JP2007529486A5 - - Google Patents
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- JP2007529486A5 JP2007529486A5 JP2007503404A JP2007503404A JP2007529486A5 JP 2007529486 A5 JP2007529486 A5 JP 2007529486A5 JP 2007503404 A JP2007503404 A JP 2007503404A JP 2007503404 A JP2007503404 A JP 2007503404A JP 2007529486 A5 JP2007529486 A5 JP 2007529486A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- aminocarbonyl
- amino
- ethyl
- 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 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 32
- 150000003839 salts Chemical class 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 16
- -1 4- (aminocarbonyl) cyclohexyl Chemical group 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 230000002265 prevention Effects 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 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
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- ZCGIZZQSUIMIHI-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(2-methylsulfonylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 ZCGIZZQSUIMIHI-UHFFFAOYSA-N 0.000 claims 1
- RRKVLHFICMHKAU-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(2-phenylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 RRKVLHFICMHKAU-UHFFFAOYSA-N 0.000 claims 1
- VKGDMPYFFNTXIP-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(2-thiophen-3-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C2=CSC=C2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 VKGDMPYFFNTXIP-UHFFFAOYSA-N 0.000 claims 1
- RVBSJFDPBSNUKY-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(3-hydroxyphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC(O)=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 RVBSJFDPBSNUKY-UHFFFAOYSA-N 0.000 claims 1
- SSDUIGZUKOZTLV-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(3-phenylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 SSDUIGZUKOZTLV-UHFFFAOYSA-N 0.000 claims 1
- QOLXDQSYFFMQBJ-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(4-hydroxyphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(O)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 QOLXDQSYFFMQBJ-UHFFFAOYSA-N 0.000 claims 1
- OOQIKOXSZKAPBA-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(4-methoxyphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(OC)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 OOQIKOXSZKAPBA-UHFFFAOYSA-N 0.000 claims 1
- JKBKBTQUFUUQHB-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(4-methyl-2-phenylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(C)C=C(C=2C=CC=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 JKBKBTQUFUUQHB-UHFFFAOYSA-N 0.000 claims 1
- AXYLEUAQFJXWHA-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(4-methyl-2-thiophen-3-ylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(C)C=C(C2=CSC=C2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 AXYLEUAQFJXWHA-UHFFFAOYSA-N 0.000 claims 1
- HOAQYVZDYYVWST-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(4-methylsulfonylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 HOAQYVZDYYVWST-UHFFFAOYSA-N 0.000 claims 1
- KLUJSOAEXLKTQR-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[(4-phenylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 KLUJSOAEXLKTQR-UHFFFAOYSA-N 0.000 claims 1
- MLQIBLQASLHAIB-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[2-(3-methoxyphenyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C=C(OC)C=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 MLQIBLQASLHAIB-UHFFFAOYSA-N 0.000 claims 1
