ES2542764T3 - N-((6-amino-piridin-3-il)metil)-heteroaril-carboxamidas como inhibidores de la calicreína plasmática - Google Patents

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Publication number

ES2542764T3

ES2542764T3 ES11745519.6T ES11745519T ES2542764T3 ES 2542764 T3 ES2542764 T3 ES 2542764T3 ES 11745519 T ES11745519 T ES 11745519T ES 2542764 T3 ES2542764 T3 ES 2542764T3

Authority

ES

Spain

Prior art keywords

methyl

amino

carboxamide

dimethylpyridin

alkyl

Prior art date

2010-08-04

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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• -1 (6-amino-pyridin-3-yl) methyl Chemical group 0.000 title claims description 156
• 102000003827 Plasma Kallikrein Human genes 0.000 title claims description 34
• 108090000113 Plasma Kallikrein Proteins 0.000 title claims description 34
• 239000003112 inhibitor Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 401
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 207
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 182
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 167
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 167
• 150000002367 halogens Chemical group 0.000 claims abstract description 154
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 149
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 137
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 126
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 126
• 239000001301 oxygen Substances 0.000 claims abstract description 126
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 96
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 96
• 239000011593 sulfur Substances 0.000 claims abstract description 96
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 93
• 125000006413 ring segment Chemical group 0.000 claims abstract description 83
• 125000001424 substituent group Chemical group 0.000 claims abstract description 79
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 74
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 73
• 125000003118 aryl group Chemical group 0.000 claims abstract description 68
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 66
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 64
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 63
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 61
• 239000001257 hydrogen Substances 0.000 claims abstract description 61
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 60
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 59
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 53
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 48
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 46
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 46
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 46
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 40
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 34
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 33
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 32
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 32
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 32
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims abstract description 26
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 26
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 25
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 19
• 125000006642 (C1-C6) cyanoalkyl group Chemical group 0.000 claims abstract description 17
• 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 17
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 16
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract description 16
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 11
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
• 125000005843 halogen group Chemical group 0.000 claims abstract 13
• 238000000034 method Methods 0.000 claims description 266
• 150000003839 salts Chemical group 0.000 claims description 53
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 49
• 125000002950 monocyclic group Chemical group 0.000 claims description 37
