JP2013532692A5

JP2013532692A5 -

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Publication number: JP2013532692A5
Authority: JP; Japan
Prior art keywords: alkyl; carbonyl; piperidin; piperidine; picolinamide
Prior art date: 2011-07-29
Legal status : Granted

Application number

JP2013522013A

Other languages

English (en)

Japanese (ja)

Other versions

JP2013532692A (ja

JP5889895B2 (ja

Filing date

2011-07-29

Publication date

2014-09-04

2011-07-29 Application filed filed Critical

2011-07-29 Priority claimed from PCT/US2011/046019 external-priority patent/WO2012016217A1/en

2013-08-19 Publication of JP2013532692A publication Critical patent/JP2013532692A/ja

2014-09-04 Publication of JP2013532692A5 publication Critical patent/JP2013532692A5/ja

2016-03-22 Application granted granted Critical

2016-03-22 Publication of JP5889895B2 publication Critical patent/JP5889895B2/ja

Status Expired - Fee Related legal-status Critical Current

2031-07-29 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims description 252
150000001875 compounds Chemical class 0.000 claims description 134
-1 methoxy, ethoxy Chemical group 0.000 claims description 100
150000003839 salts Chemical class 0.000 claims description 50
239000012453 solvate Substances 0.000 claims description 43
150000001204 N-oxides Chemical class 0.000 claims description 42
229910052799 carbon Inorganic materials 0.000 claims description 23
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000004122 cyclic group Chemical group 0.000 claims description 22
125000001188 haloalkyl group Chemical group 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 14
239000008194 pharmaceutical composition Substances 0.000 claims description 11
125000005549 heteroarylene group Chemical group 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000000732 arylene group Chemical group 0.000 claims description 7
208000006011 Stroke Diseases 0.000 claims description 6
YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims description 5
CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims description 5
229940106189 ceramide Drugs 0.000 claims description 5
ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims description 5
VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
102000004201 Ceramidases Human genes 0.000 claims description 4
108090000751 Ceramidases Proteins 0.000 claims description 4
206010013801 Duchenne Muscular Dystrophy Diseases 0.000 claims description 4
206010019280 Heart failures Diseases 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
208000028867 ischemia Diseases 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 4
206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
230000002503 metabolic effect Effects 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
208000011580 syndromic disease Diseases 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 claims description 2
ISSLZKSSYLRMSG-JDXGNMNLSA-N 5-[(3S,4S)-4-(4-cyanophenoxy)-3-fluoropiperidine-1-carbonyl]-N-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]pyridine-2-carboxamide Chemical compound O([C@H]1CCN(C[C@@H]1F)C(=O)C=1C=NC(=CC=1)C(=O)NC1CCN(CC=2C=CC(=CC=2)C#N)CC1)C1=CC=C(C#N)C=C1 ISSLZKSSYLRMSG-JDXGNMNLSA-N 0.000 claims description 2
KMRPXMWIZLSCAG-IZZNHLLZSA-N 5-[4-[(4-fluorophenyl)methyl]piperazine-1-carbonyl]-n-[(3s,4r)-3-fluoro-1-(pyridin-4-ylmethyl)piperidin-4-yl]pyridine-2-carboxamide Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2N=CC(=CC=2)C(=O)N2CCN(CC=3C=CC(F)=CC=3)CC2)F)N1CC1=CC=NC=C1 KMRPXMWIZLSCAG-IZZNHLLZSA-N 0.000 claims description 2
