JP2013543480A5 - - Google Patents
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- JP2013543480A5 JP2013543480A5 JP2013517495A JP2013517495A JP2013543480A5 JP 2013543480 A5 JP2013543480 A5 JP 2013543480A5 JP 2013517495 A JP2013517495 A JP 2013517495A JP 2013517495 A JP2013517495 A JP 2013517495A JP 2013543480 A5 JP2013543480 A5 JP 2013543480A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- isonicotinamide
- pyridin
- ethyl
- trifluoroethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 315
- -1 4-pyrimidyl Chemical group 0.000 claims 263
- 229940080818 propionamide Drugs 0.000 claims 107
- 229940047889 isobutyramide Drugs 0.000 claims 70
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 68
- 125000001424 substituent group Chemical group 0.000 claims 45
- 125000000217 alkyl group Chemical group 0.000 claims 42
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 31
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 239000000126 substance Substances 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- IQHHPMNFYJGULP-UHFFFAOYSA-N 1,3-benzoxazole-7-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1OC=N2 IQHHPMNFYJGULP-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 230000001419 dependent effect Effects 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
- HOLYRSULJLIUBJ-UHFFFAOYSA-N 2-acetamido-n-[1-[6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1N=C(OCC(F)F)C(C)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 HOLYRSULJLIUBJ-UHFFFAOYSA-N 0.000 claims 2
- DXTQJPSLYPOCKO-UHFFFAOYSA-N 2-acetamido-n-[[2-methoxy-4-(trifluoromethoxy)phenyl]methyl]-6-methylpyridine-4-carboxamide Chemical compound COC1=CC(OC(F)(F)F)=CC=C1CNC(=O)C1=CC(C)=NC(NC(C)=O)=C1 DXTQJPSLYPOCKO-UHFFFAOYSA-N 0.000 claims 2
- HIXIZSPXSAQXDG-UHFFFAOYSA-N 2-acetamido-n-[[6-(2,2-difluoroethoxy)-4-methylpyridin-3-yl]methyl]-6-methylpyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C)=CC(C(=O)NCC=2C(=CC(OCC(F)F)=NC=2)C)=C1 HIXIZSPXSAQXDG-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- MFNYBOWJWGPXFM-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1CCC1 MFNYBOWJWGPXFM-UHFFFAOYSA-N 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- NCOBOYCDOCJDJT-UHFFFAOYSA-N n-[1-[5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]-2-methyl-6-(propanoylamino)pyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)CC)=CC(C(=O)NC(C)C=2C=C(F)C(OCC(F)(F)F)=NC=2)=C1 NCOBOYCDOCJDJT-UHFFFAOYSA-N 0.000 claims 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
- OOXOXZVOZIURRD-UHFFFAOYSA-N pyridine-2,4-dicarboxamide Chemical compound NC(=O)C1=CC=NC(C(N)=O)=C1 OOXOXZVOZIURRD-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- INJSSRINBKEZSM-UHFFFAOYSA-N 1-methyl-5-phenyl-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrazole-3-carboxamide Chemical compound C=1C=C(OCC(F)(F)F)N=CC=1C(C)NC(=O)C(=NN1C)C=C1C1=CC=CC=C1 INJSSRINBKEZSM-UHFFFAOYSA-N 0.000 claims 1
- FIVAIHFPDYPLRM-UHFFFAOYSA-N 1-methyl-n-[1-[5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrazolo[3,4-b]pyridine-3-carboxamide Chemical compound N=1N(C)C2=NC=CC=C2C=1C(=O)NC(C)C1=CN=C(OCC(F)(F)F)C(C)=C1 FIVAIHFPDYPLRM-UHFFFAOYSA-N 0.000 claims 1
- UGPTWDIHWGAOHN-UHFFFAOYSA-N 1-methyl-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-2-yl]ethyl]indazole-3-carboxamide Chemical compound N=1N(C)C2=CC=CC=C2C=1C(=O)NC(C)C1=CC=CC(OCC(F)(F)F)=N1 UGPTWDIHWGAOHN-UHFFFAOYSA-N 0.000 claims 1
- MANVTQZFBIXWMI-UHFFFAOYSA-N 1-methyl-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]indazole-3-carboxamide Chemical compound N=1N(C)C2=CC=CC=C2C=1C(=O)NC(C)C1=CC=C(OCC(F)(F)F)N=C1 MANVTQZFBIXWMI-UHFFFAOYSA-N 0.000 claims 1
- RHQPLLKOZOZWGT-UHFFFAOYSA-N 1-methyl-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrazolo[3,4-b]pyridine-3-carboxamide Chemical compound N=1N(C)C2=NC=CC=C2C=1C(=O)NC(C)C1=CC=C(OCC(F)(F)F)N=C1 RHQPLLKOZOZWGT-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- AHHRHTQQPOCDJR-UHFFFAOYSA-N 2-(2,2-dimethylpropanoylamino)-n-[1-[5-methyl-6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-yl]ethyl]pyridine-4-carboxamide Chemical compound C=1N=C(OCC(F)(F)C(F)F)C(C)=CC=1C(C)NC(=O)C1=CC=NC(NC(=O)C(C)(C)C)=C1 AHHRHTQQPOCDJR-UHFFFAOYSA-N 0.000 claims 1
- PEOCHZRVCQEOBB-UHFFFAOYSA-N 2-(2,2-dimethylpropanoylamino)-n-[[4-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyridine-4-carboxamide Chemical compound CC1=CC(OCC(F)(F)F)=NC=C1CNC(=O)C1=CC=NC(NC(=O)C(C)(C)C)=C1 PEOCHZRVCQEOBB-UHFFFAOYSA-N 0.000 claims 1
- ACRZFMPVUVJGGV-UHFFFAOYSA-N 2-(2,2-dimethylpropanoylamino)-n-[[6-(2,2,3,3,3-pentafluoropropoxy)pyridin-3-yl]methyl]pyridine-4-carboxamide Chemical compound C1=NC(NC(=O)C(C)(C)C)=CC(C(=O)NCC=2C=NC(OCC(F)(F)C(F)(F)F)=CC=2)=C1 ACRZFMPVUVJGGV-UHFFFAOYSA-N 0.000 claims 1
- KYEHQQBTDBVWJQ-UHFFFAOYSA-N 2-(dimethylamino)-6-methyl-n-[1-[5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1N=C(OCC(F)(F)F)C(C)=CC=1C(C)NC(=O)C1=CC(C)=NC(N(C)C)=N1 KYEHQQBTDBVWJQ-UHFFFAOYSA-N 0.000 claims 1
- DAGDJCQXLQFQEW-UHFFFAOYSA-N 2-[(3,4-dimethyl-1,2-oxazol-5-yl)amino]-6-methyl-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1C=C(OCC(F)(F)F)N=CC=1C(C)NC(=O)C(N=1)=CC(C)=NC=1NC=1ON=C(C)C=1C DAGDJCQXLQFQEW-UHFFFAOYSA-N 0.000 claims 1
- BGHYCGMZWGJKMX-UHFFFAOYSA-N 2-acetamido-6-methyl-n-[1-[3-(2,2,2-trifluoroethoxy)phenyl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1C=CC(OCC(F)(F)F)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=N1 BGHYCGMZWGJKMX-UHFFFAOYSA-N 0.000 claims 1
- LLDOBQHXYQYLHN-UHFFFAOYSA-N 2-acetamido-6-methyl-n-[1-[3-(trifluoromethoxy)phenyl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1C=CC(OC(F)(F)F)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=N1 LLDOBQHXYQYLHN-UHFFFAOYSA-N 0.000 claims 1
- VJQWFPSQWIIRQD-UHFFFAOYSA-N 2-acetamido-6-methyl-n-[1-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1C=C(OCC(F)(F)F)C=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=N1 VJQWFPSQWIIRQD-UHFFFAOYSA-N 0.000 claims 1
- PXXJBTVZVYSDMY-UHFFFAOYSA-N 2-acetamido-6-methyl-n-[1-[5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1N=C(OCC(F)(F)F)C(C)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=N1 PXXJBTVZVYSDMY-UHFFFAOYSA-N 0.000 claims 1