- CAZIEIOJEFAQAI-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[2-(4-methoxyphenyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C=CC(OC)=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 CAZIEIOJEFAQAI-UHFFFAOYSA-N 0.000 claims 1
- NSFGYOIAQQMSLJ-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[2-(4-methylphenyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C=CC(C)=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 NSFGYOIAQQMSLJ-UHFFFAOYSA-N 0.000 claims 1
- YLDKFPQBFNZWME-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[2-(4-methylthiophen-3-yl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C(=CSC=2)C)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 YLDKFPQBFNZWME-UHFFFAOYSA-N 0.000 claims 1
- NBOBGJJASYAUHK-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[2-(6-methoxypyridin-3-yl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C=NC(OC)=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 NBOBGJJASYAUHK-UHFFFAOYSA-N 0.000 claims 1
- PTNSMCSLHIURCU-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[2-(furan-3-yl)-4-methylphenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(C)C=C(C2=COC=C2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 PTNSMCSLHIURCU-UHFFFAOYSA-N 0.000 claims 1
- NOYJKXILZLBGKN-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[2-(furan-3-yl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C2=COC=C2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 NOYJKXILZLBGKN-UHFFFAOYSA-N 0.000 claims 1
- FTTFVVYHMDYKAX-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[2-[4-(trifluoromethyl)phenyl]phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 FTTFVVYHMDYKAX-UHFFFAOYSA-N 0.000 claims 1
- XCGYWMVMTYWDOP-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[4-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 XCGYWMVMTYWDOP-UHFFFAOYSA-N 0.000 claims 1
- MMKQFSFNDADCJZ-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-1-ethyl-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(C=2C=CC(=CC=2)C(F)(F)F)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 MMKQFSFNDADCJZ-UHFFFAOYSA-N 0.000 claims 1
- JXRZWSQUOSKXAM-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-(2,3-dihydro-1-benzofuran-5-ylmethyl)-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C2OCCC2=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 JXRZWSQUOSKXAM-UHFFFAOYSA-N 0.000 claims 1
- FWJFXKRPKMKQQY-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[(2,3-dichlorophenyl)methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC(Cl)=C(Cl)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 FWJFXKRPKMKQQY-UHFFFAOYSA-N 0.000 claims 1
- IXEZTMCWGOHJAB-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[(2,3-dimethylphenyl)methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC(C)=C(C)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 IXEZTMCWGOHJAB-UHFFFAOYSA-N 0.000 claims 1
- CZPPSFMUHHLSTN-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[(2,4-difluorophenyl)methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(F)C=C(F)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 CZPPSFMUHHLSTN-UHFFFAOYSA-N 0.000 claims 1
- IBXXHMZGPKMWFQ-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[(2,4-dimethylphenyl)methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(C)C=C(C)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 IBXXHMZGPKMWFQ-UHFFFAOYSA-N 0.000 claims 1
