JP2015524407A5 - - Google Patents
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- Publication number
- JP2015524407A5 JP2015524407A5 JP2015522183A JP2015522183A JP2015524407A5 JP 2015524407 A5 JP2015524407 A5 JP 2015524407A5 JP 2015522183 A JP2015522183 A JP 2015522183A JP 2015522183 A JP2015522183 A JP 2015522183A JP 2015524407 A5 JP2015524407 A5 JP 2015524407A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- compound
- reaction mixture
- alkyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 33
- 238000000034 method Methods 0.000 claims 29
- 239000002253 acid Substances 0.000 claims 21
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 16
- 239000011541 reaction mixture Substances 0.000 claims 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 14
- 239000012453 solvate Substances 0.000 claims 13
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 12
- 150000004965 peroxy acids Chemical class 0.000 claims 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 8
- 235000019253 formic acid Nutrition 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 238000011065 in-situ storage Methods 0.000 claims 5
- 239000000725 suspension Substances 0.000 claims 5
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims 4
- 239000012296 anti-solvent Substances 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 239000007800 oxidant agent Substances 0.000 claims 4
- 238000007254 oxidation reaction Methods 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KVIHITVCLHMLKV-ISWURRPUSA-N [(4R,4aS,7aR,12bS)-4a-hydroxy-3-methyl-7-oxo-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl] hydrogen sulfate Chemical group S(=O)(=O)(O)OC=1C=CC=2C[C@@H]3[C@@]4(C=CC([C@H]5[C@@]4(C=2C=1O5)CCN3C)=O)O KVIHITVCLHMLKV-ISWURRPUSA-N 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 230000001376 precipitating effect Effects 0.000 claims 3
- ZKLXUUYLEHCAMF-UUWFMWQGSA-N Oripavine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 ZKLXUUYLEHCAMF-UUWFMWQGSA-N 0.000 claims 2
- ZKLXUUYLEHCAMF-UHFFFAOYSA-N Oripavine Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(O)C5=C4C23C1O5 ZKLXUUYLEHCAMF-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000006370 trihalo methyl group Chemical group 0.000 claims 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical group O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000004683 dihydrates Chemical class 0.000 claims 1
- 150000004687 hexahydrates Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 229960005118 oxymorphone Drugs 0.000 claims 1
- 150000004686 pentahydrates Chemical class 0.000 claims 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 claims 1
- YOURVSNPCBPILN-UHFFFAOYSA-M potassium hydrogen sulfate hydroxy hydrogen sulfate Chemical compound [K+].OS([O-])(=O)=O.OOS(O)(=O)=O YOURVSNPCBPILN-UHFFFAOYSA-M 0.000 claims 1
- 150000004685 tetrahydrates Chemical class 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 150000004684 trihydrates Chemical class 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261672260P | 2012-07-16 | 2012-07-16 | |
| US61/672,260 | 2012-07-16 | ||
| US201261741480P | 2012-07-19 | 2012-07-19 | |
| US61/741,480 | 2012-07-19 | ||
| US201361762637P | 2013-02-08 | 2013-02-08 | |
| US61/762,637 | 2013-02-08 | ||
| PCT/IB2013/001541 WO2014013313A1 (en) | 2012-07-16 | 2013-07-15 | Process for improved opioid synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015524407A JP2015524407A (ja) | 2015-08-24 |
| JP2015524407A5 true JP2015524407A5 (enExample) | 2016-08-18 |
