JP2017514845A5 - - Google Patents
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- JP2017514845A5 JP2017514845A5 JP2016565665A JP2016565665A JP2017514845A5 JP 2017514845 A5 JP2017514845 A5 JP 2017514845A5 JP 2016565665 A JP2016565665 A JP 2016565665A JP 2016565665 A JP2016565665 A JP 2016565665A JP 2017514845 A5 JP2017514845 A5 JP 2017514845A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- molar equivalents
- present
- amine base
- 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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- 150000001875 compounds Chemical class 0.000 claims 71
- 238000000034 method Methods 0.000 claims 64
- 150000001412 amines Chemical class 0.000 claims 18
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 16
- 239000003960 organic solvent Substances 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 239000012649 demethylating agent Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 3
- 150000004703 alkoxides Chemical class 0.000 claims 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 229940043279 diisopropylamine Drugs 0.000 claims 1
- 0 CO[C@](CC1)(*[C@@](*)C[C@@]1(*1)[C@@](C2)C(CC3CC3)CC[C@@]11c3c2cc2)[C@@]1Oc3c2OC Chemical compound CO[C@](CC1)(*[C@@](*)C[C@@]1(*1)[C@@](C2)C(CC3CC3)CC[C@@]11c3c2cc2)[C@@]1Oc3c2OC 0.000 description 5
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461988508P | 2014-05-05 | 2014-05-05 | |
| US61/988,508 | 2014-05-05 | ||
| US14/689,610 | 2015-04-17 | ||
| US14/689,610 US9701687B2 (en) | 2014-05-05 | 2015-04-17 | Process for the preparation of opioid compounds |
| PCT/US2015/027906 WO2015171353A2 (en) | 2014-05-05 | 2015-04-28 | Process for the preparation of opioid compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020036660A Division JP2020203872A (ja) | 2014-05-05 | 2020-03-04 | オピオイド化合物を調製するプロセス |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017514845A JP2017514845A (ja) | 2017-06-08 |
| JP2017514845A5 true JP2017514845A5 (enExample) | 2018-06-14 |
Family
ID=54354747
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016565665A Pending JP2017514845A (ja) | 2014-05-05 | 2015-04-28 | オピオイド化合物を調製するプロセス |
| JP2020036660A Pending JP2020203872A (ja) | 2014-05-05 | 2020-03-04 | オピオイド化合物を調製するプロセス |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020036660A Pending JP2020203872A (ja) | 2014-05-05 | 2020-03-04 | オピオイド化合物を調製するプロセス |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9701687B2 (enExample) |
| EP (1) | EP3140307A2 (enExample) |
| JP (2) | JP2017514845A (enExample) |
| CN (1) | CN107074869A (enExample) |
| AU (1) | AU2015256507B2 (enExample) |
| CA (1) | CA2947022A1 (enExample) |
| WO (1) | WO2015171353A2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3001689A1 (en) * | 2015-10-12 | 2017-04-20 | Noramco, Inc. | Process for the preparation of (s)-2-((4r,4as,6r,7r,7ar,12bs)-7,9-dimethoxy-1,2,3,4,5,6,7,7a-octahydro-4a,7-ethano-4,12-methanobenzofuro[3,2-e]isoquinolin-6-yl)-3,3-dimethylbutan-2-ol |
| EP4686721A1 (en) | 2024-08-01 | 2026-02-04 | Siegfried AG | Crystalline naloxone-dimethylformamide solvate, methods for its preparation and its use as a reagent in a method of making naloxone |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3474101A (en) | 1960-09-05 | 1969-10-21 | Reckitt & Sons Ltd | Thebaine and oripavine derivatives |
| US20080125592A1 (en) | 2006-10-17 | 2008-05-29 | Penick Corporation | Process for preparing oxymorphone, naltrexone, and buprenorphine |
| CA2674915C (en) | 2006-10-17 | 2015-06-30 | Penick Corporation | Process for preparing oxymorphone |
