BR112016015236B1 - Composto, composições farmacêuticas, usos de um composto e método in vitro de inibição da atividade da proteína quinase erk - Google Patents

Info

Publication number

BR112016015236B1

BR112016015236B1 BR112016015236-0A BR112016015236A BR112016015236B1 BR 112016015236 B1 BR112016015236 B1 BR 112016015236B1 BR 112016015236 A BR112016015236 A BR 112016015236A BR 112016015236 B1 BR112016015236 B1 BR 112016015236B1

Authority

BR

Brazil

Prior art keywords

methyl

pyridin

pyrazol

triazolo

pyrimidin

Prior art date

2013-12-30

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 174
• 238000000034 method Methods 0.000 title claims abstract description 85
• 230000000694 effects Effects 0.000 title claims abstract description 18
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
• 230000002401 inhibitory effect Effects 0.000 title claims abstract description 8
• 238000000338 in vitro Methods 0.000 title claims abstract description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 71
• 150000003839 salts Chemical class 0.000 claims abstract description 58
• 201000010099 disease Diseases 0.000 claims abstract description 49
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 32
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 12
• -1 methoxy, oxo, cyclopropyl Chemical group 0.000 claims description 1613
• 229910052736 halogen Inorganic materials 0.000 claims description 355
• 150000002367 halogens Chemical class 0.000 claims description 355
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 171
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 115
• 239000001257 hydrogen Substances 0.000 claims description 111
• 229910052739 hydrogen Inorganic materials 0.000 claims description 111
• 125000005842 heteroatom Chemical group 0.000 claims description 102
• 125000000623 heterocyclic group Chemical group 0.000 claims description 101
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 80
• 125000000217 alkyl group Chemical group 0.000 claims description 70
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 68
• 229910052717 sulfur Inorganic materials 0.000 claims description 67
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
• 229910052760 oxygen Inorganic materials 0.000 claims description 61
• 125000001072 heteroaryl group Chemical group 0.000 claims description 60
• 125000004043 oxo group Chemical group O=* 0.000 claims description 56
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 54
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 54
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 50
• 206010028980 Neoplasm Diseases 0.000 claims description 44
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 38
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 38
• 201000011510 cancer Diseases 0.000 claims description 36
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 35
• 229920006395 saturated elastomer Polymers 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
• 208000035475 disorder Diseases 0.000 claims description 22
• MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 239000011737 fluorine Chemical group 0.000 claims description 18
• 229910052731 fluorine Chemical group 0.000 claims description 18
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 18
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 16
• 201000009030 Carcinoma Diseases 0.000 claims description 11
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 11
• 208000026310 Breast neoplasm Diseases 0.000 claims description 10
• 206010009944 Colon cancer Diseases 0.000 claims description 10
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 10
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 10
• 201000002528 pancreatic cancer Diseases 0.000 claims description 10
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 9
• 206010006187 Breast cancer Diseases 0.000 claims description 9
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 9
• 206010033128 Ovarian cancer Diseases 0.000 claims description 9
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
• 201000005202 lung cancer Diseases 0.000 claims description 9
• 208000020816 lung neoplasm Diseases 0.000 claims description 9
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 201000001441 melanoma Diseases 0.000 claims description 9
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 9
• 201000002510 thyroid cancer Diseases 0.000 claims description 9
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 7
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 239000002246 antineoplastic agent Substances 0.000 claims description 7
• 229940127089 cytotoxic agent Drugs 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
• 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 6
• TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 5
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
• 208000008035 Back Pain Diseases 0.000 claims description 5
• 206010005003 Bladder cancer Diseases 0.000 claims description 5
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
• 208000008930 Low Back Pain Diseases 0.000 claims description 5
• 206010038389 Renal cancer Diseases 0.000 claims description 5
• 206010039491 Sarcoma Diseases 0.000 claims description 5
• 206010003246 arthritis Diseases 0.000 claims description 5
• 208000005017 glioblastoma Diseases 0.000 claims description 5
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 201000003068 rheumatic fever Diseases 0.000 claims description 5
• QNZSORSPBZCQPP-UHFFFAOYSA-N 4-[3-[(3-bromophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CC3=CC(Br)=CC=C3)N2C=C1 QNZSORSPBZCQPP-UHFFFAOYSA-N 0.000 claims description 4
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
• 208000003200 Adenoma Diseases 0.000 claims description 4
• 206010001233 Adenoma benign Diseases 0.000 claims description 4
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 4
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
• 208000017604 Hodgkin disease Diseases 0.000 claims description 4
• 206010023347 Keratoacanthoma Diseases 0.000 claims description 4
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 4
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 4
• 208000033833 Myelomonocytic Chronic Leukemia Diseases 0.000 claims description 4
• 206010029260 Neuroblastoma Diseases 0.000 claims description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 4
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 4
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 201000010902 chronic myelomonocytic leukemia Diseases 0.000 claims description 4
• 208000029742 colonic neoplasm Diseases 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 201000010536 head and neck cancer Diseases 0.000 claims description 4
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 4
• 201000010982 kidney cancer Diseases 0.000 claims description 4
• 208000003849 large cell carcinoma Diseases 0.000 claims description 4
• 208000025113 myeloid leukemia Diseases 0.000 claims description 4
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 4
• 201000010198 papillary carcinoma Diseases 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 206010038038 rectal cancer Diseases 0.000 claims description 4
• 201000001275 rectum cancer Diseases 0.000 claims description 4
• 201000000849 skin cancer Diseases 0.000 claims description 4
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 4
• 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims description 4
• 208000010576 undifferentiated carcinoma Diseases 0.000 claims description 4
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 4
• JQXCNGPCMZCTIK-ZDUSSCGKSA-N (2S)-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]butan-2-ol Chemical compound CC[C@H](O)CC1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1 JQXCNGPCMZCTIK-ZDUSSCGKSA-N 0.000 claims description 3
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims description 3
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 3
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 3
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 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
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 3
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
• 125000005916 2-methylpentyl group Chemical group 0.000 claims description 3
• 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
• 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000005917 3-methylpentyl group Chemical group 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 3
• 208000009956 adenocarcinoma Diseases 0.000 claims description 3
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 3
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
• 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 3
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
• 125000004250 isochroman-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])OC2([H])* 0.000 claims description 3
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 3
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 201000005249 lung adenocarcinoma Diseases 0.000 claims description 3
• 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 3
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims description 3
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 3
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 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
