JP2012508752A5 - - Google Patents
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- JP2012508752A5 JP2012508752A5 JP2011536447A JP2011536447A JP2012508752A5 JP 2012508752 A5 JP2012508752 A5 JP 2012508752A5 JP 2011536447 A JP2011536447 A JP 2011536447A JP 2011536447 A JP2011536447 A JP 2011536447A JP 2012508752 A5 JP2012508752 A5 JP 2012508752A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- hydroxy
- amino
- carbonyl
- oxo
- 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.)
- Granted
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 106
- 239000001257 hydrogen Substances 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 125000001072 heteroaryl group Chemical group 0.000 claims description 71
- 150000002431 hydrogen Chemical class 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 46
- 125000003107 substituted aryl group Chemical group 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
- 125000004442 acylamino group Chemical group 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 20
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 20
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 19
- 108010074633 Mixed Function Oxygenases Proteins 0.000 claims description 18
- 102000008109 Mixed Function Oxygenases Human genes 0.000 claims description 18
- -1 amino, substituted amino Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000005110 aryl thio group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 12
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 12
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 208000028867 ischemia Diseases 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 6
- 108010043005 Prolyl Hydroxylases Proteins 0.000 claims description 5
- 102000004079 Prolyl Hydroxylases Human genes 0.000 claims description 5
- 125000000613 asparagine group Chemical group N[C@@H](CC(N)=O)C(=O)* 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 102000003951 Erythropoietin Human genes 0.000 claims description 4
- 108090000394 Erythropoietin Proteins 0.000 claims description 4
- 206010021143 Hypoxia Diseases 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000003173 antianemic agent Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229940125367 erythropoiesis stimulating agent Drugs 0.000 claims description 4
- 229940105423 erythropoietin Drugs 0.000 claims description 4
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims description 4
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 101000881648 Homo sapiens Egl nine homolog 1 Proteins 0.000 claims description 3
- 101000881650 Homo sapiens Prolyl hydroxylase EGLN2 Proteins 0.000 claims description 3
- 101000881678 Homo sapiens Prolyl hydroxylase EGLN3 Proteins 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 102000053692 human EGLN1 Human genes 0.000 claims description 3
- 102000048660 human EGLN2 Human genes 0.000 claims description 3
- 102000050122 human EGLN3 Human genes 0.000 claims description 3
- 230000007954 hypoxia Effects 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
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- 206010054936 Cardiac cirrhosis Diseases 0.000 claims description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
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- 101000987586 Homo sapiens Eosinophil peroxidase Proteins 0.000 claims description 2
- 101000920686 Homo sapiens Erythropoietin Proteins 0.000 claims description 2
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| WO2009100250A1 (en) | 2008-02-05 | 2009-08-13 | Fibrogen, Inc. | Chromene derivatives and use thereof as hif hydroxylase activity inhibitors |
| CN102264740B (zh) | 2008-08-20 | 2014-10-15 | 菲布罗根有限公司 | 一种吡咯[1,2-b]哒嗪衍生物及其作为hif调节剂的用途 |
| CN105037323A (zh) | 2008-11-14 | 2015-11-11 | 菲布罗根有限公司 | 作为hif羟化酶抑制剂的苯并噻喃衍生物 |
| AU2011235212B2 (en) | 2010-03-31 | 2014-07-31 | The Scripps Research Institute | Reprogramming cells |
| EP2465841A1 (en) * | 2010-11-19 | 2012-06-20 | Lonza Ltd. | Preparation of esters of mono- or dicarboxylic non-aromatic and aromatic acids |
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2009
- 2009-11-11 CN CN201510259787.8A patent/CN105037323A/zh active Pending
- 2009-11-11 US US13/128,620 patent/US8927591B2/en active Active
- 2009-11-11 NZ NZ592741A patent/NZ592741A/xx not_active IP Right Cessation
- 2009-11-11 EP EP09756097.3A patent/EP2370422B1/en active Active
- 2009-11-11 AU AU2009314155A patent/AU2009314155B2/en not_active Ceased
- 2009-11-11 WO PCT/US2009/064065 patent/WO2010056767A1/en not_active Ceased
- 2009-11-11 JP JP2011536447A patent/JP5649584B2/ja not_active Expired - Fee Related
- 2009-11-11 CN CN200980154106.4A patent/CN102272117B/zh not_active Expired - Fee Related
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2014
- 2014-12-24 US US14/582,914 patent/US9149476B2/en active Active
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