UA80543C2 - Method for the preparation of o-desmethylvenlafaxine - Google Patents
Method for the preparation of o-desmethylvenlafaxine Download PDFInfo
- Publication number
- UA80543C2 UA80543C2 UA20040705306A UA20040705306A UA80543C2 UA 80543 C2 UA80543 C2 UA 80543C2 UA 20040705306 A UA20040705306 A UA 20040705306A UA 20040705306 A UA20040705306 A UA 20040705306A UA 80543 C2 UA80543 C2 UA 80543C2
- Authority
- UA
- Ukraine
- Prior art keywords
- thiolate
- carried out
- venlafaxine
- alcohol
- reaction
- Prior art date
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 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 31
- 238000002360 preparation method Methods 0.000 title description 2
- -1 thiolate anion Chemical class 0.000 claims abstract description 18
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229960004688 venlafaxine Drugs 0.000 claims abstract description 16
- 230000001335 demethylating effect Effects 0.000 claims abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 150000004703 alkoxides Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 150000007944 thiolates Chemical class 0.000 claims description 5
- 230000017858 demethylation Effects 0.000 claims description 4
- 238000010520 demethylation reaction Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-M benzenethiolate Chemical compound [S-]C1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-M 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XRZRPHKMCVBSLA-UHFFFAOYSA-M sodium;dodecane-1-thiolate Chemical compound [Na+].CCCCCCCCCCCC[S-] XRZRPHKMCVBSLA-UHFFFAOYSA-M 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 150000004946 bicyclic arenes Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000004947 monocyclic arenes Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- 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
- A61P25/06—Antimigraine agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33495301P | 2001-12-04 | 2001-12-04 | |
| PCT/US2002/038403 WO2003048104A1 (fr) | 2001-12-04 | 2002-12-03 | Procedes de preparation de o-desmethyle venlafaxine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA80543C2 true UA80543C2 (en) | 2007-10-10 |
Family
ID=23309595
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040705306A UA80543C2 (en) | 2001-12-04 | 2002-03-12 | Method for the preparation of o-desmethylvenlafaxine |
Country Status (28)
| Country | Link |
|---|---|
| US (4) | US6689912B2 (fr) |
| EP (1) | EP1451143B9 (fr) |
| JP (1) | JP4342312B2 (fr) |
| KR (1) | KR100939650B1 (fr) |
| CN (1) | CN1319934C (fr) |
| AR (1) | AR037622A1 (fr) |
| AT (1) | ATE403641T1 (fr) |
| AU (1) | AU2002357049B2 (fr) |
| BR (1) | BR0214701A (fr) |
| CA (1) | CA2466779C (fr) |
| CO (1) | CO5580816A2 (fr) |
| DE (1) | DE60228118D1 (fr) |
| DK (1) | DK1451143T3 (fr) |
| EC (1) | ECSP045135A (fr) |
| ES (1) | ES2311647T4 (fr) |
| HU (1) | HUP0402269A3 (fr) |
| IL (3) | IL162253A0 (fr) |
| MX (1) | MXPA04005309A (fr) |
| NO (1) | NO20042680L (fr) |
| NZ (1) | NZ533316A (fr) |
| PL (1) | PL369299A1 (fr) |
| PT (1) | PT1451143E (fr) |
| RU (1) | RU2317286C2 (fr) |
| SI (1) | SI1451143T1 (fr) |
| TW (1) | TWI260982B (fr) |
| UA (1) | UA80543C2 (fr) |
| WO (1) | WO2003048104A1 (fr) |
