AR039857A1 - Preparaciones de una sulfinilacetamida - Google Patents
Preparaciones de una sulfinilacetamidaInfo
- Publication number
- AR039857A1 AR039857A1 ARP030101796A ARP030101796A AR039857A1 AR 039857 A1 AR039857 A1 AR 039857A1 AR P030101796 A ARP030101796 A AR P030101796A AR P030101796 A ARP030101796 A AR P030101796A AR 039857 A1 AR039857 A1 AR 039857A1
- Authority
- AR
- Argentina
- Prior art keywords
- approximately
- equivalents
- reaction
- aqueous solution
- benzhydrylthiol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 2
- CFVMQQXRNGNVFQ-UHFFFAOYSA-N 2-sulfinylacetamide Chemical compound NC(=O)C=S=O CFVMQQXRNGNVFQ-UHFFFAOYSA-N 0.000 title 1
- 239000007864 aqueous solution Substances 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 abstract 5
- 229960001165 modafinil Drugs 0.000 abstract 5
- HCRQRIFRHGPWBH-UHFFFAOYSA-N 2-benzhydrylsulfanylacetamide Chemical compound C=1C=CC=CC=1C(SCC(=O)N)C1=CC=CC=C1 HCRQRIFRHGPWBH-UHFFFAOYSA-N 0.000 abstract 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 4
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 2
- FBPZCNQOMKJFRD-UHFFFAOYSA-N benzhydryl carbamimidothioate Chemical class C=1C=CC=CC=1C(SC(=N)N)C1=CC=CC=C1 FBPZCNQOMKJFRD-UHFFFAOYSA-N 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- HVWYTOBXSCCZOP-UHFFFAOYSA-N 3,3-diphenylpropanethioamide Chemical compound C=1C=CC=CC=1C(CC(=S)N)C1=CC=CC=C1 HVWYTOBXSCCZOP-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Proporciona procedimientos para la preparación de modafinilo, que incluye la etapa de la reacción de benzhidriltiol y cloroacetamida, para obtener la correspondiente benzhidriltioacetamida. Reivindicación 18: Un procedimiento para preparar modafinilo consistente en: (1) la reacción de benzhidrol, tiourea (aproximadamente 1-3 equivalentes) y una solución acuosa de HBr al 48% (aproximadamente 1-3 equivalentes) en tetrahidrofurano acuoso a aproximadamente 70sC para formar sal de S-benzhidriltiouronio; (2) la reacción de la sal de S-benzhidriltiouronio con una solución acuosa de hidróxido de potasio (aproximadamente 2-5 equivalentes) a aproximadamente 70sC para formar benzhidriltiol; (3) la reacción de cloroacetamida (aproximadamente 1,05-2 equivalentes) en una solución acuosa de tetrahidrofurano con el benzhidriltiol a aproximadamente 70sC para formar 2-(benzhidriltiil)acetamida; y (4) la reacción de la 2-(benzhidriltiil)acetamida con ácido acético (aproximadamente 2-5 equivalentes) y una solución acuosa al 30% de peróxido de hidrógeno (aproximadamente 1,2-2 equivalentes) para formar modafinilo. Reivindicación 19: Un procedimiento de preparación de modafinilo consistente en: (1) la reacción de benzhidrol, tiourea (aproximadamente 1-3 equivalentes) y una solución acuosa de HBr al 48% (aproximadamente 1-3 equivalentes) en clorobenceno acuoso a aproximadamente 70sC para formar sal de S-benzhidriltiouronio; (2) la reacción de la sal de S-benzhidriltiouronio con una solución acuosa de hidróxido de potasio (aproximadamente 2-5 equivalentes) a aproximadamente 70sC para formar benzhidriltiol; (3) la reacción de cloroacetamida (aproximadamente 1,05-2 equivalentes) en forma de polvo con el benzhidriltiol a aproximadamente 70sC para formar 2-(benzhidriltiil)acetamida; y (4) la reacción de la 2-(benzhidriltiil)acetamida con ácido acético (aproximadamente 2-5 equivalentes) y una solución acuosa al 30% de peróxido de hidrógeno (aproximadamente 1,2-2 equivalentes) para formar modafinilo.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38317302P | 2002-05-23 | 2002-05-23 | |
| US10/443,327 US6875893B2 (en) | 2002-05-23 | 2003-05-22 | Preparations of a sulfinyl acetamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR039857A1 true AR039857A1 (es) | 2005-03-02 |
Family