SSXKELDQHCLBAC-VQTJNVASSA-N 5-[4-[(4-fluorophenyl)methyl]piperazine-1-carbonyl]-n-[(3s,4r)-3-fluoropiperidin-4-yl]pyridine-2-carboxamide Chemical compound F[C@H]1CNCC[C@H]1NC(=O)C1=CC=C(C(=O)N2CCN(CC=3C=CC(F)=CC=3)CC2)C=N1 SSXKELDQHCLBAC-VQTJNVASSA-N 0.000 claims description 2
206010002383 Angina Pectoris Diseases 0.000 claims description 2
201000001320 Atherosclerosis Diseases 0.000 claims description 2
WSHUFJLKIMPHGV-FQLXRVMXSA-N CC1=CC=C(C=C1)C(=O)C2CCN(CC2)C(=O)C3=CN=C(C=C3)C(=O)N[C@@H]4CCN(C[C@H]4F)CC5=CC=C(C=C5)C#N Chemical compound CC1=CC=C(C=C1)C(=O)C2CCN(CC2)C(=O)C3=CN=C(C=C3)C(=O)N[C@@H]4CCN(C[C@H]4F)CC5=CC=C(C=C5)C#N WSHUFJLKIMPHGV-FQLXRVMXSA-N 0.000 claims description 2
ODBQSZFTJYTYMN-FQLXRVMXSA-N CC1=CC=C(C=C1)OC2CCN(CC2)C(=O)C3=CN=C(C=C3)C(=O)N[C@@H]4CCN(C[C@H]4F)CC5=CC=C(C=C5)C#N Chemical compound CC1=CC=C(C=C1)OC2CCN(CC2)C(=O)C3=CN=C(C=C3)C(=O)N[C@@H]4CCN(C[C@H]4F)CC5=CC=C(C=C5)C#N ODBQSZFTJYTYMN-FQLXRVMXSA-N 0.000 claims description 2
206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 2
206010012289 Dementia Diseases 0.000 claims description 2
229920002527 Glycogen Polymers 0.000 claims description 2
101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 claims description 2
206010022562 Intermittent claudication Diseases 0.000 claims description 2
208000010428 Muscle Weakness Diseases 0.000 claims description 2
206010028372 Muscular weakness Diseases 0.000 claims description 2
208000036572 Myoclonic epilepsy Diseases 0.000 claims description 2
208000002033 Myoclonus Diseases 0.000 claims description 2
206010053648 Vascular occlusion Diseases 0.000 claims description 2
230000003213 activating effect Effects 0.000 claims description 2
208000008445 altitude sickness Diseases 0.000 claims description 2
235000014113 dietary fatty acids Nutrition 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
201000009028 early myoclonic encephalopathy Diseases 0.000 claims description 2
229930195729 fatty acid Natural products 0.000 claims description 2
239000000194 fatty acid Substances 0.000 claims description 2
150000004665 fatty acids Chemical class 0.000 claims description 2
230000004190 glucose uptake Effects 0.000 claims description 2
229940096919 glycogen Drugs 0.000 claims description 2
208000021156 intermittent vascular claudication Diseases 0.000 claims description 2
208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 2
208000010125 myocardial infarction Diseases 0.000 claims description 2
XSTWHJANPVSKRP-FQLXRVMXSA-N n-[(3r,4r)-1-[(4-cyano-3-fluorophenyl)methyl]-3-fluoropiperidin-4-yl]-6-[4-(4-methoxybenzoyl)piperidine-1-carbonyl]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C(=O)C=2N=CC(=CC=2)C(=O)N[C@H]2[C@@H](CN(CC=3C=C(F)C(C#N)=CC=3)CC2)F)CC1 XSTWHJANPVSKRP-FQLXRVMXSA-N 0.000 claims description 2
BFKLKEDGPVUXEU-VSGBNLITSA-N n-[(3r,4r)-1-[(4-cyanophenyl)methyl]-3-fluoropiperidin-4-yl]-6-[4-[4-(trifluoromethylsulfonyl)phenoxy]piperidine-1-carbonyl]pyridine-3-carboxamide Chemical compound C([C@H]([C@@H](CC1)NC(=O)C=2C=NC(=CC=2)C(=O)N2CCC(CC2)OC=2C=CC(=CC=2)S(=O)(=O)C(F)(F)F)F)N1CC1=CC=C(C#N)C=C1 BFKLKEDGPVUXEU-VSGBNLITSA-N 0.000 claims description 2