- RLXYAYUKDLFODG-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[(4-chloro-2-fluorophenyl)methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(Cl)C=C(F)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 RLXYAYUKDLFODG-UHFFFAOYSA-N 0.000 claims 1
- BZTAWBQJELZTHC-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[(4-chloro-2-methylphenyl)methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(Cl)C=C(C)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 BZTAWBQJELZTHC-UHFFFAOYSA-N 0.000 claims 1
- MRNLHCKEGOXGOC-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[(4-chlorophenyl)methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(Cl)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 MRNLHCKEGOXGOC-UHFFFAOYSA-N 0.000 claims 1
- NECDJYIINZIXOB-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[[2-(3-chlorophenyl)-4-methylphenyl]methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(C)C=C(C=2C=C(Cl)C=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 NECDJYIINZIXOB-UHFFFAOYSA-N 0.000 claims 1
- VEEXUMMZAMSUEQ-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[[2-(3-chlorophenyl)phenyl]methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C=C(Cl)C=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 VEEXUMMZAMSUEQ-UHFFFAOYSA-N 0.000 claims 1
- PQZYADBVAQXZTG-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[[2-(4-chlorophenyl)phenyl]methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C=CC(Cl)=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 PQZYADBVAQXZTG-UHFFFAOYSA-N 0.000 claims 1
- IZYMIEFEUVUJRZ-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[[4-(4-chlorophenyl)phenyl]methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 IZYMIEFEUVUJRZ-UHFFFAOYSA-N 0.000 claims 1
- GQDBELGEPMMTSN-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[[4-(4-ethoxyphenyl)phenyl]methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1C(C=C1)=CC=C1CNC(=O)C1=CN=C(N(CC)N=C2)C2=C1NC1CCN(C(N)=O)CC1 GQDBELGEPMMTSN-UHFFFAOYSA-N 0.000 claims 1
- GAXLSASSDIGOFT-UHFFFAOYSA-N 4-[(1-carbamoylpiperidin-4-yl)amino]-n-[[4-(difluoromethoxy)phenyl]methyl]-1-ethylpyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(OC(F)F)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCN(C(N)=O)CC1 GAXLSASSDIGOFT-UHFFFAOYSA-N 0.000 claims 1
- YHQHRYOZGGVVEL-UHFFFAOYSA-N 4-[(4-carbamoylcyclohexyl)amino]-1-ethyl-n-(5,6,7,8-tetrahydronaphthalen-1-ylmethyl)pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=2CCCCC=2C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(N)=O)CC1 YHQHRYOZGGVVEL-UHFFFAOYSA-N 0.000 claims 1
- CRVVGOYOEQATGS-UHFFFAOYSA-N 4-[(4-carbamoylcyclohexyl)amino]-1-ethyl-n-[(2-methylsulfonylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(N)=O)CC1 CRVVGOYOEQATGS-UHFFFAOYSA-N 0.000 claims 1
- ZOHQAQLVNBOMJA-UHFFFAOYSA-N 4-[(4-carbamoylcyclohexyl)amino]-1-ethyl-n-[(2-phenylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(N)=O)CC1 ZOHQAQLVNBOMJA-UHFFFAOYSA-N 0.000 claims 1
- NHHXXRBFFFDJIC-UHFFFAOYSA-N 4-[(4-carbamoylcyclohexyl)amino]-1-ethyl-n-[(3-phenylphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(N)=O)CC1 NHHXXRBFFFDJIC-UHFFFAOYSA-N 0.000 claims 1
- OJLXNTLOKAZZAQ-UHFFFAOYSA-N 4-[(4-carbamoylcyclohexyl)amino]-1-ethyl-n-[(4-fluorophenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(F)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(N)=O)CC1 OJLXNTLOKAZZAQ-UHFFFAOYSA-N 0.000 claims 1
- TUNOSBIMXXHDBG-UHFFFAOYSA-N 4-[(4-carbamoylcyclohexyl)amino]-1-ethyl-n-[(4-hydroxyphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(O)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(N)=O)CC1 TUNOSBIMXXHDBG-UHFFFAOYSA-N 0.000 claims 1
- JNOISAPWZIBULT-UHFFFAOYSA-N 4-[(4-carbamoylcyclohexyl)amino]-1-ethyl-n-[(4-methoxyphenyl)methyl]pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C=1C=C(OC)C=CC=1CNC(=O)C1=CN=C2N(CC)N=CC2=C1NC1CCC(C(N)=O)CC1 JNOISAPWZIBULT-UHFFFAOYSA-N 0.000 claims 1
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| 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 |
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| 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. |
| GB0806900D0 (en) * | 2008-04-16 | 2008-05-21 | Dow Corning | Fabric care emulsions |
| 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 |
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| BRPI1006729B1 (pt) * | 2009-04-13 | 2021-10-05 | Sulur Subramaniam Vanangamudi | Creme medicinal de ácido fusídico preparado utilizando fusidato de sódio e incorporando um biopolímero e seu processo de preparação |
| WO2010125082A1 (en) | 2009-04-30 | 2010-11-04 | Glaxo Group Limited | Oxazole substituted indazoles as pi3-kinase inhibitors |
| EP2507231A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Indazole derivatives as pi 3 - kinase inhibitors |
| US20120245171A1 (en) | 2009-12-03 | 2012-09-27 | Glaxo Group Limited | Benzpyrazole derivatives as inhibitors of pi3 kinases |
| EP2507226A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Novel compounds |
| 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 |
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| GB201018124D0 (en) | 2010-10-27 | 2010-12-08 | Glaxo Group Ltd | Polymorphs and salts |
| US9939529B2 (en) | 2012-08-27 | 2018-04-10 | Aktiebolaget Electrolux | Robot positioning system |
| CN110448222A (zh) | 2013-04-15 | 2019-11-15 | 伊莱克斯公司 | 机器人真空吸尘器 |
| US10219665B2 (en) | 2013-04-15 | 2019-03-05 | Aktiebolaget Electrolux | Robotic vacuum cleaner with protruding sidebrush |
| US9011934B2 (en) | 2013-06-14 | 2015-04-21 | SatisPharma, LLC | Multi-purpose anti-itch treatment |
| 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 |
| KR20160062178A (ko) | 2013-10-17 | 2016-06-01 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | 호흡기 질병의 치료를 위한 ｐｉ３ｋ 억제제 |
| EP3082544B1 (en) | 2013-12-19 | 2020-10-07 | Aktiebolaget Electrolux | Robotic vacuum cleaner with side brush moving in spiral pattern |
| JP2017502371A (ja) | 2013-12-19 | 2017-01-19 | アクチエボラゲット エレクトロルックス | 掃除領域の優先順位付け |
| US10433697B2 (en) | 2013-12-19 | 2019-10-08 | Aktiebolaget Electrolux | Adaptive speed control of rotating side brush |
| EP3082542B1 (en) | 2013-12-19 | 2018-11-28 | Aktiebolaget Electrolux | Sensing climb of obstacle of a robotic cleaning device |
| KR102130190B1 (ko) | 2013-12-19 | 2020-07-03 | 에이비 엘렉트로룩스 | 로봇 청소 장치 |
| CN105829985B (zh) | 2013-12-19 | 2020-04-07 | 伊莱克斯公司 | 具有周边记录功能的机器人清洁设备 |
| WO2015090399A1 (en) | 2013-12-19 | 2015-06-25 | Aktiebolaget Electrolux | Robotic cleaning device and method for landmark recognition |
| KR102116595B1 (ko) | 2013-12-20 | 2020-06-05 | 에이비 엘렉트로룩스 | 먼지통 |
| US20170100385A1 (en) | 2014-05-12 | 2017-04-13 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pharmaceutical compositions comprising danirixin for treating infectious diseases |
| US10518416B2 (en) | 2014-07-10 | 2019-12-31 | Aktiebolaget Electrolux | Method for detecting a measurement error in a robotic cleaning device |
| US10729297B2 (en) | 2014-09-08 | 2020-08-04 | Aktiebolaget Electrolux | Robotic vacuum cleaner |
| JP6443897B2 (ja) | 2014-09-08 | 2018-12-26 | アクチエボラゲット エレクトロルックス | ロボット真空掃除機 |
| US9452178B1 (en) | 2014-10-22 | 2016-09-27 | SatisPharma, LLC | Acne formulations, treatments, and pressure sensitive patches for delivery of acne formulations |
| WO2016091291A1 (en) | 2014-12-10 | 2016-06-16 | Aktiebolaget Electrolux | Using laser sensor for floor type detection |
| CN107072454A (zh) | 2014-12-12 | 2017-08-18 | 伊莱克斯公司 | 侧刷和机器人吸尘器 |
| CN107003669B (zh) | 2014-12-16 | 2023-01-31 | 伊莱克斯公司 | 用于机器人清洁设备的基于经验的路标 |
| JP6532530B2 (ja) | 2014-12-16 | 2019-06-19 | アクチエボラゲット エレクトロルックス | ロボット掃除機の掃除方法 |
| KR102343513B1 (ko) | 2015-04-17 | 2021-12-28 | 에이비 엘렉트로룩스 | 로봇 청소 장치 및 로봇 청소 장치의 제어 방법 |
| WO2017036532A1 (en) | 2015-09-03 | 2017-03-09 | Aktiebolaget Electrolux | System of robotic cleaning devices |
| BR112018007161B1 (pt) * | 2015-10-09 | 2024-01-16 | Galapagos Nv | COMPOSTOS PIRAZOLO[3,4-b]PIRIDIN-6-CARBOXAMIDA N-SULFONILADA, COMPOSIÇÃO FARMACÊUTICA CONTENDO OS DITOS COMPOSTOS E USOS DOS MESMOS PARA TRATAR FIBROSE CÍSTICA |
| GB201602527D0 (en) | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| US11169533B2 (en) | 2016-03-15 | 2021-11-09 | Aktiebolaget Electrolux | Robotic cleaning device and a method at the robotic cleaning device of performing cliff detection |
| US11122953B2 (en) | 2016-05-11 | 2021-09-21 | Aktiebolaget Electrolux | Robotic cleaning device |
| 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 |
| JP7243967B2 (ja) | 2017-06-02 | 2023-03-22 | アクチエボラゲット エレクトロルックス | ロボット清掃デバイスの前方の表面のレベル差を検出する方法 |
| GB201712081D0 (en) | 2017-07-27 | 2017-09-13 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| CN111093447B (zh) | 2017-09-26 | 2022-09-02 | 伊莱克斯公司 | 机器人清洁设备的移动控制 |
| KR102034538B1 (ko) * | 2017-11-28 | 2019-10-21 | 주식회사한국파마 | Jak 저해제 화합물, 및 이의 제조방법 |
| CN111875594A (zh) * | 2020-07-21 | 2020-11-03 | 中国药科大学 | 具有磷酸二酯酶4b抑制活性的吲唑杂环类化合物 |
Family Cites Families (30)
| 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 |
| US3833594A (en) * | 1971-08-05 | 1974-09-03 | Squibb & Sons Inc | Amino derivatives of pyrazolopyridine carboxylic acids and esters |
| US3925388A (en) * | 1971-08-05 | 1975-12-09 | Squibb & Sons Inc | 4-Piperazino-{8 3,4-b{9 pyridine-5-carboxylic acids and esters |
| US3856799A (en) * | 1971-08-05 | 1974-12-24 | Squibb & Sons Inc | Intermediates for production of amino derivatives of pyrazolopyridine carboxylic acids and esters |
| CA1003419A (en) | 1971-11-23 | 1977-01-11 | Theodor Denzel | Process for the production of pyrazolo (3,4-b) pyridines |
| US3840546A (en) * | 1972-11-15 | 1974-10-08 | Squibb & Sons Inc | Amino derivatives of pyrazolopyridine carboxamides |
| US3979399A (en) * | 1972-11-15 | 1976-09-07 | E. R. Squibb & Sons, Inc. | Amino derivatives of pyrazolopyridine carboxamides |
| US3833598A (en) * | 1972-12-29 | 1974-09-03 | Squibb & Sons Inc | Amino derivatives of pyrazolopyridine-6-carboxylic acids and esters |
| US4115394A (en) | 1974-05-06 | 1978-09-19 | E. R. Squibb & Sons, Inc. | Amino derivatives of 6-phenylpyrazolo[3,4-b]pyridines |
| US4364948A (en) | 1981-09-28 | 1982-12-21 | Ici Americas Inc. | Pyrazolo[3,4-b]pyridine compounds |
| GB8425104D0 (en) * | 1984-10-04 | 1984-11-07 | Ici America Inc | Amide derivatives |
| US5547954A (en) * | 1994-05-26 | 1996-08-20 | Fmc Corporation | 2,4-Diamino-5,6-disubstituted-and 5,6,7-trisubstituted-5-deazapteridines as insecticides |
| US5593997A (en) * | 1995-05-23 | 1997-01-14 | Pfizer Inc. | 4-aminopyrazolo(3-,4-D)pyrimidine and 4-aminopyrazolo-(3,4-D)pyridine tyrosine kinase inhibitors |
| US6326379B1 (en) * | 1998-09-16 | 2001-12-04 | Bristol-Myers Squibb Co. | Fused pyridine inhibitors of cGMP phosphodiesterase |
| RU2134498C1 (ru) * | 1998-12-08 | 1999-08-10 | Таран Александр Иванович | Контактный узел |
| IL148903A0 (en) | 1999-09-30 | 2002-09-12 | Neurogen Corp | Certain alkylene diamine-substituted heterocycles |
| GB9929685D0 (en) | 1999-12-15 | 2000-02-09 | Merck Sharp & Dohme | Therapeutic agents |
| JP2002020386A (ja) * | 2000-07-07 | 2002-01-23 | Ono Pharmaceut Co Ltd | ピラゾロピリジン誘導体 |
| US6670364B2 (en) * | 2001-01-31 | 2003-12-30 | Telik, Inc. | Antagonists of MCP-1 function and methods of use thereof |
| MXPA03007134A (es) | 2001-02-08 | 2004-10-15 | Memory Pharm Corp | Trifluorometilpurinas como inhibidores de fosfodiesterasa 4. |
| US6677365B2 (en) | 2001-04-03 | 2004-01-13 | Telik, Inc. | Antagonists of MCP-1 function and methods of use thereof |
| US20050043319A1 (en) * | 2001-08-14 | 2005-02-24 | Exonhit Therapeutics Sa | Molecular target of neurotoxicity |
| FR2828693B1 (fr) * | 2001-08-14 | 2004-06-18 | Exonhit Therapeutics Sa | Nouvelle cible moleculaire de la neurotoxicite |
| CN100387598C (zh) * | 2002-09-16 | 2008-05-14 | 葛兰素集团有限公司 | 吡唑并[3,4-b]吡啶化合物及其作为磷酸二酯酶抑制剂的用途 |
| GB0230045D0 (en) * | 2002-12-23 | 2003-01-29 | Glaxo Group Ltd | Compounds |
| US7117650B2 (en) * | 2002-12-09 | 2006-10-10 | Forrest Dockery | Hanger system |
| US20070111995A1 (en) * | 2003-12-19 | 2007-05-17 | Allen David G | Pyrazolo [3,4-B] pyridine Compounds and Their Use as Phosphodiesterase Inhibitors |
| GB0405933D0 (en) | 2004-03-16 | 2004-04-21 | Glaxo Group Ltd | Compounds |
| GB0405937D0 (en) | 2004-03-16 | 2004-04-21 | 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 |
-
2005
- 2005-03-15 US US10/598,973 patent/US20080275078A1/en not_active Abandoned
- 2005-03-15 AU AU2005223351A patent/AU2005223351A1/en not_active Abandoned
- 2005-03-15 EP EP05716291A patent/EP1735314A1/en not_active Withdrawn
- 2005-03-15 JP JP2007503306A patent/JP2007529464A/ja active Pending
- 2005-03-15 EP EP05718039A patent/EP1740590A1/en not_active Withdrawn
- 2005-03-15 JP JP2007503404A patent/JP2007529486A/ja active Pending
- 2005-03-15 WO PCT/GB2005/000987 patent/WO2005090354A1/en not_active Ceased
- 2005-03-15 CA CA002559629A patent/CA2559629A1/en not_active Abandoned
- 2005-03-15 BR BRPI0508843-7A patent/BRPI0508843A/pt not_active IP Right Cessation
- 2005-03-15 WO PCT/EP2005/003038 patent/WO2005090352A1/en not_active Ceased
- 2005-03-15 US US10/598,838 patent/US7709497B2/en not_active Expired - Fee Related
- 2005-03-15 RU RU2006132684/04A patent/RU2378274C2/ru not_active IP Right Cessation
- 2005-03-15 KR KR1020067021438A patent/KR20060130744A/ko not_active Ceased
- 2005-03-16 PE PE2005000299A patent/PE20060078A1/es not_active Application Discontinuation
- 2005-03-16 TW TW094108054A patent/TW200602051A/zh unknown
- 2005-03-16 AR ARP050101028A patent/AR048175A1/es not_active Application Discontinuation
-
2006
- 2006-09-11 IL IL178011A patent/IL178011A0/en unknown
- 2006-10-02 NO NO20064450A patent/NO20064450L/no not_active Application Discontinuation
- 2006-10-13 MA MA29385A patent/MA28531B1/fr unknown
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