- XXDJLUNHOLXVEO-UHFFFAOYSA-N 2-acetamido-6-methyl-n-[1-[6-(3,3,3-trifluoropropoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1C=C(OCCC(F)(F)F)N=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=N1 XXDJLUNHOLXVEO-UHFFFAOYSA-N 0.000 claims 1
- FNLXIWIRCOIDQR-UHFFFAOYSA-N 2-acetamido-6-methyl-n-[[2-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyrimidine-4-carboxamide Chemical compound CC(=O)NC1=NC(C)=CC(C(=O)NCC=2C(=NC(OCC(F)(F)F)=CC=2)C)=N1 FNLXIWIRCOIDQR-UHFFFAOYSA-N 0.000 claims 1
- ADGMEVULYVVNDM-UHFFFAOYSA-N 2-acetamido-6-methyl-n-[[4-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyrimidine-4-carboxamide Chemical compound CC(=O)NC1=NC(C)=CC(C(=O)NCC=2C(=CC(OCC(F)(F)F)=NC=2)C)=N1 ADGMEVULYVVNDM-UHFFFAOYSA-N 0.000 claims 1
- HPRFODJNJUYTJN-UHFFFAOYSA-N 2-acetamido-6-methyl-n-[[5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyrimidine-4-carboxamide Chemical compound CC(=O)NC1=NC(C)=CC(C(=O)NCC=2C=C(C)C(OCC(F)(F)F)=NC=2)=N1 HPRFODJNJUYTJN-UHFFFAOYSA-N 0.000 claims 1
- AXWKFEURYSVDDM-UHFFFAOYSA-N 2-acetamido-6-methyl-n-[[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyrimidine-4-carboxamide Chemical compound CC(=O)NC1=NC(C)=CC(C(=O)NCC=2C=NC(OCC(F)(F)F)=CC=2)=N1 AXWKFEURYSVDDM-UHFFFAOYSA-N 0.000 claims 1
- SOIBOXBEEUCRTQ-UHFFFAOYSA-N 2-acetamido-n-[1-[2-chloro-4-(2,2,2-trifluoroethoxy)phenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C=C(OCC(F)(F)F)C=C(Cl)C=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 SOIBOXBEEUCRTQ-UHFFFAOYSA-N 0.000 claims 1
- JDQDVCDRMMYOLB-UHFFFAOYSA-N 2-acetamido-n-[1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C(C(F)(F)F)=CC=C(F)C=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 JDQDVCDRMMYOLB-UHFFFAOYSA-N 0.000 claims 1
- OLQRJXAKNKJUTM-UHFFFAOYSA-N 2-acetamido-n-[1-[3-(2,2,2-trifluoroethoxy)phenyl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1C=CC(OCC(F)(F)F)=CC=1C(C)NC(=O)C1=CC=NC(NC(C)=O)=N1 OLQRJXAKNKJUTM-UHFFFAOYSA-N 0.000 claims 1
- ZHJHNASXLICFBY-UHFFFAOYSA-N 2-acetamido-n-[1-[3-(2,2-difluoroethoxy)-5-methylphenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C(C)=CC(OCC(F)F)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 ZHJHNASXLICFBY-UHFFFAOYSA-N 0.000 claims 1
- WNZBKLZGYWNPNB-UHFFFAOYSA-N 2-acetamido-n-[1-[3-(difluoromethyl)phenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C=CC(C(F)F)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 WNZBKLZGYWNPNB-UHFFFAOYSA-N 0.000 claims 1
- NLIPONGFRYGTPS-UHFFFAOYSA-N 2-acetamido-n-[1-[3-(trifluoromethoxy)phenyl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1C=CC(OC(F)(F)F)=CC=1C(C)NC(=O)C1=CC=NC(NC(C)=O)=N1 NLIPONGFRYGTPS-UHFFFAOYSA-N 0.000 claims 1
- KXTDFRBGMRMHQM-UHFFFAOYSA-N 2-acetamido-n-[1-[3-chloro-4-(2,2,2-trifluoroethoxy)phenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C=C(OCC(F)(F)F)C(Cl)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 KXTDFRBGMRMHQM-UHFFFAOYSA-N 0.000 claims 1
