KR20080083044A - 트리테르펜퀴논 및 트리테르펜페놀 유도체와, 종양 및기생충성 질환의 치료를 위한 그 용도 - Google Patents
트리테르펜퀴논 및 트리테르펜페놀 유도체와, 종양 및기생충성 질환의 치료를 위한 그 용도 Download PDFInfo
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- KR20080083044A KR20080083044A KR1020087018837A KR20087018837A KR20080083044A KR 20080083044 A KR20080083044 A KR 20080083044A KR 1020087018837 A KR1020087018837 A KR 1020087018837A KR 20087018837 A KR20087018837 A KR 20087018837A KR 20080083044 A KR20080083044 A KR 20080083044A
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- South Korea
- Prior art keywords
- alkyl
- group
- unsubstituted
- substituted
- independently hydrogen
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 22
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 19
- 208000030852 Parasitic disease Diseases 0.000 title claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 44
- 201000010099 disease Diseases 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 239000000651 prodrug Substances 0.000 claims abstract description 25
- 229940002612 prodrug Drugs 0.000 claims abstract description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 799
- 239000001257 hydrogen Substances 0.000 claims description 799
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 704
- 125000000217 alkyl group Chemical group 0.000 claims description 513
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 374
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 370
- 125000003118 aryl group Chemical group 0.000 claims description 323
- 150000001875 compounds Chemical class 0.000 claims description 232
- 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 143
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 138
- 229910052799 carbon Inorganic materials 0.000 claims description 138
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 131
- 125000003277 amino group Chemical group 0.000 claims description 102
- 238000000034 method Methods 0.000 claims description 79
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 42
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 28
- -1 4,6b, 8a, 11,12b, 14a-hexamethyl-2,10-dioxo-2,6b, 7,8,8a, 9,10,11,12,12a, 12b, 13,14,14a- Tetradecahydro-picen-3-yl nicotinic acid ester Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 230000001404 mediated effect Effects 0.000 claims description 22
- HDIIUCVOZICRAQ-UHFFFAOYSA-N methyl 3,10-dihydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate Chemical compound CC1=C(O)C(=O)C=C2C(CCC3(C4CC(C(CC4(CCC33C)C)O)(C)C(=O)OC)C)(C)C3=CC=C21 HDIIUCVOZICRAQ-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- JFACETXYABVHFD-UHFFFAOYSA-N primisterin Chemical compound CC1=C(O)C(=O)C=C2C(CCC3(C)C4(C)CCC5(C)CCC(CC53)(C)C(=O)OC)(C)C4=CC=C21 JFACETXYABVHFD-UHFFFAOYSA-N 0.000 claims description 10
- ZADMHKPVSIUMDA-UHFFFAOYSA-N (9-hydroxy-4,6a,6b,8a,11,14a-hexamethyl-2,10-dioxo-7,8,9,11,12,12a,13,14-octahydropicen-3-yl) acetate Chemical compound CC1=C(OC(C)=O)C(=O)C=C2C(CCC3(C4CC(C(C(O)C4(CCC33C)C)=O)C)C)(C)C3=CC=C21 ZADMHKPVSIUMDA-UHFFFAOYSA-N 0.000 claims description 9
