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
- 208000035475 disorder Diseases 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 230000000694 effects Effects 0.000 claims abstract description 16
- 206010010904 Convulsion Diseases 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 10
- 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 9
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 8
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 8
- 230000036506 anxiety Effects 0.000 claims abstract description 8
- 206010015037 epilepsy Diseases 0.000 claims abstract description 8
- 208000002193 Pain Diseases 0.000 claims abstract description 7
- 230000003274 myotonic effect Effects 0.000 claims abstract description 7
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 7
- 201000004384 Alopecia Diseases 0.000 claims abstract description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 6
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 6
- 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 6
- 206010012289 Dementia Diseases 0.000 claims abstract description 6
- 206010012735 Diarrhoea Diseases 0.000 claims abstract description 6
- 208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 6
- 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 6
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims abstract description 6
- 206010020772 Hypertension Diseases 0.000 claims abstract description 6
- 206010022562 Intermittent claudication Diseases 0.000 claims abstract description 6
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 6
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
- 208000030886 Traumatic Brain injury Diseases 0.000 claims abstract description 6
- 201000011510 cancer Diseases 0.000 claims abstract description 6
- 208000029078 coronary artery disease Diseases 0.000 claims abstract description 6
- 230000006735 deficit Effects 0.000 claims abstract description 6
- 230000007160 gastrointestinal dysfunction Effects 0.000 claims abstract description 6
- 230000003676 hair loss Effects 0.000 claims abstract description 6
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims abstract description 6
- 201000008980 hyperinsulinism Diseases 0.000 claims abstract description 6
- 208000021156 intermittent vascular claudication Diseases 0.000 claims abstract description 6
- 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 6
- 208000028867 ischemia Diseases 0.000 claims abstract description 6
- 208000017169 kidney disease Diseases 0.000 claims abstract description 6
- 206010027599 migraine Diseases 0.000 claims abstract description 6
- 208000031225 myocardial ischemia Diseases 0.000 claims abstract description 6
- 201000003631 narcolepsy Diseases 0.000 claims abstract description 6
- 208000030761 polycystic kidney disease Diseases 0.000 claims abstract description 6
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 6
- 230000009529 traumatic brain injury Effects 0.000 claims abstract description 6
- 206010003225 Arteriospasm coronary Diseases 0.000 claims abstract description 5
- 208000003890 Coronary Vasospasm Diseases 0.000 claims abstract description 5
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 5
- 230000006793 arrhythmia Effects 0.000 claims abstract description 5
- 201000011634 coronary artery vasospasm Diseases 0.000 claims abstract description 5
- 230000008629 immune suppression Effects 0.000 claims abstract description 5
- 206010048994 Bladder spasm Diseases 0.000 claims abstract description 4
- -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
- 201000006938 muscular dystrophy Diseases 0.000 claims description 6
- 201000006474 Brain Ischemia Diseases 0.000 claims description 5
- 206010034759 Petit mal epilepsy Diseases 0.000 claims description 5
- 208000005946 Xerostomia Diseases 0.000 claims description 5
- 206010008118 cerebral infarction Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 206010013781 dry mouth Diseases 0.000 claims description 5
- 201000009881 secretory diarrhea Diseases 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- 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
- 206010003591 Ataxia Diseases 0.000 claims description 4
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- 208000007101 Muscle Cramp Diseases 0.000 claims description 4
- 208000008238 Muscle Spasticity Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 4
- 208000036071 Rhinorrhea Diseases 0.000 claims description 4
