HRP20170787T1 - Piridon amidi kao modulatori natrijevih kanala - Google Patents
Piridon amidi kao modulatori natrijevih kanala Download PDFInfo
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- HRP20170787T1 HRP20170787T1 HRP20170787TT HRP20170787T HRP20170787T1 HR P20170787 T1 HRP20170787 T1 HR P20170787T1 HR P20170787T T HRP20170787T T HR P20170787TT HR P20170787 T HRP20170787 T HR P20170787T HR P20170787 T1 HRP20170787 T1 HR P20170787T1
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- dihydropyridin
- oxo
- benzamide
- trifluoromethyl
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- 108010052164 Sodium Channels Proteins 0.000 title claims 3
- 102000018674 Sodium Channels Human genes 0.000 title claims 3
- -1 Pyridone amides Chemical class 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims 45
- 150000002367 halogens Chemical class 0.000 claims 45
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 36
- 150000003839 salts Chemical class 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 20
- 208000002193 Pain Diseases 0.000 claims 13
- 208000004296 neuralgia Diseases 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 3
- XNAAGHKLQDFJAV-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(1,1,2,2,2-pentafluoroethyl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(C(F)(F)C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 XNAAGHKLQDFJAV-UHFFFAOYSA-N 0.000 claims 2
- YXHMFJXQQXHKRO-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 YXHMFJXQQXHKRO-UHFFFAOYSA-N 0.000 claims 2
- SXHSUVHECGYYMY-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 SXHSUVHECGYYMY-UHFFFAOYSA-N 0.000 claims 2
- URUKPZGNTWPRGW-UHFFFAOYSA-N 2-(4-fluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=CC(F)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 URUKPZGNTWPRGW-UHFFFAOYSA-N 0.000 claims 2
- CSKLRKQUNQCFCW-UHFFFAOYSA-N 4,5-dichloro-2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(Cl)=C(Cl)C=C1C(=O)NC1=CC(=O)NC=C1 CSKLRKQUNQCFCW-UHFFFAOYSA-N 0.000 claims 2
- FZRXMWNNMIDCAX-UHFFFAOYSA-N 4-chloro-2-(4-fluoro-2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC(Cl)=CC=C1C(=O)NC1=CC(=O)NC=C1 FZRXMWNNMIDCAX-UHFFFAOYSA-N 0.000 claims 2
- 208000004998 Abdominal Pain Diseases 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims 2
- 208000005890 Neuroma Diseases 0.000 claims 2
- 206010034620 Peripheral sensory neuropathy Diseases 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 201000005572 sensory peripheral neuropathy Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- IXFWXFPSQUGQID-UHFFFAOYSA-N 2-(2,3-difluoro-4-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound FC1=C(F)C(C)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 IXFWXFPSQUGQID-UHFFFAOYSA-N 0.000 claims 1
- FPKSPIQOEJACSE-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4,6-bis(trifluoromethyl)benzamide Chemical compound FC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC(=O)NC=C1 FPKSPIQOEJACSE-UHFFFAOYSA-N 0.000 claims 1
- JLOCNBNTRGBNSU-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound FC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 JLOCNBNTRGBNSU-UHFFFAOYSA-N 0.000 claims 1
- UMDJUPAXVBHNKS-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethoxy)benzamide Chemical compound FC1=CC(F)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 UMDJUPAXVBHNKS-UHFFFAOYSA-N 0.000 claims 1
- UFVVLUUDTNDRGT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound FC1=CC(F)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 UFVVLUUDTNDRGT-UHFFFAOYSA-N 0.000 claims 1
- IZWSTOWJMYCSFT-UHFFFAOYSA-N 2-(2,6-difluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethoxy)benzamide Chemical compound FC1=CC=CC(F)=C1OC1=CC=C(OC(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 IZWSTOWJMYCSFT-UHFFFAOYSA-N 0.000 claims 1
