JP2003505458A5 - - Google Patents
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- Publication number
- JP2003505458A5 JP2003505458A5 JP2001512519A JP2001512519A JP2003505458A5 JP 2003505458 A5 JP2003505458 A5 JP 2003505458A5 JP 2001512519 A JP2001512519 A JP 2001512519A JP 2001512519 A JP2001512519 A JP 2001512519A JP 2003505458 A5 JP2003505458 A5 JP 2003505458A5
- Authority
- JP
- Japan
- Prior art keywords
- methanone
- indol
- piperazin
- hydrochloride
- ethyl
- 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.)
- Granted
Links
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- -1 benzenesulfonyloxy, p-toluenesulfonyloxy Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- BPVFKPUPOSRPPI-UHFFFAOYSA-N 1h-indol-4-yl-[4-(2-thiophen-2-ylethyl)piperazin-1-yl]methanone Chemical compound C=1C=CC=2NC=CC=2C=1C(=O)N(CC1)CCN1CCC1=CC=CS1 BPVFKPUPOSRPPI-UHFFFAOYSA-N 0.000 description 1
- SGCYSHURTIOGSZ-UHFFFAOYSA-N 1h-indol-4-yl-[4-(2-thiophen-3-ylethyl)piperazin-1-yl]methanone Chemical compound C=1C=CC=2NC=CC=2C=1C(=O)N(CC1)CCN1CCC=1C=CSC=1 SGCYSHURTIOGSZ-UHFFFAOYSA-N 0.000 description 1
- WOSOETCNFILDMJ-UHFFFAOYSA-N 1h-indol-5-yl-[4-(2-phenylethyl)piperazin-1-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)N(CC1)CCN1CCC1=CC=CC=C1 WOSOETCNFILDMJ-UHFFFAOYSA-N 0.000 description 1
- RZNZQLGCNBDVCR-UHFFFAOYSA-N 1h-indol-6-yl-[4-(2-phenylethyl)piperazin-1-yl]methanone Chemical compound C=1C=C2C=CNC2=CC=1C(=O)N(CC1)CCN1CCC1=CC=CC=C1 RZNZQLGCNBDVCR-UHFFFAOYSA-N 0.000 description 1
- HFGRCURKGSRTFM-UHFFFAOYSA-N 1h-indol-6-yl-[4-(2-thiophen-2-ylethyl)piperazin-1-yl]methanone Chemical compound C=1C=C2C=CNC2=CC=1C(=O)N(CC1)CCN1CCC1=CC=CS1 HFGRCURKGSRTFM-UHFFFAOYSA-N 0.000 description 1
- SFAVAAQSVUQWCB-UHFFFAOYSA-N 1h-indol-6-yl-[4-(2-thiophen-3-ylethyl)piperazin-1-yl]methanone Chemical compound C=1C=C2C=CNC2=CC=1C(=O)N(CC1)CCN1CCC=1C=CSC=1 SFAVAAQSVUQWCB-UHFFFAOYSA-N 0.000 description 1
- RISLQOLUWBPIBT-UHFFFAOYSA-N 7-[4-[2-(2-fluorophenyl)ethyl]piperazine-1-carbonyl]-1h-indole-3-carbonitrile Chemical compound FC1=CC=CC=C1CCN1CCN(C(=O)C=2C=3NC=C(C=3C=CC=2)C#N)CC1 RISLQOLUWBPIBT-UHFFFAOYSA-N 0.000 description 1
- SOONQGBOUDZOIC-UHFFFAOYSA-N 7-[4-[2-(4-fluorophenyl)ethyl]piperazine-1-carbonyl]-1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1C(=O)N(CC1)CCN1CCC1=CC=C(F)C=C1 SOONQGBOUDZOIC-UHFFFAOYSA-N 0.000 description 1
- PRBFOWAWDTWTSF-UHFFFAOYSA-N 7-[4-[2-(5-chlorothiophen-2-yl)ethyl]piperazine-1-carbonyl]-1h-indole-3-carbonitrile Chemical compound S1C(Cl)=CC=C1CCN1CCN(C(=O)C=2C=3NC=C(C=3C=CC=2)C#N)CC1 PRBFOWAWDTWTSF-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- AQRLDDAFYYAIJP-UHFFFAOYSA-N Pruvanserin Chemical compound C1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C=3NC=C(C=3C=CC=2)C#N)CC1 AQRLDDAFYYAIJP-UHFFFAOYSA-N 0.000 description 1
- FOVICFIAZDFOQR-UHFFFAOYSA-N [4-[2-(2,5-dichlorothiophen-3-yl)ethyl]piperazin-1-yl]-(1h-indol-4-yl)methanone Chemical compound S1C(Cl)=CC(CCN2CCN(CC2)C(=O)C=2C=3C=CNC=3C=CC=2)=C1Cl FOVICFIAZDFOQR-UHFFFAOYSA-N 0.000 description 1
- IXWJVFZAWRNDHS-UHFFFAOYSA-N [4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]-(1h-indol-4-yl)methanone Chemical compound C1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C=3C=CNC=3C=CC=2)CC1 IXWJVFZAWRNDHS-UHFFFAOYSA-N 0.000 description 1
- GKUPWPKKZCZYFT-UHFFFAOYSA-N [4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]-(1h-indol-6-yl)methanone Chemical compound C1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C=C3NC=CC3=CC=2)CC1 GKUPWPKKZCZYFT-UHFFFAOYSA-N 0.000 description 1
