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
- Authority
- 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 US9701687B2 (en) | 2014-05-05 | 2015-04-17 | Process for the preparation of opioid compounds |
| US14/689,610 | 2015-04-17 | ||
| 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 (en:Method) | 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 (en:Method) |
| EP (1) | EP3140307A2 (en:Method) |
| JP (2) | JP2017514845A (en:Method) |
| CN (1) | CN107074869A (en:Method) |
| AU (1) | AU2015256507B2 (en:Method) |
| CA (1) | CA2947022A1 (en:Method) |
| WO (1) | WO2015171353A2 (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2016338925A1 (en) * | 2015-10-12 | 2018-05-31 | Noramco, Inc. | Process for the preparation of (S)-2-((4R,4aS, 6R,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 |
| WO2008064351A2 (en) | 2006-11-22 | 2008-05-29 | Progenics Pharmaceuticals, Inc. | (r)-n-stereoisomers of 7,8-saturated-4,5-epoxy-morphinanium analogs |
| 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 |
| CN101541808A (zh) * | 2007-05-04 | 2009-09-23 | 马林克罗特公司 | 制备6-α-羟基-N-烷基化的阿片的改进的方法 |
| EP2152715B1 (en) * | 2007-05-04 | 2010-12-29 | Mallinckrodt Inc. | Improved process for the preparation of 6-alpha-hydroxy-n-alkylated opiates |
| US8962841B2 (en) | 2007-06-29 | 2015-02-24 | Brock University | Methods for one-pot N-demethylation/N-functionalization of morphine and tropane alkaloids |
| CN101861315B (zh) | 2007-11-20 | 2013-01-16 | 日产化学工业株式会社 | 2-氮杂金刚烷类的制造方法 |
| CA2720034A1 (en) * | 2008-03-31 | 2009-10-08 | 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 |
| ES2477190T3 (es) | 2008-09-30 | 2014-07-16 | Mallinckrodt Llc | Procedimiento de reciclaje para aumentar el rendimiento de una reacción de Grignard en la preparación de derivados alcaloides opiáceos |
| WO2010039209A2 (en) | 2008-09-30 | 2010-04-08 | Mallinckrodt Inc. | Processes for the synthesis of tertiary amines |
| CA2738250C (en) | 2008-09-30 | 2018-08-14 | Mallinckrodt Inc. | Processes for increasing the yield of the hydrolysis of the 3-o-methyl and 17-n-nitrile group in the preparation of opiate alkaloid derivatives |
| WO2010039210A1 (en) | 2008-09-30 | 2010-04-08 | Mallinckrodt Inc. | Processes for the hydrogenation of opiate alkaloid derivatives |
| PL2342207T3 (pl) | 2008-09-30 | 2016-05-31 | SpecGx LLC | Sposoby alkilowania norbuprenorfiny ze zmniejszonym powstawaniem zanieczyszczeń |
| WO2010096416A1 (en) | 2009-02-17 | 2010-08-26 | Mallinckrodt Inc. | Process for the reductive alkylation of normorphinans |
| NZ595591A (en) | 2009-04-24 | 2013-11-29 | Univ Brock | Processes for the preparation of morphinane and morphinone compounds |
| US20110269964A1 (en) * | 2010-04-29 | 2011-11-03 | Mallinckrodt Inc. | N-Alkylation of Opiates |
| SMT201700177T1 (it) * | 2010-11-05 | 2017-05-08 | H Lundbeck As | Procedimento per la fabbricazione di naltrexone |
| JP6046119B2 (ja) | 2011-05-02 | 2016-12-14 | ブロック ユニバーシティ | 脱水環化試薬を使用するｎ−オキシドのｎ−脱メチル化によるモルヒネ類似体の調製における方法および中間体 |
| HUE040284T2 (hu) | 2011-10-03 | 2019-02-28 | Johnson Matthey Plc | Eljárás buprenorfin elõállítására |
| AU2013214667A1 (en) | 2012-02-03 | 2014-09-25 | Brock University | Process for the preparation of morphine analogs via the reaction of organometallic reagents with an oxazolidine derived from morphinans |
| US20140155608A1 (en) * | 2012-05-03 | 2014-06-05 | 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 WO PCT/US2015/027906 patent/WO2015171353A2/en not_active Ceased
- 2015-04-28 EP EP15726406.0A patent/EP3140307A2/en not_active Withdrawn
- 2015-04-28 CN CN201580035275.1A patent/CN107074869A/zh active Pending
- 2015-04-28 AU AU2015256507A patent/AU2015256507B2/en not_active Ceased
- 2015-04-28 JP JP2016565665A patent/JP2017514845A/ja active Pending
- 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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