KR20150002782A - Ampk를 활성화시키는 인돌 및 인다졸 화합물 - Google Patents
Ampk를 활성화시키는 인돌 및 인다졸 화합물 Download PDFInfo
- Publication number
- KR20150002782A KR20150002782A KR20147031394A KR20147031394A KR20150002782A KR 20150002782 A KR20150002782 A KR 20150002782A KR 20147031394 A KR20147031394 A KR 20147031394A KR 20147031394 A KR20147031394 A KR 20147031394A KR 20150002782 A KR20150002782 A KR 20150002782A
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- KR
- South Korea
- Prior art keywords
- alkyl
- alkoxy
- hydroxy
- independently
- carbonyl
- 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.)
- Ceased
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract description 6
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title abstract description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title abstract description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title abstract description 3
- 101100321932 Rattus norvegicus Prkaa2 gene Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 522
- 238000000034 method Methods 0.000 claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 603
- 229910052731 fluorine Inorganic materials 0.000 claims description 595
- 229910052739 hydrogen Inorganic materials 0.000 claims description 400
- 229910052736 halogen Inorganic materials 0.000 claims description 366
- 150000002367 halogens Chemical class 0.000 claims description 366
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 342
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 327
- 150000003839 salts Chemical class 0.000 claims description 309
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 298
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 263
- 125000000623 heterocyclic group Chemical group 0.000 claims description 256
- -1 hydroxy, mercapto Chemical class 0.000 claims description 225
- 125000001424 substituent group Chemical group 0.000 claims description 214
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 213
- 229910052801 chlorine Inorganic materials 0.000 claims description 206
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 201
- 125000003118 aryl group Chemical group 0.000 claims description 190
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 174
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 146
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 140
- 125000000217 alkyl group Chemical group 0.000 claims description 138
- 125000001072 heteroaryl group Chemical group 0.000 claims description 116
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 106
- 125000003545 alkoxy group Chemical group 0.000 claims description 100
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 95
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 125000002757 morpholinyl group Chemical group 0.000 claims description 57
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 57
- 125000002393 azetidinyl group Chemical group 0.000 claims description 56
- 125000003566 oxetanyl group Chemical group 0.000 claims description 56
- 125000004193 piperazinyl group Chemical group 0.000 claims description 56
- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical class C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 claims description 56
- 229940075559 piperine Drugs 0.000 claims description 56
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 claims description 56
- 235000019100 piperine Nutrition 0.000 claims description 56
- 125000000719 pyrrolidinyl group Chemical class 0.000 claims description 56
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 54
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 53
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 53
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 53
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 51
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 51
- 125000001425 triazolyl group Chemical group 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 50
- 241000124008 Mammalia Species 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 23
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 14
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 10
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 8
- 201000011040 acute kidney failure Diseases 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 8
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 7
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 7
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 6
- MCTFEMGZCDYRSE-UHFFFAOYSA-N 5-(4-bromophenyl)-1h-indole-3-carboxamide Chemical compound C1=C2C(C(=O)N)=CNC2=CC=C1C1=CC=C(Br)C=C1 MCTFEMGZCDYRSE-UHFFFAOYSA-N 0.000 claims description 6
- IDPDUOKTSMTTTI-UHFFFAOYSA-N 5-[4-(2,6-dihydroxyphenyl)phenyl]-1h-indole-3-carboxamide Chemical compound C1=C2C(C(=O)N)=CNC2=CC=C1C(C=C1)=CC=C1C1=C(O)C=CC=C1O IDPDUOKTSMTTTI-UHFFFAOYSA-N 0.000 claims description 6
- 208000009304 Acute Kidney Injury Diseases 0.000 claims description 6
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 6
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 6
- 208000033626 Renal failure acute Diseases 0.000 claims description 6
- 208000012998 acute renal failure Diseases 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 208000020832 chronic kidney disease Diseases 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- JQJNGAWEMYQJIQ-UHFFFAOYSA-N 4,6-difluoro-5-[4-(oxan-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound FC1=C2C(C(=O)O)=CNC2=CC(F)=C1C(C=C1)=CC=C1C1CCCCO1 JQJNGAWEMYQJIQ-UHFFFAOYSA-N 0.000 claims 2
- QROCFHQHLVJSBH-UHFFFAOYSA-N 4,6-difluoro-5-[4-[1-(hydroxymethyl)cyclobutyl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=C3C(C(O)=O)=CNC3=CC=2F)F)C=CC=1C1(CO)CCC1 QROCFHQHLVJSBH-UHFFFAOYSA-N 0.000 claims 2
- FSHXDAZLNDYYBL-UHFFFAOYSA-N 6-fluoro-5-[4-(oxan-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(F)=C1C(C=C1)=CC=C1C1CCCCO1 FSHXDAZLNDYYBL-UHFFFAOYSA-N 0.000 claims 2
- YVBSJPQSGAJIPG-UHFFFAOYSA-N 4,6-difluoro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(C(C)(CO)C)=CC=C1C1=C(F)C=C(NC=C2C(O)=O)C2=C1F YVBSJPQSGAJIPG-UHFFFAOYSA-N 0.000 claims 1
- VPUNMIRZXILGLE-UHFFFAOYSA-N 4,6-difluoro-5-[4-(1-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound FC1=C2C(C(=O)O)=CNC2=CC(F)=C1C(C=C1)=CC=C1C1(O)CCC1 VPUNMIRZXILGLE-UHFFFAOYSA-N 0.000 claims 1
- CZRBSHRHFKGINR-UHFFFAOYSA-N 4,6-difluoro-5-[4-[1-(hydroxymethyl)cyclopropyl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=C3C(C(O)=O)=CNC3=CC=2F)F)C=CC=1C1(CO)CC1 CZRBSHRHFKGINR-UHFFFAOYSA-N 0.000 claims 1
- CXERMAZBUDCCIL-UHFFFAOYSA-N 6-chloro-5-(2-methoxy-6-morpholin-4-ylpyridin-3-yl)-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C(OC)=NC=1N1CCOCC1 CXERMAZBUDCCIL-UHFFFAOYSA-N 0.000 claims 1
- QFVPMQJTUWDFKR-UHFFFAOYSA-N 6-chloro-5-(4-methoxyphenyl)-1h-indole-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O QFVPMQJTUWDFKR-UHFFFAOYSA-N 0.000 claims 1
- HFTSUSPGKRQUGS-UHFFFAOYSA-N 6-chloro-5-[2-fluoro-4-(1-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C(=C1)F)=CC=C1C1(O)CCC1 HFTSUSPGKRQUGS-UHFFFAOYSA-N 0.000 claims 1
- AUNQFTYGCPLFAH-LLVKDONJSA-N 6-chloro-5-[2-methoxy-6-[(3r)-3-methoxypyrrolidin-1-yl]pyridin-3-yl]-1h-indole-3-carboxylic acid Chemical compound C1[C@H](OC)CCN1C1=CC=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C(OC)=N1 AUNQFTYGCPLFAH-LLVKDONJSA-N 0.000 claims 1
