JP2015500318A5 - - Google Patents
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- JP2015500318A5 JP2015500318A5 JP2014546500A JP2014546500A JP2015500318A5 JP 2015500318 A5 JP2015500318 A5 JP 2015500318A5 JP 2014546500 A JP2014546500 A JP 2014546500A JP 2014546500 A JP2014546500 A JP 2014546500A JP 2015500318 A5 JP2015500318 A5 JP 2015500318A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- phenyl
- pyridin
- trifluoromethyl
- methyl
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- -1 Dimethyl [3- (1-methyl-3-phenyl-4-trifluoromethyl-1H-pyrazolo [3,4-b] pyridin-6-yl) phenyl] amine Chemical class 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 208000002780 macular degeneration Diseases 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- DFHSASWXWBUERM-UHFFFAOYSA-N 1-methyl-3-phenyl-6-(6-pyrrolidin-1-ylpyridin-3-yl)-4-(trifluoromethyl)pyrazolo[3,4-b]pyridine Chemical compound C12=C(C(F)(F)F)C=C(C=3C=NC(=CC=3)N3CCCC3)N=C2N(C)N=C1C1=CC=CC=C1 DFHSASWXWBUERM-UHFFFAOYSA-N 0.000 claims 2
- AMDQRIBWSYJGCS-UHFFFAOYSA-N 2-fluoro-5-[3-phenyl-4-(trifluoromethyl)-2h-pyrazolo[3,4-b]pyridin-6-yl]benzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(C2=NC3=NNC(=C3C(=C2)C(F)(F)F)C=2C=CC=CC=2)=C1 AMDQRIBWSYJGCS-UHFFFAOYSA-N 0.000 claims 2
- FHCZUTUTTZWVGY-UHFFFAOYSA-N 3-[(4-fluorophenyl)methyl]-1-methyl-6-[1-(1-methylpyrazol-4-yl)imidazo[1,5-a]pyridine-3-carbonyl]quinazoline-2,4-dione Chemical compound C1=NN(C)C=C1C1=C2C=CC=CN2C(C(=O)C=2C=C3C(=O)N(CC=4C=CC(F)=CC=4)C(=O)N(C)C3=CC=2)=N1 FHCZUTUTTZWVGY-UHFFFAOYSA-N 0.000 claims 2
- JFBYMYUTFVTRGH-UHFFFAOYSA-N 4-[5-[1-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]pyridin-2-yl]morpholine Chemical compound C12=C(C(F)(F)F)C=C(C=3C=NC(=CC=3)N3CCOCC3)N=C2N(C)N=C1C1=CC=CC=C1 JFBYMYUTFVTRGH-UHFFFAOYSA-N 0.000 claims 2
- XDMHMPLVHGTYKS-UHFFFAOYSA-N 5-[1-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]-1,3-benzothiazole Chemical compound C12=C(C(F)(F)F)C=C(C=3C=C4N=CSC4=CC=3)N=C2N(C)N=C1C1=CC=CC=C1 XDMHMPLVHGTYKS-UHFFFAOYSA-N 0.000 claims 2
- DSPWIUQCFYIXHH-UHFFFAOYSA-N 5-[1-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]pyridine-3-carbonitrile Chemical compound C12=C(C(F)(F)F)C=C(C=3C=C(C=NC=3)C#N)N=C2N(C)N=C1C1=CC=CC=C1 DSPWIUQCFYIXHH-UHFFFAOYSA-N 0.000 claims 2
- AJEVIKZWKGEOMV-UHFFFAOYSA-N 6-(4-amino-3-cyanophenyl)-3-phenyl-2h-pyrazolo[3,4-b]pyridine-4-carboxamide Chemical compound C=12C(C(=O)N)=CC(C=3C=C(C(N)=CC=3)C#N)=NC2=NNC=1C1=CC=CC=C1 AJEVIKZWKGEOMV-UHFFFAOYSA-N 0.000 claims 2
- LSXFEXSCCOKTJP-UHFFFAOYSA-N 6-(4-amino-3-methoxyphenyl)-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid Chemical compound C1=C(N)C(OC)=CC(C=2N=C3NN=CC3=C(C(O)=O)C=2)=C1 LSXFEXSCCOKTJP-UHFFFAOYSA-N 0.000 claims 2