- KREVBSDXGCKOJM-UHFFFAOYSA-N 2-(2,6-difluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound FC1=CC=CC(F)=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 KREVBSDXGCKOJM-UHFFFAOYSA-N 0.000 claims 1
- SUDPZTYFJSTPQI-UHFFFAOYSA-N 2-(2-chloro-3-fluoro-4-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound ClC1=C(F)C(OC)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 SUDPZTYFJSTPQI-UHFFFAOYSA-N 0.000 claims 1
- XENPFDQDTNUZPA-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound ClC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 XENPFDQDTNUZPA-UHFFFAOYSA-N 0.000 claims 1
- IJLRJKVKJNUIJD-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethoxy)benzamide Chemical compound ClC1=CC(F)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 IJLRJKVKJNUIJD-UHFFFAOYSA-N 0.000 claims 1
- BVWMEUDWRCWKGL-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound ClC1=CC(F)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 BVWMEUDWRCWKGL-UHFFFAOYSA-N 0.000 claims 1
- CGHVTPLFSBFCMC-UHFFFAOYSA-N 2-(2-chloro-4-methoxyphenoxy)-5-fluoro-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound ClC1=CC(OC)=CC=C1OC1=CC=C(F)C=C1C(=O)NC1=CC(=O)NC=C1 CGHVTPLFSBFCMC-UHFFFAOYSA-N 0.000 claims 1
- JNNYSEIQBAVVNL-UHFFFAOYSA-N 2-(2-chloro-4-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound ClC1=CC(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 JNNYSEIQBAVVNL-UHFFFAOYSA-N 0.000 claims 1
- CBWXHMITTMOYOY-UHFFFAOYSA-N 2-(2-chlorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=CNC(=O)C=C1NC(=O)C1=CC(C(F)(F)F)=CC=C1OC1=CC=CC=C1Cl CBWXHMITTMOYOY-UHFFFAOYSA-N 0.000 claims 1
- XMZFDPKNGIFRLZ-UHFFFAOYSA-N 2-(2-ethoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound CCOC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 XMZFDPKNGIFRLZ-UHFFFAOYSA-N 0.000 claims 1
- GGKJOYYMGVWXAT-UHFFFAOYSA-N 2-(2-fluoro-4-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound FC1=CC(OC)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 GGKJOYYMGVWXAT-UHFFFAOYSA-N 0.000 claims 1
- ICZIAJCVIIUREC-UHFFFAOYSA-N 2-(2-fluoro-4-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound FC1=CC(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 ICZIAJCVIIUREC-UHFFFAOYSA-N 0.000 claims 1
- OMKAJNDPKOXDJE-UHFFFAOYSA-N 2-(2-fluoro-6-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound COC1=CC=CC(F)=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 OMKAJNDPKOXDJE-UHFFFAOYSA-N 0.000 claims 1
- YDRSKXBOYKSOJN-UHFFFAOYSA-N 2-(2-fluoro-6-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethoxy)benzamide Chemical compound CC1=CC=CC(F)=C1OC1=CC=C(OC(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 YDRSKXBOYKSOJN-UHFFFAOYSA-N 0.000 claims 1
- KUCYRCUGXDBLAO-UHFFFAOYSA-N 2-(2-methoxy-4-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound COC1=CC(C)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 KUCYRCUGXDBLAO-UHFFFAOYSA-N 0.000 claims 1
- FAHBRZBMNSAQQB-UHFFFAOYSA-N 2-(2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound CC1=CC=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 FAHBRZBMNSAQQB-UHFFFAOYSA-N 0.000 claims 1
- MASHRDPYQKFCAR-UHFFFAOYSA-N 2-(2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethoxy)benzamide Chemical compound CC1=CC=CC=C1OC1=CC=C(OC(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 MASHRDPYQKFCAR-UHFFFAOYSA-N 0.000 claims 1
- PIQAUSNVLROXMR-UHFFFAOYSA-N 2-(2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound CC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 PIQAUSNVLROXMR-UHFFFAOYSA-N 0.000 claims 1
- JUDYBFMPBKSTBB-UHFFFAOYSA-N 2-(2-methylpropoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound CC(C)COC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 JUDYBFMPBKSTBB-UHFFFAOYSA-N 0.000 claims 1
