TW200815438A - Substituted pyrazolopyridines and salts thereof, pharmaceutical compositions comprising same, methods of preparing same and uses of same - Google Patents

Info

Publication number

TW200815438A

TW200815438A TW096121006A TW96121006A TW200815438A TW 200815438 A TW200815438 A TW 200815438A TW 096121006 A TW096121006 A TW 096121006A TW 96121006 A TW96121006 A TW 96121006A TW 200815438 A TW200815438 A TW 200815438A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

phenyl

methyl

cycloalkyl

Prior art date

2006-06-13

Links

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• 238000000034 method Methods 0.000 title claims abstract description 72
• 150000003839 salts Chemical class 0.000 title claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 title abstract description 12
• 150000005229 pyrazolopyridines Chemical class 0.000 title abstract description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 188
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 61
• 201000010099 disease Diseases 0.000 claims abstract description 60
• 238000004519 manufacturing process Methods 0.000 claims abstract description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 290
• 239000004202 carbamide Substances 0.000 claims description 182
• 229910052739 hydrogen Inorganic materials 0.000 claims description 169
• 239000001257 hydrogen Substances 0.000 claims description 167
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 140
• -1 Ci_C6 dentate Chemical group 0.000 claims description 123
• 238000002360 preparation method Methods 0.000 claims description 120
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 116
• 150000002431 hydrogen Chemical class 0.000 claims description 104
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 95
• 238000006243 chemical reaction Methods 0.000 claims description 90
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 85
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
• 150000001412 amines Chemical class 0.000 claims description 61
• 229910052736 halogen Inorganic materials 0.000 claims description 58
• 150000002367 halogens Chemical class 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 49
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 47
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
• 125000003545 alkoxy group Chemical group 0.000 claims description 41
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
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• 239000002253 acid Substances 0.000 claims description 36
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
• 239000000203 mixture Substances 0.000 claims description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 34
• 239000000126 substance Substances 0.000 claims description 34
• 229910052760 oxygen Inorganic materials 0.000 claims description 33
• 239000001301 oxygen Substances 0.000 claims description 33
• 125000001072 heteroaryl group Chemical group 0.000 claims description 32
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 31
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 28
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
• 230000033115 angiogenesis Effects 0.000 claims description 24
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• 125000003277 amino group Chemical group 0.000 claims description 18
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• 125000001188 haloalkyl group Chemical group 0.000 claims description 17
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• 230000009467 reduction Effects 0.000 claims description 13
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 12
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• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
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• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 239000002689 soil Substances 0.000 claims description 7
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• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
• FBADRUOBFLBKJQ-PEBGCTIMSA-N CMP-2-aminoethylphosphonate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)CCN)O[C@H]1N1C(=O)N=C(N)C=C1 FBADRUOBFLBKJQ-PEBGCTIMSA-N 0.000 claims description 6
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• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 238000005804 alkylation reaction Methods 0.000 claims description 6
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• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
• XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 5
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• 150000001204 N-oxides Chemical class 0.000 claims description 5
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
• 230000029936 alkylation Effects 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
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• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 150000003254 radicals Chemical class 0.000 claims description 5
• 229910052702 rhenium Inorganic materials 0.000 claims description 5
• 125000003944 tolyl group Chemical group 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
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• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
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• BICMJXXRUNJIDJ-UHFFFAOYSA-N (3-ethylphenyl)urea Chemical compound CCC1=CC=CC(NC(N)=O)=C1 BICMJXXRUNJIDJ-UHFFFAOYSA-N 0.000 claims description 2
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