- 206010039101 Rhinorrhoea Diseases 0.000 claims description 4
- 208000005392 Spasm Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 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
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 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
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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
- ARMQQOXIHQRINP-UHFFFAOYSA-N 1H-pyrazole quinazoline Chemical class C=1C=NNC=1.N1=CN=CC2=CC=CC=C21 ARMQQOXIHQRINP-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
- 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
- 241000124008 Mammalia Species 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 16
- 206010047163 Vasospasm Diseases 0.000 abstract description 5
- 206010036600 Premature labour Diseases 0.000 abstract description 3
- 210000003205 muscle Anatomy 0.000 abstract description 3
- 208000028311 absence seizure Diseases 0.000 abstract 1
- 230000036461 convulsion Effects 0.000 abstract 1
- 206010012601 diabetes mellitus Diseases 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 109
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 46
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 44
- 108091006146 Channels Proteins 0.000 description 25
- 125000005843 halogen group Chemical group 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002775 capsule Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 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 8
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000002552 dosage form Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- 101710201179 Small conductance calcium-activated potassium channel protein 3 Proteins 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 210000003932 urinary bladder Anatomy 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 210000000170 cell membrane Anatomy 0.000 description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- CNYBDYZKULUYHQ-UHFFFAOYSA-N 2-chloro-n-propylquinazolin-4-amine Chemical compound C1=CC=C2C(NCCC)=NC(Cl)=NC2=C1 CNYBDYZKULUYHQ-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 101001026232 Homo sapiens Small conductance calcium-activated potassium channel protein 3 Proteins 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 102000004310 Ion Channels Human genes 0.000 description 3
- 108090000862 Ion Channels Proteins 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 230000036982 action potential Effects 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 201000006370 kidney failure Diseases 0.000 description 3
- 239000007937 lozenge Substances 0.000 description 3
- 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 description 3
- 210000002569 neuron Anatomy 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 210000002027 skeletal muscle Anatomy 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 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 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- PJSJVTZSFIRYIZ-UHFFFAOYSA-N 3,5-di(propan-2-yl)-1h-pyrazole Chemical compound CC(C)C=1C=C(C(C)C)NN=1 PJSJVTZSFIRYIZ-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000006041 3-hexenyl group Chemical group 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 2
- 125000006043 5-hexenyl group Chemical group 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 241000220479 Acacia Species 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 108010092555 Large-Conductance Calcium-Activated Potassium Channels Proteins 0.000 description 2
- 102000016469 Large-Conductance Calcium-Activated Potassium Channels Human genes 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 2
- 210000003928 nasal cavity Anatomy 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 208000026440 premature labor Diseases 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Chemical group 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- 125000004953 trihalomethyl group Chemical group 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- PHLZUDXEBCQHKM-UHFFFAOYSA-N (3,4-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C(F)=C1 PHLZUDXEBCQHKM-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- MIMYTSWNVBMNRH-UHFFFAOYSA-N 1h-indol-6-amine Chemical compound NC1=CC=C2C=CNC2=C1 MIMYTSWNVBMNRH-UHFFFAOYSA-N 0.000 description 1
- UOXJNGFFPMOZDM-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]ethylsulfanyl-methylphosphinic acid Chemical compound CC(C)N(C(C)C)CCSP(C)(O)=O UOXJNGFFPMOZDM-UHFFFAOYSA-N 0.000 description 1
