JP2007529484A - ピラゾロ［３，４−ｂ］ピリジン化合物、およびＰＤＥ４阻害剤としてのその使用 - Google Patents

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Publication number

JP2007529484A

JP2007529484A JP2007503401A JP2007503401A JP2007529484A JP 2007529484 A JP2007529484 A JP 2007529484A JP 2007503401 A JP2007503401 A JP 2007503401A JP 2007503401 A JP2007503401 A JP 2007503401A JP 2007529484 A JP2007529484 A JP 2007529484A

Authority

JP

Japan

Prior art keywords

ethyl

alkyl

methyl

pyrazolo

amino

Prior art date

2004-03-16

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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• 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title abstract description 7
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 48
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 47
• 150000001875 compounds Chemical class 0.000 claims abstract description 237
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 189
• 150000003839 salts Chemical class 0.000 claims abstract description 148
• -1 (cyclopropyl) methyl- Chemical group 0.000 claims abstract description 140
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 108
• 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 96
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 74
• 238000011282 treatment Methods 0.000 claims abstract description 37
• 230000002265 prevention Effects 0.000 claims abstract description 25
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 18
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 15
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 14
• 208000006673 asthma Diseases 0.000 claims abstract description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 13
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 13
• 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 11
• 208000026935 allergic disease Diseases 0.000 claims abstract description 11
• 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 11
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 11
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 8
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims abstract description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 267
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 131
• 229910052757 nitrogen Inorganic materials 0.000 claims description 80
• 238000000034 method Methods 0.000 claims description 75
• 125000003545 alkoxy group Chemical group 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
• 125000001424 substituent group Chemical group 0.000 claims description 64
• 229910052799 carbon Inorganic materials 0.000 claims description 61
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 52
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 239000008194 pharmaceutical composition Substances 0.000 claims description 35
• 125000005843 halogen group Chemical group 0.000 claims description 32
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 29
• 229910005965 SO 2 Inorganic materials 0.000 claims description 28
• 150000001721 carbon Chemical group 0.000 claims description 26
• 239000003814 drug Substances 0.000 claims description 25
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 22
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 229910052760 oxygen Inorganic materials 0.000 claims description 20
• 125000001153 fluoro group Chemical group F* 0.000 claims description 18
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 241000124008 Mammalia Species 0.000 claims description 16
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 16
• 229960003753 nitric oxide Drugs 0.000 claims description 16
• 235000019391 nitrogen oxide Nutrition 0.000 claims description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 13
• 241000282412 Homo Species 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 239000000460 chlorine Substances 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
• 208000012902 Nervous system disease Diseases 0.000 claims description 4
• 206010040070 Septic Shock Diseases 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 208000010877 cognitive disease Diseases 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 229940095102 methyl benzoate Drugs 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• SKCRVUYYFAJFFD-AWEZNQCLSA-N 1-ethyl-n-(2-ethylbutyl)-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound CCC(CC)CNC(=O)C1=CN=C2N(CC)N=CC2=C1N[C@@H](C)C(C)C SKCRVUYYFAJFFD-AWEZNQCLSA-N 0.000 claims description 3
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
• 208000011231 Crohn disease Diseases 0.000 claims description 3
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
• 208000025966 Neurological disease Diseases 0.000 claims description 3
• 208000002193 Pain Diseases 0.000 claims description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
• 125000004848 alkoxyethyl group Chemical group 0.000 claims description 3
• 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
• 201000008937 atopic dermatitis Diseases 0.000 claims description 3
• 210000004556 brain Anatomy 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 230000036407 pain Effects 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• JGHDUJFUFWBGAJ-OAHLLOKOSA-N 1-ethyl-4-[[(2r)-3-methylbutan-2-yl]amino]-n-[(4-methylsulfonylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@H](C)C(C)C)C=1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 JGHDUJFUFWBGAJ-OAHLLOKOSA-N 0.000 claims description 2
• LXUABLMXFLGZBW-CQSZACIVSA-N 1-ethyl-4-[[(2r)-3-methylbutan-2-yl]amino]-n-[[4-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@H](C)C(C)C)C=1C(=O)NCC1=CC=C(C(F)(F)F)C=C1 LXUABLMXFLGZBW-CQSZACIVSA-N 0.000 claims description 2
