JPH0432831B2 - - Google Patents
Info
- Publication number
- JPH0432831B2 JPH0432831B2 JP59230008A JP23000884A JPH0432831B2 JP H0432831 B2 JPH0432831 B2 JP H0432831B2 JP 59230008 A JP59230008 A JP 59230008A JP 23000884 A JP23000884 A JP 23000884A JP H0432831 B2 JPH0432831 B2 JP H0432831B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- desoxy
- reaction mixture
- item
- naltrexone
- 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.)
- Expired - Lifetime
Links
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 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 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 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 description 7
- 229960003086 naltrexone Drugs 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 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 description 5
- 229960005297 nalmefene Drugs 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 4
- 229960004127 naloxone Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003887 narcotic antagonist Substances 0.000 description 3
- 239000003401 opiate antagonist Substances 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 208000011117 substance-related disease Diseases 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010013654 Drug abuse Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000004081 narcotic agent Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZWYXFLVCZWQGA-UHFFFAOYSA-N (6-methylidenecyclohexa-2,4-dien-1-yl)-diphenylphosphanium;bromide Chemical compound [Br-].C=C1C=CC=CC1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 VZWYXFLVCZWQGA-UHFFFAOYSA-N 0.000 description 1
- -1 Alkali metal salts Chemical class 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010038678 Respiratory depression Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/06—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with a hetero atom directly attached in position 14
- C07D489/08—Oxygen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Addiction (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/547,676 US4535157A (en) | 1983-11-01 | 1983-11-01 | Process for making 6-desoxy-6-methylenenaloxone and 6-desoxy-6-methylenenaltrexone |
| US547676 | 1983-11-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60112792A JPS60112792A (ja) | 1985-06-19 |
| JPH0432831B2 true JPH0432831B2 (en:Method) | 1992-06-01 |
Family
ID=24185669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59230008A Granted JPS60112792A (ja) | 1983-11-01 | 1984-10-30 | ６―デスオキシー６―メチレンナロキソンおよび６―デスオキシー６―メチレンナルトレキソンの製法 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4535157A (en:Method) |
| EP (1) | EP0140367A3 (en:Method) |
| JP (1) | JPS60112792A (en:Method) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63500799A (ja) * | 1985-09-06 | 1988-03-24 | ベーカー・カミンス・ファーマシューティカルス・インコーポレーテッド | 持続性オピオイド拮抗作用を得るための方法および組成物 |
| US4722928A (en) * | 1985-12-02 | 1988-02-02 | E. I. Du Pont De Nemours And Company | N-oxide prodrug derivatives of 3-hydroxy morphinans and partial morphinans having improved oral bioavailability, pharmaceutical compositions, and processes |
| US5922705A (en) * | 1996-04-12 | 1999-07-13 | Intensive Narcotic Detoxification Centers Of America, Llc | Rapid narcotic detoxification |
| US5919760A (en) * | 1996-04-12 | 1999-07-06 | Intensive Narcotic Detoxification Centers Of America, Llc | Method for treating acute and severe diarrhea |
| US5783583A (en) * | 1996-04-12 | 1998-07-21 | Simon; David Lew | 17-(cyclopropylmethyl)-4,5alpha-epoxy-6-methylenemorphinan-3,14-diol, hydrochloride salt for the purpose of rapid narcotic detoxification |
| US6271240B1 (en) | 1996-05-06 | 2001-08-07 | David Lew Simon | Methods for improved regulation of endogenous dopamine in prolonged treatment of opioid addicted individuals |