- VIOZBWFUUCQPSU-UHFFFAOYSA-N 2-acetamido-n-[1-[3-chloro-4-(2,2-difluoroethoxy)-5-methylphenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C(C)=C(OCC(F)F)C(Cl)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 VIOZBWFUUCQPSU-UHFFFAOYSA-N 0.000 claims 1
- AXGVPGYLYHRXEG-UHFFFAOYSA-N 2-acetamido-n-[1-[3-chloro-4-(2,2-difluoroethoxy)phenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C=C(OCC(F)F)C(Cl)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 AXGVPGYLYHRXEG-UHFFFAOYSA-N 0.000 claims 1
- PGNXIMPLTSLZBS-UHFFFAOYSA-N 2-acetamido-n-[1-[3-chloro-5-(trifluoromethoxy)phenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C(Cl)=CC(OC(F)(F)F)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 PGNXIMPLTSLZBS-UHFFFAOYSA-N 0.000 claims 1
- DBVUIXOULFYEHH-UHFFFAOYSA-N 2-acetamido-n-[1-[4-(2,2-difluoroethoxy)-2-methylphenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C=C(OCC(F)F)C=C(C)C=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 DBVUIXOULFYEHH-UHFFFAOYSA-N 0.000 claims 1
- KITRAUMZIQQAIM-UHFFFAOYSA-N 2-acetamido-n-[1-[4-(2,2-difluoroethoxy)-3,5-dimethylphenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C(C)=C(OCC(F)F)C(C)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 KITRAUMZIQQAIM-UHFFFAOYSA-N 0.000 claims 1
- AJHOYOHTKUXPMA-UHFFFAOYSA-N 2-acetamido-n-[1-[4-(2,2-difluoroethoxy)-3-methoxyphenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C1=C(OCC(F)F)C(OC)=CC(C(C)NC(=O)C=2C=C(NC(C)=O)N=C(C)C=2)=C1 AJHOYOHTKUXPMA-UHFFFAOYSA-N 0.000 claims 1
- ISBDIPZZVAQYSX-UHFFFAOYSA-N 2-acetamido-n-[1-[4-(2,2-difluoroethoxy)-3-methylphenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C=C(OCC(F)F)C(C)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 ISBDIPZZVAQYSX-UHFFFAOYSA-N 0.000 claims 1
- GQAZLQRJYZDZLW-UHFFFAOYSA-N 2-acetamido-n-[1-[5-(2,2-difluoroethoxy)-2-methylphenyl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C(OCC(F)F)=CC=C(C)C=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 GQAZLQRJYZDZLW-UHFFFAOYSA-N 0.000 claims 1
- FMMGWZSAAIYTPV-UHFFFAOYSA-N 2-acetamido-n-[1-[5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]-6-methylpyrimidine-4-carboxamide Chemical compound C=1N=C(OCC(F)(F)F)C(Cl)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=N1 FMMGWZSAAIYTPV-UHFFFAOYSA-N 0.000 claims 1
- OANTWWQKBPXWNK-UHFFFAOYSA-N 2-acetamido-n-[1-[5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1N=C(OCC(F)(F)F)C(Cl)=CC=1C(C)NC(=O)C1=CC=NC(NC(C)=O)=N1 OANTWWQKBPXWNK-UHFFFAOYSA-N 0.000 claims 1
- VAONOKJGEZWFFT-UHFFFAOYSA-N 2-acetamido-n-[1-[5-chloro-6-(2,2-difluoroethoxy)pyridin-3-yl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1N=C(OCC(F)F)C(Cl)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 VAONOKJGEZWFFT-UHFFFAOYSA-N 0.000 claims 1
- HJRWLXJJTMYLTB-UHFFFAOYSA-N 2-acetamido-n-[1-[5-cyclopropyl-6-(2,2-difluoroethoxy)pyridin-3-yl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1N=C(OCC(F)F)C(C2CC2)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 HJRWLXJJTMYLTB-UHFFFAOYSA-N 0.000 claims 1