ID=29586987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP030101796A AR039857A1 (es) | 2002-05-23 | 2003-05-23 | Preparaciones de una sulfinilacetamida |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US6875893B2 (es) |
| EP (1) | EP1506171B1 (es) |
| JP (1) | JP4351627B2 (es) |
| KR (1) | KR100984571B1 (es) |
| CN (1) | CN100379721C (es) |
| AR (1) | AR039857A1 (es) |
| AT (1) | ATE414058T1 (es) |
| BR (1) | BR0311242A (es) |
| CA (1) | CA2486533C (es) |
| CY (1) | CY1108747T1 (es) |
| DE (1) | DE60324671D1 (es) |
| DK (1) | DK1506171T3 (es) |
| EA (1) | EA007561B1 (es) |
| EG (1) | EG23693A (es) |
| ES (1) | ES2316755T3 (es) |
| HK (1) | HK1072596A1 (es) |
| IL (2) | IL165095A0 (es) |
| IS (1) | IS2650B (es) |
| MX (1) | MXPA04011459A (es) |
| MY (1) | MY129141A (es) |
| NO (1) | NO329559B1 (es) |
| NZ (1) | NZ536747A (es) |
| PL (1) | PL211695B1 (es) |
| PT (1) | PT1506171E (es) |
| SI (1) | SI1506171T1 (es) |
| TW (1) | TWI317733B (es) |
| UA (1) | UA79790C2 (es) |
| WO (1) | WO2003099774A1 (es) |
| ZA (1) | ZA200409400B (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1787980T3 (da) | 2000-07-27 | 2010-04-26 | Teva Pharma | Krystallint og rent modafinil og fremgangsmåde til atfremstille dette |
| US6875893B2 (en) * | 2002-05-23 | 2005-04-05 | Cephalon, Inc. | Preparations of a sulfinyl acetamide |
| US6992219B2 (en) * | 2002-08-09 | 2006-01-31 | Cephalon France | Modafinil polymorphic forms |
| FR2849029B1 (fr) * | 2002-12-20 | 2005-03-18 | Lafon Labor | Procede de preparation et formes cristallines des enantiomeres optiques du modafinil. |
| MXPA05008088A (es) * | 2003-02-24 | 2005-09-21 | Mallinckrodt Inc | Proceso mejorado para preparar benzhidril tioacetamida. |
| US20040253308A1 (en) * | 2003-04-29 | 2004-12-16 | Barr Laboratories, Inc. | Surface-treated modafinil particles |
| US7368591B2 (en) | 2003-09-19 | 2008-05-06 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| ATE410410T1 (de) * | 2003-10-23 | 2008-10-15 | Mallinckrodt Inc | Verbessertes verfahren zur herstellung von benzhydrylthioacetamid. |
| US20060086667A1 (en) * | 2004-09-13 | 2006-04-27 | Cephalon, Inc., U.S. Corporation | Methods for the separation of enantiomeric sulfinylacetamides |
| EP1737889B1 (en) | 2004-10-19 | 2010-09-08 | Lonza AG | Method for solid phase peptide synthesis |
| EP1909573A4 (en) * | 2005-07-21 | 2010-09-22 | Neurohealing Pharmaceuticals I | SHORT-TERM EFFECTIVE MODAFINIL COMPOSITIONS WITH A RAPID INITIAL EFFECT, AND METHOD FOR THEIR USE |
| US7553646B2 (en) * | 2005-07-28 | 2009-06-30 | University Of Iowa Research Foundation | Microbial sulfoxidation and amidation of benzhdrylsulfanyl carboxylic acids and uses thereof |
| MX2008003552A (es) * | 2005-09-14 | 2008-11-12 | Novetide Ltd | Proceso para la produccion de bivalirudina. |
| CA2632722A1 (en) * | 2005-12-09 | 2007-06-21 | Mallinckrodt Inc. | Processes for the preparation of modafinil and analogs thereof |
| CN100343228C (zh) * | 2006-02-17 | 2007-10-17 | 中国科学院上海有机化学研究所 | 高对映体选择性制备 2－二苯甲基亚磺酰基－乙酰胺单一对映体的方法 |
| EP1986994A2 (en) * | 2006-02-21 | 2008-11-05 | Teva Pharmaceutical Industries Ltd | Novel crystalline forms of armodafinil and preparation thereof |
| EP2159219A3 (en) * | 2006-03-01 | 2010-12-15 | Teva Pharmaceutical Industries Ltd. | An improved process for the preparation of armodafinil |
| GB0604233D0 (en) * | 2006-03-02 | 2006-04-12 | Syngenta Participations Ag | Process |
| TW200820992A (en) * | 2006-07-12 | 2008-05-16 | Elan Corp Plc | Nanoparticulate formulations of modafinil |
| CA2660565C (en) * | 2006-08-14 | 2012-10-09 | Neurohealing Pharmaceuticals, Inc. | Modafinil-based treatment for premature ejaculation |
| WO2009025791A2 (en) * | 2007-08-16 | 2009-02-26 | Teva Pharmaceutical Industries Ltd. | Purification of armodafinil |