- AWWWPDPNSMZXCC-UHFFFAOYSA-N 2-(2-methylpropoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound CC(C)COC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 AWWWPDPNSMZXCC-UHFFFAOYSA-N 0.000 claims 1
- FNYNPPMOZIJFAC-UHFFFAOYSA-N 2-(2-methylpyridin-3-yl)oxy-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound CC1=NC=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 FNYNPPMOZIJFAC-UHFFFAOYSA-N 0.000 claims 1
- QULMOQQNFDJHJA-UHFFFAOYSA-N 2-(2-methylpyridin-3-yl)oxy-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethoxy)benzamide Chemical compound CC1=NC=CC=C1OC1=CC=C(OC(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 QULMOQQNFDJHJA-UHFFFAOYSA-N 0.000 claims 1
- XLUICCIIQQVLBW-UHFFFAOYSA-N 2-(2-methylpyridin-3-yl)oxy-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound CC1=NC=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 XLUICCIIQQVLBW-UHFFFAOYSA-N 0.000 claims 1
- REFSPUPAKCCVAD-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanyloxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound C1C(C2)CCC2C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC=1C=CNC(=O)C=1 REFSPUPAKCCVAD-UHFFFAOYSA-N 0.000 claims 1
- XLENMSSHHOXWHN-UHFFFAOYSA-N 2-(3-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound COC1=C(F)C=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 XLENMSSHHOXWHN-UHFFFAOYSA-N 0.000 claims 1
- XFYJZSKHXSPHJR-UHFFFAOYSA-N 2-(3-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound COC1=C(F)C=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 XFYJZSKHXSPHJR-UHFFFAOYSA-N 0.000 claims 1
- ZUFQSMFAKHTNSW-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(1,1,2,2,2-pentafluoroethyl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1OC1=CC(C(F)(F)C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 ZUFQSMFAKHTNSW-UHFFFAOYSA-N 0.000 claims 1
- GIJKDQHCVRCMIN-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 GIJKDQHCVRCMIN-UHFFFAOYSA-N 0.000 claims 1
- OFZBNADUYSHVNR-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 OFZBNADUYSHVNR-UHFFFAOYSA-N 0.000 claims 1
- GYDKJXLRYAYBAQ-UHFFFAOYSA-N 2-(3-fluoro-5-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound COC1=CC(F)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)C(=O)NC2=CC(=O)NC=C2)=C1 GYDKJXLRYAYBAQ-UHFFFAOYSA-N 0.000 claims 1
- KICOFBPOACPQPG-UHFFFAOYSA-N 2-(3-methylbutoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound CC(C)CCOC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 KICOFBPOACPQPG-UHFFFAOYSA-N 0.000 claims 1
- FWASJBQVSBHBNK-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound FC1=CC(Cl)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 FWASJBQVSBHBNK-UHFFFAOYSA-N 0.000 claims 1
- WSAJJTWYTKFRMU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(Cl)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 WSAJJTWYTKFRMU-UHFFFAOYSA-N 0.000 claims 1
- IVXWSJDIJWTMBP-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound C=1C=C(Cl)C=CC=1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC=1C=CNC(=O)C=1 IVXWSJDIJWTMBP-UHFFFAOYSA-N 0.000 claims 1
- AKDINRARGVIZNO-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=CNC(=O)C=C1NC(=O)C1=CC(C(F)(F)F)=CC=C1OC1=CC=C(Cl)C=C1 AKDINRARGVIZNO-UHFFFAOYSA-N 0.000 claims 1
- NCISSLADDFSKLN-UHFFFAOYSA-N 2-(4-cyanophenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=CNC(=O)C=C1NC(=O)C1=CC(C(F)(F)F)=CC=C1OC1=CC=C(C#N)C=C1 NCISSLADDFSKLN-UHFFFAOYSA-N 0.000 claims 1
- HPURRFIKNKVIFS-UHFFFAOYSA-N 2-(4-cyclopropylphenoxy)-5-fluoro-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound C1=CNC(=O)C=C1NC(=O)C1=CC(F)=CC=C1OC(C=C1)=CC=C1C1CC1 HPURRFIKNKVIFS-UHFFFAOYSA-N 0.000 claims 1
- LNRALXGEGPHUEQ-UHFFFAOYSA-N 2-(4-ethoxyphenoxy)-5-fluoro-n-(2-oxo-1h-pyridin-4-yl)benzamide Chemical compound C1=CC(OCC)=CC=C1OC1=CC=C(F)C=C1C(=O)NC1=CC(=O)NC=C1 LNRALXGEGPHUEQ-UHFFFAOYSA-N 0.000 claims 1
