BR9916187A - Processo para a preparação de 3-alcanoìla e 3-alquilindóis - Google Patents

Processo para a preparação de 3-alcanoìla e 3-alquilindóis

Info

Publication number
BR9916187A
BR9916187A BR9916187-7A BR9916187A BR9916187A BR 9916187 A BR9916187 A BR 9916187A BR 9916187 A BR9916187 A BR 9916187A BR 9916187 A BR9916187 A BR 9916187A
Authority
BR
Brazil
Prior art keywords
formula
compound
preparation
acid
defined above
Prior art date
Application number
BR9916187-7A
Other languages
English (en)
Other versions
BR9916187B1 (pt
Inventor
Andreas Bathe
Herbert Tilly
Original Assignee
Merck Patent Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Publication of BR9916187A publication Critical patent/BR9916187A/pt
Publication of BR9916187B1 publication Critical patent/BR9916187B1/pt

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

Patente de Invenção: <B>"PROCESSO PARA A PREPARAçãO DE 3-ALCANOIL E 3-ALQUILINDOIS"<D>. na qual R, R¹, R² e n são conforme definidos na reivindicação 1, e X é O ou H, H seus sais aditivos ácidos, caracterizado pelo fato de que a) se X é O e R. R¹. R² e n são conforme definidos acima, um composto da fórmula II na qual R¹ e R² são conforme definidos na reivindicação 1 é feita uma reação com um composto da fórmula III R-(CH~ 2~)~ n~-CO-L na qual R, L e n são conforme definidos na reivindicação 1, em uma acilação Friedel-Crafts com catálise de haletos metálicos de ácido Lewis do tipo R'-Al(Cl)~ 2~, na qual R' é conforme definido na reivindicação 1, ou b) se X é H,H e R, R¹, R² e n são conforme definidos acima, um composto da fórmula I na qual X é O e R, R¹, R² e n são conforme definidos acima, é reduzido usando-se hidretos complexos com ativação por haletos metálicos de ácido Lewis do tipo R'-Al(Cl)~ 2~, na qual R' é conforme definido na reivindicação 1, e/ou em que uma base resultante da fórmula 1 é convertida em um dos seus sais aditivos ácidos por tratamento com um ácido.
BRPI9916187-7A 1998-12-17 1999-12-01 processo para a preparação de 3-alcanoìla e 3-alquilindóis. BR9916187B1 (pt)

Applications Claiming Priority (2)

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
PCT/EP1999/009334 WO2000035872A1 (de) 1998-12-17 1999-12-01 Verfahren zur herstellung von 3-alkanoyl- und 3-alkylindolen

Publications (2)

Publication Number Publication Date
BR9916187A true BR9916187A (pt) 2001-09-04
BR9916187B1 BR9916187B1 (pt) 2010-11-16

Family

ID=7891485

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI9916187-7A BR9916187B1 (pt) 1998-12-17 1999-12-01 processo para a preparação de 3-alcanoìla e 3-alquilindóis.

Country Status (27)

Country Link
US (1) US6509475B1 (pt)
EP (1) EP1140824B1 (pt)
JP (2) JP4846905B2 (pt)
KR (1) KR100612628B1 (pt)
CN (1) CN1155568C (pt)
AR (1) AR021901A1 (pt)
AT (1) ATE267169T1 (pt)
AU (1) AU763522B2 (pt)
BR (1) BR9916187B1 (pt)
CA (1) CA2355138C (pt)
CZ (1) CZ301643B6 (pt)
DE (2) DE19858340A1 (pt)
DK (1) DK1140824T3 (pt)
ES (1) ES2221471T3 (pt)
HK (1) HK1043363B (pt)
HU (1) HU228760B1 (pt)
ID (1) ID29053A (pt)
MY (1) MY121854A (pt)
NO (1) NO319864B1 (pt)
PL (1) PL196956B1 (pt)
PT (1) PT1140824E (pt)
RU (1) RU2260589C2 (pt)
SI (1) SI1140824T1 (pt)
SK (1) SK286532B6 (pt)
TW (1) TWI224096B (pt)
WO (1) WO2000035872A1 (pt)
ZA (1) ZA200105841B (pt)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
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
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
WO2013168126A1 (en) 2012-05-11 2013-11-14 Dr.Reddys Laboratories Limited Crystalline forms of vilazodone hydrochloride and vilazodone free base
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)

* Cited by examiner, † Cited by third party
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
ATE104961T1 (de) * 1990-01-19 1994-05-15 Technology Finance Corp Verfahren zur herstellung von 3-(1-amino-1,3dicarboxy-3-hydroxy-but-4-yl)-indol.
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

Also Published As

Publication number Publication date
HUP0104957A2 (hu) 2002-04-29
JP2012020997A (ja) 2012-02-02
AU1968900A (en) 2000-07-03
CA2355138A1 (en) 2000-06-22
TWI224096B (en) 2004-11-21
HK1043363A1 (en) 2002-09-13
PL196956B1 (pl) 2008-02-29
JP4846905B2 (ja) 2011-12-28
ZA200105841B (en) 2002-10-16
JP2002532469A (ja) 2002-10-02
EP1140824B1 (de) 2004-05-19
HU228760B1 (en) 2013-05-28
ES2221471T3 (es) 2004-12-16
NO20012963L (no) 2001-06-15
KR100612628B1 (ko) 2006-08-14
SI1140824T1 (en) 2004-10-31
WO2000035872A1 (de) 2000-06-22
DE59909543D1 (de) 2004-06-24
RU2260589C2 (ru) 2005-09-20
HUP0104957A3 (en) 2002-11-28
DK1140824T3 (da) 2004-09-13
CZ301643B6 (cs) 2010-05-12
CN1330635A (zh) 2002-01-09
DE19858340A1 (de) 2000-06-21
SK286532B6 (sk) 2008-12-05
EP1140824A1 (de) 2001-10-10
CN1155568C (zh) 2004-06-30
KR20010089585A (ko) 2001-10-06
US6509475B1 (en) 2003-01-21
ID29053A (id) 2001-07-26
NO319864B1 (no) 2005-09-26
CA2355138C (en) 2009-11-17
ATE267169T1 (de) 2004-06-15
AR021901A1 (es) 2002-09-04
HK1043363B (zh) 2005-04-08
MY121854A (en) 2006-02-28
BR9916187B1 (pt) 2010-11-16
NO20012963D0 (no) 2001-06-15
PL348060A1 (en) 2002-05-06
SK8122001A3 (en) 2001-12-03
AU763522B2 (en) 2003-07-24
JP5400100B2 (ja) 2014-01-29
CZ20012118A3 (cs) 2001-09-12
PT1140824E (pt) 2004-10-29

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Legal Events

Date Code Title Description
B06A Patent application procedure suspended [chapter 6.1 patent gazette]
B09A Decision: intention to grant [chapter 9.1 patent gazette]
B16A Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]

Free format text: PRAZO DE VALIDADE: 10 (DEZ) ANOS CONTADOS A PARTIR DE 16/11/2010, OBSERVADAS AS CONDICOES LEGAIS.

B21A Patent or certificate of addition expired [chapter 21.1 patent gazette]

Free format text: PATENTE EXTINTA EM 16.11.2020