- AUNQFTYGCPLFAH-NSHDSACASA-N 6-chloro-5-[2-methoxy-6-[(3s)-3-methoxypyrrolidin-1-yl]pyridin-3-yl]-1h-indole-3-carboxylic acid Chemical compound C1[C@@H](OC)CCN1C1=CC=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C(OC)=N1 AUNQFTYGCPLFAH-NSHDSACASA-N 0.000 claims 1
- AVSRVMKWMOGUGW-UHFFFAOYSA-N 6-chloro-5-[3-fluoro-4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C(F)C(C(C)(CO)C)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O AVSRVMKWMOGUGW-UHFFFAOYSA-N 0.000 claims 1
- VJRMUMYLSWYBNV-UHFFFAOYSA-N 6-chloro-5-[3-fluoro-4-(1-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1F)=CC=C1C1(O)CCC1 VJRMUMYLSWYBNV-UHFFFAOYSA-N 0.000 claims 1
- YFGODCGRXUUSOT-UHFFFAOYSA-N 6-chloro-5-[4-(1-hydroxy-2-methylpropan-2-yl)-3-methoxyphenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C(C(C)(C)CO)C(OC)=CC(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)=C1 YFGODCGRXUUSOT-UHFFFAOYSA-N 0.000 claims 1
- BUXGLMHGEKZJGD-UHFFFAOYSA-N 6-chloro-5-[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(C(C)(CO)C)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O BUXGLMHGEKZJGD-UHFFFAOYSA-N 0.000 claims 1
- KMRDDGOECBQZPA-UHFFFAOYSA-N 6-chloro-5-[4-(1-hydroxycyclobutyl)-3-methoxyphenyl]-1h-indole-3-carboxylic acid Chemical compound COC1=CC(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)=CC=C1C1(O)CCC1 KMRDDGOECBQZPA-UHFFFAOYSA-N 0.000 claims 1
- FHQXLWCFSUSXBF-UHFFFAOYSA-N 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1C1(O)CCC1 FHQXLWCFSUSXBF-UHFFFAOYSA-N 0.000 claims 1
- KCELVRDPYZTFPG-UHFFFAOYSA-N 6-chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-n-methylsulfonyl-1h-indole-3-carboxamide Chemical compound C1=C2C(C(=O)NS(=O)(=O)C)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1C1(O)CCC1 KCELVRDPYZTFPG-UHFFFAOYSA-N 0.000 claims 1
- YGKWXCWHOYVSAU-UHFFFAOYSA-N 6-chloro-5-[4-(2-hydroxyethoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(OCCO)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O YGKWXCWHOYVSAU-UHFFFAOYSA-N 0.000 claims 1
- ZCTWOZZJNVDFFT-UHFFFAOYSA-N 6-chloro-5-[4-(2-hydroxyethyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(CCO)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O ZCTWOZZJNVDFFT-UHFFFAOYSA-N 0.000 claims 1
- QZIZUCHLAKADOE-UHFFFAOYSA-N 6-chloro-5-[4-(2-hydroxyphenyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1C1=CC=CC=C1O QZIZUCHLAKADOE-UHFFFAOYSA-N 0.000 claims 1
- MGVAKCXUPMDXHO-UHFFFAOYSA-N 6-chloro-5-[4-(2-methoxyethoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(OCCOC)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O MGVAKCXUPMDXHO-UHFFFAOYSA-N 0.000 claims 1
- LHXQQARKHXKMEH-UHFFFAOYSA-N 6-chloro-5-[4-(2-pyrazol-1-ylethoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCCN1C=CC=N1 LHXQQARKHXKMEH-UHFFFAOYSA-N 0.000 claims 1
- CNLIFFPPUZLKBG-UHFFFAOYSA-N 6-chloro-5-[4-(3-hydroxypropoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=CC(OCCCO)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O CNLIFFPPUZLKBG-UHFFFAOYSA-N 0.000 claims 1
- RHWVKZPITKBHLD-UHFFFAOYSA-N 6-chloro-5-[4-(3-morpholin-4-ylpropoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCCCN1CCOCC1 RHWVKZPITKBHLD-UHFFFAOYSA-N 0.000 claims 1
- NGSWNDMVAWOGHF-UHFFFAOYSA-N 6-chloro-5-[4-(3-piperazin-1-ylpropoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCCCN1CCNCC1 NGSWNDMVAWOGHF-UHFFFAOYSA-N 0.000 claims 1
- JJENQAOXTYKDLN-UHFFFAOYSA-N 6-chloro-5-[4-(oxan-4-yl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1C1CCOCC1 JJENQAOXTYKDLN-UHFFFAOYSA-N 0.000 claims 1