- YQUDHIFSNVKFLU-UHFFFAOYSA-N (9-hydroxy-4,6a,6b,8a,11,14a-hexamethyl-2,10-dioxo-7,8,9,11,12,12a,13,14-octahydropicen-3-yl) dodecanoate Chemical compound C1C(C)C(=O)C(O)C2(C)CCC3(C)C4=CC=C5C(C)=C(OC(=O)CCCCCCCCCCC)C(=O)C=C5C4(C)CCC3(C)C21 YQUDHIFSNVKFLU-UHFFFAOYSA-N 0.000 claims description 9
- XGZWQILSPYWGJA-UHFFFAOYSA-N (9-hydroxy-4,6a,6b,8a,11,14a-hexamethyl-2,10-dioxo-7,8,9,11,12,12a,13,14-octahydropicen-3-yl) n,n-dimethylcarbamate Chemical compound CC1=C(OC(=O)N(C)C)C(=O)C=C2C(CCC3(C4CC(C(C(O)C4(CCC33C)C)=O)C)C)(C)C3=CC=C21 XGZWQILSPYWGJA-UHFFFAOYSA-N 0.000 claims description 9
- ISVNJMOKAIZZAO-UHFFFAOYSA-N CCOC(=O)CCC(=O)OC1C(=O)C(C)CC2C1(C)CCC1(C)C3=CC=C4C(C)=C(O)C(=O)C=C4C3(C)CCC21C Chemical compound CCOC(=O)CCC(=O)OC1C(=O)C(C)CC2C1(C)CCC1(C)C3=CC=C4C(C)=C(O)C(=O)C=C4C3(C)CCC21C ISVNJMOKAIZZAO-UHFFFAOYSA-N 0.000 claims description 9
- SKPHMRFPHWROCY-UHFFFAOYSA-N OC1=C(C2=CC=C3C4(CCC5(C(C(C(CC5C4(CCC3(C2=CC1=O)C)C)C)=O)OC(CCC(=O)O)=O)C)C)C Chemical compound OC1=C(C2=CC=C3C4(CCC5(C(C(C(CC5C4(CCC3(C2=CC1=O)C)C)C)=O)OC(CCC(=O)O)=O)C)C)C SKPHMRFPHWROCY-UHFFFAOYSA-N 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- DIXKVSUALBFPHK-UHFFFAOYSA-N (9-hydroxy-4,6a,6b,8a,11,14a-hexamethyl-2,10-dioxo-7,8,9,11,12,12a,13,14-octahydropicen-3-yl) pyridine-3-carboxylate Chemical compound OC1C(=O)C(C)CC(C2(CCC3(C)C4=CC5=O)C)C1(C)CCC2(C)C3=CC=C4C(C)=C5OC(=O)C1=CC=CN=C1 DIXKVSUALBFPHK-UHFFFAOYSA-N 0.000 claims description 7
- IXPYLALKHKSDKR-UHFFFAOYSA-N 1,9-dihydropicene-2,10-dione Chemical compound C1C(=O)C=CC2=CC=C3C4=CC=C5CC(=O)C=CC5=C4C=CC3=C21 IXPYLALKHKSDKR-UHFFFAOYSA-N 0.000 claims description 7
- WSTYNZDAOAEEKG-UHFFFAOYSA-N 3-hydroxy-4,6a,6b,8a,11,14a-hexamethyl-7,8,9,11,12,12a,13,14-octahydropicene-2,10-dione Chemical compound CC1=C(O)C(=O)C=C2C(CCC3(C4CC(C(CC4(CCC33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- BCHDKANHNVHEMT-UHFFFAOYSA-N methyl 10-(dimethylcarbamoyloxy)-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate Chemical compound CC1=C(OC(=O)N(C)C)C(=O)C=C2C(CCC3(C)C4(C)CCC5(C)CCC(CC53)(C)C(=O)OC)(C)C4=CC=C21 BCHDKANHNVHEMT-UHFFFAOYSA-N 0.000 claims description 7
- JLEXIDDAUDXLOA-UHFFFAOYSA-N 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicen-3-one Chemical compound CC1=C(O)C(O)=CC2=C(CCC3(C4CC(C(CC4(CCC33C)C)=O)C)C)C3=CC=C21 JLEXIDDAUDXLOA-UHFFFAOYSA-N 0.000 claims description 6
- ZHAQHYYKWKPTLK-UHFFFAOYSA-N 10,11-dihydroxy-2,4a,6a,9,14a-pentamethyl-4,5,6,13,14,14b-hexahydropicen-3-one Chemical compound CC1=C(O)C(O)=CC2=C(CCC3(C4C=C(C(CC4(CCC33C)C)=O)C)C)C3=CC=C21 ZHAQHYYKWKPTLK-UHFFFAOYSA-N 0.000 claims description 6
- KQJSQWZMSAGSHN-UHFFFAOYSA-N 10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid Chemical compound CC12CCC3(C)C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C2=CC=C2C1=CC(=O)C(O)=C2C KQJSQWZMSAGSHN-UHFFFAOYSA-N 0.000 claims description 6
