JP2017511794A5 - - Google Patents

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Publication number

JP2017511794A5

JP2017511794A5 JP2016551246A JP2016551246A JP2017511794A5 JP 2017511794 A5 JP2017511794 A5 JP 2017511794A5 JP 2016551246 A JP2016551246 A JP 2016551246A JP 2016551246 A JP2016551246 A JP 2016551246A JP 2017511794 A5 JP2017511794 A5 JP 2017511794A5

Authority

JP

Japan

Prior art keywords

optionally substituted

alkyl

amino

compound

alkoxy

Prior art date

2015-02-12

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

Granted

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• 125000000217 alkyl group Chemical group 0.000 claims 66
• 150000001875 compounds Chemical class 0.000 claims 42
• 125000000623 heterocyclic group Chemical group 0.000 claims 33
• 125000003545 alkoxy group Chemical group 0.000 claims 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 23
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 22
• -1 —S (O) m —R f Chemical group 0.000 claims 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
• 125000000547 substituted alkyl group Chemical group 0.000 claims 14
• 229910052736 halogen Inorganic materials 0.000 claims 13
• 125000001072 heteroaryl group Chemical group 0.000 claims 13
• 150000002367 halogens Chemical class 0.000 claims 12
• 125000001424 substituent group Chemical group 0.000 claims 12
• 150000003857 carboxamides Chemical class 0.000 claims 11
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 11
• 150000001204 N-oxides Chemical class 0.000 claims 9
• 229910052757 nitrogen Inorganic materials 0.000 claims 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
• 150000003839 salts Chemical class 0.000 claims 9
• 239000012453 solvate Substances 0.000 claims 9
• 208000002193 Pain Diseases 0.000 claims 8
• 125000001188 haloalkyl group Chemical group 0.000 claims 7
• 229940124530 sulfonamide Drugs 0.000 claims 7
• 150000003456 sulfonamides Chemical class 0.000 claims 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims 6
• 230000036407 pain Effects 0.000 claims 6
• 125000003107 substituted aryl group Chemical group 0.000 claims 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
• 125000005843 halogen group Chemical group 0.000 claims 5
• 125000003118 aryl group Chemical group 0.000 claims 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
• 125000003396 thiol group Chemical group [H]S* 0.000 claims 3
• 125000005518 carboxamido group Chemical group 0.000 claims 2
• 239000003085 diluting agent Substances 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• 238000000034 method Methods 0.000 claims 2
• 239000000203 mixture Substances 0.000 claims 2
• 239000008194 pharmaceutical composition Substances 0.000 claims 2
• 229920006395 saturated elastomer Polymers 0.000 claims 2
• UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
• WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims 1
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
• RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 1
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims 1
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims 1
• QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
• BKZXMCAIWWDHSQ-JOCHJYFZSA-N 6-[(1S)-1,2-dihydroxyethyl]-4-[5-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]pyridine-2-carboxamide Chemical compound O[C@H](CO)C1=CC(=CC(=N1)C(=O)N)N1CC2=CC=CC(=C2CC1)C1=CC=C(C=C1)C(F)(F)F BKZXMCAIWWDHSQ-JOCHJYFZSA-N 0.000 claims 1
• PDKJRCDTWHBSKE-UHFFFAOYSA-N 6-[5-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]pyridine-2-carboxamide Chemical compound FC(C1=CC=C(C=C1)C1=C2CCN(CC2=CC=C1)C1=CC=CC(=N1)C(=O)N)(F)F PDKJRCDTWHBSKE-UHFFFAOYSA-N 0.000 claims 1