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
• YILNBPSRRRQFFH-LJQANCHMSA-N (R)-cyclohexyl-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methanol Chemical compound C1(CCCCC1)[C@@H](O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YILNBPSRRRQFFH-LJQANCHMSA-N 0.000 claims description 2
• RIEKIFDEVPAKOC-UHFFFAOYSA-N 4-[3-(2-ethoxybutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CCOC(CC)CC1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1 RIEKIFDEVPAKOC-UHFFFAOYSA-N 0.000 claims description 2
• CCVCSMLLROVRNC-UHFFFAOYSA-N 4-[3-(2-methylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound CN1N=CC(=C1)NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(CC)C CCVCSMLLROVRNC-UHFFFAOYSA-N 0.000 claims description 2
• ZKROPNQERHXKAI-UHFFFAOYSA-N 4-[3-(2-methylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CCC(C)CC1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1 ZKROPNQERHXKAI-UHFFFAOYSA-N 0.000 claims description 2
• QXHROWRGLLTQSR-UHFFFAOYSA-N 4-[3-[(1-methoxycyclobutyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1(CC2=NN=C3C=C(C=CN23)C2=CC=NC(NC3=CC=NN3C)=N2)CCC1 QXHROWRGLLTQSR-UHFFFAOYSA-N 0.000 claims description 2
• JRPOFDRXMCLTHX-UHFFFAOYSA-N 4-[3-[(1-methoxycyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1(CC2=NN=C3C=C(C=CN23)C2=CC=NC(NC3=CC=NN3C)=N2)CC1 JRPOFDRXMCLTHX-UHFFFAOYSA-N 0.000 claims description 2
• JJRHUWJROOZGMP-UHFFFAOYSA-N 4-[3-[(3-cyclobutylphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CC3=CC(=CC=C3)C3CCC3)N2C=C1 JJRHUWJROOZGMP-UHFFFAOYSA-N 0.000 claims description 2
• XXDWVJIXPORACA-UHFFFAOYSA-N 4-[3-[(5-bromopyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CC3=CC(Br)=CN=C3)N2C=C1 XXDWVJIXPORACA-UHFFFAOYSA-N 0.000 claims description 2
• SEDOVQAGAGKZRM-UHFFFAOYSA-N 4-[3-[(6-chloropyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=CC(=N1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C SEDOVQAGAGKZRM-UHFFFAOYSA-N 0.000 claims description 2
• ZIQCQUNIJMVNAB-UHFFFAOYSA-N 4-[3-[1-[(2-fluoro-6-methoxyphenyl)methyl]piperidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound FC1=C(CN2CC(CCC2)C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C(=CC=C1)OC ZIQCQUNIJMVNAB-UHFFFAOYSA-N 0.000 claims description 2
• UDCCDKXRWWJEIM-UHFFFAOYSA-N 4-[3-[3-(3-chlorophenyl)-1,5-dimethylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(C=CC=1)C1=NN(C(=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C)C UDCCDKXRWWJEIM-UHFFFAOYSA-N 0.000 claims description 2
• XNSYGDXQYQDZPW-UHFFFAOYSA-N 4-[3-[4-[(2-fluoro-6-methoxyphenyl)methyl]morpholin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CN2CC(OCC2)C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C(=CC=C1)OC XNSYGDXQYQDZPW-UHFFFAOYSA-N 0.000 claims description 2
• SQGGPIBCLGNLAG-UHFFFAOYSA-N 4-[3-[4-[(2-fluoro-6-methoxyphenyl)methyl]morpholin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound FC1=C(CN2CC(OCC2)C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C(=CC=C1)OC SQGGPIBCLGNLAG-UHFFFAOYSA-N 0.000 claims description 2
• OBFOBJXUPDLDFU-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(thiophen-2-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CC3=CC=CS3)N2C=C1 OBFOBJXUPDLDFU-UHFFFAOYSA-N 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 6
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 4
• 208000003174 Brain Neoplasms Diseases 0.000 claims 3
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims 3
• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 3
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 3
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
• 208000024313 Testicular Neoplasms Diseases 0.000 claims 2
• 206010057644 Testis cancer Diseases 0.000 claims 2
• 208000000649 small cell carcinoma Diseases 0.000 claims 2
• 201000003120 testicular cancer Diseases 0.000 claims 2
• MQSYOBLXLDSEJB-GOSISDBHSA-N (1R)-1-(4-chlorophenyl)-2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethanol Chemical compound ClC1=CC=C(C=C1)[C@@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O MQSYOBLXLDSEJB-GOSISDBHSA-N 0.000 claims 1
• IYSVMODTMJUHPB-LJQANCHMSA-N (1R)-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyridin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]-2-phenylethanol Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)[C@@H](CC1=CC=CC=C1)O IYSVMODTMJUHPB-LJQANCHMSA-N 0.000 claims 1
• RMXYBJAKMHYTTF-GOSISDBHSA-N (1R)-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]-2-phenylethanol Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)[C@@H](CC1=CC=CC=C1)O RMXYBJAKMHYTTF-GOSISDBHSA-N 0.000 claims 1
• PCHUEGKOMSGREH-MRXNPFEDSA-N (1R)-2-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-1-ol Chemical compound CC([C@@H](O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C PCHUEGKOMSGREH-MRXNPFEDSA-N 0.000 claims 1
• YLESVYQTCPZCJT-OAHLLOKOSA-N (1R)-3-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]butan-1-ol Chemical compound CC(C[C@@H](O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C YLESVYQTCPZCJT-OAHLLOKOSA-N 0.000 claims 1
• PDDQXZBCZSODGW-YVEFUNNKSA-N (1R,2S)-2-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]butan-1-ol Chemical compound C[C@H]([C@@H](O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)CC PDDQXZBCZSODGW-YVEFUNNKSA-N 0.000 claims 1
• MQSYOBLXLDSEJB-SFHVURJKSA-N (1S)-1-(4-chlorophenyl)-2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethanol Chemical compound ClC1=CC=C(C=C1)[C@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O MQSYOBLXLDSEJB-SFHVURJKSA-N 0.000 claims 1
• PCHUEGKOMSGREH-INIZCTEOSA-N (1S)-2-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-1-ol Chemical compound CC([C@H](O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C PCHUEGKOMSGREH-INIZCTEOSA-N 0.000 claims 1
• YLESVYQTCPZCJT-HNNXBMFYSA-N (1S)-3-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]butan-1-ol Chemical compound CC(C[C@H](O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C YLESVYQTCPZCJT-HNNXBMFYSA-N 0.000 claims 1
• PDDQXZBCZSODGW-SJCJKPOMSA-N (1S,2S)-2-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]butan-1-ol Chemical compound C[C@H]([C@H](O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)CC PDDQXZBCZSODGW-SJCJKPOMSA-N 0.000 claims 1
• DOJAVRISNHIQAC-UHFFFAOYSA-N (2,6-difluorophenyl)-[2-[7-[2-(oxan-4-ylamino)pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]morpholin-4-yl]methanone Chemical compound FC1=C(C(=CC=C1)F)C(=O)N1CC(OCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 DOJAVRISNHIQAC-UHFFFAOYSA-N 0.000 claims 1
• RQVGUPMVUJZMDM-UHFFFAOYSA-N (2-fluoro-6-methoxyphenyl)-[2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]morpholin-4-yl]methanone Chemical compound FC1=C(C(=CC=C1)OC)C(=O)N1CC(OCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C RQVGUPMVUJZMDM-UHFFFAOYSA-N 0.000 claims 1
• JQXCNGPCMZCTIK-CYBMUJFWSA-N (2R)-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]butan-2-ol Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@@H](CC)O JQXCNGPCMZCTIK-CYBMUJFWSA-N 0.000 claims 1
• GWRXMFRAYRZLIU-QGZVFWFLSA-N (2R)-2-(3-fluoro-4-methoxyphenyl)-2-[7-[2-(oxan-4-ylamino)pyrimidin-4-yl]-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]ethanol Chemical compound FC=1C=C(C=CC=1OC)[C@@H](CO)C1=NN=C2N1N=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 GWRXMFRAYRZLIU-QGZVFWFLSA-N 0.000 claims 1
• DOTKNCPBHKAKEF-QGZVFWFLSA-N (2R)-2-(4-chloro-3-fluorophenyl)-2-[7-[2-(oxan-4-ylamino)pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethanol Chemical compound ClC1=C(C=C(C=C1)[C@@H](CO)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)F DOTKNCPBHKAKEF-QGZVFWFLSA-N 0.000 claims 1
• LFCXAUKDCLUQJK-MRXNPFEDSA-N (2R)-2-(4-chloro-3-fluorophenyl)-2-[7-[2-(oxan-4-ylamino)pyrimidin-4-yl]-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]ethanol Chemical compound ClC1=C(C=C(C=C1)[C@@H](CO)C1=NN=C2N1N=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)F LFCXAUKDCLUQJK-MRXNPFEDSA-N 0.000 claims 1
• HAECXPHZFJUTLK-CYBMUJFWSA-N (2R)-5,5,5-trifluoro-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]pentan-2-ol Chemical compound FC(CC[C@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O)(F)F HAECXPHZFJUTLK-CYBMUJFWSA-N 0.000 claims 1
• SXYVMLMOBGFIEU-SFHVURJKSA-N (2S)-2-(3-fluoro-4-methoxyphenyl)-2-[7-[2-(oxan-4-ylamino)pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethanol Chemical compound FC=1C=C(C=CC=1OC)[C@H](CO)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 SXYVMLMOBGFIEU-SFHVURJKSA-N 0.000 claims 1
• RRRUGOGZIHLACO-AWEZNQCLSA-N (2S)-2-[[4-[3-[(4-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound ClC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)N[C@H](CO)C)C=C1 RRRUGOGZIHLACO-AWEZNQCLSA-N 0.000 claims 1
• XVASDMZTDNROIT-LBPRGKRZSA-N (2S)-2-methyl-3-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-1-ol Chemical compound C[C@H](CO)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C XVASDMZTDNROIT-LBPRGKRZSA-N 0.000 claims 1
• HAECXPHZFJUTLK-ZDUSSCGKSA-N (2S)-5,5,5-trifluoro-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]pentan-2-ol Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(C[C@@H](O)CCC(F)(F)F)N2C=C1 HAECXPHZFJUTLK-ZDUSSCGKSA-N 0.000 claims 1
• WTJLRBQGYNOTNH-UHFFFAOYSA-N (3-chlorophenyl)-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methanol Chemical compound ClC=1C=C(C=CC=1)C(O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C WTJLRBQGYNOTNH-UHFFFAOYSA-N 0.000 claims 1
