPS60243016A JP9762084A JP9762084A JPS60243016A JP S60243016 A JPS60243016 A JP S60243016A JP 9762084 A JP9762084 A JP 9762084A JP 9762084 A JP9762084 A JP 9762084A JP S60243016 A JPS60243016 A JP S60243016A
- Authority
- JP
- Japan
- Prior art keywords
- influenza virus
- acid
- virus agent
- compound
- formula
- 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.)
- Granted
Links
- 241000700605 Viruses Species 0.000 title claims abstract description 11
- 206010022000 influenza Diseases 0.000 title claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 16
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 239000000843 powder Substances 0.000 abstract description 7
- 238000002347 injection Methods 0.000 abstract description 6
- 239000007924 injection Substances 0.000 abstract description 6
- 239000002775 capsule Substances 0.000 abstract description 4
- 239000000284 extract Substances 0.000 abstract description 4
- 239000008187 granular material Substances 0.000 abstract description 4
- 235000020357 syrup Nutrition 0.000 abstract description 4
- 239000006188 syrup Substances 0.000 abstract description 4
- 239000000829 suppository Substances 0.000 abstract description 2
- 239000003826 tablet Substances 0.000 abstract description 2
- KRZBCHWVBQOTNZ-PSEXTPKNSA-N 3,5-di-O-caffeoyl quinic acid Chemical compound O([C@@H]1C[C@](O)(C[C@H]([C@@H]1O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 KRZBCHWVBQOTNZ-PSEXTPKNSA-N 0.000 abstract 1
- MVCIFQBXXSMTQD-UHFFFAOYSA-N 3,5-dicaffeoylquinic acid Natural products Cc1ccc(C=CC(=O)OC2CC(O)(CC(OC(=O)C=Cc3ccc(O)c(O)c3)C2O)C(=O)O)cc1C MVCIFQBXXSMTQD-UHFFFAOYSA-N 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- 235000020238 sunflower seed Nutrition 0.000 abstract 1
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 14
- 241000712461 unidentified influenza virus Species 0.000 description 14
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 13
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 13
- 229940074393 chlorogenic acid Drugs 0.000 description 13
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 13
- 235000001368 chlorogenic acid Nutrition 0.000 description 13
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 13
- 210000004072 lung Anatomy 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000009385 viral infection Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000034994 death Effects 0.000 description 4
- 231100000517 death Toxicity 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 201000009240 nasopharyngitis Diseases 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002021 butanolic extract Substances 0.000 description 3
- 239000000401 methanolic extract Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- CWVRJTMFETXNAD-GMZLATJGSA-N 5-Caffeoyl quinic acid Natural products O[C@H]1C[C@](O)(C[C@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-GMZLATJGSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000208828 Caprifoliaceae Species 0.000 description 1
- 208000003322 Coinfection Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 244000167230 Lonicera japonica Species 0.000 description 1
- 235000017617 Lonicera japonica Nutrition 0.000 description 1
- 241001570521 Lonicera periclymenum Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 206010035737 Pneumonia viral Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229950009125 cynarine Drugs 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 208000009421 viral pneumonia Diseases 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9762084A JPS60243016A (ja) | 1984-05-17 | 1984-05-17 | 抗インフルエンザウイルス剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9762084A JPS60243016A (ja) | 1984-05-17 | 1984-05-17 | 抗インフルエンザウイルス剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60243016A true JPS60243016A (ja) | 1985-12-03 |
| JPH0477730B2 JPH0477730B2 (enrdf_load_stackoverflow) | 1992-12-09 |
Family
ID=14197242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9762084A Granted JPS60243016A (ja) | 1984-05-17 | 1984-05-17 | 抗インフルエンザウイルス剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60243016A (enrdf_load_stackoverflow) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987004619A1 (fr) * | 1986-02-06 | 1987-08-13 | Code Kaffee-Handelsgesellschaft Mbh | Emploi de tanins et/ou d'acide chlorogene, ainsi que stimulants, aliments et/ou medicaments avec addition de tanin et/ou d'acide chlorogene |
