TWI600654B - 用於治療寄生蟲疾病之化合物及組合物 - Google Patents

Info

Publication number

TWI600654B

TWI600654B TW102141950A TW102141950A TWI600654B TW I600654 B TWI600654 B TW I600654B TW 102141950 A TW102141950 A TW 102141950A TW 102141950 A TW102141950 A TW 102141950A TW I600654 B TWI600654 B TW I600654B

Authority

TW

Taiwan

Prior art keywords

pyridine

pyrazolo

phenyl

carboxamide

methyl

Prior art date

2012-11-19

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 242
• 239000000203 mixture Substances 0.000 title claims description 112
• 238000011282 treatment Methods 0.000 title description 22
• 208000030852 Parasitic disease Diseases 0.000 title description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 173
• -1 pyrrolopyridinyl Chemical group 0.000 claims description 164
• 125000000217 alkyl group Chemical group 0.000 claims description 144
• XCDRZFXDJGFXBD-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=C(C(=O)N)C=CN2N=CC=C21 XCDRZFXDJGFXBD-UHFFFAOYSA-N 0.000 claims description 106
• 150000003839 salts Chemical class 0.000 claims description 102
• 125000001072 heteroaryl group Chemical group 0.000 claims description 57
• 125000003118 aryl group Chemical group 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 52
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 51
• 241000223960 Plasmodium falciparum Species 0.000 claims description 49
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 46
• 125000003545 alkoxy group Chemical group 0.000 claims description 45
• 244000045947 parasite Species 0.000 claims description 45
• 150000001412 amines Chemical class 0.000 claims description 39
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
• 201000010099 disease Diseases 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 36
• 201000004792 malaria Diseases 0.000 claims description 31
• 125000003282 alkyl amino group Chemical group 0.000 claims description 30
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 239000003795 chemical substances by application Substances 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 28
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 23
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 22
• 208000024891 symptom Diseases 0.000 claims description 22
• 230000007170 pathology Effects 0.000 claims description 19
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
• 125000003277 amino group Chemical group 0.000 claims description 14
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 125000002619 bicyclic group Chemical group 0.000 claims description 13
• BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 12
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 12
• 239000004202 carbamide Substances 0.000 claims description 11
• DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 claims description 11
• 230000005764 inhibitory process Effects 0.000 claims description 10
• 210000004185 liver Anatomy 0.000 claims description 10
• 150000001408 amides Chemical class 0.000 claims description 9
• 210000004369 blood Anatomy 0.000 claims description 9
• 239000008280 blood Substances 0.000 claims description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 8
• LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• DQHCWIQEOFOVPG-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-(1h-pyrrolo[2,3-b]pyridin-5-yl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CN2N=CC(C=3C=C4C=CNC4=NC=3)=C2C=C1C(=O)N(C)C1=CC=C(C#N)C=C1 DQHCWIQEOFOVPG-UHFFFAOYSA-N 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• UNDKBYLRRRBDGL-UHFFFAOYSA-N CN(C(C(C=CN1N=C2)=CC1=C2C1=CC=C(CN)C=C1)=O)C(C=C1)=NC=C1C#N Chemical compound CN(C(C(C=CN1N=C2)=CC1=C2C1=CC=C(CN)C=C1)=O)C(C=C1)=NC=C1C#N UNDKBYLRRRBDGL-UHFFFAOYSA-N 0.000 claims description 6