| ZA (1) | ZA200405250B (fr) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6342533B1 (en) * | 1998-12-01 | 2002-01-29 | Sepracor, Inc. | Derivatives of (−)-venlafaxine and methods of preparing and using the same |
| HUP0200898A3 (en) * | 1999-04-06 | 2005-09-28 | Sepracor Inc | Derivatives of venlafaxine and methods of preparing and using the same |
| JP4220243B2 (ja) * | 2001-02-12 | 2009-02-04 | ワイス | O−デスメチル−ベンラファキシンの新規コハク酸塩 |
| UA80543C2 (en) * | 2001-12-04 | 2007-10-10 | Wyeth Corp | Method for the preparation of o-desmethylvenlafaxine |
| JP2009500420A (ja) * | 2005-07-06 | 2009-01-08 | セプラコア インコーポレーテッド | エスゾピクロン及びo−デスメチルベンラファキシンの組み合わせ、並びに閉経期並びに気分、不安、及び認知障害の治療方法 |
| EP1957470A1 (fr) * | 2005-12-05 | 2008-08-20 | Wyeth | Procede pour la synthese selective d'enantiomeres de 1-(2-amino-1-phenyl-ethyl)-cyclohexanols substitues |
| WO2007071404A1 (fr) * | 2005-12-20 | 2007-06-28 | Synthon B.V. | Procédé de fabrication de la desvenlafaxine |
| WO2007120923A1 (fr) | 2006-04-17 | 2007-10-25 | Teva Pharmaceutical Industries Ltd. | O-desméthylvenlafaxine essentiellement pure et ses procédés de préparation |
| MX2007016179A (es) * | 2006-04-17 | 2008-03-11 | Teva Pharma | Formas cristalinas de o-desmetilvenlafaxina. |
| WO2008035369A2 (fr) * | 2006-06-30 | 2008-03-27 | Alembic Limited | Nouvelle forme de o-desméthyl venlafaxine |
| US20090137846A1 (en) * | 2006-07-26 | 2009-05-28 | Valerie Niddam-Hildesheim | Processes for the synthesis of O-Desmethylvenlafaxine |
| WO2008013993A2 (fr) * | 2006-07-26 | 2008-01-31 | Teva Pharmaceutical Industries Ltd. | Procédés pour synthétiser le composé o-desméthylvenlafaxine |
| WO2008013995A2 (fr) * | 2006-07-26 | 2008-01-31 | Teva Pharmaceutical Industries Ltd. | Procédés pour synthétiser le composé o-desméthylvenlafaxine |
| CA2656167A1 (fr) | 2006-07-26 | 2008-01-31 | Teva Pharmaceutical Industries Ltd. | Procede pour synthetiser le compose o-desmethylvenlafaxine |
| US20090069601A1 (en) * | 2006-07-26 | 2009-03-12 | Valerie Niddam-Hildesheim | Processes for the synthesis of O-desmethylvenlafaxine |
| US20080221356A1 (en) * | 2006-07-26 | 2008-09-11 | Valerie Niddam-Hildesheim | Processes for the synthesis of O-desmethylvenlafaxine |
| EP1934168A2 (fr) * | 2006-07-26 | 2008-06-25 | Teva Pharmaceutical Industries Ltd | Tridesmethylvenlafaxine et procédés pour la préparation de desmethylvenlafaxine |
| WO2008015584A2 (fr) * | 2006-08-04 | 2008-02-07 | Medichem, S.A. | Procédé amélioré de synthèse d'une base libre de desvenlafaxine et de sels ou solvates de celle-ci |
| CA2672808A1 (fr) * | 2007-01-31 | 2008-08-07 | Generics [Uk] Limited | Procede de preparation de o-desmethyl venlafaxine |
| EP2049465A2 (fr) * | 2007-03-14 | 2009-04-22 | Teva Pharmaceutical Industries Ltd. | Procédés pour préparer des états solides de succinate d'o-desméthylvenlafaxine |
| TR200909798T1 (tr) * | 2007-07-12 | 2010-05-21 | Dr. Reddy's Laboratories Ltd. | O-desmetilvenlafaksin. |
| WO2009010990A2 (fr) * | 2007-07-16 | 2009-01-22 | Matrix Laboratories Limited | Procédé pour préparer des formes polymorphes de succinate de o-desméthylvenlafaxine |
| WO2009034434A2 (fr) * | 2007-09-10 | 2009-03-19 | Cadila Pharmaceuticals Limited | Procédé amélioré pour la préparation de o-desméthylvenlafaxine |