• 201000010099 disease Diseases 0.000 claims description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 208000035475 disorder Diseases 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 17
• 238000011282 treatment Methods 0.000 claims description 17
• 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 14
• 230000000694 effects Effects 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000003367 polycyclic group Chemical group 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 150000003857 carboxamides Chemical class 0.000 claims description 7
• QWLJELCBJXPMEB-UHFFFAOYSA-N n-[[6-amino-2-methyl-4-(1,3-oxazol-2-ylmethoxy)pyridin-3-yl]methyl]-1-benzyltriazole-4-carboxamide Chemical compound C=1N(CC=2C=CC=CC=2)N=NC=1C(=O)NCC=1C(C)=NC(N)=CC=1OCC1=NC=CO1 QWLJELCBJXPMEB-UHFFFAOYSA-N 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 5
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• GOLHZPOXCLTFRB-UHFFFAOYSA-N furan-3-carboxamide Chemical compound NC(=O)C=1C=COC=1 GOLHZPOXCLTFRB-UHFFFAOYSA-N 0.000 claims description 4
• LBJVICZKRMLNCJ-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(2-hydroxy-1-phenylethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(C(CO)C=2C=CC=CC=2)N=C1 LBJVICZKRMLNCJ-UHFFFAOYSA-N 0.000 claims description 4
• LRMLBIIGBOPUPH-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(pyridin-4-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CN=CC=2)N=C1 LRMLBIIGBOPUPH-UHFFFAOYSA-N 0.000 claims description 4
• ULUARQDPFVJPMB-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(4-methoxyphenyl)methyl]pyrazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1N=CC(C(=O)NCC=2C(=NC(N)=CC=2C)C)=C1 ULUARQDPFVJPMB-UHFFFAOYSA-N 0.000 claims description 4
• OIQHYMFFSWKLDO-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(4-phenylphenyl)methyl]triazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(N=N1)=CN1CC1=CC=C(C=2C=CC=CC=2)C=C1 OIQHYMFFSWKLDO-UHFFFAOYSA-N 0.000 claims description 4
• CWYCUONCOWMQFA-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-(cyanomethoxy)phenyl]methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CC(OCC#N)=CC=2)N=C1 CWYCUONCOWMQFA-UHFFFAOYSA-N 0.000 claims description 4
• LMXYYMDFPJEEJA-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-(cyclopropylcarbamoylamino)phenyl]methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CC(NC(=O)NC3CC3)=CC=2)N=C1 LMXYYMDFPJEEJA-UHFFFAOYSA-N 0.000 claims description 4
• ACHRVCHEYBBWEO-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-(hydroxymethyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CC(CO)=CC=2)N=C1 ACHRVCHEYBBWEO-UHFFFAOYSA-N 0.000 claims description 4
• UYHOBBIURQGOSN-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-(propan-2-ylcarbamoyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1CN1N=CC(C(=O)NCC=2C(=NC(N)=CC=2C)C)=C1 UYHOBBIURQGOSN-UHFFFAOYSA-N 0.000 claims description 4
• OIUPJAOKWHMNEH-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-[(2,5-dioxopyrrolidin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CC(CN3C(CCC3=O)=O)=CC=2)N=C1 OIUPJAOKWHMNEH-UHFFFAOYSA-N 0.000 claims description 4
• AXZFTDBLZQVAAF-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-3-benzyl-1,2,4-oxadiazole-5-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=NC(CC=2C=CC=CC=2)=NO1 AXZFTDBLZQVAAF-UHFFFAOYSA-N 0.000 claims description 4
• ZNFBXTCTSGUQHW-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-5-benzyl-1,3,4-oxadiazole-2-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(O1)=NN=C1CC1=CC=CC=C1 ZNFBXTCTSGUQHW-UHFFFAOYSA-N 0.000 claims description 4
• CHSCMCOWGWDCQR-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-5-benzyl-1,3-oxazole-2-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(O1)=NC=C1CC1=CC=CC=C1 CHSCMCOWGWDCQR-UHFFFAOYSA-N 0.000 claims description 4
• ZUDXQKDTYUIMKT-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-5-benzyl-1-methyl-1,2,4-triazole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=NN(C)C(CC=2C=CC=CC=2)=N1 ZUDXQKDTYUIMKT-UHFFFAOYSA-N 0.000 claims description 4
• DTPXJVVBPLQWBN-UHFFFAOYSA-N n-[(6-amino-4-chloro-2-methylpyridin-3-yl)methyl]-1-benzylpyrazole-4-carboxamide Chemical compound CC1=NC(N)=CC(Cl)=C1CNC(=O)C1=CN(CC=2C=CC=CC=2)N=C1 DTPXJVVBPLQWBN-UHFFFAOYSA-N 0.000 claims description 4
