CA2950768C - Oxidative dearomatization of berbines - Google Patents
Oxidative dearomatization of berbines Download PDFInfo
- Publication number
- CA2950768C CA2950768C CA2950768A CA2950768A CA2950768C CA 2950768 C CA2950768 C CA 2950768C CA 2950768 A CA2950768 A CA 2950768A CA 2950768 A CA2950768 A CA 2950768A CA 2950768 C CA2950768 C CA 2950768C
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- CA
- Canada
- Prior art keywords
- halogen
- alkyl
- hydroxy
- hydrogen
- alkoxy
- 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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- 230000001590 oxidative effect Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims description 121
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- 229910052736 halogen Inorganic materials 0.000 claims description 105
- 150000002367 halogens Chemical group 0.000 claims description 105
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 81
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 56
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- 201000011510 cancer Diseases 0.000 claims description 28
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- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
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- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 claims 1
- BRLDZKPJJNASGG-KRWDZBQOSA-N alpha-berbine Chemical class C1=CC=C2CN3CCC4=CC=CC=C4[C@@H]3CC2=C1 BRLDZKPJJNASGG-KRWDZBQOSA-N 0.000 abstract description 22
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- 125000003107 substituted aryl group Chemical group 0.000 description 14
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- 235000019345 sodium thiosulphate Nutrition 0.000 description 10
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- 125000005017 substituted alkenyl group Chemical group 0.000 description 9
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- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
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- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 229960003048 vinblastine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound 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 description 1
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- FKBHRUQOROFRGD-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2[C]3C=CC=CC3=NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC FKBHRUQOROFRGD-IELIFDKJSA-N 0.000 description 1
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- 239000011718 vitamin C Substances 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US201462010648P | 2014-06-11 | 2014-06-11 | |
| US62/010,648 | 2014-06-11 | ||
| PCT/US2015/035300 WO2015191837A1 (en) | 2014-06-11 | 2015-06-11 | Oxidative dearomatization of berbines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2950768A1 CA2950768A1 (en) | 2015-12-17 |
| CA2950768C true CA2950768C (en) | 2023-03-28 |
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| CA2950768A Active CA2950768C (en) | 2014-06-11 | 2015-06-11 | Oxidative dearomatization of berbines |
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| EP (1) | EP3154968B1 (enExample) |
| JP (1) | JP6577491B2 (enExample) |
| AU (1) | AU2015274545B2 (enExample) |
| BR (1) | BR112016027834B1 (enExample) |
| CA (1) | CA2950768C (enExample) |
| ES (1) | ES2813678T3 (enExample) |
| MX (1) | MX376440B (enExample) |
| WO (1) | WO2015191837A1 (enExample) |
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| EP3055307B1 (en) * | 2013-10-04 | 2019-12-04 | SpecGx LLC | Substituted berbines and their synthesis |
| ES2813678T3 (es) | 2014-06-11 | 2021-03-24 | SpecGx LLC | Desaromatización oxidativa de berbinas |
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| JPS5019781A (enExample) * | 1973-06-25 | 1975-03-01 | ||
| JPS5116698A (en) * | 1974-07-27 | 1976-02-10 | Kanebo Ltd | Jibenzo * a*g * kinorijiniumujudotaino shinkigoseiho |
| US4033966A (en) | 1975-06-24 | 1977-07-05 | Kanebo, Ltd. | Novel berbine derivatives |
| KR100706309B1 (ko) * | 2006-02-14 | 2007-04-12 | 한국생명공학연구원 | 항진균 활성이 우수한 베르베루빈 유도체 |
| WO2010028004A2 (en) * | 2008-09-03 | 2010-03-11 | Mallinckrodt Inc. | Substituted berbines and processes for their synthesis |
| CN101665491B (zh) * | 2009-09-17 | 2011-09-28 | 长春工业大学 | 小檗碱13位衍生物和小檗红碱13位衍生物的合成方法 |
| CN101798285B (zh) * | 2010-02-10 | 2012-05-23 | 中国科学院上海有机化学研究所 | 一种青藤碱衍生物、合成方法及其用途 |
| JOP20200043A1 (ar) * | 2011-05-10 | 2017-06-16 | Amgen Inc | طرق معالجة أو منع الاضطرابات المختصة بالكوليسترول |
| CN102850346A (zh) * | 2012-09-27 | 2013-01-02 | 四川大学 | 小檗红碱12-位衍生物及其制备方法和用途 |
| ES2813678T3 (es) | 2014-06-11 | 2021-03-24 | SpecGx LLC | Desaromatización oxidativa de berbinas |
-
2015
- 2015-06-11 ES ES15806033T patent/ES2813678T3/es active Active
- 2015-06-11 JP JP2016569059A patent/JP6577491B2/ja active Active
- 2015-06-11 US US14/736,752 patent/US9593111B2/en active Active
- 2015-06-11 BR BR112016027834-8A patent/BR112016027834B1/pt active IP Right Grant
- 2015-06-11 WO PCT/US2015/035300 patent/WO2015191837A1/en not_active Ceased
- 2015-06-11 CA CA2950768A patent/CA2950768C/en active Active
- 2015-06-11 EP EP15806033.5A patent/EP3154968B1/en active Active
- 2015-06-11 MX MX2016015507A patent/MX376440B/es active IP Right Grant
- 2015-06-11 AU AU2015274545A patent/AU2015274545B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| MX2016015507A (es) | 2017-04-25 |
| WO2015191837A1 (en) | 2015-12-17 |
| JP6577491B2 (ja) | 2019-09-18 |
| AU2015274545A1 (en) | 2016-12-15 |
| MX376440B (es) | 2025-03-07 |
| ES2813678T3 (es) | 2021-03-24 |
| EP3154968B1 (en) | 2020-08-05 |
| EP3154968A4 (en) | 2018-02-07 |
| US9593111B2 (en) | 2017-03-14 |
| AU2015274545B2 (en) | 2019-02-28 |
| BR112016027834A2 (enExample) | 2017-08-22 |
| JP2017518987A (ja) | 2017-07-13 |
| CA2950768A1 (en) | 2015-12-17 |
| BR112016027834B1 (pt) | 2023-12-26 |
| US20150361076A1 (en) | 2015-12-17 |
| EP3154968A1 (en) | 2017-04-19 |
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