JP2008533087A5 - - Google Patents
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- JP2008533087A5 JP2008533087A5 JP2008501279A JP2008501279A JP2008533087A5 JP 2008533087 A5 JP2008533087 A5 JP 2008533087A5 JP 2008501279 A JP2008501279 A JP 2008501279A JP 2008501279 A JP2008501279 A JP 2008501279A JP 2008533087 A5 JP2008533087 A5 JP 2008533087A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyrazol
- quinazolin
- amine
- dimethyl
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 15
- 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 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- -1 cyano, nitro, amino, methylenedioxy, phenyl Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 9
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000002837 carbocyclic group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 102000004257 Potassium Channel Human genes 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 108020001213 potassium channel Proteins 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000003367 polycyclic group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 208000023504 respiratory system disease Diseases 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 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 1
- IATRPJHLBLVBDI-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n,n-diethylquinazolin-4-amine Chemical compound N=1C2=CC=CC=C2C(N(CC)CC)=NC=1N1N=C(C)C=C1C IATRPJHLBLVBDI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YGXYZTCBQCGBNE-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(1h-indol-7-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=3NC=CC=3C=CC=2)=C(C=CC=C2)C2=N1 YGXYZTCBQCGBNE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- PTBCYBGNJFQOBW-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(4-methylcyclohexyl)quinazolin-4-amine Chemical compound C1CC(C)CCC1NC1=NC(N2C(=CC(C)=N2)C)=NC2=CC=CC=C12 PTBCYBGNJFQOBW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- POUCPZAQSUGANK-UHFFFAOYSA-N 2-(3,5-dimethylpyrazol-1-yl)-n-(4-morpholin-4-ylphenyl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=CC(=CC=2)N2CCOCC2)=C(C=CC=C2)C2=N1 POUCPZAQSUGANK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010003225 Arteriospasm coronary Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010048994 Bladder spasm Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000005171 Dysmenorrhea Diseases 0.000 claims 1
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010062016 Immunosuppression Diseases 0.000 claims 1
- 206010022562 Intermittent claudication Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000008238 Muscle Spasticity Diseases 0.000 claims 1
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000005107 Premature Birth Diseases 0.000 claims 1
- 206010036590 Premature baby Diseases 0.000 claims 1
- 208000003782 Raynaud disease Diseases 0.000 claims 1
- 208000012322 Raynaud phenomenon Diseases 0.000 claims 1
- 208000036071 Rhinorrhea Diseases 0.000 claims 1
- 206010039101 Rhinorrhoea Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 206010047163 Vasospasm Diseases 0.000 claims 1
- 230000006578 abscission Effects 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 231100000360 alopecia Toxicity 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 230000033228 biological regulation Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010013781 dry mouth Diseases 0.000 claims 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 208000021156 intermittent vascular claudication Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 230000000116 mitigating effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- SMYSNYASGKZITB-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=C3OCOC3=CC=2)=C(C=CC=C2)C2=N1 SMYSNYASGKZITB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- LVPJYSLBTVOBHB-UHFFFAOYSA-N n-[(3,4-difluorophenyl)methyl]-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NCC=2C=C(F)C(F)=CC=2)=C(C=CC=C2)C2=N1 LVPJYSLBTVOBHB-UHFFFAOYSA-N 0.000 claims 1
- GHSYVHJFWCWZMZ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NCC=2C=CC(Cl)=CC=2)=C(C=CC=C2)C2=N1 GHSYVHJFWCWZMZ-UHFFFAOYSA-N 0.000 claims 1
- LADYYLFFMKHLJJ-UHFFFAOYSA-N n-[3,5-bis(trifluoromethyl)phenyl]-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C(C=CC=C2)C2=N1 LADYYLFFMKHLJJ-UHFFFAOYSA-N 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- PULDFTZDWXGLNN-UHFFFAOYSA-N n-benzyl-2-(3,5-dimethylpyrazol-1-yl)quinazolin-4-amine Chemical compound N1=C(C)C=C(C)N1C1=NC(NCC=2C=CC=CC=2)=C(C=CC=C2)C2=N1 PULDFTZDWXGLNN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- TWLTUFCLTQFHHS-UHFFFAOYSA-N n-cyclohexyl-2-[3,5-di(propan-2-yl)pyrazol-1-yl]quinazolin-4-amine Chemical compound N1=C(C(C)C)C=C(C(C)C)N1C1=NC(NC2CCCCC2)=C(C=CC=C2)C2=N1 TWLTUFCLTQFHHS-UHFFFAOYSA-N 0.000 claims 1