- IZNNHNMWHCIARM-UHFFFAOYSA-N 6-(4-methoxyphenyl)-1-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=CC(C(F)(F)F)=C(C(=NN2C)C=3C=CC=CC=3)C2=N1 IZNNHNMWHCIARM-UHFFFAOYSA-N 0.000 claims 2
- 206010008723 Chondrodystrophy Diseases 0.000 claims 2
- 206010058314 Dysplasia Diseases 0.000 claims 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims 2
- 208000008919 achondroplasia Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 230000001093 anti-cancer Effects 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 238000001959 radiotherapy Methods 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- RCYIXDDOGWGJPF-UHFFFAOYSA-N 1-methyl-6-(1-methylindol-6-yl)-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridine Chemical compound C1=C2N(C)C=CC2=CC=C1C(N=C1N(C)N=2)=CC(C(F)(F)F)=C1C=2C1=CC=CC=C1 RCYIXDDOGWGJPF-UHFFFAOYSA-N 0.000 claims 1
- WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims 1
- XOSOGXBIOFBORT-UHFFFAOYSA-N 2-amino-5-(4-carbamoyl-3-phenyl-2h-pyrazolo[3,4-b]pyridin-6-yl)benzoic acid Chemical compound C=12C(C(=O)N)=CC(C=3C=C(C(N)=CC=3)C(O)=O)=NC2=NNC=1C1=CC=CC=C1 XOSOGXBIOFBORT-UHFFFAOYSA-N 0.000 claims 1
- GMKXEDORCMRUFI-UHFFFAOYSA-N 2-amino-5-[1-[2-(dimethylamino)ethyl]-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C12=C(C(F)(F)F)C=C(C=3C=C(C(N)=CC=3)C#N)N=C2N(CCN(C)C)N=C1C1=CC=CC=C1 GMKXEDORCMRUFI-UHFFFAOYSA-N 0.000 claims 1
- JPVKYLFVOVPWQH-UHFFFAOYSA-N 2-amino-5-[1-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C12=C(C(F)(F)F)C=C(C=3C=C(C(N)=CC=3)C#N)N=C2N(C)N=C1C1=CC=CC=C1 JPVKYLFVOVPWQH-UHFFFAOYSA-N 0.000 claims 1
- CSGPKHRAQBZQJH-UHFFFAOYSA-N 2-amino-5-[1-methyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound N1=C2N(C)N=CC2=C(C(F)(F)F)C=C1C1=CC=C(N)C(C#N)=C1 CSGPKHRAQBZQJH-UHFFFAOYSA-N 0.000 claims 1
- SMJZQFYSNBKWNB-UHFFFAOYSA-N 2-amino-5-[2-(2-morpholin-4-ylethyl)-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C1=NC2=NN(CCN3CCOCC3)C(C=3C=CC=CC=3)=C2C(C(F)(F)F)=C1 SMJZQFYSNBKWNB-UHFFFAOYSA-N 0.000 claims 1
- JPTDSMDQPJAMRJ-UHFFFAOYSA-N 2-amino-5-[2-[2-(dimethylamino)ethyl]-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound CN(C)CCN1N=C2N=C(C=3C=C(C(N)=CC=3)C#N)C=C(C(F)(F)F)C2=C1C1=CC=CC=C1 JPTDSMDQPJAMRJ-UHFFFAOYSA-N 0.000 claims 1
- JBSIZWAQPWXKQM-UHFFFAOYSA-N 2-amino-5-[2-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound CN1N=C2N=C(C=3C=C(C(N)=CC=3)C#N)C=C(C(F)(F)F)C2=C1C1=CC=CC=C1 JBSIZWAQPWXKQM-UHFFFAOYSA-N 0.000 claims 1
- BGIGGPFBWVZHJH-UHFFFAOYSA-N 2-amino-5-[2-methyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound N=1C2=NN(C)C=C2C(C(F)(F)F)=CC=1C1=CC=C(N)C(C#N)=C1 BGIGGPFBWVZHJH-UHFFFAOYSA-N 0.000 claims 1