| JP6236447B2 JP6236447B2 (ja) | 2017-11-22 |
Family
ID=48916127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015522183A Active JP6236447B2 (ja) | 2012-07-16 | 2013-07-15 | 改善されたオピオイド合成方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US10316042B2 (enExample) |
| EP (1) | EP2872516B1 (enExample) |
| JP (1) | JP6236447B2 (enExample) |
| KR (1) | KR101946103B1 (enExample) |
| CN (1) | CN104470928B (enExample) |
| AR (1) | AR092858A1 (enExample) |
| AU (2) | AU2013291725B2 (enExample) |
| BR (1) | BR112015000944A2 (enExample) |
| CA (2) | CA2974010A1 (enExample) |
| CO (1) | CO7180188A2 (enExample) |
| EA (1) | EA028092B1 (enExample) |
| ES (1) | ES2647949T3 (enExample) |
| IL (1) | IL236710B (enExample) |
| IN (1) | IN2015DN01165A (enExample) |
| MX (1) | MX363610B (enExample) |
| NZ (1) | NZ628699A (enExample) |
| PH (1) | PH12015500089B1 (enExample) |
| SG (1) | SG11201407988UA (enExample) |
| TW (2) | TWI643859B (enExample) |
| UA (1) | UA117225C2 (enExample) |
| WO (1) | WO2014013313A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5923827B2 (ja) * | 1981-12-16 | 1984-06-05 | フエザ−安全剃刀株式会社 | 安全かみそり刃 |
| CN104507947B (zh) | 2012-07-16 | 2017-06-27 | 罗德科技公司 | 用于改进的阿片样物质合成的方法 |
| CA2919602C (en) * | 2013-08-02 | 2018-03-13 | Johnson Matthey Public Limited Company | Process for the preparation of oxymorphone |
| US9938285B2 (en) | 2014-01-15 | 2018-04-10 | Rhodes Technologies | Process for improved oxymorphone synthesis |
| EP3094634A1 (en) | 2014-01-15 | 2016-11-23 | Rhodes Technologies | Process for improved oxycodone synthesis |
| CA2954600A1 (en) * | 2014-07-09 | 2016-01-14 | Rhodes Technologies | Reduction of alpha, beta-unsaturated ketone levels in morphinan derivative compositions |
| US20160052932A1 (en) | 2014-08-25 | 2016-02-25 | Johnson Matthey Public Limited Company | Processes for Making Opioids Including 14-Hydroxycodeinone and 14-hydroxymorphinone |
| US20160340362A1 (en) * | 2015-05-20 | 2016-11-24 | Noramco, Inc. | Process For The Preparation Of Oxymorphone Freebase |
| EP3252055B1 (en) | 2016-05-31 | 2018-09-19 | Alcaliber Investigacion Desarrollo e Innovacion SLU | Process for obtaining 3,14-diacetyloxymorphone from oripavine |
| US10935314B2 (en) * | 2019-03-21 | 2021-03-02 | Evan Prout | Heating values of cellulosic waste |
| CN113493460A (zh) * | 2020-03-20 | 2021-10-12 | 江苏恩华药业股份有限公司 | 盐酸羟考酮杂质b的制备方法 |
| WO2022094470A1 (en) | 2020-11-02 | 2022-05-05 | Rhodes Technologies | Process for purifying noroxymorphone |
| US11247999B1 (en) | 2021-07-02 | 2022-02-15 | Joseph DeGraw | Facile conversion of morphine to normorphine |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2772270A (en) * | 1954-10-21 | 1956-11-27 | M J Lewenstein | 14-hydroxymorphinone and 8, 14-dihydroxydihydromorphinone |
| US3173876A (en) | 1960-05-27 | 1965-03-16 | John C Zobrist | Cleaning methods and compositions |
| NL271831A (enExample) | 1960-11-29 | |||
| US3276586A (en) | 1963-08-30 | 1966-10-04 | Rosaen Filter Co | Indicating means for fluid filters |
| NL6714885A (enExample) | 1967-11-02 | 1969-05-06 | ||
| US3541006A (en) | 1968-07-03 | 1970-11-17 | Amicon Corp | Ultrafiltration process |
| US3541005A (en) | 1969-02-05 | 1970-11-17 | Amicon Corp | Continuous ultrafiltration of macromolecular solutions |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| GB1478759A (en) | 1974-11-18 | 1977-07-06 | Alza Corp | Process for forming outlet passageways in pills using a laser |