| CN1050130C (zh) * | 1997-07-04 | 2000-03-08 | 卢正堂 | 纳洛酮酸脂和纳屈酮酸脂及系列物和制备方法 |
| EP1509182A4 (en) * | 2002-05-31 | 2009-12-30 | Titan Pharmaceuticals Inc | IMPLANTABLE POLYMERS DEVICE FOR THE DELAYED RELEASE OF BUPRENORPHINE |
| DE60329520D1 (de) * | 2002-11-08 | 2009-11-12 | Mallinckrodt Inc | Verfahren zur herstellung von quaternäre n-alkyl morphinan alkaloid salzen |
| US7399858B2 (en) * | 2002-11-11 | 2008-07-15 | Mallinckrodt Inc. | Method for the catalytic production of hydrocodone, hydromorphone, and derivatives thereof |
| US7323565B2 (en) * | 2002-11-11 | 2008-01-29 | Mallinckrodt Inc. | Method for the catalytic production of hydrocodone and hydromorphone |
| US7321038B2 (en) * | 2002-11-11 | 2008-01-22 | Mallinckrodt Inc. | Method for the catalytic production of hydrocodone and hydromorphone |
| MXPA05010450A (es) * | 2003-03-31 | 2005-11-04 | Titan Pharmaceuticals Inc | Dispositivo polimerico implantable para la liberacion prolongada de agonistas de dopamina. |
| CA2580694A1 (en) * | 2004-09-23 | 2006-03-30 | Alexander Michalow | Methods for regulating neurotransmitter systems by inducing counteradaptations |
| US20080045610A1 (en) * | 2004-09-23 | 2008-02-21 | Alexander Michalow | Methods for regulating neurotransmitter systems by inducing counteradaptations |
| CA2663909A1 (en) * | 2006-09-20 | 2008-03-27 | Mallinckrodt Inc. | Preparation of substituted morphinan-6-ones and salts and intermediates thereof |
| US9040726B2 (en) * | 2007-03-06 | 2015-05-26 | Mallinckrodt Llc | Process for the preparation of quaternary N-alkyl morphinan alkaloid salts |
| NZ579469A (en) * | 2007-03-06 | 2011-02-25 | Mallinckrodt Inc | Process for the preparation of quaternary n-alkyl morphinan alkaloid salts |
| ES2549904T3 (es) * | 2008-05-27 | 2015-11-03 | Mallinckrodt Llc | Procesos y compuestos para la preparación de normorfinanos |
| WO2010028004A2 (en) | 2008-09-03 | 2010-03-11 | Mallinckrodt Inc. | Substituted berbines and processes for their synthesis |
| UA102128C2 (en) | 2008-12-05 | 2013-06-10 | Х. Луннбек А/С | Nalmefene hydrochloride dihydrate |
| KR101716522B1 (ko) * | 2009-05-25 | 2017-03-14 | 하. 룬드벡 아크티에셀스카브 | 날트렉손으로부터의 날메펜 히드로클로라이드의 제조 |
| EP2580201B1 (en) | 2010-06-11 | 2017-08-02 | Rhodes Technologies | Transition metal-catalyzed processes for the preparation of n-allyl compounds and use thereof |
| WO2012059103A1 (en) * | 2010-11-05 | 2012-05-10 | H. Lundbeck A/S | Method for the manufacturing of naltrexone |
| 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 |
| WO2013164383A1 (en) | 2012-05-03 | 2013-11-07 | H. Lundbeck A/S | Method for the manufacturing of naltrexone |
| US20140005217A1 (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 |
| SG10201809280PA (en) | 2014-04-22 | 2018-11-29 | Otsuka Pharma Co Ltd | 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 |
| 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 |
| WO2022165040A1 (en) | 2021-01-28 | 2022-08-04 | Rhodes Technologies | Process for crystallizing nalmefene hydrochloride |
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3814768A (en) * | 1971-11-26 | 1974-06-04 | Lewenstein E | 6-methylene-6-desoxy dihydro morphine and codeine derivatives and pharmaceutically acceptable salts |
| 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 |
-
1983
- 1983-11-01 US US06/547,676 patent/US4535157A/en not_active Expired - Lifetime
-
1984
- 1984-10-30 EP EP84113052A patent/EP0140367A3/en not_active Withdrawn
- 1984-10-30 JP JP59230008A patent/JPS60112792A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0140367A3 (en) | 1988-07-20 |
| JPS60112792A (ja) | 1985-06-19 |
| US4535157A (en) | 1985-08-13 |
| EP0140367A2 (en) | 1985-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |