BR112021014865A2 - Pirazolopiridinas e triazolopiridinas como inibidores de a2a/a2b - Google Patents

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Publication number

BR112021014865A2

BR112021014865A2 BR112021014865-5A BR112021014865A BR112021014865A2 BR 112021014865 A2 BR112021014865 A2 BR 112021014865A2 BR 112021014865 A BR112021014865 A BR 112021014865A BR 112021014865 A2 BR112021014865 A2 BR 112021014865A2

Authority

BR

Brazil

Prior art keywords

alkyl

cycloalkyl

aryl

membered

independently selected

Prior art date

2019-01-29

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• 239000003112 inhibitor Substances 0.000 title abstract description 62
• 150000005229 pyrazolopyridines Chemical class 0.000 title abstract description 3
• 150000008523 triazolopyridines Chemical class 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 293
• -1 for example Chemical compound 0.000 claims abstract description 148
• 150000003839 salts Chemical class 0.000 claims abstract description 105
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 62
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 51
• 201000010099 disease Diseases 0.000 claims abstract description 38
• 102000009346 Adenosine receptors Human genes 0.000 claims abstract description 33
• 108050000203 Adenosine receptors Proteins 0.000 claims abstract description 33
• 201000011510 cancer Diseases 0.000 claims abstract description 30
• 101150078577 Adora2b gene Proteins 0.000 claims abstract description 15
• 230000000694 effects Effects 0.000 claims abstract description 15
• 102000005962 receptors Human genes 0.000 claims abstract description 15
• 108020003175 receptors Proteins 0.000 claims abstract description 15
• 101150051188 Adora2a gene Proteins 0.000 claims abstract description 12
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 11
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 9
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 532
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 300
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 255
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 172
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 170
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 144
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 142
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 135
• 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 120
• 125000000217 alkyl group Chemical group 0.000 claims description 115
• 125000001424 substituent group Chemical group 0.000 claims description 110
• 238000000034 method Methods 0.000 claims description 81
• 125000005843 halogen group Chemical group 0.000 claims description 64
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 54
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 54
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 53
• 125000004429 atom Chemical group 0.000 claims description 44
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 42
• 101100079340 Rattus norvegicus Nalcn gene Proteins 0.000 claims description 32
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 30
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 30
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 229910052796 boron Inorganic materials 0.000 claims description 25
• 208000035475 disorder Diseases 0.000 claims description 24
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 19
• 125000006601 (C1-C3) alkylcarbamyl group Chemical group 0.000 claims description 16
• 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 229910052805 deuterium Inorganic materials 0.000 claims description 14
• 125000004043 oxo group Chemical group O=* 0.000 claims description 14
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 10
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
• 125000006599 (C1-C3) alkylaminocarbonylamino group Chemical group 0.000 claims description 8
• 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 8
• 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 8
• 125000006596 (C1-C3) alkylcarbonyloxy group Chemical group 0.000 claims description 8
• 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 8
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 8
• 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 8
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 8
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
• 230000014509 gene expression Effects 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 6
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 6
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 6
