TW201004956A - Pyrazolo[3,4-b]pyridine compounds, and their use as phosphodiesterase inhibitors - Google Patents
Pyrazolo[3,4-b]pyridine compounds, and their use as phosphodiesterase inhibitors Download PDFInfo
- Publication number
- TW201004956A TW201004956A TW098134389A TW98134389A TW201004956A TW 201004956 A TW201004956 A TW 201004956A TW 098134389 A TW098134389 A TW 098134389A TW 98134389 A TW98134389 A TW 98134389A TW 201004956 A TW201004956 A TW 201004956A
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- Prior art keywords
- ethyl
- group
- alkyl
- amine
- pyrazolo
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- 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title description 2
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 235
- 150000003839 salts Chemical class 0.000 claims abstract description 146
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 82
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 71
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 68
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 65
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 59
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- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 7
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 268
- -1 tetrahydro-2H-pyran-4-yl Chemical group 0.000 claims description 135
- 239000000203 mixture Substances 0.000 claims description 122
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 87
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 86
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 78
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 47
- 239000011737 fluorine Substances 0.000 claims description 45
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 41
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 36
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 35
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
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Classifications
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- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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