| US20110118357A1 (en) * | 2007-10-26 | 2011-05-19 | Generics Limited | Process for preparing o-desmethylvenlafaxine |
| EP2217562A2 (fr) * | 2007-11-26 | 2010-08-18 | Teva Pharmaceutical Industries Ltd. | Formes cristallines de fumarate de o-desméthylvenlafaxine |
| WO2009084038A2 (fr) * | 2007-12-28 | 2009-07-09 | Ind-Swift Laboratories Limited | Procédé amélioré d'élaboration d'o-desméthyl venlafaxine |
| CA2717580A1 (fr) * | 2008-03-06 | 2009-12-17 | Teva Pharmaceutical Industries Ltd. | Procedes de preparation de la o-desmethylvenlafaxine, exempte de ses impuretes dimeres |
| EP2119696A1 (fr) | 2008-05-16 | 2009-11-18 | Krka | Préparation de sels de O-desméthylvenlafaxine |
| EP2119695A1 (fr) | 2008-05-16 | 2009-11-18 | Krka | Préparation de sels de O-desméthylvenlafaxine |
| EP2297087A2 (fr) * | 2008-06-16 | 2011-03-23 | Teva Pharmaceutical Industries Ltd. | États solides de sels de o-desméthylvenlafaxine |
| US20100016638A1 (en) * | 2008-07-21 | 2010-01-21 | Zdenko Hamersak | Method for preparation of o-desmethylvenlafaxine using polythiolates |
| CA2731165A1 (fr) * | 2008-07-30 | 2010-02-04 | Generics (Uk) Limited | Procede pour l'elaboration d'o-desmethylvenlafaxine |
| CZ301503B6 (cs) | 2008-11-27 | 2010-03-24 | Zentiva, A. S. | Zpusob prípravy desvenlafaxinu a jeho solí |
| CZ200969A3 (cs) | 2009-02-06 | 2010-06-30 | Zentiva, K.S. | Nové soli desvenlafaxinu a zpusob jejich prípravy |
| CZ302145B6 (cs) | 2009-07-15 | 2010-11-10 | Zentiva, K. S. | Zpusob prípravy desvenlafaxinu a jeho solí |
| AU2010272377A1 (en) | 2009-07-16 | 2012-01-19 | Cipla Limited | Process for the preparation of O-desmethyl venlafaxine and intermediate for use therein |
| US20110098506A1 (en) * | 2009-10-26 | 2011-04-28 | Intas Pharmaceuticals Limited | Method of preparing o-desmethylvenlafaxine |
| US20110184067A1 (en) * | 2010-01-25 | 2011-07-28 | Intas Pharmaceuticals Ltd. | O-desmethylvenlafaxine succinate polymorph & process for preparing thereof |
| EP2539313A2 (fr) | 2010-03-29 | 2013-01-02 | Pliva Hrvatska D.O.O. | Formes cristallines du fumarate de o-desméthylvenlafaxine |
| 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 (fr) | 2010-06-11 | 2011-12-14 | LEK Pharmaceuticals d.d. | Procédé pour déméthyler des éthers méthyliques aromatiques à l'aide d'acide mercaptopropionique |
| ES2961706T3 (es) | 2017-02-09 | 2024-03-13 | R L Finechem Private Ltd | Un proceso para la preparación de 1-[2-(dimetilamino)-1-(4-hidroxifenil)etil]-ciclohexanol y sales del mismo |
| CN109232189B (zh) * | 2018-09-25 | 2021-10-08 | 杭州盛弗泰新材料科技有限公司 | 一种高纯度1-羟基芘的制备方法 |
| 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 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2741009A1 (de) * | 1976-09-22 | 1978-03-23 | Sandoz Ag | 4-styryl-4-indolinol-derivate, ihre verwendung und herstellung |
| US4535186A (en) | 1983-04-19 | 1985-08-13 | American Home Products Corporation | 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives |
| CA1227304A (fr) * | 1984-08-01 | 1987-09-29 | Raymond C. Francis | Defibrage de la pate a papier |
| GB8902209D0 (en) | 1989-02-01 | 1989-03-22 | Wyeth John And Brother Limited | Preparation of cyclohexanol derivatives and novel thioamide intermediates |
