JP2007529484A5 - - Google Patents
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- JP2007529484A5 JP2007529484A5 JP2007503401A JP2007503401A JP2007529484A5 JP 2007529484 A5 JP2007529484 A5 JP 2007529484A5 JP 2007503401 A JP2007503401 A JP 2007503401A JP 2007503401 A JP2007503401 A JP 2007503401A JP 2007529484 A5 JP2007529484 A5 JP 2007529484A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- alkyl
- methyl
- amino
- pyrazolo
- Prior art date
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 30
- 229910052757 nitrogen Inorganic materials 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 17
- -1 (cyclopropyl) methyl- Chemical group 0.000 claims 15
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 150000001721 carbon Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 229960003753 nitric oxide Drugs 0.000 claims 5
- 235000019391 nitrogen oxide Nutrition 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229940095102 methyl benzoate Drugs 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- KBVAUMWMFFABHY-HNNXBMFYSA-N 1-ethyl-n-[[4-(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=C(NS(C)(=O)=O)C=C1 KBVAUMWMFFABHY-HNNXBMFYSA-N 0.000 claims 1
- 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 1
- SHMOJDIIBQGKKI-UHFFFAOYSA-N 4-(tert-butylamino)-1-ethyl-n-(4-fluorophenyl)pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(NC(C)(C)C)C=1C(=O)NC1=CC=C(F)C=C1 SHMOJDIIBQGKKI-UHFFFAOYSA-N 0.000 claims 1
- LAGXPEILDXEIIU-UHFFFAOYSA-N 4-(tert-butylamino)-1-ethyl-n-[(4-methylsulfonylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(NC(C)(C)C)C=1C(=O)NCC1=CC=C(S(C)(=O)=O)C=C1 LAGXPEILDXEIIU-UHFFFAOYSA-N 0.000 claims 1
- SQJGAHQPZBVNAX-UHFFFAOYSA-N 4-(tert-butylamino)-1-ethyl-n-[[4-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(NC(C)(C)C)C=1C(=O)NCC1=CC=C(C(F)(F)F)C=C1 SQJGAHQPZBVNAX-UHFFFAOYSA-N 0.000 claims 1
- OMCVNINOOHWCKR-UHFFFAOYSA-N 4-(tert-butylamino)-n-(2,3-dihydro-1h-inden-2-yl)-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C1C2=CC=CC=C2CC1NC(=O)C1=CN=C2N(CC)N=CC2=C1NC(C)(C)C OMCVNINOOHWCKR-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010014824 Endotoxic shock Diseases 0.000 claims 1
- 206010018367 Glomerulonephritis chronic Diseases 0.000 claims 1
- 229930194542 Keto Natural products 0.000 claims 1
- 206010069698 Langerhans' cell histiocytosis Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 125000004848 alkoxyethyl group Chemical group 0.000 claims 1
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
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- 239000003937 drug carrier Substances 0.000 claims 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
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- LVWKQHFUWWHDQH-FQEVSTJZSA-N n-(2,2-diphenylethyl)-1-ethyl-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)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 LVWKQHFUWWHDQH-FQEVSTJZSA-N 0.000 claims 1
- UOPUGUZCAKUDPM-OAHLLOKOSA-N n-(2,3-dihydro-1h-inden-2-yl)-1-ethyl-4-[[(2r)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C1C2=CC=CC=C2CC1NC(=O)C1=CN=C2N(CC)N=CC2=C1N[C@H](C)C(C)C UOPUGUZCAKUDPM-OAHLLOKOSA-N 0.000 claims 1