- NFGYWROCYCJOKS-UHFFFAOYSA-N 2-amino-5-[2-propyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound N=1C2=NN(CCC)C=C2C(C(F)(F)F)=CC=1C1=CC=C(N)C(C#N)=C1 NFGYWROCYCJOKS-UHFFFAOYSA-N 0.000 claims 1
- LNEHBXOQQBNSLL-UHFFFAOYSA-N 2-amino-5-[3-phenyl-1-(2-piperidin-1-ylethyl)-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C1=CC(C(F)(F)F)=C(C(=NN2CCN3CCCCC3)C=3C=CC=CC=3)C2=N1 LNEHBXOQQBNSLL-UHFFFAOYSA-N 0.000 claims 1
- KLDVAJKKZWYYRY-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-1-[2-(dimethylamino)ethyl]-3-phenylpyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C12=C(C(F)F)C=C(C=3C=C(C(N)=CC=3)C#N)N=C2N(CCN(C)C)N=C1C1=CC=CC=C1 KLDVAJKKZWYYRY-UHFFFAOYSA-N 0.000 claims 1
- HHDGPODQTCUIOS-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-1-methyl-3-phenylpyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C12=C(C(F)F)C=C(C=3C=C(C(N)=CC=3)C#N)N=C2N(C)N=C1C1=CC=CC=C1 HHDGPODQTCUIOS-UHFFFAOYSA-N 0.000 claims 1
- YUVBHWNSSUFVNU-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-1-methylpyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound N1=C2N(C)N=CC2=C(C(F)F)C=C1C1=CC=C(N)C(C#N)=C1 YUVBHWNSSUFVNU-UHFFFAOYSA-N 0.000 claims 1
- FNPZYDSGVUZXLM-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-1h-pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C1=CC(C(F)F)=C(C=NN2)C2=N1 FNPZYDSGVUZXLM-UHFFFAOYSA-N 0.000 claims 1
- XXCRAPLGDPCKJJ-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-2-(2-morpholin-4-ylethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C1=NC2=NN(CCN3CCOCC3)C=C2C(C(F)F)=C1 XXCRAPLGDPCKJJ-UHFFFAOYSA-N 0.000 claims 1
- MDYSIIMEKMVHHV-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-2-(2-piperidin-1-ylethyl)pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C1=NC2=NN(CCN3CCCCC3)C=C2C(C(F)F)=C1 MDYSIIMEKMVHHV-UHFFFAOYSA-N 0.000 claims 1
- MEKMQPABXWICTH-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-2-[2-(dimethylamino)ethyl]pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound N=1C2=NN(CCN(C)C)C=C2C(C(F)F)=CC=1C1=CC=C(N)C(C#N)=C1 MEKMQPABXWICTH-UHFFFAOYSA-N 0.000 claims 1
- YAFNWAKOZSULDC-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-2-methylpyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound N=1C2=NN(C)C=C2C(C(F)F)=CC=1C1=CC=C(N)C(C#N)=C1 YAFNWAKOZSULDC-UHFFFAOYSA-N 0.000 claims 1
- ILLSXUWLZFVSJX-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-2-propylpyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound N=1C2=NN(CCC)C=C2C(C(F)F)=CC=1C1=CC=C(N)C(C#N)=C1 ILLSXUWLZFVSJX-UHFFFAOYSA-N 0.000 claims 1
