AU2012250690B2 - Pyruvate kinase activators for use in therapy - Google Patents

Info

Publication number

AU2012250690B2

AU2012250690B2 AU2012250690A AU2012250690A AU2012250690B2 AU 2012250690 B2 AU2012250690 B2 AU 2012250690B2 AU 2012250690 A AU2012250690 A AU 2012250690A AU 2012250690 A AU2012250690 A AU 2012250690A AU 2012250690 B2 AU2012250690 B2 AU 2012250690B2

Authority

AU

Australia

Prior art keywords

alkyl

independently selected

compound

phenyl

halo

Prior art date

2011-05-03

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.)

Ceased

Links

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• 102000013009 Pyruvate Kinase Human genes 0.000 title abstract description 12
• 108020005115 Pyruvate Kinase Proteins 0.000 title abstract description 12
• 239000012190 activator Substances 0.000 title description 10
• 238000002560 therapeutic procedure Methods 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 430
• 238000000034 method Methods 0.000 claims abstract description 71
• 239000000203 mixture Substances 0.000 claims description 113
• 125000000217 alkyl group Chemical group 0.000 claims description 100
• -1 carbocycle Chemical group 0.000 claims description 64
• 125000004432 carbon atom Chemical group C* 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 52
• 125000005843 halogen group Chemical group 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 41
• 125000001188 haloalkyl group Chemical group 0.000 claims description 41
• 125000000623 heterocyclic group Chemical group 0.000 claims description 40
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims description 26
• 210000003743 erythrocyte Anatomy 0.000 claims description 21
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 239000003937 drug carrier Substances 0.000 claims description 18
• 210000004369 blood Anatomy 0.000 claims description 17
• 239000008280 blood Substances 0.000 claims description 17
• 210000004027 cell Anatomy 0.000 claims description 16
• 125000002252 acyl group Chemical group 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 229910003827 NRaRb Inorganic materials 0.000 claims description 10
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 208000007475 hemolytic anemia Diseases 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
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• 108700014121 Pyruvate Kinase Deficiency of Red Cells Proteins 0.000 claims description 6
• 230000003213 activating effect Effects 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 201000003922 congenital nonspherocytic hemolytic anemia Diseases 0.000 claims description 5
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• 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 14
• ZTYZEUXZHGOXRT-UHFFFAOYSA-N quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)N)=CC=CC2=C1 ZTYZEUXZHGOXRT-UHFFFAOYSA-N 0.000 description 14
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• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 9
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