• WTJLRBQGYNOTNH-LJQANCHMSA-N (R)-(3-chlorophenyl)-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methanol Chemical compound ClC=1C=C(C=CC=1)[C@@H](O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C WTJLRBQGYNOTNH-LJQANCHMSA-N 0.000 claims 1
• YILNBPSRRRQFFH-IBGZPJMESA-N (S)-cyclohexyl-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methanol Chemical compound C1(CCCCC1)[C@H](O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YILNBPSRRRQFFH-IBGZPJMESA-N 0.000 claims 1
• NEHWYNSVQZEOER-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]propan-2-ol Chemical compound FC(C(C(F)(F)F)(O)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(F)F NEHWYNSVQZEOER-UHFFFAOYSA-N 0.000 claims 1
• VZWHGVCRZLXPGB-UHFFFAOYSA-N 1,1,1-trifluoro-3-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-2-ol Chemical compound FC(C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O)(F)F VZWHGVCRZLXPGB-UHFFFAOYSA-N 0.000 claims 1
• MQSYOBLXLDSEJB-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethanol Chemical compound ClC1=CC=C(C=C1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O MQSYOBLXLDSEJB-UHFFFAOYSA-N 0.000 claims 1
• HFSDMRLHVIDRFA-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethanol Chemical compound COC1=CC=C(C=C1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O HFSDMRLHVIDRFA-UHFFFAOYSA-N 0.000 claims 1
• DCKGCQXYDBGVTJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethanone Chemical compound COC1=CC=C(C=C1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)=O DCKGCQXYDBGVTJ-UHFFFAOYSA-N 0.000 claims 1
• OZQVMQPQHLARIU-UHFFFAOYSA-N 1-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]pyrrolidin-2-one Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CN1C(CCC1)=O OZQVMQPQHLARIU-UHFFFAOYSA-N 0.000 claims 1
• YWUNLBPMHPICPG-UHFFFAOYSA-N 1-cyclopropyl-2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethanol Chemical compound C1(CC1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O YWUNLBPMHPICPG-UHFFFAOYSA-N 0.000 claims 1
• QAOYWZPVDPRCBM-UHFFFAOYSA-N 1-cyclopropyl-3-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-2-ol Chemical compound C1(CC1)CC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O QAOYWZPVDPRCBM-UHFFFAOYSA-N 0.000 claims 1
• MWZDIEIXRBWPLG-UHFFFAOYSA-N 1-methyl-1,2,4-triazole Chemical group CN1C=NC=N1 MWZDIEIXRBWPLG-UHFFFAOYSA-N 0.000 claims 1
• IJBGHVZFWNABFP-UHFFFAOYSA-N 1-methyl-4-[[7-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]pyridin-2-one Chemical compound CN1C(C=C(C=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)=O IJBGHVZFWNABFP-UHFFFAOYSA-N 0.000 claims 1
• GBGSBAQTKVLQGL-UHFFFAOYSA-N 1-methyl-5-[7-[2-(oxan-4-ylamino)pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]-4-phenylpyrrolidin-2-one Chemical compound CN1C(CC(C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)C1=CC=CC=C1)=O GBGSBAQTKVLQGL-UHFFFAOYSA-N 0.000 claims 1
• NFOGVCOWVCTNON-UHFFFAOYSA-N 1-methyl-5-[[7-[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]pyridin-2-one Chemical compound CN1C(C=CC(=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)=O NFOGVCOWVCTNON-UHFFFAOYSA-N 0.000 claims 1
• FEHLYUULJHTBHW-UHFFFAOYSA-N 1-methyl-5-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]pyridin-2-one Chemical compound CN1C(C=CC(=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)=O FEHLYUULJHTBHW-UHFFFAOYSA-N 0.000 claims 1
• MJDHUPYFVHMKSS-UHFFFAOYSA-N 2,2-dimethyl-3-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propanenitrile Chemical compound CC(C#N)(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C MJDHUPYFVHMKSS-UHFFFAOYSA-N 0.000 claims 1
• YFLUJRDYDUQFJO-UHFFFAOYSA-N 2,4-difluoro-N-methyl-N-[2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]benzamide Chemical compound FC1=C(C(=O)N(CCC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C)C=CC(=C1)F YFLUJRDYDUQFJO-UHFFFAOYSA-N 0.000 claims 1
• LNNUOMYYMRDTDA-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethanol Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(C(O)CC3=CC=C(F)C=C3)N2C=C1 LNNUOMYYMRDTDA-UHFFFAOYSA-N 0.000 claims 1
• NTLLKQIUUCTPSM-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-1-ol Chemical compound FC1=CC=C(C=C1)C(C(O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)C NTLLKQIUUCTPSM-UHFFFAOYSA-N 0.000 claims 1
• YSUHBTDQGGGTSK-UHFFFAOYSA-N 2-cyclopropyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-2-ol Chemical compound C1(CC1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)O YSUHBTDQGGGTSK-UHFFFAOYSA-N 0.000 claims 1
• PCHUEGKOMSGREH-UHFFFAOYSA-N 2-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-1-ol Chemical compound CC(C(O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C PCHUEGKOMSGREH-UHFFFAOYSA-N 0.000 claims 1
• HUARENQYRKOCBW-UHFFFAOYSA-N 2-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-2-ol Chemical compound CC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)O HUARENQYRKOCBW-UHFFFAOYSA-N 0.000 claims 1
• BZEUGAWHYHMZCK-UHFFFAOYSA-N 3,3,4,4,4-pentafluoro-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]butan-2-ol Chemical compound FC(C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O)(C(F)(F)F)F BZEUGAWHYHMZCK-UHFFFAOYSA-N 0.000 claims 1
• MKFALEQKYOENRB-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-[7-[2-(oxan-4-ylamino)pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]propan-1-ol Chemical compound COC1=CC=C(C=C1)C(CCO)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 MKFALEQKYOENRB-UHFFFAOYSA-N 0.000 claims 1
• RHCVOLNZVVDCMP-UHFFFAOYSA-N 3-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]-1H-pyridin-2-one Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC=1C(=NC=CC=1)O RHCVOLNZVVDCMP-UHFFFAOYSA-N 0.000 claims 1
• OYDCVDQAGZLSFP-UHFFFAOYSA-N 3-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]benzonitrile Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC=1C=C(C#N)C=CC=1 OYDCVDQAGZLSFP-UHFFFAOYSA-N 0.000 claims 1
• BWIUVLRVUBAFSF-UHFFFAOYSA-N 3-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl]-1H-pyridin-2-one Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(N=C1)C(=NN=2)CC=1C(=NC=CC=1)O BWIUVLRVUBAFSF-UHFFFAOYSA-N 0.000 claims 1
• TVDUUNFOAOBDTA-UHFFFAOYSA-N 3-methyl-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]butan-2-ol Chemical compound CC(C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O)C TVDUUNFOAOBDTA-UHFFFAOYSA-N 0.000 claims 1
• MQKMGEAUJZBQJO-UHFFFAOYSA-N 4-(3-benzyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CC3=CC=CC=C3)N2C=C1 MQKMGEAUJZBQJO-UHFFFAOYSA-N 0.000 claims 1
• LDSRMUWDIUYXEG-UHFFFAOYSA-N 4-(3-benzyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound C(C1=CC=CC=C1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 LDSRMUWDIUYXEG-UHFFFAOYSA-N 0.000 claims 1
• LTJVKUKPHJFTRL-UHFFFAOYSA-N 4-(3-butyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(CCC)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C LTJVKUKPHJFTRL-UHFFFAOYSA-N 0.000 claims 1
• QFVIGALCPPOJEI-UHFFFAOYSA-N 4-(3-cyclohexyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CCCCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C QFVIGALCPPOJEI-UHFFFAOYSA-N 0.000 claims 1
• HXDVPIAYXYSYRG-UHFFFAOYSA-N 4-(3-ethyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C HXDVPIAYXYSYRG-UHFFFAOYSA-N 0.000 claims 1
• WCLNPLPERFFXLR-UHFFFAOYSA-N 4-(3-morpholin-2-yl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound N1CC(OCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 WCLNPLPERFFXLR-UHFFFAOYSA-N 0.000 claims 1
• YNQFVJZKENHMLZ-UHFFFAOYSA-N 4-[3-(1,1-difluoropropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC(CC)(F)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YNQFVJZKENHMLZ-UHFFFAOYSA-N 0.000 claims 1
• QFGXBEFFJZWTTH-UHFFFAOYSA-N 4-[3-(1,3-benzodioxol-5-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound O1COC2=C1C=CC(=C2)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 QFGXBEFFJZWTTH-UHFFFAOYSA-N 0.000 claims 1
• WMHWJCLJURBPAB-UHFFFAOYSA-N 4-[3-(1,5-dimethyl-3-phenylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound CN1N=C(C(=C1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)C1=CC=CC=C1 WMHWJCLJURBPAB-UHFFFAOYSA-N 0.000 claims 1
• SAJXTUVYPHSDHZ-UHFFFAOYSA-N 4-[3-(1,5-dimethyl-3-phenylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=C(C(=C1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C1=CC=CC=C1 SAJXTUVYPHSDHZ-UHFFFAOYSA-N 0.000 claims 1
• JTCLSVXOFYGHIK-UHFFFAOYSA-N 4-[3-(1,5-dimethyl-3-phenylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound CN1N=C(C(=C1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)C1=CC=CC=C1 JTCLSVXOFYGHIK-UHFFFAOYSA-N 0.000 claims 1
• UECWFHJNKVZLQR-UHFFFAOYSA-N 4-[3-(1-methoxy-1-phenylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound COC(C)(C1=CC=CC=C1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 UECWFHJNKVZLQR-UHFFFAOYSA-N 0.000 claims 1
• WOIXTLCWVIPJRU-UHFFFAOYSA-N 4-[3-(1-methyl-3-propan-2-ylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C(C)(C)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)C WOIXTLCWVIPJRU-UHFFFAOYSA-N 0.000 claims 1
• OEPXQCZNCPOIAG-UHFFFAOYSA-N 4-[3-(1-methyl-5-propan-2-ylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C(C)(C)C1=C(C=NN1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C OEPXQCZNCPOIAG-UHFFFAOYSA-N 0.000 claims 1
• LEHKAKPERCYXIQ-UHFFFAOYSA-N 4-[3-(2,2-difluoropropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)F LEHKAKPERCYXIQ-UHFFFAOYSA-N 0.000 claims 1