- LSQBKKRJDRKJBO-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-3-(3-methoxyphenyl)-2h-pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound COC1=CC=CC(C2=C3C(C(F)F)=CC(=NC3=NN2)C=2C=C(C(N)=CC=2)C#N)=C1 LSQBKKRJDRKJBO-UHFFFAOYSA-N 0.000 claims 1
- VKWZUFALKQADSU-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-3-phenyl-2h-pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C1=NC2=NNC(C=3C=CC=CC=3)=C2C(C(F)F)=C1 VKWZUFALKQADSU-UHFFFAOYSA-N 0.000 claims 1
- DWABMVLEQVWTKJ-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-3-pyridin-3-yl-2h-pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C1=NC2=NNC(C=3C=NC=CC=3)=C2C(C(F)F)=C1 DWABMVLEQVWTKJ-UHFFFAOYSA-N 0.000 claims 1
- GLPCZNDTNRZVSL-UHFFFAOYSA-N 2-amino-5-[4-(difluoromethyl)-3-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C1=NC2=NNC(C=3C=CN=CC=3)=C2C(C(F)F)=C1 GLPCZNDTNRZVSL-UHFFFAOYSA-N 0.000 claims 1
- RTTWSBORQZUXRB-UHFFFAOYSA-N 2-fluoro-5-[1-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]benzoic acid Chemical compound C12=C(C(F)(F)F)C=C(C=3C=C(C(F)=CC=3)C(O)=O)N=C2N(C)N=C1C1=CC=CC=C1 RTTWSBORQZUXRB-UHFFFAOYSA-N 0.000 claims 1
- HKLPYEAEXVJOEK-UHFFFAOYSA-N 2-fluoro-5-[3-phenyl-4-(trifluoromethyl)-2h-pyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1C1=NC2=NNC(C=3C=CC=CC=3)=C2C(C(F)(F)F)=C1 HKLPYEAEXVJOEK-UHFFFAOYSA-N 0.000 claims 1
- PTLSCXWKSCTSMK-UHFFFAOYSA-N 2-methoxy-5-[1-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(OC)=NC=C1C1=CC(C(F)(F)F)=C(C(=NN2C)C=3C=CC=CC=3)C2=N1 PTLSCXWKSCTSMK-UHFFFAOYSA-N 0.000 claims 1
- RJHRGUQTPSYIDU-UHFFFAOYSA-N 3-(3-methoxyphenyl)-6-(4-methoxyphenyl)-1-methyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridine Chemical group C1=CC(OC)=CC=C1C1=CC(C(F)(F)F)=C(C(=NN2C)C=3C=C(OC)C=CC=3)C2=N1 RJHRGUQTPSYIDU-UHFFFAOYSA-N 0.000 claims 1
- ARZQHEYLWDLTRP-UHFFFAOYSA-N 3-[(4-fluorophenyl)methyl]-1-methyl-6-[1-(2-methylpyrazol-3-yl)imidazo[1,5-a]pyridine-3-carbonyl]quinazoline-2,4-dione Chemical compound CN1N=CC=C1C1=C2C=CC=CN2C(C(=O)C=2C=C3C(=O)N(CC=4C=CC(F)=CC=4)C(=O)N(C)C3=CC=2)=N1 ARZQHEYLWDLTRP-UHFFFAOYSA-N 0.000 claims 1
- DSYKXFMYJFZKKA-UHFFFAOYSA-N 3-[(4-fluorophenyl)methyl]-6-[1-(1-methylpyrazol-4-yl)imidazo[1,5-a]pyridine-3-carbonyl]-1-propylquinazoline-2,4-dione Chemical compound O=C1N(CCC)C2=CC=C(C(=O)C=3N4C=CC=CC4=C(C4=CN(C)N=C4)N=3)C=C2C(=O)N1CC1=CC=C(F)C=C1 DSYKXFMYJFZKKA-UHFFFAOYSA-N 0.000 claims 1
- XUYVIRDORADGEV-UHFFFAOYSA-N 3-[3-(3-methoxyphenyl)-1-methyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]-n,n-dimethylaniline Chemical compound COC1=CC=CC(C=2C3=C(C=C(N=C3N(C)N=2)C=2C=C(C=CC=2)N(C)C)C(F)(F)F)=C1 XUYVIRDORADGEV-UHFFFAOYSA-N 0.000 claims 1
