AR021901A1 - Un procedimiento para preparar 3-alcanoilindoles y 3-alquilindoles. - Google Patents
Un procedimiento para preparar 3-alcanoilindoles y 3-alquilindoles.Info
- Publication number
- AR021901A1 AR021901A1 ARP990106531A ARP990106531A AR021901A1 AR 021901 A1 AR021901 A1 AR 021901A1 AR P990106531 A ARP990106531 A AR P990106531A AR P990106531 A ARP990106531 A AR P990106531A AR 021901 A1 AR021901 A1 AR 021901A1
- Authority
- AR
- Argentina
- Prior art keywords
- hal
- formula
- aryl
- atoms
- independently represent
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Un procedimiento para preparar 3-alcaloilindoles y 3-alquilindoles de formula (1) donde R representa Hal o metilo, R1 y R2 representan independientementeH, A, arilo, NH2, NHA, N(A)2, COOA, CN o Hal, X representa O o H,H, A,A,A representanindependien temente alquilo de 1 a 6 átomos de C, Hal representa F, Cl, Br o I y n es 1, 2, 3, 4, 5, o 6, y las sales de estos compuestos formadas por adicion de ácido, procedimiento en el cual a) cuando X representa O yR, R1, R2 y n tienen lossignificados indicados, se hace reaccionar un compuesto de formula (2), en donde R1, R2 representan independientemente H, A, arilo,NH2, NHA, N (A)2, COOA, CN o Hal, AAA representan independientemente alquilo de 1 a 6 átomos de C y Hal representa F,Cl, Br o I, con un compuestode formula R-(CH2)n-CO-L en donde R representa Hal o metilo, L representa Cl, Br, I, OH o un grupo de OH transformado funcionalmente en un grupo reactivo, Halrepresenta F, Cl, Br o I y n es 1,2,3,4,5 o 6, en la forma deuna acilacion de Fri edel-Crafts catalizada por halogenuros metálicos del tipo R-Al(Cl)2 queque son ácidos de Lewis y en los cuales R repreenta A oarilo, A representa alquilo de 1 a 6 átomos de C, arilo representa fenilo no sustituido o mono odisustituido con A, OA o Ha l, Hal representa F o Cl, o b)cuando X representa H, H y R, R1,R2 y n tienen los significados indicados, se reduce un compuesto de formula (1), en donde X representa O y R, R1 y R2 y ntienen los significados indicados,con hidruros complejos y con la activacion de halogenuros metálicos del tipo R-Al(Cl)2 que son ácidos de Lewis y en los cuales R representa A o arilo, A representa alquilo de 1 a 6 átomos de C, arilo representa fenilo no sustituido o mono odisustituido con A, OA o Hal, Hal represen ta F o Cl, y/o se transforma una base de formula (1), así obtenida, en una de sus sales por adicion de un ácido. Los ensayos realizados en el marco de la síntesis de medicamentos revelaronsorprendentemente que los compuestos de formula (1) pueden ser obtenidos con rendimientos superiores o al menos
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19858340A DE19858340A1 (de) | 1998-12-17 | 1998-12-17 | Verfahren zur Herstellung von 3-Alkanoyl- und 3-Alkylindolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR021901A1 true AR021901A1 (es) | 2002-09-04 |
Family
ID=7891485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP990106531A AR021901A1 (es) | 1998-12-17 | 1999-12-17 | Un procedimiento para preparar 3-alcanoilindoles y 3-alquilindoles. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6509475B1 (es) |
