JP2002507613A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2002507613A5 JP2002507613A5 JP2000537874A JP2000537874A JP2002507613A5 JP 2002507613 A5 JP2002507613 A5 JP 2002507613A5 JP 2000537874 A JP2000537874 A JP 2000537874A JP 2000537874 A JP2000537874 A JP 2000537874A JP 2002507613 A5 JP2002507613 A5 JP 2002507613A5
- Authority
- JP
- Japan
- Prior art keywords
- piperid
- fluorobenzyl
- propenyl
- melting point
- benzoxazol
- 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 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KSTICMFAFQGYSN-UHFFFAOYSA-N 5-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]prop-1-enyl]-1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CC=CC=2C=C3NC(=O)NC3=CC=2)CC1 KSTICMFAFQGYSN-UHFFFAOYSA-N 0.000 description 2
- GRCRMRUZDNKSBD-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]prop-1-enyl]-3H-1,3-benzothiazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CC=CC=2C=C3SC(=O)NC3=CC=2)CC1 GRCRMRUZDNKSBD-UHFFFAOYSA-N 0.000 description 2
- PUOAETJYKQITMO-FYJGNVAPSA-N (3E)-1-[1-(4-fluorophenyl)ethyl]-3-[[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]methylidene]piperidin-2-one Chemical compound C=1C=C(N2C=C(C)N=C2)C(OC)=CC=1\C=C(C1=O)/CCCN1C(C)C1=CC=C(F)C=C1 PUOAETJYKQITMO-FYJGNVAPSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- VXFJVYLYMPVVTQ-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]-2-methylprop-1-enyl]-3H-1,3-benzoxazol-2-one Chemical compound C=1C=C2NC(=O)OC2=CC=1C=C(C)CN(CC1)CCC1CC1=CC=C(F)C=C1 VXFJVYLYMPVVTQ-UHFFFAOYSA-N 0.000 description 1
- OVQXQXYBFNPNTP-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]prop-1-enyl]-3,4-dihydro-1H-quinolin-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CC=CC=2C=C3CCC(=O)NC3=CC=2)CC1 OVQXQXYBFNPNTP-UHFFFAOYSA-N 0.000 description 1
- CQYRNVNODQPZDL-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]prop-1-enyl]-3H-1,3-benzoxazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CC=CC=2C=C3OC(=O)NC3=CC=2)CC1 CQYRNVNODQPZDL-UHFFFAOYSA-N 0.000 description 1
- YNWAFHDAQQTVIT-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-3H-1,3-benzoxazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3OC(=O)NC3=CC=2)CC1 YNWAFHDAQQTVIT-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Description
【特許請求の範囲】
【請求項１】
以下のａ）〜ｄ）のいずれかのピペリジン誘導体、またはその生理学的に許容できる塩：
ａ）６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−３Ｈ−ベンゾキサゾール−２−オン、
ｂ）６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロピル｝−３Ｈ−ベンゾキサゾール−２−オン、
ｃ）６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−３Ｈ−ベンゾチアゾール−２−オン、
ｄ）５−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−１，３−ジヒドロベンズイミダゾール−２−オン。
【請求項１】
以下のａ）〜ｄ）のいずれかのピペリジン誘導体、またはその生理学的に許容できる塩：
ａ）６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−３Ｈ−ベンゾキサゾール−２−オン、
ｂ）６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロピル｝−３Ｈ−ベンゾキサゾール−２−オン、
ｃ）６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−３Ｈ−ベンゾチアゾール−２−オン、
ｄ）５−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−１，３−ジヒドロベンズイミダゾール−２−オン。
