CA2635318A1 - Derives de triterpenequinone et de triterpenephenol et leur application pour le traitement de tumeurs et de maladies parasitaires - Google Patents
Derives de triterpenequinone et de triterpenephenol et leur application pour le traitement de tumeurs et de maladies parasitaires Download PDFInfo
- Publication number
- CA2635318A1 CA2635318A1 CA002635318A CA2635318A CA2635318A1 CA 2635318 A1 CA2635318 A1 CA 2635318A1 CA 002635318 A CA002635318 A CA 002635318A CA 2635318 A CA2635318 A CA 2635318A CA 2635318 A1 CA2635318 A1 CA 2635318A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- alkyl
- group
- independently hydrogen
- hydroxyl
- 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.)
- Abandoned
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- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 15
- 208000030852 Parasitic disease Diseases 0.000 title claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 229940002612 prodrug Drugs 0.000 claims abstract description 25
- 239000000651 prodrug Substances 0.000 claims abstract description 25
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 795
- 239000001257 hydrogen Substances 0.000 claims description 793
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 626
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 370
- 150000001875 compounds Chemical class 0.000 claims description 214
- 229910052736 halogen Inorganic materials 0.000 claims description 186
- 150000002367 halogens Chemical class 0.000 claims description 186
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 182
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 143
- 229910052799 carbon Inorganic materials 0.000 claims description 143
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 143
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 106
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 105
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- WDLKQKYLIFAMMR-UHFFFAOYSA-N methyl 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate Chemical compound CC1=C(O)C(O)=CC2=C(CCC3(C)C4(C)CCC5(C)CCC(CC53)(C)C(=O)OC)C4=CC=C21 WDLKQKYLIFAMMR-UHFFFAOYSA-N 0.000 claims description 4
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- GGXFXLUYODZCPP-UHFFFAOYSA-N CC1CC2C(C)(CC(O)C3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5C4(C)C(Br)CC23C)C(O)C1=O Chemical compound CC1CC2C(C)(CC(O)C3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5C4(C)C(Br)CC23C)C(O)C1=O GGXFXLUYODZCPP-UHFFFAOYSA-N 0.000 claims 1
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- IGVNLMJNJQFUKS-UHFFFAOYSA-N methyl 11-hydroxy-10-(2-methoxyethoxymethoxy)-2,4a,6a,6a,9,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate Chemical compound C1C(C)(C(=O)OC)CCC2(C)CCC3(C)C4=CC(=O)C5=C(C)C(OCOCCOC)=C(O)C=C5C4(C)CCC3(C)C21 IGVNLMJNJQFUKS-UHFFFAOYSA-N 0.000 claims 1
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
- C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Emergency Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ESP200503263 | 2005-12-30 | ||
| ES200503263A ES2277568B1 (es) | 2005-12-30 | 2005-12-30 | Derivados de triterpenoquinona y triterpenofenoles y su aplicacion para el tratamiento de tumores y enfermedades parasitarias. |
| PCT/EP2006/070276 WO2007077203A2 (fr) | 2005-12-30 | 2006-12-29 | Derives de triterpenequinone et de triterpenephenol et leur application pour le traitement de tumeurs et de maladies parasitaires |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2635318A1 true CA2635318A1 (fr) | 2007-07-12 |
Family
ID=37946257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002635318A Abandoned CA2635318A1 (fr) | 2005-12-30 | 2006-12-29 | Derives de triterpenequinone et de triterpenephenol et leur application pour le traitement de tumeurs et de maladies parasitaires |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1976533A2 (fr) |
| JP (1) | JP2009522239A (fr) |
| KR (1) | KR20080083044A (fr) |
| CN (1) | CN101351211A (fr) |
| AU (1) | AU2006334359A1 (fr) |
| BR (1) | BRPI0620845A2 (fr) |
| CA (1) | CA2635318A1 (fr) |
| ES (1) | ES2277568B1 (fr) |
| MX (1) | MX2008008556A (fr) |
| RU (1) | RU2008131311A (fr) |
