HRP20191327T1 - 4-hidroksi-3-(heteroaril)piridin-2-on apj agonisti za primjenju u liječenju kardiovaskularnih poremećaja - Google Patents
4-hidroksi-3-(heteroaril)piridin-2-on apj agonisti za primjenju u liječenju kardiovaskularnih poremećaja Download PDFInfo
- Publication number
- HRP20191327T1 HRP20191327T1 HRP20191327T HRP20191327T1 HR P20191327 T1 HRP20191327 T1 HR P20191327T1 HR P20191327 T HRP20191327 T HR P20191327T HR P20191327 T1 HRP20191327 T1 HR P20191327T1
- Authority
- HR
- Croatia
- Prior art keywords
- oxadiazol
- dimethoxyphenyl
- butyl
- methyl
- diol
- Prior art date
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- 208000024172 Cardiovascular disease Diseases 0.000 title claims 3
- 239000000556 agonist Substances 0.000 title 1
- 229910052731 fluorine Inorganic materials 0.000 claims 41
- 229910052801 chlorine Inorganic materials 0.000 claims 40
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000000623 heterocyclic group Chemical group 0.000 claims 25
- 229910052794 bromium Inorganic materials 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 125000004452 carbocyclyl group Chemical group 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 150000001721 carbon Chemical group 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- -1 -(CH2)nORf Chemical group 0.000 claims 6
- ZEZJPIDPVXJEME-UHFFFAOYSA-N 2,4-Dihydroxypyridine Chemical compound OC=1C=CNC(=O)C=1 ZEZJPIDPVXJEME-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 235000019256 formaldehyde Nutrition 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- RWUPSJGCOFGHEA-UHFFFAOYSA-N 2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]-N-[2-(4-chlorophenyl)ethyl]acetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CC(=O)NCCC1=CC=C(C=C1)Cl)O)C1=C(C=CC=C1OC)OC RWUPSJGCOFGHEA-UHFFFAOYSA-N 0.000 claims 2
- ANQNPYQZSWHNHJ-UHFFFAOYSA-N 3-[5-(1,2-benzoxazol-3-ylmethyl)-1,3,4-oxadiazol-2-yl]-6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound O1N=C(C2=C1C=CC=C2)CC1=NN=C(O1)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O ANQNPYQZSWHNHJ-UHFFFAOYSA-N 0.000 claims 2
- OFJBKLPMIXYYMG-UHFFFAOYSA-N 3-[5-[(5-chloropyridin-2-yl)methyl]-1,3,4-oxadiazol-2-yl]-6-(ethoxymethyl)-4-hydroxy-5-(2-hydroxy-6-methoxyphenyl)-1H-pyridin-2-one Chemical compound ClC=1C=CC(=NC=1)CC1=NN=C(O1)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)O)COCC)O OFJBKLPMIXYYMG-UHFFFAOYSA-N 0.000 claims 2
- FCISDLZEPJSBHK-UHFFFAOYSA-N 6-butyl-3-[5-[(3,4-difluorophenyl)methyl]-1,3,4-oxadiazol-2-yl]-4-hydroxy-5-(3-propan-2-ylphenyl)-1H-pyridin-2-one Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C=1OC(=NN=1)CC1=CC(=C(C=C1)F)F)O)C1=CC(=CC=C1)C(C)C FCISDLZEPJSBHK-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010049694 Left Ventricular Dysfunction Diseases 0.000 claims 2
- 230000002107 myocardial effect Effects 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 2
- 238000007634 remodeling Methods 0.000 claims 2
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims 1
- QOUZYIAALGESEF-UHFFFAOYSA-N 2-[5-[5-(2,6-dimethoxyphenyl)-6-(ethoxymethyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]-N-(1,3-thiazol-2-yl)acetamide Chemical compound COC1=C(C(=CC=C1)OC)C=1C(=C(C(=NC=1COCC)O)C1=NN=C(O1)CC(=O)NC=1SC=CN=1)O QOUZYIAALGESEF-UHFFFAOYSA-N 0.000 claims 1
- SNAIEAPCIXQUDG-UHFFFAOYSA-N 2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]-N,N-diethylacetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CC(=O)N(CC)CC)O)C1=C(C=CC=C1OC)OC SNAIEAPCIXQUDG-UHFFFAOYSA-N 0.000 claims 1
- YFWCIOJUPBTQOP-UHFFFAOYSA-N 2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]-N,N-dimethylacetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CC(=O)N(C)C)O)C1=C(C=CC=C1OC)OC YFWCIOJUPBTQOP-UHFFFAOYSA-N 0.000 claims 1
- PZJXBXAIFHJWEL-UHFFFAOYSA-N 2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]-N-(1,3-oxazol-2-ylmethyl)acetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CC(=O)NCC=1OC=CN=1)O)C1=C(C=CC=C1OC)OC PZJXBXAIFHJWEL-UHFFFAOYSA-N 0.000 claims 1
- IYLIHNNFKPGARN-UHFFFAOYSA-N 2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]-N-(1,3-thiazol-2-yl)acetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CC(=O)NC=1SC=CN=1)O)C1=C(C=CC=C1OC)OC IYLIHNNFKPGARN-UHFFFAOYSA-N 0.000 claims 1
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- HDTFPWZMQGPBLM-UHFFFAOYSA-N 2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]-N-(2-methoxyethyl)acetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CC(=O)NCCOC)O)C1=C(C=CC=C1OC)OC HDTFPWZMQGPBLM-UHFFFAOYSA-N 0.000 claims 1
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- NPVXFRVWUHOYFD-UHFFFAOYSA-N 2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]-N-[(2-chlorophenyl)methyl]acetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CC(=O)NCC1=C(C=CC=C1)Cl)O)C1=C(C=CC=C1OC)OC NPVXFRVWUHOYFD-UHFFFAOYSA-N 0.000 claims 1
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- JGEOTWYEBZJJBZ-UHFFFAOYSA-N 3-(5-benzyl-1,3,4-oxadiazol-2-yl)-6-butyl-5-(2,6-dimethoxy-4-methylphenyl)-4-hydroxy-1H-pyridin-2-one Chemical compound C(C1=CC=CC=C1)C1=NN=C(O1)C=1C(=NC(=C(C=1O)C1=C(C=C(C=C1OC)C)OC)CCCC)O JGEOTWYEBZJJBZ-UHFFFAOYSA-N 0.000 claims 1
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- NJVOVFHVAKBPSE-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-2-chloro-N-methylbenzamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CN(C(C1=C(C=CC=C1)Cl)=O)C)O)C1=C(C=CC=C1OC)OC NJVOVFHVAKBPSE-UHFFFAOYSA-N 0.000 claims 1
- OEWJTPYNQPCUED-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-2-methoxyacetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(COC)=O)O)C1=C(C=CC=C1OC)OC OEWJTPYNQPCUED-UHFFFAOYSA-N 0.000 claims 1