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 6
• ACEBZLKNNKVZGS-UHFFFAOYSA-N 3-(4-aminophenyl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(N)C=C1 ACEBZLKNNKVZGS-UHFFFAOYSA-N 0.000 claims description 5
• INEYQUSNXLVTDG-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(N)N=C1 INEYQUSNXLVTDG-UHFFFAOYSA-N 0.000 claims description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 5
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 5
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 4
• KCSUAVGGFJSNQG-UHFFFAOYSA-N 3-(2-aminopyrimidin-5-yl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)N=C1 KCSUAVGGFJSNQG-UHFFFAOYSA-N 0.000 claims description 4
• LQQLJLYZAUDRTO-UHFFFAOYSA-N 3-[6-amino-5-(trifluoromethyl)pyridin-3-yl]-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)C(C(F)(F)F)=C1 LQQLJLYZAUDRTO-UHFFFAOYSA-N 0.000 claims description 4
• JQKWXWZESAYCIW-UHFFFAOYSA-N 4-[5-(7-fluoro-3-methyl-2,3-dihydro-1,4-benzoxazine-4-carbonyl)pyrazolo[1,5-a]pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N3C4=CC=C(F)C=C4OCC3C)C=CN2N=C1 JQKWXWZESAYCIW-UHFFFAOYSA-N 0.000 claims description 4
• GOEFACQHAYWRAQ-UHFFFAOYSA-N 5-[2-(4-fluorophenyl)ethyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1CCC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 GOEFACQHAYWRAQ-UHFFFAOYSA-N 0.000 claims description 4
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 4
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• RUSOLNJHZUEOGG-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 RUSOLNJHZUEOGG-UHFFFAOYSA-N 0.000 claims description 4
• IYEKAGXIGWYWCV-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-(5-methoxypyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=CC(OC)=CC=C1C1=C2C=C(C(=O)N(C)C=3N=CC(=CC=3)C#N)C=CN2N=C1 IYEKAGXIGWYWCV-UHFFFAOYSA-N 0.000 claims description 4
• NYKBGHFUPNQBFS-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-methyl-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 NYKBGHFUPNQBFS-UHFFFAOYSA-N 0.000 claims description 4
• NAUKWDRTUSNMMD-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=CC(F)=CC=C1CNC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 NAUKWDRTUSNMMD-UHFFFAOYSA-N 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
• HSRPYWABXCSKIO-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-methyl-1-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]urea Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(F)(F)F)=C2C=C1N(C)C(=O)NC1=CC=C(F)C=C1 HSRPYWABXCSKIO-UHFFFAOYSA-N 0.000 claims description 3
• JYPKQLSJEKQADI-UHFFFAOYSA-N 3-(6-amino-5-fluoropyridin-3-yl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)C(F)=C1 JYPKQLSJEKQADI-UHFFFAOYSA-N 0.000 claims description 3
• CXJIVALQEWZFDB-UHFFFAOYSA-N 4-fluoro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzenesulfonamide Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)N(C)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 CXJIVALQEWZFDB-UHFFFAOYSA-N 0.000 claims description 3
• POPQAGDJJFNTNA-UHFFFAOYSA-N 5-[(4-fluorophenoxy)methyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1OCC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 POPQAGDJJFNTNA-UHFFFAOYSA-N 0.000 claims description 3
• MNCSCAZLWXELFK-UHFFFAOYSA-N 5-[(4-fluorophenyl)sulfanylmethyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1SCC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 MNCSCAZLWXELFK-UHFFFAOYSA-N 0.000 claims description 3
• MCROLCIKKFTXML-UHFFFAOYSA-N 5-[(4-fluorophenyl)sulfinylmethyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound C1=CC(F)=CC=C1S(=O)CC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 MCROLCIKKFTXML-UHFFFAOYSA-N 0.000 claims description 3