• ORZICZYNISOVPX-UHFFFAOYSA-N 4-[3-(2,2-dimethylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CCC(C)(C)CC1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1 ORZICZYNISOVPX-UHFFFAOYSA-N 0.000 claims 1
• OIJKTGDUWHZJQF-UHFFFAOYSA-N 4-[3-(2,2-dimethylcyclopropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CC1(C(C1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C OIJKTGDUWHZJQF-UHFFFAOYSA-N 0.000 claims 1
• QOQBAMGJVQOULR-UHFFFAOYSA-N 4-[3-(2,2-dimethylpropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC(C)(C)C QOQBAMGJVQOULR-UHFFFAOYSA-N 0.000 claims 1
• HETUOTJLMKLFJP-UHFFFAOYSA-N 4-[3-(2,2-dimethylpropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(C)(C)C HETUOTJLMKLFJP-UHFFFAOYSA-N 0.000 claims 1
• OKCGXWQETPXKCH-UHFFFAOYSA-N 4-[3-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound O1C2=C(OCC1)C=C(C=C2)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 OKCGXWQETPXKCH-UHFFFAOYSA-N 0.000 claims 1
• JBYYWQOVYMDGKQ-UHFFFAOYSA-N 4-[3-(2,3-dimethylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CC(C)C(C)CC1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1 JBYYWQOVYMDGKQ-UHFFFAOYSA-N 0.000 claims 1
• FALNNGJRHHWDMN-UHFFFAOYSA-N 4-[3-(2,3-dimethylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methyltriazol-4-yl)pyrimidin-2-amine Chemical compound CC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=NN(N=C1)C)C(C)C FALNNGJRHHWDMN-UHFFFAOYSA-N 0.000 claims 1
• VDSHVOFEXUQLPE-UHFFFAOYSA-N 4-[3-(2-amino-1-phenylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound NCC(C1=CC=CC=C1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 VDSHVOFEXUQLPE-UHFFFAOYSA-N 0.000 claims 1
• KUOINAJMKNXIEF-UHFFFAOYSA-N 4-[3-(2-bicyclo[2.2.1]heptanylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C12C(CC(CC1)C2)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C KUOINAJMKNXIEF-UHFFFAOYSA-N 0.000 claims 1
• IAGVPVLAZOMGDO-UHFFFAOYSA-N 4-[3-(2-chloro-4-fluorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=C(C=CC(=C1)F)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 IAGVPVLAZOMGDO-UHFFFAOYSA-N 0.000 claims 1
• WFWLETSYHLTEGF-UHFFFAOYSA-N 4-[3-(2-cyclohexylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CCCCC1)CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C WFWLETSYHLTEGF-UHFFFAOYSA-N 0.000 claims 1
• DTOUYVQFZJBHBV-UHFFFAOYSA-N 4-[3-(2-cyclopentyl-3,3,3-trifluoropropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CCCC1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C(F)(F)F DTOUYVQFZJBHBV-UHFFFAOYSA-N 0.000 claims 1
• JJDXVVUEKQPDHL-UHFFFAOYSA-N 4-[3-(2-cyclopentylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CCCC1)CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C JJDXVVUEKQPDHL-UHFFFAOYSA-N 0.000 claims 1
• MRLUTUDPDVMKRG-UHFFFAOYSA-N 4-[3-(2-cyclopropyl-3,3,3-trifluoropropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound C1(CC1)C(CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C)C(F)(F)F MRLUTUDPDVMKRG-UHFFFAOYSA-N 0.000 claims 1
• QIAQSBVXMAEIFG-UHFFFAOYSA-N 4-[3-(2-cyclopropyl-3,3,3-trifluoropropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C(F)(F)F QIAQSBVXMAEIFG-UHFFFAOYSA-N 0.000 claims 1
• JQLGTOJTXAZOKE-UHFFFAOYSA-N 4-[3-(2-cyclopropylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C JQLGTOJTXAZOKE-UHFFFAOYSA-N 0.000 claims 1
• QCVWRXSBKVVAEG-UHFFFAOYSA-N 4-[3-(2-ethoxy-3,3,3-trifluoropropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CCOC(CC1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1)C(F)(F)F QCVWRXSBKVVAEG-UHFFFAOYSA-N 0.000 claims 1
• CIXWCNQXLCUFIJ-UHFFFAOYSA-N 4-[3-(2-ethoxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CCOCCC1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1 CIXWCNQXLCUFIJ-UHFFFAOYSA-N 0.000 claims 1
• FGKKGAJSYLOCKZ-UHFFFAOYSA-N 4-[3-(2-ethylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C(C)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)CC FGKKGAJSYLOCKZ-UHFFFAOYSA-N 0.000 claims 1
• SGVXVNFOCGSPEY-UHFFFAOYSA-N 4-[3-(2-ethylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)CC SGVXVNFOCGSPEY-UHFFFAOYSA-N 0.000 claims 1
• HMPSGSLKEQBXRY-UHFFFAOYSA-N 4-[3-(2-ethylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methyltriazol-4-yl)pyrimidin-2-amine Chemical compound C(C)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=NN(N=C1)C)CC HMPSGSLKEQBXRY-UHFFFAOYSA-N 0.000 claims 1
• XABQKAPJNAZNGK-UHFFFAOYSA-N 4-[3-(2-methoxybutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)CC XABQKAPJNAZNGK-UHFFFAOYSA-N 0.000 claims 1
• CGAJJFMUNPEVNF-UHFFFAOYSA-N 4-[3-(2-methoxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COCCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C CGAJJFMUNPEVNF-UHFFFAOYSA-N 0.000 claims 1
• YSZDZSKZYUJCDE-UHFFFAOYSA-N 4-[3-(2-methoxypropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C YSZDZSKZYUJCDE-UHFFFAOYSA-N 0.000 claims 1
• FNZOMWAMDYDITF-UHFFFAOYSA-N 4-[3-(2-methylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methyl-1,2,4-triazol-3-yl)pyridin-2-amine Chemical compound CN1N=CN=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC(CC)C FNZOMWAMDYDITF-UHFFFAOYSA-N 0.000 claims 1
• IWTRITXULWBPPK-UHFFFAOYSA-N 4-[3-(2-methylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC(CC)C IWTRITXULWBPPK-UHFFFAOYSA-N 0.000 claims 1
• HTKPZAOAXWRERY-UHFFFAOYSA-N 4-[3-(2-methylcyclopropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C1C(C1)C HTKPZAOAXWRERY-UHFFFAOYSA-N 0.000 claims 1
• VFOBGZJQBMJPTD-UHFFFAOYSA-N 4-[3-(2-methylpentyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(CCC)C VFOBGZJQBMJPTD-UHFFFAOYSA-N 0.000 claims 1
• UIBMAKUCYCTYAF-UHFFFAOYSA-N 4-[3-(2-methylpropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C(C(C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C UIBMAKUCYCTYAF-UHFFFAOYSA-N 0.000 claims 1
• MVSXWSMJBMDZAS-UHFFFAOYSA-N 4-[3-(2-methylpropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound C(C(C)C)C1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C MVSXWSMJBMDZAS-UHFFFAOYSA-N 0.000 claims 1
• GOGKUESPEQRZKX-UHFFFAOYSA-N 4-[3-(2-methylpropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C(C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C GOGKUESPEQRZKX-UHFFFAOYSA-N 0.000 claims 1
• XPSRMXXXGXLGHC-UHFFFAOYSA-N 4-[3-(2-methylpropyl)-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C(C)C)C1=NN=C2N1N=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C XPSRMXXXGXLGHC-UHFFFAOYSA-N 0.000 claims 1
• PRKKLSSMWKXXFB-UHFFFAOYSA-N 4-[3-(2-methylpropylsulfanylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C(C)C)SCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C PRKKLSSMWKXXFB-UHFFFAOYSA-N 0.000 claims 1
• YWAQPEXDJQHWSB-UHFFFAOYSA-N 4-[3-(3,3-dimethylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CC(CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)C YWAQPEXDJQHWSB-UHFFFAOYSA-N 0.000 claims 1
• HVYXACSSJYYGDU-UHFFFAOYSA-N 4-[3-(3,4-dihydro-1H-isochromen-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(OCCC2=CC=CC=C12)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C HVYXACSSJYYGDU-UHFFFAOYSA-N 0.000 claims 1
• YQEOROYCOKPGCW-UHFFFAOYSA-N 4-[3-(3-methyl-5-phenyl-1,2-oxazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound CC1=NOC(=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)C1=CC=CC=C1 YQEOROYCOKPGCW-UHFFFAOYSA-N 0.000 claims 1
• ACIHKFRZLVRQEW-UHFFFAOYSA-N 4-[3-(3-methylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(CC(C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C ACIHKFRZLVRQEW-UHFFFAOYSA-N 0.000 claims 1
• UZUKVXLECGVNTB-UHFFFAOYSA-N 4-[3-(3-methylpentyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CCC(CC)C UZUKVXLECGVNTB-UHFFFAOYSA-N 0.000 claims 1
• RKAQUOXVVFAYKW-UHFFFAOYSA-N 4-[3-(4-methoxyphenoxy)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=CC=C(OC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C1 RKAQUOXVVFAYKW-UHFFFAOYSA-N 0.000 claims 1
• QWYBFLATAWEXDI-UHFFFAOYSA-N 4-[3-(4-methylpentyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CCCC(C)C QWYBFLATAWEXDI-UHFFFAOYSA-N 0.000 claims 1
• OUFBAMMDXDSMBS-UHFFFAOYSA-N 4-[3-(azepan-1-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound N1(CCCCCC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C OUFBAMMDXDSMBS-UHFFFAOYSA-N 0.000 claims 1
• DZXXYPVFXZEICC-UHFFFAOYSA-N 4-[3-(benzenesulfinylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CS(=O)C1=CC=CC=C1 DZXXYPVFXZEICC-UHFFFAOYSA-N 0.000 claims 1
• FWAOADVRPWAWKG-UHFFFAOYSA-N 4-[3-(benzenesulfonylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CS(=O)(=O)C1=CC=CC=C1 FWAOADVRPWAWKG-UHFFFAOYSA-N 0.000 claims 1
• JEQDBBCWMDNCDN-UHFFFAOYSA-N 4-[3-(benzylsulfanylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CSCC3=CC=CC=C3)N2C=C1 JEQDBBCWMDNCDN-UHFFFAOYSA-N 0.000 claims 1
• OFPLXZAKRLBZEK-UHFFFAOYSA-N 4-[3-(cyclohexylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound C1(CCCCC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 OFPLXZAKRLBZEK-UHFFFAOYSA-N 0.000 claims 1
• XRLSQRADOPDJEQ-UHFFFAOYSA-N 4-[3-(cyclopentylsulfanylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CCCC1)SCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C XRLSQRADOPDJEQ-UHFFFAOYSA-N 0.000 claims 1
• IZPBSJJZWOZCIC-UHFFFAOYSA-N 4-[3-(diethylaminomethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)N(CC)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C IZPBSJJZWOZCIC-UHFFFAOYSA-N 0.000 claims 1
