DK2791137T3 - PYRAZOLOPYRIDINE DERIVATIVES, METHOD OF PREPARING THESE AND THERAPEUTIC USE THEREOF - Google Patents

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Publication number

DK2791137T3

DK2791137T3 DK12808328.4T DK12808328T DK2791137T3 DK 2791137 T3 DK2791137 T3 DK 2791137T3 DK 12808328 T DK12808328 T DK 12808328T DK 2791137 T3 DK2791137 T3 DK 2791137T3

Authority

DK

Denmark

Prior art keywords

group

pyrazolo

phenyl

pyridin

pyridine

Prior art date

2011-12-14

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• 238000000034 method Methods 0.000 title claims description 27
• 230000001225 therapeutic effect Effects 0.000 title description 2
• 150000005229 pyrazolopyridines Chemical class 0.000 title 1
• 229910052757 nitrogen Inorganic materials 0.000 claims description 200
• 150000001875 compounds Chemical class 0.000 claims description 180
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 159
• 125000000217 alkyl group Chemical group 0.000 claims description 90
• 125000005842 heteroatom Chemical group 0.000 claims description 83
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 81
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 79
• 125000003118 aryl group Chemical group 0.000 claims description 77
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 76
• 125000004076 pyridyl group Chemical group 0.000 claims description 75
• 125000001424 substituent group Chemical group 0.000 claims description 66
• 229920006395 saturated elastomer Polymers 0.000 claims description 56
• 125000000623 heterocyclic group Chemical group 0.000 claims description 49
• 238000011282 treatment Methods 0.000 claims description 46
• 206010028980 Neoplasm Diseases 0.000 claims description 45
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 35
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
• 125000005843 halogen group Chemical group 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 30
• 125000004432 carbon atom Chemical group C* 0.000 claims description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
• -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 20
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 230000002265 prevention Effects 0.000 claims description 17
• 125000001544 thienyl group Chemical group 0.000 claims description 17
• 239000002253 acid Substances 0.000 claims description 16
• 125000004849 alkoxymethyl group Chemical group 0.000 claims description 16
• 125000002619 bicyclic group Chemical group 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 238000006243 chemical reaction Methods 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 230000008569 process Effects 0.000 claims description 16
• 125000004434 sulfur atom Chemical group 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 201000010099 disease Diseases 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 14
• 239000003446 ligand Substances 0.000 claims description 14
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 14
• 238000006069 Suzuki reaction reaction Methods 0.000 claims description 12
• 201000011510 cancer Diseases 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 150000002148 esters Chemical class 0.000 claims description 12
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 11
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 10
• 201000010072 hypochondroplasia Diseases 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 229910052763 palladium Inorganic materials 0.000 claims description 10
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
• 230000002792 vascular Effects 0.000 claims description 10
• 201000001441 melanoma Diseases 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 210000002307 prostate Anatomy 0.000 claims description 9
• 206010018338 Glioma Diseases 0.000 claims description 8
• 206010027476 Metastases Diseases 0.000 claims description 8
• 238000005804 alkylation reaction Methods 0.000 claims description 8
• 210000004185 liver Anatomy 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000006239 protecting group Chemical group 0.000 claims description 8
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 7
• 210000000481 breast Anatomy 0.000 claims description 7
• 208000037803 restenosis Diseases 0.000 claims description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 6
• 201000009030 Carcinoma Diseases 0.000 claims description 6
• 206010025323 Lymphomas Diseases 0.000 claims description 6
• 230000001093 anti-cancer Effects 0.000 claims description 6
• 208000037976 chronic inflammation Diseases 0.000 claims description 6
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 6
• 208000032839 leukemia Diseases 0.000 claims description 6
• 210000004072 lung Anatomy 0.000 claims description 6
• 238000001959 radiotherapy Methods 0.000 claims description 6
• 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 description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 201000003741 Gastrointestinal carcinoma Diseases 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 206010043554 thrombocytopenia Diseases 0.000 claims description 5