同様に以下の化合物が得られる：
６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］−２−メチルプロペニル｝−３Ｈ−ベンゾキサゾール−２−オン（融点１５６〜１６０℃：塩酸塩：融点２３０〜２３５℃）、
６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−３Ｈ−ベンゾチアゾール−２−オン、塩酸塩×Ｈ2Ｏ，融点９５〜９９℃：（分解）、
５−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−１，３−ジヒドロベンズイミダゾール−２−オン（融点２１８〜２２０℃：塩酸塩：融点２４３〜２４５℃）、
５−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−１，３−ジヒドロインドール−２−オン、
６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−３，４−ジヒドロ−１Ｈ−キノリン−２−オン。
６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］−２−メチルプロペニル｝−３Ｈ−ベンゾキサゾール−２−オン（融点１５６〜１６０℃：塩酸塩：融点２３０〜２３５℃）、
６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−３Ｈ−ベンゾチアゾール−２−オン、塩酸塩×Ｈ2Ｏ，融点９５〜９９℃：（分解）、
５−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−１，３−ジヒドロベンズイミダゾール−２−オン（融点２１８〜２２０℃：塩酸塩：融点２４３〜２４５℃）、
５−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−１，３−ジヒドロインドール−２−オン、
６−｛３−［４−（４−フルオロベンジル）ピペリド−１−イル］プロペニル｝−３，４−ジヒドロ−１Ｈ−キノリン−２−オン。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19812331.0 | 1998-03-20 | ||
| DE19812331A DE19812331A1 (de) | 1998-03-20 | 1998-03-20 | Piperidinderivate |
| PCT/EP1999/001573 WO1999048891A1 (de) | 1998-03-20 | 1999-03-11 | 1-(3 -heteroarylpropyl- oder -prop -2-enyl) -4-benzylpiperidine als nmda-rezeptor-antagonisten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002507613A JP2002507613A (ja) | 2002-03-12 |
| JP2002507613A5 true JP2002507613A5 (ja) | 2010-01-21 |
| JP4451565B2 JP4451565B2 (ja) | 2010-04-14 |
Family
ID=7861717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000537874A Expired - Fee Related JP4451565B2 (ja) | 1998-03-20 | 1999-03-11 | ピペリジン誘導体 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6548516B1 (ja) |
| EP (1) | EP1068202B1 (ja) |
| JP (1) | JP4451565B2 (ja) |
| KR (1) | KR20010042047A (ja) |
| CN (1) | CN1123571C (ja) |
| AR (1) | AR014747A1 (ja) |
| AT (1) | ATE416173T1 (ja) |
| AU (1) | AU747900B2 (ja) |
| BR (1) | BR9908902A (ja) |
| CA (1) | CA2324339C (ja) |
| DE (2) | DE19812331A1 (ja) |
| DK (1) | DK1068202T3 (ja) |
| ES (1) | ES2316184T3 (ja) |
| HU (1) | HUP0101220A3 (ja) |
| ID (1) | ID26125A (ja) |
| NO (1) | NO20004668L (ja) |
| PL (1) | PL342732A1 (ja) |
| PT (1) | PT1068202E (ja) |
| RU (1) | RU2217429C2 (ja) |
| SK (1) | SK13692000A3 (ja) |
| WO (1) | WO1999048891A1 (ja) |
| ZA (1) | ZA992191B (ja) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20030007797A (ko) * | 2000-05-31 | 2003-01-23 | 워너-램버트 캄파니 | 바이시클릭 시클로헥실아민 및 ｎｍｄａ 수용체길항제로서의 그의 용도 |
| AU2001263130A1 (en) | 2000-06-06 | 2001-12-17 | Warner Lambert Company | Bicyclic cyclohexylamines and their use as nmda receptor antagonists |
| JP2004516295A (ja) | 2000-12-21 | 2004-06-03 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | サブタイプ選択的なｎ−メチル−ｄ−アスパラギン酸拮抗薬としてのピペリジン誘導体 |
| MXPA02002749A (es) | 2001-03-27 | 2002-10-28 | Warner Lambert Co | Derivados de ciclohexilamina como antagonistas del subtipo selectivo del n-metil-d-aspartato. |