• PPUIEERHYAIPNU-UHFFFAOYSA-N 4-[3-(tert-butylsulfanylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)(C)(C)SCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C PPUIEERHYAIPNU-UHFFFAOYSA-N 0.000 claims 1
• JSYZCWDJLYNANX-UHFFFAOYSA-N 4-[3-[(1-benzylimidazol-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C1=CC=CC=C1)N1C(=NC=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C JSYZCWDJLYNANX-UHFFFAOYSA-N 0.000 claims 1
• RVTIMVRGFYQXIV-UHFFFAOYSA-N 4-[3-[(1-cyclopropyl-3,5-dimethylpyrazol-4-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)N1N=C(C(=C1C)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C RVTIMVRGFYQXIV-UHFFFAOYSA-N 0.000 claims 1
• QZTKIWRRZDZIHC-UHFFFAOYSA-N 4-[3-[(1-cyclopropylcyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound C1(CC1)(C1CC1)CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C QZTKIWRRZDZIHC-UHFFFAOYSA-N 0.000 claims 1
• BJRLZWBHRJJXKD-UHFFFAOYSA-N 4-[3-[(1-cyclopropylcyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)(C1CC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C BJRLZWBHRJJXKD-UHFFFAOYSA-N 0.000 claims 1
• OPVQOQAHNJGTRL-UHFFFAOYSA-N 4-[3-[(1-cyclopropylcyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound C1(CC1)(C1CC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 OPVQOQAHNJGTRL-UHFFFAOYSA-N 0.000 claims 1
• BJEKPRIOTNCLLU-UHFFFAOYSA-N 4-[3-[(1-ethoxycyclobutyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)OC1(CCC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C BJEKPRIOTNCLLU-UHFFFAOYSA-N 0.000 claims 1
• PPDIVHROFFFHJM-UHFFFAOYSA-N 4-[3-[(1-ethylcyclobutyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)C1(CCC1)CC1=NN=C2N1C=CC(=C2)C2=NC(=NC=C2)NC2=CC=NN2C PPDIVHROFFFHJM-UHFFFAOYSA-N 0.000 claims 1
• OPBJXLMDRZNHHD-UHFFFAOYSA-N 4-[3-[(1-ethylcyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound C(C)C1(CC1)CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C OPBJXLMDRZNHHD-UHFFFAOYSA-N 0.000 claims 1
• GSIREHJCSOIENB-UHFFFAOYSA-N 4-[3-[(1-ethylcyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CCC1(CC2=NN=C3C=C(C=CN23)C2=CC=NC(NC3=CC=NN3C)=N2)CC1 GSIREHJCSOIENB-UHFFFAOYSA-N 0.000 claims 1
• HBDRBOQZTZRKQQ-UHFFFAOYSA-N 4-[3-[(1-methylcyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CC3(C)CC3)N2C=C1 HBDRBOQZTZRKQQ-UHFFFAOYSA-N 0.000 claims 1
• BSZIUFPGKNRCSJ-UHFFFAOYSA-N 4-[3-[(1-methylimidazol-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1C(=NC=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C BSZIUFPGKNRCSJ-UHFFFAOYSA-N 0.000 claims 1
• JLLLSQRVLHFLHF-CYBMUJFWSA-N 4-[3-[(1R)-1-[(2-methylpropan-2-yl)oxy]ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)(C)(C)O[C@H](C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C JLLLSQRVLHFLHF-CYBMUJFWSA-N 0.000 claims 1
• IPBIBKSYUSWTMG-QGZVFWFLSA-N 4-[3-[(1R)-1-methoxy-2-methylpropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CO[C@H](C(C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C IPBIBKSYUSWTMG-QGZVFWFLSA-N 0.000 claims 1
• YEFLFMASXKLBOH-LJQANCHMSA-N 4-[3-[(1R)-1-methoxy-2-phenylethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CO[C@H](CC1=CC=CC=C1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YEFLFMASXKLBOH-LJQANCHMSA-N 0.000 claims 1
• JLLLSQRVLHFLHF-ZDUSSCGKSA-N 4-[3-[(1S)-1-[(2-methylpropan-2-yl)oxy]ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C[C@H](OC(C)(C)C)C1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1 JLLLSQRVLHFLHF-ZDUSSCGKSA-N 0.000 claims 1
• IPBIBKSYUSWTMG-KRWDZBQOSA-N 4-[3-[(1S)-1-methoxy-2-methylpropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CO[C@@H](C(C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C IPBIBKSYUSWTMG-KRWDZBQOSA-N 0.000 claims 1
• BXQRQKBPNMLWOE-UHFFFAOYSA-N 4-[3-[(2,2-difluorocyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1(C(C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F BXQRQKBPNMLWOE-UHFFFAOYSA-N 0.000 claims 1
• COVXXZJVDUTGJC-UHFFFAOYSA-N 4-[3-[(2,3-dichlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=C1Cl COVXXZJVDUTGJC-UHFFFAOYSA-N 0.000 claims 1
• HIKQCFMSFZEORU-UHFFFAOYSA-N 4-[3-[(2,3-difluoro-4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound COC1=C(F)C(F)=C(CC2=NN=C3C=C(C=CN23)C2=CC(NC3=CC=NN3C)=NC=C2)C=C1 HIKQCFMSFZEORU-UHFFFAOYSA-N 0.000 claims 1
• HPIVPHCFPPVKQP-UHFFFAOYSA-N 4-[3-[(2,3-difluoro-4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC(=C1F)OC HPIVPHCFPPVKQP-UHFFFAOYSA-N 0.000 claims 1
• WJILPPSNFYZZAO-UHFFFAOYSA-N 4-[3-[(2,3-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=CC=NN2C)C=CC=C1F WJILPPSNFYZZAO-UHFFFAOYSA-N 0.000 claims 1
• FPKVBXCCWCQTCF-UHFFFAOYSA-N 4-[3-[(2,3-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=C1F FPKVBXCCWCQTCF-UHFFFAOYSA-N 0.000 claims 1
• TUUDOMJYMJYRLP-UHFFFAOYSA-N 4-[3-[(2,3-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methyltriazol-4-yl)pyrimidin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=NN(N=C2)C)C=CC=C1F TUUDOMJYMJYRLP-UHFFFAOYSA-N 0.000 claims 1
• JARHGUCJLVQHEQ-UHFFFAOYSA-N 4-[3-[(2,4-dichlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC(=C1)Cl JARHGUCJLVQHEQ-UHFFFAOYSA-N 0.000 claims 1
• MMJZQFMLRKUYMU-UHFFFAOYSA-N 4-[3-[(2,4-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=CC=NN2C)C=CC(=C1)F MMJZQFMLRKUYMU-UHFFFAOYSA-N 0.000 claims 1
• IBRJQXXXOXCLIZ-UHFFFAOYSA-N 4-[3-[(2,4-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC(=C1)F IBRJQXXXOXCLIZ-UHFFFAOYSA-N 0.000 claims 1
• JSQYLISTRAGZJP-UHFFFAOYSA-N 4-[3-[(2,5-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C(C=C1)F JSQYLISTRAGZJP-UHFFFAOYSA-N 0.000 claims 1
• GUYRZEZVRPXDJK-UHFFFAOYSA-N 4-[3-[(2,5-dimethylpyrazol-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=C(C=C1CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C GUYRZEZVRPXDJK-UHFFFAOYSA-N 0.000 claims 1
• RUBKRLOBXKQSPZ-UHFFFAOYSA-N 4-[3-[(2,6-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C(=CC=C1)F RUBKRLOBXKQSPZ-UHFFFAOYSA-N 0.000 claims 1
• SIQAVFUALMKDNV-UHFFFAOYSA-N 4-[3-[(2-chloro-6-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C(=CC=C1)F SIQAVFUALMKDNV-UHFFFAOYSA-N 0.000 claims 1
• OREVUBBFFXAMOD-UHFFFAOYSA-N 4-[3-[(2-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound ClC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C=CC=C1 OREVUBBFFXAMOD-UHFFFAOYSA-N 0.000 claims 1
• BUCSBBXRORSWOO-UHFFFAOYSA-N 4-[3-[(2-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=C1 BUCSBBXRORSWOO-UHFFFAOYSA-N 0.000 claims 1
• AKFHRXIMZCGHAS-UHFFFAOYSA-N 4-[3-[(2-chloropyridin-3-yl)methyl]-8-fluoro-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyridin-2-amine Chemical compound ClC1=NC=CC=C1CC1=NN=C2N1C=CC(=C2F)C1=CC(=NC=C1)NC1CCOCC1 AKFHRXIMZCGHAS-UHFFFAOYSA-N 0.000 claims 1
• XHKOUYKREDYPLF-UHFFFAOYSA-N 4-[3-[(2-chloropyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound ClC1=NC=CC=C1CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C XHKOUYKREDYPLF-UHFFFAOYSA-N 0.000 claims 1
• UQRPUOPKEWNJNL-UHFFFAOYSA-N 4-[3-[(2-chloropyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=NC=CC=C1CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 UQRPUOPKEWNJNL-UHFFFAOYSA-N 0.000 claims 1
• VHWXRTKVWNMTTR-UHFFFAOYSA-N 4-[3-[(2-chloropyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-propan-2-ylpyrimidin-2-amine Chemical compound ClC1=NC=CC=C1CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC(C)C VHWXRTKVWNMTTR-UHFFFAOYSA-N 0.000 claims 1
• OJRACSPCHOOJMS-UHFFFAOYSA-N 4-[3-[(2-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=C1 OJRACSPCHOOJMS-UHFFFAOYSA-N 0.000 claims 1
• QQPJPGZABSQSJD-UHFFFAOYSA-N 4-[3-[(2-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-propan-2-ylpyrimidin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC(C)C)C=CC=C1 QQPJPGZABSQSJD-UHFFFAOYSA-N 0.000 claims 1
• UKZVEYMRPLWZHR-UHFFFAOYSA-N 4-[3-[(2-fluorophenyl)sulfanylmethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CSC3=C(F)C=CC=C3)N2C=C1 UKZVEYMRPLWZHR-UHFFFAOYSA-N 0.000 claims 1
• SXTOVOHAPXBIHK-UHFFFAOYSA-N 4-[3-[(2-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=C1 SXTOVOHAPXBIHK-UHFFFAOYSA-N 0.000 claims 1
• WGWUGCNZORMBNV-UHFFFAOYSA-N 4-[3-[(2-methoxypyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound COC1=NC=CC=C1CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C WGWUGCNZORMBNV-UHFFFAOYSA-N 0.000 claims 1
• SDJKCKPUXADHPU-UHFFFAOYSA-N 4-[3-[(2-methoxypyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound COC1=NC=CC=C1CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C SDJKCKPUXADHPU-UHFFFAOYSA-N 0.000 claims 1
• YKVNJBWKEATHFT-UHFFFAOYSA-N 4-[3-[(2-methoxypyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=NC=CC=C1CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YKVNJBWKEATHFT-UHFFFAOYSA-N 0.000 claims 1
• FLMJRRHATGUPIF-UHFFFAOYSA-N 4-[3-[(2-methoxypyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound COC1=NC=CC=C1CC1=NN=C2C=C(C=CN12)C1=NC(NC2CCOCC2)=NC=C1 FLMJRRHATGUPIF-UHFFFAOYSA-N 0.000 claims 1
• JHYAJWBPDOLULJ-UHFFFAOYSA-N 4-[3-[(2-methoxypyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=NC=CC=C1CC1=NN=C2N1N=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C JHYAJWBPDOLULJ-UHFFFAOYSA-N 0.000 claims 1
• IWIMOJLFQRLWME-UHFFFAOYSA-N 4-[3-[(2-methylphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=C(C=CC=C1)C IWIMOJLFQRLWME-UHFFFAOYSA-N 0.000 claims 1
• FPHFKACAJPRMIW-UHFFFAOYSA-N 4-[3-[(2-methylpiperidin-1-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CN1C(CCCC1)C FPHFKACAJPRMIW-UHFFFAOYSA-N 0.000 claims 1