- DEMDDYTXRAZFTP-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-2-phenylacetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(CC1=CC=CC=C1)=O)O)C1=C(C=CC=C1OC)OC DEMDDYTXRAZFTP-UHFFFAOYSA-N 0.000 claims 1
- STSQGDOWGRUREE-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-3-chloro-N-methylbenzamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CN(C(C1=CC(=CC=C1)Cl)=O)C)O)C1=C(C=CC=C1OC)OC STSQGDOWGRUREE-UHFFFAOYSA-N 0.000 claims 1
- ARXVIGGWAXYINK-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-3-chlorobenzamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(C1=CC(=CC=C1)Cl)=O)O)C1=C(C=CC=C1OC)OC ARXVIGGWAXYINK-UHFFFAOYSA-N 0.000 claims 1
- FSXDQJCUADZGHD-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-3-methylbutanamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(CC(C)C)=O)O)C1=C(C=CC=C1OC)OC FSXDQJCUADZGHD-UHFFFAOYSA-N 0.000 claims 1
- LYMXQEQHDVYNAB-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-4-chlorobenzamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(C1=CC=C(C=C1)Cl)=O)O)C1=C(C=CC=C1OC)OC LYMXQEQHDVYNAB-UHFFFAOYSA-N 0.000 claims 1
- NIJNZLWGUBLGNJ-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-N,2,2-trimethylpropanamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CN(C(C(C)(C)C)=O)C)O)C1=C(C=CC=C1OC)OC NIJNZLWGUBLGNJ-UHFFFAOYSA-N 0.000 claims 1
- DURSEIGZPMOUCU-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-N-methyl-2-phenylacetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CN(C(CC1=CC=CC=C1)=O)C)O)C1=C(C=CC=C1OC)OC DURSEIGZPMOUCU-UHFFFAOYSA-N 0.000 claims 1
- RXRKRPZATMCVSW-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-N-methylbenzamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CN(C(C1=CC=CC=C1)=O)C)O)C1=C(C=CC=C1OC)OC RXRKRPZATMCVSW-UHFFFAOYSA-N 0.000 claims 1
- RSPGPQZWACELRX-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-N-methylpyridine-2-carboxamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CN(C(=O)C1=NC=CC=C1)C)O)C1=C(C=CC=C1OC)OC RSPGPQZWACELRX-UHFFFAOYSA-N 0.000 claims 1
- KBVCGLMZVIFQPN-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-N-methylpyridine-3-carboxamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CN(C(=O)C=1C=NC=CC=1)C)O)C1=C(C=CC=C1OC)OC KBVCGLMZVIFQPN-UHFFFAOYSA-N 0.000 claims 1
- ZAVJXXFBCZDKMH-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-N-methylpyridine-4-carboxamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CN(C(=O)C1=CC=NC=C1)C)O)C1=C(C=CC=C1OC)OC ZAVJXXFBCZDKMH-UHFFFAOYSA-N 0.000 claims 1
- OITIQCLMFWSKMA-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]acetamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(C)=O)O)C1=C(C=CC=C1OC)OC OITIQCLMFWSKMA-UHFFFAOYSA-N 0.000 claims 1
- KCVLLUJHJQWYLV-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]benzamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(C1=CC=CC=C1)=O)O)C1=C(C=CC=C1OC)OC KCVLLUJHJQWYLV-UHFFFAOYSA-N 0.000 claims 1
- JYCGVBBBNOCZHL-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]pyridine-2-carboxamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(=O)C1=NC=CC=C1)O)C1=C(C=CC=C1OC)OC JYCGVBBBNOCZHL-UHFFFAOYSA-N 0.000 claims 1
- USLSCBCBMISAKC-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]pyridine-3-carboxamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(=O)C=1C=NC=CC=1)O)C1=C(C=CC=C1OC)OC USLSCBCBMISAKC-UHFFFAOYSA-N 0.000 claims 1
- KMLDKWAHUHAXRY-UHFFFAOYSA-N N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]pyridine-4-carboxamide Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(=O)C1=CC=NC=C1)O)C1=C(C=CC=C1OC)OC KMLDKWAHUHAXRY-UHFFFAOYSA-N 0.000 claims 1
- NSIGVTQWORQEBF-UHFFFAOYSA-N N-benzyl-2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]-N-methylacetamide Chemical compound C(C1=CC=CC=C1)N(C(CC=1OC(=NN=1)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O)=O)C NSIGVTQWORQEBF-UHFFFAOYSA-N 0.000 claims 1
- GKAZJEBNANKUAG-UHFFFAOYSA-N N-benzyl-2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]acetamide Chemical compound C(C1=CC=CC=C1)NC(CC=1OC(=NN=1)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O)=O GKAZJEBNANKUAG-UHFFFAOYSA-N 0.000 claims 1
- UHSAQAATXGJYAK-UHFFFAOYSA-N N-butyl-2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]acetamide Chemical compound C(CCC)NC(CC=1OC(=NN=1)C=1C(=NC(=C(C=1O)C1=C(C=CC=C1OC)OC)CCCC)O)=O UHSAQAATXGJYAK-UHFFFAOYSA-N 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000008253 Systolic Heart Failure Diseases 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 208000038003 heart failure with preserved ejection fraction Diseases 0.000 claims 1
- 208000018578 heart valve disease Diseases 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- FRQFCQGMLYGEIL-UHFFFAOYSA-N tert-butyl 2-[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]acetate Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CC(=O)OC(C)(C)C)O)C1=C(C=CC=C1OC)OC FRQFCQGMLYGEIL-UHFFFAOYSA-N 0.000 claims 1
- WPANTYJWXXBXDR-UHFFFAOYSA-N tert-butyl N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]-N-methylcarbamate Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CN(C(OC(C)(C)C)=O)C)O)C1=C(C=CC=C1OC)OC WPANTYJWXXBXDR-UHFFFAOYSA-N 0.000 claims 1
- NIGYIBAEQKNQHP-UHFFFAOYSA-N tert-butyl N-[[5-[6-butyl-5-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxo-1H-pyridin-3-yl]-1,3,4-oxadiazol-2-yl]methyl]carbamate Chemical compound C(CCC)C1=C(C(=C(C(=N1)O)C1=NN=C(O1)CNC(OC(C)(C)C)=O)O)C1=C(C=CC=C1OC)OC NIGYIBAEQKNQHP-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
- C07D413/02—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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
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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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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Claims (25)