- ZJBYTFKPIHNUHE-UHFFFAOYSA-N [4-[2-(5-chlorothiophen-2-yl)ethyl]piperazin-1-yl]-(1h-indol-4-yl)methanone Chemical compound S1C(Cl)=CC=C1CCN1CCN(C(=O)C=2C=3C=CNC=3C=CC=2)CC1 ZJBYTFKPIHNUHE-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- BKXVVCILCIUCLG-UHFFFAOYSA-N raloxifene hydrochloride Chemical compound [H+].[Cl-].C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 BKXVVCILCIUCLG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19934433.7 | 1999-07-22 | ||
| DE19934433A DE19934433A1 (de) | 1999-07-22 | 1999-07-22 | N-(Indolcarbonyl-)piperazinderivate |
| PCT/EP2000/006464 WO2001007435A2 (de) | 1999-07-22 | 2000-07-07 | N-(indolcarbonyl-)piperazinderivate als 5-ht2a-rezeptor liganden |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011166851A Division JP2012006940A (ja) | 1999-07-22 | 2011-07-29 | Ｎ−（インドールカルボニル）ピペラジン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003505458A JP2003505458A (ja) | 2003-02-12 |
| JP2003505458A5 true JP2003505458A5 (https=) | 2011-04-14 |
| JP5242871B2 JP5242871B2 (ja) | 2013-07-24 |
Family
ID=7915702
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001512519A Expired - Fee Related JP5242871B2 (ja) | 1999-07-22 | 2000-07-07 | Ｎ−（インドールカルボニル）ピペラジン誘導体 |
| JP2011166851A Pending JP2012006940A (ja) | 1999-07-22 | 2011-07-29 | Ｎ−（インドールカルボニル）ピペラジン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011166851A Pending JP2012006940A (ja) | 1999-07-22 | 2011-07-29 | Ｎ−（インドールカルボニル）ピペラジン誘導体 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US6838461B1 (https=) |
| EP (1) | EP1198453B9 (https=) |
| JP (2) | JP5242871B2 (https=) |
| KR (1) | KR100779207B1 (https=) |
| CN (1) | CN1229345C (https=) |
| AR (1) | AR024819A1 (https=) |
| AT (1) | ATE236877T1 (https=) |
| AU (1) | AU770411B2 (https=) |
| BR (1) | BR0012607A (https=) |
| CA (1) | CA2383779C (https=) |
| CZ (1) | CZ300510B6 (https=) |
| DE (2) | DE19934433A1 (https=) |
| DK (1) | DK1198453T5 (https=) |
| ES (1) | ES2192535T3 (https=) |
| HK (1) | HK1048636B (https=) |
| HU (1) | HUP0201988A3 (https=) |
| MX (1) | MXPA02000730A (https=) |
| MY (1) | MY122531A (https=) |
| NO (1) | NO322154B1 (https=) |
| PL (1) | PL201893B1 (https=) |
| PT (1) | PT1198453E (https=) |
| RU (1) | RU2251548C2 (https=) |
| SK (1) | SK286066B6 (https=) |
| UA (1) | UA73518C2 (https=) |
| WO (1) | WO2001007435A2 (https=) |
| ZA (1) | ZA200201486B (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6589954B1 (en) | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| IL146309A (en) | 1999-05-21 | 2008-03-20 | Scios Inc | Derivatives of the indole type and pharmaceutical preparations containing them as inhibitors of kinase p38 |
| DE19934432A1 (de) * | 1999-07-22 | 2001-02-01 | Merck Patent Gmbh | Indolderivate |
| DE19934433A1 (de) * | 1999-07-22 | 2001-01-25 | Merck Patent Gmbh | N-(Indolcarbonyl-)piperazinderivate |
| US20020156453A1 (en) * | 1999-10-14 | 2002-10-24 | Pettis Ronald J. | Method and device for reducing therapeutic dosage |
| US20020095134A1 (en) * | 1999-10-14 | 2002-07-18 | Pettis Ronald J. | Method for altering drug pharmacokinetics based on medical delivery platform |
| US8465468B1 (en) | 2000-06-29 | 2013-06-18 | Becton, Dickinson And Company | Intradermal delivery of substances |
| DE10102053A1 (de) * | 2001-01-17 | 2002-07-18 | Merck Patent Gmbh | Piperazinylcarbonylchinoline und -isochinoline |
| DE60212841T2 (de) | 2001-06-15 | 2007-06-21 | F. Hoffmann-La Roche Ag | 4 piperazinylindolderivate mit affinität zum 5-ht6-rezeptor |
| WO2003002069A2 (en) * | 2001-06-29 | 2003-01-09 | Becton, Dickinson And Company | Intradermal delivery of vaccines and gene therapeutic agents via microcannula |
