JP2013504537A5 - - Google Patents
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- JP2013504537A5 JP2013504537A5 JP2012528352A JP2012528352A JP2013504537A5 JP 2013504537 A5 JP2013504537 A5 JP 2013504537A5 JP 2012528352 A JP2012528352 A JP 2012528352A JP 2012528352 A JP2012528352 A JP 2012528352A JP 2013504537 A5 JP2013504537 A5 JP 2013504537A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- dihydro
- pyrrolo
- oxo
- pyridine
- 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 28
- 150000003839 salts Chemical class 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- -1 (2′-hydroxy-5′-methyl-4-biphenylyl) -5-oxo-4,5-dihydro-1H-pyrrolo [3,2-b] pyridine-6-carbonitrile Chemical compound 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 3
- MPLLLQUZNJSVTK-UHFFFAOYSA-N 5-[3-[4-[2-(4-fluorophenyl)ethoxy]phenyl]propyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1CCCC(C=C1)=CC=C1OCCC1=CC=C(F)C=C1 MPLLLQUZNJSVTK-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 241000701022 Cytomegalovirus Species 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000005176 Hepatitis C Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
- 230000007625 mitochondrial abnormality Effects 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000001076 sarcopenia Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- SOVGCQBJQGBLMC-UHFFFAOYSA-N 1-(4-acetylphenyl)-2-chloro-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=CC(C(=O)C)=CC=C1N1C(C(O)=C(C#N)C(=O)N2)=C2C=C1Cl SOVGCQBJQGBLMC-UHFFFAOYSA-N 0.000 claims 1
- OWVRYRWMCLLPHJ-UHFFFAOYSA-N 1-(4-bromophenyl)-2-chloro-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=C(Cl)N1C1=CC=C(Br)C=C1 OWVRYRWMCLLPHJ-UHFFFAOYSA-N 0.000 claims 1
- LWBQKVJXMARBOW-UHFFFAOYSA-N 1-(4-bromophenyl)-6-(4-fluorophenyl)-7-hydroxy-4h-pyrrolo[3,2-b]pyridin-5-one Chemical compound O=C1NC=2C=CN(C=3C=CC(Br)=CC=3)C=2C(O)=C1C1=CC=C(F)C=C1 LWBQKVJXMARBOW-UHFFFAOYSA-N 0.000 claims 1
- GGNBFPAPHVBNMS-UHFFFAOYSA-N 1-(4-bromophenyl)-7-hydroxy-4h-pyrrolo[3,2-b]pyridin-5-one Chemical compound C1=2C(O)=CC(=O)NC=2C=CN1C1=CC=C(Br)C=C1 GGNBFPAPHVBNMS-UHFFFAOYSA-N 0.000 claims 1
- OPWAKAHNFYSFPF-UHFFFAOYSA-N 1-(4-bromophenyl)-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C1=CC=C(Br)C=C1 OPWAKAHNFYSFPF-UHFFFAOYSA-N 0.000 claims 1
- YDXGVHCPIALQPW-UHFFFAOYSA-N 1-(4-bromophenyl)-7-hydroxy-6-(4-methoxyphenyl)-4h-pyrrolo[3,2-b]pyridin-5-one Chemical compound C1=CC(OC)=CC=C1C(C(N1)=O)=C(O)C2=C1C=CN2C1=CC=C(Br)C=C1 YDXGVHCPIALQPW-UHFFFAOYSA-N 0.000 claims 1
- HJORWOASHDGSGO-UHFFFAOYSA-N 1-(4-ethylphenyl)-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-2,6-dicarbonitrile Chemical compound C1=CC(CC)=CC=C1N1C(C(O)=C(C#N)C(=O)N2)=C2C=C1C#N HJORWOASHDGSGO-UHFFFAOYSA-N 0.000 claims 1
- QBFXIXVTEDFKNZ-UHFFFAOYSA-N 1-(4-ethylphenyl)-7-hydroxy-5-oxo-6-phenyl-4h-pyrrolo[3,2-b]pyridine-2-carbonitrile Chemical compound C1=CC(CC)=CC=C1N1C(C(O)=C(C=2C=CC=CC=2)C(=O)N2)=C2C=C1C#N QBFXIXVTEDFKNZ-UHFFFAOYSA-N 0.000 claims 1