1. Spoj formule (I):
ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
alk je C1-6 alkil supstituiran sa 0-5 Re;
prsten A je nezavisno odabran od:
i
prsten B je nezavisno odabran od:
R1 je nezavisno odabrano od: H, halogen, NO2, -(CH2)nORb,
(CH2)nS(O)pRc, -(CH2)nC(=O)Rb, -(CH2)nNRaRa, -(CH2)nCN, -(CH2)nC(=O)NRaR a, -(CH2)nNRaC(=O)Rb, -(CH2)nNRaC(=O)NRaRa, -(CH2)nNRaC(=O)ORb,-(CH2)nOC(=O)NRaRa, -(CH2)nC(=O)ORb, -(CH2)nS(O)pNRaRa,-(CH2)nNRaS(O)pNRaRa, -(CH2)nNRaS(O)pRc, C1-4 alkil supstituiran sa 0-3 Re,-(CH2)n-C3-6 karbociklil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
R2 je nezavisno odabrano od: C1-5 alkil supstituiran sa 0-3 Re; C2-5 alkenil supstituiran sa 0-3 Re, i C3-6 cikloalkil supstituiran sa 0-3 Re; pod uvjetom da kada R2 je C1-5 alkil, atom ugljika izuzev onog vezanog direktno za piridin prsten može biti zamijenjen sa O, N, i S;
R3 je nezavisno odabrano od:
(1) -(CR4R4)rC(=O)OC1-4 alkil supstituiran sa 0-5 Re,
(2) -(CR4R4)rNRaRa,
(3) -(CR4R4)rC(=O)NRaRa,
(4) -(CR4R4)rNRaC(=O)C1-4alkil supstituiran sa 0-5 Re,
(5) -(CR4R4)rNRaC(=O)(CR4R4)nOC1-4alkil supstituiran sa 0-5 Re,
(6) -(CR4R4)r-R5,
(7) -(CR4R4)r-OR5,
(8) -(CR4R4)rNR-C(=O)(CR4R4)nR5, i
(9) -(CR4R4)rC(=O)NRa(CR4R4)nR5;
R4 je nezavisno odabrano od: H, halogen, NRaRa, OC1-4alkil, i C1-4 alkil; ili R4 i R4 zajedno sa atomom ugljika za koji su oba povezana formiraju C3-6 cikloalkil supstituiran sa 0-5 Re;
R5 je nezavisno odabrano od: -(CH2)n-C3-10 karbociklus i -(CH2)n-heterociklus, svaki supstituiran sa 0-3 R6;
R6 je nezavisno odabrano od: H, halogen, =O, -(CH2)nORb,
(CH2)nS(O)pRc, -(CH2)nC(=O)Rb, -(CH2)nNRaRa, -(CH2)nCN, -(CH2)nC(=O)NRaR a, -(CH2)nNRaC(=O)Rb, -(CH2)nNRaC(=O)NRaRa, -(CH2)nNRaC(=O)ORb, -(CH2)nOC(=O)NRaRa, -(CH2)nC(=O)ORb, -(CH2)nS(O)pNRaRa, -(CH2)nNRaS(O)pNRaRa, -(CH2)nNRaS(O)pRc, C1-5 alkil supstituiran sa 0-3 Re, (CH2)n-C3-6 karbociklil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
Ra je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5 Re, C2-6 alkenil supstituiran sa 0-5 Re, C2-6 alkinil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re; ili Ra i Ra zajedno sa atomom dušika za koji su oba vezana formiraju heterociklični prsten supstituiran sa 0-5 Re;
Rb je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5 Re, C2-6 alkenil supstituiran sa 0-5 Re, C2-6 alkinil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re;
Rc je nezavisno odabrano od C1-6 alkil supstituiran sa 0-5 Re, C2-6alkenil supstituiran sa 0-5 Re, C2-6alkinil supstituiran sa 0-5 Re, C3-6karbociklil, i heterociklil;
Rd je nezavisno odabrano od H i C1-4alkil supstituiran sa 0-5 Re;
Re je nezavisno odabrano od C1-6 alkil supstituiran sa 0-5 Rf, C2-6 alkenil, C2-6 alkinil, -(CH2)n-C3-6 cikloalkil, -(CH2)n-C4-6
heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H, -(CH2)nORf, S(O)pRf, C(=O)NRfRf, NRfC(=O)Rf, S(O)pNRfRf, NRfS(O)pRf, NRfC(=O)ORf, OC(=O)NRfRf i -(CH2)nNRfRf;
Rf je nezavisno odabrano od H, F, Cl, Br, CN, OH, C1-5alkil (optimalno supstituiran sa halogen i OH), C3-6 cikloalkil, i fenil, ili Rf i Rf zajedno sa atomom dušika za koji su oba vezana formiraju heterociklični prsten po izboru supstituiran sa C1-4alkil grupom;
n je nezavisno odabrano od nula,1, 2, i 3;
r je nezavisno odabrano od nula,1, 2, i 3; i
p je nezavisno odabrano od nula, 1, i 2.
2. Spoj u skladu sa patentnim zahtjevom 1 koje ima Formulu (II):
ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
R1 je nezavisno odabrano od: F, Cl, Br,
NO2, -(CH2)nORb, -(CH2)nC(=O)Rb, -(CH2)nNRaRa, -(CH2)nC(=O)NRaRa, -(CH2)n NRaC(=O)Rb, C1-4 alkil supstituiran sa 0-3 Re i C3-6 cikloalkil supstituiran sa 0-3 Re;
R2 je nezavisno odabrano od: C1-5 alkil supstituiran sa 0-3 Re; C2-5 alkenil, i C3-6 cikloalkil; pod uvjetom da kada R2 je C1-5alkil, atom ugljika izuzev onog vezanog direktno za piridin prsten može biti zamijenjen sa O i S;
R3 je nezavisno odabrano od:
(1) -(CR4R4)rC(=O)OC1-4 alkil supstituiran sa 0-5 Re,
(2) -(CR4R4)rNRaRa,
(3) -(CR4R4)rC(=O)NRaRa,
(4) -(CR4R4)rNRaC(=O)C1-4alkil supstituiran sa 0-5 Re,
(5) -(CR4R4)rNRaC(=O)(CR4R4)nOC1-4alkil supstituiran sa 0-5 Re,
(6) -(CR4R4)r-R5,
(7) -(CR4R4)r-OR5,
(8) -(CR4R4)rNRaC(=O)(CR4R4)nR5, i
(9) -(CR4R4)rC(=O)NRa(CR4R4)nR5;
R4 je nezavisno odabrano od: H, F, Cl, NRaRa, OC1-4 alkil, i C1-4 alkil; ili R4 i R4 zajedno sa atomom ugljika za koji su oba povezana formiraju C3-6 cikloalkil supstituiran sa 0-5 Re;
R5 je nezavisno odabrano od: -(CH2)n-aril, -(CH2)n-C3-6cikloalkil i -(CH2)n-heterociklus, svaki supstituiran sa 0-3 R6;
R6 je nezavisno odabrano od: H, F, Cl, Br, -ORb,
=O, -(CH2)nC(=O)Rb, -(CH2)nC(=O)ORb, -(CH2)nNRaRa,
CN, -(CH2)nC(=O)NRaRa, -(CH2)nS(O)pNRaRa, C1-4 alkil supstituiran sa 0-3 Re, (CH2)n-C3-6 karbociklil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
Ra je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re; ili Ra i Ra zajedno sa atomom dušika za koji su oba vezana formiraju heterociklični prsten supstituiran sa 0-5 Re;
Rb je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5 Re, C2-6 alkenil supstituiran sa 0-5 Re, C2-6 alkinil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re;
Re je nezavisno odabrano od C1-6 alkil supstituiran sa 0-5 Rf, C2-6 alkenil, C2-6 alkinil, -(CH2)n-C3-6 cikloalkil, -(CH2)n-C4-6
heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H, -(CH2)nORf, S(O)pRf, C(=O)NRfRf, NRfC(=O)Rf, S(O)pNRfRf, NRfS(O)pRf, NRfC(=O)ORf, OC(=O)NRfRf i -(CH2)nNRfRf;
Rf je nezavisno odabrano od H, F, Cl, Br, CN, OH, C1-5alkil (optimalno supstituiran sa halogen i OH), C3-6 cikloalkil, i fenil;
n je nezavisno odabrano od nula,1, 2, i 3;
r je nezavisno odabrano od 1, 2, i 3; i
p je nezavisno odabrano od nula, 1, i 2.