- SUCBSOCNXYSNGP-UHFFFAOYSA-N 3-[4-(difluoromethyl)-1-methyl-3-phenylpyrazolo[3,4-b]pyridin-6-yl]-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC(C=2N=C3N(C)N=C(C3=C(C(F)F)C=2)C=2C=CC=CC=2)=C1 SUCBSOCNXYSNGP-UHFFFAOYSA-N 0.000 claims 1
- YMBIBHPILXGLEK-UHFFFAOYSA-N 3-[4-(difluoromethyl)-1-methylpyrazolo[3,4-b]pyridin-6-yl]benzonitrile Chemical compound N1=C2N(C)N=CC2=C(C(F)F)C=C1C1=CC=CC(C#N)=C1 YMBIBHPILXGLEK-UHFFFAOYSA-N 0.000 claims 1
- WHZGVJGGAGBLDX-UHFFFAOYSA-N 3-phenyl-6-(3-piperidin-1-ylphenyl)-4-(trifluoromethyl)-2h-pyrazolo[3,4-b]pyridine Chemical compound C=12C(C(F)(F)F)=CC(C=3C=C(C=CC=3)N3CCCCC3)=NC2=NNC=1C1=CC=CC=C1 WHZGVJGGAGBLDX-UHFFFAOYSA-N 0.000 claims 1
- CBISMQZMTOJVRV-UHFFFAOYSA-N 4-(4-amino-3-methoxyphenyl)-n-methyl-1h-pyrazolo[3,4-b]pyridine-6-carboxamide Chemical compound C=12C=NNC2=NC(C(=O)NC)=CC=1C1=CC=C(N)C(OC)=C1 CBISMQZMTOJVRV-UHFFFAOYSA-N 0.000 claims 1
- UHZBKAJJNHNEFR-UHFFFAOYSA-N 4-(difluoromethyl)-3-phenyl-6-(1h-pyrazol-4-yl)-2h-pyrazolo[3,4-b]pyridine Chemical compound C=12C(C(F)F)=CC(C3=CNN=C3)=NC2=NNC=1C1=CC=CC=C1 UHZBKAJJNHNEFR-UHFFFAOYSA-N 0.000 claims 1
- OIXIYWMLMIFHTP-UHFFFAOYSA-N 4-(difluoromethyl)-3-phenyl-6-(3-piperidin-1-ylphenyl)-2h-pyrazolo[3,4-b]pyridine Chemical compound C=12C(C(F)F)=CC(C=3C=C(C=CC=3)N3CCCCC3)=NC2=NNC=1C1=CC=CC=C1 OIXIYWMLMIFHTP-UHFFFAOYSA-N 0.000 claims 1
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- ILFLOGJBNOAWQK-UHFFFAOYSA-N [3-[4-(difluoromethyl)-3-phenyl-2h-pyrazolo[3,4-b]pyridin-6-yl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=12C(C(F)F)=CC(C=3C=C(C=CC=3)C(=O)N3CCCC3)=NC2=NNC=1C1=CC=CC=C1 ILFLOGJBNOAWQK-UHFFFAOYSA-N 0.000 claims 1
- PWCZUKCVCXGDAK-UHFFFAOYSA-N [4-[4-(difluoromethyl)-3-phenyl-2h-pyrazolo[3,4-b]pyridin-6-yl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=12C(C(F)F)=CC(C=3C=CC(=CC=3)C(=O)N3CCCC3)=NC2=NNC=1C1=CC=CC=C1 PWCZUKCVCXGDAK-UHFFFAOYSA-N 0.000 claims 1
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- ACPHNWHANCHRGD-UHFFFAOYSA-N n-[[3-[1-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]phenyl]methyl]methanesulfonamide Chemical compound C12=C(C(F)(F)F)C=C(C=3C=C(CNS(C)(=O)=O)C=CC=3)N=C2N(C)N=C1C1=CC=CC=C1 ACPHNWHANCHRGD-UHFFFAOYSA-N 0.000 claims 1
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- XMRLYFGFOIWGNY-UHFFFAOYSA-N tert-butyl 2-[6-(1-bromo-2-methylindolizine-3-carbonyl)-2,4-dioxo-1h-quinazolin-3-yl]acetate Chemical compound N1C(=O)N(CC(=O)OC(C)(C)C)C(=O)C2=CC(C(=O)C=3N4C=CC=CC4=C(Br)C=3C)=CC=C21 XMRLYFGFOIWGNY-UHFFFAOYSA-N 0.000 claims 1
- 206010043554 thrombocytopenia Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000002757 morpholinyl group Chemical group 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 0 Cc1c2c(C)cc(*)nc2n[n]1* Chemical compound Cc1c2c(C)cc(*)nc2n[n]1* 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
