PE25698A1 - PROCEDURES AND INTERMEDIATES TO PREPARE 1-BENCIL-4 - ((5,6-DIMETOXI-1-INDANON) -2-IL) METHYLPIPERIDINE - Google Patents
PROCEDURES AND INTERMEDIATES TO PREPARE 1-BENCIL-4 - ((5,6-DIMETOXI-1-INDANON) -2-IL) METHYLPIPERIDINEInfo
- Publication number
- PE25698A1 PE25698A1 PE1996000883A PE00088396A PE25698A1 PE 25698 A1 PE25698 A1 PE 25698A1 PE 1996000883 A PE1996000883 A PE 1996000883A PE 00088396 A PE00088396 A PE 00088396A PE 25698 A1 PE25698 A1 PE 25698A1
- Authority
- PE
- Peru
- Prior art keywords
- compound
- react
- iii
- alkyl
- bencil
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- -1 BENZYL HALIDE Chemical class 0.000 abstract 1
- 206010039966 Senile dementia Diseases 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 210000004556 brain Anatomy 0.000 abstract 1
- 208000026106 cerebrovascular disease Diseases 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000544 cholinesterase inhibitor Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
SE REFIEREN A LOS COMPUESTOS INTERMEDIOS DE FORMULAS (I), (II) Y (III), EN DONDE: R1 ES R2O(CO) o R3(CO); R2 ES ALQUILO C1-C4; R3 ES ALQUILO C1-C4 O FENILO CON OPCIONALMENTE 1; 2 o 3 SUSTITUYENTES ALQUILO C1-C4, ALCOXI C1-C4, HALO o CF3. TAMBIEN SE REFIEREN A LOS PROCEDIMIENTOS DE PREPARACION QUE COMPRENDE: 1) HACER REACCIONAR UN COMPUESTO (IV) CON (V) EN PRESENCIA DE AlCl3 Y CLORURO DE METILENO, PARA FORMAR (III); 2) HACER REACCIONAR (III) CON UN AGENTE DE METENILACION, PARA FORMAR (II); 3) HACER REACCIONAR (II) CON H2SO4; 3) AISLAR MEDIANTE LA ADICION DE SOLUCION FUERTEMENTE ACIDA A HIELO/AGUA, SEGUIDA POR EXTRACCION CON UN DISOLVENTE ORGANICO Y ELIMINACION DEL DISOLVENTE ORGANICO ANTES DE QUE SE TRATE CON UNA BASE; 4) HACER REACCIONAR (I) CON HIDROXIDO, PARA FORMAR (VI) EN DONDE: (VI) ES EL COMPUESTO (I) EN EL QUE R1 ES H, Y HACER REACCIONAR DICHO COMPUESTO CON UN HALURO DE BENCILO, PARA FORMAR UN COMPUESTO FINAL ANTICOLINESTERASA DE FORMULA (VII), EN DONDE: (VII) ES (I) EN EL QUE R1 ES BENCILO. EL COMPUESTO OBTENIDO ES USADO PARA EL TRATAMIENTO DE LA DEMENCIA SENIL, PARTICULARMENTE DEL TIPO ALZHEIMER Y DE LA ENFERMEDAD CEREBROVASCULAR QUE ACOMPANA A LA APOPLEJIA CEREBRALTHEY REFER TO THE INTERMEDIATE COMPOUNDS OF FORMULAS (I), (II) AND (III), WHERE: R1 IS R2O (CO) or R3 (CO); R2 IS C1-C4 ALKYL; R3 IS C1-C4 ALKYL OR PHENYL WITH OPTIONALLY 1; 2 or 3 ALKYL SUBSTITUTES C1-C4, ALCOXI C1-C4, HALO or CF3. THEY ALSO REFER TO THE PREPARATION PROCEDURES THAT INCLUDE: 1) REACTING A COMPOUND (IV) WITH (V) IN THE PRESENCE OF AlCl3 AND METHYLENE CHLORIDE, TO FORM (III); 2) MAKE REACT (III) WITH A METHENILATION AGENT, TO FORM (II); 3) REACT (II) WITH H2SO4; 3) ISOLATE THROUGH ADDITION OF SOLUTION STRONGLY ACIDED TO ICE / WATER, FOLLOWED BY EXTRACTION WITH AN ORGANIC SOLVENT AND DISPOSAL OF THE ORGANIC SOLVENT BEFORE IT IS TREATED WITH A BASE; 4) REACT (I) WITH HYDROXIDE, TO FORM (VI) WHERE: (VI) IS THE COMPOUND (I) IN WHICH R1 IS H, AND REACT THIS COMPOUND WITH A BENZYL HALIDE, TO FORM A FINAL COMPOUND ANTICHOLINESTERASE OF FORMULA (VII), WHERE: (VII) IS (I) IN WHICH R1 IS BENCIL. THE COMPOUND OBTAINED IS USED FOR THE TREATMENT OF SENILE DEMENTIA, PARTICULARLY OF THE ALZHEIMER TYPE AND CEREBROVASCULAR DISEASE ACCOMPANYING BRAIN APOPLEJIA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US875395P | 1995-12-15 | 1995-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE25698A1 true PE25698A1 (en) | 1998-05-21 |