3. Spoj u skladu sa bilo kojim od patentnih zahtjeva 1-2 koje ima Formulu (III):
ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
R1 je nezavisno odabrano od: F, Cl, OH, i OC1-4 alkil;
R1a je nezavisno odabrano od: F, Cl, i C1-2 alkil;
R2 je nezavisno odabrano od: C1-5 alkil supstituiran sa 0-3 Re; C2-5 alkenil, i C3-6 cikloalkil i CH2O(CH2)1-3CH3;
R3 je nezavisno odabrano od:
(1) -(CR4R4)rC(=O)OC1-4 alkil supstituiran sa 0-5 Re,
(2) -(CR4R4)rNRaRa,
(3) -(CR4R4)rC(=O)NRaRa,
(4) -(CR4R4)rNRaC(=O) C1-4alkil supstituiran sa 0-5 Re,
(5) -(CR4R4)rNRaC(=O)(CR4R4)nOC1-4alkil supstituiran sa 0-5 Re,
(6) -(CR4R4)r-R5,
(7) -(CR4R4)r-OR5, i
(8) -(CR4R4)rNRaC(=O)(CR4R4)nR5, i
(9) -(CR4R4)rC(=O)NRa(CR4R4)nR5;
R4 je nezavisno odabrano od: H, F, Cl, NRaRa, OC1-4 alkil, i C1-4 alkil; ili R4 i R4 zajedno sa atomom ugljika za koji su oba povezana formiraju C3-6 cikloalkil supstituiran sa 0-5 Re;
R5 je nezavisno odabrano od: -(CH2)n-aril, -(CH2)n-C3-6cikloalkil i -(CH2)n-heterociklus, svaki supstituiran sa 0-3 R6;
R6 je nezavisno odabrano od: H, F, Cl, Br, -ORb,
=O, -(CH2)nC(=O)Rb, -(CH2)nC(=O)ORb, -(CH2)nNRaRa, CN, -(CH2)nC(=O)NRaRa, -(CH2)nS(O)pNRaRa, C1-4 alkil supstituiran sa 0-3 Re, (CH2)n-C3-6 karbociklil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
Ra je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re; ili Ra i Ra zajedno sa atomom dušika za koji su oba vezana formiraju heterociklični prsten supstituiran sa 0-5 Re;
Rb je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5 Re, C2-6 alkenil supstituiran sa 0-5 Re, C2-6 alkinil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re;
Re je nezavisno odabrano od C1-6 alkil (po izboru supstituiran sa F i Cl), OH, OCH3, OCF3, -(CH2)n-C3-6cikloalkil, -(CH2)n-C4-6
heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H; i
n je nezavisno odabrano od nula,1, 2, i 3; i
r je nezavisno odabrano od 1, 2, i 3.
4. Spoj u skladu sa bilo kojim od patentnih zahtjeva 1-3 ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
R3 je nezavisno odabrano od:
(1) -(CR4R4)r-R5,
(2) -(CR4R4)r-OR5,
(3) -(CR4R4)rNRaC(=O)(CR4R4)nR5, i
(4) -(CR4R4)rC(=O)NRa(CR4R4)nR5;
R4 je nezavisno odabrano od: H, F, Cl, N(CH3)2, OCH3, i CH3; ili R4 i R4 zajedno sa atomom ugljika za koji su oba povezana formiraju ciklopropil;
R5 je nezavisno odabrano od:
R6 je nezavisno odabrano od: H, F, Cl, Br, -OCH3, -OCF3, =O, -NRaRa, CN, - S(O)2NH2, CH3, CF3 -(CH2)n-aril, -(CH2)n-C3-6 cikloalkil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
R6a je nezavisno odabrano od: H, CH3, aril supstituiran sa 0-3 Re, i heterociklil supstituiran sa 0-3 Re;
Ra je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re;
Re je nezavisno odabrano od C1-6 alkil (po izboru supstituiran sa F i Cl), OH, OCH3, OCF3, -(CH2)n-C3-6cikloalkil, -(CH2)n-C4-6 heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H;
n je nezavisno odabrano od nula,1, 2, i 3; i
r je nezavisno odabrano od 1, 2, i 3.
5. Spoj u skladu sa bilo kojim od patentnih zahtjeva 1-3 ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
R3 je nezavisno odabrano od:
(1) -(CR4R4)rNRaRa, i
(2) -(CR4R4)rC(=O)NRaRa,
R4 je nezavisno odabrano od: H, F, C, N(CH3)2, OCH3, i CH3; ili R4 i R4 zajedno sa atomom ugljika za koji su oba povezana formiraju C3-6 cikloalkil supstituiran sa 0-5 Re;
R6 je nezavisno odabrano od: H, F, Cl, Br, -OCH3, -OCF3, =O, CN, -NRaRa, - S(O)2NH2, -CH3, CF3 -(CH2)n-aril, -(CH2)n-C3-6 cikloalkil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
R6a je nezavisno odabrano od: H, CH3, aril supstituiran sa 0-3 Re, i heterociklil supstituiran sa 0-3 Re;
Ra i Ra zajedno sa atomom dušika za koji su oba vezana formiraju heterociklični prsten supstituiran sa 0-5 Re, pri čemu heterociklični prsten je odabran od:
i
Re je nezavisno odabrano od C1-6 alkil (po izboru supstituiran sa F i Cl), OH, OCH3, OCF3, -(CH2)n-C3-6cikloalkil, -(CH2)n-C4-6
heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H;
n je nezavisno odabrano od nula,1, 2, i 3; i
r je nezavisno odabrano od 1, 2, i 3.
6. Spoj u skladu sa bilo kojim od patentnih zahtjeva 1-3, ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
R1 je nezavisno odabrano od: F, Cl, OH, i OC1-4 alkil;
R1a je nezavisno odabrano od: F, Cl, i C1-2 alkil;
R2 je nezavisno odabrano od: C1-5 alkil supstituiran sa 0-3 Re; C2-5 alkenil, i C3-6 cikloalkil; i CH2O(CH2)1-3CH3;
R3 je nezavisno odabrano od:
(1) -(CH2)rC(=O)OC1-4 alkil supstituiran sa 0-3 Re,
(2) -(CH2)rNRaRa,
(3) -(CH2)rC(=O)NRaRa,
(4) -(CH2)rNRaC(=O)C1-4alkil supstituiran sa 0-3 Re, i
(5) -(CH2)rNRaC(=O)(CR4R4)nOC1-4alkil supstituiran sa 0-3 Re;
R4 je nezavisno odabrano od: H, F, Cl, NRaRa, OC1-4 alkil, i C1-4 alkil;
R5 je nezavisno odabrano od: -(CH2)n-aril, -(CH2)n-C3-6cikloalkil i -(CH2)n-heterociklus, svaki supstituiran sa 0-3 R6;
R6 je nezavisno odabrano od: H, F, Cl, Br, -OCH3, -OCF3, =O, CN, -NRaRa, - S(O)2NH2, CH3, CF3 -(CH2)n-aril, -(CH2)n-C3-6 cikloalkil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
Ra je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re;
Re je nezavisno odabrano od C1-6 alkil (po izboru supstituiran sa F i Cl), OH, OCH3, OCF3, -(CH2)n-C3-6cikloalkil, -(CH2)n-C4-6
heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H;
n je nezavisno odabrano od nula,1, 2, i 3; i
r je nezavisno odabrano od 1, 2, i 3.