- XLYMTOZJFHRNLB-UHFFFAOYSA-N 2-acetamido-n-[1-[5-ethoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound N1=C(OCC(F)(F)F)C(OCC)=CC(C(C)NC(=O)C=2C=C(NC(C)=O)N=C(C)C=2)=C1 XLYMTOZJFHRNLB-UHFFFAOYSA-N 0.000 claims 1
- WHRQBVTVCLBDPA-UHFFFAOYSA-N 2-acetamido-n-[1-[5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1N=C(OCC(F)(F)F)C(F)=CC=1C(C)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 WHRQBVTVCLBDPA-UHFFFAOYSA-N 0.000 claims 1
- SEZYORYEJJRYLK-UHFFFAOYSA-N 2-acetamido-n-[1-[5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]-n,6-dimethylpyridine-4-carboxamide Chemical compound C=1N=C(OCC(F)(F)F)C(F)=CC=1C(C)N(C)C(=O)C1=CC(C)=NC(NC(C)=O)=C1 SEZYORYEJJRYLK-UHFFFAOYSA-N 0.000 claims 1
- PTUOCJUPZVELNT-UHFFFAOYSA-N 2-acetamido-n-[1-[5-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound N1=C(OCC(F)(F)F)C(OC)=CC(C(C)NC(=O)C=2C=C(NC(C)=O)N=C(C)C=2)=C1 PTUOCJUPZVELNT-UHFFFAOYSA-N 0.000 claims 1
- MNSRJZFKYKWIKQ-UHFFFAOYSA-N 2-acetamido-n-[1-[5-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound N1=C(OCC(F)(F)F)C(OC)=CC(C(C)NC(=O)C=2N=C(NC(C)=O)N=CC=2)=C1 MNSRJZFKYKWIKQ-UHFFFAOYSA-N 0.000 claims 1
- KEPLRBQQUVELEZ-UHFFFAOYSA-N 2-acetamido-n-[1-[5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound C=1N=C(OCC(F)(F)F)C(C)=CC=1C(C)NC(=O)C1=CC=NC(NC(C)=O)=N1 KEPLRBQQUVELEZ-UHFFFAOYSA-N 0.000 claims 1
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- IOTIRYMCZIPPBB-UHFFFAOYSA-N 2-acetamido-n-[1-[6-(2,2-difluoroethoxy)-5-methoxypyridin-3-yl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound N1=C(OCC(F)F)C(OC)=CC(C(C)NC(=O)C=2C=C(NC(C)=O)N=C(C)C=2)=C1 IOTIRYMCZIPPBB-UHFFFAOYSA-N 0.000 claims 1
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- DZMAHSPHIGATQZ-UHFFFAOYSA-N 2-acetamido-n-[2-methoxy-1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C=1C=C(OCC(F)(F)F)N=CC=1C(COC)NC(=O)C1=CC(C)=NC(NC(C)=O)=C1 DZMAHSPHIGATQZ-UHFFFAOYSA-N 0.000 claims 1
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- NBBHFPMVXJAMKS-UHFFFAOYSA-N 2-acetamido-n-[[2-chloro-4-(2,2-difluoroethoxy)phenyl]methyl]-6-methylpyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C)=CC(C(=O)NCC=2C(=CC(OCC(F)F)=CC=2)Cl)=C1 NBBHFPMVXJAMKS-UHFFFAOYSA-N 0.000 claims 1
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- FDKOPVOXSWJLLF-UHFFFAOYSA-N 2-acetamido-n-[[2-fluoro-3-(trifluoromethoxy)phenyl]methyl]-6-methylpyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C)=CC(C(=O)NCC=2C(=C(OC(F)(F)F)C=CC=2)F)=C1 FDKOPVOXSWJLLF-UHFFFAOYSA-N 0.000 claims 1
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- HMPUIOILURXVKH-UHFFFAOYSA-N 2-acetamido-n-[[3-chloro-4-(trifluoromethoxy)phenyl]methyl]-6-methylpyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C)=CC(C(=O)NCC=2C=C(Cl)C(OC(F)(F)F)=CC=2)=C1 HMPUIOILURXVKH-UHFFFAOYSA-N 0.000 claims 1
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- QRPBBMILADPWNU-UHFFFAOYSA-N 2-acetamido-n-[[4-(2,2-difluoroethoxy)-3-methylphenyl]methyl]-6-methylpyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C)=CC(C(=O)NCC=2C=C(C)C(OCC(F)F)=CC=2)=C1 QRPBBMILADPWNU-UHFFFAOYSA-N 0.000 claims 1