Family
ID=21733469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE1996000883A PE25698A1 (en) | 1995-12-15 | 1996-12-09 | PROCEDURES AND INTERMEDIATES TO PREPARE 1-BENCIL-4 - ((5,6-DIMETOXI-1-INDANON) -2-IL) METHYLPIPERIDINE |
Country Status (33)
| Country | Link |
|---|---|
| EP (1) | EP0883607A1 (en) |
| JP (1) | JP3066083B2 (en) |
| KR (1) | KR20000064387A (en) |
| AP (1) | AP708A (en) |
| AR (1) | AR004368A1 (en) |
| AU (1) | AU716462B2 (en) |
| BG (1) | BG102525A (en) |
| BR (1) | BR9612018A (en) |
| CA (1) | CA2237647A1 (en) |
| CO (1) | CO4750831A1 (en) |
| CZ (1) | CZ180898A3 (en) |
| DZ (1) | DZ2141A1 (en) |
| GT (1) | GT199600092A (en) |
| HN (1) | HN1996000065A (en) |
| HR (1) | HRP960592A2 (en) |
| HU (1) | HUP9904275A3 (en) |
| IL (3) | IL136420A0 (en) |
| IS (1) | IS4752A (en) |
| MA (1) | MA24032A1 (en) |
| NO (1) | NO982712D0 (en) |
| NZ (1) | NZ318843A (en) |
| OA (1) | OA10694A (en) |
| PE (1) | PE25698A1 (en) |
| PL (1) | PL197306B1 (en) |
| RO (1) | RO121382B1 (en) |
| RU (1) | RU2160731C2 (en) |
| SK (1) | SK75498A3 (en) |
| TN (1) | TNSN96153A1 (en) |
| TW (1) | TW414787B (en) |
| UY (1) | UY24401A1 (en) |
| WO (1) | WO1997022584A1 (en) |
| YU (1) | YU49486B (en) |
| ZA (1) | ZA9610533B (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2237078T3 (en) | 1998-01-16 | 2005-07-16 | Eisai Co., Ltd. | PROCEDURE TO PRODUCE DERIVATIVES OF DONEPEZILO. |
| IL125809A (en) * | 1998-08-17 | 2005-08-31 | Finetech Lab Ltd | Process and intermediates for production of donepezil and related compounds |
| US7148354B2 (en) * | 2002-07-24 | 2006-12-12 | Dr. Reddy's Laboratories Limited | Process for preparation of donepezil |
| IL150982A (en) | 2002-07-30 | 2007-02-11 | Ori Lerman | Process for the preparation of donepezil |
| IL151253A0 (en) * | 2002-08-14 | 2003-04-10 | Finetech Lab Ltd | Process for production of highly pure donepezil hydrochloride |
| US6649765B1 (en) | 2003-02-12 | 2003-11-18 | Usv Limited, Bsd Marg. | Process for the preparation of 1-benzyl-4(5,6-dimethoxy-1-indanon)-2-yl) methyl piperidine hydrochloride (Donepezil HCL) |
| US6953856B2 (en) | 2003-02-12 | 2005-10-11 | Usv, Limited | Process for the preparation of 1-benzyl-4-(5,6-dimethoxy-1-indanon)-2-yl) methyl piperidine hydrochloride (Donepezil HCI) |
| US20070129549A1 (en) * | 2003-03-21 | 2007-06-07 | Yatendra Kumar | Stable lamotrigine pharmaceutical compositions and processes for their preparation |
| WO2004099142A1 (en) * | 2003-05-05 | 2004-11-18 | Ranbaxy Laboratories Limited | Hydrobromide salt of benzyl-piperidylmethyl-indanone and its polymorphs |
| EP1654230A1 (en) | 2003-07-01 | 2006-05-10 | Hetero Drugs Limited | Preparation of intermediates for acetyl cholinesterase inhibitors |
| CN1280273C (en) | 2003-11-05 | 2006-10-18 | 天津和美生物技术有限公司 | Synthesis of donepizin and its derivative |
| US7592459B2 (en) | 2004-09-29 | 2009-09-22 | Chemagis Ltd. | Use of purified donepezil maleate for preparing pharmaceutically pure amorphous donepezil hydrochloride |
| CN100436416C (en) * | 2005-07-29 | 2008-11-26 | 西南合成制药股份有限公司 | Novel donepezil synthesis process |
| GB0515803D0 (en) * | 2005-07-30 | 2005-09-07 | Pliva Hrvatska D O O | Intermediate compounds |
| AR057910A1 (en) | 2005-11-18 | 2007-12-26 | Synthon Bv | PROCESS TO PREPARE DONEPEZILO |