- OJJVDLJKYRQHKJ-UHFFFAOYSA-N 2-(4-ethoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=CC(OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 OJJVDLJKYRQHKJ-UHFFFAOYSA-N 0.000 claims 1
- OFJWZNKJBMVLPX-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4,6-bis(trifluoromethyl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC(=O)NC=C1 OFJWZNKJBMVLPX-UHFFFAOYSA-N 0.000 claims 1
- OZJSEVZVZWZBIT-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(trifluoromethyl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 OZJSEVZVZWZBIT-UHFFFAOYSA-N 0.000 claims 1
- GFDFBVYVIAOKEU-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethoxy)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 GFDFBVYVIAOKEU-UHFFFAOYSA-N 0.000 claims 1
- JKAMBBDGLZFTHQ-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound COC1=CC(F)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C(=O)NC1=CC(=O)NC=C1 JKAMBBDGLZFTHQ-UHFFFAOYSA-N 0.000 claims 1
- CEWKJGUDXOKCAF-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenoxy)-n-(2-methyl-6-oxo-1h-pyridin-4-yl)-5-(trifluoromethyl)benzamide Chemical compound O=C1NC(C)=CC(NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)OC=2C(=CC(F)=CC=2)C)=C1 CEWKJGUDXOKCAF-UHFFFAOYSA-N 0.000 claims 1
- OJGBGGHWKBSYTM-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4,6-bis(trifluoromethyl)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1C(=O)NC1=CC(=O)NC=C1 OJGBGGHWKBSYTM-UHFFFAOYSA-N 0.000 claims 1
- OGNHUCWKIBGDPU-UHFFFAOYSA-N 2-(4-fluoro-2-methylphenoxy)-n-(2-oxo-1h-pyridin-4-yl)-4-(1,1,2,2,2-pentafluoroethyl)benzamide Chemical compound CC1=CC(F)=CC=C1OC1=CC(C(F)(F)C(F)(F)F)=CC=C1C(=O)NC1=CC(=O)NC=C1 OGNHUCWKIBGDPU-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- 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
-
- 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
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
-
- 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
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Claims (15)
1. Spoj formule I ili I’
[image]
ili njegova farmaceutski prihvatljiva sol,
gdje neovisno u svakom slučaju:
G je
[image]
[image]
X je veza ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena, gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
RX je odsutan, H, ili C3-C8 cikloalifatski radikal, gdje do dvije nesusjedne CH2 jedinice navedenog C3-C8 cikloalifatskog radikala mogu biti zamijenjene s -O- i navedeni C3-C8 cikloalifatski radikal je supstituiran s 0-3 supstituenta odabrana između halogena i C1-C4 alkila;
R1 je H, halogen, CN, ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena i gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
R2 je H, halogen, CN, ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena, gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
R3 je H, halogen, CN, ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena, gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
R4 je H, halogen, CN, ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena, gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
R5 je H, halogen, CN, ili -X-RX;
R5’ je H, halogen, CN, ili -X-RX;
R6 je H, halogen, CN, ili -X-RX;
R6’ je H, halogen, CN, ili -X-RX;
R7 je H, halogen, CN, ili -X-RX;
R8 je halogen, ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena, gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
p je cijeli broj koji uključuje od 0 do 3 ; i
R9 je H, ili C1-C6 alkil gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-.
2. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da R3 je C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena, i/ili gdje R3 je t-butil, CF3 ili CF2CF3.
