JP2002506069A5 - - Google Patents
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- Publication number
- JP2002506069A5 JP2002506069A5 JP2000535638A JP2000535638A JP2002506069A5 JP 2002506069 A5 JP2002506069 A5 JP 2002506069A5 JP 2000535638 A JP2000535638 A JP 2000535638A JP 2000535638 A JP2000535638 A JP 2000535638A JP 2002506069 A5 JP2002506069 A5 JP 2002506069A5
- Authority
- JP
- Japan
- Prior art keywords
- fluorophenyl
- ethyl
- imidazolidinone
- methyltetrazol
- indole
- 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.)
- Pending
Links
- -1 2-thiazolyl Chemical group 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 230000000561 anti-psychotic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 description 1
- LSOSTOVOMJGNDT-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(1-methylpiperidin-4-yl)-5-(2-methyltetrazol-5-yl)indole Chemical compound C1CN(C)CCC1C(C1=CC(=CC=C11)C2=NN(C)N=N2)=CN1C1=CC=C(F)C=C1 LSOSTOVOMJGNDT-UHFFFAOYSA-N 0.000 description 1
- WKUWMRSBCPGSSX-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-(1-methyltetrazol-5-yl)indol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]imidazolidin-2-one Chemical compound CN1N=NN=C1C1=CC=C(N(C=C2C=3CCN(CCN4C(NCC4)=O)CC=3)C=3C=CC(F)=CC=3)C2=C1 WKUWMRSBCPGSSX-UHFFFAOYSA-N 0.000 description 1
- AFXURDNNJQAATH-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-(1-methyltriazol-4-yl)indol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]imidazolidin-2-one Chemical compound N1=NN(C)C=C1C1=CC=C(N(C=C2C=3CCN(CCN4C(NCC4)=O)CC=3)C=3C=CC(F)=CC=3)C2=C1 AFXURDNNJQAATH-UHFFFAOYSA-N 0.000 description 1
- POOTULJXWQPYPW-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-(2-methyltetrazol-5-yl)indol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]imidazolidin-2-one Chemical compound CN1N=NC(C=2C=C3C(C=4CCN(CCN5C(NCC5)=O)CC=4)=CN(C3=CC=2)C=2C=CC(F)=CC=2)=N1 POOTULJXWQPYPW-UHFFFAOYSA-N 0.000 description 1
- USCDVFNXTCISHV-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-(2-methyltetrazol-5-yl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one Chemical compound CN1N=NC(C=2C=C3C(C4CCN(CCN5C(NCC5)=O)CC4)=CN(C3=CC=2)C=2C=CC(F)=CC=2)=N1 USCDVFNXTCISHV-UHFFFAOYSA-N 0.000 description 1
- HQYPFANIKHYLAR-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-(2-methyltriazol-4-yl)indol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]imidazolidin-2-one Chemical compound CN1N=CC(C=2C=C3C(C=4CCN(CCN5C(NCC5)=O)CC=4)=CN(C3=CC=2)C=2C=CC(F)=CC=2)=N1 HQYPFANIKHYLAR-UHFFFAOYSA-N 0.000 description 1
- WSVJLBOEXBDQNC-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-(2h-tetrazol-5-yl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(C3=NNN=N3)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 WSVJLBOEXBDQNC-UHFFFAOYSA-N 0.000 description 1
- NNJVTZUCDUKFNU-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-[(1-methyltetrazol-5-yl)methyl]indol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]imidazolidin-2-one Chemical compound CN1N=NN=C1CC1=CC=C(N(C=C2C=3CCN(CCN4C(NCC4)=O)CC=3)C=3C=CC(F)=CC=3)C2=C1 NNJVTZUCDUKFNU-UHFFFAOYSA-N 0.000 description 1
- XCVQLIQAAOSBFQ-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-[(1-methyltetrazol-5-yl)methyl]indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one Chemical compound CN1N=NN=C1CC1=CC=C(N(C=C2C3CCN(CCN4C(NCC4)=O)CC3)C=3C=CC(F)=CC=3)C2=C1 XCVQLIQAAOSBFQ-UHFFFAOYSA-N 0.000 description 1
- WLHBDAQKWPIGFJ-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-[(2-methyltetrazol-5-yl)methyl]indol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]imidazolidin-2-one Chemical compound CN1N=NC(CC=2C=C3C(C=4CCN(CCN5C(NCC5)=O)CC=4)=CN(C3=CC=2)C=2C=CC(F)=CC=2)=N1 WLHBDAQKWPIGFJ-UHFFFAOYSA-N 0.000 description 1
- FGHKCRNDQSRICR-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-[(2-methyltetrazol-5-yl)methyl]indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one Chemical compound CN1N=NC(CC=2C=C3C(C4CCN(CCN5C(NCC5)=O)CC4)=CN(C3=CC=2)C=2C=CC(F)=CC=2)=N1 FGHKCRNDQSRICR-UHFFFAOYSA-N 0.000 description 1
- NEFOVKCNIRHKNI-UHFFFAOYSA-N 1-[2-[4-[5-(2-ethyltetrazol-5-yl)-1-(4-fluorophenyl)indol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]imidazolidin-2-one Chemical compound CCN1N=NC(C=2C=C3C(C=4CCN(CCN5C(NCC5)=O)CC=4)=CN(C3=CC=2)C=2C=CC(F)=CC=2)=N1 NEFOVKCNIRHKNI-UHFFFAOYSA-N 0.000 description 1