| WO (1) | WO2007077203A2 (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1889920B1 (fr) | 2005-04-13 | 2010-01-06 | Consejo Superior De Investigaciones Cientificas | Methode in vitro d'identification de composes pour la therapie du cancer |
| WO2009026163A1 (fr) * | 2007-08-17 | 2009-02-26 | Burnham Institute For Medical Research | Compositions et procédés pour inhiber la croissance et la métastase d'un mélanome |
| CN101434635B (zh) | 2007-11-16 | 2012-05-16 | 上海华拓医药科技发展股份有限公司 | 一类具抗肿瘤活性的水溶性酚性三萜化合物及其制备方法 |
| US20100068302A1 (en) * | 2008-09-17 | 2010-03-18 | Traslational Cancer Drugs Pharma, S.L. | Methods and compositions for the treatment of cancer |
| WO2010049173A1 (fr) * | 2008-10-31 | 2010-05-06 | Cenix Bioscience Gmbh | Utilisation d’inhibiteurs de kinases hôtes pour traiter les maladies infectieuses |
| US8691977B2 (en) * | 2010-08-23 | 2014-04-08 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| AU2016342375B2 (en) | 2015-10-23 | 2022-03-17 | Erx Pharmaceuticals Inc | Analogs of celastrol |
| US10808005B2 (en) | 2016-07-04 | 2020-10-20 | Ixmedicine (Xiamen) Biological Technology Company Limited | Ligand for orphan nuclear receptor Nur77 and uses thereof |
| CN109790164B (zh) | 2016-07-25 | 2022-01-25 | 内尔维亚诺医疗科学公司 | 作为胆碱激酶抑制剂的嘌呤和3-去氮杂嘌呤类似物 |
| JP7178401B2 (ja) | 2017-07-11 | 2022-11-25 | ネルビアーノ・メデイカル・サイエンシーズ・エツセ・エルレ・エルレ | コリンキナーゼ阻害剤としてのピラゾロキナゾリン誘導体 |
| WO2020257658A1 (fr) | 2019-06-20 | 2020-12-24 | University Of Iowa Research Foundation | Nanoparticules comprenant des quinone-méthides et compositions à utiliser |
| CN113827599A (zh) * | 2021-09-23 | 2021-12-24 | 天津国际生物医药联合研究院 | 去甲泽拉木醛在抗登革病毒感染中的潜在应用 |
| CN116023426A (zh) * | 2022-12-30 | 2023-04-28 | 上海海洋大学 | 去甲泽拉木醛衍生物及其在制备抗癌药物中的应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328309A (en) * | 1980-07-02 | 1982-05-04 | The United States Of America As Represented By The Secretary Of The Department Of Health & Human Services | Method for producing tripdiolide, triptolide and celastrol |
| DE4117854A1 (de) * | 1991-05-31 | 1992-12-03 | Wiemann Wolfram | Verwendung mindestens eines celastroloids als bestandteil fuer ein arzneimittel zur behandlung von erkrankungen des rheumatoiden formenkreises, insbesondere rheumatismus |
| US5650167A (en) * | 1995-11-16 | 1997-07-22 | Dawa Incorporated | Method and composition for treating hepatitis B |
| ES2117950B1 (es) | 1996-08-02 | 1999-09-16 | Univ Granada | Nuevos compuestos que bloquean la biosintesis de fosforilcolina y su uso como segundo mensajero en proliferacion celular. |
| CN1155610C (zh) * | 2002-11-05 | 2004-06-30 | 浙江大学 | 具有抗氧化和抗肿瘤活性扁蒴藤素系列衍生物及合成方法 |
| US20040220267A1 (en) * | 2003-02-07 | 2004-11-04 | Devlin J. P. | Derivatives of pentacyclic nortriterpene quinone methides as compounds useful in the treatment of inflammatory, neurodegenerative, and neoplastic diseases |
-
2005
- 2005-12-30 ES ES200503263A patent/ES2277568B1/es not_active Expired - Fee Related
-
2006
- 2006-12-29 KR KR1020087018837A patent/KR20080083044A/ko not_active Application Discontinuation
- 2006-12-29 MX MX2008008556A patent/MX2008008556A/es unknown
- 2006-12-29 WO PCT/EP2006/070276 patent/WO2007077203A2/fr active Application Filing
- 2006-12-29 CA CA002635318A patent/CA2635318A1/fr not_active Abandoned
- 2006-12-29 CN CNA2006800499371A patent/CN101351211A/zh active Pending
- 2006-12-29 AU AU2006334359A patent/AU2006334359A1/en not_active Abandoned
- 2006-12-29 EP EP06830856A patent/EP1976533A2/fr not_active Withdrawn
- 2006-12-29 JP JP2008547980A patent/JP2009522239A/ja active Pending
- 2006-12-29 RU RU2008131311/04A patent/RU2008131311A/ru not_active Application Discontinuation
- 2006-12-29 BR BRPI0620845-2A patent/BRPI0620845A2/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006334359A1 (en) | 2007-07-12 |
| CN101351211A (zh) | 2009-01-21 |
| BRPI0620845A2 (pt) | 2011-11-22 |
| RU2008131311A (ru) | 2010-02-10 |
| WO2007077203A2 (fr) | 2007-07-12 |
| JP2009522239A (ja) | 2009-06-11 |
| KR20080083044A (ko) | 2008-09-12 |
| ES2277568A1 (es) | 2007-07-01 |
| WO2007077203A3 (fr) | 2007-08-30 |
| AU2006334359A2 (en) | 2008-08-07 |
| EP1976533A2 (fr) | 2008-10-08 |
| ES2277568B1 (es) | 2008-04-01 |
| MX2008008556A (es) | 2008-09-26 |
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| FZDE | Discontinued |