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical compound C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- AKKYWYCANLVLAS-UHFFFAOYSA-N 2-chloro-n-phenylquinazolin-4-amine Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1NC1=CC=CC=C1 AKKYWYCANLVLAS-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- MUKFIGWFEAKKHX-UHFFFAOYSA-N 3,5-bis(2,2,2-trifluoroethyl)aniline Chemical compound NC1=CC(CC(F)(F)F)=CC(CC(F)(F)F)=C1 MUKFIGWFEAKKHX-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 1
- PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 description 1
- BGNLXETYTAAURD-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-amine Chemical compound CC(C)(C)C1CCC(N)CC1 BGNLXETYTAAURD-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical class CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
- 108010045489 Calcium-Activated Potassium Channels Proteins 0.000 description 1
- 102000005702 Calcium-Activated Potassium Channels Human genes 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010061876 Obstruction Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 208000005107 Premature Birth Diseases 0.000 description 1
- 206010036590 Premature baby Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 108010084455 Zeocin Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000007883 bronchodilation Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000006165 cyclic alkyl 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
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229950005627 embonate Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 230000002397 epileptogenic effect Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 239000013604 expression vector Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 210000000609 ganglia Anatomy 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000008263 liquid aerosol Substances 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- CWCMIVBLVUHDHK-ZSNHEYEWSA-N phleomycin D1 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC[C@@H](N=1)C=1SC=C(N=1)C(=O)NCCCCNC(N)=N)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C CWCMIVBLVUHDHK-ZSNHEYEWSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- QVLTXCYWHPZMCA-UHFFFAOYSA-N po4-po4 Chemical class OP(O)(O)=O.OP(O)(O)=O QVLTXCYWHPZMCA-UHFFFAOYSA-N 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000010473 stable expression Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003443 succinic acid derivatives Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 102000035160 transmembrane proteins Human genes 0.000 description 1
- 108091005703 transmembrane proteins Proteins 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000004951 trihalomethoxy group Chemical group 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Transplantation (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Emergency Medicine (AREA)
- Pregnancy & Childbirth (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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
ID=36600224
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) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1511744A4 (en) | 2002-05-13 | 2009-10-21 | Icagen Inc | Bis-benzimidazoles and related compounds as potassium channel modulators |
| CA2642832A1 (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 |
| MX2009003142A (es) | 2006-10-03 | 2009-04-06 | Neurosearch As | Derivados de indazolilo utiles como agentes moduladores del canal de potasio. |
| EP2114916A2 (en) * | 2007-02-02 | 2009-11-11 | NeuroSearch A/S | Pyridinyl-pyrazole derivatives and their use as potassium channel modulators |
| WO2008116910A1 (en) | 2007-03-28 | 2008-10-02 | Neurosearch A/S | Purinyl derivatives and their use as potassium channel modulators |
| WO2009037247A1 (en) | 2007-09-17 | 2009-03-26 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
| JP2012501308A (ja) * | 2008-09-02 | 2012-01-19 | ノイロサーチ アクティーゼルスカブ | ピラゾリルピリミジン誘導体及びカリウムチャネルモジュレーターとしてのそれらの使用 |
| WO2010034706A1 (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 |
| WO2010034707A1 (en) * | 2008-09-26 | 2010-04-01 | Neurosearch A/S | Substituted purinyl-pyrazol derivatives and their use as potassium channel modulators |
| PE20121153A1 (es) | 2009-09-03 | 2012-08-27 | Bristol Myers Squibb Co | Quinazolinas como inhibidores de los canales ionicos de potasio |