• MESNHWPZQZEXDI-NSHDSACASA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-(2-sulfamoylethyl)pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound NS(=O)(=O)CCNC(=O)C1=CN=C2N(CC)N=CC2=C1N[C@@H](C)C(C)C MESNHWPZQZEXDI-NSHDSACASA-N 0.000 claims description 2
• SWBHRHUPQOKWQV-ZDUSSCGKSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-(oxan-4-yl)pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NC1CCOCC1 SWBHRHUPQOKWQV-ZDUSSCGKSA-N 0.000 claims description 2
• MLZCHAHLAFBWMP-LSLKUGRBSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-(oxolan-2-ylmethyl)pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1CCCO1 MLZCHAHLAFBWMP-LSLKUGRBSA-N 0.000 claims description 2
• NWZLNNUTIRDXEM-AWEZNQCLSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-(pyridin-3-ylmethyl)pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=CN=C1 NWZLNNUTIRDXEM-AWEZNQCLSA-N 0.000 claims description 2
• QLTVKMVYQBUCQO-ZDUSSCGKSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[(1-methylpyrazol-4-yl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC=1C=NN(C)C=1 QLTVKMVYQBUCQO-ZDUSSCGKSA-N 0.000 claims description 2
• BYQRZRAOXXFPEO-JKSUJKDBSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[(1r)-1-phenylethyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C1([C@@H](C)NC(=O)C=2C(N[C@@H](C)C(C)C)=C3C=NN(C3=NC=2)CC)=CC=CC=C1 BYQRZRAOXXFPEO-JKSUJKDBSA-N 0.000 claims description 2
• WNDIXEKBRMKXKK-OXJNMPFZSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[(1r)-1-phenylpropyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C1([C@H](NC(=O)C=2C(=C3C=NN(CC)C3=NC=2)N[C@@H](C)C(C)C)CC)=CC=CC=C1 WNDIXEKBRMKXKK-OXJNMPFZSA-N 0.000 claims description 2
• NVLSJZMPXWOFJZ-LBPRGKRZSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[(2-methyl-1,3-thiazol-4-yl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CSC(C)=N1 NVLSJZMPXWOFJZ-LBPRGKRZSA-N 0.000 claims description 2
• UXJQEANSBQAEBL-HNNXBMFYSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[(3-methylsulfonylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=CC(S(C)(=O)=O)=C1 UXJQEANSBQAEBL-HNNXBMFYSA-N 0.000 claims description 2
• JGHDUJFUFWBGAJ-HNNXBMFYSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[(4-methylsulfonylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 JGHDUJFUFWBGAJ-HNNXBMFYSA-N 0.000 claims description 2
• XQTAGFZGUIFVTH-ZDUSSCGKSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[(6-oxo-1h-pyridin-3-yl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC=1C=CC(=O)NC=1 XQTAGFZGUIFVTH-ZDUSSCGKSA-N 0.000 claims description 2
• YLAJAQJPMZDRKP-VYRBHSGPSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[1-(4-methylsulfonylphenyl)ethyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NC(C)C1=CC=C(S(C)(=O)=O)C=C1 YLAJAQJPMZDRKP-VYRBHSGPSA-N 0.000 claims description 2
• WLOPDPBOSMLOBJ-HNNXBMFYSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[[3-(methylcarbamoyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=CC(C(=O)NC)=C1 WLOPDPBOSMLOBJ-HNNXBMFYSA-N 0.000 claims description 2
• BZUUBOVJKKHFEK-AWEZNQCLSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[[3-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=CC(C(F)(F)F)=C1 BZUUBOVJKKHFEK-AWEZNQCLSA-N 0.000 claims description 2
• BQFQKEDQWYMUJQ-HNNXBMFYSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[[4-(methylcarbamoyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=C(C(=O)NC)C=C1 BQFQKEDQWYMUJQ-HNNXBMFYSA-N 0.000 claims description 2
• LXUABLMXFLGZBW-AWEZNQCLSA-N 1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]-n-[[4-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=C(C(F)(F)F)C=C1 LXUABLMXFLGZBW-AWEZNQCLSA-N 0.000 claims description 2
• PWKDOPMWHXSMLV-CYBMUJFWSA-N 1-ethyl-n-(4-fluorophenyl)-4-[[(2r)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@H](C)C(C)C)C=1C(=O)NC1=CC=C(F)C=C1 PWKDOPMWHXSMLV-CYBMUJFWSA-N 0.000 claims description 2
• PWKDOPMWHXSMLV-ZDUSSCGKSA-N 1-ethyl-n-(4-fluorophenyl)-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NC1=CC=C(F)C=C1 PWKDOPMWHXSMLV-ZDUSSCGKSA-N 0.000 claims description 2
• JCPCZHYXKUMZDA-AWEZNQCLSA-N 1-ethyl-n-(4-methoxyphenyl)-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NC1=CC=C(OC)C=C1 JCPCZHYXKUMZDA-AWEZNQCLSA-N 0.000 claims description 2
• KMSYRELUEGODAS-AWEZNQCLSA-N 1-ethyl-n-[(3-fluorophenyl)methyl]-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=CC(F)=C1 KMSYRELUEGODAS-AWEZNQCLSA-N 0.000 claims description 2
• LUAVPCWXCLOGGB-AWEZNQCLSA-N 1-ethyl-n-[(4-fluorophenyl)methyl]-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=C(F)C=C1 LUAVPCWXCLOGGB-AWEZNQCLSA-N 0.000 claims description 2
• AKVFDZWSNMJGNB-AWEZNQCLSA-N 1-ethyl-n-[(4-hydroxyphenyl)methyl]-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=C(O)C=C1 AKVFDZWSNMJGNB-AWEZNQCLSA-N 0.000 claims description 2
• LXRGMAZSFXYPDX-HNNXBMFYSA-N 1-ethyl-n-[(4-methoxyphenyl)methyl]-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=C(OC)C=C1 LXRGMAZSFXYPDX-HNNXBMFYSA-N 0.000 claims description 2
• LKLFQAAFPABGBX-AWEZNQCLSA-N 1-ethyl-n-[(6-methoxypyridin-3-yl)methyl]-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=C(OC)N=C1 LKLFQAAFPABGBX-AWEZNQCLSA-N 0.000 claims description 2
• GTIHCAQEICFWCR-LBPRGKRZSA-N 1-ethyl-n-[2-(methanesulfonamido)ethyl]-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound CS(=O)(=O)NCCNC(=O)C1=CN=C2N(CC)N=CC2=C1N[C@@H](C)C(C)C GTIHCAQEICFWCR-LBPRGKRZSA-N 0.000 claims description 2
• IILAHCFTKKYFMR-HNNXBMFYSA-N 1-ethyl-n-[[3-(methanesulfonamido)phenyl]methyl]-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(N[C@@H](C)C(C)C)C=1C(=O)NCC1=CC=CC(NS(C)(=O)=O)=C1 IILAHCFTKKYFMR-HNNXBMFYSA-N 0.000 claims description 2
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