MX2007010991A - Agentes que modulan el canal de potasio y su uso medico. - Google Patents
Agentes que modulan el canal de potasio y su uso medico.Info
- Publication number
- MX2007010991A MX2007010991A MX2007010991A MX2007010991A MX2007010991A MX 2007010991 A MX2007010991 A MX 2007010991A MX 2007010991 A MX2007010991 A MX 2007010991A MX 2007010991 A MX2007010991 A MX 2007010991A MX 2007010991 A MX2007010991 A MX 2007010991A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- pyrazol
- quinazolin
- amine
- dimethyl
- Prior art date
Links
- 102000004257 Potassium Channel Human genes 0.000 title claims abstract description 25
- 108020001213 potassium channel Proteins 0.000 title claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 title abstract description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 52
- 201000010099 disease Diseases 0.000 claims abstract description 31
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- -1 cyano, nitro, amino, methylenedioxy, phenyl Chemical group 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 68
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- LZNOABFJNNIWJV-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)quinazoline Chemical class N1C=CC(C=2N=C3C=CC=CC3=CN=2)=N1 LZNOABFJNNIWJV-UHFFFAOYSA-N 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000002837 carbocyclic group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 23
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 23
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 23
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 125000002950 monocyclic group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 125000002757 morpholinyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000003367 polycyclic group Chemical group 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 201000001881 impotence Diseases 0.000 claims description 6
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- GOZZRZJXLZRECQ-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(3-methoxyphenyl)quinazolin-4-amine Chemical compound COC1=CC=CC(NC=2C3=CC=CC=C3N=C(N=2)N2C(=CC(C)=N2)C)=C1 GOZZRZJXLZRECQ-UHFFFAOYSA-N 0.000 claims description 4
- UIEWRXCGQHKNHE-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(4-iodophenyl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=CC(I)=CC=2)=C(C=CC=C2)C2=N1 UIEWRXCGQHKNHE-UHFFFAOYSA-N 0.000 claims description 4
- SYZRMPMKRDRKNP-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(4-methylphenyl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 SYZRMPMKRDRKNP-UHFFFAOYSA-N 0.000 claims description 4
- KJHCUZKDFBIUMP-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(4-phenylphenyl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 KJHCUZKDFBIUMP-UHFFFAOYSA-N 0.000 claims description 4
- KHCBXUXAEDEPHQ-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-naphthalen-2-ylquinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=C3C=CC=CC3=CC=2)=C(C=CC=C2)C2=N1 KHCBXUXAEDEPHQ-UHFFFAOYSA-N 0.000 claims description 4
- GLWUGSGVMNPFLG-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-phenylquinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=CC=CC=2)=C(C=CC=C2)C2=N1 GLWUGSGVMNPFLG-UHFFFAOYSA-N 0.000 claims description 4
- SSYGPRANWVMMMM-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-quinolin-8-ylquinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C3=NC=CC=C3C=CC=2)=C(C=CC=C2)C2=N1 SSYGPRANWVMMMM-UHFFFAOYSA-N 0.000 claims description 4
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- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- XRENJEYJRMYBJG-UHFFFAOYSA-N n-(2-chlorophenyl)-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C(=CC=CC=2)Cl)=C(C=CC=C2)C2=N1 XRENJEYJRMYBJG-UHFFFAOYSA-N 0.000 claims description 4
- DMXDSQCPDWYXEG-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=C(Cl)C(Cl)=CC=2)=C(C=CC=C2)C2=N1 DMXDSQCPDWYXEG-UHFFFAOYSA-N 0.000 claims description 4
- GSGGDGRMJIJMCL-UHFFFAOYSA-N n-(3-chlorophenyl)-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=C(Cl)C=CC=2)=C(C=CC=C2)C2=N1 GSGGDGRMJIJMCL-UHFFFAOYSA-N 0.000 claims description 4
