JP2005531548A5 - - Google Patents
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- Publication number
- JP2005531548A5 JP2005531548A5 JP2004501402A JP2004501402A JP2005531548A5 JP 2005531548 A5 JP2005531548 A5 JP 2005531548A5 JP 2004501402 A JP2004501402 A JP 2004501402A JP 2004501402 A JP2004501402 A JP 2004501402A JP 2005531548 A5 JP2005531548 A5 JP 2005531548A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazol
- compound
- alkyl
- ylmethyl
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 36
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 10
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 10
- 102000005962 receptors Human genes 0.000 claims 10
- 108020003175 receptors Proteins 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 210000004027 cell Anatomy 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 230000036506 anxiety Effects 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 238000003556 assay Methods 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 208000000044 Amnesia Diseases 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 230000007831 electrophysiology Effects 0.000 claims 2
- 238000002001 electrophysiology Methods 0.000 claims 2
- 238000001727 in vivo Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- HPCAKADYVSJDJP-UHFFFAOYSA-N 1-ethyl-2-[[2-(2-fluorophenyl)imidazol-1-yl]methyl]-4,5-dimethylimidazole Chemical compound CCN1C(C)=C(C)N=C1CN1C(C=2C(=CC=CC=2)F)=NC=C1 HPCAKADYVSJDJP-UHFFFAOYSA-N 0.000 claims 1
- XFWMPCMTKXSJSR-UHFFFAOYSA-N 2-[1-[(1-ethyl-4,5-dimethylimidazol-2-yl)methyl]imidazol-2-yl]-6-fluoropyridine Chemical compound CCN1C(C)=C(C)N=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 XFWMPCMTKXSJSR-UHFFFAOYSA-N 0.000 claims 1
- DYNWIZJCHWKHGS-UHFFFAOYSA-N 2-[1-[(1-ethyl-4-methyl-5-pyridin-2-ylimidazol-2-yl)methyl]imidazol-2-yl]-6-fluoropyridine Chemical compound N=1C(C)=C(C=2N=CC=CC=2)N(CC)C=1CN1C=CN=C1C1=CC=CC(F)=N1 DYNWIZJCHWKHGS-UHFFFAOYSA-N 0.000 claims 1
- QRDCXSFYOJRCPT-UHFFFAOYSA-N 2-[1-[(1-ethyl-5-methyl-4-pyridin-2-ylimidazol-2-yl)methyl]imidazol-2-yl]-6-fluoropyridine Chemical compound CCN1C(C)=C(C=2N=CC=CC=2)N=C1CN1C=CN=C1C1=CC=CC(F)=N1 QRDCXSFYOJRCPT-UHFFFAOYSA-N 0.000 claims 1
- BBPRTYKQAOSOML-UHFFFAOYSA-N 2-[1-[(1-ethylimidazol-2-yl)methyl]imidazol-2-yl]-6-fluoropyridine Chemical compound CCN1C=CN=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 BBPRTYKQAOSOML-UHFFFAOYSA-N 0.000 claims 1
- RDSQEZKEKDPRBE-UHFFFAOYSA-N 2-[1-[(4-bromo-1-ethyl-5-methylimidazol-2-yl)methyl]imidazol-2-yl]-6-fluoropyridine Chemical compound CCN1C(C)=C(Br)N=C1CN1C(C=2N=C(F)C=CC=2)=NC=C1 RDSQEZKEKDPRBE-UHFFFAOYSA-N 0.000 claims 1
- RBPDNWBEEOPYSE-UHFFFAOYSA-N 2-[1-[(5-bromo-1-ethyl-4-methylimidazol-2-yl)methyl]imidazol-2-yl]-6-fluoropyridine Chemical compound CC1=C(Br)N(CC)C(CN2C(=NC=C2)C=2N=C(F)C=CC=2)=N1 RBPDNWBEEOPYSE-UHFFFAOYSA-N 0.000 claims 1
- LZCJGXYFHRNLHU-UHFFFAOYSA-N 2-[1-[[1-ethyl-4-methyl-5-[3-(trifluoromethyl)phenyl]imidazol-2-yl]methyl]imidazol-2-yl]-6-fluoropyridine Chemical compound N=1C(C)=C(C=2C=C(C=CC=2)C(F)(F)F)N(CC)C=1CN1C=CN=C1C1=CC=CC(F)=N1 LZCJGXYFHRNLHU-UHFFFAOYSA-N 0.000 claims 1
- FKPCHZMFNINGLC-UHFFFAOYSA-N 2-[1-[[1-ethyl-5-methyl-4-[3-(trifluoromethyl)phenyl]imidazol-2-yl]methyl]imidazol-2-yl]-6-fluoropyridine Chemical compound CCN1C(C)=C(C=2C=C(C=CC=2)C(F)(F)F)N=C1CN1C=CN=C1C1=CC=CC(F)=N1 FKPCHZMFNINGLC-UHFFFAOYSA-N 0.000 claims 1
- RYHRWTNDRXHMRA-UHFFFAOYSA-N 2-[[2-(1,4-difluorocyclohexa-2,4-dien-1-yl)imidazol-1-yl]methyl]-1-ethyl-4,5-dimethylimidazole Chemical compound CCN1C(C)=C(C)N=C1CN1C(C2(F)C=CC(F)=CC2)=NC=C1 RYHRWTNDRXHMRA-UHFFFAOYSA-N 0.000 claims 1
- WVFQBUHUZNJMGE-UHFFFAOYSA-N 2-[[2-(1,4-difluorocyclohexa-2,4-dien-1-yl)imidazol-1-yl]methyl]-1-ethyl-4-methyl-5-phenylimidazole Chemical compound N=1C(C)=C(C=2C=CC=CC=2)N(CC)C=1CN1C=CN=C1C1(F)CC=C(F)C=C1 WVFQBUHUZNJMGE-UHFFFAOYSA-N 0.000 claims 1