- CVPOZEGTLACCOF-UHFFFAOYSA-N n-cyclohexyl-2-pyrazol-1-ylquinazolin-4-amine Chemical compound C1CCCCC1NC1=NC(N2N=CC=C2)=NC2=CC=CC=C12 CVPOZEGTLACCOF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
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- 208000030761 polycystic kidney disease Diseases 0.000 claims 1
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- 239000000651 prodrug Substances 0.000 claims 1
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- 230000000069 prophylactic effect Effects 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 201000009881 secretory diarrhea Diseases 0.000 claims 1
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| PCT/EP2006/060643 WO2006097441A1 (en) | 2005-03-14 | 2006-03-13 | Potassium channel modulating agents and their medical use |
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| JP2005530763A (ja) | 2002-05-13 | 2005-10-13 | アイシーエージェン，インコーポレイティド | カリウム・チャネル調節物質としてのビス−ベンズイミダゾール及び関連化合物 |
| AU2007217099A1 (en) | 2006-02-17 | 2007-08-30 | Janssen Pharmaceutica N.V. | Pyrazolylquinazolinones as potassium channel openers |
| WO2008028935A2 (en) * | 2006-09-07 | 2008-03-13 | Neurosearch A/S | Pyridinyl-pyrimidine derivatives useful as potassium channel modulating agents |
| WO2008040753A1 (en) | 2006-10-03 | 2008-04-10 | Neurosearch A/S | Indazolyl derivatives useful as potassium channel modulating agents |
| JP2010517970A (ja) * | 2007-02-02 | 2010-05-27 | ノイロサーチ アクティーゼルスカブ | ピリジニル−ピラゾール誘導体及びカリウムチャネル調節剤としてのそれらの使用 |
| WO2008116911A1 (en) * | 2007-03-28 | 2008-10-02 | Neurosearch A/S | Purinyl derivatives and their use as potassium channel modulators |
| US8415358B2 (en) | 2007-09-17 | 2013-04-09 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
| WO2010026087A1 (en) * | 2008-09-02 | 2010-03-11 | Neurosearch A/S | Pyrazolyl-pyrimidine derivatives and their use as potassium channel modulators |
| EP2344501A1 (en) * | 2008-09-26 | 2011-07-20 | NeuroSearch A/S | Substituted purinyl-pyrazol derivatives and their use as potassium channel modulators |
| WO2010034707A1 (en) * | 2008-09-26 | 2010-04-01 | Neurosearch A/S | Substituted purinyl-pyrazol derivatives and their use as potassium channel modulators |
| KR101123292B1 (ko) * | 2008-09-26 | 2012-03-19 | 주식회사 엘지생명과학 | 몬테루카스트 나트륨염의 제조방법 |
| EP3124475B1 (en) | 2009-09-03 | 2019-08-07 | Bristol-Myers Squibb Company | Quinazolines as potassium ion channel inhibitors |
| WO2014001282A1 (en) | 2012-06-26 | 2014-01-03 | Aniona Aps | A phenyl triazole derivative and its use for modulating the gabaa receptor complex |
| WO2014143609A1 (en) * | 2013-03-11 | 2014-09-18 | Bristol-Myers Squibb Company | Isoquinolines as potassium ion channel inhibitors |
| US9242966B2 (en) * | 2013-03-11 | 2016-01-26 | Bristol-Myers Squibb Company | Phthalazines as potassium ion channel inhibitors |
| WO2016090296A1 (en) * | 2014-12-05 | 2016-06-09 | Subramaniam Ananthan | Heterocyclic compounds as biogenic amine transport modulators |
| KR20170117024A (ko) | 2014-12-05 | 2017-10-20 | 서브라마니암 아난탄 | 생체 아민 수송 조절인자로서 신규한 퀴나졸린 |
| JP6740354B2 (ja) * | 2015-10-05 | 2020-08-12 | ザ トラスティーズ オブ コロンビア ユニバーシティー イン ザ シティー オブ ニューヨーク | オートファジーの流れ及びホスホリパーゼｄ及びタウを含むタンパク質凝集体のクリアランスの活性化剤ならびにタンパク質症の治療方法 |
| AU2017275657B2 (en) | 2016-06-02 | 2021-08-19 | Novartis Ag | Potassium channel modulators |
| EP3571193B1 (en) | 2017-01-23 | 2021-12-01 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| JP7457505B2 (ja) | 2017-05-10 | 2024-03-28 | ユニバーシティー オブ ロチェスター | 神経精神障害を処置する方法 |
| FR3066761B1 (fr) * | 2017-05-23 | 2020-10-30 | Centre Nat Rech Scient | Nouveaux composes inhibiteurs des canaux ioniques |
| EP3870291A1 (en) | 2018-10-22 | 2021-09-01 | Cadent Therapeutics, Inc. | Crystalline forms of potassium channel modulators |
| KR20240138992A (ko) * | 2023-03-13 | 2024-09-20 | 주식회사 미토이뮨테라퓨틱스 | 뇌전증 예방 또는 치료용 약학적 조성물 |
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| 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 |
| EP1370553B1 (en) | 2001-03-23 | 2006-05-10 | Bayer Corporation | Rho-kinase inhibitors |
| 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 |
| US7560464B2 (en) * | 2004-04-13 | 2009-07-14 | Icagen, Inc. | Polycyclic pyrimidines as potassium ion channel modulators |
| WO2006071095A1 (en) | 2004-12-31 | 2006-07-06 | 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 EP EP06725016.7A patent/EP1861388B1/en active Active
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- 2006-03-13 US US11/886,341 patent/US8252806B2/en active Active
- 2006-03-13 NZ NZ556248A patent/NZ556248A/en not_active IP Right Cessation
- 2006-03-13 CA CA002601527A patent/CA2601527A1/en not_active Abandoned
- 2006-03-13 WO PCT/EP2006/060643 patent/WO2006097441A1/en not_active Ceased
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