- UABLQGXAHDVACC-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=C2OCOC2=CC(C2=CC=C(C=C2)N2C=CC=3NC(=O)C(C#N)=C(C2=3)O)=C1 UABLQGXAHDVACC-UHFFFAOYSA-N 0.000 claims 1
- VMPXNCOXNJFLCJ-UHFFFAOYSA-N 1-[4-(1-benzothiophen-3-yl)phenyl]-2-chloro-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=CC=C2C(C3=CC=C(C=C3)N3C(Cl)=CC=4NC(=O)C(C#N)=C(C3=4)O)=CSC2=C1 VMPXNCOXNJFLCJ-UHFFFAOYSA-N 0.000 claims 1
- HDXPALQWOKGQDK-UHFFFAOYSA-N 1-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound O1CCOC2=CC(C3=CC=C(C=C3)N3C=CC=4NC(=O)C(C#N)=C(C3=4)O)=CC=C21 HDXPALQWOKGQDK-UHFFFAOYSA-N 0.000 claims 1
- JZACVLHBVDTOKS-UHFFFAOYSA-N 1-[4-(2,4-dichlorophenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=C(Cl)C=C1Cl JZACVLHBVDTOKS-UHFFFAOYSA-N 0.000 claims 1
- AKJWCZCDAPJZQR-UHFFFAOYSA-N 1-[4-(2,4-difluorophenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=C(F)C=C1F AKJWCZCDAPJZQR-UHFFFAOYSA-N 0.000 claims 1
- ISZKOVZBYZGFOI-UHFFFAOYSA-N 1-[4-(2,4-dimethylphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound CC1=CC(C)=CC=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 ISZKOVZBYZGFOI-UHFFFAOYSA-N 0.000 claims 1
- RHZMFNXCUKPEKI-UHFFFAOYSA-N 1-[4-(2-chloro-6-hydroxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound OC1=CC=CC(Cl)=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 RHZMFNXCUKPEKI-UHFFFAOYSA-N 0.000 claims 1
- TVAXMIPMAIUFMP-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=CC=C1Cl TVAXMIPMAIUFMP-UHFFFAOYSA-N 0.000 claims 1
- RWHJMHFIXDMCJC-UHFFFAOYSA-N 1-[4-(2-cyanophenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=CC=C1C#N RWHJMHFIXDMCJC-UHFFFAOYSA-N 0.000 claims 1
- CGTQAVXGBSUIAB-UHFFFAOYSA-N 1-[4-(2-fluoro-4-methylphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound FC1=CC(C)=CC=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 CGTQAVXGBSUIAB-UHFFFAOYSA-N 0.000 claims 1
- WKIBRVWRPSWINM-UHFFFAOYSA-N 1-[4-(2-fluoro-6-hydroxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound OC1=CC=CC(F)=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 WKIBRVWRPSWINM-UHFFFAOYSA-N 0.000 claims 1
- WLSSAIXNWJHHPH-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=CC=C1F WLSSAIXNWJHHPH-UHFFFAOYSA-N 0.000 claims 1
- LWPSMLAPKBLKSQ-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound CC1=NOC(C)=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 LWPSMLAPKBLKSQ-UHFFFAOYSA-N 0.000 claims 1
- HJSIZSCNOQERDC-UHFFFAOYSA-N 1-[4-(3-chloro-2-hydroxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound OC1=C(Cl)C=CC=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 HJSIZSCNOQERDC-UHFFFAOYSA-N 0.000 claims 1
- WNEYRUZRBQLDFP-UHFFFAOYSA-N 1-[4-(3-fluoro-2-hydroxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound OC1=C(F)C=CC=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 WNEYRUZRBQLDFP-UHFFFAOYSA-N 0.000 claims 1
- VJEFMYKXXQWXAP-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=CC(F)=C1 VJEFMYKXXQWXAP-UHFFFAOYSA-N 0.000 claims 1
- ASRCCDVHJPWBLY-UHFFFAOYSA-N 1-[4-(4-chloro-2-hydroxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound OC1=CC(Cl)=CC=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 ASRCCDVHJPWBLY-UHFFFAOYSA-N 0.000 claims 1