- DXTYUTJTYAVECT-UHFFFAOYSA-N 2-[[2-(1,4-difluorocyclohexa-2,4-dien-1-yl)imidazol-1-yl]methyl]-1-ethyl-5-methyl-4-phenylimidazole Chemical compound CCN1C(C)=C(C=2C=CC=CC=2)N=C1CN1C=CN=C1C1(F)CC=C(F)C=C1 DXTYUTJTYAVECT-UHFFFAOYSA-N 0.000 claims 1
- UCNFLXKNUAWUSD-UHFFFAOYSA-N 2-[[2-(1,4-difluorocyclohexa-2,4-dien-1-yl)imidazol-1-yl]methyl]-4,5-dimethyl-1-propylimidazole Chemical compound CCCN1C(C)=C(C)N=C1CN1C(C2(F)C=CC(F)=CC2)=NC=C1 UCNFLXKNUAWUSD-UHFFFAOYSA-N 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 230000006399 behavior Effects 0.000 claims 1
- 210000001124 body fluid Anatomy 0.000 claims 1
- 239000010839 body fluid Substances 0.000 claims 1
- 210000004958 brain cell Anatomy 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000013583 drug formulation Substances 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- -1 nitro, cyano, amino Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000006403 short-term memory Effects 0.000 claims 1
- 230000007781 signaling event Effects 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 0 **c1c(*)[n](*)c(C[n]2c(*)ncc2)n1 Chemical compound **c1c(*)[n](*)c(C[n]2c(*)ncc2)n1 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37782002P | 2002-05-02 | 2002-05-02 | |
| PCT/US2003/013855 WO2003093263A1 (en) | 2002-05-02 | 2003-05-02 | Substituted imidazole derivatives: gabaa receptor ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005531548A JP2005531548A (ja) | 2005-10-20 |
| JP2005531548A5 true JP2005531548A5 (enExample) | 2006-07-27 |
Family
ID=29401570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004501402A Pending JP2005531548A (ja) | 2002-05-02 | 2003-05-02 | 置換イミダゾール誘導体：ｇａｂａａ受容体リガンド |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7030144B2 (enExample) |
| EP (1) | EP1499608A1 (enExample) |
| JP (1) | JP2005531548A (enExample) |
| AU (1) | AU2003245259A1 (enExample) |
| CA (1) | CA2485093A1 (enExample) |
| WO (1) | WO2003093263A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2278345T3 (es) * | 2003-07-25 | 2007-08-01 | Neurogen Corporation | Imidazo-pirimidinas y triazolo-pirimidinas: ligandos de receptores de benzodiazepinas. |
| US20050187277A1 (en) * | 2004-02-12 | 2005-08-25 | Mjalli Adnan M. | Substituted azole derivatives, compositions, and methods of use |
| JP4836280B2 (ja) * | 2004-06-18 | 2011-12-14 | ノバルティス バクシンズ アンド ダイアグノスティックス，インコーポレーテッド | 癌を治療するためのキネシンスピンドルタンパク質（ｋｓｐ）阻害剤としてのｎ−（１−（１−ベンジル−４−フェニル−１ｈ−イミダゾール−２−イル）−２，２−ジメチルプロピル）ベンズアミド誘導体および関連化合物 |
| US8030339B2 (en) | 2005-10-14 | 2011-10-04 | Neurosearch A/S | Imidazole derivatives for the treatment of anxiety and related diseases |
| US8362265B2 (en) * | 2006-05-05 | 2013-01-29 | Dow Global Technologies, Llc | Hafnium complexes of heterocyclic organic ligands |
| JP2010515687A (ja) | 2007-01-05 | 2010-05-13 | ノバルティス アーゲー | キネシンスピンドルタンパク質阻害剤（ｅｇ−５）としてのイミダゾール誘導体 |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637725A (en) | 1995-06-05 | 1997-06-10 | Neurogen Corporation | Substituted aryl and cycloalkyl imidazolones; a new class of GABA brain receptor ligands |
| AU2001270297A1 (en) | 2000-06-30 | 2002-01-14 | Neurogen Corporation | 2-phenylimidazo(1,2-a)pyridine derivatives: a new class of gaba brain receptor ligands |
| PA8535601A1 (es) | 2000-12-21 | 2002-11-28 | Pfizer | Derivados benzimidazol y piridilimidazol como ligandos para gabaa |
| US6610723B2 (en) * | 2001-01-29 | 2003-08-26 | Hoffmann-La Roche Inc. | Imidazole derivatives |
-
2003
- 2003-05-02 AU AU2003245259A patent/AU2003245259A1/en not_active Abandoned
- 2003-05-02 JP JP2004501402A patent/JP2005531548A/ja active Pending
- 2003-05-02 US US10/429,056 patent/US7030144B2/en not_active Expired - Fee Related
- 2003-05-02 WO PCT/US2003/013855 patent/WO2003093263A1/en not_active Ceased
- 2003-05-02 CA CA002485093A patent/CA2485093A1/en not_active Abandoned
- 2003-05-02 EP EP03738896A patent/EP1499608A1/en not_active Withdrawn
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