• ZRENHNGQWBVIAI-UHFFFAOYSA-N n-[(6-amino-4-cyclohexyloxy-2-methylpyridin-3-yl)methyl]-1-benzylpyrazole-4-carboxamide Chemical compound C1=NN(CC=2C=CC=CC=2)C=C1C(=O)NCC=1C(C)=NC(N)=CC=1OC1CCCCC1 ZRENHNGQWBVIAI-UHFFFAOYSA-N 0.000 claims description 4
• LNNAHRUKLVTDBH-UHFFFAOYSA-N n-[(6-amino-4-methoxy-2-methylpyridin-3-yl)methyl]-1-benzylpyrazole-4-carboxamide Chemical compound COC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CC=CC=2)N=C1 LNNAHRUKLVTDBH-UHFFFAOYSA-N 0.000 claims description 4
• FOEOJKNUMDSKMO-UHFFFAOYSA-N 2-[4-[[4-[(6-amino-2,4-dimethylpyridin-3-yl)methylcarbamoyl]pyrazol-1-yl]methyl]phenoxy]acetic acid Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CC(OCC(O)=O)=CC=2)N=C1 FOEOJKNUMDSKMO-UHFFFAOYSA-N 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• JYXGVWDNVCBLEQ-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(1,2-benzoxazol-3-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C3=CC=CC=C3ON=2)N=C1 JYXGVWDNVCBLEQ-UHFFFAOYSA-N 0.000 claims description 3
• YZMKHZZIPJZJTR-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(1,3-benzodioxol-5-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=C3OCOC3=CC=2)N=C1 YZMKHZZIPJZJTR-UHFFFAOYSA-N 0.000 claims description 3
• JYZQONPRENTMRB-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(1,3-benzothiazol-2-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2SC3=CC=CC=C3N=2)N=C1 JYZQONPRENTMRB-UHFFFAOYSA-N 0.000 claims description 3
• YZWTUMFQPSCKHC-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(1-benzofuran-2-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2OC3=CC=CC=C3C=2)N=C1 YZWTUMFQPSCKHC-UHFFFAOYSA-N 0.000 claims description 3
• WPZSHZWTNBNXEO-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(1-methylindol-5-yl)sulfonylpyrrole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(S(=O)(=O)C=2C=C3C=CN(C)C3=CC=2)C=C1 WPZSHZWTNBNXEO-UHFFFAOYSA-N 0.000 claims description 3
• DTLRUZKFZYHOBO-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(1-phenylethyl)pyrazole-4-carboxamide Chemical compound C1=C(C(=O)NCC=2C(=NC(N)=CC=2C)C)C=NN1C(C)C1=CC=CC=C1 DTLRUZKFZYHOBO-UHFFFAOYSA-N 0.000 claims description 3
• RFWGXKVXWYEDIE-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(3-cyanophenyl)sulfonylpyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(S(=O)(=O)C=2C=C(C=CC=2)C#N)N=C1 RFWGXKVXWYEDIE-UHFFFAOYSA-N 0.000 claims description 3
• XBDPGGCIEKUDKJ-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(3-methoxyphenyl)sulfonylpyrrole-3-carboxamide Chemical compound COC1=CC=CC(S(=O)(=O)N2C=C(C=C2)C(=O)NCC=2C(=NC(N)=CC=2C)C)=C1 XBDPGGCIEKUDKJ-UHFFFAOYSA-N 0.000 claims description 3
• CFNRXFVWMJQCAJ-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(3-pyrimidin-2-ylphenyl)sulfonylpyrrole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(S(=O)(=O)C=2C=C(C=CC=2)C=2N=CC=CN=2)C=C1 CFNRXFVWMJQCAJ-UHFFFAOYSA-N 0.000 claims description 3
• WLIVFTPRFJQPPD-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(3h-benzimidazol-5-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=C3N=CNC3=CC=2)N=C1 WLIVFTPRFJQPPD-UHFFFAOYSA-N 0.000 claims description 3
• UQGMQMRTUNUSCX-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(4-phenylphenyl)sulfonylpyrrole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 UQGMQMRTUNUSCX-UHFFFAOYSA-N 0.000 claims description 3
• DOSCTASBPDFRET-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(5-chlorothiophen-2-yl)sulfonylpyrrole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(S(=O)(=O)C=2SC(Cl)=CC=2)C=C1 DOSCTASBPDFRET-UHFFFAOYSA-N 0.000 claims description 3
• CSWCXDDXKQWSRB-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(benzenesulfonyl)-2,5-dimethylpyrrole-3-carboxamide Chemical compound CC=1N(S(=O)(=O)C=2C=CC=CC=2)C(C)=CC=1C(=O)NCC1=C(C)C=C(N)N=C1C CSWCXDDXKQWSRB-UHFFFAOYSA-N 0.000 claims description 3
• BYMDCGFTGBZJBB-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(benzenesulfonyl)-4-methylpyrrole-3-carboxamide Chemical compound CC1=CN(S(=O)(=O)C=2C=CC=CC=2)C=C1C(=O)NCC1=C(C)C=C(N)N=C1C BYMDCGFTGBZJBB-UHFFFAOYSA-N 0.000 claims description 3