- UOPUGUZCAKUDPM-HNNXBMFYSA-N n-(2,3-dihydro-1h-inden-2-yl)-1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C1C2=CC=CC=C2CC1NC(=O)C1=CN=C2N(CC)N=CC2=C1N[C@@H](C)C(C)C UOPUGUZCAKUDPM-HNNXBMFYSA-N 0.000 claims 1
- YHWVWUVSNQEUEM-PIVQAISJSA-N n-(5-chloro-2,3-dihydro-1h-inden-2-yl)-1-ethyl-4-[[(2s)-3-methylbutan-2-yl]amino]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C1C2=CC=C(Cl)C=C2CC1NC(=O)C1=CN=C2N(CC)N=CC2=C1N[C@@H](C)C(C)C YHWVWUVSNQEUEM-PIVQAISJSA-N 0.000 claims 1
- VASMXARUVIGLBT-ZDUSSCGKSA-N n-[(2,5-difluorophenyl)methyl]-1-ethyl-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(F)=CC=C1F VASMXARUVIGLBT-ZDUSSCGKSA-N 0.000 claims 1
- PWKUWGOOTKXUQQ-ZDUSSCGKSA-N n-[(2,6-difluorophenyl)methyl]-1-ethyl-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=C(F)C=CC=C1F PWKUWGOOTKXUQQ-ZDUSSCGKSA-N 0.000 claims 1
- BOKAOAKVAVVEJR-AWEZNQCLSA-N n-[(2-carbamoylphenyl)methyl]-1-ethyl-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=C1C(N)=O BOKAOAKVAVVEJR-AWEZNQCLSA-N 0.000 claims 1
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- ZKTMTGUVLDZDSU-ZDUSSCGKSA-N n-[(3,4-difluorophenyl)methyl]-1-ethyl-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(F)=C1 ZKTMTGUVLDZDSU-ZDUSSCGKSA-N 0.000 claims 1
- CALGFWLASZYOJF-AWEZNQCLSA-N n-[(3-carbamoylphenyl)methyl]-1-ethyl-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(C(N)=O)=C1 CALGFWLASZYOJF-AWEZNQCLSA-N 0.000 claims 1
- HOLYOOPKBFTPFR-ZDUSSCGKSA-N n-[(5-chloropyridin-2-yl)methyl]-1-ethyl-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(Cl)C=N1 HOLYOOPKBFTPFR-ZDUSSCGKSA-N 0.000 claims 1
- FABACGYPPNLERO-INIZCTEOSA-N n-[[2-(dimethylamino)phenyl]methyl]-1-ethyl-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=C1N(C)C FABACGYPPNLERO-INIZCTEOSA-N 0.000 claims 1
- KQIDGQISLJNNRN-AWEZNQCLSA-N n-[[4-(difluoromethoxy)phenyl]methyl]-1-ethyl-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(F)F)C=C1 KQIDGQISLJNNRN-AWEZNQCLSA-N 0.000 claims 1
- XEHJOPQXKQPBJS-INIZCTEOSA-N n-[[4-(dimethylsulfamoyl)phenyl]methyl]-1-ethyl-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(S(=O)(=O)N(C)C)C=C1 XEHJOPQXKQPBJS-INIZCTEOSA-N 0.000 claims 1
- BCROFPCTGJGLHQ-IBGZPJMESA-N n-benzhydryl-1-ethyl-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)NC(C=1C=CC=CC=1)C1=CC=CC=C1 BCROFPCTGJGLHQ-IBGZPJMESA-N 0.000 claims 1
- CPVNDAPYZWTDSV-OAHLLOKOSA-N n-benzyl-1-ethyl-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)NCC1=CC=CC=C1 CPVNDAPYZWTDSV-OAHLLOKOSA-N 0.000 claims 1
- CPVNDAPYZWTDSV-HNNXBMFYSA-N n-benzyl-1-ethyl-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=C1 CPVNDAPYZWTDSV-HNNXBMFYSA-N 0.000 claims 1
- VXSLWBZUCLRXBO-UHFFFAOYSA-N n-benzyl-4-(tert-butylamino)-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1N=C2N(CC)N=CC2=C(NC(C)(C)C)C=1C(=O)NCC1=CC=CC=C1 VXSLWBZUCLRXBO-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000003419 tautomerization reaction Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 208000018464 vernal keratoconjunctivitis Diseases 0.000 claims 1
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| GBGB0405937.4A GB0405937D0 (en) | 2004-03-16 | 2004-03-16 | Compounds |
| PCT/GB2005/000976 WO2005090353A1 (en) | 2004-03-16 | 2005-03-15 | PYRAZOLO[3,4-b]PYRIDINE COMPOUNDS, AND THEIR USE AS PDE4 INHIBITORS |
Publications (2)