| DE10248067A1 (de) * | 2002-10-07 | 2004-04-15 | Proteosys Ag | Heteroarylpropyl-Piperazine und Heteroarylpropyl-Piperidine |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| WO2008055945A1 (en) | 2006-11-09 | 2008-05-15 | Probiodrug Ag | 3-hydr0xy-1,5-dihydr0-pyrr0l-2-one derivatives as inhibitors of glutaminyl cyclase for the treatment of ulcer, cancer and other diseases |
| ATE554085T1 (de) | 2006-11-30 | 2012-05-15 | Probiodrug Ag | Neue inhibitoren von glutaminylcyclase |
| EP2117540A1 (en) | 2007-03-01 | 2009-11-18 | Probiodrug AG | New use of glutaminyl cyclase inhibitors |
| JP5667440B2 (ja) | 2007-04-18 | 2015-02-12 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのチオ尿素誘導体 |
| SG178953A1 (en) | 2009-09-11 | 2012-04-27 | Probiodrug Ag | Heterocylcic derivatives as inhibitors of glutaminyl cyclase |
| KR20120107993A (ko) * | 2009-12-15 | 2012-10-04 | 뉴롭, 인코포레이티드 | 신경계 장애의 치료를 위한 화합물 |
| US9181233B2 (en) | 2010-03-03 | 2015-11-10 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| AU2011226074B2 (en) | 2010-03-10 | 2015-01-22 | Vivoryon Therapeutics N.V. | Heterocyclic inhibitors of glutaminyl cyclase (QC, EC 2.3.2.5) |
| US8541596B2 (en) | 2010-04-21 | 2013-09-24 | Probiodrug Ag | Inhibitors |
| CN102133198B (zh) * | 2011-03-09 | 2012-02-08 | 北京四环科宝制药有限公司 | 一种酒石酸艾芬地尔冻干粉针剂及其制备方法 |
| ES2570167T3 (es) | 2011-03-16 | 2016-05-17 | Probiodrug Ag | Derivados de benzimidazol como inhibidores de glutaminil ciclasa |
| CN103965188A (zh) * | 2013-01-29 | 2014-08-06 | 中山大学 | 含硒多奈哌齐类似物 |
| SG11201708190UA (en) | 2015-04-29 | 2017-11-29 | Janssen Pharmaceutica Nv | Azabenzimidazoles and their use as ampa receptor modulators |
| CN107750250B (zh) * | 2015-04-29 | 2021-09-07 | 詹森药业有限公司 | 吲哚酮化合物及其作为ampa受体调节剂的用途 |
| ES2812698T3 (es) | 2017-09-29 | 2021-03-18 | Probiodrug Ag | Inhibidores de glutaminil ciclasa |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH17194A (en) | 1980-03-06 | 1984-06-19 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives,and pharmaceutical composition containing the same |
| TW281670B (ja) | 1993-09-02 | 1996-07-21 | Hoffmann La Roche | |
| FR2717810B1 (fr) * | 1994-03-22 | 1996-04-26 | Adir | Nouvelles aminoalkyl benzoxazolinones et benzothiazolinones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| AU3138595A (en) * | 1994-07-20 | 1996-02-16 | Acea Pharmaceuticals, Inc. | Haloperidol analogs and the use thereof |
| ES2128629T3 (es) | 1994-10-31 | 1999-05-16 | Merck Patent Gmbh | Derivados de bencilpiperidina con afinidad elevada a puntos de enlace de receptores de aminoacidos. |
| ZA9610745B (en) * | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| DE19643790A1 (de) | 1996-10-30 | 1998-05-07 | Merck Patent Gmbh | Benzoxazol-Derivat |
-
1998
- 1998-03-20 DE DE19812331A patent/DE19812331A1/de not_active Withdrawn
-
1999
- 1999-03-11 KR KR1020007010387A patent/KR20010042047A/ko not_active Application Discontinuation
- 1999-03-11 EP EP99915568A patent/EP1068202B1/de not_active Expired - Lifetime
