JP2011500777A5 - - Google Patents
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- Publication number
- JP2011500777A5 JP2011500777A5 JP2010530560A JP2010530560A JP2011500777A5 JP 2011500777 A5 JP2011500777 A5 JP 2011500777A5 JP 2010530560 A JP2010530560 A JP 2010530560A JP 2010530560 A JP2010530560 A JP 2010530560A JP 2011500777 A5 JP2011500777 A5 JP 2011500777A5
- Authority
- JP
- Japan
- Prior art keywords
- odv
- disorder
- base
- pharmaceutically acceptable
- thiol reagent
- 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.)
- Pending
Links
- KYYIDSXMWOZKMP-UHFFFAOYSA-N O-desmethylvenlafaxine Chemical compound C1CCCCC1(O)C(CN(C)C)C1=CC=C(O)C=C1 KYYIDSXMWOZKMP-UHFFFAOYSA-N 0.000 claims 16
- 238000000034 method Methods 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 12
- 239000003774 sulfhydryl reagent Substances 0.000 claims 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- -1 aliphatic dithiol Chemical class 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000007810 chemical reaction solvent Substances 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 150000001450 anions Chemical class 0.000 claims 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 claims 4
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims 4
- 229960004688 venlafaxine Drugs 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 150000004703 alkoxides Chemical class 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 238000011065 in-situ storage Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 3
- 208000008811 Agoraphobia Diseases 0.000 claims 2
- 208000007848 Alcoholism Diseases 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 206010003805 Autism Diseases 0.000 claims 2
- 208000020706 Autistic disease Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 2
- 208000001640 Fibromyalgia Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000027030 Premenstrual dysphoric disease Diseases 0.000 claims 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims 2
- 206010041250 Social phobia Diseases 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 201000007930 alcohol dependence Diseases 0.000 claims 2
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 2
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 208000030963 borderline personality disease Diseases 0.000 claims 2
- 229960003920 cocaine Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000011010 flushing procedure Methods 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 231100000872 sexual dysfunction Toxicity 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- 150000003553 thiiranes Chemical class 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- 230000001457 vasomotor Effects 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 claims 1
- YBDSNEVSFQMCTL-UHFFFAOYSA-N 2-(diethylamino)ethanethiol Chemical group CCN(CC)CCS YBDSNEVSFQMCTL-UHFFFAOYSA-N 0.000 claims 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 150000001298 alcohols Chemical group 0.000 claims 1
- 125000005025 alkynylaryl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000004662 dithiols Chemical group 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 230000010354 integration Effects 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN2122MU2007 | 2007-10-26 | ||
| PCT/GB2008/050962 WO2009053731A1 (en) | 2007-10-26 | 2008-10-18 | Process for preparing o-desmethylvenlafaxine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011500777A JP2011500777A (ja) | 2011-01-06 |
| JP2011500777A5 true JP2011500777A5 (enExample) | 2011-12-08 |
Family