7. Spoj u skladu sa bilo kojim od patentnih zahtjeva 1-2 koje ima Formulu (IVa):
ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
R1 je nezavisno odabrano od: -CH2OH, -OCH3, -OCF3,OCH2F, -C(=O)NRaRa, - NRaRa, CH3, CH2CH3, CH(CH3)2, i ciklopropil;
R2 je nezavisno odabrano od: C1-4 alkil supstituiran sa 0-3 Re; C2-4 alkenil, C3-6 cikloalkil, i CH2O(CH2)1-3CH3;
R3 je nezavisno odabrano od:
(1) -(CR4R4)rC(=O)OC1-4 alkil supstituiran sa 0-3 Re,
(2) -(CR4R4)rNRaRa,
(3) -(CR4R4)rC(=O)NRaRa,
(4) -(CR4R4)rNRaC(=O)C1-4alkil supstituiran sa 0-3 Re,
(5) -(CR4R4)rNRaC(=O)(CR4R4)nOC1-4alkil supstituiran sa 0-3 Re,
(6) -(CR4R4)r-R5,
(7) -(CR4R4)r-OR5,
(8) -(CR4R4)rNRaC(=O)(CR4R4)nR5, i
(9) -(CR4R4)rC(=O)NRa(CR4R4).R5;
R4 je nezavisno odabrano od: H, F, Cl, NRaRa, OC1-4 alkil, i C1-4 alkil;
R5 je nezavisno odabrano od: aril, C3-6 cikloalkil i heterociklus, svaki supstituiran sa 0-3 R6;
R6 je nezavisno odabrano od: H, F, Cl, Br, -ORb,
=O, -(CH2)nC(=O)Rb, -(CH2)nC(=O)ORb, -(CH2)nNRaRa,
CN, -(CH2)nC(=O)NRaRa, C1-4 alkil supstituiran sa 0-3 Re, (CH2)n-C3-6 karbociklil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
Ra je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re; ili Ra i Ra zajedno sa atomom dušika za koji su oba vezana formiraju heterociklični prsten supstituiran sa 0-5 Re;
Rb je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5 Re, C2-6 alkenil supstituiran sa 0-5 Re, C2-6 alkinil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re;
Re je nezavisno odabrano od C1-6 alkil (po izboru supstituiran sa F i Cl), OH, OCH3, OCF3, -(CH2)n-C3-6cikloalkil, -(CH2)n-C4-6
heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H;
n je nezavisno odabrano od nula,1, 2, i 3; i
r je nezavisno odabrano od 1, 2, i 3.
8. Spoj u skladu sa bilo kojim od patentnih zahtjeva 1-2 koje ima Formulu (V):
ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
R1 je nezavisno odabrano od: -CH2OH, -OCH3, -OCF3, CH3, CH2CH3, CH(CH3)2, i ciklopropil;
R2 je nezavisno odabrano od: C1-4 alkil supstituiran sa 0-3 Re; C2-4 alkenil, C3-6 cikloalkil, i CH2O(CH2)1-3CH3;
R3 je nezavisno odabrano od:
(1) -CH2C(=O)OC1-4 alkil supstituiran sa 0-3 Re,
(2) -CH2NRaRa,
(3) -CH2C(=O)NRaRa,
(4) -CH2NHC(=O)C1-4alkil supstituiran sa 0-3 Re,
(5) -CH2NRaC(=O)(CH2)0-2OC1-4alkil supstituiran sa 0-3 Re,
(6) -CH2-R5,
(7) -CH2-OR5,
(8) -CH2NRaC(=O)(CH2)0-2R5, i
(9) -CH2C(=O)NRa(CH2)0-2R5;
R5 je nezavisno odabrano od: aril, C3-6 cikloalkil i heterociklus, svaki supstituiran sa 0-3 R6;
R6 je nezavisno odabrano od: H, F, Cl, Br, -ORb,
=O, -(CH2)nC(=O)Rb, -(CH2)nC(=O)ORb, -(CH2)nNRaRa, CN, -(CH2)nC(=O)NRaRa, -S(O)2NH2, C1-4 alkil supstituiran sa 0-3 Re, (CH2)n-C3-6 karbociklil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
Ra je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re; ili Ra i Ra zajedno sa atomom dušika za koji su oba vezana formiraju heterociklični prsten supstituiran sa 0-5 Re;
Rb je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5 Re, C2-6 alkenil supstituiran sa 0-5 Re, C2-6 alkinil supstituiran sa 0-5 Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re;
Re je nezavisno odabrano od C1-6 alkil (po izboru supstituiran sa F i Cl), OH, OCH3, OCF3, -(CH2)n-C3-6cikloalkil, -(CH2)n-C4-6 heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H;
n je nezavisno odabrano od nula,1, 2, i 3.
9. Spoj u skladu sa patentnim zahtjevom 8 ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
R3 je nezavisno odabrano od:
(1) -CH2-R5,
(2) -CH2-OR5,
(3) -CH2-NHC(=O)(CH2)0-1R5, i
(4) -CH2-C(=O)NH(CH2)0-1R5;
R5 je nezavisno odabrano od:
R6 je nezavisno odabrano od: H, F, Cl, Br, -OCH3, -OCF3, =O, CN, CH3, CF3 - (CH2)n-aril, -(CH2)n-C3-6 cikloalkil supstituiran sa 0-3 Re,
i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
R6a je nezavisno odabrano od: H, CH3, aril supstituiran sa 0-3 Re, i heterociklil supstituiran sa 0-3 Re;
Ra je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re;
Re je nezavisno odabrano od C1-6 alkil (po izboru supstituiran sa F i Cl), OH, OCH3, OCF3, -(CH2)n-C3-6cikloalkil, -(CH2)n-C4-6
heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H;
n je nezavisno odabrano od nula,1, 2, i 3.
