JP2016505529A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016505529A5 JP2016505529A5 JP2015542882A JP2015542882A JP2016505529A5 JP 2016505529 A5 JP2016505529 A5 JP 2016505529A5 JP 2015542882 A JP2015542882 A JP 2015542882A JP 2015542882 A JP2015542882 A JP 2015542882A JP 2016505529 A5 JP2016505529 A5 JP 2016505529A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridine
- carboxamide
- pyrazolo
- phenyl
- pyridin
- 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.)
- Granted
Links
- -1 amino, hydroxyl Chemical group 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000001475 halogen functional group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- AFEBSUBJPYNMLX-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-methyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3N=CC(=CC=3)C#N)C=CN2N=C1 AFEBSUBJPYNMLX-UHFFFAOYSA-N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 7
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 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
- 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 4
- LYBINGBMBQCIEI-MRXNPFEDSA-N 3-[4-[[(2r)-2-aminopropanoyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(NC(=O)[C@H](N)C)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C#N)C=CN2N=C1 LYBINGBMBQCIEI-MRXNPFEDSA-N 0.000 claims description 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 4
- VQPZEJHSUIMXJJ-UHFFFAOYSA-N 5-[5-[(4-cyanophenyl)-(methylamino)carbamoyl]pyrazolo[1,5-a]pyridin-3-yl]-n-methylpyridine-2-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(NC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)N=C1 VQPZEJHSUIMXJJ-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 241000223960 Plasmodium falciparum Species 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 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 4
- OVGPNIIHANOLRC-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-[4-(methylcarbamoyl)phenyl]-n-propan-2-ylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C(C)C)C=3N=CC(=CC=3)C#N)C=CN2N=C1 OVGPNIIHANOLRC-UHFFFAOYSA-N 0.000 claims description 4
- MIVQLYOYCUPNAP-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-cyclopropyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 MIVQLYOYCUPNAP-UHFFFAOYSA-N 0.000 claims description 4
- XOHVCFFOEUGXDR-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-ethyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)C=C1 XOHVCFFOEUGXDR-UHFFFAOYSA-N 0.000 claims description 4
- IHZSERRLWDIUDF-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-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=N1 IHZSERRLWDIUDF-UHFFFAOYSA-N 0.000 claims description 4
- YVQPAOQGADXRII-UHFFFAOYSA-N n-ethyl-n-(5-fluoropyridin-2-yl)-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(F)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)C=C1 YVQPAOQGADXRII-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- INYLWQYLPVRIOG-UHFFFAOYSA-N 3-[6-amino-5-(dimethylcarbamoyl)pyridin-3-yl]-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=C(N)C(C(=O)N(C)C)=CC(C2=C3C=C(C=CN3N=C2)C(=O)N(C)C=2N=CC(=CC=2)C#N)=C1 INYLWQYLPVRIOG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
- FIMDPLQFEMZNQZ-UHFFFAOYSA-N n-ethyl-3-[4-(methylcarbamoyl)phenyl]-n-[5-(trifluoromethyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)C=C1 FIMDPLQFEMZNQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 2
- RHXCIZLMUVKMGE-UHFFFAOYSA-N 2-amino-2-cyclohexylacetamide Chemical compound NC(=O)C(N)C1CCCCC1 RHXCIZLMUVKMGE-UHFFFAOYSA-N 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
- 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 2
- BHSQRNJDDWAUDW-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-chloro-2-formylphenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(Cl)C=C(C=O)C=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=C1 BHSQRNJDDWAUDW-UHFFFAOYSA-N 0.000 claims description 2
- CEUMFLHANBUGHU-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-chlorophenyl)-n-methylpyrazolo[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(N)=O)C=C1 CEUMFLHANBUGHU-UHFFFAOYSA-N 0.000 claims description 2
- GXWIIYKIVTXJHQ-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-cyanocyclohexyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(N)=O)=C2C=C1C(=O)N(C)C1CCC(C#N)CC1 GXWIIYKIVTXJHQ-UHFFFAOYSA-N 0.000 claims description 2
- AVVFTCJUJWRJIF-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-cyanophenyl)-n-(2-hydroxyethyl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(CCO)C=3C=CC(=CC=3)C#N)C=CN2N=C1 AVVFTCJUJWRJIF-UHFFFAOYSA-N 0.000 claims description 2
- RETWKVPBIKVKNP-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-cyanophenyl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(=CC=3)C#N)C=CN2N=C1 RETWKVPBIKVKNP-UHFFFAOYSA-N 0.000 claims description 2
- RQRAIWVNBUQEFG-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-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)=O)C=C1 RQRAIWVNBUQEFG-UHFFFAOYSA-N 0.000 claims description 2
- RYUOSSVZFZYALJ-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(4-fluorophenyl)-n-methylpyrazolo[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(N)=O)C=C1 RYUOSSVZFZYALJ-UHFFFAOYSA-N 0.000 claims description 2
- ORBRBJUPZJBEFK-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-(5-cyanopyridin-2-yl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 ORBRBJUPZJBEFK-UHFFFAOYSA-N 0.000 claims description 2