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 6
• 206010009944 Colon cancer Diseases 0.000 claims description 6
• 206010060862 Prostate cancer Diseases 0.000 claims description 6
• 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 101100534214 Caenorhabditis elegans sra-21 gene Proteins 0.000 claims description 5
• 101100310928 Caenorhabditis elegans sra-6 gene Proteins 0.000 claims description 5
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
• 206010022489 Insulin Resistance Diseases 0.000 claims description 5
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
• 230000001419 dependent effect Effects 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 201000001441 melanoma Diseases 0.000 claims description 5
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 5
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 5
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 4
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 4
• 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 4
• 108010006654 Bleomycin Proteins 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 206010020751 Hypersensitivity Diseases 0.000 claims description 4
• 206010038389 Renal cancer Diseases 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 229960001561 bleomycin Drugs 0.000 claims description 4
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• RSZLGLXJRHUPFJ-UHFFFAOYSA-N 3-[4-amino-2-(pyridin-2-ylmethyl)-7-pyrimidin-4-ylpyrazolo[4,3-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=CN(N=2)CC1=NC=CC=C1)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 RSZLGLXJRHUPFJ-UHFFFAOYSA-N 0.000 claims description 3
• ZGHJIPAYCDEMPU-UHFFFAOYSA-N 3-[7-amino-2-(pyridin-2-ylmethyl)-4-pyrimidin-4-ylpyrazolo[3,4-c]pyridin-5-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(C=2)CC1=NC=CC=C1)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 ZGHJIPAYCDEMPU-UHFFFAOYSA-N 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
• 206010035664 Pneumonia Diseases 0.000 claims description 3
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
• 208000007536 Thrombosis Diseases 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
• 230000002159 abnormal effect Effects 0.000 claims description 3
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
• 208000029078 coronary artery disease Diseases 0.000 claims description 3
• 125000004802 cyanophenyl group Chemical group 0.000 claims description 3
• 230000008105 immune reaction Effects 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 201000007270 liver cancer Diseases 0.000 claims description 3
• 208000014018 liver neoplasm Diseases 0.000 claims description 3
• 201000005202 lung cancer Diseases 0.000 claims description 3
• 208000020816 lung neoplasm Diseases 0.000 claims description 3
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 3
• 201000002528 pancreatic cancer Diseases 0.000 claims description 3
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 3
• 201000000849 skin cancer Diseases 0.000 claims description 3
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
• 206010046766 uterine cancer Diseases 0.000 claims description 3
• LJJPYMXBCNMUQS-UHFFFAOYSA-N 3-[4-amino-2-(1-pyridin-2-ylethyl)-7-pyrimidin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(N=2)C(C)C1=NC=CC=C1)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 LJJPYMXBCNMUQS-UHFFFAOYSA-N 0.000 claims description 2
• UWNQHIDMVGEEFD-UHFFFAOYSA-N 3-[4-amino-2-(pyridin-2-ylmethyl)-7-pyrimidin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound N1=C(C=2C(C(C1=C1C=C(C#N)C=C[CH]1)=C1C=CN=C[N]1)=NN(N=2)CC1=CC=CC=N1)N UWNQHIDMVGEEFD-UHFFFAOYSA-N 0.000 claims description 2
• HISRVLQRQZQWHM-UHFFFAOYSA-N 3-[4-amino-2-(pyridin-2-ylmethyl)-7-quinolin-6-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound N1=C(C=2C(C(C1=C1C=C(C#N)C=C[CH]1)=C1C=CC3=NC=C[CH]C3=C1)=NN(N=2)CC1=CC=CC=N1)N HISRVLQRQZQWHM-UHFFFAOYSA-N 0.000 claims description 2
• VHJWGRRHCPJQFK-UHFFFAOYSA-N 3-[4-amino-2-(pyridin-2-ylmethyl)-7-quinoxalin-6-yltriazolo[4,5-c]pyridin-6-yl]-2-fluorobenzonitrile Chemical compound N1=C(C=2C(C(C1=C1C(F)=C(C#N)C=C[CH]1)=C1C=CC3=NC=C[N]C3=C1)=NN(N=2)CC1=CC=CC=N1)N VHJWGRRHCPJQFK-UHFFFAOYSA-N 0.000 claims description 2
• CMXICQXZUGQZCI-UHFFFAOYSA-N 3-[4-amino-2-(pyridin-2-ylmethyl)-7-quinoxalin-6-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound N1=C(C=2C(C(C1=C1C=C(C#N)C=C[CH]1)=C1C=CC3=NC=C[N]C3=C1)=NN(N=2)CC1=CC=CC=N1)N CMXICQXZUGQZCI-UHFFFAOYSA-N 0.000 claims description 2
• XQCMGSBIHBANDR-UHFFFAOYSA-N 3-[4-amino-2-[(1-methylpyrazol-3-yl)methyl]-7-pyrimidin-4-ylpyrazolo[4,3-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=CN(N=2)CC1=NN(C=C1)C)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 XQCMGSBIHBANDR-UHFFFAOYSA-N 0.000 claims description 2
