MX2013001363A - N- ((6-amino-piridin-3-il)-metil) -heteroaril-carboxamidas como inhibidoras de calicreina de plasma. - Google Patents

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Publication number

MX2013001363A

MX2013001363A MX2013001363A MX2013001363A MX2013001363A MX 2013001363 A MX2013001363 A MX 2013001363A MX 2013001363 A MX2013001363 A MX 2013001363A MX 2013001363 A MX2013001363 A MX 2013001363A MX 2013001363 A MX2013001363 A MX 2013001363A

Authority

MX

Mexico

Prior art keywords

carbon atoms

methyl

amino

alkyl

pyridin

Prior art date

2010-08-04

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• 108090000113 Plasma Kallikrein Proteins 0.000 title claims description 38
• 102000003827 Plasma Kallikrein Human genes 0.000 title claims description 36
• 239000003112 inhibitor Substances 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 260
• 150000003839 salts Chemical group 0.000 claims abstract description 54
• 239000003814 drug Substances 0.000 claims abstract description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 1018
• 125000000217 alkyl group Chemical group 0.000 claims description 328
• -1 (6-amino-2,4-dimethyl-pyridin-3-yl) -methyl Chemical group 0.000 claims description 234
• 229910052799 carbon Inorganic materials 0.000 claims description 234
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 193
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 179
• 229910052736 halogen Inorganic materials 0.000 claims description 161
• 150000002367 halogens Chemical class 0.000 claims description 161
• 125000004122 cyclic group Chemical group 0.000 claims description 139
• 125000003545 alkoxy group Chemical group 0.000 claims description 135
• 229910052757 nitrogen Inorganic materials 0.000 claims description 130
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 122
• 229910052760 oxygen Inorganic materials 0.000 claims description 122
• 239000001301 oxygen Substances 0.000 claims description 122
• 238000000034 method Methods 0.000 claims description 97
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 91
• 229910052717 sulfur Inorganic materials 0.000 claims description 91
• 239000011593 sulfur Substances 0.000 claims description 91
• 125000001188 haloalkyl group Chemical group 0.000 claims description 90
• 125000003118 aryl group Chemical group 0.000 claims description 87
• 125000001424 substituent group Chemical group 0.000 claims description 76
• 125000005842 heteroatom Chemical group 0.000 claims description 73
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 71
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 69
• 125000006413 ring segment Chemical group 0.000 claims description 65
• 125000000623 heterocyclic group Chemical group 0.000 claims description 64
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 60
• 125000002947 alkylene group Chemical group 0.000 claims description 59
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 57
• 239000001257 hydrogen Substances 0.000 claims description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 56
• 125000004434 sulfur atom Chemical group 0.000 claims description 55
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 44
• 150000001721 carbon Chemical group 0.000 claims description 41
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
• 201000010099 disease Diseases 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 31
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 31
• 125000000304 alkynyl group Chemical group 0.000 claims description 30
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 30
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 30
• 229920006395 saturated elastomer Polymers 0.000 claims description 30
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 28
• 125000004429 atom Chemical group 0.000 claims description 28
• 125000002950 monocyclic group Chemical group 0.000 claims description 24
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 22
• 208000035475 disorder Diseases 0.000 claims description 21
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 16
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 16
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 16
• 241001139947 Mida Species 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 230000000694 effects Effects 0.000 claims description 12
• 125000005518 carboxamido group Chemical group 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
• 125000003367 polycyclic group Chemical group 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 239000011737 fluorine Chemical group 0.000 claims description 6
• 229910052731 fluorine Chemical group 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 150000002431 hydrogen Chemical group 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
• 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
• 230000002159 abnormal effect Effects 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• DCMBPCSGDIXGHI-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-2-[(4-methoxyphenyl)methyl]-1,3-oxazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1CC1=NC(C(=O)NCC=2C(=NC(N)=CC=2C)C)=CO1 DCMBPCSGDIXGHI-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• BAVNYPNHVRRHET-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-3-benzyl-1,2-oxazole-5-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CC(CC=2C=CC=CC=2)=NO1 BAVNYPNHVRRHET-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 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 2