- YTIYJNWWLQSAAU-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-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(C(N)=O)C=C1 YTIYJNWWLQSAAU-UHFFFAOYSA-N 0.000 claims description 2
- JUNGICCWVXZLQG-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-cyclopropyl-n-(3,4-difluorophenyl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=C(F)C(F)=CC=3)C=CN2N=C1 JUNGICCWVXZLQG-UHFFFAOYSA-N 0.000 claims description 2
- NYIRQOMRHCHWBH-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-methyl-n-(5-methylpyridin-2-yl)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(N)=O)C=C1 NYIRQOMRHCHWBH-UHFFFAOYSA-N 0.000 claims description 2
- NSCNEKGRISNFKI-UHFFFAOYSA-N 3-(4-carbamoylphenyl)-n-methyl-n-[5-(trifluoromethyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(N)=O)C=C1 NSCNEKGRISNFKI-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- DUOVQOGMQOZJDE-UHFFFAOYSA-N 3-(5-amino-6-chloropyridin-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(N)=C1 DUOVQOGMQOZJDE-UHFFFAOYSA-N 0.000 claims description 2
- ZZXUGDGOKYDEDY-UHFFFAOYSA-N 3-(5-carbamoylpyridin-2-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(C(N)=O)C=N1 ZZXUGDGOKYDEDY-UHFFFAOYSA-N 0.000 claims description 2
- IBMMICVBFWIOGS-UHFFFAOYSA-N 3-(5-carbamoylpyridin-2-yl)-n-(5-cyanopyridin-2-yl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 IBMMICVBFWIOGS-UHFFFAOYSA-N 0.000 claims description 2
- QTAMHHUFTFOTLR-UHFFFAOYSA-N 3-(5-carbamoylpyridin-2-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=C(C(N)=O)C=N1 QTAMHHUFTFOTLR-UHFFFAOYSA-N 0.000 claims description 2
- HAQDWUVBQZXLGW-UHFFFAOYSA-N 3-(6-acetamidopyridin-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(NC(C)=O)N=C1 HAQDWUVBQZXLGW-UHFFFAOYSA-N 0.000 claims description 2
- LTAWNKYSHWNFMT-UHFFFAOYSA-N 3-(6-amino-5-chloropyridin-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(Cl)=C1 LTAWNKYSHWNFMT-UHFFFAOYSA-N 0.000 claims description 2
- QOKZKONINLLRQF-UHFFFAOYSA-N 3-(6-amino-5-cyanopyridin-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#N)=C1 QOKZKONINLLRQF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- LCBMVGDIOXWCAR-UHFFFAOYSA-N 3-(6-amino-5-methoxypyridin-3-yl)-n-(5-cyanopyridin-2-yl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=C(N)C(OC)=CC(C2=C3C=C(C=CN3N=C2)C(=O)N(C)C=2N=CC(=CC=2)C#N)=C1 LCBMVGDIOXWCAR-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
- VHVKCJJECWKSDS-UHFFFAOYSA-N 3-(6-aminopyridin-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=CC=C(N)N=C1 VHVKCJJECWKSDS-UHFFFAOYSA-N 0.000 claims description 2
- JJXDASHHKUGLBN-UHFFFAOYSA-N 3-(6-carbamoylpyridin-3-yl)-n-(4-cyanophenyl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(=CC=3)C#N)C=CN2N=C1 JJXDASHHKUGLBN-UHFFFAOYSA-N 0.000 claims description 2
- XGMGXFIOFMLJIM-UHFFFAOYSA-N 3-[4-(2-aminoethylcarbamoyl)phenyl]-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(C(=O)NCCN)C=C1 XGMGXFIOFMLJIM-UHFFFAOYSA-N 0.000 claims description 2
- XCYDPRNLYOSTDK-UHFFFAOYSA-N 3-[4-[(2-aminoacetyl)amino]phenyl]-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(NC(=O)CN)C=C1 XCYDPRNLYOSTDK-UHFFFAOYSA-N 0.000 claims description 2
- OJLDETSJNURQBL-VWLOTQADSA-N 3-[4-[[(2s)-2-amino-3-methylbutanoyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(NC(=O)[C@@H](N)C(C)C)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C#N)C=CN2N=C1 OJLDETSJNURQBL-VWLOTQADSA-N 0.000 claims description 2
- LYBINGBMBQCIEI-INIZCTEOSA-N 3-[4-[[(2s)-2-aminopropanoyl]amino]phenyl]-n-(4-cyanophenyl)-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(NC(=O)[C@@H](N)C)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C#N)C=CN2N=C1 LYBINGBMBQCIEI-INIZCTEOSA-N 0.000 claims description 2
- 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 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
- XFLNXYYZBCWZOZ-UHFFFAOYSA-N 4-[5-(7-fluoro-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=C4OCC3)C=CN2N=C1 XFLNXYYZBCWZOZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- VIWNXLMAPVRFHB-UHFFFAOYSA-N 4-[5-[(4-fluorobenzoyl)-methylamino]pyrazolo[1,5-a]pyridin-3-yl]benzamide Chemical compound C1=CN2N=CC(C=3C=CC(=CC=3)C(N)=O)=C2C=C1N(C)C(=O)C1=CC=C(F)C=C1 VIWNXLMAPVRFHB-UHFFFAOYSA-N 0.000 claims description 2
- DLGFTAJFANEHOI-UHFFFAOYSA-N 4-[5-[(5-cyanopyridin-2-yl)-cyclopropylsulfamoyl]pyrazolo[1,5-a]pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(S(=O)(=O)N(C3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 DLGFTAJFANEHOI-UHFFFAOYSA-N 0.000 claims description 2
- WTEJFLHRTLMMED-UHFFFAOYSA-N 4-[5-[(5-cyanopyridin-2-yl)-methylcarbamoyl]pyrazolo[1,5-a]pyridin-3-yl]benzoic acid Chemical compound C=1C=C(C#N)C=NC=1N(C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(O)=O)C=C1 WTEJFLHRTLMMED-UHFFFAOYSA-N 0.000 claims description 2
- CHFAOPMBMRLUFX-UHFFFAOYSA-N 4-[5-[(5-cyanopyridin-2-yl)-methylsulfamoyl]pyrazolo[1,5-a]pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(S(=O)(=O)N(C)C=3N=CC(=CC=3)C#N)C=CN2N=C1 CHFAOPMBMRLUFX-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
- LFMDYWOTIXBDRY-UHFFFAOYSA-N 4-cyano-n-methyl-n-[3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridin-5-yl]benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(C)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 LFMDYWOTIXBDRY-UHFFFAOYSA-N 0.000 claims description 2
- OBTXCMGPGHMGIT-UHFFFAOYSA-N 4-cyclopropyl-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)C(C=C1)=CC=C1C1CC1 OBTXCMGPGHMGIT-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- VYLUHYBMTOAFRM-UHFFFAOYSA-N 6-[cyclopropyl-[3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carbonyl]amino]pyridine-3-carboxylic acid Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C(O)=O)C=CN2N=C1 VYLUHYBMTOAFRM-UHFFFAOYSA-N 0.000 claims description 2
- YCGQUZBFFSNOKK-UHFFFAOYSA-N N-(4-cyanophenyl)-N-cyclopropyl-3-[6-(methylcarbamoyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound CNC(=O)c1ccc(cn1)-c1cnn2ccc(cc12)C(=O)N(C1CC1)c1ccc(cc1)C#N YCGQUZBFFSNOKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 201000004792 malaria Diseases 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- QLBMKYCSDKNZAL-UHFFFAOYSA-N n-(4-chlorophenyl)-n-cyclopropyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(Cl)=CC=3)C=CN2N=C1 QLBMKYCSDKNZAL-UHFFFAOYSA-N 0.000 claims description 2
- YCWKWWREAWIMNT-UHFFFAOYSA-N n-(4-chlorophenyl)-n-cyclopropyl-3-[6-(methylcarbamoyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(Cl)=CC=3)C=CN2N=C1 YCWKWWREAWIMNT-UHFFFAOYSA-N 0.000 claims description 2
- RQUPCQCXFLJNEN-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(Cl)=CC=3)C=CN2N=C1 RQUPCQCXFLJNEN-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- RPJPDDLMNXIQOV-UHFFFAOYSA-N n-(4-chlorophenyl)-n-methyl-3-[6-(methylcarbamoyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(Cl)=CC=3)C=CN2N=C1 RPJPDDLMNXIQOV-UHFFFAOYSA-N 0.000 claims description 2
- IVSTYLJEZTVXAI-UHFFFAOYSA-N n-(4-cyanophenyl)-n-(2-hydroxyethyl)-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(CCO)C=3C=CC(=CC=3)C#N)C=CN2N=C1 IVSTYLJEZTVXAI-UHFFFAOYSA-N 0.000 claims description 2
- MVQRJMLNKDHGIF-UHFFFAOYSA-N n-(4-cyanophenyl)-n-(2-methoxyethyl)-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(CCOC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 MVQRJMLNKDHGIF-UHFFFAOYSA-N 0.000 claims description 2
- QHQWPRDOKMQBPX-UHFFFAOYSA-N n-(4-cyanophenyl)-n-[2-(dimethylamino)ethyl]-3-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=CC=1N(CCN(C)C)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(F)(F)F)C=C1 QHQWPRDOKMQBPX-UHFFFAOYSA-N 0.000 claims description 2
- RXTIWOYOWHYIAG-UHFFFAOYSA-N n-(4-cyanophenyl)-n-cyclobutyl-3-[6-(methylcarbamoyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CCC3)C=3C=CC(=CC=3)C#N)C=CN2N=C1 RXTIWOYOWHYIAG-UHFFFAOYSA-N 0.000 claims description 2
- JIIUPZKZQNHKJP-UHFFFAOYSA-N n-(4-cyanophenyl)-n-cyclopropyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(=CC=3)C#N)C=CN2N=C1 JIIUPZKZQNHKJP-UHFFFAOYSA-N 0.000 claims description 2
- BZAYVUAXBIQRQQ-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(1h-pyrazol-5-yl)phenyl]pyrazolo[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=2C(C=C1)=CC=C1C1=CC=NN1 BZAYVUAXBIQRQQ-UHFFFAOYSA-N 0.000 claims description 2
- NARYPCJDJASVKH-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C#N)C=CN2N=C1 NARYPCJDJASVKH-UHFFFAOYSA-N 0.000 claims description 2
- FUAXSFPIDJXYEF-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[4-(trifluoromethyl)phenyl]pyrazolo[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(F)(F)F)C=C1 FUAXSFPIDJXYEF-UHFFFAOYSA-N 0.000 claims description 2
- HSYFIBRVTQDCQH-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[5-(trifluoromethyl)pyridin-2-yl]pyrazolo[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(F)(F)F)C=N1 HSYFIBRVTQDCQH-UHFFFAOYSA-N 0.000 claims description 2
- FFXJDPAXCZHDGF-UHFFFAOYSA-N n-(4-cyanophenyl)-n-methyl-3-[6-(methylcarbamoyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C#N)C=CN2N=C1 FFXJDPAXCZHDGF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- OSWSESLZUZQSOP-UHFFFAOYSA-N n-(5-carbamoylpyridin-2-yl)-n-cyclopropyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C(N)=O)C=CN2N=C1 OSWSESLZUZQSOP-UHFFFAOYSA-N 0.000 claims description 2
- PNWVUEJZKSPMJI-UHFFFAOYSA-N n-(5-chloropyridin-2-yl)-n-cyclopropyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(Cl)=CC=3)C=CN2N=C1 PNWVUEJZKSPMJI-UHFFFAOYSA-N 0.000 claims description 2
- RRGXKLWHKMFJGY-UHFFFAOYSA-N n-(5-cyano-6-methoxypyridin-2-yl)-n-cyclopropyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=C(OC)C(C#N)=CC=3)C=CN2N=C1 RRGXKLWHKMFJGY-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- DCWOLPHZFUNUCT-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-[4-(2-hydroxyethylcarbamoyl)phenyl]-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(C(=O)NCCO)C=C1 DCWOLPHZFUNUCT-UHFFFAOYSA-N 0.000 claims description 2
- CZQAJWCLHUCGTB-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-[4-(methylcarbamoyl)phenyl]-n-(oxetan-3-yl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3COC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 CZQAJWCLHUCGTB-UHFFFAOYSA-N 0.000 claims description 2
- GGDDEXIVBFQSAN-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)NC=3N=CC(=CC=3)C#N)C=CN2N=C1 GGDDEXIVBFQSAN-UHFFFAOYSA-N 0.000 claims description 2
- YSFOYPLRLSUXGD-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-[4-[2-(dimethylamino)ethylcarbamoyl]phenyl]-n-methylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1=C2C=C(C(=O)N(C)C=3N=CC(=CC=3)C#N)C=CN2N=C1 YSFOYPLRLSUXGD-UHFFFAOYSA-N 0.000 claims description 2
- ZUHAYTHYUNRADF-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-3-[5-(methylcarbamoyl)pyridin-2-yl]-n-propan-2-ylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C(C)C)C=3N=CC(=CC=3)C#N)C=CN2N=C1 ZUHAYTHYUNRADF-UHFFFAOYSA-N 0.000 claims description 2
- UXEFDFKYPJBLAT-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-(cyclopropylmethyl)-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(CC3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 UXEFDFKYPJBLAT-UHFFFAOYSA-N 0.000 claims description 2
- KPXLMZFJOWIJLL-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-cyclobutyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CCC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 KPXLMZFJOWIJLL-UHFFFAOYSA-N 0.000 claims description 2
- MQLKMEHORCNIQH-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-cyclobutyl-3-[5-(methylcarbamoyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CCC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 MQLKMEHORCNIQH-UHFFFAOYSA-N 0.000 claims description 2
- MTOFAYNZWROOFL-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-cyclobutyl-3-[6-(methylcarbamoyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CCC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 MTOFAYNZWROOFL-UHFFFAOYSA-N 0.000 claims description 2
- KPMLXSCRXLUDRE-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-cyclopentyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CCCC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 KPMLXSCRXLUDRE-UHFFFAOYSA-N 0.000 claims description 2
- OWJZSPIQRDWDOQ-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-cyclopropyl-3-[4-(cyclopropylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C2=C3C=C(C=CN3N=C2)C(=O)N(C2CC2)C=2N=CC(=CC=2)C#N)C=CC=1C(=O)NC1CC1 OWJZSPIQRDWDOQ-UHFFFAOYSA-N 0.000 claims description 2
- SHBGMUKYDCLJBK-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-cyclopropyl-3-[4-(ethylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NCC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 SHBGMUKYDCLJBK-UHFFFAOYSA-N 0.000 claims description 2
- WYJFZJKZCSUHBX-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-cyclopropyl-3-[4-(oxetan-3-ylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C2=C3C=C(C=CN3N=C2)C(=O)N(C2CC2)C=2N=CC(=CC=2)C#N)C=CC=1C(=O)NC1COC1 WYJFZJKZCSUHBX-UHFFFAOYSA-N 0.000 claims description 2
- KFOMSSFVJIRHPU-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-cyclopropyl-3-[5-(methylcarbamoyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C#N)C=CN2N=C1 KFOMSSFVJIRHPU-UHFFFAOYSA-N 0.000 claims description 2
- LEWMNNNBKDRYRQ-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-ethyl-3-[4-(methylsulfamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(S(=O)(=O)NC)C=C1 LEWMNNNBKDRYRQ-UHFFFAOYSA-N 0.000 claims description 2
- UFYBPEINJLXMDB-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-ethyl-3-[6-(methylcarbamoyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)N=C1 UFYBPEINJLXMDB-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- RTWXRNVTDKFFAB-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-methyl-3-[4-(piperidin-4-ylcarbamoyl)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=2C(C=C1)=CC=C1C(=O)NC1CCNCC1 RTWXRNVTDKFFAB-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- CASVUIQEVGEGCP-UHFFFAOYSA-N n-(5-cyanopyridin-2-yl)-n-methyl-3-[5-(trifluoromethyl)pyridin-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(F)(F)F)C=N1 CASVUIQEVGEGCP-UHFFFAOYSA-N 0.000 claims description 2
- VHCNDWGSINHRFQ-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-n-methyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=NC(OC)=CC=3)C=CN2N=C1 VHCNDWGSINHRFQ-UHFFFAOYSA-N 0.000 claims description 2
- YPTLWTAKBWMQEP-UHFFFAOYSA-N n-[4-[5-[1-[methyl-(5-methylpyridin-2-yl)amino]ethyl]pyrazolo[1,5-a]pyridin-3-yl]phenyl]acetamide Chemical compound C1=CN2N=CC(C=3C=CC(NC(C)=O)=CC=3)=C2C=C1C(C)N(C)C1=CC=C(C)C=N1 YPTLWTAKBWMQEP-UHFFFAOYSA-N 0.000 claims description 2
- ANYOQUOLOWBNEU-UHFFFAOYSA-N n-[5-cyano-6-(2-hydroxyethoxy)pyridin-2-yl]-n-ethyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C#N)C(OCCO)=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)C=C1 ANYOQUOLOWBNEU-UHFFFAOYSA-N 0.000 claims description 2
- ZHYBQKPEVSYJBI-UHFFFAOYSA-N n-cyclobutyl-3-[4-(methylcarbamoyl)phenyl]-n-[5-(trifluoromethyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CCC3)C=3N=CC(=CC=3)C(F)(F)F)C=CN2N=C1 ZHYBQKPEVSYJBI-UHFFFAOYSA-N 0.000 claims description 2
- FWPHMGNLBGSHOU-UHFFFAOYSA-N n-cyclopropyl-3-[4-(methylcarbamoyl)phenyl]-n-(5-methylpyridin-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(C)=CC=3)C=CN2N=C1 FWPHMGNLBGSHOU-UHFFFAOYSA-N 0.000 claims description 2
- YIUYQVZGKNXGTF-UHFFFAOYSA-N n-cyclopropyl-3-[4-(methylcarbamoyl)phenyl]-n-[5-(trifluoromethyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(=CC=3)C(F)(F)F)C=CN2N=C1 YIUYQVZGKNXGTF-UHFFFAOYSA-N 0.000 claims description 2
- OJKLFHNVCKXTSV-UHFFFAOYSA-N n-cyclopropyl-n-(3,4-difluorophenyl)-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=C(F)C(F)=CC=3)C=CN2N=C1 OJKLFHNVCKXTSV-UHFFFAOYSA-N 0.000 claims description 2
- AIJSPOWXEMAGDY-UHFFFAOYSA-N n-cyclopropyl-n-(5-fluoropyridin-2-yl)-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3N=CC(F)=CC=3)C=CN2N=C1 AIJSPOWXEMAGDY-UHFFFAOYSA-N 0.000 claims description 2
- YAXCNOBBZZXYBG-UHFFFAOYSA-N n-ethyl-3-[6-(methylcarbamoyl)pyridin-3-yl]-n-[5-(trifluoromethyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)N=C1 YAXCNOBBZZXYBG-UHFFFAOYSA-N 0.000 claims description 2
- KGZDTZLJJQQLOM-UHFFFAOYSA-N n-ethyl-n-(5-fluoropyridin-2-yl)-3-[6-(methylcarbamoyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C=1C=C(F)C=NC=1N(CC)C(=O)C(=CC1=2)C=CN1N=CC=2C1=CC=C(C(=O)NC)N=C1 KGZDTZLJJQQLOM-UHFFFAOYSA-N 0.000 claims description 2
- ZTGKBOUPFXOCCR-UHFFFAOYSA-N n-methyl-3-[4-(methylcarbamoyl)phenyl]-n-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3C=CC(=CC=3)C(F)(F)F)C=CN2N=C1 ZTGKBOUPFXOCCR-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 235000005152 nicotinamide Nutrition 0.000 claims description 2
- 239000011570 nicotinamide Substances 0.000 claims description 2
- 229960003966 nicotinamide Drugs 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- FVWGFJJKVJWYFZ-UHFFFAOYSA-N C(N)(=O)C=1C=CC(=NC=1)C1=NN2C(C=C(C=C2)C(=O)N(C2CC2)C2=CC=C(C=C2)C#N)=C1 Chemical compound C(N)(=O)C=1C=CC(=NC=1)C1=NN2C(C=C(C=C2)C(=O)N(C2CC2)C2=CC=C(C=C2)C#N)=C1 FVWGFJJKVJWYFZ-UHFFFAOYSA-N 0.000 claims 1
- VUVNCQJGPFYCFY-UHFFFAOYSA-N N-[5-[(5-cyanopyridin-2-yl)-cyclopropylsulfamoyl]pyrazolo[1,5-a]pyridin-3-yl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC=1C=NN2C=1C=C(C=C2)S(N(C1CC1)C1=NC=C(C=C1)C#N)(=O)=O VUVNCQJGPFYCFY-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- DUMSENAXSREFPY-UHFFFAOYSA-N n-(4-cyanophenyl)-n-cyclopropyl-3-[5-(methylcarbamoyl)pyridin-2-yl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(=CC=3)C#N)C=CN2N=C1 DUMSENAXSREFPY-UHFFFAOYSA-N 0.000 claims 1
- MNWWEGIFDNKMNJ-UHFFFAOYSA-N n-[5-(2-aminoethoxy)pyridin-2-yl]-n-methyl-3-[4-(methylcarbamoyl)phenyl]pyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=C2C=C(C(=O)N(C)C=3N=CC(OCCN)=CC=3)C=CN2N=C1 MNWWEGIFDNKMNJ-UHFFFAOYSA-N 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- HUHVFOSBOVRBBB-UHFFFAOYSA-N 3-(5-carbamoylpyridin-2-yl)-n-(4-cyanophenyl)-n-cyclopropylpyrazolo[1,5-a]pyridine-5-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1C1=C2C=C(C(=O)N(C3CC3)C=3C=CC(=CC=3)C#N)C=CN2N=C1 HUHVFOSBOVRBBB-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261728018P | 2012-11-19 | 2012-11-19 | |
| US61/728,018 | 2012-11-19 | ||
| US201361847860P | 2013-07-18 | 2013-07-18 | |
| US61/847,860 | 2013-07-18 | ||
| PCT/US2013/070601 WO2014078802A1 (en) | 2012-11-19 | 2013-11-18 | Compounds and compositions for the treatment of parasitic diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016505529A JP2016505529A (ja) | 2016-02-25 |
| JP2016505529A5 true JP2016505529A5 (enExample) | 2017-01-05 |
| JP6298472B2 JP6298472B2 (ja) | 2018-03-20 |
Family
ID=49667630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015542882A Expired - Fee Related JP6298472B2 (ja) | 2012-11-19 | 2013-11-18 | 寄生虫病の処置のための化合物および組成物 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US9556169B2 (enExample) |
| EP (1) | EP2925757B1 (enExample) |
| JP (1) | JP6298472B2 (enExample) |
| CN (1) | CN105164124B (enExample) |
| AR (1) | AR093532A1 (enExample) |
| CY (1) | CY1119727T1 (enExample) |
| DK (1) | DK2925757T3 (enExample) |
| ES (1) | ES2655030T3 (enExample) |
| HR (1) | HRP20171998T1 (enExample) |
| HU (1) | HUE037600T2 (enExample) |
| LT (1) | LT2925757T (enExample) |
| ME (1) | ME03042B (enExample) |
| PL (1) | PL2925757T3 (enExample) |
| PT (1) | PT2925757T (enExample) |
| RS (1) | RS56720B1 (enExample) |
| SI (1) | SI2925757T1 (enExample) |
| TW (1) | TWI600654B (enExample) |
| UY (1) | UY35146A (enExample) |
| WO (1) | WO2014078802A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA41338B1 (fr) * | 2015-01-16 | 2019-07-31 | Hoffmann La Roche | Composés de pyrazine pour le traitement de maladies infectieuses |
| EA201891672A1 (ru) | 2016-01-21 | 2018-12-28 | Новартис Аг | Соединения и композиции для лечения криптоспоридиоза |
| AR108222A1 (es) * | 2016-05-05 | 2018-08-01 | Elanco Tiergesundheit Ag | Compuestos heteroaril-1,2,4-triazol y heteroaril-tetrazol |
| WO2018011163A1 (en) * | 2016-07-14 | 2018-01-18 | F. Hoffmann-La Roche Ag | 6,7-dihydro-4h-pyrazolo[1,5-a]pyrazine and 6,7-dihydro-4h-triazolo[1,5-a]pyrazine compounds for the treatment of infectious diseases |
| CN110023312A (zh) * | 2016-10-13 | 2019-07-16 | 由卫生与公众服务部部长代表的美利坚合众国 | 阻止疟疾寄生虫传播的化合物和方法 |
| US10961261B2 (en) | 2017-03-01 | 2021-03-30 | Anacor Pharmaceuticals, Inc. | Oxaborole analogs and uses thereof |
| AU2018240031B2 (en) * | 2017-03-20 | 2022-07-14 | President And Fellows Of Harvard College | Compounds and methods for the treatment of parasitic diseases |
| CN117105827A (zh) | 2017-03-27 | 2023-11-24 | 魁北克电力公司 | 用于电解质组合物中或用作电极添加剂的盐 |
| CN107037148B (zh) * | 2017-04-07 | 2019-11-19 | 上海药明康德新药开发有限公司 | 卤泛曲林的高效液相检测方法 |
| JOP20190278A1 (ar) | 2017-05-31 | 2019-11-28 | Novartis Ag | مركبات 5، 6-ثنائية الحلقة مندمجة وتركيبات لعلاج الأمراض الطفيلية |
| US11628593B2 (en) | 2017-10-02 | 2023-04-18 | Dal-Tile, Llc | Method for manufacturing an engineered stone and an engineered stone |
| MX2021000293A (es) * | 2018-07-09 | 2021-07-15 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos heterociclicos antihelminticos. |
| GB201811695D0 (en) * | 2018-07-17 | 2018-08-29 | Salvensis | Compounds for use in the treatment of fascioliasis |
| AR117788A1 (es) * | 2019-01-14 | 2021-08-25 | Pi Industries Ltd | Compuestos de fenilamidina 3-sustituida, preparación y uso |
| KR20220002890A (ko) | 2019-03-19 | 2022-01-07 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 아자-벤조티오펜 및 아자-벤조푸란 화합물 |
| US20200385398A1 (en) | 2019-06-07 | 2020-12-10 | Elanco Tiergesundheit Ag | New bicyclic derivatives |
| WO2023061838A1 (en) * | 2021-10-14 | 2023-04-20 | Syngenta Crop Protection Ag | Imidazo[1,2-a]pyridine derivatives |
| RU2019123849A (ru) * | 2019-07-29 | 2021-02-01 | Дзе Брихэм Энд Уимен`З Хоспитал, Инк. | Ингибиторы фактора ингибирования миграции макрофагов |
| BR112022024156A2 (pt) | 2020-05-29 | 2023-02-14 | Boehringer Ingelheim Animal Health Usa Inc | Compostos heterocílicos antelmínticos |
| PY2189412A (es) * | 2020-10-14 | 2022-05-17 | Novartis Ag | Compuestos y composiciones para el tratamiento de la criptosporidiosis |
| WO2023275590A1 (en) | 2021-06-29 | 2023-01-05 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Detection of phosphoinositides in blood cells as a biomarker for alpha synuclein associated pathologies and a method of treatment of parkinson's disease and the related neurodegenerations |
| US20250002491A1 (en) | 2021-10-04 | 2025-01-02 | Forx Therapeutics Ag | N,n-dimethyl-4-(7-(n-(1-methylcyclopropyl)sulfamoyl)-imidazo[1,5-a]pyridin-5-yl)piperazine-1-carboxamide derivatives and the corresponding pyrazolo[1,5-a]pyridine derivatives as parg inhibitors for the treatment of cancer |
| WO2023073641A1 (en) | 2021-11-01 | 2023-05-04 | Boehringer Ingelheim Vetmedica Gmbh | Anthelmintic pyrrolopyridazine compounds |
| CA3181279A1 (en) * | 2022-03-24 | 2023-09-24 | Bloom Energy Corporation | Fuel cell stack assembly including heat sink inserts |
| US12358305B2 (en) | 2022-06-30 | 2025-07-15 | Dal-Tile, Llc | Method for manufacturing a decorative element comprising an engineered stone and a decorative element comprising an engineered stone |
| US12338188B2 (en) | 2022-06-30 | 2025-06-24 | Dal-Tile, Llc | Method for manufacturing a decorative element comprising an engineered stone and a decorative element comprising an engineered stone |
| US20250388603A1 (en) * | 2022-07-01 | 2025-12-25 | The Scripps Research Institute | Antimalarial compounds |
| US20240124450A1 (en) | 2022-09-21 | 2024-04-18 | Pfizer Inc. | Novel SIK Inhibitors |
| WO2024196989A1 (en) * | 2023-03-20 | 2024-09-26 | University Of Central Florida Research Foundation, Inc. | Anti-malarial therapy |
| AR132354A1 (es) * | 2023-04-13 | 2025-06-18 | Syngenta Crop Protection Ag | Derivados de pirazolo[1,5-a]piridina |
| EP4667535A1 (en) | 2024-06-17 | 2025-12-24 | SilOriX GmbH | Nonlinear optical dyes with improved stability |
Family Cites Families (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5348396A (en) | 1995-05-01 | 1996-11-21 | Fujisawa Pharmaceutical Co., Ltd. | Imidazo 1,2-a pyridine and imidazo 1,2-a pyridezine derivati ves and their use as bone resorption inhibitors |
| AU747708B2 (en) | 1996-07-24 | 2002-05-23 | Du Pont Pharmaceuticals Company | Azolo triazines and pyrimidines |
| WO1999000372A1 (fr) | 1997-06-27 | 1999-01-07 | Fujisawa Pharmaceutical Co., Ltd. | Sulfamides et leur utilisation medicale |
| JP2001139575A (ja) | 1999-11-15 | 2001-05-22 | Fujisawa Pharmaceut Co Ltd | 新規ピラゾロピリジン誘導体 |
| GB0002312D0 (en) | 2000-02-01 | 2000-03-22 | Glaxo Group Ltd | Medicaments |
| GB0002336D0 (en) | 2000-02-01 | 2000-03-22 | Glaxo Group Ltd | Medicaments |
| CA2397661C (en) * | 2000-03-01 | 2012-01-03 | Janssen Pharmaceutica N.V. | 2,4-disubstituted thiazolyl derivatives |
| ES2222372T3 (es) | 2000-04-28 | 2005-02-01 | Glaxo Group Limited | Procedimiento de preparacion de derivados de pirazolopiridina. |
| GB0018473D0 (en) | 2000-07-27 | 2000-09-13 | Merck Sharp & Dohme | Therapeutic agents |
| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| AUPQ969800A0 (en) | 2000-08-28 | 2000-09-21 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| EP1217000A1 (en) | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| EP2048142A3 (en) | 2001-04-26 | 2009-04-22 | Eisai R&D Management Co., Ltd. | Nitrogen-containing condensed cyclic compound having a pyrazolyl group as a substituent group and pharmaceutical composition thereof |
| AUPR916301A0 (en) | 2001-11-29 | 2001-12-20 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| CA2483306A1 (en) | 2002-04-23 | 2003-11-06 | Shionogi & Co., Ltd. | Pyrazolo[1,5-a]pyrimidine derivative and nad(p)h oxidase inhibitor containing the same |
| US7119200B2 (en) | 2002-09-04 | 2006-10-10 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US8673924B2 (en) | 2002-09-04 | 2014-03-18 | Merck Sharp & Dohme Corp. | Substituted pyrazolo[1,5-a]pyrimidines as cyclin dependent kinase inhibitors |
| WO2004026871A1 (en) | 2002-09-17 | 2004-04-01 | Eli Lilly And Company | Novel pyrazolopyridine derivatves as pharmaceutical agents |
| US7329658B2 (en) | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US7176210B2 (en) | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7504424B2 (en) | 2004-07-16 | 2009-03-17 | Schering Corporation | Compounds for the treatment of inflammatory disorders |
| DE602005023172D1 (de) * | 2004-07-16 | 2010-10-07 | Schering Corp | Hydantoinderivate zur behandlung von entzündlichen erkrankungen |
| US7488745B2 (en) * | 2004-07-16 | 2009-02-10 | Schering Corporation | Compounds for the treatment of inflammatory disorders |
| MX2007001399A (es) | 2004-08-02 | 2007-04-18 | Osi Pharm Inc | Compuestos que inhiben pirrolopirimidina multi-cinasa aril-amino sustituidas. |
| AU2005295734A1 (en) | 2004-10-15 | 2006-04-27 | Biogen Idec Ma Inc. | Methods of treating vascular injuries |
| WO2006049339A1 (ja) | 2004-11-08 | 2006-05-11 | Banyu Pharmaceutical Co., Ltd. | 新規縮環イミダゾール誘導体 |