10. Spoj u skladu sa patentnim zahtjevom 1 koje ima Formulu (VI):
ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljiva sol, pri čemu:
R1 je nezavisno odabrano od: F, Cl, Br,
NO2, -(CH2)nORb, -(CH2)nC(=O)Rb, -(CH2)nNRaRa, -(CH2)nC(=O)NRaRa, -(CH2)n NRaC(=O)Rb, C1-4 alkil supstituiran sa 0-3 Re i C3-6 cikloalkil supstituiran sa 0-3 Re;
R2 je nezavisno odabrano od: C1-5 alkil supstituiran sa 0-3 Re; C2-5 alkenil, i C3-6 cikloalkil; pod uvjetom da kada R2 je C1-5alkil, atom ugljika izuzev onog vezanog direktno za piridin prsten može biti zamijenjen sa O, N, i S;
R3 je nezavisno odabrano od:
(1) -CH2C(=O)OC1-4 alkil supstituiran sa 0-5 Re,
(2) -CH2NRaRa,
(3) -CH2C(=O)NRaRa,
(4) -CH2NRaC(=O)C1-4alkil supstituiran sa 0-5 Re,
(5) -CH2NaRC(=O)( CH2)nOC1-4alkil supstituiran sa 0-5 Re,
(6) -CH2-R5,
(7) -CH2-OR5,
(8) -CH2NRC(=O)(CH2)nR5, i
(9) -CH2C(=O)NRa(CH2)nR5
R5 je nezavisno odabrano od: -(CH2)n-aril, -(CH2)n-C3-6cikloalkil i -(CH2)n-heterociklus, svaki supstituiran sa 0-3 R6;
R6 je nezavisno odabrano od: H, F, Cl, Br, -ORb,
=O, -(CH2)nC(=O)Rb, -(CH2)nC(=O)ORb, -(CH2)nNRaRa,
CN, -(CH2)nC(=O)NRaRa, C1-4 alkil supstituiran sa 0-3 Re, (CH2)n-C3-6 karbociklil supstituiran sa 0-3 Re, i -(CH2)n-heterociklil supstituiran sa 0-3 Re;
Ra je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re; ili Ra i Ra zajedno sa atomom dušika za koji su oba vezana formiraju heterociklični prsten supstituiran sa 0-5 Re;
Rb je nezavisno odabrano od H, C1-6 alkil supstituiran sa 0-5 Re, C2-6 alkenil supstituiran sa 0-5 Re, C2-6 alkinil supstituiran sa 0-5
Re, -(CH2)n-C3-10karbociklil supstituiran sa 0-5 Re, i -(CH2)n-heterociklil supstituiran sa 0-5 Re;
Re je nezavisno odabrano od C1-6 alkil supstituiran sa 0-5 Rf, C2-6 alkenil, C2-6 alkinil, -(CH2)n-C3-6 cikloalkil, -(CH2)n-C4-6
heterociklil, -(CH2)n-aril, -(CH2)n-heteroaril, F, Cl, Br, CN, NO2, =O, CO2H, -(CH2)nORf, S(O)pRf, C(=O)NRfRf, NRfC(=O)Rf, S(O)pNRfRf, NRfS(O)pRf, NRfC(=O)ORf, OC(=O)NRfRf i -(CH2)nNRfRf;
Rf je nezavisno odabrano od H, F, Cl, Br, CN, OH, C1-5alkil (optimalno supstituiran sa halogen i OH), C3-6 cikloalkil, i fenil;
n je nezavisno odabrano od nula,1, 2, i 3; i
p je nezavisno odabrano od nula, 1, i 2.
11. Spoj u skladu sa patentnim zahtjevom 1 odabrano iz grupe koja se sastoji od:
3-(5-benzil-1,3,4-oksadiazol-2-il)-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-(5-benzil-1,3,4-oksadiazol-2-il)-6-butil-5-(2,6-dimetoksi-4-metilfenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(piridin-4-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(2-feniletil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-3- {5-[(2-klorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3- {5-[(2-metoksifenil)metil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3- {5-[(3-metoksifenil)metil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-3- {5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(4-metoksifenil)metil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-3-[5-(3-klorofenil)-1,3,4-oksadiazol-2-il]-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-[5-(2-klorofenil)-1,3,4-oksadiazol-2-il]-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(pirazin-2-il)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(1-fenilciklopropil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-3-(5-ciklopropil-1,3,4-oksadiazol-2-il)-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(2-fenilpropan-2-il)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(piridin-3-il)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(fenoksimetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
3-(5-benzil-1,3,4-oksadiazol-2-il)-6-(but-3-en-1-il)-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(5-metil-1H-pirazol-3-il)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(pirazin-2-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(pirimidin-5-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-3- {5-[(3-klorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-{5-[difluoro(fenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-[5-(1,3-benzoksazol-2-ilmetil)-1,3,4-oksadiazol-2-il]-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-butil-5-(2,6-dimetoksi-4-metilfenil)piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-(but-3-en-1-il)-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[2-(5-fenil-1,3-oksazol-2-il)etil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[2-(1-metil-1H-imidazol-2-il)etil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-3-{5-[(6-kloropiridin-3-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-{5-[2-(4-klorofenil)propan-2-il]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(4-fluorofenil)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-3- {5-[(3,4-diklorofenil)metil]-1,3,4-oksadiazol-2-il} -5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[4-fluoro-3-(trifluorometil)fenil]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-3-{5-[(2,4-diklorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(3,5-dimetil-1H-pirazol-4-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
4-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il} metil)benzonitril,
6-butil-3-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-(5-{[2-(4-klorofenil)-1,3-tiazol-4-il]metil}-1,3,4-oksadiazol-2-il)-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-{5-[1-(4-klorofenil)etil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(4-metil-1,2,5-oksadiazol-3-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(4-fluorofenoksimetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(1H-indazol-3-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
4-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il} metil)-1,2-dihidroftalazin-1-on,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[metoksi(fenil)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(2-fenil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
3-{5-[2-(1,3-benzoksazol-2-il)etil]-1,3,4-oksadiazol-2-il}-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3- {5-[(4-fluoro-3-metoksifenil)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(1,3-tiazol-5-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-3-[5-(3,4-diklorofenoksimetil)-1,3,4-oksadiazol-2-il]-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(3-metil-1,2-oksazol-5-il)metil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{2-[3-(pirazin-2-il)-1,2,4-oksadiazol-5-il]etil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-3-[5-(4-klorofenoksimetil)-1,3,4-oksadiazol-2-il]-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-{5-[2-(4-klorofenil)-2-metilpropil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[3-(piridin-2-il)-1,2,4-oksadiazol-5-il]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[4-(trifluorometoksi)fenil]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[3-fluoro-5-(trifluorometil)fenil]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[2-(1-metil-1H-1,3-benzodiazol-2-il)etil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-3- {5-[(2-kloropiridin-4-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{2-[3-(4-metoksifenil)-1,2,4-oksadiazol-5-il]etil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(1,2,3,4-tetrahidroizohinolin-1-il)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-3-{5-[2-(3,4-diklorofenil)propan-2-il]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3- {5-[(2-metil-2H-1,2,3,4-tetrazol-5-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(2-metil-1-fenilpropan-2-il)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3- {5-[4-(trifluorometil)fenoksimetil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(5-fenil-4H-1,2,4-triazol-3-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-3-[5-(cikloheksilmetil)-1,3,4-oksadiazol-2-il]-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-{5-[2-(4-klorofenil)etil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(oksan-4-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-3- {5-[(3-kloro-4-fluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3- {5-[(4-kloro-3-fluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[2-(1,3-tiazol-2-il)etil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[3-(trifluorometil)fenil]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-3-{5-[2-(3,4-difluorofenil)etil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{2-[4-(trifluorometil)fenil]etil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-3-[5-(3,4-difluorofenoksimetil)-1,3,4-oksadiazol-2-il]-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3- {5-[2-(3-fenil-1,2,4-oksadiazol-5-il)etil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(1-fenil-1H-pirazol-4-il)metil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[4-(trifluorometil)fenil]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3- {5-[2-(pirimidin-2-il)etil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