- GUOXWXJRPBODNP-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 GUOXWXJRPBODNP-UHFFFAOYSA-N 0.000 claims 1
- XGAFRTYMPFNLFF-UHFFFAOYSA-N 1-[4-(4-cyanophenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 XGAFRTYMPFNLFF-UHFFFAOYSA-N 0.000 claims 1
- SFDHEXOFDQWSNB-UHFFFAOYSA-N 1-[4-(4-fluoro-2-hydroxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound OC1=CC(F)=CC=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 SFDHEXOFDQWSNB-UHFFFAOYSA-N 0.000 claims 1
- GPXHMPKRTGSMPG-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)phenyl]-7-hydroxy-4-methyl-5-oxopyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)N(C)C=2C=CN1C(C=C1)=CC=C1C1=CC=C(F)C=C1 GPXHMPKRTGSMPG-UHFFFAOYSA-N 0.000 claims 1
- PHXMQINEDUJDET-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=C(F)C=C1 PHXMQINEDUJDET-UHFFFAOYSA-N 0.000 claims 1
- VBFGSZQLIGZSBT-UHFFFAOYSA-N 1-[4-(5-chlorothiophen-2-yl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=C(Cl)S1 VBFGSZQLIGZSBT-UHFFFAOYSA-N 0.000 claims 1
- YLVLCMUWAPBADG-UHFFFAOYSA-N 1-[4-(5-cyanopyridin-2-yl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=C(C#N)C=N1 YLVLCMUWAPBADG-UHFFFAOYSA-N 0.000 claims 1
- YZGYRFBJDGFVMP-UHFFFAOYSA-N 1-[4-(5-fluoro-2-hydroxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound OC1=CC=C(F)C=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 YZGYRFBJDGFVMP-UHFFFAOYSA-N 0.000 claims 1
- VYPMXYNVMBVOLF-UHFFFAOYSA-N 1-[4-(6-aminopyridin-2-yl)phenyl]-2-chloro-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound NC1=CC=CC(C=2C=CC(=CC=2)N2C=3C(O)=C(C#N)C(=O)NC=3C=C2Cl)=N1 VYPMXYNVMBVOLF-UHFFFAOYSA-N 0.000 claims 1
- DHKNCTZGBFIRHF-UHFFFAOYSA-N 1-[4-(6-fluoropyridin-3-yl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=C(F)N=C1 DHKNCTZGBFIRHF-UHFFFAOYSA-N 0.000 claims 1
- VEKMLRNQTGFKCF-UHFFFAOYSA-N 1-[4-(furan-2-yl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound C1=2C(O)=C(C#N)C(=O)NC=2C=CN1C(C=C1)=CC=C1C1=CC=CO1 VEKMLRNQTGFKCF-UHFFFAOYSA-N 0.000 claims 1
- DZSMUEDGQSOZNA-UHFFFAOYSA-N 2-[2-chloro-7-hydroxy-5-oxo-1-(4-thiophen-3-ylphenyl)-4h-pyrrolo[3,2-b]pyridin-6-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(C(N1)=O)=C(O)C2=C1C=C(Cl)N2C1=CC=C(C2=CSC=C2)C=C1 DZSMUEDGQSOZNA-UHFFFAOYSA-N 0.000 claims 1
- RTGHFMWBDXTRRA-UHFFFAOYSA-N 2-[4-(2-chloro-7-hydroxy-5-oxo-6-phenyl-4h-pyrrolo[3,2-b]pyridin-1-yl)phenyl]acetonitrile Chemical compound O=C1NC=2C=C(Cl)N(C=3C=CC(CC#N)=CC=3)C=2C(O)=C1C1=CC=CC=C1 RTGHFMWBDXTRRA-UHFFFAOYSA-N 0.000 claims 1
- QPSOTUXMLQLJFI-UHFFFAOYSA-N 2-chloro-1-(3,4-dimethylphenyl)-7-hydroxy-6-phenyl-4h-pyrrolo[3,2-b]pyridin-5-one Chemical compound C1=C(C)C(C)=CC=C1N1C(C(O)=C(C=2C=CC=CC=2)C(=O)N2)=C2C=C1Cl QPSOTUXMLQLJFI-UHFFFAOYSA-N 0.000 claims 1
- VZMAWGXHBDFQSF-UHFFFAOYSA-N 2-chloro-1-(4-cyclohexylphenyl)-7-hydroxy-6-phenyl-4h-pyrrolo[3,2-b]pyridin-5-one Chemical compound O=C1NC=2C=C(Cl)N(C=3C=CC(=CC=3)C3CCCCC3)C=2C(O)=C1C1=CC=CC=C1 VZMAWGXHBDFQSF-UHFFFAOYSA-N 0.000 claims 1