| DE10157673A1 (de) * | 2001-11-24 | 2003-06-05 | Merck Patent Gmbh | Verwendung von N-(Indolcarbonyl-)piperazinderivaten |
| GB0203811D0 (en) * | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| DE10212564B4 (de) * | 2002-03-12 | 2007-04-19 | Neurobiotec Gmbh | 1-Allyl-ergotalkaloid-Derivate und ihre Verwendung zur Prophylaxe und Therapie von Migräne |
| DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| AU2003262888A1 (en) * | 2002-08-30 | 2004-03-19 | Becton, Dickinson And Company | Method of controlling pharmacokinetics of immunomodulatory compounds |
| DE10246357A1 (de) * | 2002-10-04 | 2004-04-15 | Merck Patent Gmbh | Verwendung von 5-HT2Rezeptorantagonisten |
| AU2004264839B2 (en) * | 2003-06-13 | 2009-06-04 | Becton, Dickinson And Company | Improved intra-dermal delivery of biologically active agents |
| AU2004270113A1 (en) * | 2003-08-26 | 2005-03-17 | Becton, Dickinson And Company | Methods for intradermal delivery of therapeutics agents |
| WO2005091922A2 (en) * | 2004-03-03 | 2005-10-06 | Becton, Dickinson And Company | Methods and devices for improving delivery of a substance to skin |
| CN101022806A (zh) * | 2004-04-15 | 2007-08-22 | 萨马里坦药品公司 | （4－烷基哌嗪基）（苯基）甲酮在治疗阿尔茨海默病中的应用 |
| WO2005115360A2 (en) * | 2004-05-11 | 2005-12-08 | Becton, Dickinson And Company | Formulations of anti-pain agents and methods of using the same |
| DE102004047517A1 (de) | 2004-09-28 | 2006-03-30 | Merck Patent Gmbh | Neuartige Kristallform von (3-Cyan-1H-indol-7-yl)-[4-(4-fluorphenethyl)-piperazin-1-yl]-methanon, Hydrochlorid |
| MX2007007558A (es) * | 2004-12-21 | 2007-07-24 | Hoffmann La Roche | Derivados de tetralina y de indano y usos de los mismos. |
| GT200600042A (es) | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
| AU2007248282B2 (en) * | 2006-05-05 | 2011-12-08 | Merck Patent Gmbh | Crystalline (3-cyano-1H-indol-7-yl)-[4-(4-fluorophenethyl)piperazin-1-yl]methanone phosphate |
| US7514433B2 (en) * | 2006-08-03 | 2009-04-07 | Hoffmann-La Roche Inc. | 1H-indole-6-yl-piperazin-1-yl-methanone derivatives |
| ES2379848T3 (es) * | 2007-05-14 | 2012-05-04 | Sk Biopharmaceuticals Co., Ltd. | Compuesto arilpiperazina arilalcanoil carbomoiloxi novedoso, composiciones farmacéuticas que comprenden el compuesto y método para tratar el dolor, ansiedad y depresión al administrar el compuesto |
| EP2008656A1 (en) * | 2007-06-28 | 2008-12-31 | Bergen Teknologioverforing AS | Compositions for the treatment of hyperphenylalaninemia |
| WO2009023253A2 (en) * | 2007-08-15 | 2009-02-19 | Arena Pharmaceuticals Inc. | IMIDAZO[L,2-α]PYRIDINE DERIVATIVES AS MODULATORS OF THE 5-HT2A SEROTONIN RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO |
| KR101062376B1 (ko) * | 2008-04-10 | 2011-09-06 | 한국화학연구원 | 신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물 |
| US9308323B2 (en) | 2011-11-15 | 2016-04-12 | Smiths Medical Asd, Inc. | Systems and methods for illuminated medical tubing detection and management indicating a characteristic of at least one infusion pump |
| RU2549963C1 (ru) * | 2014-04-08 | 2015-05-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Дальневосточный государственный медицинский университет" Министерства здравоохранения Российской Федерации (ГБОУ ВПО "ДВГМУ" Минздрава России) | Способ прогнозирования развития критической печеночной недостаточности на основании сывороточного уровня селена |
| CA3014572C (en) | 2016-02-25 | 2023-10-03 | Asceneuron S.A. | Acid addition salts of piperazine derivatives |
