KR101458006B1 - Ttx-s 차단제로서의 아릴아미드 유도체 - Google Patents
Ttx-s 차단제로서의 아릴아미드 유도체 Download PDFInfo
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- KR101458006B1 KR101458006B1 KR1020137012638A KR20137012638A KR101458006B1 KR 101458006 B1 KR101458006 B1 KR 101458006B1 KR 1020137012638 A KR1020137012638 A KR 1020137012638A KR 20137012638 A KR20137012638 A KR 20137012638A KR 101458006 B1 KR101458006 B1 KR 101458006B1
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- KR
- South Korea
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims abstract description 394
- -1 (6- (2,2,2-trifluoroethoxy) pyridin-3-yl) methyl Chemical group 0.000 claims description 1111
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 706
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 166
- 239000007787 solid Substances 0.000 claims description 133
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 124
- 125000001424 substituent group Chemical group 0.000 claims description 118
- 125000000217 alkyl group Chemical group 0.000 claims description 108
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 81
- 238000000034 method Methods 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 61
- 150000002367 halogens Chemical class 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 239000000126 substance Substances 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims description 29
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- 238000007429 general method Methods 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 8
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Chemical group 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 150000003857 carboxamides Chemical class 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 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 description 5
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 235000005152 nicotinamide Nutrition 0.000 claims description 5
- 239000011570 nicotinamide Substances 0.000 claims description 5
- 229960003966 nicotinamide Drugs 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 5
- PTXDINCSDOVDHF-UHFFFAOYSA-N 2-(2-methylpropanoylamino)-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyridine-4-carboxamide Chemical compound C1=NC(NC(=O)C(C)C)=CC(C(=O)NC(C)C=2C=NC(OCC(F)(F)F)=CC=2)=C1 PTXDINCSDOVDHF-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- QVXALHNAIKGBRC-UHFFFAOYSA-N n-[1-[5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]-2-methyl-6-(2-methylpropanoylamino)pyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C(C)C)=CC(C(=O)NC(C)C=2C=C(F)C(OCC(F)(F)F)=NC=2)=C1 QVXALHNAIKGBRC-UHFFFAOYSA-N 0.000 claims description 4
- FXJJTXFKVHXMBU-UHFFFAOYSA-N n-[1-[6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl]ethyl]-2-methyl-6-(2-methylpropanoylamino)pyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C(C)C)=CC(C(=O)NC(C)C=2C=C(C)C(OCC(F)F)=NC=2)=C1 FXJJTXFKVHXMBU-UHFFFAOYSA-N 0.000 claims description 4
- XTALZYQSPUACCJ-UHFFFAOYSA-N n-[1-[6-(2,2-difluoropropoxy)pyridin-3-yl]ethyl]-2-methyl-6-(2-methylpropanoylamino)pyridine-4-carboxamide Chemical compound CC1=NC(NC(=O)C(C)C)=CC(C(=O)NC(C)C=2C=NC(OCC(C)(F)F)=CC=2)=C1 XTALZYQSPUACCJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 3
- QYIIRRVJUMICSK-UHFFFAOYSA-N 2-(2-methylpropanoylamino)-n-[1-[4-(2,2,2-trifluoroethoxy)phenyl]ethyl]pyrimidine-4-carboxamide Chemical compound CC(C)C(=O)NC1=NC=CC(C(=O)NC(C)C=2C=CC(OCC(F)(F)F)=CC=2)=N1 QYIIRRVJUMICSK-UHFFFAOYSA-N 0.000 claims description 2
- MPMHTQIDQIIYRW-UHFFFAOYSA-N 2-(2-methylpropanoylamino)-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound CC(C)C(=O)NC1=NC=CC(C(=O)NC(C)C=2C=NC(OCC(F)(F)F)=CC=2)=N1 MPMHTQIDQIIYRW-UHFFFAOYSA-N 0.000 claims description 2
- WWPWVLHVLJQFLN-UHFFFAOYSA-N 2-(2-methylpropanoylamino)-n-[[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]pyrimidine-4-carboxamide Chemical compound CC(C)C(=O)NC1=NC=CC(C(=O)NCC=2C=NC(OCC(F)(F)F)=CC=2)=N1 WWPWVLHVLJQFLN-UHFFFAOYSA-N 0.000 claims description 2
- LQOVEEJOIKJKKU-UHFFFAOYSA-N 2-(4-cyclopropylbutanoylamino)-N-[1-[6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl]ethyl]-6-methylpyridine-4-carboxamide Chemical compound C1(CC1)CCCC(=O)NC=1C=C(C(=O)NC(C)C=2C=NC(=C(C2)C)OCC(F)F)C=C(N1)C LQOVEEJOIKJKKU-UHFFFAOYSA-N 0.000 claims description 2
