JP5286087B2 - 新規グリチルレチン酸−３０−アミド誘導体及びその用途 - Google Patents
新規グリチルレチン酸−３０−アミド誘導体及びその用途 Download PDFInfo
- Publication number
- JP5286087B2 JP5286087B2 JP2008534857A JP2008534857A JP5286087B2 JP 5286087 B2 JP5286087 B2 JP 5286087B2 JP 2008534857 A JP2008534857 A JP 2008534857A JP 2008534857 A JP2008534857 A JP 2008534857A JP 5286087 B2 JP5286087 B2 JP 5286087B2
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- Japan
- Prior art keywords
- compound
- methyl
- general formula
- isoxazol
- deoxy
- 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.)
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- MPDGHEJMBKOTSU-WFJWTYAKSA-N (2s,4as,6as,6br,10s,12as)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid Chemical compound C12C(=O)C=C3C4C[C@@](C)(C(O)=O)CC[C@]4(C)CC[C@@]3(C)[C@]1(C)CCC1[C@]2(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-WFJWTYAKSA-N 0.000 title abstract 2
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- 150000001875 compounds Chemical class 0.000 claims description 84
- -1 bromo, hydroxyl group Chemical group 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
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- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229940127557 pharmaceutical product Drugs 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Neurology (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200510015371.8 | 2005-10-14 | ||
| CNB2005100153718A CN100488979C (zh) | 2005-10-14 | 2005-10-14 | 甘草次酸-30-酰胺类衍生物及其用途 |
| PCT/CN2006/002711 WO2007041969A1 (fr) | 2005-10-14 | 2006-10-16 | Dérivés d'acide glycyrrhétinique-30-amide et applications |
Publications (3)
| Publication Number | Publication Date |
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| JP2009511511A JP2009511511A (ja) | 2009-03-19 |
| JP2009511511A5 JP2009511511A5 (enExample) | 2009-10-08 |
| JP5286087B2 true JP5286087B2 (ja) | 2013-09-11 |
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| JP2008534857A Expired - Fee Related JP5286087B2 (ja) | 2005-10-14 | 2006-10-16 | 新規グリチルレチン酸−３０−アミド誘導体及びその用途 |
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| Country | Link |
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| US (1) | US7790759B2 (enExample) |
| EP (1) | EP1935892B1 (enExample) |
| JP (1) | JP5286087B2 (enExample) |
| CN (1) | CN100488979C (enExample) |
| AT (1) | ATE477019T1 (enExample) |
| AU (1) | AU2006301708B2 (enExample) |
| DE (1) | DE602006016146D1 (enExample) |
| ES (1) | ES2350053T3 (enExample) |
| WO (1) | WO2007041969A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101229172B (zh) * | 2007-12-28 | 2010-10-27 | 天津药物研究院 | 甘草次酸30-酰胺类衍生物的固体分散物、其制备方法和用途 |
| WO2009090063A1 (en) * | 2008-01-16 | 2009-07-23 | Jado Technologies Gmbh | Steroid sapogenin, androstane and triterpenoid sapogenin derivatives for the treatment and prevention of infectious diseases |
| KR101220182B1 (ko) * | 2009-02-25 | 2013-01-11 | 에스케이바이오팜 주식회사 | 치환된 아졸 유도체 화합물, 이를 포함하는 약제학적 조성물 및 이를 이용한 파킨슨씨 병 치료방법 |
| CN101899081B (zh) * | 2009-05-31 | 2012-09-05 | 江苏正大天晴药业股份有限公司 | 甘草次酸酯类衍生物合成方法以及脱氧甘草次酸酯化合物 |
| CN102653550A (zh) * | 2011-03-01 | 2012-09-05 | 广西壮族自治区药用植物园 | 甘草次酸的制备及用途 |
| CN102250187B (zh) * | 2011-04-25 | 2013-03-27 | 北京中海康医药科技发展有限公司 | 一种甘草次酸衍生物及其制备方法 |
