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 |
|---|---|---|---|
| GBGB0915892.4A GB0915892D0 (en) | 2009-09-10 | 2009-09-10 | Compounds |
| GB0915892.4 | 2009-09-10 | ||
| 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 (https=) | 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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| US (1) | US20120172333A1 (https=) |
| EP (1) | EP2475660A1 (https=) |
| JP (1) | JP2013504537A (https=) |
| GB (1) | GB0915892D0 (https=) |
| WO (1) | WO2011029855A1 (https=) |
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| 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 |
| EP2928474B1 (en) | 2012-12-07 | 2018-11-14 | ChemoCentryx, Inc. | Diazole lactams |
| PT2935227T (pt) * | 2012-12-21 | 2017-12-06 | Chemocentryx Inc | Amidas diazol como antagonistas do recetor ccr1 |
| EP2970177A1 (en) | 2013-03-15 | 2016-01-20 | Pfizer Inc. | Indole compounds that activate ampk |
| WO2015103480A1 (en) | 2014-01-02 | 2015-07-09 | Massachusetts Eye & Ear Infirmary | Treating ocular neovascularization |
| RU2017107543A (ru) | 2014-08-27 | 2018-10-02 | Шионоги Энд Ко., Лтд. | Производное азаиндола с аmpk-активирующим действием |
| SG11201808626WA (en) | 2016-04-07 | 2018-10-30 | Chemocentryx Inc | Reducing tumor burden by administering ccr1 antagonists in combination with pd-1 inhibitors or pd-l1 inhibitors |
| 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 |
| WO2021236617A1 (en) | 2020-05-19 | 2021-11-25 | Kallyope, Inc. | Ampk activators |
| CN116390925A (zh) | 2020-06-26 | 2023-07-04 | 卡尔优普公司 | Ampk活化剂 |
| US11857346B2 (en) | 2021-05-25 | 2024-01-02 | Warsaw Orthopedic, Inc. | Systems and methods for real-time monitoring of bone correction |
| JP2024540522A (ja) | 2021-11-19 | 2024-10-31 | ザ・ブロード・インスティテュート・インコーポレイテッド | キナーゼを標的結合部分で標識するための二官能性キメラ分子及びその使用方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1383771A1 (en) * | 2001-04-20 | 2004-01-28 | Vertex Pharmaceuticals Incorporated | 9-deazaguanine derivatives 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 |
| WO2005080367A1 (en) | 2004-02-12 | 2005-09-01 | Pharmagene Laboratories 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 |
| CA2714181C (en) * | 2008-02-04 | 2013-12-24 | 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 JP JP2012528352A patent/JP2013504537A/ja active Pending
- 2010-09-08 EP EP10749667A patent/EP2475660A1/en not_active Withdrawn
- 2010-09-08 US US13/394,927 patent/US20120172333A1/en not_active Abandoned
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