• ITKYKSODZIUTMF-UHFFFAOYSA-N 4-[3-[(2-methylpropan-2-yl)oxymethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)(C)(C)OCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C ITKYKSODZIUTMF-UHFFFAOYSA-N 0.000 claims 1
• SSNNMYUIIAJKNU-LJQANCHMSA-N 4-[3-[(2R)-2-(4-chlorophenyl)-2-methoxyethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)[C@@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)OC SSNNMYUIIAJKNU-LJQANCHMSA-N 0.000 claims 1
• QIAQSBVXMAEIFG-CQSZACIVSA-N 4-[3-[(2R)-2-cyclopropyl-3,3,3-trifluoropropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)[C@@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C(F)(F)F QIAQSBVXMAEIFG-CQSZACIVSA-N 0.000 claims 1
• IMYRHVKHGDGDDU-MRXNPFEDSA-N 4-[3-[(2R)-2-methoxy-3-methylbutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CO[C@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C(C)C IMYRHVKHGDGDDU-MRXNPFEDSA-N 0.000 claims 1
• WGSBDIQMYFPTHY-LJQANCHMSA-N 4-[3-[(2R)-4-cyclopropyl-2-methoxybutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound C1(CC1)CC[C@H](CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C)OC WGSBDIQMYFPTHY-LJQANCHMSA-N 0.000 claims 1
• UEAWPOCUBRSJLK-QGZVFWFLSA-N 4-[3-[(2R)-4-cyclopropyl-2-methoxybutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)CC[C@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)OC UEAWPOCUBRSJLK-QGZVFWFLSA-N 0.000 claims 1
• SSNNMYUIIAJKNU-IBGZPJMESA-N 4-[3-[(2S)-2-(4-chlorophenyl)-2-methoxyethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)[C@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)OC SSNNMYUIIAJKNU-IBGZPJMESA-N 0.000 claims 1
• QIAQSBVXMAEIFG-AWEZNQCLSA-N 4-[3-[(2S)-2-cyclopropyl-3,3,3-trifluoropropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)[C@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C(F)(F)F QIAQSBVXMAEIFG-AWEZNQCLSA-N 0.000 claims 1
• IMYRHVKHGDGDDU-INIZCTEOSA-N 4-[3-[(2S)-2-methoxy-3-methylbutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CO[C@@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C(C)C IMYRHVKHGDGDDU-INIZCTEOSA-N 0.000 claims 1
• ONWYGCVXIAJCQB-LBPRGKRZSA-N 4-[3-[(2S)-2-methylbutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methyltriazol-4-yl)pyrimidin-2-amine Chemical compound CN1N=CC(=N1)NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@H](CC)C ONWYGCVXIAJCQB-LBPRGKRZSA-N 0.000 claims 1
• ZQJLWEZTDZLOMI-AWEZNQCLSA-N 4-[3-[(2S)-2-methylbutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound C[C@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)CC ZQJLWEZTDZLOMI-AWEZNQCLSA-N 0.000 claims 1
• WGSBDIQMYFPTHY-IBGZPJMESA-N 4-[3-[(2S)-4-cyclopropyl-2-methoxybutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound C1(CC1)CC[C@@H](CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C)OC WGSBDIQMYFPTHY-IBGZPJMESA-N 0.000 claims 1
• UEAWPOCUBRSJLK-KRWDZBQOSA-N 4-[3-[(2S)-4-cyclopropyl-2-methoxybutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)CC[C@@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)OC UEAWPOCUBRSJLK-KRWDZBQOSA-N 0.000 claims 1
• FFVKAFVCDYLJHY-UHFFFAOYSA-N 4-[3-[(3,3-difluorocyclobutyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1(CC(C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F FFVKAFVCDYLJHY-UHFFFAOYSA-N 0.000 claims 1
• FJLHBVGIEWFZEE-UHFFFAOYSA-N 4-[3-[(3,4-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=1F FJLHBVGIEWFZEE-UHFFFAOYSA-N 0.000 claims 1
• XZRFTFLEPFUHLI-UHFFFAOYSA-N 4-[3-[(3,5-difluoro-4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C(C=1OC)F XZRFTFLEPFUHLI-UHFFFAOYSA-N 0.000 claims 1
• WLVQHZVWWVMMGT-UHFFFAOYSA-N 4-[3-[(3,5-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=CC=NN2C)C=C(C=1)F WLVQHZVWWVMMGT-UHFFFAOYSA-N 0.000 claims 1
• DMZZMZNMZHQYMS-UHFFFAOYSA-N 4-[3-[(3,5-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C(C=1)F DMZZMZNMZHQYMS-UHFFFAOYSA-N 0.000 claims 1
• ICFUDNJNYVEMLX-UHFFFAOYSA-N 4-[3-[(3-chloro-4-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C=CC=1F ICFUDNJNYVEMLX-UHFFFAOYSA-N 0.000 claims 1
• HGGLFOVYPXTWCN-UHFFFAOYSA-N 4-[3-[(3-chloro-4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C=CC=1OC HGGLFOVYPXTWCN-UHFFFAOYSA-N 0.000 claims 1
• YXVBIARKMWDUPT-UHFFFAOYSA-N 4-[3-[(3-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C=CC=1 YXVBIARKMWDUPT-UHFFFAOYSA-N 0.000 claims 1
• QWONIOFZERHUEL-UHFFFAOYSA-N 4-[3-[(3-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methyl-1,2,4-triazol-3-yl)pyridin-2-amine Chemical compound ClC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=NC=NN2C)C=CC=1 QWONIOFZERHUEL-UHFFFAOYSA-N 0.000 claims 1
• WHSYWZWXUGCJLJ-UHFFFAOYSA-N 4-[3-[(3-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound ClC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=CC=NN2C)C=CC=1 WHSYWZWXUGCJLJ-UHFFFAOYSA-N 0.000 claims 1
• COGBFOBAFUYCDL-UHFFFAOYSA-N 4-[3-[(3-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=1 COGBFOBAFUYCDL-UHFFFAOYSA-N 0.000 claims 1
• RRKVDGDUANXKFK-UHFFFAOYSA-N 4-[3-[(3-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(CC2=NN=C3N2N=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=1 RRKVDGDUANXKFK-UHFFFAOYSA-N 0.000 claims 1
• PCDWGZQXDBCXLW-UHFFFAOYSA-N 4-[3-[(3-chloropyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound ClC=1C(=NC=CC=1)CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C PCDWGZQXDBCXLW-UHFFFAOYSA-N 0.000 claims 1
• RAKOFEGZTYFOJN-UHFFFAOYSA-N 4-[3-[(3-chloropyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C(=NC=CC=1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C RAKOFEGZTYFOJN-UHFFFAOYSA-N 0.000 claims 1
• CZDWASWDPAECNT-UHFFFAOYSA-N 4-[3-[(3-chloropyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC=1C(=NC=CC=1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 CZDWASWDPAECNT-UHFFFAOYSA-N 0.000 claims 1
• BUYNRXOYDFJIIN-UHFFFAOYSA-N 4-[3-[(3-cyclopropylphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C=1C=C(CC2=NN=C3N2C=CC(=C3)C3=NC(=NC=C3)NC3=CC=NN3C)C=CC1 BUYNRXOYDFJIIN-UHFFFAOYSA-N 0.000 claims 1
• BBTNWJHNEBZVRJ-UHFFFAOYSA-N 4-[3-[(3-cyclopropylpyrazol-1-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C1=NN(C=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C BBTNWJHNEBZVRJ-UHFFFAOYSA-N 0.000 claims 1
• BDSYKAQKGLGQPM-UHFFFAOYSA-N 4-[3-[(3-ethyloxetan-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)C1(COC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C BDSYKAQKGLGQPM-UHFFFAOYSA-N 0.000 claims 1
• GJEOOCSZWZDUCW-UHFFFAOYSA-N 4-[3-[(3-fluoro-4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C=CC=1OC GJEOOCSZWZDUCW-UHFFFAOYSA-N 0.000 claims 1
• GJSNWZRTBVFHHT-UHFFFAOYSA-N 4-[3-[(3-fluoro-4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-propan-2-ylpyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC(C)C)C=CC=1OC GJSNWZRTBVFHHT-UHFFFAOYSA-N 0.000 claims 1
• IWUDRZFLEHSQPE-UHFFFAOYSA-N 4-[3-[(3-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C=CC=1 IWUDRZFLEHSQPE-UHFFFAOYSA-N 0.000 claims 1
• YLUDNNYDJNMUKU-UHFFFAOYSA-N 4-[3-[(3-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=1 YLUDNNYDJNMUKU-UHFFFAOYSA-N 0.000 claims 1
• AMAZXNWURUWXTN-UHFFFAOYSA-N 4-[3-[(3-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=1 AMAZXNWURUWXTN-UHFFFAOYSA-N 0.000 claims 1
• IDECWAOQNIFFAJ-IZZNHLLZSA-N 4-[3-[(3S,4R)-1-benzyl-4-(3-fluorophenyl)pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C1=CC=CC=C1)N1C[C@H]([C@@H](C1)C1=CC(=CC=C1)F)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C IDECWAOQNIFFAJ-IZZNHLLZSA-N 0.000 claims 1
• FYGWCSNMULRIRT-WUFINQPMSA-N 4-[3-[(3S,4R)-1-benzyl-4-(3-fluorophenyl)pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound C(C1=CC=CC=C1)N1C[C@H]([C@@H](C1)C1=CC(=CC=C1)F)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 FYGWCSNMULRIRT-WUFINQPMSA-N 0.000 claims 1
• AJJFIHGKBOJTCB-RBUKOAKNSA-N 4-[3-[(3S,4R)-4-(4-chloro-3-fluorophenyl)pyrrolidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=C(C=C(C=C1)[C@H]1[C@@H](CNC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)F AJJFIHGKBOJTCB-RBUKOAKNSA-N 0.000 claims 1
• VNKSDVRDTDLYII-UHFFFAOYSA-N 4-[3-[(4,4-difluorocyclohexyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1(CCC(CC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F VNKSDVRDTDLYII-UHFFFAOYSA-N 0.000 claims 1
• XTRQXYQOOHROKT-UHFFFAOYSA-N 4-[3-[(4,4-difluorocyclohexyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methyltriazol-4-yl)pyrimidin-2-amine Chemical compound FC1(CCC(CC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=NN(N=C1)C)F XTRQXYQOOHROKT-UHFFFAOYSA-N 0.000 claims 1
• KFHFXVUSAYESMP-UHFFFAOYSA-N 4-[3-[(4,4-dimethyloxolan-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CC1(CC(OC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C KFHFXVUSAYESMP-UHFFFAOYSA-N 0.000 claims 1
• PDTQQQQNXUNKJX-UHFFFAOYSA-N 4-[3-[(4-bromopyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound BrC1=CC(=NC=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C PDTQQQQNXUNKJX-UHFFFAOYSA-N 0.000 claims 1
• COOJTMWIGVGMLS-UHFFFAOYSA-N 4-[3-[(4-chloro-3-fluorophenyl)methyl]-8-fluoro-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyridin-2-amine Chemical compound ClC1=C(C=C(CC2=NN=C3N2C=CC(=C3F)C2=CC(=NC=C2)NC2CCOCC2)C=C1)F COOJTMWIGVGMLS-UHFFFAOYSA-N 0.000 claims 1
• HFBIXYKNQBMNRP-UHFFFAOYSA-N 4-[3-[(4-chloro-3-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=C(C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C=C1)F HFBIXYKNQBMNRP-UHFFFAOYSA-N 0.000 claims 1