| CA2635550A1 (en) * | 2006-01-04 | 2007-07-12 | Cipla Limited | Process and intermediate for preparation of donepezil |
| EP2114166A4 (en) * | 2006-12-11 | 2011-05-25 | Reviva Pharmaceuticals Inc | Compositions, synthesis, and methods of using indanone based cholinesterase inhibitors |
| WO2013078608A1 (en) | 2011-11-29 | 2013-06-06 | Ziqiang Gu | Donepezil pamoate and methods of making and using the same |
| TW201540301A (en) | 2013-08-16 | 2015-11-01 | Takeda Gmbh | Treatment of cognitive impairment with PDE4 inhibitor |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI95572C (en) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Process for the preparation of a medicament useful as a piperidine derivative or its pharmaceutical salt |
| FR2642069B1 (en) * | 1989-01-20 | 1991-04-12 | Rhone Poulenc Sante | NOVEL BENZOPYRAN DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| DE4439822A1 (en) * | 1994-11-08 | 1996-08-29 | Bayer Ag | Process for the preparation of benzyl-piperidylmethyl-indanones |
-
1996
- 1996-10-11 CZ CZ981808A patent/CZ180898A3/en unknown
- 1996-10-11 CA CA002237647A patent/CA2237647A1/en not_active Abandoned
- 1996-10-11 JP JP9522607A patent/JP3066083B2/en not_active Expired - Lifetime
- 1996-10-11 AU AU70925/96A patent/AU716462B2/en not_active Ceased
- 1996-10-11 WO PCT/IB1996/001076 patent/WO1997022584A1/en not_active Ceased
- 1996-10-11 HU HU9904275A patent/HUP9904275A3/en unknown
- 1996-10-11 IL IL13642096A patent/IL136420A0/en unknown
- 1996-10-11 PL PL327512A patent/PL197306B1/en not_active IP Right Cessation
- 1996-10-11 RU RU98111204/04A patent/RU2160731C2/en not_active IP Right Cessation
- 1996-10-11 EP EP96931937A patent/EP0883607A1/en not_active Withdrawn
- 1996-10-11 RO RO98-01070A patent/RO121382B1/en unknown
- 1996-10-11 BR BR9612018A patent/BR9612018A/en not_active Application Discontinuation
- 1996-10-11 KR KR1019980704423A patent/KR20000064387A/en not_active Ceased
- 1996-10-11 IL IL12445296A patent/IL124452A0/en unknown
- 1996-10-11 SK SK754-98A patent/SK75498A3/en unknown
- 1996-10-11 NZ NZ318843A patent/NZ318843A/en unknown
- 1996-10-11 IL IL13642196A patent/IL136421A0/en unknown
- 1996-10-14 TW TW085112515A patent/TW414787B/en not_active IP Right Cessation
- 1996-10-15 HN HN1996000065A patent/HN1996000065A/en unknown
- 1996-11-18 GT GT199600092A patent/GT199600092A/en unknown
- 1996-12-09 PE PE1996000883A patent/PE25698A1/en not_active Application Discontinuation
- 1996-12-10 AR ARP960105577A patent/AR004368A1/en unknown
- 1996-12-11 TN TNTNSN96153A patent/TNSN96153A1/en unknown
- 1996-12-11 MA MA24424A patent/MA24032A1/en unknown
- 1996-12-11 YU YU66096A patent/YU49486B/en unknown
- 1996-12-11 DZ DZ960186A patent/DZ2141A1/en active
- 1996-12-12 UY UY24401A patent/UY24401A1/en not_active IP Right Cessation
- 1996-12-12 CO CO96065334A patent/CO4750831A1/en unknown
- 1996-12-12 AP APAP/P/1996/000892A patent/AP708A/en active
- 1996-12-13 ZA ZA9610533A patent/ZA9610533B/en unknown
- 1996-12-13 HR HR60/008,753A patent/HRP960592A2/en not_active Application Discontinuation
-
1998
- 1998-05-22 IS IS4752A patent/IS4752A/en unknown
- 1998-06-05 OA OA9800076A patent/OA10694A/en unknown
- 1998-06-09 BG BG102525A patent/BG102525A/en unknown
- 1998-06-12 NO NO982712A patent/NO982712D0/en not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration | ||
| FD | Application declared void or lapsed |