- CNKANSZIAKIZPN-UHFFFAOYSA-N 2-chloro-1-(4-ethylphenyl)-7-hydroxy-6-phenyl-4h-pyrrolo[3,2-b]pyridin-5-one Chemical compound C1=CC(CC)=CC=C1N1C(C(O)=C(C(=O)N2)C=3C=CC=CC=3)=C2C=C1Cl CNKANSZIAKIZPN-UHFFFAOYSA-N 0.000 claims 1
- AFUWBTJCUKISGI-UHFFFAOYSA-N 2-chloro-1-(4-fluorophenyl)-7-hydroxy-6-phenyl-4h-pyrrolo[3,2-b]pyridin-5-one Chemical compound O=C1NC=2C=C(Cl)N(C=3C=CC(F)=CC=3)C=2C(O)=C1C1=CC=CC=C1 AFUWBTJCUKISGI-UHFFFAOYSA-N 0.000 claims 1
- QPCSPECTFDRENH-UHFFFAOYSA-N 2-chloro-1-[4-(2-chloro-4-methoxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound ClC1=CC(OC)=CC=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2Cl)C=C1 QPCSPECTFDRENH-UHFFFAOYSA-N 0.000 claims 1
- JZNSHXSGNXFKAB-UHFFFAOYSA-N 2-chloro-1-[4-(2-chloro-6-hydroxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound OC1=CC=CC(Cl)=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2Cl)C=C1 JZNSHXSGNXFKAB-UHFFFAOYSA-N 0.000 claims 1
- NRFOQWINTRJQFY-UHFFFAOYSA-N 2-chloro-1-[4-(2-chloro-6-methoxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound COC1=CC=CC(Cl)=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2Cl)C=C1 NRFOQWINTRJQFY-UHFFFAOYSA-N 0.000 claims 1
- QSMMGMCYDLTDCW-UHFFFAOYSA-N 2-chloro-1-[4-(2-fluoro-4-methylphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound FC1=CC(C)=CC=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2Cl)C=C1 QSMMGMCYDLTDCW-UHFFFAOYSA-N 0.000 claims 1
- PWQZWQTZKGTMFD-UHFFFAOYSA-N 2-chloro-1-[4-(2-fluoro-6-hydroxyphenyl)phenyl]-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridine-6-carbonitrile Chemical compound OC1=CC=CC(F)=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2Cl)C=C1 PWQZWQTZKGTMFD-UHFFFAOYSA-N 0.000 claims 1
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- 125000005843 halogen group Chemical group 0.000 claims 1
- XXMYPGAAWKDPON-UHFFFAOYSA-N n-[4-(2-chloro-6-cyano-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridin-1-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1N1C(C(O)=C(C#N)C(=O)N2)=C2C=C1Cl XXMYPGAAWKDPON-UHFFFAOYSA-N 0.000 claims 1
- PXSJVTBMAPJUNC-UHFFFAOYSA-N n-[4-[4-(6-cyano-7-hydroxy-5-oxo-4h-pyrrolo[3,2-b]pyridin-1-yl)phenyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=C(N2C=3C(O)=C(C#N)C(=O)NC=3C=C2)C=C1 PXSJVTBMAPJUNC-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0915892.4 | 2009-09-10 | ||
| GBGB0915892.4A GB0915892D0 (en) | 2009-09-10 | 2009-09-10 | Compounds |
| PCT/EP2010/063196 WO2011029855A1 (en) | 2009-09-10 | 2010-09-08 | Pyrrolo-pyridine derivatives as activators of ampk |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013504537A JP2013504537A (ja) | 2013-02-07 |
| JP2013504537A5 true JP2013504537A5 (enExample) | 2013-10-24 |
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| JP2012528352A Pending JP2013504537A (ja) | 2009-09-10 | 2010-09-08 | Ａｍｐｋ活性化因子としてのピロロピリジン誘導体 |
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| EP (1) | EP2475660A1 (enExample) |
| JP (1) | JP2013504537A (enExample) |
| GB (1) | GB0915892D0 (enExample) |