- HEQXBZZPYWEMJC-UHFFFAOYSA-N CC1CC2C(C)(CCC3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5C4(C)CCC23C)CC1O Chemical compound CC1CC2C(C)(CCC3(C)C4=CC=C5C(C)=C(O)C(=O)C=C5C4(C)CCC23C)CC1O HEQXBZZPYWEMJC-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- DNBZTECFUWBMRA-UHFFFAOYSA-N methyl 2,4a,6a,6a,9,14a-hexamethyl-11-oxo-10-propanoyloxy-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate Chemical compound C1C(C)(C(=O)OC)CCC2(C)CCC3(C)C4=CC=C5C(C)=C(OC(=O)CC)C(=O)C=C5C4(C)CCC3(C)C21 DNBZTECFUWBMRA-UHFFFAOYSA-N 0.000 claims description 6
- WLNFKDMGLUPVAE-UHFFFAOYSA-N methyl 7,10,11-trihydroxy-2,4a,6a,6a,9,14a-hexamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate Chemical compound OC1=C(O)C=C2C(CCC3(C)C4(C)CCC5(C)CCC(CC53)(C)C(=O)OC)(C)C4=C(O)C(=O)C2=C1C WLNFKDMGLUPVAE-UHFFFAOYSA-N 0.000 claims description 6
- HFOZJSCLBUTFCX-UHFFFAOYSA-N methyl 9-formyl-10,11-dihydroxy-2,4a,6a,6a,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylate Chemical compound OC1=C(O)C=C2C(CCC3(C)C4(C)CCC5(C)CCC(CC53)(C)C(=O)OC)(C)C4=CC(=O)C2=C1C=O HFOZJSCLBUTFCX-UHFFFAOYSA-N 0.000 claims description 6
- WTJTYAFIQLZLHS-UHFFFAOYSA-N 3-hydroxy-4,6a,6b,8a,11,14a-hexamethyl-7,8,9,12a,13,14-hexahydropicene-2,10-dione Chemical compound CC1=C(O)C(=O)C=C2C(CCC3(C4C=C(C(CC4(CCC33C)C)=O)C)C)(C)C3=CC=C21 WTJTYAFIQLZLHS-UHFFFAOYSA-N 0.000 claims description 5
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
- 208000031888 Mycoses Diseases 0.000 claims description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- PYCHVJVRDAIMEF-UHFFFAOYSA-N 2-(4,6a,6b,8a,11,14a-hexamethyl-2,10-dioxo-7,8,9,11,12,12a,13,14-octahydropicen-3-yl)acetic acid Chemical compound CC1=C(C(C=C2C3(CCC4(C5CC(C(CC5(CCC4(C3=CC=C12)C)C)=O)C)C)C)=O)CC(=O)O PYCHVJVRDAIMEF-UHFFFAOYSA-N 0.000 claims description 4
- IVPQILHVJAZSHF-UHFFFAOYSA-N OC1C2(CCC3(C4=CC=C5C(=C(C(C=C5C4(CCC3(C2CC(C1=O)C)C)C)=O)C(C(=O)O)C)C)C)C Chemical compound OC1C2(CCC3(C4=CC=C5C(=C(C(C=C5C4(CCC3(C2CC(C1=O)C)C)C)=O)C(C(=O)O)C)C)C)C IVPQILHVJAZSHF-UHFFFAOYSA-N 0.000 claims description 4
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 claims description 4
- MPTKUJGIEQFDGA-UHFFFAOYSA-N methyl 12-bromo-2,4a,6a,9,12a,14a-hexamethyl-10,11-dioxo-3,4,5,6,12,14b-hexahydro-1h-picene-2-carboxylate Chemical compound CC12C(Br)C(=O)C(=O)C(C)=C1C=CC1=C2C=CC2(C)C1(C)CCC1(C)CCC(C(=O)OC)(C)CC12 MPTKUJGIEQFDGA-UHFFFAOYSA-N 0.000 claims description 4
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- 201000005202 lung cancer Diseases 0.000 claims description 3
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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 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 3
- 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 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 2
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- 241000224016 Plasmodium Species 0.000 claims description 2
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- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 12
- 201000003741 Gastrointestinal carcinoma Diseases 0.000 claims 1
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims 1
- 102000002745 Choline Kinase Human genes 0.000 abstract description 36
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- 238000006243 chemical reaction Methods 0.000 description 9