- 1999-03-11 AT AT99915568T patent/ATE416173T1/de not_active IP Right Cessation
- 1999-03-11 SK SK1369-2000A patent/SK13692000A3/sk unknown
- 1999-03-11 US US09/646,185 patent/US6548516B1/en not_active Expired - Fee Related
- 1999-03-11 RU RU2000126475/04A patent/RU2217429C2/ru not_active IP Right Cessation
- 1999-03-11 DK DK99915568T patent/DK1068202T3/da active
- 1999-03-11 CN CN99804190A patent/CN1123571C/zh not_active Expired - Fee Related
- 1999-03-11 PL PL99342732A patent/PL342732A1/xx not_active Application Discontinuation
- 1999-03-11 CA CA002324339A patent/CA2324339C/en not_active Expired - Fee Related
- 1999-03-11 AU AU34105/99A patent/AU747900B2/en not_active Ceased
- 1999-03-11 DE DE59914921T patent/DE59914921D1/de not_active Expired - Lifetime
- 1999-03-11 WO PCT/EP1999/001573 patent/WO1999048891A1/de not_active Application Discontinuation
- 1999-03-11 HU HU0101220A patent/HUP0101220A3/hu unknown
- 1999-03-11 JP JP2000537874A patent/JP4451565B2/ja not_active Expired - Fee Related
- 1999-03-11 PT PT99915568T patent/PT1068202E/pt unknown
- 1999-03-11 ES ES99915568T patent/ES2316184T3/es not_active Expired - Lifetime
- 1999-03-11 BR BR9908902-5A patent/BR9908902A/pt not_active IP Right Cessation
- 1999-03-11 ID IDW20002091A patent/ID26125A/id unknown
- 1999-03-18 ZA ZA9902191A patent/ZA992191B/xx unknown
- 1999-03-19 AR ARP990101208A patent/AR014747A1/es not_active Application Discontinuation
-
2000
- 2000-09-19 NO NO20004668A patent/NO20004668L/no not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2002507613A5 (ja) | ||
| JP2004521087A5 (ja) | ||
| CN103249732B (zh) | 抑制2-乙基氨甲酰氨基-1,3-苯并噻唑-5-基的细菌拓扑异构酶ii | |
| JP2006524225A5 (ja) | ||
| JP2007517010A5 (ja) | ||
| HK1156309A1 (en) | Optical isomers of an iloperidone metabolite | |
| JP2007532523A5 (ja) | ||
| TW530054B (en) | New piperazine and piperidine compounds | |
| JPH0741475A (ja) | 薬剤として有用な３−アリールカルボニル−１ｈ−インドール | |
| TW200800185A (en) | Acid secretion inhibitor | |
| RU2005134006A (ru) | Производные 4-(4-{гетероциклилалкокси}фенил0-1-(гетероциклилкарбонил)пиперидина и родственные соединения как антагонисты гистамина н3 для лечения неврологических заболеваний, таких как болезнь альцгеймера | |
| JP2003505458A5 (ja) | ||
| JP2002520323A5 (ja) | ||
| JP2007510713A5 (ja) | ||
| MXPA06002847A (es) | Derivados de pirrol con actividad antibacterial. | |
| JP2010505809A5 (ja) | ||
| JP2009518309A5 (ja) | ||
| JP2009534471A5 (ja) | ||
| TWI324601B (en) | Indol-3-yl-carbonyl-piperidin-benzoimidazol derivatives as vla receptor antagonists | |
| WO2005080378A1 (ja) | 縮合ピリダジン誘導体 | |
| JP2007533735A5 (ja) | ||
| PE20001583A1 (es) | Derivados de la 1-arenosulfonil-2-arilo-pirrolidina y de la piperidina | |
| CA2569861A1 (en) | Pyrrolidine derivatives as ccr5 antagonists | |
| NO20075022L (no) | (7-(2-(4-(3-trifluormetylfenyl)-1,2,3,6-tetrahydropyrid-1-yl)etyl) isokinolinbesylatsalt, fremstilling og terapeutiske anvendelser derav | |
| JP3911012B2 (ja) | ピロロ［２，３−ｂ］ピリジンのテトラヒドロピリジニルメチル誘導体 |