| EP (1) | EP1140824B1 (es) |
| JP (2) | JP4846905B2 (es) |
| KR (1) | KR100612628B1 (es) |
| CN (1) | CN1155568C (es) |
| AR (1) | AR021901A1 (es) |
| AT (1) | ATE267169T1 (es) |
| AU (1) | AU763522B2 (es) |
| BR (1) | BR9916187B1 (es) |
| CA (1) | CA2355138C (es) |
| CZ (1) | CZ301643B6 (es) |
| DE (2) | DE19858340A1 (es) |
| DK (1) | DK1140824T3 (es) |
| ES (1) | ES2221471T3 (es) |
| HK (1) | HK1043363B (es) |
| HU (1) | HU228760B1 (es) |
| ID (1) | ID29053A (es) |
| MY (1) | MY121854A (es) |
| NO (1) | NO319864B1 (es) |
| PL (1) | PL196956B1 (es) |
| PT (1) | PT1140824E (es) |
| RU (1) | RU2260589C2 (es) |
| SI (1) | SI1140824T1 (es) |
| SK (1) | SK286532B6 (es) |
| TW (1) | TWI224096B (es) |
| WO (1) | WO2000035872A1 (es) |
| ZA (1) | ZA200105841B (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6800637B2 (en) | 2002-09-12 | 2004-10-05 | Wyeth | Antidepressant indolealkyl derivatives of heterocycle-fused benzodioxan methylamines |
| CN102267985B (zh) * | 2011-06-15 | 2015-12-09 | 上海医药工业研究院 | 维拉佐酮或其盐酸盐的制备方法 |
| CN102267932A (zh) * | 2011-06-15 | 2011-12-07 | 上海医药工业研究院 | 4-(5-氰基-1h-吲哚-3-基)丁基取代磺酸酯类化合物及其应用 |
| CN102249979A (zh) * | 2011-07-12 | 2011-11-23 | 上海开义医药化工有限公司 | 3-(4-氯丁酰基)-1h-吲哚-5-甲氰的制备方法 |
| WO2013114338A1 (en) * | 2012-02-01 | 2013-08-08 | Ranbaxy Laboratories Limited | Process for the preparation of vilazodone or its pharmaceutically acceptable salts |
| CN102690224A (zh) * | 2012-04-16 | 2012-09-26 | 淮海工学院 | 维拉唑酮中间体3-(4-氯丁基)-1h-5-氰基吲哚的制备方法 |
| US20150126525A1 (en) | 2012-05-11 | 2015-05-07 | Dr. Reddy's Laboratories Limited | Crystalline forms of vilazodone hydrochloride and vilazodone free base |
| CN102659660B (zh) * | 2012-05-11 | 2014-07-02 | 杭州和泽医药科技有限公司 | 3-(4-氯丁基)-1h-吲哚-5-氰基的制备方法及其应用 |
| CN102796037B (zh) * | 2012-08-09 | 2013-11-06 | 成都苑东药业有限公司 | 一种3-(4-(4-取代哌嗪)-1-丁酰基)吲哚-5-甲腈及其用途 |
| US9533949B2 (en) | 2012-09-12 | 2017-01-03 | Apotex Pharmachem Inc. | Processes for the preparation of 3-alkyl indoles |
| WO2014049609A2 (en) | 2012-09-26 | 2014-04-03 | Cadila Healthcare Limited | Novel salts of vilazodone |
| CN102875440B (zh) * | 2012-10-30 | 2014-10-08 | 江西隆莱生物制药有限公司 | 3-（4-氯丁基）-5-氰基吲哚的制备方法 |
| CN102911105B (zh) * | 2012-11-12 | 2013-12-04 | 辽宁科技大学 | 一种3-芳酰基吲哚化合物的合成方法 |
| CN104072401A (zh) * | 2013-03-25 | 2014-10-01 | 天津药物研究院 | 一种制备3-（4-氯丁酰基）-5-氰基吲哚的方法 |
| CN103304466A (zh) * | 2013-05-18 | 2013-09-18 | 嘉兴中科化学有限公司 | 一种3-烷基取代吲哚类化合物的合成方法 |
| CN103467357B (zh) * | 2013-09-13 | 2016-02-10 | 陕西步长高新制药有限公司 | 一种制备维拉唑酮中间体3-(4-氯丁基)-1h-吲哚-5-氰基的方法 |
| CN104592087B (zh) * | 2013-11-01 | 2016-06-15 | 北京英科博雅科技有限公司 | 一种盐酸维拉佐酮中间体3-（4-氯丁基）-1h-5-氰基吲哚的制备方法 |
| CN105801566A (zh) * | 2014-12-30 | 2016-07-27 | 山东方明药业集团股份有限公司 | 一种盐酸维拉佐酮的制备方法 |
| CN109265386B (zh) * | 2018-11-15 | 2021-02-09 | 四川大学 | 一种通过c-h活化合成3-酰基化吲哚衍生物的新方法 |
| CN111087339A (zh) * | 2019-11-13 | 2020-05-01 | 上海星酶生物科技有限公司 | 一种3-(4-氯丁基)吲哚-5-甲腈的生产工艺 |