- PFBSGDCWYLINMA-UHFFFAOYSA-N 2-(cyclopropanecarbonylamino)-N-[[5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methyl]-6-methyl-1H-pyrimidine-2-carboxamide Chemical compound C1(CC1)C(=O)NC1(NC(=CC=N1)C)C(=O)NCC=1C=NC(=C(C1)F)OCC(F)(F)F PFBSGDCWYLINMA-UHFFFAOYSA-N 0.000 claims description 2
- NHIHDWMEJXQLDG-SNVBAGLBSA-N 2-(propanoylamino)-n-[(1r)-1-[3-(trifluoromethyl)phenyl]ethyl]pyrimidine-4-carboxamide Chemical compound CCC(=O)NC1=NC=CC(C(=O)N[C@H](C)C=2C=C(C=CC=2)C(F)(F)F)=N1 NHIHDWMEJXQLDG-SNVBAGLBSA-N 0.000 claims description 2
- DOKWQWVACWMVHO-UHFFFAOYSA-N 2-(propanoylamino)-n-[1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound CCC(=O)NC1=NC=CC(C(=O)NC(C)C=2C=NC(OCC(F)(F)F)=CC=2)=N1 DOKWQWVACWMVHO-UHFFFAOYSA-N 0.000 claims description 2
- TZPBHMVJNAGMTF-UHFFFAOYSA-N 2-(propanoylamino)-n-[1-[6-(3,3,3-trifluoropropoxy)pyridin-3-yl]ethyl]pyrimidine-4-carboxamide Chemical compound CCC(=O)NC1=NC=CC(C(=O)NC(C)C=2C=NC(OCCC(F)(F)F)=CC=2)=N1 TZPBHMVJNAGMTF-UHFFFAOYSA-N 0.000 claims description 2
- UXDOAGHTKQPDAT-UHFFFAOYSA-N 2-[(2-cyclopropylacetyl)amino]-n-[[6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl]methyl]-6-methylpyridine-4-carboxamide Chemical compound N=1C(C)=CC(C(=O)NCC=2C=C(C)C(OCC(F)F)=NC=2)=CC=1NC(=O)CC1CC1 UXDOAGHTKQPDAT-UHFFFAOYSA-N 0.000 claims description 2
- FDBRKYUEFZNPCZ-UHFFFAOYSA-N 2-[(2-hydroxy-2-methylpropanoyl)amino]-n-[[2-methoxy-3-(trifluoromethyl)phenyl]methyl]-6-methylpyridine-4-carboxamide Chemical compound C1=CC=C(C(F)(F)F)C(OC)=C1CNC(=O)C1=CC(C)=NC(NC(=O)C(C)(C)O)=C1 FDBRKYUEFZNPCZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- 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 description 2
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| ES2645984T3 (es) | 2012-04-25 | 2017-12-11 | Raqualia Pharma Inc | Derivados de pirrolopiridinona como bloqueadores de TTX-S |
| MX366308B (es) * | 2012-04-25 | 2019-07-04 | Raqualia Pharma Inc | Derivados de amida como bloqueadores de ttx-s. |
| BR112015009738A8 (pt) | 2012-10-31 | 2019-09-17 | Raqualia Pharma Inc | composto , uso do referido composto no tratamento de uma condição ou distúrbio em que bloqueadores de canal ttx-s, composição farmacêutica contendo o referido composto e processo para preparar a referida composição |
| KR20160118345A (ko) * | 2014-02-06 | 2016-10-11 | 애브비 인코포레이티드 | 6-헤테로아릴옥시- 및 6-아릴옥시-퀴놀린-2-카복사미드 및 이의 용도 |
| US10441586B2 (en) | 2015-10-07 | 2019-10-15 | Arizona Board Of Regents On Behalf Of The University Of Arizona | CRMP2 SUMOylation inhibitors and uses thereof |
| US12084472B2 (en) | 2015-12-18 | 2024-09-10 | Ardelyx, Inc. | Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists |
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| CN108430972B (zh) * | 2015-12-24 | 2022-12-27 | 协和麒麟株式会社 | α,β不饱和酰胺化合物 |
| 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 |
| US11046683B2 (en) | 2016-12-15 | 2021-06-29 | Ono Pharmaceutical Co., Ltd. | Activator of TREK (TWIK RElated K+ channels) channels |
| US20200039930A1 (en) | 2017-03-21 | 2020-02-06 | AbbVie Deutschland GmbH & Co. KG | Proline amide compounds and their azetidine analogues carrying a specifically substituted benzyl radical |
| ES2851004T3 (es) * | 2017-06-20 | 2021-09-02 | Raqualia Pharma Inc | Derivados de amida como bloqueadores de NAV1.7 y NAV1.8 |
| WO2019045035A1 (en) * | 2017-08-31 | 2019-03-07 | Raqualia Pharma Inc. | BIARYLOXY DERIVATIVES AS TTX-S BLOCKERS |
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| RU2761824C2 (ru) * | 2018-08-03 | 2021-12-13 | Закрытое Акционерное Общество "Биокад" | Ингибиторы CDK8/19 |
| AR116939A1 (es) * | 2018-11-02 | 2021-06-30 | Merck Sharp & Dohme | 2-amino-n-heteroaril-nicotinamidas como inhibidores de nav1.8 |
| 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 |
| MX2022006865A (es) | 2019-12-06 | 2022-07-11 | Vertex Pharma | Tetrahidrofuranos sustituidos como moduladores de canales de sodio. |
| JP2024525160A (ja) | 2021-06-18 | 2024-07-10 | アリゴス セラピューティクス インコーポレイテッド | Pd-l1を標的とするための方法及び組成物 |
| TW202328139A (zh) | 2021-12-16 | 2023-07-16 | 美商艾利格斯醫療公司 | 用於靶向pd-l1之方法及組成物 |
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