JP2017518987A5 - - Google Patents
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- Publication number
- JP2017518987A5 JP2017518987A5 JP2016569059A JP2016569059A JP2017518987A5 JP 2017518987 A5 JP2017518987 A5 JP 2017518987A5 JP 2016569059 A JP2016569059 A JP 2016569059A JP 2016569059 A JP2016569059 A JP 2016569059A JP 2017518987 A5 JP2017518987 A5 JP 2017518987A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- hydrogen
- halogen
- formula
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 239000001257 hydrogen Substances 0.000 claims description 72
- 150000002431 hydrogen Chemical group 0.000 claims description 59
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 150000003573 thiols Chemical class 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 230000005907 cancer growth Effects 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- -1 butoxides Chemical class 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 230000010261 cell growth Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2017518987A JP2017518987A (ja) | 2017-07-13 |
| JP2017518987A5 true JP2017518987A5 (enExample) | 2018-05-17 |
| JP6577491B2 JP6577491B2 (ja) | 2019-09-18 |
Family
ID=54834304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016569059A Active JP6577491B2 (ja) | 2014-06-11 | 2015-06-11 | ベルビンの酸化的脱芳香族化 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9593111B2 (enExample) |
| 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) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015051106A1 (en) * | 2013-10-04 | 2015-04-09 | Mallinckrodt Llc | Substituted berbines and their synthesis |
| CA2950768C (en) | 2014-06-11 | 2023-03-28 | Mallinckrodt Llc | Oxidative dearomatization of berbines |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US9458109B2 (en) * | 2008-09-03 | 2016-10-04 | Mallinckrodt Llc | 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 |
| CA2950768C (en) | 2014-06-11 | 2023-03-28 | Mallinckrodt Llc | Oxidative dearomatization of berbines |
-
2015
- 2015-06-11 CA CA2950768A patent/CA2950768C/en active Active
- 2015-06-11 WO PCT/US2015/035300 patent/WO2015191837A1/en not_active Ceased
- 2015-06-11 ES ES15806033T patent/ES2813678T3/es active Active
- 2015-06-11 EP EP15806033.5A patent/EP3154968B1/en active Active
- 2015-06-11 BR BR112016027834-8A patent/BR112016027834B1/pt active IP Right Grant
- 2015-06-11 US US14/736,752 patent/US9593111B2/en active Active
- 2015-06-11 AU AU2015274545A patent/AU2015274545B2/en active Active
- 2015-06-11 MX MX2016015507A patent/MX376440B/es active IP Right Grant
- 2015-06-11 JP JP2016569059A patent/JP6577491B2/ja active Active
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