• HOPVDEHOWTWUDS-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(cyclohexylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC2CCCCC2)N=C1 HOPVDEHOWTWUDS-UHFFFAOYSA-N 0.000 claims description 3
• RPXMSPHMCUCZNH-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(furan-2-ylmethyl)-2,5-dimethylpyrrole-3-carboxamide Chemical compound CC=1N(CC=2OC=CC=2)C(C)=CC=1C(=O)NCC1=C(C)C=C(N)N=C1C RPXMSPHMCUCZNH-UHFFFAOYSA-N 0.000 claims description 3
• OYLJPVORLWINFY-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(imidazo[1,2-a]pyridin-2-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2N=C3C=CC=CN3C=2)N=C1 OYLJPVORLWINFY-UHFFFAOYSA-N 0.000 claims description 3
• VFUVLOZRLJAPPU-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(naphthalen-1-ylmethyl)-1,2,4-triazole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=NN(CC=2C3=CC=CC=C3C=CC=2)C=N1 VFUVLOZRLJAPPU-UHFFFAOYSA-N 0.000 claims description 3
• NLRLSHYJGRTPLS-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(naphthalen-1-ylmethyl)triazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(N=N1)=CN1CC1=CC=CC2=CC=CC=C12 NLRLSHYJGRTPLS-UHFFFAOYSA-N 0.000 claims description 3
• BOINRHSOFVSNQU-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(naphthalen-2-ylmethyl)-1,2,4-triazole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=NN(CC=2C=C3C=CC=CC3=CC=2)C=N1 BOINRHSOFVSNQU-UHFFFAOYSA-N 0.000 claims description 3
• VWGVJQZHMBOLSQ-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(naphthalen-2-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=C3C=CC=CC3=CC=2)N=C1 VWGVJQZHMBOLSQ-UHFFFAOYSA-N 0.000 claims description 3
• MBRKUBPARWQXHD-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(naphthalen-2-ylmethyl)triazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(N=N1)=CN1CC1=CC=C(C=CC=C2)C2=C1 MBRKUBPARWQXHD-UHFFFAOYSA-N 0.000 claims description 3
• UQJLGQSSCJBZFY-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(pyridin-3-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=NC=CC=2)N=C1 UQJLGQSSCJBZFY-UHFFFAOYSA-N 0.000 claims description 3
• XBPJTCIEOJFPKF-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(1-methylbenzotriazol-5-yl)methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=C3N=NN(C)C3=CC=2)N=C1 XBPJTCIEOJFPKF-UHFFFAOYSA-N 0.000 claims description 3
• MHLALIQKGDASOX-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(1-methylindol-6-yl)methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=C3N(C)C=CC3=CC=2)N=C1 MHLALIQKGDASOX-UHFFFAOYSA-N 0.000 claims description 3
• HGVKEHICKRVVTE-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(2,3-dimethyl-1h-indol-5-yl)methyl]pyrazole-4-carboxamide Chemical compound C1=C2C(C)=C(C)NC2=CC=C1CN(N=C1)C=C1C(=O)NCC1=C(C)C=C(N)N=C1C HGVKEHICKRVVTE-UHFFFAOYSA-N 0.000 claims description 3
• FFIADOLVJVDAEG-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(2,4-difluorophenyl)methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C(=CC(F)=CC=2)F)N=C1 FFIADOLVJVDAEG-UHFFFAOYSA-N 0.000 claims description 3
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• YRTJJYKZLPYTIN-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(3-pyrrolidin-1-ylphenyl)methyl]triazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(N=N1)=CN1CC1=CC=CC(N2CCCC2)=C1 YRTJJYKZLPYTIN-UHFFFAOYSA-N 0.000 claims description 3
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• OUKWTWSWNLIIED-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-(pyrazol-1-ylmethyl)phenyl]methyl]imidazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(N=C1)=CN1CC(C=C1)=CC=C1CN1N=CC=C1 OUKWTWSWNLIIED-UHFFFAOYSA-N 0.000 claims description 3
• OINOKQVNBGAIMA-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-(pyrazol-1-ylmethyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CC(CN3N=CC=C3)=CC=2)N=C1 OINOKQVNBGAIMA-UHFFFAOYSA-N 0.000 claims description 3
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• MKNQOJGNOABDKI-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-[(2-oxopyrrolidin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CC(CN3C(CCC3)=O)=CC=2)N=C1 MKNQOJGNOABDKI-UHFFFAOYSA-N 0.000 claims description 3
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