| GB2554371B (en) * | 2016-09-22 | 2019-10-09 | Resolute Energy Solutions Ltd | Well apparatus and associated methods |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU630334B2 (en) | 1987-09-24 | 1992-10-29 | Jencap Research Ltd. | Hormone preparations for hormone replacement therapy and contraceptive method |
| US5093341A (en) * | 1987-12-17 | 1992-03-03 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl piperidine derivatives useful as antithrombolytic agents |
| US5032598A (en) * | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents |
| US5032604A (en) * | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Class III antiarrhythmic agents |
| US5330986A (en) * | 1992-11-24 | 1994-07-19 | Hoechst-Roussel Pharmaceuticals Inc. | Indole-7-carboxamide derivatives |
| ZA954689B (en) | 1994-06-08 | 1996-01-29 | Lundbeck & Co As H | 4-Aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzothiophenemethyl) piperidines tetrahydropyridines or piperazines |
| EP0922042A1 (en) | 1996-08-09 | 1999-06-16 | Smithkline Beecham Corporation | Novel piperazine containing compounds |
| GB9718712D0 (en) * | 1997-09-03 | 1997-11-12 | Merck Sharp & Dohme | Theraputic Agents |
| DE19934433A1 (de) * | 1999-07-22 | 2001-01-25 | Merck Patent Gmbh | N-(Indolcarbonyl-)piperazinderivate |
| DE19934432A1 (de) * | 1999-07-22 | 2001-02-01 | Merck Patent Gmbh | Indolderivate |
| JPWO2005099240A1 (ja) * | 2004-04-07 | 2008-03-06 | 松下電器産業株式会社 | 情報交換支援装置、情報交換支援方法、及び情報交換支援プログラム |
-
1999
- 1999-07-22 DE DE19934433A patent/DE19934433A1/de not_active Withdrawn
-
2000
- 2000-07-07 RU RU2002103302/04A patent/RU2251548C2/ru not_active IP Right Cessation
- 2000-07-07 BR BR0012607-1A patent/BR0012607A/pt active Search and Examination
- 2000-07-07 AU AU62704/00A patent/AU770411B2/en not_active Ceased
- 2000-07-07 ES ES00949288T patent/ES2192535T3/es not_active Expired - Lifetime
- 2000-07-07 DK DK00949288T patent/DK1198453T5/da active
- 2000-07-07 HK HK03100811.4A patent/HK1048636B/zh not_active IP Right Cessation
- 2000-07-07 DE DE50001729T patent/DE50001729D1/de not_active Expired - Lifetime
- 2000-07-07 EP EP00949288A patent/EP1198453B9/de not_active Expired - Lifetime
- 2000-07-07 PT PT00949288T patent/PT1198453E/pt unknown
- 2000-07-07 UA UA2002021354A patent/UA73518C2/uk unknown
- 2000-07-07 SK SK51-2002A patent/SK286066B6/sk not_active IP Right Cessation
- 2000-07-07 CZ CZ20020068A patent/CZ300510B6/cs not_active IP Right Cessation
- 2000-07-07 JP JP2001512519A patent/JP5242871B2/ja not_active Expired - Fee Related
- 2000-07-07 KR KR1020027000315A patent/KR100779207B1/ko not_active Expired - Fee Related
- 2000-07-07 WO PCT/EP2000/006464 patent/WO2001007435A2/de not_active Ceased
- 2000-07-07 US US10/031,367 patent/US6838461B1/en not_active Expired - Lifetime
- 2000-07-07 CA CA2383779A patent/CA2383779C/en not_active Expired - Fee Related
- 2000-07-07 HU HU0201988A patent/HUP0201988A3/hu unknown
- 2000-07-07 CN CNB00810719XA patent/CN1229345C/zh not_active Expired - Fee Related
- 2000-07-07 AT AT00949288T patent/ATE236877T1/de not_active IP Right Cessation
- 2000-07-07 MX MXPA02000730A patent/MXPA02000730A/es active IP Right Grant
- 2000-07-07 PL PL353446A patent/PL201893B1/pl not_active IP Right Cessation
- 2000-07-20 MY MYPI20003320A patent/MY122531A/en unknown
- 2000-07-21 AR ARP000103775A patent/AR024819A1/es active IP Right Grant
-
2002
- 2002-01-21 NO NO20020307A patent/NO322154B1/no not_active IP Right Cessation
- 2002-02-21 ZA ZA200201486A patent/ZA200201486B/en unknown
-
2004
- 2004-12-17 US US11/013,908 patent/US7084143B2/en not_active Expired - Fee Related
-
2011
- 2011-07-29 JP JP2011166851A patent/JP2012006940A/ja active Pending
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