MWVAIOSVWVODAN-VSGBNLITSA-N n-[(3r,4r)-3-fluoro-1-[[4-(trifluoromethoxy)phenyl]methyl]piperidin-4-yl]-5-[4-(4-methylsulfonylbenzoyl)piperidine-1-carbonyl]pyridine-2-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1CCN(C(=O)C=2C=NC(=CC=2)C(=O)N[C@H]2[C@@H](CN(CC=3C=CC(OC(F)(F)F)=CC=3)CC2)F)CC1 MWVAIOSVWVODAN-VSGBNLITSA-N 0.000 claims description 2
QYKFEEHGZRXLOV-VSGBNLITSA-N n-[(3r,4r)-3-fluoro-1-[[4-(trifluoromethoxy)phenyl]methyl]piperidin-4-yl]-5-[4-(4-methylsulfonylphenoxy)piperidine-1-carbonyl]pyridine-2-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1CCN(C(=O)C=2C=NC(=CC=2)C(=O)N[C@H]2[C@@H](CN(CC=3C=CC(OC(F)(F)F)=CC=3)CC2)F)CC1 QYKFEEHGZRXLOV-VSGBNLITSA-N 0.000 claims description 2
QFCGCJFUXOLOOW-RRPNLBNLSA-N n-[(3s,4r)-1-[(4-chlorophenyl)methyl]-3-fluoropiperidin-4-yl]-5-[4-[(4-fluorophenyl)methyl]piperazine-1-carbonyl]pyridine-2-carboxamide Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2N=CC(=CC=2)C(=O)N2CCN(CC=3C=CC(F)=CC=3)CC2)F)N1CC1=CC=C(Cl)C=C1 QFCGCJFUXOLOOW-RRPNLBNLSA-N 0.000 claims description 2
QECRHJAQOQEILO-IZZNHLLZSA-N n-[(3s,4r)-3-fluoro-1-[(2-methyl-1,3-thiazol-4-yl)methyl]piperidin-4-yl]-6-[4-(4-methoxybenzoyl)piperidine-1-carbonyl]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C(=O)C=2N=CC(=CC=2)C(=O)N[C@H]2[C@H](CN(CC=3N=C(C)SC=3)CC2)F)CC1 QECRHJAQOQEILO-IZZNHLLZSA-N 0.000 claims description 2
HJLLFICFQXAIAT-IZZNHLLZSA-N n-[(3s,4r)-3-fluoro-1-[(5-methyl-1,2-oxazol-3-yl)methyl]piperidin-4-yl]-6-[4-(4-methoxybenzoyl)piperidine-1-carbonyl]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C(=O)C=2N=CC(=CC=2)C(=O)N[C@H]2[C@H](CN(CC3=NOC(C)=C3)CC2)F)CC1 HJLLFICFQXAIAT-IZZNHLLZSA-N 0.000 claims description 2
LEUSDRGCPVXECX-VMPREFPWSA-N n-[(3s,4s)-1-[(4-cyanophenyl)methyl]-3-fluoropiperidin-4-yl]-6-[4-(4-methoxybenzoyl)piperidine-1-carbonyl]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C(=O)C=2N=CC(=CC=2)C(=O)N[C@@H]2[C@H](CN(CC=3C=CC(=CC=3)C#N)CC2)F)CC1 LEUSDRGCPVXECX-VMPREFPWSA-N 0.000 claims description 2
FKPPDDDQZXPHNG-UHFFFAOYSA-N n-[1-[(3-fluoro-4-methoxyphenyl)methyl]piperidin-4-yl]-6-[4-(4-pyrrolidin-1-ylbenzoyl)piperidine-1-carbonyl]pyridine-3-carboxamide Chemical compound C1=C(F)C(OC)=CC=C1CN1CCC(NC(=O)C=2C=NC(=CC=2)C(=O)N2CCC(CC2)C(=O)C=2C=CC(=CC=2)N2CCCC2)CC1 FKPPDDDQZXPHNG-UHFFFAOYSA-N 0.000 claims description 2
230000008816 organ damage Effects 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
230000037361 pathway Effects 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
208000024891 symptom Diseases 0.000 claims description 2
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
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125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
125000001424 substituent group Chemical group 0.000 claims 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
208000010444 Acidosis Diseases 0.000 claims 1
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
230000007950 acidosis Effects 0.000 claims 1
208000026545 acidosis disease Diseases 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
210000004556 brain Anatomy 0.000 claims 1
210000004351 coronary vessel Anatomy 0.000 claims 1
239000000835 fiber Substances 0.000 claims 1
150000004677 hydrates Chemical class 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
230000002438 mitochondrial effect Effects 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
238000000034 method Methods 0.000 description 50
239000000126 substance Substances 0.000 description 45
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210000004027 cell Anatomy 0.000 description 16