3-{5-[2-(1,3-benzotiazol-2-il)etil]-1,3,4-oksadiazol-2-il}-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{2-[3-(piridin-2-il)-1,2,4-oksadiazol-5-il]etil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(5-metil-2-fenil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-3-{5-[2-(3,4-diklorofenil)etil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-butil-5-(2,6-diklorofenil)piridin-2,4-diol,
6-butil-3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-diklorofenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(dimetilamino)(4-fluorofenil)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(5-metil-2-fenil-1,3-oksazol-4-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-ciklopropil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-6-ciklopropil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-ciklopropil-5-(2,6-dimetoksifenil)-3-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-ciklopropil-5-(2,6-dimetoksifenil)-3-(5-{[3-(piridin-2-il)-1,2,4-oksadiazol-5-il]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
etil 2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il} acetat,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(1,3-dimetil-1H-pirazol-5-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
3-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-1-metilimidazolidin-2,4-dion,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(3-fluorofenil)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(piperidin-1-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[3-(piridin-3-il)-1,2,4-oksadiazol-5-il]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(1-metil-1H-pirazol-4-il)metil]-1,3,4-oksadiazol-2-il} piridin-2,4-diol,
6-butil-3-{5-[(4-kloro-2-fluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[3-(piridin-4-il)-1,2,4-oksadiazol-5-il]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
1-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)pirolidin-2-on,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-(5-{[5-(piridin-2-il)-1,2,4-oksadiazol-3-il]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
3-{5-[(3-benzil-1,2,4-oksadiazol-5-il)metil]-1,3,4-oksadiazol-2-il}-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-{5-[(3-ciklopropil-1,2,4-oksadiazol-5-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(6-kloropiridin-3-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(3-fenil-1,2,4-oksadiazol-5-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
1-({5-[5-(2,6-dimetoksifenil)-6-(etoksimetil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il} metil)pirolidin-2-on,
3-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il} metil)imidazolidin-2,4-dion,
1-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-1,2-dihidropiridin-2-on,
6-butil-5-(2,6-dimetoksifenil)-3-[5-(1H-imidazol-1-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
3-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il} metil)-1,3-oksazolidin-2-on,
4-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il} metil)morfolin-3 -on,
terc-butil 2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}acetat,
1-({5-[5-(2,6-dimetoksifenil)-6-(etoksimetil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-1,2-dihidropiridin-2-on,
terc-butil N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)karbamat,
terc-butil N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-N-metilkarbamat,
3-{5-[(4-kloro-3-fluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
3-{5-[(4-kloro-2-fluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-{5-[(5-fluoropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-[5-(1H-imidazol-1-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-{5-[(3-fluoro-4-metilfenil)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
3-{5-[(5-kloropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-{5-[(3-fenil-1H-pirazol-1-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-(5-{[3-(trifluorometil)-1H-pirazol-1-il]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-{5-[(1-metil-1H-pirazol-4-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-{5-[(6-fluoropiridin-3-il)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-[5-(1H-indazol-3-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
3-[5-(1H-1,2,3-benzotriazol-1-ilmetil)-1,3,4-oksadiazol-2-il]-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-[5-(1H-indazol-1-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-{5-[(4-fluorofenil)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-[5-(1H-indol-1-ilmetil)-1,3,4-oksadiazol-2-il]piridin-2,4-diol,
6-butil-5-(3-etilfenil)-4-hidroksi-3-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}-1,2-dihidropiridin-2-on,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-butil-5-fenilpiridin-2,4-diol,
6-butil-3-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(3-metoksifenil)piridin-2,4-diol,
6-butil-3-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(3-etilfenil)piridin-2,4-diol,
6-butil-3-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-[3-(trifluorometoksi)fenil]piridin-2,4-diol,
5-[3-(benziloksi)fenil]-6-butil-3-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-3-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-[3-(hidroksimetil)fenil]piridin-2,4-diol,
6-butil-5-(cikloheks-1-en-1-il)-3-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
6-butil-3-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-[3-(propan-2-il)fenil]piridin-2,4-diol,
6-butil-3-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}-5-[3-(metoksimetil)fenil]piridin-2,4-diol,
3-(2-butil-5-{5-[(3,4-difluorofenil)metil]-1,3,4-oksadiazol-2-il}-4,6-dihidroksipiridin-3-il)-N-(propan-2-il)benzamid,
6-butil-4-hidroksi-3-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}-5-[3-(propan-2-il)fenil]-1,2-dihidropiridin-2-on,
3-(2-butil-4-hidroksi-5-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}-6-okso-1,6-dihidropiridin-3-il)-N-(propan-2-il)benzamid,
6-butil-5-(3-ciklopropilfenil)-4-hidroksi-3-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}-1,2-dihidropiridin-2-on,
6-butil-4-hidroksi-5-(3-metoksifenil)-3-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}-1,2-dihidropiridin-2-on,
6-butil-4-hidroksi-5-[3-(hidroksimetil)fenil]-3-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}-1,2-dihidropiridin-2-on,
6-butil-4-hidroksi-3-{5-[(2-metil-1,3-tiazol-4-il)metil]-1,3,4-oksadiazol-2-il}-5-[3-(pirolidin-1-il)fenil]-1,2-dihidropiridin-2-on,
6-butil-5-(2,6-dimetoksifenil)-3-{5-[(metilamino)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-N-metil-2-fenilacetamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-3-kloro-N-metilbenzamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-N-metilpiridin-2-karboksamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-2-metoksiacetamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-N-metilpiridin-4-karboksamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)piridin-3-karboksamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-2-kloro-N-metilbenzamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-3-klorobenzamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-4-klorobenzamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)piridin-4-karboksamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-N-metilpiridin-3-karboksamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-2-fenilacetamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-2,2-dimetilpropanamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)piridin-2-karboksamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-N,2,2-trimetilpropanamid,
3-[5-(aminometil)-1,3,4-oksadiazol-2-il]-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)benzamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-N-metilbenzamid,
N-({5-[5-(2,6-dimetoksifenil)-6-(etoksimetil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)benzamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-3-metilbutanamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)acetamid,
N-({5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-2,2,2-trifluoroacetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N,N-dietilacetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(piridin-2-ilmetil)acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-metilacetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(propan-2-il)acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N,N-dimetilacetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(4-metoksifenil)acetamid,
4-(2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}acetil)piperazin-2-on,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-1-(4-metilpiperazin-1-il)etan-1-on,
N-benzil-2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-etilacetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-ciklopropilacetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-propilacetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(2-fluoroetil)acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(2,2-difluoroetil)acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(2,2,2-trifluoroetil)acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(2-metoksietil)acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-1-(pirolidin-1-il)etan-1-on,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-1-(piperidin-1-il)etan-1-on,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-1-(morfolin-4-il)etan-1-on,