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- BXEJYBUVJQZVBO-UHFFFAOYSA-N 2-acetamido-n-[[5-bromo-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyridine-4-carboxamide Chemical compound C1=NC(NC(=O)C)=CC(C(=O)NCC=2C=C(Br)C(OCC(F)(F)F)=NC=2)=C1 BXEJYBUVJQZVBO-UHFFFAOYSA-N 0.000 claims 1
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- QJCQROQSUHINCE-UHFFFAOYSA-N 2-acetamido-n-[[5-ethoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-6-methylpyridine-4-carboxamide Chemical compound N1=C(OCC(F)(F)F)C(OCC)=CC(CNC(=O)C=2C=C(NC(C)=O)N=C(C)C=2)=C1 QJCQROQSUHINCE-UHFFFAOYSA-N 0.000 claims 1
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- UJXWVPUJSVSGBR-UHFFFAOYSA-N 2-acetamido-n-[[5-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-6-methylpyrimidine-4-carboxamide Chemical compound N1=C(OCC(F)(F)F)C(OC)=CC(CNC(=O)C=2N=C(NC(C)=O)N=C(C)C=2)=C1 UJXWVPUJSVSGBR-UHFFFAOYSA-N 0.000 claims 1
- RPQUNTNHNCNDTM-UHFFFAOYSA-N 2-acetamido-n-[[5-phenyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyridine-4-carboxamide Chemical compound C1=NC(NC(=O)C)=CC(C(=O)NCC=2C=C(C(OCC(F)(F)F)=NC=2)C=2C=CC=CC=2)=C1 RPQUNTNHNCNDTM-UHFFFAOYSA-N 0.000 claims 1
- AFZXICXDNUASOQ-UHFFFAOYSA-N 2-acetamido-n-[[6-(2,2-difluoroethoxy)-2-methoxypyridin-3-yl]methyl]-6-methylpyridine-4-carboxamide Chemical compound COC1=NC(OCC(F)F)=CC=C1CNC(=O)C1=CC(C)=NC(NC(C)=O)=C1 AFZXICXDNUASOQ-UHFFFAOYSA-N 0.000 claims 1
- FRFYZPJQZQFBJC-UHFFFAOYSA-N 2-acetamido-n-[[6-(2,2-difluoroethoxy)-2-methylpyridin-3-yl]methyl]-6-methylpyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C)=CC(C(=O)NCC=2C(=NC(OCC(F)F)=CC=2)C)=C1 FRFYZPJQZQFBJC-UHFFFAOYSA-N 0.000 claims 1
- WELPBOILZRJVKI-UHFFFAOYSA-N 2-acetamido-n-[[6-(2,2-difluoroethoxy)-5-ethylpyridin-3-yl]methyl]-6-methylpyridine-4-carboxamide Chemical compound N1=C(OCC(F)F)C(CC)=CC(CNC(=O)C=2C=C(NC(C)=O)N=C(C)C=2)=C1 WELPBOILZRJVKI-UHFFFAOYSA-N 0.000 claims 1
- PZEMPVPKCSXBSS-UHFFFAOYSA-N 2-acetamido-n-[[6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl]methyl]-6-methylpyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C)=CC(C(=O)NCC=2C=C(C)C(OCC(F)F)=NC=2)=C1 PZEMPVPKCSXBSS-UHFFFAOYSA-N 0.000 claims 1
- VAPZXOFBRBFCIW-UHFFFAOYSA-N 2-acetamido-n-[[6-(2,2-difluoropropoxy)pyridin-3-yl]methyl]-6-methylpyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C)=CC(C(=O)NCC=2C=NC(OCC(C)(F)F)=CC=2)=C1 VAPZXOFBRBFCIW-UHFFFAOYSA-N 0.000 claims 1
- KRWRIVIXKZQODN-UHFFFAOYSA-N 2-amino-6-methyl-n-[[5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyrimidine-4-carboxamide Chemical compound NC1=NC(C)=CC(C(=O)NCC=2C=C(C)C(OCC(F)(F)F)=NC=2)=N1 KRWRIVIXKZQODN-UHFFFAOYSA-N 0.000 claims 1
- VQYURJPBCHJTSM-UHFFFAOYSA-N 2-ethoxy-6-methyl-n-[1-[5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound CCOC1=NC(C)=CC(C(=O)NC(C)C=2C=C(C)C(OCC(F)(F)F)=NC=2)=N1 VQYURJPBCHJTSM-UHFFFAOYSA-N 0.000 claims 1
- GWISADLPXFQJDP-UHFFFAOYSA-N 2-methoxy-6-methyl-n-[1-[5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound COC1=NC(C)=CC(C(=O)NC(C)C=2C=C(C)C(OCC(F)(F)F)=NC=2)=N1 GWISADLPXFQJDP-UHFFFAOYSA-N 0.000 claims 1
- UCGAPOIGQFWVIV-UHFFFAOYSA-N 2-methyl-6-(1,3-thiazol-2-yl)-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyridine-4-carboxamide Chemical compound C=1C=C(OCC(F)(F)F)N=CC=1C(C)NC(=O)C(C=1)=CC(C)=NC=1C1=NC=CS1 UCGAPOIGQFWVIV-UHFFFAOYSA-N 0.000 claims 1
- IZDHWQRGYWFJBD-UHFFFAOYSA-N 2-methyl-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]-1h-benzimidazole-4-carboxamide Chemical compound C=1C=CC=2NC(C)=NC=2C=1C(=O)NC(C)C1=CC=C(OCC(F)(F)F)N=C1 IZDHWQRGYWFJBD-UHFFFAOYSA-N 0.000 claims 1
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- IDBYYDGKHQRBOA-UHFFFAOYSA-N n-[[5-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-2-methyl-6-(propanoylamino)pyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)CC)=CC(C(=O)NCC=2C=C(OC)C(OCC(F)(F)F)=NC=2)=C1 IDBYYDGKHQRBOA-UHFFFAOYSA-N 0.000 claims 1
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- CFWSSYOKWPXVGU-UHFFFAOYSA-N n-[[6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl]methyl]-2-methyl-6-(propanoylamino)pyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)CC)=CC(C(=O)NCC=2C=C(C)C(OCC(F)F)=NC=2)=C1 CFWSSYOKWPXVGU-UHFFFAOYSA-N 0.000 claims 1
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| PCT/JP2011/005802 WO2012053186A1 (en) | 2010-10-18 | 2011-10-18 | Arylamide derivatives as ttx-s blockers |
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| IN2014MN01982A (https=) * | 2012-04-25 | 2015-07-10 | Raqualia Pharma Inc | |
| KR102090944B1 (ko) * | 2012-04-25 | 2020-03-19 | 라퀄리아 파마 인코포레이티드 | Ttx-s 차단제로서의 피롤로피리디논 유도체 |
| EP2914597B1 (en) * | 2012-10-31 | 2017-12-06 | RaQualia Pharma Inc | Pyrazolopyridine derivatives as ttx-s blockers |
| EP3102569A1 (en) * | 2014-02-06 | 2016-12-14 | AbbVie Inc. | 6-heteroaryloxy- and 6-aryloxy-quinoline-2-carboxamides and uses thereof |
| EP3359151A4 (en) * | 2015-10-07 | 2019-08-14 | Arizona Board of Regents on behalf of the University of Arizona | CRMP2 SUMOYLATION INHIBITORS AND USES THEREOF |
| TWI773657B (zh) | 2015-12-18 | 2022-08-11 | 美商亞德利克斯公司 | 作爲非全身ｔｇｒ５促效劑之經取代之4-苯基吡啶化合物 |
| US12084472B2 (en) | 2015-12-18 | 2024-09-10 | Ardelyx, Inc. | Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists |
| AU2016379292B2 (en) * | 2015-12-24 | 2021-03-25 | Kyowa Kirin Co., Ltd. | α, β unsaturated amide compound |
| CN106083813A (zh) * | 2016-06-13 | 2016-11-09 | 太原理工大学 | 一种三唑‑喹啉类化合物的合成方法 |
| EP3558992A4 (en) | 2016-12-15 | 2020-12-02 | ONO Pharmaceutical Co., Ltd. | TREK CHANNEL ACTIVATOR (K + CHANNELS ASSOCIATED WITH TWIK) |
| EP3601255A1 (en) | 2017-03-21 | 2020-02-05 | AbbVie Deutschland GmbH & Co. KG | Proline amide compounds and their azetidine analogues carrying a specifically substituted benzyl radical |
| PT3487839T (pt) | 2017-06-20 | 2021-02-11 | Raqualia Pharma Inc | Derivados de amida como bloqueadores de nav1.7 e nav1.8 |
| WO2019045035A1 (en) * | 2017-08-31 | 2019-03-07 | Raqualia Pharma Inc. | BIARYLOXY DERIVATIVES AS TTX-S BLOCKERS |