- ITFQWXZRHMHPKI-UHFFFAOYSA-N n-(4-bromophenyl)-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=CC(Br)=CC=2)=C(C=CC=C2)C2=N1 ITFQWXZRHMHPKI-UHFFFAOYSA-N 0.000 claims description 4
- RUYWKBFOCUBMAM-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=CC(Cl)=CC=2)=C(C=CC=C2)C2=N1 RUYWKBFOCUBMAM-UHFFFAOYSA-N 0.000 claims description 4
- 208000018198 spasticity Diseases 0.000 claims description 4
- PWWHIMGVYIKMCS-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(2-methylphenyl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C(=CC=CC=2)C)=C(C=CC=C2)C2=N1 PWWHIMGVYIKMCS-UHFFFAOYSA-N 0.000 claims description 3
- FBLLMHHCBDVLOE-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-[4-(trifluoromethyl)phenyl]quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=C(C=CC=C2)C2=N1 FBLLMHHCBDVLOE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
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- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- LUMKJCXWGTXDCT-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-4-piperidin-1-ylquinazoline Chemical compound N1=C(C)C=C(C)N1C1=NC(N2CCCCC2)=C(C=CC=C2)C2=N1 LUMKJCXWGTXDCT-UHFFFAOYSA-N 0.000 claims description 2
- LNHADOZOBGZFKT-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(1,2,3,4-tetrahydronaphthalen-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2C3=CC=CC=C3CCC2)=C(C=CC=C2)C2=N1 LNHADOZOBGZFKT-UHFFFAOYSA-N 0.000 claims description 2
- BKQMFIBJLHPXCS-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(2-pyrrolidin-1-ylethyl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NCCN2CCCC2)=C(C=CC=C2)C2=N1 BKQMFIBJLHPXCS-UHFFFAOYSA-N 0.000 claims description 2
- FTZNQMOFFXWZHS-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(3-methylphenyl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=C(C)C=CC=2)=C(C=CC=C2)C2=N1 FTZNQMOFFXWZHS-UHFFFAOYSA-N 0.000 claims description 2
- GLNRXTYBCPVBGP-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(furan-2-ylmethyl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NCC=2OC=CC=2)=C(C=CC=C2)C2=N1 GLNRXTYBCPVBGP-UHFFFAOYSA-N 0.000 claims description 2
- UQZOFDWFOMNJHI-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(oxan-4-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2CCOCC2)=C(C=CC=C2)C2=N1 UQZOFDWFOMNJHI-UHFFFAOYSA-N 0.000 claims description 2
- JQQXFPDPXCINPK-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(thiophen-2-ylmethyl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NCC=2SC=CC=2)=C(C=CC=C2)C2=N1 JQQXFPDPXCINPK-UHFFFAOYSA-N 0.000 claims description 2
- RGODJLANPPMVSR-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-[3-(trifluoromethyl)phenyl]quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=C(C=CC=2)C(F)(F)F)=C(C=CC=C2)C2=N1 RGODJLANPPMVSR-UHFFFAOYSA-N 0.000 claims description 2
- OFUSEDFMYBGKBL-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-ethylquinazolin-4-amine Chemical compound N=1C2=CC=CC=C2C(NCC)=NC=1N1N=C(C)C=C1C OFUSEDFMYBGKBL-UHFFFAOYSA-N 0.000 claims description 2
- SWCVPLSWABSUIW-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-pentan-3-ylquinazolin-4-amine Chemical compound N=1C2=CC=CC=C2C(NC(CC)CC)=NC=1N1N=C(C)C=C1C SWCVPLSWABSUIW-UHFFFAOYSA-N 0.000 claims description 2
- HUKYQZQUKBYDEP-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-piperidin-4-ylquinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2CCNCC2)=C(C=CC=C2)C2=N1 HUKYQZQUKBYDEP-UHFFFAOYSA-N 0.000 claims description 2
- PZXBCNSEPUEPHG-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-propylquinazolin-4-amine Chemical compound N=1C2=CC=CC=C2C(NCCC)=NC=1N1N=C(C)C=C1C PZXBCNSEPUEPHG-UHFFFAOYSA-N 0.000 claims description 2
- UEKJCEWDFGCVIO-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-pyridin-2-ylquinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2N=CC=CC=2)=C(C=CC=C2)C2=N1 UEKJCEWDFGCVIO-UHFFFAOYSA-N 0.000 claims description 2
- RSNZNAOHQQKYBI-UHFFFAOYSA-N 2-[3,5-di(propan-2-yl)pyrazol-1-yl]-n-(4-methylcyclohexyl)quinazolin-4-amine Chemical compound N1=C(C(C)C)C=C(C(C)C)N1C1=NC(NC2CCC(C)CC2)=C(C=CC=C2)C2=N1 RSNZNAOHQQKYBI-UHFFFAOYSA-N 0.000 claims description 2