| WO (1) | WO2011029855A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2486631A (en) * | 2010-12-01 | 2012-06-27 | Univ Sheffield | Phenol/quinone boronic acids/esters and method of preparation thereof |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| WO2014089495A1 (en) | 2012-12-07 | 2014-06-12 | Chemocentryx, Inc. | Diazole lactams |
| EP2935227B1 (en) | 2012-12-21 | 2017-09-13 | ChemoCentryx, Inc. | Diazole amides as ccr1 receptor antagonists |
| US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| WO2015103480A1 (en) | 2014-01-02 | 2015-07-09 | Massachusetts Eye & Ear Infirmary | Treating ocular neovascularization |
| US9980948B2 (en) | 2014-08-27 | 2018-05-29 | Shionogi & Co., Ltd. | Azaindole derivative having AMPK-activating activity |
| PL3439653T3 (pl) | 2016-04-07 | 2021-07-05 | Chemocentryx, Inc. | Zmniejszenie obciążenia guzem przez podawanie antagonistów ccr1 w skojarzeniu z inhibitorami pd-1 lub inhibitorami pd-l1 |
| EP4066832A4 (en) * | 2019-11-14 | 2024-01-03 | Zincure Corp. | Pharmaceutical composition for treating multiple sclerosis on basis of ampk inhibitory function and zinc homeostasis control function |
| CA3178994A1 (en) | 2020-05-19 | 2021-11-25 | Iyassu Sebhat | Ampk activators |
| JP2023531726A (ja) | 2020-06-26 | 2023-07-25 | キャリーオペ，インク． | Ａｍｐｋアクチベーター |
| US11857346B2 (en) | 2021-05-25 | 2024-01-02 | Warsaw Orthopedic, Inc. | Systems and methods for real-time monitoring of bone correction |
| EP4433458A4 (en) | 2021-11-19 | 2025-10-29 | Broad Inst Inc | Bifunctional chimeric molecules for labeling kinases with target bond fractions and their methods of use |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030096813A1 (en) * | 2001-04-20 | 2003-05-22 | Jingrong Cao | Compositions useful as inhibitors of GSK-3 |
| GB0124848D0 (en) * | 2001-10-16 | 2001-12-05 | Celltech R&D Ltd | Chemical compounds |
| US7119205B2 (en) * | 2003-05-16 | 2006-10-10 | Abbott Laboratories | Thienopyridones as AMPK activators for the treatment of diabetes and obesity |
| EP1723132A1 (en) | 2004-02-12 | 2006-11-22 | Asterand Uk Limited | Ep2 receptor agonists |
| FR2888848B1 (fr) * | 2005-07-22 | 2007-09-28 | Sanofi Aventis Sa | Derives de n-(arylalkyl)-1h-pyrrrolopyridine-2-carboxamides, leur preparation et leur application en therapeutique |
| US8030346B2 (en) * | 2007-05-04 | 2011-10-04 | Amgen Inc. | Heterocyclic quinolone derivatives that inhibit prolyl hydroxylase activity |
| EP2231666B1 (en) * | 2007-12-12 | 2015-07-29 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| MY158994A (en) * | 2008-02-04 | 2016-11-30 | Mercury Therapeutics Inc | Ampk modulators |
-
2009
- 2009-09-10 GB GBGB0915892.4A patent/GB0915892D0/en not_active Ceased
-
2010
- 2010-09-08 WO PCT/EP2010/063196 patent/WO2011029855A1/en not_active Ceased
- 2010-09-08 US US13/394,927 patent/US20120172333A1/en not_active Abandoned
- 2010-09-08 EP EP10749667A patent/EP2475660A1/en not_active Withdrawn
- 2010-09-08 JP JP2012528352A patent/JP2013504537A/ja active Pending
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