• VURYAAUYVRYUOG-UHFFFAOYSA-N 4-[3-[(4-chloro-3-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-propan-2-ylpyrimidin-2-amine Chemical compound ClC1=C(C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC(C)C)C=C1)F VURYAAUYVRYUOG-UHFFFAOYSA-N 0.000 claims 1
• WNCFVUKDNODZSR-UHFFFAOYSA-N 4-[3-[(4-chlorophenyl)-difluoromethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C(C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)(F)F WNCFVUKDNODZSR-UHFFFAOYSA-N 0.000 claims 1
• BOTMULLUNROMFN-UHFFFAOYSA-N 4-[3-[(4-chlorophenyl)methyl]-8-fluoro-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyridin-2-amine Chemical compound FC1=C(C=CN2C(CC3=CC=C(Cl)C=C3)=NN=C12)C1=CC(NC2CCOCC2)=NC=C1 BOTMULLUNROMFN-UHFFFAOYSA-N 0.000 claims 1
• GJTZUVHUVQDKPM-UHFFFAOYSA-N 4-[3-[(4-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyridin-2-amine Chemical compound ClC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC=2C=NN(C=2)C)C=C1 GJTZUVHUVQDKPM-UHFFFAOYSA-N 0.000 claims 1
• RMIYNIIWICMNCX-UHFFFAOYSA-N 4-[3-[(4-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C=C1 RMIYNIIWICMNCX-UHFFFAOYSA-N 0.000 claims 1
• DSHCQGCFUFKGMX-UHFFFAOYSA-N 4-[3-[(4-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methyl-1,2,4-triazol-3-yl)pyridin-2-amine Chemical compound ClC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=NC=NN2C)C=C1 DSHCQGCFUFKGMX-UHFFFAOYSA-N 0.000 claims 1
• JHMNRAUJMPBOOO-UHFFFAOYSA-N 4-[3-[(4-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC2=NN=C(CC3=CC=C(Cl)C=C3)N2C=C1 JHMNRAUJMPBOOO-UHFFFAOYSA-N 0.000 claims 1
• ZHYLYYXLMFIALQ-UHFFFAOYSA-N 4-[3-[(4-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C1 ZHYLYYXLMFIALQ-UHFFFAOYSA-N 0.000 claims 1
• MEIPXVVXPLZTES-UHFFFAOYSA-N 4-[3-[(4-chlorophenyl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(CC2=NN=C3N2N=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C1 MEIPXVVXPLZTES-UHFFFAOYSA-N 0.000 claims 1
• NGXJUQQJBKAQSB-UHFFFAOYSA-N 4-[3-[(4-cyclopropyl-3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C1=C(C(=NC=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F NGXJUQQJBKAQSB-UHFFFAOYSA-N 0.000 claims 1
• GKWRTUIXQMRDAM-UHFFFAOYSA-N 4-[3-[(4-cyclopropyl-6-methylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C1=CC(=NC(=C1)C)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C GKWRTUIXQMRDAM-UHFFFAOYSA-N 0.000 claims 1
• XBSGHPSZNHWAIX-UHFFFAOYSA-N 4-[3-[(4-cyclopropylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CC3=NC=CC(=C3)C3CC3)N2C=C1 XBSGHPSZNHWAIX-UHFFFAOYSA-N 0.000 claims 1
• MKTVXPVPGTWBBX-UHFFFAOYSA-N 4-[3-[(4-ethoxy-2,3-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)OC1=C(C(=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C1)F)F MKTVXPVPGTWBBX-UHFFFAOYSA-N 0.000 claims 1
• JFWRXCSPZSVKSP-UHFFFAOYSA-N 4-[3-[(4-ethoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)OC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C1 JFWRXCSPZSVKSP-UHFFFAOYSA-N 0.000 claims 1
• SOMFOVYQEAFMSG-UHFFFAOYSA-N 4-[3-[(4-ethoxypyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)OC1=CC(=NC=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C SOMFOVYQEAFMSG-UHFFFAOYSA-N 0.000 claims 1
• MXOOMWDCRYQSFQ-UHFFFAOYSA-N 4-[3-[(4-fluorophenoxy)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(COC3=CC=C(F)C=C3)N2C=C1 MXOOMWDCRYQSFQ-UHFFFAOYSA-N 0.000 claims 1
• OQYWUQXXKNVHGJ-UHFFFAOYSA-N 4-[3-[(4-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C=C1 OQYWUQXXKNVHGJ-UHFFFAOYSA-N 0.000 claims 1
• BBCFYIVLAYLAPP-UHFFFAOYSA-N 4-[3-[(4-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound FC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=CC=NN2C)C=C1 BBCFYIVLAYLAPP-UHFFFAOYSA-N 0.000 claims 1
• HUSPHZJNSMOLKB-UHFFFAOYSA-N 4-[3-[(4-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C1 HUSPHZJNSMOLKB-UHFFFAOYSA-N 0.000 claims 1
• QVCFJSFRNGHPRB-UHFFFAOYSA-N 4-[3-[(4-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-propan-2-ylpyrimidin-2-amine Chemical compound FC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC(C)C)C=C1 QVCFJSFRNGHPRB-UHFFFAOYSA-N 0.000 claims 1
• FKZHAZLKNSFWAY-UHFFFAOYSA-N 4-[3-[(4-fluorophenyl)sulfanylmethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)SCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C FKZHAZLKNSFWAY-UHFFFAOYSA-N 0.000 claims 1
• RLUOUBADZLFELE-UHFFFAOYSA-N 4-[3-[(4-methoxyphenyl)-morpholin-4-ylmethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=CC=C(C=C1)C(C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)N1CCOCC1 RLUOUBADZLFELE-UHFFFAOYSA-N 0.000 claims 1
• ZQRXQPOFVIJYMN-UHFFFAOYSA-N 4-[3-[(4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound COC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C=C1 ZQRXQPOFVIJYMN-UHFFFAOYSA-N 0.000 claims 1
• ZOAIXMMGAWFUJB-UHFFFAOYSA-N 4-[3-[(4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C1 ZOAIXMMGAWFUJB-UHFFFAOYSA-N 0.000 claims 1
• YNEWUXUIBWZCRF-UHFFFAOYSA-N 4-[3-[(4-methoxypyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=CC(=NC=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YNEWUXUIBWZCRF-UHFFFAOYSA-N 0.000 claims 1
• RDVIKDAZCAOJEQ-UHFFFAOYSA-N 4-[3-[(4-methylcyclohexyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1CCC(CC1)C RDVIKDAZCAOJEQ-UHFFFAOYSA-N 0.000 claims 1
• OLUVRQIWFZGZIK-UHFFFAOYSA-N 4-[3-[(5,5-dimethyloxolan-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CC1(CCC(O1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C OLUVRQIWFZGZIK-UHFFFAOYSA-N 0.000 claims 1
• JIMOYKBXGOGXRG-UHFFFAOYSA-N 4-[3-[(5-chloropyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=CC(=NC=1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C JIMOYKBXGOGXRG-UHFFFAOYSA-N 0.000 claims 1
• GBAVVHXQBWGLNR-UHFFFAOYSA-N 4-[3-[(5-chloropyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound ClC=1C=C(C=NC=1)CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C GBAVVHXQBWGLNR-UHFFFAOYSA-N 0.000 claims 1
• GDFGOIBDYTUPFY-UHFFFAOYSA-N 4-[3-[(5-chloropyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(C=NC=1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C GDFGOIBDYTUPFY-UHFFFAOYSA-N 0.000 claims 1
• HNQDVWPXYFLOCI-UHFFFAOYSA-N 4-[3-[(5-chlorothiophen-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(S1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C HNQDVWPXYFLOCI-UHFFFAOYSA-N 0.000 claims 1
• SFLVLPOYIGXZSV-UHFFFAOYSA-N 4-[3-[(5-cyclopropyl-2-methoxypyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C=1C=C(C(=NC=1)OC)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C SFLVLPOYIGXZSV-UHFFFAOYSA-N 0.000 claims 1
• KSIUYABQVKJCCX-UHFFFAOYSA-N 4-[3-[(5-cyclopropylpyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C=1C=C(C=NC=1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C KSIUYABQVKJCCX-UHFFFAOYSA-N 0.000 claims 1
• YZYVYDTZLPVANK-UHFFFAOYSA-N 4-[3-[(5-cyclopropylthiophen-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C1=CC=C(S1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YZYVYDTZLPVANK-UHFFFAOYSA-N 0.000 claims 1
• CCVUEVYBVVJPRJ-UHFFFAOYSA-N 4-[3-[(5-fluoro-1H-indol-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C2C(=CNC2=CC=1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C CCVUEVYBVVJPRJ-UHFFFAOYSA-N 0.000 claims 1
• PGVQSTOYKPXPDP-UHFFFAOYSA-N 4-[3-[(5-fluoropyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=NC=1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C PGVQSTOYKPXPDP-UHFFFAOYSA-N 0.000 claims 1
• OKPNOLLUORHUPN-UHFFFAOYSA-N 4-[3-[(5-methyl-4-propan-2-yl-1,3-thiazol-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)(C)C=1N=C(SC=1C)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C OKPNOLLUORHUPN-UHFFFAOYSA-N 0.000 claims 1
• XNBGFLQZWOOJOW-UHFFFAOYSA-N 4-[3-[(6,6-dimethyloxan-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CC1(CCCC(O1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C XNBGFLQZWOOJOW-UHFFFAOYSA-N 0.000 claims 1
• YOFSVKVDKLUSBN-UHFFFAOYSA-N 4-[3-[(6-chloro-4-methoxypyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC(=CC(=N1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)OC YOFSVKVDKLUSBN-UHFFFAOYSA-N 0.000 claims 1
• DBQKFRYSGAFLPS-UHFFFAOYSA-N 4-[3-[(6-chloropyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound ClC1=CC=CC(=N1)CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C DBQKFRYSGAFLPS-UHFFFAOYSA-N 0.000 claims 1
• PADNWBBKCJQNBW-UHFFFAOYSA-N 4-[3-[(6-chloropyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=CC(CC2=NN=C3C=C(C=CN23)C2=CC=NC(NC3CCOCC3)=N2)=N1 PADNWBBKCJQNBW-UHFFFAOYSA-N 0.000 claims 1
• YBKLLTMWASJMME-UHFFFAOYSA-N 4-[3-[(6-chloropyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=N1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 YBKLLTMWASJMME-UHFFFAOYSA-N 0.000 claims 1
• PTZVMEPFTNBRKR-UHFFFAOYSA-N 4-[3-[(6-cyclopropylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C1=CC=CC(=N1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C PTZVMEPFTNBRKR-UHFFFAOYSA-N 0.000 claims 1
• YVGRMPLBQCREQN-UHFFFAOYSA-N 4-[3-[(6-ethoxypyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C)OC1=CC=C(C=N1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YVGRMPLBQCREQN-UHFFFAOYSA-N 0.000 claims 1
• VGMPETLVIDISST-UHFFFAOYSA-N 4-[3-[(6-fluoro-1H-indol-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C2C(=CNC2=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C VGMPETLVIDISST-UHFFFAOYSA-N 0.000 claims 1
• NGYIGNVVHLHARE-UHFFFAOYSA-N 4-[3-[(6-methoxypyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound COC1=CC=CC(=N1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C NGYIGNVVHLHARE-UHFFFAOYSA-N 0.000 claims 1
