JP2003507479A5 - - Google Patents
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- Publication number
- JP2003507479A5 JP2003507479A5 JP2001518708A JP2001518708A JP2003507479A5 JP 2003507479 A5 JP2003507479 A5 JP 2003507479A5 JP 2001518708 A JP2001518708 A JP 2001518708A JP 2001518708 A JP2001518708 A JP 2001518708A JP 2003507479 A5 JP2003507479 A5 JP 2003507479A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ylmethoxy
- triazol
- triazine
- compound
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 description 26
- 150000003839 salts Chemical class 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- -1 2,5-difluorophenyl Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 4
- 0 *c([n]1c(*)nnc(*)c1n1)c1O* Chemical compound *c([n]1c(*)nnc(*)c1n1)c1O* 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical class C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- LHXGTJPZSHBDOQ-UHFFFAOYSA-N 2-[(2-ethyl-1,2,4-triazol-3-yl)methoxy]-5-methyl-8-phenyl-3-thiophen-2-ylimidazo[1,2-d][1,2,4]triazine Chemical class CCN1N=CN=C1COC1=C(C=2SC=CC=2)N2C(C)=NN=C(C=3C=CC=CC=3)C2=N1 LHXGTJPZSHBDOQ-UHFFFAOYSA-N 0.000 description 1
- YHIHRYPPOHHHMK-UHFFFAOYSA-N 2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3,8-diphenylimidazo[1,2-d][1,2,4]triazine Chemical compound CN1N=CN=C1COC1=C(C=2C=CC=CC=2)N2C=NN=C(C=3C=CC=CC=3)C2=N1 YHIHRYPPOHHHMK-UHFFFAOYSA-N 0.000 description 1
- FJIQJXGCYMQNRS-UHFFFAOYSA-N 3,8-bis(2-fluorophenyl)-5-methyl-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]imidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC=3N(N=CN=3)C)=C(C=3C(=CC=CC=3)F)N2C(C)=NN=C1C1=CC=CC=C1F FJIQJXGCYMQNRS-UHFFFAOYSA-N 0.000 description 1
- ARUDAMPSBRNTJC-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-8-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound CN1N=CN=C1COC1=C(C=2C=C(Cl)C=CC=2)N2C=NN=C(C=3C=CC=CC=3)C2=N1 ARUDAMPSBRNTJC-UHFFFAOYSA-N 0.000 description 1
- ZOOLVLQWXXSBFS-UHFFFAOYSA-N 3-cyclobutyl-5-methyl-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-8-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC=3N(N=CN=3)C)=C(C3CCC3)N2C(C)=NN=C1C1=CC=CC=C1 ZOOLVLQWXXSBFS-UHFFFAOYSA-N 0.000 description 1
- MTJBQYNQUGPVRU-UHFFFAOYSA-N 3-cyclobutyl-8-(2-fluorophenyl)-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]imidazo[1,2-d][1,2,4]triazine Chemical compound CN1N=CN=C1COC1=C(C2CCC2)N2C=NN=C(C=3C(=CC=CC=3)F)C2=N1 MTJBQYNQUGPVRU-UHFFFAOYSA-N 0.000 description 1
- XGWCOTFOOPDTGN-UHFFFAOYSA-N 3-cyclohexyl-2-[(2-ethyl-1,2,4-triazol-3-yl)methoxy]-8-(2-fluorophenyl)-5-methylimidazo[1,2-d][1,2,4]triazine Chemical compound CCN1N=CN=C1COC1=C(C2CCCCC2)N2C(C)=NN=C(C=3C(=CC=CC=3)F)C2=N1 XGWCOTFOOPDTGN-UHFFFAOYSA-N 0.000 description 1
- LXUPIFDHKGJBAW-UHFFFAOYSA-N 3-cyclohexyl-8-(2-fluorophenyl)-5-methyl-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]imidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC=3N(N=CN=3)C)=C(C3CCCCC3)N2C(C)=NN=C1C1=CC=CC=C1F LXUPIFDHKGJBAW-UHFFFAOYSA-N 0.000 description 1
- WHGGTQMVLXMBCD-UHFFFAOYSA-N 3-cyclopentyl-2-[(2-ethyl-1,2,4-triazol-3-yl)methoxy]-5-methyl-8-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound CCN1N=CN=C1COC1=C(C2CCCC2)N2C(C)=NN=C(C=3C=CC=CC=3)C2=N1 WHGGTQMVLXMBCD-UHFFFAOYSA-N 0.000 description 1
- FSDVWYAHOXAHPQ-UHFFFAOYSA-N 3-cyclopentyl-2-[(2-ethyl-1,2,4-triazol-3-yl)methoxy]-8-(2-fluorophenyl)-5-methylimidazo[1,2-d][1,2,4]triazine Chemical compound CCN1N=CN=C1COC1=C(C2CCCC2)N2C(C)=NN=C(C=3C(=CC=CC=3)F)C2=N1 FSDVWYAHOXAHPQ-UHFFFAOYSA-N 0.000 description 1