- VAVQOXVIBXPIJO-UHFFFAOYSA-N 1-[2-[4-[5-(2-ethyltriazol-4-yl)-1-(4-fluorophenyl)indol-3-yl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]imidazolidin-2-one Chemical compound CCN1N=CC(C=2C=C3C(C=4CCN(CCN5C(NCC5)=O)CC=4)=CN(C3=CC=2)C=2C=CC(F)=CC=2)=N1 VAVQOXVIBXPIJO-UHFFFAOYSA-N 0.000 description 1
- NEBSYJAENXRLFM-UHFFFAOYSA-N 1-[2-[4-[5-(2-ethyltriazol-4-yl)-1-(4-fluorophenyl)indol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one Chemical compound CCN1N=CC(C=2C=C3C(C4CCN(CCN5C(NCC5)=O)CC4)=CN(C3=CC=2)C=2C=CC(F)=CC=2)=N1 NEBSYJAENXRLFM-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 108060003345 Adrenergic Receptor Proteins 0.000 description 1
- 102000017910 Adrenergic receptor Human genes 0.000 description 1
- HBPSRCYVMVJFFG-UHFFFAOYSA-N CN1N=C(N=N1)C2=CC3=C(C=C2)N(C=C3C4=CCN(CC4)CCN5CCNC5=O)C6CCNCC6 Chemical compound CN1N=C(N=N1)C2=CC3=C(C=C2)N(C=C3C4=CCN(CC4)CCN5CCNC5=O)C6CCNCC6 HBPSRCYVMVJFFG-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK31898 | 1998-03-09 | ||
| DK0318/98 | 1998-03-09 | ||
| PCT/DK1999/000119 WO1999046259A1 (en) | 1998-03-09 | 1999-03-09 | 5-heteroaryl substituted indoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002506069A JP2002506069A (ja) | 2002-02-26 |
| JP2002506069A5 true JP2002506069A5 (https=) | 2006-03-23 |
Family
ID=8092210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000535638A Pending JP2002506069A (ja) | 1998-03-09 | 1999-03-09 | ５−ヘテロアリール置換されたインドール類 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6602889B1 (https=) |
| EP (1) | EP1068198B1 (https=) |
| JP (1) | JP2002506069A (https=) |
| AR (1) | AR016184A1 (https=) |
| AT (1) | ATE241615T1 (https=) |
| AU (1) | AU2713399A (https=) |
| DE (1) | DE69908330T2 (https=) |
| DK (1) | DK1068198T3 (https=) |
| ES (1) | ES2199553T3 (https=) |
| PT (1) | PT1068198E (https=) |
| WO (1) | WO1999046259A1 (https=) |
| ZA (1) | ZA991893B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60009932T2 (de) | 1999-09-09 | 2005-04-14 | H. Lundbeck A/S | 5-aminoalkyl- und 5-aminocarbonylsubstituierte indole |
| WO2001078723A1 (en) * | 2000-04-12 | 2001-10-25 | Smithkline Beecham Corporation | Compounds and methods |
| DE10121217A1 (de) | 2001-04-30 | 2002-10-31 | Merck Patent Gmbh | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
| EP1478643A1 (en) * | 2002-02-22 | 2004-11-24 | H. Lundbeck A/S | 5-heteroaryl substituted indoles |
| ATE531706T1 (de) * | 2005-04-30 | 2011-11-15 | Boehringer Ingelheim Int | Neue piperidin-substituierte indole und ihre verwendung als ccr-3-modulatoren |
| US8293781B2 (en) | 2007-03-29 | 2012-10-23 | Daiichi Sankyo Company, Limited | Indole derivatives having cPLA2 inhibiting activity and applications and production methods of the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5322851A (en) * | 1990-07-02 | 1994-06-21 | H. Lundbeck A/S | Indole derivatives |
| US5317103A (en) | 1991-01-15 | 1994-05-31 | Merck Sharp & Dohme Limited | Indole-substituted five-membered heteroaromatic compounds as 5-HT1 agonists |
| CZ283018B6 (cs) * | 1991-02-01 | 1997-12-17 | Merck Sharp And Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi |
| TW263508B (https=) * | 1991-02-12 | 1995-11-21 | Pfizer | |
| JPH05505612A (ja) | 1991-03-01 | 1993-08-19 | ハー・ルンドベック・アクティーゼルスカブ | 高血圧症及び末梢血管疾患の治療法 |
| IL106445A (en) * | 1992-07-30 | 1998-01-04 | Merck Sharp & Dohme | History of 1,2,4-Trans-Triazole 4-Transform, Preparation and Pharmaceutical Preparations Containing Them |
-
1999
- 1999-03-09 WO PCT/DK1999/000119 patent/WO1999046259A1/en not_active Ceased
- 1999-03-09 DE DE69908330T patent/DE69908330T2/de not_active Expired - Fee Related
- 1999-03-09 DK DK99907330T patent/DK1068198T3/da active
- 1999-03-09 ES ES99907330T patent/ES2199553T3/es not_active Expired - Lifetime
- 1999-03-09 AU AU27133/99A patent/AU2713399A/en not_active Abandoned
- 1999-03-09 PT PT99907330T patent/PT1068198E/pt unknown
- 1999-03-09 ZA ZA9901893A patent/ZA991893B/xx unknown
- 1999-03-09 US US09/623,232 patent/US6602889B1/en not_active Expired - Fee Related
- 1999-03-09 AR ARP990100993A patent/AR016184A1/es active IP Right Grant
- 1999-03-09 EP EP99907330A patent/EP1068198B1/en not_active Expired - Lifetime
- 1999-03-09 JP JP2000535638A patent/JP2002506069A/ja active Pending
- 1999-03-09 AT AT99907330T patent/ATE241615T1/de not_active IP Right Cessation
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