| CN111087340B (zh) * | 2019-11-29 | 2021-12-07 | 上海应用技术大学 | 一种维拉佐酮中间体的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1043340A (en) * | 1974-06-17 | 1978-11-28 | Ethyl Corporation | Preparation of 5-aroyl-pyrrole compounds |
| US4187230A (en) * | 1975-05-27 | 1980-02-05 | Ethyl Corporation | Preparation of 5-aroyl-pyrrole compounds |
| US5290946A (en) * | 1988-10-13 | 1994-03-01 | Sandoz Ltd. | Processes for the synthesis of 3-(substituted indolyl-2-yl)propenaldehydes |
| GB2240105B (en) * | 1990-01-19 | 1993-06-09 | Technology Finance Corp | Process for the production of 3-(1-amino-1,3-dicarboxy-3-hydroxy-but-4-yl) indole |
| US5157122A (en) * | 1991-01-18 | 1992-10-20 | Merck & Co., Inc. | Process for the preparation of 3-unsubstituted indoles using methane sulfonic acid as an additional catalyst |
| DE4333254A1 (de) * | 1993-09-30 | 1995-04-06 | Merck Patent Gmbh | Piperidine und Piperazine |
-
1998
- 1998-12-17 DE DE19858340A patent/DE19858340A1/de not_active Withdrawn
-
1999
- 1999-12-01 BR BRPI9916187-7A patent/BR9916187B1/pt not_active IP Right Cessation
- 1999-12-01 PL PL348060A patent/PL196956B1/pl unknown
- 1999-12-01 CA CA002355138A patent/CA2355138C/en not_active Expired - Fee Related
- 1999-12-01 HU HU0104957A patent/HU228760B1/hu not_active IP Right Cessation
- 1999-12-01 AU AU19689/00A patent/AU763522B2/en not_active Ceased
- 1999-12-01 CN CNB998143855A patent/CN1155568C/zh not_active Expired - Fee Related
- 1999-12-01 SI SI9930625T patent/SI1140824T1/xx unknown
- 1999-12-01 EP EP99963352A patent/EP1140824B1/de not_active Expired - Lifetime
- 1999-12-01 WO PCT/EP1999/009334 patent/WO2000035872A1/de active IP Right Grant
- 1999-12-01 AT AT99963352T patent/ATE267169T1/de active
- 1999-12-01 JP JP2000588134A patent/JP4846905B2/ja not_active Expired - Fee Related
- 1999-12-01 PT PT99963352T patent/PT1140824E/pt unknown
- 1999-12-01 SK SK812-2001A patent/SK286532B6/sk not_active IP Right Cessation
- 1999-12-01 ES ES99963352T patent/ES2221471T3/es not_active Expired - Lifetime
- 1999-12-01 US US09/857,793 patent/US6509475B1/en not_active Expired - Lifetime
- 1999-12-01 DE DE59909543T patent/DE59909543D1/de not_active Expired - Lifetime
- 1999-12-01 CZ CZ20012118A patent/CZ301643B6/cs not_active IP Right Cessation
- 1999-12-01 ID IDW00200101416A patent/ID29053A/id unknown
- 1999-12-01 DK DK99963352T patent/DK1140824T3/da active
- 1999-12-01 KR KR1020017007544A patent/KR100612628B1/ko not_active IP Right Cessation
- 1999-12-01 RU RU2001119278/04A patent/RU2260589C2/ru not_active IP Right Cessation
- 1999-12-13 MY MYPI99005406A patent/MY121854A/en unknown
- 1999-12-17 AR ARP990106531A patent/AR021901A1/es active IP Right Grant
-
2000
- 2000-03-07 TW TW088122270A patent/TWI224096B/zh not_active IP Right Cessation
-
2001
- 2001-06-15 NO NO20012963A patent/NO319864B1/no not_active IP Right Cessation
- 2001-07-16 ZA ZA200105841A patent/ZA200105841B/en unknown
-
2002
- 2002-06-20 HK HK02104616.4A patent/HK1043363B/zh not_active IP Right Cessation
-
2011
- 2011-07-08 JP JP2011151377A patent/JP5400100B2/ja not_active Expired - Fee Related
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| FG | Grant, registration |