CA2223936A1 - Novel substituted aryl and cycloalkyl imidazolones; a new class of gaba brain receptor ligands - Google Patents
Novel substituted aryl and cycloalkyl imidazolones; a new class of gaba brain receptor ligandsInfo
- Publication number
- CA2223936A1 CA2223936A1 CA002223936A CA2223936A CA2223936A1 CA 2223936 A1 CA2223936 A1 CA 2223936A1 CA 002223936 A CA002223936 A CA 002223936A CA 2223936 A CA2223936 A CA 2223936A CA 2223936 A1 CA2223936 A1 CA 2223936A1
- Authority
- CA
- Canada
- Prior art keywords
- optionally substituted
- substituted aryl
- imidazolones
- cycloalkyl
- new class
- 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
- 210000004556 brain Anatomy 0.000 title abstract 3
- 125000003107 substituted aryl group Chemical group 0.000 title abstract 2
- -1 cycloalkyl imidazolones Chemical class 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- 239000000556 agonist Substances 0.000 abstract 4
- 239000005557 antagonist Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 abstract 1
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 229940049706 benzodiazepine Drugs 0.000 abstract 1
- 238000003745 diagnosis Methods 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 206010015037 epilepsy Diseases 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 208000019116 sleep disease Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Disclosed are compounds of formula (I) wherein: T is NH, O, or S; X is hydrogen, hydroxyl, lower alkyl, or an optionally substituted amide; the W
ring is an optionally substituted aryl or heteroaryl group; and (a) represents an optionally substituted benzo group or an optionally substituted 5, 6, 7, or 8 membered ring. These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compouns are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.
ring is an optionally substituted aryl or heteroaryl group; and (a) represents an optionally substituted benzo group or an optionally substituted 5, 6, 7, or 8 membered ring. These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compouns are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/461,641 | 1995-06-05 | ||
| US08/462,674 US5637725A (en) | 1995-06-05 | 1995-06-05 | Substituted aryl and cycloalkyl imidazolones; a new class of GABA brain receptor ligands |
| US08/461,641 US5637724A (en) | 1995-06-05 | 1995-06-05 | Substituted aryl and cycloalkyl imidazolones; a new class of GABA brain receptor ligands |
| US08/462,674 | 1995-06-05 | ||
| PCT/US1996/010214 WO1996039404A1 (en) | 1995-06-05 | 1996-06-04 | Novel substituted aryl and cycloalkyl imidazolones; a new class of gaba brain receptor ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2223936A1 true CA2223936A1 (en) | 1996-12-12 |
| CA2223936C CA2223936C (en) | 2004-01-20 |
Family
ID=27040073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002223936A Expired - Fee Related CA2223936C (en) | 1995-06-05 | 1996-06-04 | Novel substituted aryl and cycloalkyl imidazolones; a new class of gaba brain receptor ligands |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0830359A1 (en) |
| AU (1) | AU717630B2 (en) |
| CA (1) | CA2223936C (en) |
| WO (1) | WO1996039404A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6271241B1 (en) | 1999-04-02 | 2001-08-07 | Neurogen Corporation | Cycloalkyl and aryl fused aminoalkyl-imidazole derivatives: modulators and GLP-1 receptors |
| US6380210B1 (en) | 1999-04-02 | 2002-04-30 | Neurogen Corporation | Heteroaryl fused aminoalkyl-imidazole derivatives: selective modulators of GABAa receptors |
| US6281237B1 (en) | 1999-04-02 | 2001-08-28 | Neurogen Corporation | N-phenyl benzimidazolecarboxamide and N-phenyl indolecarboxamide derivatives |
| US6627624B1 (en) | 1999-04-02 | 2003-09-30 | Neurogen Corporation | Aryl fused aminoalkyl-imidazole derivatives: selective modulators of GABAa receptors |
| EP1506194B1 (en) * | 2002-05-17 | 2006-07-19 | Neurogen Corporation | SUBSTITUTED RING-FUSED IMIDAZOLE DERIVATES: GABA sb A /sb RECEPTOR LIGANDS |
| GB0401334D0 (en) * | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57149277A (en) * | 1981-03-10 | 1982-09-14 | Taiho Yakuhin Kogyo Kk | Heterocyclic compound |
| US5484944A (en) * | 1993-10-27 | 1996-01-16 | Neurogen Corporation | Certain fused pyrrolecarboxanilides and their use as GABA brain receptor ligands |
-
1996
- 1996-06-04 WO PCT/US1996/010214 patent/WO1996039404A1/en not_active Application Discontinuation
- 1996-06-04 CA CA002223936A patent/CA2223936C/en not_active Expired - Fee Related
- 1996-06-04 EP EP96919393A patent/EP0830359A1/en not_active Ceased
- 1996-06-04 AU AU61743/96A patent/AU717630B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA2223936C (en) | 2004-01-20 |
| WO1996039404A1 (en) | 1996-12-12 |
| EP0830359A1 (en) | 1998-03-25 |
| AU6174396A (en) | 1996-12-24 |
| AU717630B2 (en) | 2000-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |