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

用於治療寄生蟲疾病之化合物及組合物 Download PDF

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Publication number: TWI600654B
Authority: TW; Taiwan
Prior art keywords: pyridine; pyrazolo; phenyl; carboxamide; methyl
Prior art date: 2012-11-19

Application number

TW102141950A

Other languages

English (en)

Chinese (zh)

Other versions

TW201429967A (zh

Inventor

雅那伯夏特吉

艾德維特奈葛雷

普拉蘇納帕拉賽利

拉維恩德雷迪康卓狄

梁世勇

波那伯米席拉

羅伯摩洛

傑森湯瑪士羅蘭

維琳珊卓拉沈

賽門奧利佛

麗英喬瑟琳陳

布萊恩ＫＳ楊

鄒彬

凡卡塔塔艾布魯

Original Assignee

艾姆公司

諾華公司

Priority date (The priority date 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 date listed.)

2012-11-19

Filing date

2013-11-18

Publication date

2017-10-01

2013-11-18 Application filed by 艾姆公司, 諾華公司 filed Critical 艾姆公司

2014-08-01 Publication of TW201429967A publication Critical patent/TW201429967A/zh

2017-10-01 Application granted granted Critical

2017-10-01 Publication of TWI600654B publication Critical patent/TWI600654B/zh

Links

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
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
- A—HUMAN NECESSITIES
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- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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TW102141950A 2012-11-19 2013-11-18 用於治療寄生蟲疾病之化合物及組合物 TWI600654B (zh)

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- 2013-11-18 LT LTEP13795977.1T patent/LT2925757T/lt unknown
- 2013-11-18 CN CN201380070822.0A patent/CN105164124B/zh not_active Expired - Fee Related
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AR093532A1 (es)	2015-06-10
CN105164124B (zh)	2017-03-15
US20180230145A1 (en)	2018-08-16
CY1119727T1 (el)	2018-06-27
CN105164124A (zh)	2015-12-16
EP2925757B1 (en)	2017-10-04
WO2014078802A1 (en)	2014-05-22
HRP20171998T1 (hr)	2018-02-09
RS56720B1 (sr)	2018-03-30
US9926314B2 (en)	2018-03-27
JP6298472B2 (ja)	2018-03-20
TW201429967A (zh)	2014-08-01
DK2925757T3 (en)	2018-01-15
EP2925757A1 (en)	2015-10-07
ES2655030T3 (es)	2018-02-16
UY35146A (es)	2014-06-30
ME03042B (me)	2018-10-20
LT2925757T (lt)	2017-12-27
US9556169B2 (en)	2017-01-31
PT2925757T (pt)	2018-01-09
PL2925757T3 (pl)	2018-06-29
US20150344471A1 (en)	2015-12-03
US20160333012A1 (en)	2016-11-17
SI2925757T1 (en)	2018-01-31
JP2016505529A (ja)	2016-02-25
HUE037600T2 (hu)	2018-09-28

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