- DKFPQQPTLZDFBM-UHFFFAOYSA-N 6-chloro-5-[4-(oxetan-2-ylmethoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCC1CCO1 DKFPQQPTLZDFBM-UHFFFAOYSA-N 0.000 claims 1
- YGTQKVPGTICMSG-UHFFFAOYSA-N 6-chloro-5-[4-(oxetan-3-ylmethoxy)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCC1COC1 YGTQKVPGTICMSG-UHFFFAOYSA-N 0.000 claims 1
- GKPYSXKYDOSNMQ-LJQANCHMSA-N 6-chloro-5-[4-[(2r)-oxan-2-yl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1[C@H]1CCCCO1 GKPYSXKYDOSNMQ-LJQANCHMSA-N 0.000 claims 1
- MJIQWOBJTBDAGR-UHFFFAOYSA-N 6-chloro-5-[4-[1-(hydroxymethyl)cyclobutyl]-3-methoxyphenyl]-1h-indole-3-carboxylic acid Chemical compound COC1=CC(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)=CC=C1C1(CO)CCC1 MJIQWOBJTBDAGR-UHFFFAOYSA-N 0.000 claims 1
- OSNPJCNKGDNYRY-UHFFFAOYSA-N 6-chloro-5-[4-[1-(hydroxymethyl)cyclobutyl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C=CC=1C1(CO)CCC1 OSNPJCNKGDNYRY-UHFFFAOYSA-N 0.000 claims 1
- HPSVQYWQVLFPRF-UHFFFAOYSA-N 6-chloro-5-[4-[1-(hydroxymethyl)cyclopropyl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C=CC=1C1(CO)CC1 HPSVQYWQVLFPRF-UHFFFAOYSA-N 0.000 claims 1
- OAOIRGKGPZPGRA-UHFFFAOYSA-N 6-chloro-5-[4-[2-(1,2,4-triazol-1-yl)ethoxy]phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(Cl)=C1C(C=C1)=CC=C1OCCN1C=NC=N1 OAOIRGKGPZPGRA-UHFFFAOYSA-N 0.000 claims 1
- BAOSCKJYYGSTGB-UHFFFAOYSA-N 6-chloro-5-[4-[3-(hydroxymethyl)oxetan-3-yl]phenyl]-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C=CC=1C1(CO)COC1 BAOSCKJYYGSTGB-UHFFFAOYSA-N 0.000 claims 1
- MJHBRTGGZYSCHJ-UHFFFAOYSA-N 6-chloro-5-[6-(dimethylamino)-2-methoxypyridin-3-yl]-1h-indole-3-carboxylic acid Chemical compound COC1=NC(N(C)C)=CC=C1C(C(=C1)Cl)=CC2=C1NC=C2C(O)=O MJHBRTGGZYSCHJ-UHFFFAOYSA-N 0.000 claims 1
- CVPDYZUEDILILE-JTQLQIEISA-N 6-chloro-5-[6-[(3s)-3-hydroxypyrrolidin-1-yl]-2-methoxypyridin-3-yl]-1h-indole-3-carboxylic acid Chemical compound C=1C=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C(OC)=NC=1N1CC[C@H](O)C1 CVPDYZUEDILILE-JTQLQIEISA-N 0.000 claims 1
- JCVIFVYRMKVCDU-UHFFFAOYSA-N 6-fluoro-5-[4-(1-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(F)=C1C(C=C1)=CC=C1C1(O)CCC1 JCVIFVYRMKVCDU-UHFFFAOYSA-N 0.000 claims 1
- OCYUCPMTHRRWDS-UHFFFAOYSA-N 6-fluoro-5-[4-(2-hydroxyphenyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=CNC2=CC(F)=C1C(C=C1)=CC=C1C1=CC=CC=C1O OCYUCPMTHRRWDS-UHFFFAOYSA-N 0.000 claims 1
- RQZSOXIQLVNMAF-JOCQHMNTSA-N C1[C@@H](O)C[C@@H]1C1=CC=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C=C1 Chemical compound C1[C@@H](O)C[C@@H]1C1=CC=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C=C1 RQZSOXIQLVNMAF-JOCQHMNTSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 108010011376 AMP-Activated Protein Kinases Proteins 0.000 abstract description 30
- 102000014156 AMP-Activated Protein Kinases Human genes 0.000 abstract description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
- 230000004913 activation Effects 0.000 abstract description 11
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261622129P | 2012-04-10 | 2012-04-10 | |
| US61/622,129 | 2012-04-10 | ||
| PCT/IB2013/052604 WO2013153479A2 (en) | 2012-04-10 | 2013-04-01 | Indole and indazole compounds that activate ampk |
Publications (1)
| Publication Number | Publication Date |
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| KR20150002782A true KR20150002782A (ko) | 2015-01-07 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR20147031394A Ceased KR20150002782A (ko) | 2012-04-10 | 2013-04-01 | Ampk를 활성화시키는 인돌 및 인다졸 화합물 |
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