• 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 2
• UQNKWXZAHWAEIU-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-(3,4-dihydro-2h-1,5-benzodioxepin-6-ylmethyl)pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=3OCCCOC=3C=CC=2)N=C1 UQNKWXZAHWAEIU-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• ARQXIEWAUSQQHM-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(2-chlorophenyl)methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C(=CC=CC=2)Cl)N=C1 ARQXIEWAUSQQHM-UHFFFAOYSA-N 0.000 claims description 2
• WKOPMVAENVMDCB-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(2-cyanophenyl)methyl]indole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(C1=CC=CC=C11)=CN1CC1=CC=CC=C1C#N WKOPMVAENVMDCB-UHFFFAOYSA-N 0.000 claims description 2
• MGSHKJBZVVLKLV-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(2-methyl-1,3-thiazol-4-yl)methyl]pyrazole-4-carboxamide Chemical compound S1C(C)=NC(CN2N=CC(=C2)C(=O)NCC=2C(=NC(N)=CC=2C)C)=C1 MGSHKJBZVVLKLV-UHFFFAOYSA-N 0.000 claims description 2
• BYZNGWXDOMLVBH-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(2-methylquinolin-6-yl)methyl]triazole-4-carboxamide Chemical compound C1=CC2=NC(C)=CC=C2C=C1CN(N=N1)C=C1C(=O)NCC1=C(C)C=C(N)N=C1C BYZNGWXDOMLVBH-UHFFFAOYSA-N 0.000 claims description 2
• UTAJKCOBLAFYDW-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(3,5-dimethoxyphenyl)methyl]pyrazole-4-carboxamide Chemical compound COC1=CC(OC)=CC(CN2N=CC(=C2)C(=O)NCC=2C(=NC(N)=CC=2C)C)=C1 UTAJKCOBLAFYDW-UHFFFAOYSA-N 0.000 claims description 2
• GHBUWRIQURZTTE-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(3-carbamoylphenyl)methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=C(C=CC=2)C(N)=O)N=C1 GHBUWRIQURZTTE-UHFFFAOYSA-N 0.000 claims description 2
• JKQQCHADIMQVBM-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(3-cyanophenyl)methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=C(C=CC=2)C#N)N=C1 JKQQCHADIMQVBM-UHFFFAOYSA-N 0.000 claims description 2
• ADHPVJPGQKBDKM-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(3-fluorophenyl)methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=C(F)C=CC=2)N=C1 ADHPVJPGQKBDKM-UHFFFAOYSA-N 0.000 claims description 2
• BCZGTKJOMVDJJZ-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(3-pyrazol-1-ylphenyl)methyl]triazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(N=N1)=CN1CC1=CC=CC(N2N=CC=C2)=C1 BCZGTKJOMVDJJZ-UHFFFAOYSA-N 0.000 claims description 2
• NUMQRUYULXVQRY-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(3-pyrrolidin-1-ylphenyl)methyl]-1,2,4-triazole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=NN(CC=2C=C(C=CC=2)N2CCCC2)C=N1 NUMQRUYULXVQRY-UHFFFAOYSA-N 0.000 claims description 2
• OMKHCIFLCNZFGN-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(4-cyanophenyl)methyl]pyrazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=CN(CC=2C=CC(=CC=2)C#N)N=C1 OMKHCIFLCNZFGN-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• MHSBTTJCQQJZNU-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(4-phenoxyphenyl)methyl]triazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(N=N1)=CN1CC(C=C1)=CC=C1OC1=CC=CC=C1 MHSBTTJCQQJZNU-UHFFFAOYSA-N 0.000 claims description 2
• SDKNXFXFIWAGHW-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(4-pyrazol-1-ylphenyl)methyl]imidazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C(N=C1)=CN1CC1=CC=C(N2N=CC=C2)C=C1 SDKNXFXFIWAGHW-UHFFFAOYSA-N 0.000 claims description 2
• CCLJREZEJQOIAB-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[(6-methylpyridin-2-yl)methyl]pyrazole-4-carboxamide Chemical compound CC1=CC=CC(CN2N=CC(=C2)C(=O)NCC=2C(=NC(N)=CC=2C)C)=N1 CCLJREZEJQOIAB-UHFFFAOYSA-N 0.000 claims description 2
• GISSAZULDJGQMV-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[3-methoxy-4-(pyrazol-1-ylmethyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound C=1C=C(CN2N=CC=C2)C(OC)=CC=1CN(N=C1)C=C1C(=O)NCC1=C(C)C=C(N)N=C1C GISSAZULDJGQMV-UHFFFAOYSA-N 0.000 claims description 2
• HIKVSELABJYTAG-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound CC1=NOC(C=2C=CC(CN3N=CC(=C3)C(=O)NCC=3C(=NC(N)=CC=3C)C)=CC=2)=N1 HIKVSELABJYTAG-UHFFFAOYSA-N 0.000 claims description 2
• JVJHGRCLLMUDAN-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-(dimethylsulfamoyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CN1N=CC(C(=O)NCC=2C(=NC(N)=CC=2C)C)=C1 JVJHGRCLLMUDAN-UHFFFAOYSA-N 0.000 claims description 2
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• DSOFMKFSFNBAPY-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=CC(C(=O)NCC=2C(=NC(N)=CC=2C)C)=C1 DSOFMKFSFNBAPY-UHFFFAOYSA-N 0.000 claims description 2
• VDVDOLCDTIHJHO-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-1-benzyl-1,2,4-triazole-3-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=NN(CC=2C=CC=CC=2)C=N1 VDVDOLCDTIHJHO-UHFFFAOYSA-N 0.000 claims description 2
• HQQHQZXVVZJXRZ-UHFFFAOYSA-N n-[(6-amino-2,4-dimethylpyridin-3-yl)methyl]-2-benzyl-1,3-oxazole-4-carboxamide Chemical compound CC1=CC(N)=NC(C)=C1CNC(=O)C1=COC(CC=2C=CC=CC=2)=N1 HQQHQZXVVZJXRZ-UHFFFAOYSA-N 0.000 claims description 2
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