- GVWVXUCTNPBDOS-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2CC3=CC=CC=C3C2)=C(C=CC=C2)C2=N1 GVWVXUCTNPBDOS-UHFFFAOYSA-N 0.000 claims description 2
- PXBQVKMTASSKGZ-UHFFFAOYSA-N n-(4-tert-butylcyclohexyl)-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2CCC(CC2)C(C)(C)C)=C(C=CC=C2)C2=N1 PXBQVKMTASSKGZ-UHFFFAOYSA-N 0.000 claims description 2
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- QHKVGLNFNULLIU-UHFFFAOYSA-N n-butyl-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N=1C2=CC=CC=C2C(NCCCC)=NC=1N1N=C(C)C=C1C QHKVGLNFNULLIU-UHFFFAOYSA-N 0.000 claims description 2
- OJUFPACNUKNWJK-UHFFFAOYSA-N n-cycloheptyl-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2CCCCCC2)=C(C=CC=C2)C2=N1 OJUFPACNUKNWJK-UHFFFAOYSA-N 0.000 claims description 2
- WUFKOMSQZCSKNK-UHFFFAOYSA-N n-cyclohexyl-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2CCCCC2)=C(C=CC=C2)C2=N1 WUFKOMSQZCSKNK-UHFFFAOYSA-N 0.000 claims description 2
- XWPPYAGCVFNLFU-UHFFFAOYSA-N n-cyclohexyl-2-(3-methylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=CN1C1=NC(NC2CCCCC2)=C(C=CC=C2)C2=N1 XWPPYAGCVFNLFU-UHFFFAOYSA-N 0.000 claims description 2
- NCNJDONJFVRFNJ-UHFFFAOYSA-N n-cyclooctyl-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2CCCCCCC2)=C(C=CC=C2)C2=N1 NCNJDONJFVRFNJ-UHFFFAOYSA-N 0.000 claims description 2
- DKJFZUFVQZQPRB-UHFFFAOYSA-N n-cyclopentyl-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2CCCC2)=C(C=CC=C2)C2=N1 DKJFZUFVQZQPRB-UHFFFAOYSA-N 0.000 claims description 2
- ZBJUURWCGAROLY-UHFFFAOYSA-N n-cyclopropyl-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC2CC2)=C(C=CC=C2)C2=N1 ZBJUURWCGAROLY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 230000002265 prevention Effects 0.000 claims 2
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66114905P | 2005-03-14 | 2005-03-14 | |
| DKPA200500366 | 2005-03-14 | ||
| PCT/EP2006/060643 WO2006097441A1 (en) | 2005-03-14 | 2006-03-13 | Potassium channel modulating agents and their medical use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007010991A true MX2007010991A (es) | 2007-11-07 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2007010991A MX2007010991A (es) | 2005-03-14 | 2006-03-13 | Agentes que modulan el canal de potasio y su uso medico. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8252806B2 (enExample) |
| EP (1) | EP1861388B1 (enExample) |
| JP (1) | JP4966958B2 (enExample) |
| AU (1) | AU2006224605B2 (enExample) |
| CA (1) | CA2601527A1 (enExample) |
| MX (1) | MX2007010991A (enExample) |
| NZ (1) | NZ556248A (enExample) |
| WO (1) | WO2006097441A1 (enExample) |
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|---|---|---|---|---|
| EP1511744A4 (en) | 2002-05-13 | 2009-10-21 | Icagen Inc | Bis-benzimidazoles and related compounds as potassium channel modulators |
| WO2007098386A1 (en) * | 2006-02-17 | 2007-08-30 | Janssen Pharmaceutica N.V. | Pyrazolylquinazolinones as potassium channel openers |
| US20110144140A1 (en) * | 2006-09-07 | 2011-06-16 | Eriksen Birgitte L | Pyridinyl-pyrimidine derivatives useful as potassium channel modulating agents |
| JP2010505794A (ja) | 2006-10-03 | 2010-02-25 | ノイロサーチ アクティーゼルスカブ | カリウムチャネル調節剤として有用なインダゾリル誘導体 |
| EP2114916A2 (en) * | 2007-02-02 | 2009-11-11 | NeuroSearch A/S | Pyridinyl-pyrazole derivatives and their use as potassium channel modulators |
| EP2142546B1 (en) | 2007-03-28 | 2017-06-07 | Saniona A/S | Purinyl derivatives and their use as potassium channel modulators |
| EP2203436A1 (en) | 2007-09-17 | 2010-07-07 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
| EP2331527A1 (en) * | 2008-09-02 | 2011-06-15 | NeuroSearch A/S | Pyrazolyl-pyrimidine derivatives and their use as potassium channel modulators |
| WO2010034706A1 (en) * | 2008-09-26 | 2010-04-01 | Neurosearch A/S | Substituted purinyl-pyrazol derivatives and their use as potassium channel modulators |
| US8268838B2 (en) | 2008-09-26 | 2012-09-18 | Neurosearch A/S | Substituted purinyl-pyrazole derivatives and their use as potassium channel modulators |