| WO2006068826A2 (en) * | 2004-12-21 | 2006-06-29 | Smithkline Beecham Corporation | 2-pyrimidinyl pyrazolopyridine erbb kinase inhibitors |
| JPWO2006070943A1 (ja) | 2004-12-28 | 2008-06-12 | 武田薬品工業株式会社 | 縮合イミダゾール化合物およびその用途 |
| US7713975B1 (en) | 2005-01-12 | 2010-05-11 | Alcon, Inc. | 3,6-substituted imidazol[1,2-b]pyridazine analogs for treating allergic and inflammatory diseases |
| US20100216798A1 (en) | 2005-07-29 | 2010-08-26 | Astellas Pharma Inc | Fused heterocycles as lck inhibitors |
| US20070049591A1 (en) | 2005-08-25 | 2007-03-01 | Kalypsys, Inc. | Inhibitors of MAPK/Erk Kinase |
| EP1928237A4 (en) | 2005-09-02 | 2011-03-09 | Abbott Lab | NEW HETEROCYCLES BASED ON IMIDAZO |
| DE102005042742A1 (de) | 2005-09-02 | 2007-03-08 | Schering Ag | Substituierte Imidazo[1,2b]pyridazine als Kinase-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
| RU2405770C2 (ru) | 2005-09-27 | 2010-12-10 | Сионоги Энд Ко., Лтд. | Производное сульфонамида, обладающее антагонистической активностью в отношении рецептора pgd2 |
| WO2007067537A1 (en) | 2005-12-07 | 2007-06-14 | Osi Pharmaceuticals, Inc. | Pyrrolopyridine kinase inhibiting compounds |
| US7795273B2 (en) | 2005-12-08 | 2010-09-14 | Novartis Ag | Pyrazolo[1,5-a]pyridine-3-carboxylic acids as EphB and VEGFR2 kinase inhibitors |
| WO2007086080A2 (en) | 2006-01-30 | 2007-08-02 | Glenmark Pharmaceuticals Limited | NOVEL IMIDAZO[1,2-a]PYRIDINE CANNABINOID RECEPTOR LIGANDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| WO2007100775A2 (en) | 2006-02-27 | 2007-09-07 | Alexander Michalow | Methods for regulating neurotransmitter systems by inducing counteradaptations |
| WO2007096764A2 (en) | 2006-02-27 | 2007-08-30 | Glenmark Pharmaceuticals S.A. | Bicyclic heteroaryl derivatives as cannabinoid receptor modulators |
| JP5352452B2 (ja) | 2006-06-06 | 2013-11-27 | メディシノバ， インコーポレイテッド | 置換ピラゾロ［１，５−ａ］ピリジン化合物およびその使用方法 |
| DE102006029447A1 (de) | 2006-06-21 | 2007-12-27 | Bayer Schering Pharma Ag | Oxo-substituierte Imidazo[1,2b]pyridazine, deren Herstellung und Verwendung als Arzneimittel |
| EP1873157A1 (en) | 2006-06-21 | 2008-01-02 | Bayer Schering Pharma Aktiengesellschaft | Pyrazolopyrimidines and salts thereof, pharmaceutical compositions comprising same, methods of preparing same and uses of same |
| EP1900739A1 (en) | 2006-08-30 | 2008-03-19 | Cellzome Ag | Diazolodiazine derivatives as kinase inhibitors |
| CN101594909A (zh) | 2006-09-07 | 2009-12-02 | 比奥根艾迪克Ma公司 | 用于治疗炎性病症、细胞增殖性失调、免疫失调的irak调节剂 |
| EP2270229A1 (en) | 2006-09-12 | 2011-01-05 | The General Hospital Corporation | Inhibitors of bone morphogenetic protein (BMP) signalling for therapeutical purposes |
| JP2010504933A (ja) | 2006-09-29 | 2010-02-18 | ノバルティス アーゲー | Ｐｉ３ｋ脂質キナーゼ阻害剤としてのピラゾロピリミジン |
| BRPI0718266A2 (pt) | 2006-10-30 | 2014-01-07 | Novartis Ag | Compostos heterocíclicos como agentes anti-inflamatórios. |
| US7750007B2 (en) | 2006-11-06 | 2010-07-06 | Supergen, Inc. | Imidazo[1,2-beta]pyridazine and pyrazolo[1,5-alpha]pyrimidine derivatives and their use as protein kinase inhibitors |
| WO2008072682A1 (ja) | 2006-12-15 | 2008-06-19 | Daiichi Sankyo Company, Limited | イミダゾ［１，２－ｂ］ピリダジン誘導体 |
| AR064420A1 (es) | 2006-12-21 | 2009-04-01 | Alcon Mfg Ltd | Composiciones farmaceuticas oftalmicas que comprenden una cantidad efectiva de analogos de 6-aminoimidazo[1,2b]piridazinas, utiles para el tratamiento del glaucoma y/o controlar la presion intraocular normal o elevada(iop). |
| CN101679408B (zh) | 2006-12-22 | 2016-04-27 | Astex治疗学有限公司 | 作为fgfr抑制剂的双环杂环化合物 |
| CA2676138A1 (en) | 2007-01-26 | 2008-08-07 | Irm Llc | Compounds and compositions as kinase inhibitors |
| JP2010531304A (ja) | 2007-06-18 | 2010-09-24 | ユニバーシティ オブ ルイビル リサーチ ファウンデーション、インコーポレイテッド | 抗悪性腫瘍活性を有するｐｆｋｆｂ３阻害物質ファミリー |
| US20100226881A1 (en) | 2007-07-11 | 2010-09-09 | Auckland Uniservices Limited | PYRAZOLO[1,5-a]PYRIDINES AND THEIR USE IN CANCER THERAPY |
| CN101711245B (zh) | 2007-07-19 | 2015-03-25 | H.隆德贝克有限公司 | 5元杂环酰胺及相关的化合物 |
| WO2009017954A1 (en) | 2007-08-01 | 2009-02-05 | Phenomix Corporation | Inhibitors of jak2 kinase |
| PE20091468A1 (es) | 2008-02-28 | 2009-10-22 | Novartis Ag | DERIVADOS DE 3-METIL-IMIDAZO-[1,2-b]-PIRIDAZINA |
| EP2265603B1 (en) | 2008-03-13 | 2014-05-07 | The General Hospital Corporation | Inhibitors of the bmp signaling pathway |
| CA2722418C (en) | 2008-05-13 | 2013-09-17 | Irm Llc | Fused nitrogen containing heterocycles and compositions thereof as kinase inhibitors |
| JP2009298710A (ja) | 2008-06-11 | 2009-12-24 | Daiichi Sankyo Co Ltd | イミダゾ［１，２−ｂ］ピリダジン誘導体含有医薬組成物 |
| CA2729121C (en) | 2008-06-30 | 2019-04-09 | Centocor Ortho Biotech Inc. | Differentiation of pluripotent stem cells |
| CA2732520A1 (en) | 2008-08-05 | 2010-02-11 | Merck Sharp & Dohme Corp. | Therapeutic compounds |
| WO2010017046A1 (en) | 2008-08-05 | 2010-02-11 | Merck & Co., Inc. | Pyrazolo[1,5-a]pyridines as mark inhibitors |
| US8293909B2 (en) | 2008-09-11 | 2012-10-23 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| US8198449B2 (en) | 2008-09-11 | 2012-06-12 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
| ES2710701T3 (es) * | 2008-09-24 | 2019-04-26 | Basf Se | Compuestos de pirazol para el control de plagas de invertebrados |
| WO2010059836A1 (en) | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Substituted aza-bridged bicyclics for cardiovascular and cns disease |
| ES2403633T3 (es) | 2008-12-04 | 2013-05-20 | Proximagen Limited | Compuestos de imidazopiridina |