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| JP2007529484A JP2007529484A (ja) | 2007-10-25 |
| JP2007529484A5 true JP2007529484A5 (https=) | 2008-05-01 |
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| JP (1) | JP2007529484A (https=) |
| GB (1) | GB0405937D0 (https=) |
| WO (1) | WO2005090353A1 (https=) |
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| GB0230045D0 (en) | 2002-12-23 | 2003-01-29 | Glaxo Group Ltd | Compounds |
| US20080275078A1 (en) | 2004-03-16 | 2008-11-06 | Glaxo Group Limited | Pyrazolo[3,4-B] Pyridine Compounds and Their Use as Pde4 Inhibitors |
| EP1899294B1 (en) * | 2005-06-13 | 2015-03-18 | Merck Sharp & Dohme Limited | Therapeutic agents |
| MX2008013411A (es) | 2006-04-20 | 2008-11-04 | Glaxo Group Ltd | Nuevos compuestos. |
| AR061571A1 (es) | 2006-06-23 | 2008-09-03 | Smithkline Beecham Corp | Compuesto sal del acido toluenosulfonico de 4-{[6-cloro-3-({[(2- cloro-3-fluorofenil) amino]carbonil} amino)- 2- hidroxifenil]sulfonil] -1- piperazinacarbxilato de 1.1-dimetiletilo, composicion farmaceutica que lo comprende su uso para la fabricacion de un medicamento combinacion farmaceutica con un |
| GB0614570D0 (en) * | 2006-07-21 | 2006-08-30 | Glaxo Group Ltd | Compounds |
| SI2046787T1 (sl) | 2006-08-01 | 2011-07-29 | Glaxo Group Ltd | Pirazolo(3,4-b)piridinske spojine in njihova uporaba kot PDE4 inhibitorji |
| PE20081889A1 (es) | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
| UY31637A1 (es) | 2008-02-06 | 2009-08-03 | Farmacoforos duales-antagonistas muscarinicos de pde4 | |
| PE20091553A1 (es) | 2008-02-06 | 2009-10-30 | Glaxo Group Ltd | Farmacoforos duales - antagonistas muscarinicos de pde4 |
| AR070563A1 (es) | 2008-02-06 | 2010-04-21 | Glaxo Group Ltd | Compuesto de un biciclo condensado pirazol-piridin-amina, composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para el tratamiento de enfermedades respiratorias. |
| WO2009147476A1 (en) * | 2008-06-02 | 2009-12-10 | Matrix Laboratories Ltd. | Novel pde inhibitors, pharmaceutical compositions containing them and processes for their preparation |
| ES2566339T3 (es) | 2008-06-05 | 2016-04-12 | Glaxo Group Limited | Derivados de 4-carboxamida indazol útiles como inhibidores de PI3-quinasas |
| AU2010219097A1 (en) | 2009-01-13 | 2011-08-04 | Glaxo Group Limited | Pyrimidinecarboxamide derivatives as inhibitors of SYK kinase |
| JP5656880B2 (ja) | 2009-03-09 | 2015-01-21 | グラクソ グループ リミテッドＧｌａｘｏ Ｇｒｏｕｐ Ｌｉｍｉｔｅｄ | Ｐｉ３キナーゼの阻害剤としての４−オキサジアゾール−２−イル−インダゾール |
| WO2010102968A1 (en) | 2009-03-10 | 2010-09-16 | Glaxo Group Limited | Indole derivatives as ikk2 inhibitors |
| WO2010106016A1 (en) | 2009-03-17 | 2010-09-23 | Glaxo Group Limited | Pyrimidine derivatives used as itk inhibitors |
| WO2010125082A1 (en) | 2009-04-30 | 2010-11-04 | Glaxo Group Limited | Oxazole substituted indazoles as pi3-kinase inhibitors |
| EP2507226A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Novel compounds |
| US20120245171A1 (en) | 2009-12-03 | 2012-09-27 | Glaxo Group Limited | Benzpyrazole derivatives as inhibitors of pi3 kinases |
| EP2507231A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Indazole derivatives as pi 3 - kinase inhibitors |