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| PCT/EP2012/075328 WO2013087744A1 (en) | 2011-12-14 | 2012-12-13 | Pyrazolopyridine derivatives, preparation process therefor and therapeutic use thereof |
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| US10138235B2 (en) | 2011-12-14 | 2018-11-27 | Sanofi | Pyrazolopyridine derivatives, preparation process therefor and therapeutic use thereof |
| FR2984325A1 (fr) * | 2011-12-14 | 2013-06-21 | Sanofi Sa | Derives de pyrazolopyridine, leur procede de preparation et leur application en therapeutique |
| AU2013373679A1 (en) | 2013-01-16 | 2015-08-13 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | A soluble fibroblast growth factor receptor 3 (FGR3) polypeptide for use in the prevention or treatment of skeletal growth retardation disorders |
| AR094812A1 (es) | 2013-02-20 | 2015-08-26 | Eisai R&D Man Co Ltd | Derivado de piridina monocíclico como inhibidor del fgfr |
| US20140303121A1 (en) | 2013-03-15 | 2014-10-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| SG11201506687RA (en) | 2013-03-15 | 2015-09-29 | Plexxikon Inc | Heterocyclic compounds and uses thereof |
| PL3007694T3 (pl) * | 2013-06-14 | 2018-12-31 | Sanofi | Pochodne pirazolopirydynowe do zastosowania w leczeniu nowotworu pęcherza moczowego |
| KR102344105B1 (ko) | 2014-08-18 | 2021-12-29 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 모노시클릭 피리딘 유도체의 염 및 이의 결정 |
| ES2887148T3 (es) | 2015-03-25 | 2021-12-21 | Nat Cancer Ct | Agente terapéutico contra el cáncer de vías biliares |
| WO2017053604A1 (en) * | 2015-09-23 | 2017-03-30 | The Regents Of The University Of California | Potent antiviral pyrazolopyridine compounds |
| US12414945B2 (en) | 2015-12-17 | 2025-09-16 | Eisai R&D Management Co., Ltd. | Therapeutic agent for breast cancer |
| PT3481859T (pt) | 2016-07-07 | 2022-05-23 | Pfizer | Polipéptidos do recetor 3 do fator de crescimento dos fibroblastos (sfgfr3) solúveis e utilizações dos mesmos |
| JP7675519B2 (ja) | 2017-10-13 | 2025-05-13 | オプナ バイオ ソシエテ アノニム | キナーゼを調節するための化合物の固体形態 |
| WO2019158731A1 (en) * | 2018-02-16 | 2019-08-22 | Ucb Biopharma Sprl | Pharmaceutical 6,5 heterobicyclic ring derivatives |
| SG11202007591RA (en) | 2018-03-28 | 2020-09-29 | Eisai R&D Man Co Ltd | Therapeutic agent for hepatocellular carcinoma |
| CN108774224B (zh) * | 2018-04-23 | 2020-10-30 | 浙江大学 | 吡唑并[3,4-b]吡啶类化合物及其制备方法和应用 |
| CN110833556A (zh) * | 2018-08-15 | 2020-02-25 | 广西梧州制药（集团）股份有限公司 | 吡唑并嘧啶衍生物在治疗肝纤维化的用途 |