ID=40139287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010530560A Pending JP2011500777A (ja) | 2007-10-26 | 2008-10-18 | Ｏ−デスメチルベンラファキシンの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20110118357A1 (enExample) |
| EP (1) | EP2200968A1 (enExample) |
| JP (1) | JP2011500777A (enExample) |
| CN (1) | CN101952240A (enExample) |
| AU (1) | AU2008315740A1 (enExample) |
| CA (1) | CA2703647A1 (enExample) |
| NZ (1) | NZ585368A (enExample) |
| WO (1) | WO2009053731A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ303249B6 (cs) | 2010-04-06 | 2012-06-20 | Zentiva, K.S. | Zpusob výroby 4-(2-(substituovaných)-1-(1-hydroxycyklohexyl)ethyl)fenolu O-demethylací jejich methyletheru pomocí nepáchnoucích aromatických thiolu |
| EP2394976A1 (en) | 2010-06-11 | 2011-12-14 | LEK Pharmaceuticals d.d. | Process for demethylating aromatic methyl ethers using 3-mercaptopropionic acid |
| JP6751200B2 (ja) * | 2017-02-09 | 2020-09-02 | アール エル ファインケム プライベート リミテッド | １−［２−（ジメチルアミノ）−１−（４−ヒドロキシフェニル）エチル］−シクロヘキサノール及びその塩の製造方法 |
| CN106928073A (zh) * | 2017-03-27 | 2017-07-07 | 石家庄度恩医药科技有限公司 | 一种去甲文拉法辛的制备方法 |
| CN106995376A (zh) * | 2017-04-21 | 2017-08-01 | 上海华源医药科技发展有限公司 | 一种去甲文拉法辛的工业化生产工艺 |
| CN109665966A (zh) * | 2018-11-01 | 2019-04-23 | 山东蒲济医药科技有限公司 | 一种琥珀酸去甲文拉法辛化合物的制备方法 |
| CN114478271B (zh) * | 2021-12-13 | 2024-05-31 | 植恩生物技术股份有限公司 | 琥珀酸去甲文拉法辛制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4535186A (en) * | 1983-04-19 | 1985-08-13 | American Home Products Corporation | 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives |
| US4761501A (en) * | 1983-10-26 | 1988-08-02 | American Home Products Corporation | Substituted phenylacetamides |
| US6342533B1 (en) | 1998-12-01 | 2002-01-29 | Sepracor, Inc. | Derivatives of (−)-venlafaxine and methods of preparing and using the same |
| US6197828B1 (en) | 1998-12-01 | 2001-03-06 | Sepracor, Inc. | Derivatives of (+)-venlafaxine and methods of preparing and using the same |
| ES2305606T3 (es) | 1999-04-06 | 2008-11-01 | Sepracor Inc. | Succinato de o-desmetilvenlafaxina. |
| WO2000076955A1 (en) | 1999-06-15 | 2000-12-21 | American Home Products Corporation | Enantiomers of o-desmethyl venlafaxine |
| ATE369330T1 (de) | 2001-02-12 | 2007-08-15 | Wyeth Corp | O-desmethyl-venlafaxine succinat salz |
| UA80543C2 (en) * | 2001-12-04 | 2007-10-10 | Wyeth Corp | Method for the preparation of o-desmethylvenlafaxine |
| RU2004139075A (ru) * | 2002-06-10 | 2005-06-27 | Уайт (Us) | Новые формиат 0-десметилвенлафаксина |
| WO2007071404A1 (en) * | 2005-12-20 | 2007-06-28 | Synthon B.V. | Process for making desvenlafaxine |
| EP2007708A1 (en) * | 2006-04-17 | 2008-12-31 | Teva Pharmaceutical Industries Ltd | Substantially pure o-desmethylvenlafaxine and processes for preparing it |
| MX2007016179A (es) * | 2006-04-17 | 2008-03-11 | Teva Pharma | Formas cristalinas de o-desmetilvenlafaxina. |
| AR064987A1 (es) * | 2007-01-22 | 2009-05-06 | Medichem Sa | Proceso mejorado para sintetizar desvenlafaxina como base libre y sales o solvatos de la misma |
-
2008
- 2008-10-18 CA CA2703647A patent/CA2703647A1/en not_active Abandoned
- 2008-10-18 US US12/739,431 patent/US20110118357A1/en not_active Abandoned
- 2008-10-18 EP EP08806776A patent/EP2200968A1/en not_active Withdrawn
- 2008-10-18 NZ NZ585368A patent/NZ585368A/en not_active IP Right Cessation
- 2008-10-18 JP JP2010530560A patent/JP2011500777A/ja active Pending
- 2008-10-18 WO PCT/GB2008/050962 patent/WO2009053731A1/en not_active Ceased
- 2008-10-18 CN CN2008801227443A patent/CN101952240A/zh active Pending
- 2008-10-18 AU AU2008315740A patent/AU2008315740A1/en not_active Abandoned
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