MX2014012330A - Compuestos de indol e indazol que activan la proteina quinasa activada por 5' adenosina monofosfato. - Google Patents
Compuestos de indol e indazol que activan la proteina quinasa activada por 5' adenosina monofosfato.Info
- Publication number
- MX2014012330A MX2014012330A MX2014012330A MX2014012330A MX2014012330A MX 2014012330 A MX2014012330 A MX 2014012330A MX 2014012330 A MX2014012330 A MX 2014012330A MX 2014012330 A MX2014012330 A MX 2014012330A MX 2014012330 A MX2014012330 A MX 2014012330A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- alkoxy
- hydroxy
- independently
- heterocycle
- Prior art date
Links
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract description 7
- 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 328
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 661
- 229910052731 fluorine Inorganic materials 0.000 claims description 569
- 229910052739 hydrogen Inorganic materials 0.000 claims description 368
- 229910052736 halogen Inorganic materials 0.000 claims description 361
- 150000002367 halogens Chemical class 0.000 claims description 360
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 315
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 314
- 125000000623 heterocyclic group Chemical group 0.000 claims description 313
- 150000003839 salts Chemical class 0.000 claims description 298
- 125000001424 substituent group Chemical group 0.000 claims description 296
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 258
- 125000001188 haloalkyl group Chemical group 0.000 claims description 228
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 228
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 203
- 229910052801 chlorine Inorganic materials 0.000 claims description 196
- 125000003118 aryl group Chemical group 0.000 claims description 191
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 187
- -1 5-oxo-4,5-dihydro-1, 2,4- oxadiazol-3-yl Chemical group 0.000 claims description 166
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 138
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 123
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 112
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 100
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 93
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 91
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 81
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 81
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 59
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 58
- 125000002757 morpholinyl group Chemical group 0.000 claims description 57
- 229910052757 nitrogen Inorganic materials 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 56
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 55
- 125000003386 piperidinyl group Chemical group 0.000 claims description 55
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 55
- 125000001425 triazolyl group Chemical group 0.000 claims description 54
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 53
- 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 52
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 52
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 51
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 50
- 125000004076 pyridyl group Chemical group 0.000 claims description 50
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 49
- 229910052702 rhenium Inorganic materials 0.000 claims description 49
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 40
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 38
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 38
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 241000124008 Mammalia Species 0.000 claims description 32
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 30
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 17
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 13
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl 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
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 claims description 10
- 208000008589 Obesity Diseases 0.000 claims description 9
- 235000020824 obesity Nutrition 0.000 claims description 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 9
- 208000009304 Acute Kidney Injury Diseases 0.000 claims description 8
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 7
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl 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
- 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
- 201000011040 acute kidney failure Diseases 0.000 claims description 6
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 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 5
- 208000020832 chronic kidney disease Diseases 0.000 claims description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 4
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- ZHTQCPCDXKMMLU-UHFFFAOYSA-N norathyriol Chemical compound OC1=C(O)C=C2C(=O)C3=C(O)C=C(O)C=C3OC2=C1 ZHTQCPCDXKMMLU-UHFFFAOYSA-N 0.000 claims description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 17
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 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
- 230000002265 prevention Effects 0.000 claims 2
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 1
- 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
- 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 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
- 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 group 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
- RQZSOXIQLVNMAF-UHFFFAOYSA-N 6-chloro-5-[4-(3-hydroxycyclobutyl)phenyl]-1h-indole-3-carboxylic acid Chemical compound C1C(O)CC1C1=CC=C(C=2C(=CC=3NC=C(C=3C=2)C(O)=O)Cl)C=C1 RQZSOXIQLVNMAF-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
- 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
- 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
- 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
- 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 1
- ZHJIECWAFLWJSV-GFCCVEGCSA-N O[C@H]1CN(CC1)C1=CC=C(C(=N1)OC)N1C=C(C2=CC=CC=C12)C(=O)O Chemical compound O[C@H]1CN(CC1)C1=CC=C(C(=N1)OC)N1C=C(C2=CC=CC=C12)C(=O)O ZHJIECWAFLWJSV-GFCCVEGCSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
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- 230000004913 activation Effects 0.000 abstract description 11
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- UPJKSWLLCONYMW-UHFFFAOYSA-N 5'-Adenosine monophosphate Natural products COc1cc(O)c(C(=O)C)c(OC2OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C2O)c1 UPJKSWLLCONYMW-UHFFFAOYSA-N 0.000 abstract description 7
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 abstract description 7
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- 239000000460 chlorine Chemical group 0.000 description 188
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 85
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 34
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 34
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261622129P | 2012-04-10 | 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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| MX2014012330A true MX2014012330A (es) | 2015-01-12 |
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| Application Number | Title | Priority Date | Filing Date |
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| MX2014012330A MX2014012330A (es) | 2012-04-10 | 2013-04-01 | Compuestos de indol e indazol que activan la proteina quinasa activada por 5' adenosina monofosfato. |
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