| MX2020011275A (es) | 2018-04-25 | 2020-11-13 | Bayer Ag | Novedosos compuestos de heteroaril-triazol y hetroaril[-]tetrazol como plaguicidas. |
| RU2761824C2 (ru) * | 2018-08-03 | 2021-12-13 | Закрытое Акционерное Общество "Биокад" | Ингибиторы CDK8/19 |
| EP3873893A1 (en) * | 2018-11-02 | 2021-09-08 | Merck Sharp & Dohme Corp. | 2-amino-n-heteroaryl-nicotinamides as nav1.8 inhibitors |
| WO2020179859A1 (ja) | 2019-03-06 | 2020-09-10 | 第一三共株式会社 | ピロロピラゾール誘導体 |
| AR119009A1 (es) * | 2019-05-29 | 2021-11-17 | Syngenta Crop Protection Ag | Derivados de alcoxipiridina y alcoxipirimidina microbicidas |
| GB201908453D0 (en) * | 2019-06-12 | 2019-07-24 | Enterprise Therapeutics Ltd | Compounds for treating respiratory disease |
| CA3164134A1 (en) * | 2019-12-06 | 2021-06-10 | Vertex Pharmaceuticals Incorporated | Substituted tetrahydrofurans as modulators of sodium channels |
| BR112023026747A2 (pt) | 2021-06-18 | 2024-03-12 | Aligos Therapeutics Inc | Métodos e composições para direcionamento de pd-l1 |
| CA3240346A1 (en) | 2021-12-16 | 2023-06-22 | Aligos Therapeutics, Inc. | Methods and compositions for targeting pd-l1 |
| WO2024059207A2 (en) * | 2022-09-15 | 2024-03-21 | Vanderbilt University | Pyrazoloether analogs as mglu5 negative allosteric modulators and methods of making and using the same |
| WO2025085233A1 (en) * | 2023-10-20 | 2025-04-24 | Ensem Therapeutics, Inc. | Novel derivatives of quinolinones, and compositions and methods thereof |
| CN117567298B (zh) * | 2023-11-16 | 2025-08-05 | 上海馨远医药科技有限公司 | 一种手性1-(2-氟-3-(三氟甲基)苯基)乙胺的制备方法 |
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| JPH0725853A (ja) * | 1993-07-14 | 1995-01-27 | Ishihara Sangyo Kaisha Ltd | アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤 |
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| CN1688546A (zh) * | 2000-09-18 | 2005-10-26 | 纳幕尔杜邦公司 | 用作杀真菌剂的吡啶酰胺类和吡啶酰亚胺类 |
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| TW200407075A (en) * | 2002-03-19 | 2004-05-16 | Du Pont | Pyridinyl amides and advantageous compositions thereof for use as fungicides |
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| EP2307379A2 (en) | 2008-06-27 | 2011-04-13 | Novartis AG | Organic compounds |
| WO2010035166A1 (en) | 2008-09-23 | 2010-04-01 | Pfizer Limited | Benzamide derivatives |
| ES2534199T3 (es) * | 2008-10-31 | 2015-04-20 | Merck Sharp & Dohme Corp. | Antagonistas del receptor P2X3 para el tratamiento del dolor |
| EP2435407B1 (en) * | 2009-05-29 | 2019-12-25 | RaQualia Pharma Inc. | Aryl substituted carboxamide derivatives as calcium or sodium channel blockers |
| WO2011016234A1 (en) * | 2009-08-04 | 2011-02-10 | Raqualia Pharma Inc. | Picolinamide derivatives as ttx-s blockers |
| EP2630122B1 (en) * | 2010-10-18 | 2016-11-30 | RaQualia Pharma Inc | Arylamide derivatives as ttx-s blockers |
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- 2011-10-18 US US13/879,673 patent/US9302991B2/en active Active
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