EA027421B1 - Пиразолопиридиновые производные, способы их получения и их терапевтическое применение - Google Patents

Info

Publication number

EA027421B1

EA027421B1 EA201491149A EA201491149A EA027421B1 EA 027421 B1 EA027421 B1 EA 027421B1 EA 201491149 A EA201491149 A EA 201491149A EA 201491149 A EA201491149 A EA 201491149A EA 027421 B1 EA027421 B1 EA 027421B1

Authority

EA

Eurasian Patent Office

Prior art keywords

sub

text

group

pyrazolo

phenyl

Prior art date

2011-12-14

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• 230000001225 therapeutic effect Effects 0.000 title abstract description 5
• 238000002360 preparation method Methods 0.000 title description 6
• 150000005229 pyrazolopyridines Chemical class 0.000 title 1
• 238000004519 manufacturing process Methods 0.000 claims abstract description 10
• 150000001875 compounds Chemical class 0.000 claims description 136
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 108
• 229910052757 nitrogen Inorganic materials 0.000 claims description 100
• 125000000217 alkyl group Chemical group 0.000 claims description 94
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 78
• -1 1-methyl-3-phenyl-4-trifluoromethyl-1H-pyrazolo [3,4-b] pyridin-6-yl Chemical group 0.000 claims description 76
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 69
• 125000001424 substituent group Chemical group 0.000 claims description 64
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
• 125000002757 morpholinyl group Chemical group 0.000 claims description 56
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 55
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
• 229920006395 saturated elastomer Polymers 0.000 claims description 51
• 125000004076 pyridyl group Chemical group 0.000 claims description 49
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 45
• 125000000623 heterocyclic group Chemical group 0.000 claims description 44
• 238000011282 treatment Methods 0.000 claims description 44
• 125000004432 carbon atom Chemical group C* 0.000 claims description 35
• 206010028980 Neoplasm Diseases 0.000 claims description 34
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 34
• 238000002844 melting Methods 0.000 claims description 31
• 230000008018 melting Effects 0.000 claims description 31
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 29
• 239000002253 acid Substances 0.000 claims description 29
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 29
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
• 239000002585 base Substances 0.000 claims description 28
• 238000002560 therapeutic procedure Methods 0.000 claims description 27
• 239000000654 additive Substances 0.000 claims description 26
• 230000000996 additive effect Effects 0.000 claims description 26
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
• 125000005936 piperidyl group Chemical group 0.000 claims description 23
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 23
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 238000000034 method Methods 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 230000002265 prevention Effects 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 16
• 108090000379 Fibroblast growth factor 2 Proteins 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 125000003118 aryl group Chemical group 0.000 claims description 14
• 201000011510 cancer Diseases 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 12
• 125000001544 thienyl group Chemical group 0.000 claims description 12
• 125000004849 alkoxymethyl group Chemical group 0.000 claims description 11
• 125000002619 bicyclic group Chemical group 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
• 229940079593 drug Drugs 0.000 claims description 10
• 201000010072 hypochondroplasia Diseases 0.000 claims description 10
• 208000002780 macular degeneration Diseases 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 9
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• 230000002792 vascular Effects 0.000 claims description 9
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
• 238000009833 condensation Methods 0.000 claims description 8
• 230000005494 condensation Effects 0.000 claims description 8
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• 206010008723 Chondrodystrophy Diseases 0.000 claims description 7
• 206010018338 Glioma Diseases 0.000 claims description 7
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• 210000003734 kidney Anatomy 0.000 claims description 7
• 239000003446 ligand Substances 0.000 claims description 7
• 210000004185 liver Anatomy 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 238000001959 radiotherapy Methods 0.000 claims description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 6
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 6
• 238000002399 angioplasty Methods 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 208000037803 restenosis Diseases 0.000 claims description 6
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 5
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• 206010058314 Dysplasia Diseases 0.000 claims description 5
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• 208000008589 Obesity Diseases 0.000 claims description 5
• 230000001093 anti-cancer Effects 0.000 claims description 5
• 208000037976 chronic inflammation Diseases 0.000 claims description 5
• 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 235000020824 obesity Nutrition 0.000 claims description 5
• 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
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 4
• 238000005804 alkylation reaction Methods 0.000 claims description 4
• 239000003054 catalyst Substances 0.000 claims description 4
• 238000006243 chemical reaction Methods 0.000 claims description 4
• 210000004351 coronary vessel Anatomy 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 208000004296 neuralgia Diseases 0.000 claims description 4
• 208000021722 neuropathic pain Diseases 0.000 claims description 4
• 229910052763 palladium Inorganic materials 0.000 claims description 4
• 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 3
• 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 3
• 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 3
• 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 3
• 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 description 3
• 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 3
• 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 3
• 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 3
• 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 3
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 3
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
• 206010059394 acanthoma Diseases 0.000 claims description 3
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
• 201000011539 clear cell acanthoma Diseases 0.000 claims description 3
• 230000006806 disease prevention Effects 0.000 claims description 3
• 206010017758 gastric cancer Diseases 0.000 claims description 3
• 201000008482 osteoarthritis Diseases 0.000 claims description 3
• BLDLTMVNCFWBLW-UHFFFAOYSA-N pyrrolidin-1-ylmethanone Chemical compound O=[C]N1CCCC1 BLDLTMVNCFWBLW-UHFFFAOYSA-N 0.000 claims description 3
• 201000011549 stomach cancer Diseases 0.000 claims description 3
• 206010043554 thrombocytopenia Diseases 0.000 claims description 3
• 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 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
• BQNPGPSVAAFSFY-UHFFFAOYSA-N 6-(4-amino-3-cyanophenyl)-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid Chemical compound C1=C(C#N)C(N)=CC=C1C1=CC(C(O)=O)=C(C=NN2)C2=N1 BQNPGPSVAAFSFY-UHFFFAOYSA-N 0.000 claims description 2
• FAULCBMZRYIEPU-UHFFFAOYSA-N 6-(6-methoxypyridin-3-yl)-1-methyl-3-phenyl-4-(trifluoromethyl)pyrazolo[3,4-b]pyridine Chemical compound C1=NC(OC)=CC=C1C1=CC(C(F)(F)F)=C(C(=NN2C)C=3C=CC=CC=3)C2=N1 FAULCBMZRYIEPU-UHFFFAOYSA-N 0.000 claims description 2
• 206010023421 Kidney fibrosis Diseases 0.000 claims description 2
• 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims description 2
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• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 9
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
• KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 claims 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
• 201000003741 Gastrointestinal carcinoma Diseases 0.000 claims 2
• 229910052736 halogen Inorganic materials 0.000 claims 2
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 2
• 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 1
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 1
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