• 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 description 4
• 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 description 4
• 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 description 4
• FTZOTEZEJXGMME-UHFFFAOYSA-N 4-[[3-[1-methyl-3-pyridin-3-yl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridin-6-yl]phenyl]methyl]morpholine Chemical compound C12=C(C(F)(F)F)C=C(C=3C=C(CN4CCOCC4)C=CC=3)N=C2N(C)N=C1C1=CC=CN=C1 FTZOTEZEJXGMME-UHFFFAOYSA-N 0.000 claims description 4
• AUBQNGHWNDGCEQ-UHFFFAOYSA-N 5-(4-carbamoyl-3-phenyl-2h-pyrazolo[3,4-b]pyridin-6-yl)-2-fluorobenzoic acid Chemical compound C=12C(C(=O)N)=CC(C=3C=C(C(F)=CC=3)C(O)=O)=NC2=NNC=1C1=CC=CC=C1 AUBQNGHWNDGCEQ-UHFFFAOYSA-N 0.000 claims description 4
• QPWPGHMKKMZBOQ-UHFFFAOYSA-N 5-[4-(difluoromethyl)-3-phenyl-2h-pyrazolo[3,4-b]pyridin-6-yl]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(C2=NC3=NNC(=C3C(C(F)F)=C2)C=2C=CC=CC=2)=C1 QPWPGHMKKMZBOQ-UHFFFAOYSA-N 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 206010059394 acanthoma Diseases 0.000 claims description 4
• 201000011539 clear cell acanthoma Diseases 0.000 claims description 4
• 238000010511 deprotection reaction Methods 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 206010020718 hyperplasia Diseases 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 208000004296 neuralgia Diseases 0.000 claims description 4
• 208000021722 neuropathic pain Diseases 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 201000002313 intestinal cancer Diseases 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 201000008482 osteoarthritis Diseases 0.000 claims description 3
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
• 230000002861 ventricular Effects 0.000 claims description 3
• 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 description 2
• LCLBVTCUCJAIJI-UHFFFAOYSA-N 1-methyl-6-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridine Chemical compound Cn1nc(cc1-c1cc(c2c(nn(C)c2n1)-c1ccccc1)C(F)(F)F)C(F)(F)F LCLBVTCUCJAIJI-UHFFFAOYSA-N 0.000 claims description 2
• JRNIMXLHKJWSAW-UHFFFAOYSA-N 1-methyl-6-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridine Chemical compound N1=C2N(C)N=CC2=C(C(F)(F)F)C=C1C1=CC=CC=C1 JRNIMXLHKJWSAW-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• BHLPXUUPYBYOGC-UHFFFAOYSA-N 4-(difluoromethyl)-1-methyl-6-phenylpyrazolo[3,4-b]pyridine Chemical compound N1=C2N(C)N=CC2=C(C(F)F)C=C1C1=CC=CC=C1 BHLPXUUPYBYOGC-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• HPDGNDRZBNAOGH-UHFFFAOYSA-N 4-(difluoromethyl)-6-(1-ethylpyrazol-4-yl)-1-methylpyrazolo[3,4-b]pyridine Chemical compound C1=NN(CC)C=C1C1=CC(C(F)F)=C(C=NN2C)C2=N1 HPDGNDRZBNAOGH-UHFFFAOYSA-N 0.000 claims description 2
• URBVUBBMVBIZKQ-UHFFFAOYSA-N 4-(difluoromethyl)-6-(1-methylpyrazol-4-yl)-3-phenyl-2h-pyrazolo[3,4-b]pyridine Chemical compound C1=NN(C)C=C1C1=NC2=NNC(C=3C=CC=CC=3)=C2C(C(F)F)=C1 URBVUBBMVBIZKQ-UHFFFAOYSA-N 0.000 claims description 2
• FXLZVIKWLKPVOL-UHFFFAOYSA-N 4-(difluoromethyl)-6-(3,4-dimethoxyphenyl)-1-methylpyrazolo[3,4-b]pyridine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C(F)F)=C(C=NN2C)C2=N1 FXLZVIKWLKPVOL-UHFFFAOYSA-N 0.000 claims description 2
• YLOTWSXGOLNHFL-UHFFFAOYSA-N 4-(difluoromethyl)-6-(3-methoxyphenyl)-1-methylpyrazolo[3,4-b]pyridine Chemical compound COC1=CC=CC(C=2N=C3N(C)N=CC3=C(C(F)F)C=2)=C1 YLOTWSXGOLNHFL-UHFFFAOYSA-N 0.000 claims description 2
• QNQNRVJRYSQYPE-UHFFFAOYSA-N 4-(difluoromethyl)-6-(6-methoxypyridin-3-yl)-3-phenyl-2h-pyrazolo[3,4-b]pyridine Chemical compound C1=NC(OC)=CC=C1C1=NC2=NNC(C=3C=CC=CC=3)=C2C(C(F)F)=C1 QNQNRVJRYSQYPE-UHFFFAOYSA-N 0.000 claims description 2
• LYBKSSQIMSGFMK-UHFFFAOYSA-N 4-[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=CC(=CC=3)C(O)=O)N=C2N(C)N=C1C1=CC=CC=C1 LYBKSSQIMSGFMK-UHFFFAOYSA-N 0.000 claims description 2
• AKJBKDJBAWCDNX-UHFFFAOYSA-N 4-[3-[3-phenyl-4-(trifluoromethyl)-2h-pyrazolo[3,4-b]pyridin-6-yl]phenyl]morpholine Chemical compound C=12C(C(F)(F)F)=CC(C=3C=C(C=CC=3)N3CCOCC3)=NC2=NNC=1C1=CC=CC=C1 AKJBKDJBAWCDNX-UHFFFAOYSA-N 0.000 claims description 2
• WEHSRMBZPWWCPC-UHFFFAOYSA-N 4-[3-phenyl-4-(trifluoromethyl)-2h-pyrazolo[3,4-b]pyridin-6-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=NC2=NNC(C=3C=CC=CC=3)=C2C(C(F)(F)F)=C1 WEHSRMBZPWWCPC-UHFFFAOYSA-N 0.000 claims description 2
• QDSFJVLFJUXWPU-UHFFFAOYSA-N 4-[4-(difluoromethyl)-1-methyl-3-phenylpyrazolo[3,4-b]pyridin-6-yl]aniline Chemical compound C12=C(C(F)F)C=C(C=3C=CC(N)=CC=3)N=C2N(C)N=C1C1=CC=CC=C1 QDSFJVLFJUXWPU-UHFFFAOYSA-N 0.000 claims description 2
• JDHJXCNCSTURLR-UHFFFAOYSA-N 4-[4-(difluoromethyl)-1-methylpyrazolo[3,4-b]pyridin-6-yl]aniline Chemical compound N1=C2N(C)N=CC2=C(C(F)F)C=C1C1=CC=C(N)C=C1 JDHJXCNCSTURLR-UHFFFAOYSA-N 0.000 claims description 2
• DOKBQUHMXPRESN-UHFFFAOYSA-N 4-[4-[3-phenyl-4-(trifluoromethyl)-2h-pyrazolo[3,4-b]pyridin-6-yl]phenyl]morpholine Chemical compound C=12C(C(F)(F)F)=CC(C=3C=CC(=CC=3)N3CCOCC3)=NC2=NNC=1C1=CC=CC=C1 DOKBQUHMXPRESN-UHFFFAOYSA-N 0.000 claims description 2
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