| US4077407A (en) | 1975-11-24 | 1978-03-07 | Alza Corporation | Osmotic devices having composite walls |
| US4063064A (en) | 1976-02-23 | 1977-12-13 | Coherent Radiation | Apparatus for tracking moving workpiece by a laser beam |
| US4285987A (en) | 1978-10-23 | 1981-08-25 | Alza Corporation | Process for manufacturing device with dispersion zone |
| US4200098A (en) | 1978-10-23 | 1980-04-29 | Alza Corporation | Osmotic system with distribution zone for dispensing beneficial agent |
| US4861598A (en) | 1986-07-18 | 1989-08-29 | Euroceltique, S.A. | Controlled release bases for pharmaceuticals |
| DE3812567A1 (de) | 1988-04-15 | 1989-10-26 | Basf Ag | Verfahren zur herstellung pharmazeutischer mischungen |
| US5215758A (en) | 1991-09-11 | 1993-06-01 | Euroceltique, S.A. | Controlled release matrix suppository for pharmaceuticals |
| US5472712A (en) | 1991-12-24 | 1995-12-05 | Euroceltique, S.A. | Controlled-release formulations coated with aqueous dispersions of ethylcellulose |
| US5273760A (en) | 1991-12-24 | 1993-12-28 | Euroceltigue, S.A. | Stabilized controlled release substrate having a coating derived from an aqueous dispersion of hydrophobic polymer |
| US5286493A (en) | 1992-01-27 | 1994-02-15 | Euroceltique, S.A. | Stabilized controlled release formulations having acrylic polymer coating |
| US5324351A (en) | 1992-08-13 | 1994-06-28 | Euroceltique | Aqueous dispersions of zein and preparation thereof |
| AU2002316738B2 (en) | 2001-07-18 | 2009-01-08 | Euro-Celtique S.A. | Pharmaceutical combinations of oxycodone and naloxone |
| US6864370B1 (en) * | 2003-06-05 | 2005-03-08 | Zhaiwei Lin | Process for manufacturing oxycodone |
| US20050203115A1 (en) * | 2004-03-10 | 2005-09-15 | Sancilio Frederick D. | Narcotic-NSAID ion pairs |
| TW201509943A (zh) | 2004-03-30 | 2015-03-16 | Euro Celtique Sa | 含有小於２５ｐｐｍ１４-羥可待因酮之羥可酮鹽酸鹽之組成物、醫藥劑型、延遲釋出口服劑型及醫藥上可以接受的包裝 |
| SK286087B6 (sk) * | 2004-08-18 | 2008-03-05 | Zentiva, A. S. | Spôsob prípravy oxykodonu |
| GB0421149D0 (en) | 2004-09-23 | 2004-10-27 | Johnson Matthey Plc | Preparation of oxycodone |
| US8703099B2 (en) * | 2005-02-24 | 2014-04-22 | Dr Pharma Nova, Llc | Registry method and control system for DEA schedule II-V medicines |
| DE602006019246D1 (de) | 2005-06-16 | 2011-02-10 | Mallinckrodt Inc | Synthetische route zu 14-hydroxylopiaten über 1-halogenthebain oder analoga |
| KR100753432B1 (ko) | 2005-11-08 | 2007-08-31 | 경희대학교 산학협력단 | 다결정 실리콘 및 그의 결정화 방법 |
| US20070117826A1 (en) * | 2005-11-23 | 2007-05-24 | Forest Laboratories, Inc. | Pharmaceutical formulations comprising ibuprofen, oxycodone, and 14-hydroxycodeinone |
| AU2007313103C1 (en) * | 2006-10-17 | 2014-01-30 | Penick Corporation | Process for preparing oxymorphone |
| JP2010511725A (ja) * | 2006-12-04 | 2010-04-15 | ノランコ・インコーポレーテツド | オキシコドン塩基中の不純物を減少させる方法 |
| CA2671518C (en) | 2006-12-04 | 2016-06-07 | Noramco, Inc. | Process for preparing oxycodone having reduced levels of 14-hydroxycodeinone |
| GB0624880D0 (en) | 2006-12-14 | 2007-01-24 | Johnson Matthey Plc | Improved method for making analgesics |
| US8217175B2 (en) | 2007-03-23 | 2012-07-10 | Mallinckrodt Llc | Preparation of oxymorphone from oripavine |
| WO2008130553A1 (en) * | 2007-04-16 | 2008-10-30 | Mallinckrodt Inc. | Novel opiate reduction utilizing catalytic hydrogen transfer reaction |
| CN102458659B (zh) | 2009-06-03 | 2014-07-09 | 高砂香料工业株式会社 | 不对称氢化催化剂 |
| US9073934B2 (en) | 2009-09-16 | 2015-07-07 | Monash University | Method for the N-demethylation of N-methyl heterocycles |