• JFXOHCSIEUJACF-UHFFFAOYSA-N 3-[4-amino-2-[(1-methylpyrazol-3-yl)methyl]-7-pyrimidin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(N=2)CC1=NN(C=C1)C)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 JFXOHCSIEUJACF-UHFFFAOYSA-N 0.000 claims description 2
• SJOYFDLIOKJIPV-UHFFFAOYSA-N 3-[4-amino-2-[(2-fluorophenyl)methyl]-7-pyrimidin-4-ylpyrazolo[4,3-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=CN(N=2)CC1=C(C=CC=C1)F)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 SJOYFDLIOKJIPV-UHFFFAOYSA-N 0.000 claims description 2
• OYSQZTKBNXAYBS-UHFFFAOYSA-N 3-[4-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(1-methyl-6-oxopyridin-3-yl)triazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound N1=C(C=2C(C(=C1C1=CC=CC(C#N)=C1)C=1C=CC(=O)N(C=1)C)=NN(N=2)CC1=C(F)C=CC=N1)N OYSQZTKBNXAYBS-UHFFFAOYSA-N 0.000 claims description 2
• FQIOFNQTOKOGQM-UHFFFAOYSA-N 3-[4-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(2-methylpyrazol-3-yl)triazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(N=2)CC1=NC=CC=C1F)C1=CC=NN1C)C=1C=C(C#N)C=CC=1 FQIOFNQTOKOGQM-UHFFFAOYSA-N 0.000 claims description 2
• YORQAJVPPSHHBF-UHFFFAOYSA-N 3-[4-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(4-methyl-1,3-oxazol-5-yl)triazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(N=2)CC1=NC=CC=C1F)C1=C(N=CO1)C)C=1C=C(C#N)C=CC=1 YORQAJVPPSHHBF-UHFFFAOYSA-N 0.000 claims description 2
• UDTYMQWVZMEAGS-UHFFFAOYSA-N 3-[4-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-pyridin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound N1=C(C=2C(C(C1=C1C=C(C#N)C=C[CH]1)=C1C=CN=C[CH]1)=NN(N=2)CC1=C(F)C=CC=N1)N UDTYMQWVZMEAGS-UHFFFAOYSA-N 0.000 claims description 2
• SHCILLFMSNKMJG-UHFFFAOYSA-N 3-[4-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-pyrimidin-4-ylpyrazolo[4,3-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=CN(N=2)CC1=NC=CC=C1F)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 SHCILLFMSNKMJG-UHFFFAOYSA-N 0.000 claims description 2
• MSXIFXOIITVIOS-UHFFFAOYSA-N 3-[4-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-pyrimidin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(N=2)CC1=NC=CC=C1F)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 MSXIFXOIITVIOS-UHFFFAOYSA-N 0.000 claims description 2
• WHAOWXKRSWIAPM-UHFFFAOYSA-N 3-[4-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-quinoxalin-6-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(N=2)CC1=NC=CC=C1F)C=1C=C2N=CC=NC2=CC=1)C=1C=C(C#N)C=CC=1 WHAOWXKRSWIAPM-UHFFFAOYSA-N 0.000 claims description 2
• ZOHVIRCGTAKCGS-UHFFFAOYSA-N 3-[4-amino-2-[(6-methylpyridin-2-yl)methyl]-7-pyridin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound N1=C(C=2C(C(C1=C1C=C(C#N)C=C[CH]1)=C1C=CN=C[CH]1)=NN(N=2)CC1=CC=CC(C)=N1)N ZOHVIRCGTAKCGS-UHFFFAOYSA-N 0.000 claims description 2
• LJXPHLLWHJOYSO-UHFFFAOYSA-N 3-[4-amino-2-[(6-methylpyridin-2-yl)methyl]-7-pyrimidin-4-ylpyrazolo[4,3-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=CN(N=2)CC1=NC(=CC=C1)C)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 LJXPHLLWHJOYSO-UHFFFAOYSA-N 0.000 claims description 2
• ZSMYNSQPYMMGDV-UHFFFAOYSA-N 3-[4-amino-2-[(6-methylpyridin-2-yl)methyl]-7-pyrimidin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(N=2)CC1=NC(=CC=C1)C)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 ZSMYNSQPYMMGDV-UHFFFAOYSA-N 0.000 claims description 2
• LVEMXZQJZADZNC-UHFFFAOYSA-N 3-[4-amino-7-(1,3-oxazol-5-yl)-2-(pyridin-2-ylmethyl)triazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(N=2)CC1=NC=CC=C1)C1=CN=CO1)C=1C=C(C#N)C=CC=1 LVEMXZQJZADZNC-UHFFFAOYSA-N 0.000 claims description 2
• QRHRYYOLCHXSNH-UHFFFAOYSA-N 3-[4-amino-7-(1-methyl-6-oxopyridin-3-yl)-2-[(6-methylpyridin-2-yl)methyl]triazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound N1=C(C=2C(C(=C1C1=CC(C#N)=CC=C1)C=1C=CC(=O)N(C=1)C)=NN(N=2)CC1=CC=CC(C)=N1)N QRHRYYOLCHXSNH-UHFFFAOYSA-N 0.000 claims description 2
• QDPGJDVOYUZJSD-UHFFFAOYSA-N 3-[4-amino-7-(2-ethylpyrazol-3-yl)-2-(pyridin-2-ylmethyl)pyrazolo[4,3-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=CN(N=2)CC1=NC=CC=C1)C1=CC=NN1CC)C=1C=C(C#N)C=CC=1 QDPGJDVOYUZJSD-UHFFFAOYSA-N 0.000 claims description 2
• IGMOYJYSLPSDFG-UHFFFAOYSA-N 3-[4-amino-7-(2-ethylpyrazol-3-yl)-2-(pyridin-2-ylmethyl)triazolo[4,5-c]pyridin-6-yl]-2-fluorobenzonitrile Chemical compound N1=C(C=2C(C(=C1C1=C(F)C(C#N)=CC=C1)C1=CC=NN1CC)=NN(N=2)CC1=CC=CC=N1)N IGMOYJYSLPSDFG-UHFFFAOYSA-N 0.000 claims description 2
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