| US6197828B1 (en) * | 1998-12-01 | 2001-03-06 | Sepracor, Inc. | Derivatives of (+)-venlafaxine and methods of preparing and using the same |
| US6342533B1 (en) * | 1998-12-01 | 2002-01-29 | Sepracor, Inc. | Derivatives of (−)-venlafaxine and methods of preparing and using the same |
| HUP0200898A3 (en) | 1999-04-06 | 2005-09-28 | Sepracor Inc | Derivatives of venlafaxine and methods of preparing and using the same |
| WO2000076955A1 (fr) | 1999-06-15 | 2000-12-21 | American Home Products Corporation | Enantiomeres de o-desmethyl venlafaxine |
| WO2002006453A2 (fr) | 2000-07-18 | 2002-01-24 | Bayer Aktiengesellschaft | Regulation de protease a serine humaine de type desc1 |
| JP4220243B2 (ja) * | 2001-02-12 | 2009-02-04 | ワイス | O−デスメチル−ベンラファキシンの新規コハク酸塩 |
| UA80543C2 (en) * | 2001-12-04 | 2007-10-10 | Wyeth Corp | Method for the preparation of o-desmethylvenlafaxine |
-
2002
- 2002-03-12 UA UA20040705306A patent/UA80543C2/uk unknown
- 2002-11-26 US US10/304,871 patent/US6689912B2/en not_active Expired - Fee Related
- 2002-11-27 TW TW091134427A patent/TWI260982B/zh not_active IP Right Cessation
- 2002-12-03 JP JP2003549297A patent/JP4342312B2/ja not_active Expired - Fee Related
- 2002-12-03 RU RU2004120284/04A patent/RU2317286C2/ru not_active IP Right Cessation
- 2002-12-03 PL PL02369299A patent/PL369299A1/xx unknown
- 2002-12-03 AR ARP020104669A patent/AR037622A1/es unknown
- 2002-12-03 CA CA2466779A patent/CA2466779C/fr not_active Expired - Lifetime
- 2002-12-03 EP EP02804479A patent/EP1451143B9/fr not_active Expired - Lifetime
- 2002-12-03 MX MXPA04005309A patent/MXPA04005309A/es active IP Right Grant
- 2002-12-03 AU AU2002357049A patent/AU2002357049B2/en not_active Ceased
- 2002-12-03 ES ES02804479T patent/ES2311647T4/es not_active Expired - Lifetime
- 2002-12-03 CN CNB028242386A patent/CN1319934C/zh not_active Expired - Fee Related
- 2002-12-03 PT PT02804479T patent/PT1451143E/pt unknown
- 2002-12-03 DK DK02804479T patent/DK1451143T3/da active
- 2002-12-03 BR BR0214701-7A patent/BR0214701A/pt not_active Application Discontinuation
- 2002-12-03 SI SI200230743T patent/SI1451143T1/sl unknown
- 2002-12-03 NZ NZ533316A patent/NZ533316A/en unknown
- 2002-12-03 DE DE60228118T patent/DE60228118D1/de not_active Expired - Lifetime
- 2002-12-03 IL IL16225302A patent/IL162253A0/xx active IP Right Grant
- 2002-12-03 WO PCT/US2002/038403 patent/WO2003048104A1/fr not_active Ceased
- 2002-12-03 AT AT02804479T patent/ATE403641T1/de not_active IP Right Cessation
- 2002-12-03 HU HU0402269A patent/HUP0402269A3/hu active IP Right Revival
- 2002-12-03 KR KR1020047008512A patent/KR100939650B1/ko not_active Expired - Fee Related
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2003
- 2003-12-31 US US10/750,196 patent/US20040158101A1/en not_active Abandoned
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2004
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- 2004-06-01 CO CO04050957A patent/CO5580816A2/es active IP Right Grant
- 2004-06-04 EC EC2004005135A patent/ECSP045135A/es unknown
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2007
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2008
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- 2008-09-11 US US12/208,990 patent/US20090018365A1/en not_active Abandoned
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