• HHIDIFCNHJJOIJ-AWEZNQCLSA-N 6-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-2-(5-cyclohexyl-3,4-dihydro-1H-isoquinolin-2-yl)pyrimidine-4-carboxamide Chemical compound NC([C@H](C)NC1=CC(=NC(=N1)N1CC2=CC=CC(=C2CC1)C1CCCCC1)C(=O)N)=O HHIDIFCNHJJOIJ-AWEZNQCLSA-N 0.000 claims 1
• ZLMXMGFQERVQES-LBPRGKRZSA-N 6-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-2-[5-[5-(trifluoromethyl)pyridin-2-yl]-3,4-dihydro-1H-isoquinolin-2-yl]pyrimidine-4-carboxamide Chemical compound NC([C@H](C)NC1=CC(=NC(=N1)N1CC2=CC=CC(=C2CC1)C1=NC=C(C=C1)C(F)(F)F)C(=O)N)=O ZLMXMGFQERVQES-LBPRGKRZSA-N 0.000 claims 1
• 208000008822 Ankylosis Diseases 0.000 claims 1
• 206010003591 Ataxia Diseases 0.000 claims 1
• 208000020925 Bipolar disease Diseases 0.000 claims 1
• 102000014914 Carrier Proteins Human genes 0.000 claims 1
• 206010008027 Cerebellar atrophy Diseases 0.000 claims 1
• 208000000094 Chronic Pain Diseases 0.000 claims 1
• 206010010904 Convulsion Diseases 0.000 claims 1
• 206010019196 Head injury Diseases 0.000 claims 1
• 206010065390 Inflammatory pain Diseases 0.000 claims 1
• 206010023198 Joint ankylosis Diseases 0.000 claims 1
• 208000036626 Mental retardation Diseases 0.000 claims 1
• 208000019695 Migraine disease Diseases 0.000 claims 1
• 208000016285 Movement disease Diseases 0.000 claims 1
• SBKIFLXSGDXZHF-UHFFFAOYSA-N N-(1,2,4-thiadiazol-5-yl)-6-[5-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]pyridine-2-sulfonamide Chemical compound S1N=CN=C1NS(=O)(=O)C1=NC(=CC=C1)N1CC2=CC=CC(=C2CC1)C1=CC=C(C=C1)C(F)(F)F SBKIFLXSGDXZHF-UHFFFAOYSA-N 0.000 claims 1
• 208000028389 Nerve injury Diseases 0.000 claims 1
• 208000009205 Tinnitus Diseases 0.000 claims 1
• LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims 1
• 208000005298 acute pain Diseases 0.000 claims 1
• 206010003119 arrhythmia Diseases 0.000 claims 1
• 238000003556 assay Methods 0.000 claims 1
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims 1
• KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 claims 1
• 108091008324 binding proteins Proteins 0.000 claims 1
• 208000028683 bipolar I disease Diseases 0.000 claims 1
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
• 229940126208 compound 22 Drugs 0.000 claims 1
• 229940125833 compound 23 Drugs 0.000 claims 1
• 229940125961 compound 24 Drugs 0.000 claims 1
• 229940125846 compound 25 Drugs 0.000 claims 1
• 229940125851 compound 27 Drugs 0.000 claims 1
• 229940127204 compound 29 Drugs 0.000 claims 1
• 229940125877 compound 31 Drugs 0.000 claims 1
• 229940125878 compound 36 Drugs 0.000 claims 1
• 230000036461 convulsion Effects 0.000 claims 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 239000012634 fragment Substances 0.000 claims 1
• 208000014617 hemorrhoid Diseases 0.000 claims 1
• 208000028867 ischemia Diseases 0.000 claims 1
• 230000002197 limbic effect Effects 0.000 claims 1
• 238000002690 local anesthesia Methods 0.000 claims 1
• 239000012528 membrane Substances 0.000 claims 1
• 206010027599 migraine Diseases 0.000 claims 1
• 210000003205 muscle Anatomy 0.000 claims 1
• 230000008764 nerve damage Effects 0.000 claims 1
• 208000004296 neuralgia Diseases 0.000 claims 1
• 230000004770 neurodegeneration Effects 0.000 claims 1
• 208000015122 neurodegenerative disease Diseases 0.000 claims 1
• 208000021722 neuropathic pain Diseases 0.000 claims 1
• 238000009116 palliative therapy Methods 0.000 claims 1
• 230000001314 paroxysmal effect Effects 0.000 claims 1
• 102000004169 proteins and genes Human genes 0.000 claims 1
• 108090000623 proteins and genes Proteins 0.000 claims 1
• 125000004076 pyridyl group Chemical group 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 238000000163 radioactive labelling Methods 0.000 claims 1
• 238000012216 screening Methods 0.000 claims 1
• 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
• 231100000886 tinnitus Toxicity 0.000 claims 1
• 125000004306 triazinyl group Chemical group 0.000 claims 1