3. Spoj ili njegova farmaceutski prihvatljiva sol prema bilo kojem od zahtjeva 1 do 2, naznačen time da G je
[image]
gdje,
R5 je H, halogen, CN, ili -X-RX;
R5’ je H, halogen, CN, ili -X-RX;
R6 je H, halogen, CN, ili -X-RX;
R6’ je H, halogen, CN, ili -X-RX;
R7 je H, halogen, CN, ili -X-RX;
X je veza ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena i gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-; i
RX je odsutan, H, ili C3-C8 cikloalifatski radikal, gdje do dvije nesusjedne CH2 jedinice navedenog C3-C8 cikloalifatskog radikala mogu biti zamijenjene s -O- navedeni C3-C8 cikloalifatski radikal je supstituiran s 0-3 supstituenta odabrana između halogena i C1-C4 alkila, poželjno kada je G izabran od:
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4. Spoj ili njegova farmaceutski prihvatljiva sol prema bilo kojem od zahtjeva 1 do 2, naznačen time da G je:
[image]
i G je odabran od
[image]
[image]
ili gdje je -X-RX i-X-RX odabran od:
[image]
[image]
[image]
5. Spoj ili njegova farmaceutski prihvatljiva sol prema bilo kojem od zahtjeva 1 do 4, naznačen time da p je 0, i/ili gdje R9 je H.
6. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da spoj ili njegova farmaceutski prihvatljiva sol ima formulu I-F ili I’-F
[image]
ili njegova farmaceutski prihvatljiva sol,
gdje neovisno u svakom slučaju:
R3 je halogen, CN, ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena, gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
R5 je halogen, CN, ili -X-RX;
R7 je halogen, CN, ili -X-RX;
X je veza ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena i gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
RX je odsutan, H, ili C3-C8 cikloalifatski radikal, gdje do dvije nesusjedne CH2 jedinice navedenog C3-C8 cikloalifatskog radikala mogu biti zamijenjene s -O- i navedeni C3-C8 cikloalifatski radikal je supstituiran s 0-3 supstituenta odabrana između halogena i C1-C4 alkila;
R8 je halogen ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena i gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
p je cijeli broj koji uključuje od 0 do 3; i
R9 je H, ili C1-C6 alkil gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-.
7. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 6, naznačen time da R3 je C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena, i/ili gdje R3 je t-butil CF3 ili CF2CF3, i/ili gdje je prsten A odabran od:
[image]
[image]
[image]
i/ili gdje p je 0, i/ili gdje R9 je H.
8. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da spoj ili farmaceutski prihvatljiva sol ima formulu I-G ili I’-G
[image]
ili njegova farmaceutski prihvatljiva sol,
gdje neovisno u svakom slučaju:
R2 je halogen, CN, ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena i gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
R3 je halogen, CN, ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena i gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
R5 je halogen, CN, ili -X-RX;
R7 je halogen, CN, ili -X-RX;
X je veza ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena i gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
RX je odsutan, H, ili C3-C8 cikloalifatski radikal, gdje do dvije nesusjedne CH2 jedinice navedenog C3-C8 cikloalifatskog radikala mogu biti zamijenjene s -O- i navedeni C3-C8 cikloalifatski radikal je supstituiran s 0-3 supstituenta odabrana između halogena i C1-C4 alkila;
R8 je halogen ili C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena i gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-;
p je cijeli broj koji uključuje od 0 do 3; i
R9 je H, ili C1-C6 alkil gdje do dvije nesusjedne CH2 jedinice navedenog C1-C6 alkila mogu biti zamijenjene s -O-.
9. Spoj ili njegova farmaceutski prihvatljiva sol prema bilo kojem od zahtjeva 8, naznačen time da R2 je F, Cl, CN, CF3 ili OCF3, i/ili gdje R3 je C1-C6 alkil gdje je navedeni C1-C6 alkil supstituiran s 0-6 halogena, i/ili gdje R3 je t-butil CF3 ili CF2CF3, i/ili gdje je prsten A odabran od:
[image]
[image]
[image]
i/ili gdje je p 0, i/ili gdje je R9 H.
10. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da je spoj ili njegova farmaceutski prihvatljiva sol odabran iz skupine koju čine:
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2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(4-fluorofenoksi)-N-(6-okso-1,6-dihidropiridin-3-il)benzamid;
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2-(4-fluorofenoksi)-N-(6-okso-1,6-dihidropiridin-3-il)-5-(trifluorometil)benzamid;
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2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(4-fluorofenoksi)-N-(6-okso-1,6-dihidropiridin-3-il)-4-(trifluorometil)benzamid;
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2-(2,4-difluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(4-(2-metoksietoksi)fenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-fenoksi-4-(trifluorometil)benzamid;
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2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(o-toliloksi)-4-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(p-toliloksi)-4-(trifluorometil)benzamid;
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4-kloro-2-(2,4-difluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-kloro-2-(2-kloro-4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-kloro-2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-kloro-2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-kloro-2-(2-fluoro-6-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-kloro-2-(2-kloro-6-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-kloro-2-(2,6-difluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-kloro-2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-cijano-2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-cijano-2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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4-cijano-2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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2-(2,4-difluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(4-cijanofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(2,6-difluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(p-toliloksi)-5-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(o-toliloksi)-5-(trifluorometil)benzamid;
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2-(2-kloro-4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-fenoksi-5-(trifluorometil)benzamid;
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2-(2,4-difluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
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2-(2,6-difluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(p-toliloksi)-5-(trifluorometoksi)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(o-toliloksi)-5-(trifluorometoksi)benzamid;
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2-(2-kloro-4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
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2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
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2-(2-fluoro-6-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
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2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-fenoksi-5-(trifluorometoksi)benzamid;
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2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
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2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-6-(trifluorometil)benzamid;
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2-(4-etoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(2-etoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(2-metoksi-4-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(2-fluoro-6-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(2-kloro-4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(4-kloro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(4-kloro-2-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(5-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(4-propoksifenoksi)-5-(trifluorometil)benzamid;
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2-(3-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(2-fluoro-4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(5-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(3-fluoro-5-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(4-klorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(3-fluoro-4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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N-(6-kloro-2-okso-1,2-dihidropiridin-4-il)-2-(4-fluoro-2-metilfenoksi)-5-(trifluorometil)benzamid
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2-(4-fluoro-2-metilfenoksi)-N-(6-metil-2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(2-propoksifenoksi)-5-(trifluorometil)benzamid;
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2-(4-metoksi-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(2-izopropoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(2-klorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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5-kloro-2-(2-kloro-4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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5-kloro-2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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5-kloro-2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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5-kloro-2-(2,4-difluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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5-kloro-2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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5-kloro-2-(3-fluoro-4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(4-(trifluorometoksi)fenoksi)-5-(trifluorometil)benzamid;
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2-(4-(difluorometoksi)fenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)-2-(4-(trifluorometil)fenoksi)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(2-(trifluorometoksi)fenoksi)-5-(trifluorometil)benzamid;
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2-(2-(difluorometoksi)fenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
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2-(2-kloro-4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(4-klorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(4-(trifluorometoksi)fenoksi)-4-(trifluorometil)benzamid;
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N-(2-okso-1,2-dihidropiridin-4-il)-2-(2-(trifluorometoksi)fenoksi)-4-(trifluorometil)benzamid;
