KR100612628B1 - 3-알카노일인돌 및 3-알킬인돌의 제조 방법 - Google Patents
3-알카노일인돌 및 3-알킬인돌의 제조 방법 Download PDFInfo
- Publication number
- KR100612628B1 KR100612628B1 KR1020017007544A KR20017007544A KR100612628B1 KR 100612628 B1 KR100612628 B1 KR 100612628B1 KR 1020017007544 A KR1020017007544 A KR 1020017007544A KR 20017007544 A KR20017007544 A KR 20017007544A KR 100612628 B1 KR100612628 B1 KR 100612628B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- hal
- compound
- defined above
- acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
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 |
| DE19858340.0 | 1998-12-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20010089585A KR20010089585A (ko) | 2001-10-06 |
| KR100612628B1 true KR100612628B1 (ko) | 2006-08-14 |
Family
ID=7891485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020017007544A Expired - Fee Related KR100612628B1 (ko) | 1998-12-17 | 1999-12-01 | 3-알카노일인돌 및 3-알킬인돌의 제조 방법 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6509475B1 (enExample) |
| EP (1) | EP1140824B1 (enExample) |
| JP (2) | JP4846905B2 (enExample) |
| KR (1) | KR100612628B1 (enExample) |
| CN (1) | CN1155568C (enExample) |
| AR (1) | AR021901A1 (enExample) |
| AT (1) | ATE267169T1 (enExample) |
| AU (1) | AU763522B2 (enExample) |
| BR (1) | BR9916187B1 (enExample) |
| CA (1) | CA2355138C (enExample) |
| CZ (1) | CZ301643B6 (enExample) |
| DE (2) | DE19858340A1 (enExample) |
| DK (1) | DK1140824T3 (enExample) |
| ES (1) | ES2221471T3 (enExample) |
| HK (1) | HK1043363B (enExample) |
| HU (1) | HU228760B1 (enExample) |
| ID (1) | ID29053A (enExample) |
| MY (1) | MY121854A (enExample) |
| NO (1) | NO319864B1 (enExample) |
| PL (1) | PL196956B1 (enExample) |
| PT (1) | PT1140824E (enExample) |
| RU (1) | RU2260589C2 (enExample) |
| SI (1) | SI1140824T1 (enExample) |
| SK (1) | SK286532B6 (enExample) |
| TW (1) | TWI224096B (enExample) |
| WO (1) | WO2000035872A1 (enExample) |
| ZA (1) | ZA200105841B (enExample) |
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 |
| 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 |
| US20150126525A1 (en) | 2012-05-11 | 2015-05-07 | Dr. Reddy's 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 |
| WO2014040164A1 (en) | 2012-09-12 | 2014-03-20 | 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4187230A (en) * | 1975-05-27 | 1980-02-05 | Ethyl Corporation | Preparation of 5-aroyl-pyrrole compounds |
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 |
| 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. |
| PL168919B1 (pl) * | 1990-10-15 | 1996-05-31 | Pfizer | Sposób wytwarzania nowych pochodnych indolu PL PL PL PL |
| 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 ES ES99963352T patent/ES2221471T3/es not_active Expired - Lifetime
- 1999-12-01 AT AT99963352T patent/ATE267169T1/de active
- 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 PT PT99963352T patent/PT1140824E/pt unknown
- 1999-12-01 ID IDW00200101416A patent/ID29053A/id unknown
- 1999-12-01 SI SI9930625T patent/SI1140824T1/xx unknown
- 1999-12-01 EP EP99963352A patent/EP1140824B1/de not_active Expired - Lifetime
- 1999-12-01 HK HK02104616.4A patent/HK1043363B/zh not_active IP Right Cessation
- 1999-12-01 JP JP2000588134A patent/JP4846905B2/ja not_active Expired - Fee Related
- 1999-12-01 AU AU19689/00A patent/AU763522B2/en not_active Ceased
- 1999-12-01 PL PL348060A patent/PL196956B1/pl unknown
- 1999-12-01 RU RU2001119278/04A patent/RU2260589C2/ru not_active IP Right Cessation
- 1999-12-01 KR KR1020017007544A patent/KR100612628B1/ko not_active Expired - Fee Related
- 1999-12-01 BR BRPI9916187-7A patent/BR9916187B1/pt not_active IP Right Cessation
- 1999-12-01 WO PCT/EP1999/009334 patent/WO2000035872A1/de not_active Ceased
- 1999-12-01 SK SK812-2001A patent/SK286532B6/sk not_active IP Right Cessation
- 1999-12-01 DK DK99963352T patent/DK1140824T3/da active
- 1999-12-01 HU HU0104957A patent/HU228760B1/hu not_active IP Right Cessation
- 1999-12-01 CA CA002355138A patent/CA2355138C/en not_active Expired - Fee Related
- 1999-12-01 CN CNB998143855A patent/CN1155568C/zh not_active Expired - Fee Related
- 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
-
2011