- UBFKNLMQQLKQII-UHFFFAOYSA-N 3-cyclopentyl-5-cyclopropyl-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-8-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound CN1N=CN=C1COC1=C(C2CCCC2)N2C(C3CC3)=NN=C(C=3C=CC=CC=3)C2=N1 UBFKNLMQQLKQII-UHFFFAOYSA-N 0.000 description 1
- HGCDWURHZUQNEU-UHFFFAOYSA-N 3-cyclopentyl-5-ethyl-2-[(2-ethyl-1,2,4-triazol-3-yl)methoxy]-8-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC=3N(N=CN=3)CC)=C(C3CCCC3)N2C(CC)=NN=C1C1=CC=CC=C1 HGCDWURHZUQNEU-UHFFFAOYSA-N 0.000 description 1
- JBKYVUAEDDLYBS-UHFFFAOYSA-N 3-cyclopentyl-5-ethyl-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-8-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC=3N(N=CN=3)C)=C(C3CCCC3)N2C(CC)=NN=C1C1=CC=CC=C1 JBKYVUAEDDLYBS-UHFFFAOYSA-N 0.000 description 1
- DAQGOCYPILVTSU-UHFFFAOYSA-N 3-cyclopentyl-5-methyl-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-8-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC=3N(N=CN=3)C)=C(C3CCCC3)N2C(C)=NN=C1C1=CC=CC=C1 DAQGOCYPILVTSU-UHFFFAOYSA-N 0.000 description 1
- QOQDUCLFBGWMJU-UHFFFAOYSA-N 3-cyclopentyl-8-(2-fluorophenyl)-5-methyl-2-[(1-methyl-1,2,4-triazol-3-yl)methoxy]imidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC3=NN(C)C=N3)=C(C3CCCC3)N2C(C)=NN=C1C1=CC=CC=C1F QOQDUCLFBGWMJU-UHFFFAOYSA-N 0.000 description 1
- GGUWRRKIESCOOM-UHFFFAOYSA-N 3-cyclopentyl-8-(2-fluorophenyl)-5-methyl-2-[(1-methyltriazol-4-yl)methoxy]imidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC=3N=NN(C)C=3)=C(C3CCCC3)N2C(C)=NN=C1C1=CC=CC=C1F GGUWRRKIESCOOM-UHFFFAOYSA-N 0.000 description 1
- KUTMXPLFCCEPPC-UHFFFAOYSA-N 3-cyclopentyl-8-(2-fluorophenyl)-5-methyl-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]imidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC=3N(N=CN=3)C)=C(C3CCCC3)N2C(C)=NN=C1C1=CC=CC=C1F KUTMXPLFCCEPPC-UHFFFAOYSA-N 0.000 description 1
- XNVFJKJJCMIDIX-UHFFFAOYSA-N 3-cyclopentyl-8-(2-fluorophenyl)-5-methyl-2-[(3-methyltriazol-4-yl)methoxy]imidazo[1,2-d][1,2,4]triazine Chemical compound C12=NC(OCC=3N(N=NC=3)C)=C(C3CCCC3)N2C(C)=NN=C1C1=CC=CC=C1F XNVFJKJJCMIDIX-UHFFFAOYSA-N 0.000 description 1
- PFJOUHCHTDBBED-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound CN1N=CN=C1COC1=C(C=2C=CC=CC=2)N2C=NN=C(C=3C(=CC=CC=3F)F)C2=N1 PFJOUHCHTDBBED-UHFFFAOYSA-N 0.000 description 1
- ZOTCJAZZFROEDC-UHFFFAOYSA-N 8-(2-fluorophenyl)-2-[(1-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound CN1C=NC(COC2=C(N3C=NN=C(C3=N2)C=2C(=CC=CC=2)F)C=2C=CC=CC=2)=N1 ZOTCJAZZFROEDC-UHFFFAOYSA-N 0.000 description 1
- NOIFTZSXWCKKIF-UHFFFAOYSA-N 8-(2-fluorophenyl)-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound CN1N=CN=C1COC1=C(C=2C=CC=CC=2)N2C=NN=C(C=3C(=CC=CC=3)F)C2=N1 NOIFTZSXWCKKIF-UHFFFAOYSA-N 0.000 description 1
- UZYJTQOUQUBHRB-UHFFFAOYSA-N 8-(2-fluorophenyl)-5-methyl-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenylimidazo[1,2-d][1,2,4]triazine Chemical class C12=NC(OCC=3N(N=CN=3)C)=C(C=3C=CC=CC=3)N2C(C)=NN=C1C1=CC=CC=C1F UZYJTQOUQUBHRB-UHFFFAOYSA-N 0.000 description 1
- ZOFRTHFAORVKTG-UHFFFAOYSA-N 8-(4-fluorophenyl)-2-[(2-methyl-1,2,4-triazol-3-yl)methoxy]-3-phenylimidazo[1,2-d][1,2,4]triazine Chemical compound CN1N=CN=C1COC1=C(C=2C=CC=CC=2)N2C=NN=C(C=3C=CC(F)=CC=3)C2=N1 ZOFRTHFAORVKTG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9919957.2A GB9919957D0 (en) | 1999-08-23 | 1999-08-23 | Therapeutic agents |