| KR101123292B1 (ko) * | 2008-09-26 | 2012-03-19 | 주식회사 엘지생명과학 | 몬테루카스트 나트륨염의 제조방법 |
| EP2473487B1 (en) | 2009-09-03 | 2016-10-26 | Bristol-Myers Squibb Company | Quinazolines as potassium ion channel inhibitors |
| EP2885290B1 (en) | 2012-06-26 | 2017-10-18 | Saniona A/S | A phenyl triazole derivative and its use for modulating the gabaa receptor complex |
| JP2016516691A (ja) * | 2013-03-11 | 2016-06-09 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | カリウムイオンチャネル阻害剤としてのイソキノリン |
| US9242966B2 (en) | 2013-03-11 | 2016-01-26 | Bristol-Myers Squibb Company | Phthalazines as potassium ion channel inhibitors |
| CA2969856A1 (en) | 2014-12-05 | 2016-06-09 | Subramaniam Ananthan | Novel quinazolines as biogenic amine transport modulators |
| EP3226867A4 (en) * | 2014-12-05 | 2018-05-09 | Subramaniam Ananthan | Heterocyclic compounds as biogenic amine transport modulators |
| US20190112317A1 (en) * | 2015-10-05 | 2019-04-18 | The Trustees Of Columbia University In The City Of New York | Activators of autophagic flux and phospholipase d and clearance of protein aggregates including tau and treatment of proteinopathies |
| WO2017210545A1 (en) | 2016-06-02 | 2017-12-07 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| EP3571193B1 (en) | 2017-01-23 | 2021-12-01 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| EP3621434B1 (en) | 2017-05-10 | 2026-07-15 | University of Rochester | Glial progenitor cells for use in treating schizophrenia |
| FR3066761B1 (fr) * | 2017-05-23 | 2020-10-30 | Centre Nat Rech Scient | Nouveaux composes inhibiteurs des canaux ioniques |
| MX2021004647A (es) | 2018-10-22 | 2021-08-16 | Novartis Ag | Formas cristalinas de moduladores de los canales de potasio. |
| WO2024191106A1 (ko) * | 2023-03-13 | 2024-09-19 | 주식회사 미토이뮨테라퓨틱스 | 뇌전증 예방 또는 치료용 약학적 조성물 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3340260A (en) * | 1962-12-03 | 1967-09-05 | Ciba Geigy Corp | 4-amino-pyrimidines |
| IL88507A (en) | 1987-12-03 | 1993-02-21 | Smithkline Beckman Intercredit | 2,4-diaminoquinazolines, process for their preparation and pharmaceutical compositions comprising them |
| PT100905A (pt) | 1991-09-30 | 1994-02-28 | Eisai Co Ltd | Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem |
| JP2657760B2 (ja) * | 1992-07-15 | 1997-09-24 | 小野薬品工業株式会社 | ４−アミノキナゾリン誘導体およびそれを含有する医薬品 |
| US5539895A (en) * | 1994-05-12 | 1996-07-23 | International Business Machines Corporation | Hierarchical computer cache system |
| US6184226B1 (en) * | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
| HN2002000067A (es) * | 2001-03-23 | 2003-10-24 | Bayer Healthcare Llc | Inhibidores de la rho - quinasa. |
| WO2004065392A1 (en) * | 2003-01-24 | 2004-08-05 | Smithkline Beecham Corporation | Condensed pyridines and pyrimidines and their use as alk-5 receptor ligands |
| CL2004000409A1 (es) * | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| JP2007532669A (ja) * | 2004-04-13 | 2007-11-15 | イカジェン インコーポレイテッド | カリウムイオンチャネル調節剤としての多環式ピリミジン |
| EP1844023A1 (en) | 2004-12-31 | 2007-10-17 | Sk Chemicals Co., Ltd. | Quinazoline derivatives for the treatment and prevention of diabetes and obesity |
| US20090036475A1 (en) | 2005-03-22 | 2009-02-05 | Neurosearch A/S | Pyrazolyl-Pyrimidines as Potassium Channel Modulating Agents and Their Medical Use |
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- 2006-03-13 JP JP2008501279A patent/JP4966958B2/ja not_active Expired - Fee Related
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- 2006-03-13 WO PCT/EP2006/060643 patent/WO2006097441A1/en not_active Ceased
- 2006-03-13 CA CA002601527A patent/CA2601527A1/en not_active Abandoned
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| CA2601527A1 (en) | 2006-09-21 |
| JP4966958B2 (ja) | 2012-07-04 |
| US20080275045A1 (en) | 2008-11-06 |
| AU2006224605B2 (en) | 2012-03-01 |
| EP1861388A1 (en) | 2007-12-05 |
| EP1861388B1 (en) | 2017-07-05 |
| NZ556248A (en) | 2010-06-25 |
| WO2006097441A1 (en) | 2006-09-21 |
| JP2008533087A (ja) | 2008-08-21 |
| US8252806B2 (en) | 2012-08-28 |
| AU2006224605A1 (en) | 2006-09-21 |
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