| US20100036164A1 (en) * | 2008-08-06 | 2010-02-11 | Srinivas Areveli | Preparation of armodafinil form i |
| CN102976985A (zh) * | 2011-09-07 | 2013-03-20 | 大连大学 | 一锅法合成二苯甲基亚磺酰基乙酰胺及其类似物的方法 |
| JP2017505266A (ja) * | 2014-02-06 | 2017-02-16 | ビレルドコールスネス アクティエボラーグ | 伸張可能な紙のスタンドアップポーチ |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1520812A (en) * | 1975-10-02 | 1978-08-09 | Lafon Labor | Benzhydrylsulphinyl derivatives |
| GB1584462A (en) * | 1977-03-31 | 1981-02-11 | Lafon Labor | N-diaryl-malonamide and diarylmethyl-sulphinyl-acetamide derivatives and pharmaceutical compositions containing them |
| FR2593809B1 (fr) * | 1986-01-31 | 1988-07-22 | Lafon Labor | Benzhydrylsulfinylacetamide, procede de preparation et utilisation en therapeutique |
| CA2416384A1 (en) | 2000-07-17 | 2003-01-16 | Takeda Chemical Industries, Ltd. | Sulfone derivatives, their production and use |
| DK1787980T3 (da) | 2000-07-27 | 2010-04-26 | Teva Pharma | Krystallint og rent modafinil og fremgangsmåde til atfremstille dette |
| IL143106A (en) * | 2001-05-13 | 2005-11-20 | Chemagis Ltd | Process for the preparation of diphenylmethylthioacetamide |
| US6875893B2 (en) * | 2002-05-23 | 2005-04-05 | Cephalon, Inc. | Preparations of a sulfinyl acetamide |
| DE10245546B3 (de) * | 2002-09-30 | 2004-05-13 | Infineon Technologies Ag | Pseudostatische Speicherschaltung |
| JP3838972B2 (ja) * | 2002-12-25 | 2006-10-25 | Ｎｅｃエレクトロニクス株式会社 | 周波数検出回路及びデータ処理装置 |
-
2003
- 2003-05-22 US US10/443,327 patent/US6875893B2/en not_active Expired - Lifetime
- 2003-05-23 AT AT03729108T patent/ATE414058T1/de active
- 2003-05-23 DK DK03729108T patent/DK1506171T3/da active
- 2003-05-23 EP EP03729108A patent/EP1506171B1/en not_active Expired - Lifetime
- 2003-05-23 PL PL373792A patent/PL211695B1/pl unknown
- 2003-05-23 US US11/091,215 patent/US7057069B2/en not_active Expired - Fee Related
- 2003-05-23 CA CA2486533A patent/CA2486533C/en not_active Expired - Fee Related
- 2003-05-23 PT PT03729108T patent/PT1506171E/pt unknown
- 2003-05-23 NZ NZ536747A patent/NZ536747A/en not_active IP Right Cessation
- 2003-05-23 DE DE60324671T patent/DE60324671D1/de not_active Expired - Lifetime
- 2003-05-23 IL IL16509503A patent/IL165095A0/xx unknown
- 2003-05-23 MX MXPA04011459A patent/MXPA04011459A/es active IP Right Grant
- 2003-05-23 EA EA200401551A patent/EA007561B1/ru not_active IP Right Cessation
- 2003-05-23 MY MYPI20031924A patent/MY129141A/en unknown
- 2003-05-23 KR KR1020047018819A patent/KR100984571B1/ko not_active IP Right Cessation
- 2003-05-23 BR BR0311242-0A patent/BR0311242A/pt not_active Application Discontinuation
- 2003-05-23 UA UA20041210602A patent/UA79790C2/uk unknown
- 2003-05-23 WO PCT/US2003/016379 patent/WO2003099774A1/en active Application Filing
- 2003-05-23 CN CNB038118386A patent/CN100379721C/zh not_active Expired - Fee Related
- 2003-05-23 JP JP2004507432A patent/JP4351627B2/ja not_active Expired - Lifetime
- 2003-05-23 ES ES03729108T patent/ES2316755T3/es not_active Expired - Lifetime
- 2003-05-23 TW TW092113924A patent/TWI317733B/zh not_active IP Right Cessation
- 2003-05-23 SI SI200331442T patent/SI1506171T1/sl unknown
- 2003-05-23 AR ARP030101796A patent/AR039857A1/es not_active Application Discontinuation
-
2004
- 2004-11-08 IL IL165095A patent/IL165095A/en active IP Right Grant
- 2004-11-09 IS IS7523A patent/IS2650B/is unknown
- 2004-11-11 NO NO20044916A patent/NO329559B1/no not_active IP Right Cessation
- 2004-11-21 EG EGNA2004000127 patent/EG23693A/xx active
- 2004-11-22 ZA ZA2004/09400A patent/ZA200409400B/en unknown
-
2005
- 2005-06-29 HK HK05105443.7A patent/HK1072596A1/xx not_active IP Right Cessation
-
2009
- 2009-02-04 CY CY20091100129T patent/CY1108747T1/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC | Refusal |