| GB9919957.2 | 1999-08-23 | ||
| PCT/GB2000/003199 WO2001014377A1 (en) | 1999-08-23 | 2000-08-17 | Imidazo-triazine derivatives as ligands for gaba receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003507479A JP2003507479A (ja) | 2003-02-25 |
| JP2003507479A5 true JP2003507479A5 (https=) | 2007-10-11 |
Family
ID=10859670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001518708A Withdrawn JP2003507479A (ja) | 1999-08-23 | 2000-08-17 | Ｇａｂａ受容体リガンドとしてのイミダゾ−トリアジン誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6608062B1 (https=) |
| EP (1) | EP1212324B1 (https=) |
| JP (1) | JP2003507479A (https=) |
| AT (1) | ATE253066T1 (https=) |
| AU (1) | AU775008B2 (https=) |
| CA (1) | CA2380452C (https=) |
| DE (1) | DE60006260T2 (https=) |
| ES (1) | ES2208404T3 (https=) |
| GB (1) | GB9919957D0 (https=) |
| WO (1) | WO2001014377A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9923078D0 (en) * | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| GB0210127D0 (en) * | 2002-05-02 | 2002-06-12 | Merck Sharp & Dohme | Therapeutic agents |
| AU2003252499B2 (en) * | 2002-07-12 | 2007-11-08 | Japan Science And Technology Agency | Drugs for improving the prognosis of brain injury and a method of screening the same |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| AU2006327300A1 (en) | 2005-12-20 | 2007-06-28 | Astrazeneca Ab | Substituted Cinnoline derivatives as GABAa-receptor modulators and method for their synthesis |
| US7465795B2 (en) | 2005-12-20 | 2008-12-16 | Astrazeneca Ab | Compounds and uses thereof |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| WO2007134077A2 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| EP2068872A1 (en) | 2006-09-08 | 2009-06-17 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| GB0622472D0 (en) * | 2006-11-10 | 2006-12-20 | Addex Pharmaceuticals Sa | Novel heterocyclic derivatives |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| US20240327413A1 (en) * | 2021-06-29 | 2024-10-03 | Zomagen Biosciences Ltd | Nlrp3 modulators |
| IL310992A (en) * | 2021-08-25 | 2024-04-01 | Ptc Therapeutics Inc | NLRP3 inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3422194A (en) * | 1967-08-15 | 1969-01-14 | Smithkline Corp | The treatment of depression with imidazo(1,2-b)-as-triazines and compositions thereof |
| ES2194205T3 (es) | 1996-07-25 | 2003-11-16 | Merck Sharp & Dohme | Derivados de triazolo-piridazina sustituidos como ligandos para los receptores gaba. |
| CA2346289A1 (en) * | 1998-10-16 | 2000-04-27 | Merck Sharp & Dohme Limited | Pyrazolo-triazine derivatives as ligands for gaba receptors |
-
1999
- 1999-08-23 GB GBGB9919957.2A patent/GB9919957D0/en not_active Ceased
-
2000
- 2000-08-17 CA CA002380452A patent/CA2380452C/en not_active Expired - Fee Related
- 2000-08-17 WO PCT/GB2000/003199 patent/WO2001014377A1/en not_active Ceased
- 2000-08-17 AU AU67077/00A patent/AU775008B2/en not_active Ceased
- 2000-08-17 US US10/069,437 patent/US6608062B1/en not_active Expired - Fee Related
- 2000-08-17 DE DE60006260T patent/DE60006260T2/de not_active Expired - Lifetime
- 2000-08-17 AT AT00954717T patent/ATE253066T1/de not_active IP Right Cessation
- 2000-08-17 ES ES00954717T patent/ES2208404T3/es not_active Expired - Lifetime
- 2000-08-17 JP JP2001518708A patent/JP2003507479A/ja not_active Withdrawn
- 2000-08-17 EP EP00954717A patent/EP1212324B1/en not_active Expired - Lifetime
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