JP2012527489A5 - - Google Patents
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- Publication number
- JP2012527489A5 JP2012527489A5 JP2012512208A JP2012512208A JP2012527489A5 JP 2012527489 A5 JP2012527489 A5 JP 2012527489A5 JP 2012512208 A JP2012512208 A JP 2012512208A JP 2012512208 A JP2012512208 A JP 2012512208A JP 2012527489 A5 JP2012527489 A5 JP 2012527489A5
- Authority
- JP
- Japan
- Prior art keywords
- mthf
- nalmefene
- methyltriphenylphosphonium
- naltrexone
- hcl
- 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
- 238000000034 method Methods 0.000 claims 15
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 8
- DQCKKXVULJGBQN-XFWGSAIBSA-N naltrexone Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=O)O)CC1)O)CC1CC1 DQCKKXVULJGBQN-XFWGSAIBSA-N 0.000 claims 5
- 229960003086 naltrexone Drugs 0.000 claims 5
- 239000007787 solid Substances 0.000 claims 5
- 239000007864 aqueous solution Substances 0.000 claims 4
- 238000002156 mixing Methods 0.000 claims 4
- 239000012074 organic phase Substances 0.000 claims 4
- GYWMRGWFQPSQLK-OPHZJPRHSA-N (4r,4as,7as,12bs)-3-(cyclopropylmethyl)-7-methylidene-2,4,5,6,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol;hydron;chloride Chemical compound Cl.N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=C)O)CC1)O)CC1CC1 GYWMRGWFQPSQLK-OPHZJPRHSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- WJBLNOPPDWQMCH-MBPVOVBZSA-N Nalmefene Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=C)O)CC1)O)CC1CC1 WJBLNOPPDWQMCH-MBPVOVBZSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical class C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 claims 3
- 229960005297 nalmefene Drugs 0.000 claims 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 3
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QRPRIOOKPZSVFN-UHFFFAOYSA-M methyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 QRPRIOOKPZSVFN-UHFFFAOYSA-M 0.000 claims 1
- JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 0.000 claims 1
- 229960000677 nalmefene hydrochloride Drugs 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000003039 volatile agent Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200900650 | 2009-05-25 | ||
| DKPA200900650 | 2009-05-25 | ||
| US18102209P | 2009-05-26 | 2009-05-26 | |
| US61/181,022 | 2009-05-26 | ||
| PCT/DK2010/050110 WO2010136039A1 (en) | 2009-05-25 | 2010-05-21 | Preparation of nalmefene hydrochloride from naltrexone |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012527489A JP2012527489A (ja) | 2012-11-08 |
| JP2012527489A5 true JP2012527489A5 (enExample) | 2013-06-27 |
| JP5794980B2 JP5794980B2 (ja) | 2015-10-14 |
Family
ID=43222172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012512208A Active JP5794980B2 (ja) | 2009-05-25 | 2010-05-21 | ナルトレキソンからの塩酸ナルメフェンの調製 |
Country Status (35)
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2645725T3 (es) | 2010-06-11 | 2017-12-07 | Rhodes Technologies | Procesos catalizados por metales de transición para la preparación de compuestos de N-alilo y uso de los mismos |
| EA022266B1 (ru) | 2010-11-05 | 2015-11-30 | Х. Лундбекк А/С | Способ получения налтрексона |
| CN103012416B (zh) * | 2011-09-28 | 2015-07-01 | 辽宁海思科制药有限公司 | 一种盐酸纳美芬的制备方法 |
| TWI560170B (en) | 2011-12-06 | 2016-12-01 | Lundbeck & Co As H | Process for recovery of nalmefene hydrochloride |
| CN102584840A (zh) * | 2011-12-28 | 2012-07-18 | 南京优科生物医药有限公司 | 一种制备纳美芬化合物的方法 |
| US20140155608A1 (en) | 2012-05-03 | 2014-06-05 | H. Lundbeck A/S | Method for the manufacturing of naltrexone |
| US20140005216A1 (en) | 2012-06-27 | 2014-01-02 | H. Lundbeck A/S | Nalmefene for reduction of alcohol consumption in specific target populations |
| CN103204859B (zh) * | 2013-04-25 | 2015-12-02 | 四川海思科制药有限公司 | 一种盐酸纳美芬化合物及其制备方法 |
| AR096851A1 (es) | 2013-07-11 | 2016-02-03 | H Lundbeck As | Sales que no forman hidratos ni solvatos de nalmefeno |
| AU2014368548B2 (en) | 2013-12-20 | 2019-09-19 | H. Lundbeck A/S | Use of an opioid receptor antagonist with kappa-activity and vortioxetine for treatment of depressive disorder with melancholic features |
| AU2015250611A1 (en) | 2014-04-22 | 2016-11-24 | H. Lundbeck A/S | Combination of brexpiprazole and nalmefene and use thereof for treating substance-related disorders |
| CN104513251A (zh) * | 2014-11-28 | 2015-04-15 | 安徽悦康凯悦制药有限公司 | 一种盐酸纳美芬的制备方法 |
| US9757372B2 (en) * | 2015-03-25 | 2017-09-12 | Taiwanj Pharmaceuticals Co., Ltd. | Toll-like receptor 4 antagonists and use in autoimmune liver diseases |