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2-(3-fluoro-4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(4-(difluorometoksi)fenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(2-(difluorometoksi)fenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(2-fluoro-4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(4-fluorofenoksi)-N-(1-(2-hidroksietil)-2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(4-fluoro-2-metilfenoksi)-N-(5-metil-2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(3-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
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2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(perfluoroetil)benzamid;
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2-(3-fluoro-4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(perfluoroetil)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)-2-(2,3,4-trifluorofenoksi)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)-2-(2,3,5-trimetilfenoksi)benzamid;
[image]
2-(2,3-difluoro-4-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)-2-(2,4,5-trimetilfenoksi)benzamid;
[image]
5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)-2-(2,3,5-trimetilfenoksi)benzamid;
[image]
5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)-2-fenoksibenzamid;
[image]
2-(4-ciklopropilfenoksi)-5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
2-(4-(terc-butoksi)fenoksi)-5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
2-(4-etoksifenoksi)-5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
5-fluoro-2-(4-izopropilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)-2-(4-propoksifenoksi)benzamid;
[image]
5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)-2-(4-(trifluorometoksi)fenoksi)benzamid;
[image]
5-fluoro-2-(4-(2-metoksietil)fenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
2-(2-kloro-4-metoksifenoksi)-5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
5-fluoro-2-(4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)-2-(2,4,5-trimetilfenoksi)benzamid;
[image]
2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
[image]
5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)-2-(4-(2,2,2-trifluoroetoksi)fenoksi)benzamid;
[image]
2-(4-(ciklopropilmetoksi)fenoksi)-5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
4-kloro-2-(2-kloro-4-fluorofenoksi)-5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
2-(2-kloro-3-fluoro-4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(perfluoroetil)benzamid;
[image]
2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(perfluoroetil)benzamid;
[image]
4,5-dikloro-2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
4,5-dikloro-2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
4,5-dikloro-2-(3-fluoro-4-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
2-(izopentiloksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-izobutoksi-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-((2R)-biciklo[2.2.1]heptan-2-iloksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-((1-metilciklopropil)metoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-(ciklopentilmetoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-2-((tetrahidrofuran-3-il)metoksi)-4-(trifluorometil)benzamid;
[image]
2-ciklobutoksi-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-2-(4,4,4-trifluorobutoksi)-4-(trifluorometil)benzamid;
[image]
2-((2,2-dimetilciklopropil)metoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-((1R,5S)-biciklo[3.1.0]heksan-3-iloksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-((2,2-difluorociklopropil)metoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-(biciklo[2.2.1]heptan-2-iloksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-(cikloheksiloksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
4-kloro-N-(2-okso-1,2-dihidropiridin-4-il)-2-(4,4,4-trifluorobutoksi)benzamid;
[image]
2-(ciklopentilmetoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
[image]
2-izobutoksi-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)-2-(3,3,3-trifluoropropoksi)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-2-(4,4,4-trifluorobutoksi)-5-(trifluorometil)benzamid;
[image]
2-((2,2-dimetilciklopropil)metoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
[image]
2-((1R,5S)-biciklo[3.1.0]heksan-3-iloksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
[image]
2-(ciklopentilmetoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
[image]
2-(cikloheksiloksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)-2-(3,3,3-trifluoropropoksi)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-2-(4,4,4-trifluorobutoksi)-5-(trifluorometoksi)benzamid;
[image]
2-((2,2-dimetilciklopropil)metoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
[image]
4-(terc-butil)-N-(2-okso-1,2-dihidropiridin-4-il)-2-((6-(trifluorometil)piridin-3-il)oksi)benzamid;
[image]
4-(terc-butil)-N-(6-okso-1,6-dihidropiridin-3-il)-2-((6-(trifluorometil)piridin-3-il)oksi)benzamid;
[image]
4-kloro-N-(2-okso-1,2-dihidropiridin-4-il)-2-((6-(trifluorometil)piridin-3-il)oksi)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)-2-((6-(trifluorometil)piridin-3-il)oksi)benzamid;
[image]
N-(6-okso-1,6-dihidropiridin-3-il)-4-(trifluorometil)-2-((6-(trifluorometil)piridin-3-il)oksi)benzamid;
[image]
2-((6-metilpiridin-3-il)oksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-((2-metilpiridin-3-il)oksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
4-(terc-butil)-N-(1-metil-2-okso-1,2-dihidropiridin-4-il)-2-((6-(trifluorometil)piridin-3-il)oksi)benzamid;
[image]
4-(terc-butil)-N-(1-metil-6-okso-1,6-dihidropiridin-3-il)-2-((6-(trifluorometil)piridin-3-il)oksi)benzamid;
[image]
2-((2-metilpiridin-3-il)oksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
[image]
2-((2-metilpiridin-3-il)oksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometoksi)benzamid;
[image]
2-(2,4-difluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4,6-bis(trifluorometil)benzamid;
[image]
2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4,6-bis(trifluorometil)benzamid;
[image]
2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4,6-bis(trifluorometil)benzamid;
[image]
2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4,6-bis(trifluorometil)benzamid;
[image]
N-(2-okso-1,2-dihidropiridin-4-il)-2-fenoksi-4,6-bis(trifluorometil)benzamid;
[image]
2-(4-fluoro-2-(hidroksimetil)fenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-((5-fluoro-2-hidroksibenzil)oksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid; i
[image]
5-fluoro-N-(2-okso-1,2-dihidropiridin-4-il)-2-(4-(4,4,4-trifluorobutoksi)fenoksi)benzamid;
ili njihova farmaceutski prihvatljiva sol.