| CN102241726B (zh) * | 2011-05-27 | 2013-06-12 | 苏州大学 | 甘草次酸衍生物及其作为抗肿瘤药物的应用 |
| CN102813661B (zh) * | 2011-06-09 | 2014-04-09 | 天津药物研究院 | 一种甘草次酸衍生物的用途 |
| TWI424839B (zh) | 2011-10-27 | 2014-02-01 | Univ Kaohsiung Medical | 18β－甘草次酸衍生物及其用途 |
| CN103102382A (zh) * | 2011-11-14 | 2013-05-15 | 天津药物研究院 | 甘草次酸-30-酰胺类衍生物的晶型b及其制备方法 |
| CN103102383A (zh) * | 2011-11-14 | 2013-05-15 | 天津药物研究院 | 甘草次酸-30-酰胺类衍生物的晶型a及其制备方法 |
| CN102579462B (zh) * | 2012-01-18 | 2013-05-22 | 苏州大学 | 甘草次酸衍生物制备抗炎药物中的应用 |
| CN102838651B (zh) * | 2012-09-26 | 2014-05-28 | 天津药物研究院 | 一类齐墩果酸的衍生物及其制备方法和用途 |
| CA2931492C (en) | 2013-11-25 | 2020-03-24 | Ini Corporation | Glycyrrhetinic acid derivative and use thereof |
| CN107619425A (zh) * | 2017-09-21 | 2018-01-23 | 南京师范大学 | 一种尾接有机导向分子的芳基钌配合物及其合成方法和应用 |
| US9896476B1 (en) | 2017-09-21 | 2018-02-20 | King Saud University | Glycyrrhetic acid derivatives |
| CN110776549B (zh) * | 2019-11-25 | 2021-06-11 | 烟台大学 | 含氮杂环甘草次酸衍生物及其制备方法和抗甲型流感病毒应用 |
| CN111018938B (zh) * | 2019-12-10 | 2021-05-25 | 中国人民解放军第二军医大学 | 一种五环三萜类甘草次酸衍生物及制备方法与应用 |
| CN118561945A (zh) * | 2024-05-22 | 2024-08-30 | 厦门稀土材料研究所 | 18β-甘草次酸酯类衍生物及其制备方法和用途 |
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|---|---|---|---|---|
| GB1447162A (en) | 1974-03-12 | 1976-08-25 | Landerlan Sa Lab | Triterpene derivatives |
| GB1516271A (en) | 1976-03-15 | 1978-06-28 | Biorex Laboratories Ltd | Glycyrrhetinic acid derivatives |
| GB2140809A (en) | 1983-06-01 | 1984-12-05 | Biorex Laboratories Ltd | New derivatives of glycyrrhetinic acid |
| GB0105772D0 (en) | 2001-03-08 | 2001-04-25 | Sterix Ltd | Use |
| DE10307388A1 (de) | 2003-02-21 | 2004-09-02 | Cognis Deutschland Gmbh & Co. Kg | Glyzyrrhetinsäureester |
| EP1660184A4 (en) * | 2003-06-30 | 2008-05-14 | Merck & Co Inc | 17-ACETAMIDO-4-AZASTEROIDE DERIVATIVES AS ANDROGEN RECEPTOR MODULATORS |
| CN1257182C (zh) | 2004-04-06 | 2006-05-24 | 南开大学 | 甘草次酸的制备方法 |
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2005
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2006
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- 2006-10-16 US US12/090,169 patent/US7790759B2/en not_active Expired - Fee Related
- 2006-10-16 WO PCT/CN2006/002711 patent/WO2007041969A1/zh not_active Ceased
- 2006-10-16 JP JP2008534857A patent/JP5286087B2/ja not_active Expired - Fee Related
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- 2006-10-16 AU AU2006301708A patent/AU2006301708B2/en not_active Ceased
- 2006-10-16 EP EP06791264A patent/EP1935892B1/en not_active Not-in-force
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| Publication number | Publication date |
|---|---|
| AU2006301708B2 (en) | 2011-06-23 |
| AU2006301708A1 (en) | 2007-04-19 |
| CN1948332A (zh) | 2007-04-18 |
| EP1935892A4 (en) | 2009-04-01 |
| DE602006016146D1 (de) | 2010-09-23 |
| WO2007041969A1 (fr) | 2007-04-19 |
| US20080214636A1 (en) | 2008-09-04 |
| EP1935892A1 (en) | 2008-06-25 |
| ATE477019T1 (de) | 2010-08-15 |
| ES2350053T3 (es) | 2011-01-17 |
| JP2009511511A (ja) | 2009-03-19 |
| CN100488979C (zh) | 2009-05-20 |
| US7790759B2 (en) | 2010-09-07 |
| EP1935892B1 (en) | 2010-08-11 |
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