| RU2712232C1 (ru) * | 2018-10-05 | 2020-01-27 | Федеральное государственное унитарное предприятие "Научно-исследовательский институт гигиены, профпатологии и экологии человека" Федерального медико-биологического агентства | Улучшенный способ получения налмефена из налтрексона |
| US10927121B1 (en) | 2019-12-20 | 2021-02-23 | Southwest Research Institute | Technologies for removing residual solvent from nalmefene hydrochloride and producing crystalline nalmefene hydrochloride monohydrate, monosolvate, or crystalline nalmefene hydrochloride dihydrate |
| WO2022094470A1 (en) | 2020-11-02 | 2022-05-05 | Rhodes Technologies | Process for purifying noroxymorphone |
| WO2022165040A1 (en) | 2021-01-28 | 2022-08-04 | Rhodes Technologies | Process for crystallizing nalmefene hydrochloride |
| CN117843650A (zh) * | 2023-12-27 | 2024-04-09 | 南京海纳医药科技股份有限公司 | 一种盐酸纳美芬的精制方法 |
| CN117986261B (zh) * | 2024-04-02 | 2024-06-18 | 成都瑞尔医药科技有限公司 | 一种盐酸纳美芬母液的回收套用方法 |
| CN119080788A (zh) * | 2024-08-19 | 2024-12-06 | 南京海鲸药业股份有限公司 | 一种盐酸纳美芬杂质的去除监控系统及去除方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4341764A (en) | 1980-03-05 | 1982-07-27 | Cutter Laboratories, Inc. | Method of preparing fibronectin and antihemophilic factor |
| US4322426A (en) * | 1980-04-28 | 1982-03-30 | E. I. Du Pont De Nemours And Company | 17-Substituted-6-desoxy-7,8-dihydro-6α-methylnoroxymorphone narcotic antagonists |
| US4535157A (en) * | 1983-11-01 | 1985-08-13 | Key Pharmaceuticals, Inc. | Process for making 6-desoxy-6-methylenenaloxone and 6-desoxy-6-methylenenaltrexone |
| US4751307A (en) | 1985-01-17 | 1988-06-14 | Mallinckrodt, Inc. | Wittig-reaction processes |
| US4880813A (en) * | 1988-07-22 | 1989-11-14 | Baker Cummins Pharmaceuticals, Inc. | Method of treatment for allergic rhinitis |
| US7687646B2 (en) | 2006-03-28 | 2010-03-30 | Azad Pharmaceutical Ingredients, Ag | Polymorphic forms of olopatadine hydrochloride and methods for producing olopatadine and salts thereof |
| GB2447013A (en) * | 2007-03-01 | 2008-09-03 | Reckitt Benckiser Healthcare | Analgesic composition containing buprenorphone and nalmefene |
-
2010
- 2010-05-21 UA UAA201114599A patent/UA106752C2/uk unknown
- 2010-05-21 US US13/321,597 patent/US8598352B2/en active Active
- 2010-05-21 MA MA34465A patent/MA33368B1/fr unknown
- 2010-05-21 AU AU2010252392A patent/AU2010252392B2/en not_active Ceased
- 2010-05-21 WO PCT/DK2010/050110 patent/WO2010136039A1/en not_active Ceased
- 2010-05-21 EA EA201171461A patent/EA019331B1/ru not_active IP Right Cessation
- 2010-05-21 SI SI201031133A patent/SI2435439T1/sl unknown
- 2010-05-21 DK DK10720257.4T patent/DK2435439T3/en active
- 2010-05-21 CA CA2763093A patent/CA2763093C/en active Active
- 2010-05-21 SG SG2011086501A patent/SG176205A1/en unknown
- 2010-05-21 JP JP2012512208A patent/JP5794980B2/ja active Active
- 2010-05-21 RS RS20160137A patent/RS54599B1/sr unknown
- 2010-05-21 CN CN201080033670.3A patent/CN102459276B/zh not_active Expired - Fee Related
- 2010-05-21 HU HUE10720257A patent/HUE026892T2/en unknown
- 2010-05-21 PL PL10720257T patent/PL2435439T3/pl unknown
- 2010-05-21 ME MEP-2016-40A patent/ME02622B/me unknown
- 2010-05-21 NZ NZ596988A patent/NZ596988A/xx not_active IP Right Cessation
- 2010-05-21 BR BRPI1010975-7A patent/BRPI1010975B1/pt not_active IP Right Cessation
- 2010-05-21 MY MYPI2011005679A patent/MY158251A/en unknown
- 2010-05-21 ES ES10720257.4T patent/ES2564006T3/es active Active
- 2010-05-21 MX MX2011012502A patent/MX2011012502A/es active IP Right Grant
- 2010-05-21 KR KR1020117028079A patent/KR101716522B1/ko not_active Expired - Fee Related
- 2010-05-21 HR HRP20160110TT patent/HRP20160110T1/hr unknown
- 2010-05-21 GE GEAP201012510A patent/GEP20146190B/en unknown
- 2010-05-21 EP EP10720257.4A patent/EP2435439B8/en active Active
- 2010-05-24 TW TW99116496A patent/TWI469985B/zh not_active IP Right Cessation
- 2010-05-26 AR ARP100101818A patent/AR076891A1/es unknown
-
2011
- 2011-11-17 IL IL216422A patent/IL216422A/en not_active IP Right Cessation
- 2011-11-21 TN TNP2011000590A patent/TN2011000590A1/en unknown
- 2011-11-22 CR CR20110612A patent/CR20110612A/es unknown
- 2011-11-23 DO DO2011000362A patent/DOP2011000362A/es unknown
- 2011-11-24 CL CL2011002974A patent/CL2011002974A1/es unknown
- 2011-11-24 ZA ZA2011/08659A patent/ZA201108659B/en unknown
- 2011-11-25 CO CO11162008A patent/CO6470832A2/es active IP Right Grant
-
2016
- 2016-02-26 SM SM201600061T patent/SMT201600061B/it unknown
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