11. Spoj ili farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da je spoj ili farmaceutski prihvatljiva sol odabran iz skupine koju čine:
[image]
2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(trifluorometil)benzamid;
[image]
2-(4-fluorofenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-5-(trifluorometil)benzamid;
[image]
4-kloro-2-(4-fluoro-2-metilfenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid;
[image]
2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)-4-(perfluoroetil)benzamid; i
[image]
4,5-dikloro-2-(4-fluoro-2-metoksifenoksi)-N-(2-okso-1,2-dihidropiridin-4-il)benzamid, ili njihova farmaceutski prihvatljiva sol.
12. Farmaceutski pripravak naznačen time da sadrži terapeutski učinkovitu količinu spoja ili njegove farmaceutski prihvatljive soli prema bilo kojem od zahtjeva 1 do 11 i jedan ili više farmaceutski prihvatljivih nosača ili sredstava.
13. Spoj ili njegova farmaceutski prihvatljiva sol prema bilo kojem od zahtjeva 1 do 11 ili farmaceutski pripravak prema zahtjevu 12 naznačen time da je za upotrebu u postupku inhibicije naponski ovisnih natrijevih kanala kod subjekta, poželjno gdje je naponsko ovisan natrijev kanal Nav1.8.
14. Spoj ili njegova farmaceutski prihvatljiva prema bilo kojem od zahtjeva 1 do 11 ili farmaceutski prihvatljiv pripravak prema bilo kojem od zahtjeva 12 naznačen time da je za upotrebu u postupku za liječenje ili ublažavanje kod subjekta ozbiljnosti stanja kronične boli, boli u trbuhu, neuropatske boli, mišićno-skeletne boli, akutne boli, upalne boli, boli zbog karcinoma, idiopatske boli, multiple skleroze, sindroma Charcot-Marie-Tooth, inkontinencije ili srčane aritmije, poželjno pri čemu bol u trbuhu obuhvaća bol zbog upalne bolesti crijeva, Crohnove bolesti ili bol zbog intersticijskog cistitisa, ili pri čemu neuropatska bol obuhvaća postherpetičku neuralgiju, dijabetičku neuralgiju, bolnu HIV-povezanu senzornu neuropatiju, trigeminalnu neuralgiju, sindrom pečenja u ustima, bol poslije amputacije, fantomsku bol, bolni neurom; traumatski neurom; Mortonov neurom; ozljede uklještenja živca, spinalnu stenozu, sindrom karpalnog tunela, radikularnu bol, išijas; avulziju živca, nasilno odvajanje brahijalnog pleksusa; kompleksni regionalni bolni sindrom, neuralgiju uzrokovanu terapijom lijekovima, neuralgiju izazvanu kemoterapijom raka, neuralgiju izazvanu anti-retroviralnom terapijom; bol poslije ozljeda leđne moždine, idiopatsku neuropatiju kratkih vlakana, idiopatsku senzornu neuropatiju ili trigeminalnu autonomnu cefalalgiju, ili gdje mišićno-skeltna bol obuhvaća bol zbog osteoartritisa, bol u leđima, bol zbog hladnoće, bol zbog opeklina ili zubobolju, ili gdje upalna bola obuhvaća bol zbog reumatoidnog artritisa ili vulvodiniju, ili gdje idiopatska bol obuhvaća bol zbog fibromialgije.
15. Spoj ili farmaceutski prihvatljiva sol ili farmaceutski pripravak za upotrebu prema bilo kojem od patentnih zahtjeva 13 do 14, naznačen time da se navedeni subjekt liječi s jednim ili više dodatnih terapeutskih sredstava koja se daju istovremeno, prije ili poslije liječenja sa spojem ili farmaceutski prihvatljivom soli ili farmaceutskim pripravkom.
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