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- 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 6
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- 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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- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Communicable Diseases (AREA)
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- Tropical Medicine & Parasitology (AREA)
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- Engineering & Computer Science (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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. |
ESP200503263 | 2005-12-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR20080083044A true KR20080083044A (ko) | 2008-09-12 |
Family
ID=37946257
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020087018837A KR20080083044A (ko) | 2005-12-30 | 2006-12-29 | 트리테르펜퀴논 및 트리테르펜페놀 유도체와, 종양 및기생충성 질환의 치료를 위한 그 용도 |
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 |
---|---|---|---|---|
JP4759612B2 (ja) | 2005-04-13 | 2011-08-31 | コンセホ スペリオール デ インベスティガシオネス シエンティフィカス | 癌治療化合物のin vitroにおける同定方法 |
US7776894B2 (en) | 2007-08-17 | 2010-08-17 | Burnham Institute For Medical Research | Compositions and methods for inhibiting growth and metastasis of melanoma |
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 |
EP3364956A4 (fr) | 2015-10-23 | 2019-05-01 | ERX Pharmaceuticals, Inc. | Analogues de célastrol |
EP3480207A4 (fr) | 2016-07-04 | 2020-03-11 | Xiamen University | Ligand de récepteur nucléaire orphelin nur77 et son application |
US10683292B2 (en) | 2016-07-25 | 2020-06-16 | Nerviano Medical Sciences S.R.L. | Purine and 3-deazapurine analogues as choline kinase inhibitors |
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 CA CA002635318A patent/CA2635318A1/fr not_active Abandoned
- 2006-12-29 JP JP2008547980A patent/JP2009522239A/ja active Pending
- 2006-12-29 KR KR1020087018837A patent/KR20080083044A/ko not_active Application Discontinuation
- 2006-12-29 EP EP06830856A patent/EP1976533A2/fr not_active Withdrawn
- 2006-12-29 WO PCT/EP2006/070276 patent/WO2007077203A2/fr active Application Filing
- 2006-12-29 BR BRPI0620845-2A patent/BRPI0620845A2/pt not_active Application Discontinuation
- 2006-12-29 RU RU2008131311/04A patent/RU2008131311A/ru not_active Application Discontinuation
- 2006-12-29 CN CNA2006800499371A patent/CN101351211A/zh active Pending
- 2006-12-29 MX MX2008008556A patent/MX2008008556A/es unknown
- 2006-12-29 AU AU2006334359A patent/AU2006334359A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
ES2277568B1 (es) | 2008-04-01 |
BRPI0620845A2 (pt) | 2011-11-22 |
JP2009522239A (ja) | 2009-06-11 |
RU2008131311A (ru) | 2010-02-10 |
AU2006334359A1 (en) | 2007-07-12 |
EP1976533A2 (fr) | 2008-10-08 |
AU2006334359A2 (en) | 2008-08-07 |
CN101351211A (zh) | 2009-01-21 |
CA2635318A1 (fr) | 2007-07-12 |
ES2277568A1 (es) | 2007-07-01 |
MX2008008556A (es) | 2008-09-26 |
WO2007077203A3 (fr) | 2007-08-30 |
WO2007077203A2 (fr) | 2007-07-12 |
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