0 C*[C@](C)(*)N=*C Chemical compound C*[C@](C)(*)N=*C 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
230000006378 damage Effects 0.000 description 4
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IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
GJHZOKKWVMPWMH-UHFFFAOYSA-N 2-N-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]pyridine-2,5-dicarboxamide Chemical compound N1=C(C=CC(=C1)C(=O)N)C(=O)NC1CCN(CC1)CC1=CC=C(C=C1)C#N GJHZOKKWVMPWMH-UHFFFAOYSA-N 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
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KILULKZXXSWNCI-UHFFFAOYSA-N N-[4-(4-cyanophenoxy)cyclohexyl]-5-[4-(4-fluorobenzoyl)piperidine-1-carbonyl]pyridine-2-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(C(=O)C=2C=NC(=CC=2)C(=O)NC2CCC(CC2)OC=2C=CC(=CC=2)C#N)CC1 KILULKZXXSWNCI-UHFFFAOYSA-N 0.000 description 2
BZCVQNXMJJLXPG-UHFFFAOYSA-N N-[4-(4-cyanophenoxy)cyclohexyl]-5-[4-(4-fluorophenoxy)piperidine-1-carbonyl]pyridine-2-carboxamide Chemical compound C1=CC(F)=CC=C1OC1CCN(C(=O)C=2C=NC(=CC=2)C(=O)NC2CCC(CC2)OC=2C=CC(=CC=2)C#N)CC1 BZCVQNXMJJLXPG-UHFFFAOYSA-N 0.000 description 2
QVGHVUBOGYEDKB-UHFFFAOYSA-N N-[4-(4-cyanophenoxy)cyclohexyl]-5-[4-(4-methoxyphenoxy)piperidine-1-carbonyl]pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1OC1CCN(C(=O)C=2C=NC(=CC=2)C(=O)NC2CCC(CC2)OC=2C=CC(=CC=2)C#N)CC1 QVGHVUBOGYEDKB-UHFFFAOYSA-N 0.000 description 2
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BKCJRBLXKYEYHK-UHFFFAOYSA-N 1-[(4-cyanophenyl)methyl]-n-[5-[4-[(4-fluorophenyl)methyl]piperazine-1-carbonyl]pyridin-2-yl]piperidine-4-carboxamide Chemical compound C1=CC(F)=CC=C1CN1CCN(C(=O)C=2C=NC(NC(=O)C3CCN(CC=4C=CC(=CC=4)C#N)CC3)=CC=2)CC1 BKCJRBLXKYEYHK-UHFFFAOYSA-N 0.000 description 1
GFDOYTAWIKLKSA-UHFFFAOYSA-N 2-n,5-n-bis(1-benzylpiperidin-4-yl)pyridine-2,5-dicarboxamide Chemical compound C=1C=C(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)N=CC=1C(=O)NC(CC1)CCN1CC1=CC=CC=C1 GFDOYTAWIKLKSA-UHFFFAOYSA-N 0.000 description 1
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CWIOPRLBOMZPKA-UHFFFAOYSA-N 2-n-(1-benzylpiperidin-4-yl)-5-n-(4-phenylphenyl)pyridine-2,5-dicarboxamide Chemical compound C=1C=C(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)N=CC=1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 CWIOPRLBOMZPKA-UHFFFAOYSA-N 0.000 description 1
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DENRPACRNJYZDG-UHFFFAOYSA-N 2-n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-5-n-[2-(4-fluorophenoxy)ethyl]pyridine-2,5-dicarboxamide Chemical compound C1=CC(F)=CC=C1OCCNC(=O)C1=CC=C(C(=O)NC2CCN(CC=3C=CC(=CC=3)C#N)CC2)N=C1 DENRPACRNJYZDG-UHFFFAOYSA-N 0.000 description 1
NAUIMQDUCLBJRJ-UHFFFAOYSA-N 2-n-[2-[(4-cyanophenyl)methyl]-3,4-dihydro-1h-isoquinolin-7-yl]-5-n-[(4-fluorophenyl)methyl]pyridine-2,5-dicarboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=C(C(=O)NC=2C=C3CN(CC=4C=CC(=CC=4)C#N)CCC3=CC=2)N=C1 NAUIMQDUCLBJRJ-UHFFFAOYSA-N 0.000 description 1
PTNAVJCDQOQYQW-BXWFABGCSA-N 4-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[2-[2-[2-(3-amino-3-oxopropoxy)ethoxy]ethoxy]ethoxy]ethyl]butanamide Chemical compound NC(=O)CCOCCOCCOCCOCCNC(=O)CCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12 PTNAVJCDQOQYQW-BXWFABGCSA-N 0.000 description 1
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JP2013522013A 2010-07-29 2011-07-29 Ａｍｐｋ活性化複素環化合物およびその使用方法 Expired - Fee Related JP5889895B2 (ja)