| WO2011110575A1 (en) | 2010-03-11 | 2011-09-15 | Glaxo Group Limited | Derivatives of 2-[2-(benzo- or pyrido-) thiazolylamino]-6-aminopyridine, useful in the treatment of respiratoric, allergic or inflammatory diseases |
| RS54286B1 (sr) | 2010-09-08 | 2016-02-29 | Glaxosmithkline Intellectual Property Development Limited | Polimorfi i soli n-[5-[4-(5-{[(2r,6s)-2,6-dimetil-4-morfolinil]metil}-1,3-oksazol-2-il)-1h-indazol-6-il]-2(metiloksi)-3-piridinil]-metansulfonamida |
| US9326987B2 (en) | 2010-09-08 | 2016-05-03 | Glaxo Group Limited | Indazole derivatives for use in the treatment of influenza virus infection |
| WO2012035055A1 (en) | 2010-09-17 | 2012-03-22 | Glaxo Group Limited | Novel compounds |
| GB201018124D0 (en) | 2010-10-27 | 2010-12-08 | Glaxo Group Ltd | Polymorphs and salts |
| KR20160062178A (ko) | 2013-10-17 | 2016-06-01 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | 호흡기 질병의 치료를 위한 ｐｉ３ｋ 억제제 |
| JP2016537327A (ja) | 2013-10-17 | 2016-12-01 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 呼吸器疾患の治療のためのｐｉ３ｋ阻害剤 |
| US20170100385A1 (en) | 2014-05-12 | 2017-04-13 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pharmaceutical compositions comprising danirixin for treating infectious diseases |
| US10272074B2 (en) * | 2015-01-29 | 2019-04-30 | Sanford Burnham Prebys Medical Discovery Institute | Inhibitors of glucocorticoid receptor translocation |
| GB201602527D0 (en) | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| WO2018029126A1 (en) | 2016-08-08 | 2018-02-15 | Glaxosmithkline Intellectual Property Development Limited | Chemical compounds |
| GB201706102D0 (en) | 2017-04-18 | 2017-05-31 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| GB201712081D0 (en) | 2017-07-27 | 2017-09-13 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| GB201813791D0 (en) * | 2018-08-23 | 2018-10-10 | Benevolental Bio Ltd | Organic compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE787249A (fr) * | 1971-08-05 | 1973-02-05 | Squibb & Sons Inc | Derives amino d'acides pyrazolopyridine carboxyliques, leurs esters et les sels de ces composes, ainsi que leurs procedes de preparation |
| US3925388A (en) * | 1971-08-05 | 1975-12-09 | Squibb & Sons Inc | 4-Piperazino-{8 3,4-b{9 pyridine-5-carboxylic acids and esters |
| US3840546A (en) * | 1972-11-15 | 1974-10-08 | Squibb & Sons Inc | Amino derivatives of pyrazolopyridine carboxamides |
| US4072681A (en) * | 1977-03-02 | 1978-02-07 | E. R. Squibb & Sons, Inc. | 3,7-Dihydro- and 1,7-dihydro-4H-pyrazolo[4',3':5,6]pyrido[4,3-d]pyrimidin-4-ones |
| US6326379B1 (en) * | 1998-09-16 | 2001-12-04 | Bristol-Myers Squibb Co. | Fused pyridine inhibitors of cGMP phosphodiesterase |
| JP2002020386A (ja) * | 2000-07-07 | 2002-01-23 | Ono Pharmaceut Co Ltd | ピラゾロピリジン誘導体 |
-
2004
- 2004-03-16 GB GBGB0405937.4A patent/GB0405937D0/en not_active Ceased
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2005
- 2005-03-15 US US10/598,944 patent/US7465743B2/en not_active Expired - Fee Related
- 2005-03-15 WO PCT/GB2005/000976 patent/WO2005090353A1/en not_active Ceased
- 2005-03-15 JP JP2007503401A patent/JP2007529484A/ja active Pending
- 2005-03-15 EP EP05718029A patent/EP1735315A1/en not_active Withdrawn
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