| WO2010074586A1 (en) | 2008-12-23 | 2010-07-01 | Pathway Therapeutics Limited | Pyrazolo[1,5-a]pyridine and imidazo[1,2-a]pyridine derivatives and their use in cancer therapy |
| JP2012516329A (ja) * | 2009-01-30 | 2012-07-19 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | Ｐｉ３ｋ阻害剤としてのヘテロアリールおよびその使用 |
| US8969342B2 (en) | 2009-03-20 | 2015-03-03 | Brandeis University | Compounds and methods for treating mammalian gastrointestinal microbial infections |
| CA2755285C (en) | 2009-03-20 | 2014-02-11 | Yunxin Y. Bo | Inhibitors of pi3 kinase |
| WO2010117787A2 (en) | 2009-03-30 | 2010-10-14 | The Brigham And Women's Hospital, Inc. | Inhibiting eph b-3 kinase |
| WO2010118207A1 (en) | 2009-04-09 | 2010-10-14 | Schering Corporation | Pyrazolo [1, 5-a] pyrimidine derivatives as mtor inhibitors |
| UY32776A (es) | 2009-07-09 | 2011-02-28 | Irm Llc | Compuestos de imidazopirazinas sustituidas para el tratamiento de enfermedades parasitarias,composiciones farmacéuticas que los contienen y aplicación. |
| RU2421455C2 (ru) | 2009-07-14 | 2011-06-20 | Государственное образовательное учреждение высшего профессионального образования "Пермский государственный университет" | СПОСОБ ПОЛУЧЕНИЯ МЕТИЛ 7-АРИЛКАРБАМОИЛ-6-БЕНЗОИЛ-2-МЕТИЛ-3-ФЕНИЛПИРАЗОЛО[1,5-a]ПИРИМИДИН-5-КАРБОКСИЛАТОВ |
| TW201107329A (en) | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
| US8865726B2 (en) | 2009-09-03 | 2014-10-21 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyrimidine compounds as mTOR inhibitors |
| WO2011038097A2 (en) | 2009-09-23 | 2011-03-31 | Amira Pharmaceuticals, Inc. | Indolizine inhibitors of 5-lipoxygenase |
| GB201002911D0 (en) | 2010-02-19 | 2010-04-07 | Medical Res Council | Compound |
| JP2016500073A (ja) | 2012-11-19 | 2016-01-07 | ノバルティス アーゲー | 寄生虫病の処置のための化合物および組成物 |
-
2013
- 2013-11-18 LT LTEP13795977.1T patent/LT2925757T/lt unknown
- 2013-11-18 TW TW102141950A patent/TWI600654B/zh not_active IP Right Cessation
- 2013-11-18 US US14/443,609 patent/US9556169B2/en not_active Expired - Fee Related
- 2013-11-18 HU HUE13795977A patent/HUE037600T2/hu unknown
- 2013-11-18 JP JP2015542882A patent/JP6298472B2/ja not_active Expired - Fee Related
- 2013-11-18 PT PT137959771T patent/PT2925757T/pt unknown
- 2013-11-18 WO PCT/US2013/070601 patent/WO2014078802A1/en not_active Ceased
- 2013-11-18 PL PL13795977T patent/PL2925757T3/pl unknown
- 2013-11-18 EP EP13795977.1A patent/EP2925757B1/en active Active
- 2013-11-18 CN CN201380070822.0A patent/CN105164124B/zh not_active Expired - Fee Related
- 2013-11-18 SI SI201330889T patent/SI2925757T1/en unknown
- 2013-11-18 HR HRP20171998TT patent/HRP20171998T1/hr unknown
- 2013-11-18 RS RS20171296A patent/RS56720B1/sr unknown
- 2013-11-18 DK DK13795977.1T patent/DK2925757T3/en active
- 2013-11-18 ME MEP-2017-266A patent/ME03042B/me unknown
- 2013-11-18 ES ES13795977.1T patent/ES2655030T3/es active Active
- 2013-11-19 UY UY0001035146A patent/UY35146A/es unknown
- 2013-11-19 AR ARP130104250A patent/AR093532A1/es unknown
-
2016
- 2016-07-26 US US15/220,149 patent/US9926314B2/en not_active Expired - Fee Related
-
2018
- 2018-01-03 CY CY20181100008T patent/CY1119727T1/el unknown
- 2018-02-06 US US15/889,578 patent/US20180230145A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SI2925757T1 (en) | Compounds and compositions for the treatment of parasitic diseases | |
| US9649309B2 (en) | Therapeutic uses of selected pyrimidine compounds with anti-Mer tyrosine kinase activity | |
| RU2018130069A (ru) | Соединения и композиции для лечения криптоспоридиоза | |
| RU2650895C2 (ru) | Соединения замещенных пиразолонов и способы использования | |
| US8188113B2 (en) | Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases | |
| US8664230B2 (en) | Pyridopyrimidine derivatives and use thereof | |
| US20240034723A1 (en) | Piperidinyl small molecule degraders of helios and methods of use | |
| PT764166E (pt) | Antagonistas de factor de libertacao de corticotropina | |
| US20210379056A1 (en) | Substituted pyrazole fused ring derivative, preparation method therefor, and application thereof | |
| BR112012017713A2 (pt) | Aminopiridina, formulação farmacêutica, processo para a preparação de um derivado de aminopiridina, intermediário, e, uso de uma aminopiridina ou de uma formulação farmacêutica | |
| JP2000302693A (ja) | 突然死予防のためのコルチコトロピン放出因子アンタゴニスト | |
| JP2017505794A5 (enExample) | ||
| RU2018138050A (ru) | Производные тиазолопиридина как агонисты gpr119 | |
| SG182713A1 (en) | Pyrazole derivatives as jak inhibitors | |
| KR20010050223A (ko) | Ｃｒｆ 길항제 및 관련 조성물의 용도 | |
| ES2598830T3 (es) | Compuestos bicíclicos o sales de los mismos para el uso en el tratamiento del cáncer | |
| EP3274344A1 (en) | Formylated n-heterocyclic derivatives as fgfr4 inhibitors | |
| IL297332B1 (en) | Quinoline compounds and preparations for inhibiting ezh2 | |
| WO2014020041A1 (en) | Combinations for the treatment of cancer | |
| US9422298B2 (en) | Pyridopyrimidine derivatives and use thereof | |
| RU2404776C2 (ru) | ПРИМЕНЕНИЕ ПИРИМИДИЛАМИНОБЕНЗАМИДОВ ДЛЯ ЛЕЧЕНИЯ ЗАБОЛЕВАНИЙ, ЧУВСТВИТЕЛЬНЫХ К МОДУЛЯЦИИ АКТИВНОСТИ КИНАЗЫ Тie-2 | |
| RU2025103592A (ru) | Гетероарильные производные в качестве ингибиторов ddr | |
| RU2023127302A (ru) | Производные индолина, как ингибиторы ddr | |
| JP2023528310A5 (enExample) | ||
| HK1245640B (en) | Agent for alleviating adverse reaction to antitumor drug |