JP2016507483A5 - - Google Patents
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- Publication number
- JP2016507483A5 JP2016507483A5 JP2015546455A JP2015546455A JP2016507483A5 JP 2016507483 A5 JP2016507483 A5 JP 2016507483A5 JP 2015546455 A JP2015546455 A JP 2015546455A JP 2015546455 A JP2015546455 A JP 2015546455A JP 2016507483 A5 JP2016507483 A5 JP 2016507483A5
- Authority
- JP
- Japan
- Prior art keywords
- ring
- vinca alkaloid
- salt
- alkaloid compound
- hydrocarbyl
- 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
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 229940122803 Vinca alkaloid Drugs 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000006413 ring segment Chemical group 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- -1 perfluoro Chemical group 0.000 claims description 12
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical group [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 7
- 229960003048 vinblastine Drugs 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 5
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical class C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 230000010261 cell growth Effects 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 3
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Chemical class C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000000338 in vitro Methods 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229960004528 vincristine Drugs 0.000 claims description 2
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Chemical class C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 2
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical class C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 2
- 229960004355 vindesine Drugs 0.000 claims description 2
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical class C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 210000004027 cell Anatomy 0.000 description 9
- 102000004243 Tubulin Human genes 0.000 description 6
- 108090000704 Tubulin Proteins 0.000 description 6
- 238000011534 incubation Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 210000004292 cytoskeleton Anatomy 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261732687P | 2012-12-03 | 2012-12-03 | |
| US61/732,687 | 2012-12-03 | ||
| PCT/US2013/056459 WO2014088657A1 (en) | 2012-12-03 | 2013-08-23 | C20'-urea derivatives of vinca alkaloids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016507483A JP2016507483A (ja) | 2016-03-10 |
| JP2016507483A5 true JP2016507483A5 (https=) | 2016-10-13 |
| JP6326697B2 JP6326697B2 (ja) | 2018-05-23 |
Family
ID=50883853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015546455A Expired - Fee Related JP6326697B2 (ja) | 2012-12-03 | 2013-08-23 | ビンカアルカロイドのｃ２０’−尿素誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9611271B2 (https=) |
| EP (1) | EP2925760B1 (https=) |
| JP (1) | JP6326697B2 (https=) |
| AU (1) | AU2013356664B2 (https=) |
| CA (1) | CA2893200C (https=) |
| WO (1) | WO2014088657A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3464289B1 (en) * | 2016-05-31 | 2021-04-21 | The Scripps Research Institute | Ultra-potent vinca alkaloids: added molecular complexity further disrupts the tubulin dimer-dimer interface |
| CA2993378C (en) * | 2017-09-15 | 2021-10-05 | The Scripps Research Institute | Vinblastine 20' amides: synthetic analogs that maintain or improve potency and simultaneously overcome pgp-derived efflux and resistance |
| CN108675992B (zh) * | 2018-06-20 | 2020-11-27 | 浙江药苑生物科技有限公司 | 一种作用于微管蛋白的抗肿瘤药物 |
| CN108864053B (zh) * | 2018-06-20 | 2020-12-01 | 浙江药苑生物科技有限公司 | 一种微管蛋白抑制剂及其在抗肿瘤药物中的应用 |
| KR20260040225A (ko) * | 2023-06-13 | 2026-03-24 | 유니버시티 오브 조지아 리서치 파운데이션, 인코포레이티드 | 플라스모디움 팔시파룸 혈액 단계 억제제 |
| WO2026007326A1 (zh) * | 2024-07-01 | 2026-01-08 | 四川大学 | 长春碱衍生物的制备及其应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322351A (en) * | 1980-08-25 | 1982-03-30 | Eli Lilly And Company | Antineoplastic 4'-formylamino and 4'-acetylamino VLB, and derivatives thereof |
| EP2382995A3 (en) * | 2005-08-19 | 2013-09-25 | Endocyte, Inc. | Ligand conjugates of Vinca alkaloids, analogs and derivatives |
| EP1989212B1 (en) * | 2006-02-17 | 2013-06-19 | Cascade Prodrug Inc. | Treatment of hyperproliferative diseases with vinca alkaloid n-oxide and analogs |
| US8039453B2 (en) * | 2006-09-12 | 2011-10-18 | Albany Molecular Research, Inc. | Vinca derivatives |
| WO2011103007A2 (en) * | 2010-02-22 | 2011-08-25 | The Scripps Research Institute | 10'-fluorinated vinca alkaloids provide enhanced biological activity against mdr cancer cells |
-
2013
- 2013-08-23 US US14/648,624 patent/US9611271B2/en not_active Expired - Fee Related
- 2013-08-23 JP JP2015546455A patent/JP6326697B2/ja not_active Expired - Fee Related
- 2013-08-23 EP EP13860128.1A patent/EP2925760B1/en active Active
- 2013-08-23 CA CA2893200A patent/CA2893200C/en active Active
- 2013-08-23 WO PCT/US2013/056459 patent/WO2014088657A1/en not_active Ceased
- 2013-08-23 AU AU2013356664A patent/AU2013356664B2/en not_active Ceased
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