| WO1988004169A1 (en) * | 1986-12-01 | 1988-06-16 | Terumo Kabushiki Kaisha | Drug for nephritis |
| AU662836B2 (en) * | 1992-09-09 | 1995-09-14 | Hoechst Aktiengesellschaft | Substituted cyclohexane derivatives for the treatment of diseases |
| EP0682024A1 (de) * | 1994-05-10 | 1995-11-15 | Hoechst Aktiengesellschaft | Cyclohexan-Derivate, Verfahren zu ihrer Herstellung und die Verwendung als Glukose-6-Phosphatase Inhibitoren |
| WO1999034812A1 (en) * | 1998-01-12 | 1999-07-15 | Kai Jian Xu | Pharmaceutical compositions and method of using same |
| WO2002020006A1 (en) * | 2000-09-06 | 2002-03-14 | Pan Pacific Pharmaceuticals, Inc. | Antiviral compounds and method of treating viral infections |
| US6632459B2 (en) | 2000-12-11 | 2003-10-14 | Nutricia N.V. | Chlorogenic acid and an analog thereof for immune system stimulation |
| KR100759466B1 (ko) | 2005-02-21 | 2007-10-04 | 한국생명공학연구원 | 3-카페오일-4-다이하이드로카페오일 퀴닌산을 함유하는 비만 예방 및 치료용 조성물 |
| CN103058871A (zh) * | 2012-12-03 | 2013-04-24 | 中国农业科学院烟草研究所 | 一种烟草绿原酸的分离纯化方法 |
| CN103102270A (zh) * | 2011-11-09 | 2013-05-15 | 安康市天源植物提取有限公司 | 一种绿原酸的制取方法 |
| CN103183616A (zh) * | 2012-12-06 | 2013-07-03 | 长沙理工大学 | 一种从红腺忍冬叶制备绿原酸的方法 |
| JP2014501718A (ja) * | 2010-11-18 | 2014-01-23 | アペプティコ・フォルシュング・ウント・エントヴィックルング・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | ペプチドおよびウイルス・ノイラミニダーゼ阻害剤を含んでなる組成物 |
| JP2017519037A (ja) * | 2014-05-09 | 2017-07-13 | スーチョアン チウチャン バイオロジカル サイエンス アンド テクノロジー カンパニー リミテッド | 原料クロロゲン酸又は原薬クロロゲン酸とその調製方法及び質量検出方法 |
| CN108084044A (zh) * | 2017-11-14 | 2018-05-29 | 湖南天济草堂制药股份有限公司 | 一种千里光衍生物及其在药物中的应用 |
-
1984
- 1984-05-17 JP JP9762084A patent/JPS60243016A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| J.FOOD.SCI=1976 * |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987004619A1 (fr) * | 1986-02-06 | 1987-08-13 | Code Kaffee-Handelsgesellschaft Mbh | Emploi de tanins et/ou d'acide chlorogene, ainsi que stimulants, aliments et/ou medicaments avec addition de tanin et/ou d'acide chlorogene |
| WO1988004169A1 (en) * | 1986-12-01 | 1988-06-16 | Terumo Kabushiki Kaisha | Drug for nephritis |
| AU662836B2 (en) * | 1992-09-09 | 1995-09-14 | Hoechst Aktiengesellschaft | Substituted cyclohexane derivatives for the treatment of diseases |
| EP0682024A1 (de) * | 1994-05-10 | 1995-11-15 | Hoechst Aktiengesellschaft | Cyclohexan-Derivate, Verfahren zu ihrer Herstellung und die Verwendung als Glukose-6-Phosphatase Inhibitoren |
| CN1043643C (zh) * | 1994-05-10 | 1999-06-16 | 赫彻斯特股份公司 | 环己烷衍生物及该化合物用于制备药物的应用 |
| WO1999034812A1 (en) * | 1998-01-12 | 1999-07-15 | Kai Jian Xu | Pharmaceutical compositions and method of using same |
| US6083921A (en) * | 1998-01-12 | 2000-07-04 | Xu; Kai Jian | Pharmaceutical compositions and method of using same |
| WO2002020006A1 (en) * | 2000-09-06 | 2002-03-14 | Pan Pacific Pharmaceuticals, Inc. | Antiviral compounds and method of treating viral infections |
| US7288271B2 (en) | 2000-12-11 | 2007-10-30 | Nutricia N.V. | Chlorogenic acid and an analog thereof for immune system stimulation |
| US6632459B2 (en) | 2000-12-11 | 2003-10-14 | Nutricia N.V. | Chlorogenic acid and an analog thereof for immune system stimulation |
| KR100759466B1 (ko) | 2005-02-21 | 2007-10-04 | 한국생명공학연구원 | 3-카페오일-4-다이하이드로카페오일 퀴닌산을 함유하는 비만 예방 및 치료용 조성물 |
| JP2014501718A (ja) * | 2010-11-18 | 2014-01-23 | アペプティコ・フォルシュング・ウント・エントヴィックルング・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | ペプチドおよびウイルス・ノイラミニダーゼ阻害剤を含んでなる組成物 |
| CN103102270A (zh) * | 2011-11-09 | 2013-05-15 | 安康市天源植物提取有限公司 | 一种绿原酸的制取方法 |
| CN103058871A (zh) * | 2012-12-03 | 2013-04-24 | 中国农业科学院烟草研究所 | 一种烟草绿原酸的分离纯化方法 |
| CN103058871B (zh) * | 2012-12-03 | 2015-07-08 | 中国农业科学院烟草研究所 | 一种烟草绿原酸的分离纯化方法 |
| CN103183616A (zh) * | 2012-12-06 | 2013-07-03 | 长沙理工大学 | 一种从红腺忍冬叶制备绿原酸的方法 |
| CN103183616B (zh) * | 2012-12-06 | 2014-12-03 | 长沙理工大学 | 一种从红腺忍冬叶制备绿原酸的方法 |
| JP2017519037A (ja) * | 2014-05-09 | 2017-07-13 | スーチョアン チウチャン バイオロジカル サイエンス アンド テクノロジー カンパニー リミテッド | 原料クロロゲン酸又は原薬クロロゲン酸とその調製方法及び質量検出方法 |
| CN108084044A (zh) * | 2017-11-14 | 2018-05-29 | 湖南天济草堂制药股份有限公司 | 一种千里光衍生物及其在药物中的应用 |
| CN108084044B (zh) * | 2017-11-14 | 2020-07-03 | 湖南天济草堂制药股份有限公司 | 一种千里光衍生物及其在药物中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0477730B2 (enrdf_load_stackoverflow) | 1992-12-09 |
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