| WO2020178316A1 (en) * | 2019-03-05 | 2020-09-10 | Aziende Chimiche Riunite Angelini Francesco - A.C.R.A.F. S.P.A. | 5- or 7-azaindazoles as beta-lactamase inhibitors |
| CN118791483B (zh) * | 2024-07-01 | 2025-10-21 | 郑州大学 | 一种1H-吡唑并[3,4-b]吡啶类衍生物及其制备方法和应用 |
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| US7855205B2 (en) * | 2004-10-29 | 2010-12-21 | Janssen Pharmaceutica Nv | Pyrimidinyl substituted fused-pyrrolyl compounds useful in treating kinase disorders |
| DE102004061288A1 (de) * | 2004-12-14 | 2006-06-29 | Schering Ag | 3-Amino-Pyrazolo[3,4b]pyridine als Inhibitoren von Proteintyrosinkinasen, deren Herstellung und Verwendung als Arzneimittel |
| DE602006014540D1 (en) * | 2005-05-16 | 2010-07-08 | Irm Llc | Pyrrolopyridinderivate als proteinkinaseinhibitoren |
| US7541367B2 (en) * | 2005-05-31 | 2009-06-02 | Janssen Pharmaceutica, N.V. | 3-benzoimidazolyl-pyrazolopyridines useful in treating kinase disorders |
| FR2889526B1 (fr) * | 2005-08-04 | 2012-02-17 | Aventis Pharma Sa | 7-aza-indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| JP2010502660A (ja) * | 2006-09-06 | 2010-01-28 | エフ．ホフマン−ラ ロシュ アーゲー | プロテインキナーゼインヒビターとしてのヘテロアリール誘導体 |
| KR20090031122A (ko) * | 2007-09-21 | 2009-03-25 | 주식회사 중외제약 | 인다졸 골격을 함유하는 화합물, 이의 제조방법 및 상기화합물을 함유하는 약제학적 조성물 |
| JP4686650B2 (ja) * | 2007-11-30 | 2011-05-25 | ファイザー・リミテッド | 新規なグルココルチコイド受容体アゴニスト |
| US8263610B2 (en) * | 2008-12-30 | 2012-09-11 | Arqule, Inc. | Substituted imidazolyl-5,6-dihydrobenzo[N]isoquinoline compounds |
| FR2951172B1 (fr) * | 2009-10-13 | 2014-09-26 | Pf Medicament | Derives pyrazolopyridines en tant qu'agent anticancereux |
| EP2515655B1 (en) * | 2009-12-21 | 2015-08-05 | Samumed, LLC | 1h-pyrazolo[3,4-beta]pyridines and therapeutic uses thereof |
| WO2012019954A1 (en) * | 2010-08-12 | 2012-02-16 | Evotec (Uk) Ltd. | Pyrazolopyridine compounds as pde10a inhibitors |
| FR2984325A1 (fr) * | 2011-12-14 | 2013-06-21 | Sanofi Sa | Derives de pyrazolopyridine, leur procede de preparation et leur application en therapeutique |
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2011
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- 2012-12-13 BR BR112014014452A patent/BR112014014452A2/pt not_active Application Discontinuation
- 2012-12-13 CA CA2857749A patent/CA2857749A1/en not_active Abandoned
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2014
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- 2014-07-10 CO CO14149160A patent/CO7000778A2/es unknown
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2017
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- 2017-07-07 JP JP2017133321A patent/JP2017206544A/ja not_active Withdrawn
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