| EP2377866B1 (en) * | 2010-03-23 | 2014-02-26 | Siegfried AG | Preparation of low impurity opiates in a continuous flow reactor |
| WO2011154826A1 (en) * | 2010-06-11 | 2011-12-15 | Rhodes Technologies | Process for n-dealkylation of tertiary amines |
| AU2011274361B2 (en) * | 2010-07-02 | 2014-09-18 | Macfarlan Smith Limited | Process for the synthesis and purification of oxycodone |
| NZ605234A (en) | 2010-07-08 | 2015-02-27 | Alkermes Pharma Ireland Ltd | Process for the synthesis of substituted morphinans |
| JP5780933B2 (ja) | 2010-12-01 | 2015-09-16 | 高砂香料工業株式会社 | 光学活性メントールの製造方法 |
| US9657029B2 (en) | 2012-06-11 | 2017-05-23 | Siegfried Generics International Ag | Method of preparing oxymorphone |
| CN104507947B (zh) * | 2012-07-16 | 2017-06-27 | 罗德科技公司 | 用于改进的阿片样物质合成的方法 |
| CN103113378B (zh) | 2013-02-20 | 2016-04-06 | 北京华素制药股份有限公司 | 一种盐酸羟吗啡酮的合成方法 |
| CN103433076B (zh) | 2013-09-02 | 2015-06-24 | 浙江新和成股份有限公司 | 一种固载型不对称催化剂及其在不对称氢化反应中的应用 |
| US8846923B1 (en) | 2013-12-18 | 2014-09-30 | Cody Laboratories, Inc. | Preparation of 14-hydroxycodeinone sulfate |
| US10227354B2 (en) | 2013-12-18 | 2019-03-12 | Cody Laboratories, Inc. | Conversion of oxycodone base to oxycodone hydrochloride |
| CA2934527A1 (en) | 2013-12-18 | 2015-06-25 | Cody Laboratories, Inc. | Synthesis of oxycodone hydrochloride |
| US9062062B1 (en) | 2013-12-18 | 2015-06-23 | Cody Laboratories, Inc. | Synthesis of oxycodone hydrochloride |
| US9938285B2 (en) | 2014-01-15 | 2018-04-10 | Rhodes Technologies | Process for improved oxymorphone synthesis |
| EP3094634A1 (en) | 2014-01-15 | 2016-11-23 | Rhodes Technologies | Process for improved oxycodone synthesis |
-
2013
- 2013-07-15 TW TW102125210A patent/TWI643859B/zh active
- 2013-07-15 AR ARP130102525A patent/AR092858A1/es not_active Application Discontinuation
- 2013-07-15 BR BR112015000944A patent/BR112015000944A2/pt not_active Application Discontinuation
- 2013-07-15 CA CA2974010A patent/CA2974010A1/en not_active Abandoned
- 2013-07-15 US US14/413,362 patent/US10316042B2/en active Active
- 2013-07-15 KR KR1020157003907A patent/KR101946103B1/ko active Active
- 2013-07-15 CA CA2879270A patent/CA2879270C/en active Active
- 2013-07-15 SG SG11201407988UA patent/SG11201407988UA/en unknown
- 2013-07-15 AU AU2013291725A patent/AU2013291725B2/en active Active
- 2013-07-15 CN CN201380037932.7A patent/CN104470928B/zh active Active
- 2013-07-15 TW TW105114709A patent/TWI643860B/zh active
- 2013-07-15 EA EA201590222A patent/EA028092B1/ru not_active IP Right Cessation
- 2013-07-15 WO PCT/IB2013/001541 patent/WO2014013313A1/en not_active Ceased
- 2013-07-15 EP EP13745178.7A patent/EP2872516B1/en active Active
- 2013-07-15 JP JP2015522183A patent/JP6236447B2/ja active Active
- 2013-07-15 NZ NZ628699A patent/NZ628699A/en unknown
- 2013-07-15 MX MX2015000879A patent/MX363610B/es unknown
- 2013-07-15 UA UAA201501303A patent/UA117225C2/uk unknown
- 2013-07-15 ES ES13745178.7T patent/ES2647949T3/es active Active
-
2015
- 2015-01-13 IL IL236710A patent/IL236710B/en active IP Right Grant
- 2015-01-14 PH PH12015500089A patent/PH12015500089B1/en unknown
- 2015-01-29 CO CO15018243A patent/CO7180188A2/es unknown
- 2015-02-12 IN IN1165DEN2015 patent/IN2015DN01165A/en unknown
-
2016
- 2016-07-14 AU AU2016204926A patent/AU2016204926A1/en not_active Abandoned
-
2019
- 2019-04-17 US US16/386,532 patent/US20190367526A1/en not_active Abandoned
-
2022
- 2022-09-21 US US17/949,681 patent/US20230130617A1/en active Pending
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