JP2013519728A - カリウムチャンネルモジュレーターとしてのヘテロ環 - Google Patents

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Publication number

JP2013519728A

JP2013519728A JP2012553927A JP2012553927A JP2013519728A JP 2013519728 A JP2013519728 A JP 2013519728A JP 2012553927 A JP2012553927 A JP 2012553927A JP 2012553927 A JP2012553927 A JP 2012553927A JP 2013519728 A JP2013519728 A JP 2013519728A

Authority

JP

Japan

Prior art keywords

alkyl

fluoro

pyridin

pyridyl

trifluoromethyl

Prior art date

2010-02-16

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 108020001213 potassium channel Proteins 0.000 title claims abstract description 55
• 102000004257 Potassium Channel Human genes 0.000 title claims abstract description 54
• 125000000623 heterocyclic group Chemical group 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 399
• 238000000034 method Methods 0.000 claims abstract description 89
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 56
• 208000035475 disorder Diseases 0.000 claims abstract description 37
• 238000011282 treatment Methods 0.000 claims abstract description 35
• 206010010904 Convulsion Diseases 0.000 claims abstract description 22
• 206010015037 epilepsy Diseases 0.000 claims abstract description 19
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 18
• 102000003734 Voltage-Gated Potassium Channels Human genes 0.000 claims abstract description 18
• 108090000013 Voltage-Gated Potassium Channels Proteins 0.000 claims abstract description 18
• 230000036506 anxiety Effects 0.000 claims abstract description 16
• 208000019695 Migraine disease Diseases 0.000 claims abstract description 13
• 206010027599 migraine Diseases 0.000 claims abstract description 13
• 210000003169 central nervous system Anatomy 0.000 claims abstract description 12
• 230000010370 hearing loss Effects 0.000 claims abstract description 12
• 231100000888 hearing loss Toxicity 0.000 claims abstract description 12
• 208000016354 hearing loss disease Diseases 0.000 claims abstract description 12
• 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 11
• 208000020925 Bipolar disease Diseases 0.000 claims abstract description 10
• 206010011878 Deafness Diseases 0.000 claims abstract description 10
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 10
• 210000001428 peripheral nervous system Anatomy 0.000 claims abstract description 10
• 201000007737 Retinal degeneration Diseases 0.000 claims abstract description 9
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 9
• 208000020016 psychiatric disease Diseases 0.000 claims abstract description 9
• 230000004258 retinal degeneration Effects 0.000 claims abstract description 9
• 206010044652 trigeminal neuralgia Diseases 0.000 claims abstract description 9
• 208000019022 Mood disease Diseases 0.000 claims abstract description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
• 208000000044 Amnesia Diseases 0.000 claims abstract description 7
• 206010003591 Ataxia Diseases 0.000 claims abstract description 7
• 201000004569 Blindness Diseases 0.000 claims abstract description 7
• 208000003174 Brain Neoplasms Diseases 0.000 claims abstract description 7
• 208000026139 Memory disease Diseases 0.000 claims abstract description 7
• 208000026072 Motor neurone disease Diseases 0.000 claims abstract description 7
• 208000008238 Muscle Spasticity Diseases 0.000 claims abstract description 7
• 230000032683 aging Effects 0.000 claims abstract description 7
• 230000006984 memory degeneration Effects 0.000 claims abstract description 7
• 208000023060 memory loss Diseases 0.000 claims abstract description 7
• 208000005264 motor neuron disease Diseases 0.000 claims abstract description 7
• 208000018198 spasticity Diseases 0.000 claims abstract description 7
• -1 1-methylcyclopentyl Chemical group 0.000 claims description 617
• 125000000217 alkyl group Chemical group 0.000 claims description 333
• 125000001424 substituent group Chemical group 0.000 claims description 111
• 125000003118 aryl group Chemical group 0.000 claims description 110
• 208000002193 Pain Diseases 0.000 claims description 90
• 229910052736 halogen Inorganic materials 0.000 claims description 84
• 125000003545 alkoxy group Chemical group 0.000 claims description 83
• 150000002367 halogens Chemical class 0.000 claims description 82
• 230000036407 pain Effects 0.000 claims description 72
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
• 229910052799 carbon Inorganic materials 0.000 claims description 65
• 125000001072 heteroaryl group Chemical group 0.000 claims description 59
• 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 58
• 150000003839 salts Chemical class 0.000 claims description 58
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 58
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 210000004027 cell Anatomy 0.000 claims description 41
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 41
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 36
• 239000012453 solvate Substances 0.000 claims description 35
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 34
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 34
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 31
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 30
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 29
• 230000000694 effects Effects 0.000 claims description 28
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 24
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 24
• 125000005842 heteroatom Chemical group 0.000 claims description 23
• 150000002500 ions Chemical class 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 19
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 19
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 17
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 14
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
• 125000002619 bicyclic group Chemical group 0.000 claims description 14
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
• 125000002950 monocyclic group Chemical group 0.000 claims description 14
• 230000001965 increasing effect Effects 0.000 claims description 13
• 208000004296 neuralgia Diseases 0.000 claims description 13
• 208000021722 neuropathic pain Diseases 0.000 claims description 13
• 125000003367 polycyclic group Chemical group 0.000 claims description 13
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 11
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 11
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 208000009935 visceral pain Diseases 0.000 claims description 11
• 206010058019 Cancer Pain Diseases 0.000 claims description 10
• 239000004215 Carbon black (E152) Substances 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 229930195733 hydrocarbon Natural products 0.000 claims description 10
• 206010065390 Inflammatory pain Diseases 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 7
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 7
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 7
• 208000001294 Nociceptive Pain Diseases 0.000 claims description 7
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 208000006011 Stroke Diseases 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 claims description 5
• 230000006735 deficit Effects 0.000 claims description 5
• 125000001188 haloalkyl group Chemical group 0.000 claims description 5
• 230000013016 learning Effects 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 229920002554 vinyl polymer Polymers 0.000 claims description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims 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 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• ILWFNKLXPUKLEP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)-2-fluorobenzene Chemical group FC1=CC(CCl)=CC=C1Cl ILWFNKLXPUKLEP-UHFFFAOYSA-N 0.000 claims description 3
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 3
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 3
• 125000006499 2-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 3
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 3
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 3
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• 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000006500 3-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC(F)(F)F)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 3
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
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• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 claims description 3
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 3
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• 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 claims description 3
• 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims description 3
• 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 3
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 3
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 3
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• 125000004076 pyridyl group Chemical group 0.000 claims description 2
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