- 2011-07-08 JP JP2011151377A patent/JP5400100B2/ja not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4187230A (en) * | 1975-05-27 | 1980-02-05 | Ethyl Corporation | Preparation of 5-aroyl-pyrrole compounds |
Non-Patent Citations (2)
| Title |
|---|
| J. Org. Chem. 57(7), 2143-2147(1992) * |
| Liebigs Ann. Chem. 749-752(1988) * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100612628B1 (ko) | 3-알카노일인돌 및 3-알킬인돌의 제조 방법 | |
| SK8962001A3 (en) | Method for the preparation of 5-cyanophthalide | |
| MXPA02008634A (es) | Metodo para la preparacion de citalopram. | |
| NO309324B1 (no) | Fremgangsmåte for fremstilling av N-metyl-3-(1-metyl-4- piperidinyl)-1H-indol-5-etansulfonamider | |
| AU603042B2 (en) | Process for the production of o2,2' -anhydro-1-(beta-d- arabinofuranosyl)thymine | |
| KR970001069B1 (ko) | 4-아미노페놀 유도체 및 그 제조방법 | |
| CA1302420C (en) | Indene derivatives and methods | |
| WO2006075139A2 (en) | Novel process for the preparation of substituted indoles | |
| US6531503B1 (en) | Benzofurane derivatives | |
| US5053513A (en) | Method of reducing a carbonyl containing acridine | |
| JP2004516315A (ja) | α−アミノ置換カルボン酸アミドの調製方法 | |
| US5574160A (en) | Syntheis of benzoquinolinones | |
| MXPA01006131A (en) | Method for producing 3-alkanoylindoles and 3-alkylindoles | |
| Vida et al. | Investigation in the 3, 4-dihydrocoumarin melilotic acid series | |
| WO2010004580A2 (en) | Process for preparing indole derivatives | |
| DK170505B1 (da) | Fremgangsmåde til fremstilling af 4-alkoxyalkyl-beta-carboliner | |
| JPH11507346A (ja) | ビニルスルフェン酸誘導体の合成方法 | |
| MXPA01005674A (en) | Method for the preparation of 5-cyanophthalide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R17-X000 | Change to representative recorded |
St.27 status event code: A-3-3-R10-R17-oth-X000 |
|
| PA0105 | International application |
St.27 status event code: A-0-1-A10-A15-nap-PA0105 |
|
| PG1501 | Laying open of application |
St.27 status event code: A-1-1-Q10-Q12-nap-PG1501 |
|
| A201 | Request for examination | ||
| P11-X000 | Amendment of application requested |
St.27 status event code: A-2-2-P10-P11-nap-X000 |
|
| P13-X000 | Application amended |
St.27 status event code: A-2-2-P10-P13-nap-X000 |
|
| PA0201 | Request for examination |
St.27 status event code: A-1-2-D10-D11-exm-PA0201 |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
St.27 status event code: A-1-2-D10-D21-exm-PE0902 |
|
| P11-X000 | Amendment of application requested |
St.27 status event code: A-2-2-P10-P11-nap-X000 |
|
| P13-X000 | Application amended |
St.27 status event code: A-2-2-P10-P13-nap-X000 |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
St.27 status event code: A-1-2-D10-D22-exm-PE0701 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
St.27 status event code: A-2-4-F10-F11-exm-PR0701 |
|
| PR1002 | Payment of registration fee |
St.27 status event code: A-2-2-U10-U12-oth-PR1002 Fee payment year number: 1 |
|
| PG1601 | Publication of registration |
St.27 status event code: A-4-4-Q10-Q13-nap-PG1601 |
|
| PR1001 | Payment of annual fee |
St.27 status event code: A-4-4-U10-U11-oth-PR1001 Fee payment year number: 4 |
|
| PR1001 | Payment of annual fee |
St.27 status event code: A-4-4-U10-U11-oth-PR1001 Fee payment year number: 5 |
|
| PR1001 | Payment of annual fee |
St.27 status event code: A-4-4-U10-U11-oth-PR1001 Fee payment year number: 6 |
|
| FPAY | Annual fee payment |
Payment date: 20120727 Year of fee payment: 7 |
|
| PR1001 | Payment of annual fee |
St.27 status event code: A-4-4-U10-U11-oth-PR1001 Fee payment year number: 7 |
|
| FPAY | Annual fee payment |
Payment date: 20130722 Year of fee payment: 8 |
|
| PR1001 | Payment of annual fee |
St.27 status event code: A-4-4-U10-U11-oth-PR1001 Fee payment year number: 8 |
|
| LAPS | Lapse due to unpaid annual fee | ||
| PC1903 | Unpaid annual fee |
St.27 status event code: A-4-4-U10-U13-oth-PC1903 Not in force date: 20140809 Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE |
|
| PC1903 | Unpaid annual fee |
St.27 status event code: N-4-6-H10-H13-oth-PC1903 Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE Not in force date: 20140809 |
|
| P22-X000 | Classification modified |
St.27 status event code: A-4-4-P10-P22-nap-X000 |
|
| R18-X000 | Changes to party contact information recorded |
St.27 status event code: A-5-5-R10-R18-oth-X000 |