N-butil-2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-pentilacetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-1-(3-fluoroazetidin-1-il)etan-1-on,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-1-(3,3-difluoroazetidin-1-il)etan-1-on,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(1,3-tiazol-2-il)acetamid,
3-(3-benzil-1,2,4-oksadiazol-5-il)-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-{3-[(4-klorofenil)metil]-1,2,4-oksadiazol-5-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-(5-benzil-4H-1,2,4-triazol-3-il)-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-(5-{[5-(4-klorofenil)-1,3,4-oksadiazol-2-il]metil}-1,3,4-oksadiazol-2-il)-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[5-(piridin-4-il)-1,3,4-oksadiazol-2-il]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[5-(piridin-2-il)-1,3,4-oksadiazol-2-il]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
6-butil-3-(5-{[5-(2-klorofenil)-1,3,4-oksadiazol-2-il]metil}-1,3,4-oksadiazol-2-il)-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(5-benzil-1,3,4-oksadiazol-2-il)metil]-1,3,4-oksadiazol-2-il}-6-butil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-3-(5-{[5-(3-klorofenil)-1,3,4-oksadiazol-2-il]metil}-1,3,4-oksadiazol-2-il)-5-(2,6-dimetoksifenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[5-(piridin-3-il)-1,3,4-oksadiazol-2-il]metil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
1-({5-[6-(etoksimetil)-5-(4-fluoro-2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)-1,2-dihidropiridin-2-on,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-(etoksimetil)-5-(4-fluoro-2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-6-(etoksimetil)-5-(4-fluoro-2,6-dimetoksifenil)piridin-2,4-diol,
1-({5-[6-(etoksimetil)-5-(4-fluoro-2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)pirolidin-2-on,
3-{5-[(6-kloropiridin-3-il)metil]-1,3,4-oksadiazol-2-il}-6-(etoksimetil)-5-(4-fluoro-2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(3,5-dimetoksipiridin-4-il)-6-(etoksimetil)piridin-2,4-diol,
6-butil-3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(3-fluoro-2,6-dimetoksifenil)piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-butil-5-(3-fluoro-2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-6-(etoksimetil)-5-(2-hidroksi-6-metoksifenil)piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-butil-5-(2,6-dimetilfenil)piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-butil-5-(2,4,6-trimetilfenil)piridin-2,4-diol,
3-[5-(1,2-benzoksazol-3-ilmetil)-1,3,4-oksadiazol-2-il]-6-butil-5-(2,6-dietilfenil)piridin-2,4-diol,
6-butil-5-(2,6-dimetoksifenil)-3-(5-{[1,2]oksazolo[4,5-b]piridin-3-ilmetil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-(5-{[1,2]oksazolo[4,5-b]piridin-3-ilmetil}-1,3,4-oksadiazol-2-il)piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dihidroksifenil)-6-(etoksimetil)piridin-2,4-diol,
3-{5-[(5-kloropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-[(etilamino)metil]piridin-2,4-diol,
3-{5-[(1,2-benzoksazol-3-il)metil]-1,3,4-tiadiazol-2-il}-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
3-{5-[(5-kloropiridin-2-il)metil]-1,3,4-tiadiazol-2-il}-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
3-{5-[(5-kloropiridin-2-il)metil]-1,3,4-tiadiazol-2-il}-6-ciklopentil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-tiadiazol-2-il}-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
N-({5-[5-(2,6-dimetoksifenil)-6-(etoksimetil)-2,4-dihidroksipiridin-3-il]-1,3,4-tiadiazol-2-il}metil)piridin-2-karboksamid,
6-butil-3-{5-[(5-kloro-3-fluoropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(5-kloro-3-fluoropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-(etoksimetil)piridin-2,4-diol,
3-{5-[(5-kloropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}-6-ciklopentil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-6-ciklopentil-5-(2,6-dimetoksifenil)piridin-2,4-diol,
3-{5-[(5-kloropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-[(2-metoksietoksi)metil]piridin-2,4-diol,
3-{5-[(1,2-benzoksazol-3-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-[(2-metoksietoksi)metil]piridin-2,4-diol,
5-(2,6-dimetoksifenil)-6-(etoksimetil)-3-{5-[(fenilamino)metil]-1,3,4-oksadiazol-2-il}piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dimetoksifenil)-6-[(2-metoksietoksi)metil]piridin-2,4-diol,
N-({5-[6-butil-5-(2,5-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)benzamid,
N-[(5-{6-butil-2,4-dihidroksi-5-[2-metoksi-5-(propan-2-il)fenil]piridin-3-il}-1,3,4-oksadiazol-2-il)metil]benzamid,
3-{5-[(1,2-benzoksazol-3-il)metil]-1,3,4-oksadiazol-2-il}-6-(etoksimetil)-5-(2-metoksifenil)piridin-2,4-diol,
3-{5-[(4-klorofenil)metil]-1,3,4-oksadiazol-2-il}-6-(etoksimetil)-5-(2-metoksifenil)piridin-2,4-diol,
N-({5-[6-butil-5-(2,3-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}metil)benzamid,
N-({5-[6-(etoksimetil)-2,4-dihidroksi-5-(2-metoksifenil)piridin-3-il]-1,3,4-oksadiazol-2-il}metil)benzamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(piridin-3-il)acetamid,
2-{5-[5-(2,6-dimetoksifenil)-6-(etoksimetil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(1,3-tiazol-2-il)acetamid,
N-[(1,3-benzotiazol-2-il)metil]-2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(piridin-3-il)metil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(1,3-oksazol-2-il)metil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[2-(4-sulfamoilfenil)etil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[2-(2-klorofenil)etil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(3-klorofenil)metil]acetamid,
N-benzil-2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-metilacetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-metil-N-(2-feniletil)acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(prop-2-in-1-il)acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-(3-metil-1H-pirazol-5-il)acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(2-metilfenil)metil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(2-klorofenil)metil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(4-klorofenil)metil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[2-(4-klorofenil)etil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(piridin-4-il)metil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(4-metoksifenil)metil]acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-{[4-(dimetilamino)fenil]metil}acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(5-metil-1,3,4-oksadiazol-2-il)metil]acetamid,271
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-{[3-(propan-2-il)-1,2-oksazol-5-il]metil}acetamid,
2-{5-[6-butil-5-(2,6-dimetoksifenil)-2,4-dihidroksipiridin-3-il]-1,3,4-oksadiazol-2-il}-N-[(4-sulfamoilfenil)metil]acetamid,
3-{5-[(5-kloropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}-6-(etoksimetil)-5-(2-hidroksi-6-metoksifenil)piridin-2,4-diol,
3-{5-[(5-kloropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}-6-(etoksimetil)-5-(2-hidroksi-6-metoksifenil)piridin-2,4-diol, i
3-{5-[(5-kloropiridin-2-il)metil]-1,3,4-oksadiazol-2-il}-5-(2,6-dihidroksifenil)-6-(etoksimetil)piridin-2,4-diol.
12. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
13. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
14. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
15. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
16. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
17. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
18. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
19. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
20. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
21. Spoj u skladu sa patentnim zahtjevom 1 koje ima strukturu:
ili njegova farmaceutski prihvatljiva sol.
22. Farmaceutska kompozicija, koja sadrži farmaceutski prihvatljiv nosač i spoj iz bilo kojeg od patentnih zahtjeva 1-21, ili njegov stereoizomer, tautomer, ili farmaceutski prihvatljivu sol.
23. Spojevi u skladu sa bilo kojim od patentnih zahtjeva 1 do 21 ili kompozicija u skladu sa patentnim zahtjevom 22 za primjenu u terapiji.
24. Spojevi u skladu sa bilo kojim od patentnih zahtjeva 1 do 21 ili kompozicija u skladu sa patentnim zahtjevom 22 za primjenu u liječenju kardiovaskularnih bolesti.
25. Spojevi ili kompozicija za primjenu u skladu sa patentnim zahtjevom 24 pri čemu spomenute kardiovaskularne bolesti su koronarna bolest srca, moždani udar, insuficijencija srca, sistolna insuficijencija srca, dijastolna insuficijencija srca, dijabetička insuficijencija srca, insuficijencija srca sa očuvanom ejektivnom frakcijom, kardiomiopatija, infarkt miokarda, lijeva ventrikularna disfunkcija, lijeva ventrikularna disfunkcija nakon infarkta miokarda, kardijalna hipertrofija, miokardijalno remodeliranje, miokardijalno remodeliranje nakon infarkta ili nakon operacije srca i valvularne bolesti srca.
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