• HAAMTDVCPQYNMK-UHFFFAOYSA-N 5-[(5-methylpyridin-2-yl)oxymethyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine Chemical compound N1=CC(C)=CC=C1OCC1=CC2=C(C=3C=CC(=CC=3)C(F)(F)F)C=NN2C=C1 HAAMTDVCPQYNMK-UHFFFAOYSA-N 0.000 claims description 3
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• DDXWTGKHOJVHRG-UHFFFAOYSA-N CN(C1=CC2=C(C=NN2C=C1)C3=CC=C(C=C3)CN)C(=O)C4=CC=C(C=C4)F Chemical compound CN(C1=CC2=C(C=NN2C=C1)C3=CC=C(C=C3)CN)C(=O)C4=CC=C(C=C4)F DDXWTGKHOJVHRG-UHFFFAOYSA-N 0.000 claims description 3
• LHAYUAPEFQAINR-QGZVFWFLSA-N C[C@H](CNC1=CC=C(C=C1)C2=C3C=C(C=CN3N=C2)C(=O)N(C)C4=CC=C(C=C4)C#N)N Chemical compound C[C@H](CNC1=CC=C(C=C1)C2=C3C=C(C=CN3N=C2)C(=O)N(C)C4=CC=C(C=C4)C#N)N LHAYUAPEFQAINR-QGZVFWFLSA-N 0.000 claims description 3
• 235000010233 benzoic acid Nutrition 0.000 claims description 3
• 230000008029 eradication Effects 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• KUUWPDFSONAWGQ-UHFFFAOYSA-N n-(4-fluorophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(F)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 KUUWPDFSONAWGQ-UHFFFAOYSA-N 0.000 claims description 3
• FBDMSZQQZWJIPM-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-methyl-3-(5-methylpyridin-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C)C=N1 FBDMSZQQZWJIPM-UHFFFAOYSA-N 0.000 claims description 3
• OGRSJOKFJKMBLF-UHFFFAOYSA-N n-methyl-4-methylsulfonyl-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(F)(F)F)=C2C=C1N(C)C(=O)C1=CC=C(S(C)(=O)=O)C=C1 OGRSJOKFJKMBLF-UHFFFAOYSA-N 0.000 claims description 3
• DMIUBBRIWCMDNC-UHFFFAOYSA-N n-methyl-n-(5-methylpyridin-2-yl)-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 DMIUBBRIWCMDNC-UHFFFAOYSA-N 0.000 claims description 3
• RKHNDRNBMJFYCQ-UHFFFAOYSA-N n-methyl-n-(5-methylpyridin-3-yl)-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1N=CC(C)=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 RKHNDRNBMJFYCQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• AEWORWAKEFTHQF-UHFFFAOYSA-N pyrazolo[1,5-a]pyridin-5-amine Chemical compound C1=C(N)C=CN2N=CC=C21 AEWORWAKEFTHQF-UHFFFAOYSA-N 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• HBDJXFWAWKERIG-UHFFFAOYSA-N 3-(2-aminopyridin-4-yl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=NC(N)=C1 HBDJXFWAWKERIG-UHFFFAOYSA-N 0.000 claims description 2
• GUKQBKQCUDJBSA-UHFFFAOYSA-N 3-(4-acetamidophenyl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(NC(C)=O)C=C1 GUKQBKQCUDJBSA-UHFFFAOYSA-N 0.000 claims description 2
• PTEIXJMQQFZISE-UHFFFAOYSA-N 3-(4-amino-3,5-dimethylphenyl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC(C)=C(N)C(C)=C1 PTEIXJMQQFZISE-UHFFFAOYSA-N 0.000 claims description 2
• MMVFCZWRKCJRRU-UHFFFAOYSA-N 3-(6-amino-5-methylpyridin-3-yl)-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(N)C(C)=C1 MMVFCZWRKCJRRU-UHFFFAOYSA-N 0.000 claims description 2
• WMTRRHDMJAGPOE-UHFFFAOYSA-N 3-[6-chloro-5-(methanesulfonamido)pyridin-3-yl]-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CN=C(Cl)C(NS(C)(=O)=O)=C1 WMTRRHDMJAGPOE-UHFFFAOYSA-N 0.000 claims description 2
• OXMVLJHPBWICNO-UHFFFAOYSA-N 4-[5-[1-[methyl-(5-methylpyridin-2-yl)amino]ethyl]pyrazolo[1,5-a]pyridin-3-yl]benzamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(N)=O)=C2C=C1C(C)N(C)C1=CC=C(C)C=N1 OXMVLJHPBWICNO-UHFFFAOYSA-N 0.000 claims description 2
• FOMOTRJNAJNRTM-UHFFFAOYSA-N 4-chloro-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(F)(F)F)=C2C=C1N(C)C(=O)C1=CC=C(Cl)C=C1 FOMOTRJNAJNRTM-UHFFFAOYSA-N 0.000 claims description 2
• TXSNDSCJHXCDRG-UHFFFAOYSA-N 4-cyano-n-(oxan-4-ylmethyl)-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C2C=C(N(CC3CCOCC3)C(=O)C=3C=CC(=CC=3)C#N)C=CN2N=C1 TXSNDSCJHXCDRG-UHFFFAOYSA-N 0.000 claims description 2
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
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