| EP2885290B1 (en) | 2012-06-26 | 2017-10-18 | Saniona A/S | A phenyl triazole derivative and its use for modulating the gabaa receptor complex |
| US9242966B2 (en) * | 2013-03-11 | 2016-01-26 | Bristol-Myers Squibb Company | Phthalazines as potassium ion channel inhibitors |
| EP2970199A1 (en) | 2013-03-11 | 2016-01-20 | Bristol-Myers Squibb Company | Isoquinolines as potassium ion channel inhibitors |
| CA2969856A1 (en) | 2014-12-05 | 2016-06-09 | Subramaniam Ananthan | Novel quinazolines as biogenic amine transport modulators |
| AU2015357596A1 (en) * | 2014-12-05 | 2017-06-29 | Southern Research Institute | Heterocyclic compounds as biogenic amine transport modulators |
| BR112018006873A2 (pt) * | 2015-10-05 | 2018-11-06 | The Trustees Of Columbia University In The City Of New York | ativadores do fluxo autofágico e fosfolipase d e depuração de agregados de proteína incluindo tau e tratamento de proteinopatias |
| CA3026149A1 (en) | 2016-06-02 | 2017-12-07 | Cadent Therapeutics, Inc. | Potassium channel modulators |
| HUE057710T2 (hu) | 2017-01-23 | 2022-05-28 | Cadent Therapeutics Inc | Káliumcsatorna modulátorok |
| US11690876B2 (en) | 2017-05-10 | 2023-07-04 | University Of Rochester | Methods of treating neuropsychiatric disorders |
| FR3066761B1 (fr) | 2017-05-23 | 2020-10-30 | Centre Nat Rech Scient | Nouveaux composes inhibiteurs des canaux ioniques |
| MA53978A (fr) | 2018-10-22 | 2021-09-01 | Cadent Therapeutics Inc | Formes cristallines de modulateurs des canaux potassiques |
| KR20240138992A (ko) * | 2023-03-13 | 2024-09-20 | 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 |
| MY134783A (en) | 2001-03-23 | 2007-12-31 | Bayer Healthcare Llc | 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 |
| WO2005099711A1 (en) * | 2004-04-13 | 2005-10-27 | Icagen, Inc. | Polycyclic pyrimidines as potassium ion channel modulators |
| 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 |
-
2006
- 2006-03-13 JP JP2008501279A patent/JP4966958B2/ja not_active Expired - Fee Related
- 2006-03-13 CA CA002601527A patent/CA2601527A1/en not_active Abandoned
- 2006-03-13 EP EP06725016.7A patent/EP1861388B1/en active Active
- 2006-03-13 AU AU2006224605A patent/AU2006224605B2/en not_active Ceased
- 2006-03-13 NZ NZ556248A patent/NZ556248A/en not_active IP Right Cessation
- 2006-03-13 WO PCT/EP2006/060643 patent/WO2006097441A1/en not_active Ceased
- 2006-03-13 MX MX2007010991A patent/MX2007010991A/es active IP Right Grant
- 2006-03-13 US US11/886,341 patent/US8252806B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1861388A1 (en) | 2007-12-05 |
| JP2008533087A (ja) | 2008-08-21 |
| AU2006224605A1 (en) | 2006-09-21 |
| NZ556248A (en) | 2010-06-25 |
| US20080275045A1 (en) | 2008-11-06 |
| WO2006097441A1 (en) | 2006-09-21 |
| US8252806B2 (en) | 2012-08-28 |
| EP1861388B1 (en) | 2017-07-05 |
| JP4966958B2 (ja) | 2012-07-04 |
| AU2006224605B2 (en) | 2012-03-01 |
| CA2601527A1 (en) | 2006-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8252806B2 (en) | Potassium channel modulating agents and their medical use | |
| EP1966184B1 (en) | Pyridinyl-quinazoline derivatives and their medical use | |
| US8415358B2 (en) | Pyrazine derivatives and their use as potassium channel modulators | |
| JP2010522721A (ja) | プリニル誘導体及びカリウムチャネルモジュレーターとしてのそれらの使用 | |
| US7723347B2 (en) | Substituted phenylamino-pyrimidines | |
| JP2010505794A (ja) | 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 | |
| EP1091942B1 (en) | Potassium channel blocking agents | |
| EP1863796A1 (en) | Pyrazolyl-pyrimidines as potassium channel modulating agents and their medical use | |
| JP2003522163A (ja) | Ｅｒｋのインヒビターとして有用なピラゾール組成物 | |
| EP2144911A2 (en) | Purinyl derivatives and their use as potassium channel modulators | |
| US20090036475A1 (en) | Pyrazolyl-Pyrimidines as Potassium Channel Modulating Agents and Their Medical Use | |
| JP2009530237A (ja) | キナゾリノン及びカリウムチャネル活性化剤としてのその使用 | |
| AU2009334869A1 (en) | Substituted quinazoline compounds | |
| JP2010502674A (ja) | カリウムチャンネル調節剤として有用なピリジニル−ピリミジン誘導体 | |
| JP2010517970A (ja) | 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 | |
| CN101115736A (zh) | 钾通道调节剂和它们的医药用途 | |
| US20080176859A1 (en) | Heterocyclyamide-substituted imidazoles | |
| JP2012501308A (ja) | ピラゾリルピリミジン誘導体及びカリウムチャネルモジュレーターとしてのそれらの使用 | |
| JP2002544258A (ja) | イオンチャネル調節剤 | |
| US7767704B2 (en) | Antiviral 4-aminocarbonylamino-substituted imidazole compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |