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
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- 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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| CA2795611C (en) * | 2009-04-13 | 2016-09-20 | Sulur Subramaniam Vanangamudi | A medicinal fusidic acid cream made using sodium fusidate and incorporating a biopolymer and a process to make it |
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| 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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| US9011934B2 (en) | 2013-06-14 | 2015-04-21 | SatisPharma, LLC | Multi-purpose anti-itch treatment |
| AU2014336251A1 (en) | 2013-10-17 | 2016-04-14 | Glaxosmithkline Intellectual Property Development Limited | PI3K inhibitor for treatment of respiratory disease |
| RU2016112268A (ru) | 2013-10-17 | 2017-11-22 | Глаксосмитклайн Интеллекчуал Проперти Дивелопмент Лимитед | Ингибитор PI3K для лечения респираторного заболевания |
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-
2005
- 2005-03-15 EP EP05716291A patent/EP1735314A1/en not_active Withdrawn
- 2005-03-15 BR BRPI0508843-7A patent/BRPI0508843A/pt not_active IP Right Cessation
- 2005-03-15 WO PCT/GB2005/000987 patent/WO2005090354A1/en not_active Ceased
- 2005-03-15 US US10/598,838 patent/US7709497B2/en not_active Expired - Fee Related
- 2005-03-15 AU AU2005223351A patent/AU2005223351A1/en not_active Abandoned
- 2005-03-15 EP EP05718039A patent/EP1740590A1/en not_active Withdrawn
- 2005-03-15 WO PCT/EP2005/003038 patent/WO2005090352A1/en not_active Ceased
- 2005-03-15 RU RU2006132684/04A patent/RU2378274C2/ru not_active IP Right Cessation
- 2005-03-15 JP JP2007503306A patent/JP2007529464A/ja active Pending
- 2005-03-15 JP JP2007503404A patent/JP2007529486A/ja active Pending
- 2005-03-15 KR KR1020067021438A patent/KR20060130744A/ko not_active Ceased
- 2005-03-15 US US10/598,973 patent/US20080275078A1/en not_active Abandoned
- 2005-03-15 CA CA002559629A patent/CA2559629A1/en not_active Abandoned
- 2005-03-16 AR ARP050101028A patent/AR048175A1/es not_active Application Discontinuation
- 2005-03-16 TW TW094108054A patent/TW200602051A/zh unknown
- 2005-03-16 PE PE2005000299A patent/PE20060078A1/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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