| JP2010510328A (ja) * | 2006-11-22 | 2010-04-02 | プロジェニックス ファーマスーティカルス インコーポレーテッド | ７，８−飽和−４，５−エポキシ−モルフィナニウム類似体の（ｒ）−ｎ−立体異性体 |
| CN101636160A (zh) * | 2006-11-22 | 2010-01-27 | 普罗基因制药公司 | 7,8-饱和-4,5-环氧-吗啡烷离子类似物的(r)-n-立体异构体 |
| ATE493416T1 (de) | 2007-05-04 | 2011-01-15 | Mallinckrodt Inc | Verbessertes verfahren zur herstellung von 6- alpha-hydroxy-n-alkylierten opiaten |
| ES2356412T3 (es) * | 2007-05-04 | 2011-04-07 | Mallinckrodt Inc. | Procedimiento mejorado para la preparación de opiáceos 6-alfa-hidroxi-n-alquilados. |
| US8962841B2 (en) | 2007-06-29 | 2015-02-24 | Brock University | Methods for one-pot N-demethylation/N-functionalization of morphine and tropane alkaloids |
| EP2221306B1 (en) | 2007-11-20 | 2016-04-13 | Nissan Chemical Industries, Ltd. | Method for producing 2-azaadamantane |
| AU2009233315B2 (en) * | 2008-03-31 | 2013-08-29 | Sun Pharmaceutical Industries Ltd. | An improved process for the preparation of morphinane analogues |
| WO2010017573A1 (en) | 2008-08-11 | 2010-02-18 | Tasmanian Alkaloids Pty Limited | PROCESS FOR MAKING MORPHINAN-6α-OLS |
| WO2010039214A1 (en) | 2008-09-30 | 2010-04-08 | Mallinckrodt Inc. | Processes for increasing the yield of the hydrolysis of the 3-0-methyl and 17-n-nitrile group in the preparation of opiate alkaloid derivatives |
| US8293906B2 (en) | 2008-09-30 | 2012-10-23 | Mallinckrodt Llc | Processes for the alkylation of norbuprenorphine with reduced impurity formation |
| ES2566559T3 (es) | 2008-09-30 | 2016-04-13 | Mallinckrodt Llc | Procesos para la alquilación de grupos amino secundarios de derivados de morfinano |
| US8273887B2 (en) | 2008-09-30 | 2012-09-25 | Mallinckrodt Llc | Processes for synthesis of opiate alkaloid derivatives |
| PL2342208T3 (pl) | 2008-09-30 | 2014-11-28 | SpecGx LLC | Proces zawracania do ponownego wykorzystania w celu zwiększania wydajności reakcji grignarda w wytwarzaniu pochodnych alkaloidów opiatowych |
| US8431701B2 (en) | 2009-02-17 | 2013-04-30 | Mallinckrodt Llc | Process for the reductive alkylation of normorphinans |
| JP5824448B2 (ja) | 2009-04-24 | 2015-11-25 | ブロック ユニバーシティ | モルフィナンおよびモルフィノン化合物の調製法 |
| US20110269964A1 (en) * | 2010-04-29 | 2011-11-03 | Mallinckrodt Inc. | N-Alkylation of Opiates |
| DK2635586T3 (en) * | 2010-11-05 | 2017-03-27 | H Lundbeck As | PROCEDURE FOR THE PREPARATION OF NALTREXON |
| CN103596962B (zh) * | 2011-05-02 | 2017-02-15 | 布鲁克大学 | 通过使用环化脱水试剂的n‑氧化物的n‑脱甲基化制备吗啡类似物的方法和中间体 |
| HUE040284T2 (hu) | 2011-10-03 | 2019-02-28 | Johnson Matthey Plc | Eljárás buprenorfin elõállítására |
| EP2809674A4 (en) | 2012-02-03 | 2015-09-02 | Univ Brock | METHOD FOR THE PRODUCTION OF MORPHINE ANALOGUE BY REACTION OF ORGANOMETALLIC REAGENTS WITH AN OXAZOLIDINE DERIVED FROM MORPHINANESE |
| WO2013164383A1 (en) * | 2012-05-03 | 2013-11-07 | H. Lundbeck A/S | Method for the manufacturing of naltrexone |
-
2015
- 2015-04-17 US US14/689,610 patent/US9701687B2/en active Active
- 2015-04-28 JP JP2016565665A patent/JP2017514845A/ja active Pending
- 2015-04-28 CN CN201580035275.1A patent/CN107074869A/zh active Pending
- 2015-04-28 EP EP15726406.0A patent/EP3140307A2/en not_active Withdrawn
- 2015-04-28 WO PCT/US2015/027906 patent/WO2015171353A2/en not_active Ceased
- 2015-04-28 AU AU2015256507A patent/AU2015256507B2/en not_active Ceased
- 2015-04-28 CA CA2947022A patent/CA2947022A1/en not_active Abandoned
-
2020
- 2020-03-04 JP JP2020036660A patent/JP2020203872A/ja active Pending
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