• ZWBTYXRJBXCOER-UHFFFAOYSA-N 4-[3-[(6-methoxypyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound COC1=CC=CC(=N1)CC1=NN=C2N1C=CC(=C2)C1=CC(=NC=C1)NC1=CC=NN1C ZWBTYXRJBXCOER-UHFFFAOYSA-N 0.000 claims 1
• QQCIGPFHZXRJRR-UHFFFAOYSA-N 4-[3-[(6-methoxypyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=CC=CC(=N1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C QQCIGPFHZXRJRR-UHFFFAOYSA-N 0.000 claims 1
• JCROQVWNBXVPLM-UHFFFAOYSA-N 4-[3-[(6-methoxypyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound COC1=CC=C(C=N1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 JCROQVWNBXVPLM-UHFFFAOYSA-N 0.000 claims 1
• BIMOZOFCKZHBSQ-SNAWJCMRSA-N 4-[3-[(E)-but-1-enyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(=C\CC)/C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C BIMOZOFCKZHBSQ-SNAWJCMRSA-N 0.000 claims 1
• KDCOKEQXGUDCNT-JWGURIENSA-N 4-[3-[(Z)-3-methyl-1-phenylbut-1-enyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound CC(\C=C(\C1=CC=CC=C1)/C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)C KDCOKEQXGUDCNT-JWGURIENSA-N 0.000 claims 1
• RGZQELZYRKPIOA-UHFFFAOYSA-N 4-[3-[(dimethylamino)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN(C)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C RGZQELZYRKPIOA-UHFFFAOYSA-N 0.000 claims 1
• RNMRUTDURWGZGW-UHFFFAOYSA-N 4-[3-[1-(3-fluorophenyl)-5-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)N1N=C(C=C1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C RNMRUTDURWGZGW-UHFFFAOYSA-N 0.000 claims 1
• RWCIUOVSWHSUEO-UHFFFAOYSA-N 4-[3-[1-(3-fluorophenyl)-5-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)N1N=C(C=C1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C RWCIUOVSWHSUEO-UHFFFAOYSA-N 0.000 claims 1
• ZUIFCUTXPPTPJN-UHFFFAOYSA-N 4-[3-[1-(4-chlorophenyl)-2-methylpropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C(C(C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C ZUIFCUTXPPTPJN-UHFFFAOYSA-N 0.000 claims 1
• RFTCPRPKNDSFGN-UHFFFAOYSA-N 4-[3-[1-(4-chlorophenyl)-2-methylpropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C(C(C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 RFTCPRPKNDSFGN-UHFFFAOYSA-N 0.000 claims 1
• MMSQAKKTALSCOH-UHFFFAOYSA-N 4-[3-[1-(4-chlorophenyl)-2-methylpropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-propan-2-ylpyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C(C(C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC(C)C MMSQAKKTALSCOH-UHFFFAOYSA-N 0.000 claims 1
• AKMKTJQKVNNHHK-UHFFFAOYSA-N 4-[3-[1-(4-chlorophenyl)cyclobutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C1(CCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 AKMKTJQKVNNHHK-UHFFFAOYSA-N 0.000 claims 1
• DTZVZVAFLGHPBY-UHFFFAOYSA-N 4-[3-[1-(4-chlorophenyl)cyclopentyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C1(CCCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 DTZVZVAFLGHPBY-UHFFFAOYSA-N 0.000 claims 1
• OUZNZCNJQFEKFH-UHFFFAOYSA-N 4-[3-[1-(4-chlorophenyl)cyclopropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C1(CC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 OUZNZCNJQFEKFH-UHFFFAOYSA-N 0.000 claims 1
• ILAHMPNTQPAUMW-UHFFFAOYSA-N 4-[3-[1-(4-chlorophenyl)ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C(C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C ILAHMPNTQPAUMW-UHFFFAOYSA-N 0.000 claims 1
• PGKHHVHICKXFGN-UHFFFAOYSA-N 4-[3-[1-(4-chlorophenyl)ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C(C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 PGKHHVHICKXFGN-UHFFFAOYSA-N 0.000 claims 1
• VXFVOIZEFBMBCX-UHFFFAOYSA-N 4-[3-[1-(4-fluorophenyl)-5-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)N1N=C(C=C1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C VXFVOIZEFBMBCX-UHFFFAOYSA-N 0.000 claims 1
• XZPBKGLOVIQQMD-UHFFFAOYSA-N 4-[3-[1-(4-fluorophenyl)-5-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)N1N=C(C=C1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C XZPBKGLOVIQQMD-UHFFFAOYSA-N 0.000 claims 1
• VRUZLGDFWPPWFS-UHFFFAOYSA-N 4-[3-[1-(4-fluorophenyl)pyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)N1N=C(C=C1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C VRUZLGDFWPPWFS-UHFFFAOYSA-N 0.000 claims 1
• YSRMDECAOPVLMW-UHFFFAOYSA-N 4-[3-[1-[(5-chloro-2-fluorophenyl)methyl]piperidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC=1C=CC(=C(CN2CC(CCC2)C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C=1)F YSRMDECAOPVLMW-UHFFFAOYSA-N 0.000 claims 1
• YGGHWFFCNNGXKD-UHFFFAOYSA-N 4-[3-[1-[(5-fluoro-2-methoxypyridin-3-yl)methyl]piperidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C(=NC=1)OC)CN1CC(CCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 YGGHWFFCNNGXKD-UHFFFAOYSA-N 0.000 claims 1
• BMQSCVAJLLIROL-UHFFFAOYSA-N 4-[3-[1-methyl-3-(2-methylpropyl)pyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C(C(C)C)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)C BMQSCVAJLLIROL-UHFFFAOYSA-N 0.000 claims 1
• BGFIGLQSLNAWNI-UHFFFAOYSA-N 4-[3-[1-methyl-3-(2-methylpropyl)pyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C(C)C)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C BGFIGLQSLNAWNI-UHFFFAOYSA-N 0.000 claims 1
• ZRLSUFSUJKZQEA-UHFFFAOYSA-N 4-[3-[1-methyl-5-(2-methylpropyl)pyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C(C(C)C)C1=C(C=NN1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C ZRLSUFSUJKZQEA-UHFFFAOYSA-N 0.000 claims 1
• FNAKDCNEZXMSCS-UHFFFAOYSA-N 4-[3-[1-methyl-5-(2-methylpropyl)pyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C(C)C)C1=C(C=NN1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C FNAKDCNEZXMSCS-UHFFFAOYSA-N 0.000 claims 1
• XQFSDCWTMXGUNJ-UHFFFAOYSA-N 4-[3-[2-(2-fluoroethoxy)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FCCOC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C XQFSDCWTMXGUNJ-UHFFFAOYSA-N 0.000 claims 1
• FTFXKICINZNVTE-UHFFFAOYSA-N 4-[3-[2-(3-chlorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(C=CC=1)N1N=C(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C(F)(F)F FTFXKICINZNVTE-UHFFFAOYSA-N 0.000 claims 1
• QRTVOHDPJWCWJW-UHFFFAOYSA-N 4-[3-[2-(3-chlorophenyl)ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-propan-2-ylpyrimidin-2-amine Chemical compound ClC=1C=C(CCC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC(C)C)C=CC=1 QRTVOHDPJWCWJW-UHFFFAOYSA-N 0.000 claims 1
• MYDBUBCONJHWND-UHFFFAOYSA-N 4-[3-[2-(3-chlorophenyl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(CCC2=NN=C3N2N=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=1 MYDBUBCONJHWND-UHFFFAOYSA-N 0.000 claims 1
• PXMOUKQFKXWVTD-UHFFFAOYSA-N 4-[3-[2-(3-cyclopropylpyrazol-1-yl)ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)C1=NN(C=C1)CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C PXMOUKQFKXWVTD-UHFFFAOYSA-N 0.000 claims 1
• ZSFXBCHIEFESRF-UHFFFAOYSA-N 4-[3-[2-(3-fluoro-4-methoxyphenyl)ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-propan-2-ylpyrimidin-2-amine Chemical compound FC=1C=C(CCC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC(C)C)C=CC=1OC ZSFXBCHIEFESRF-UHFFFAOYSA-N 0.000 claims 1
• GBSRDWCZKIALRV-UHFFFAOYSA-N 4-[3-[2-(3-fluorophenyl)-5-(trifluoromethyl)pyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)N1N=C(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C(F)(F)F GBSRDWCZKIALRV-UHFFFAOYSA-N 0.000 claims 1
• SFFOVVIJMOAAFM-UHFFFAOYSA-N 4-[3-[2-(3-fluorophenyl)-5-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)N1N=C(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)C SFFOVVIJMOAAFM-UHFFFAOYSA-N 0.000 claims 1
• RNKAOULJQIKJBE-UHFFFAOYSA-N 4-[3-[2-(3-fluorophenyl)-5-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)N1N=C(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C RNKAOULJQIKJBE-UHFFFAOYSA-N 0.000 claims 1
• MEDHVASXHQBGJA-UHFFFAOYSA-N 4-[3-[2-(3-fluorophenyl)pyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)N1N=CC=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C MEDHVASXHQBGJA-UHFFFAOYSA-N 0.000 claims 1
• SSNNMYUIIAJKNU-UHFFFAOYSA-N 4-[3-[2-(4-chlorophenyl)-2-methoxyethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)OC SSNNMYUIIAJKNU-UHFFFAOYSA-N 0.000 claims 1
• VPNOFAFWPYVDRN-UHFFFAOYSA-N 4-[3-[2-(4-chlorophenyl)propan-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C(C)(C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 VPNOFAFWPYVDRN-UHFFFAOYSA-N 0.000 claims 1
• ZHWZXQVEZWBTSA-UHFFFAOYSA-N 4-[3-[2-(4-fluorophenoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(OC2=C(C=CC=C2)C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C=C1 ZHWZXQVEZWBTSA-UHFFFAOYSA-N 0.000 claims 1
• CRDREEMSYWKQIG-UHFFFAOYSA-N 4-[3-[2-(4-fluorophenyl)-2-methylpropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)C CRDREEMSYWKQIG-UHFFFAOYSA-N 0.000 claims 1
• OGLSVEFIGJXEHN-UHFFFAOYSA-N 4-[3-[2-(4-fluorophenyl)-5-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)N1N=C(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)C OGLSVEFIGJXEHN-UHFFFAOYSA-N 0.000 claims 1
• UCUHYHNNKSFVGV-UHFFFAOYSA-N 4-[3-[2-(4-fluorophenyl)-5-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)N1N=C(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C UCUHYHNNKSFVGV-UHFFFAOYSA-N 0.000 claims 1
• GUWLBPBOFNPZMH-UHFFFAOYSA-N 4-[3-[2-(4-fluorophenyl)pyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)N1N=CC=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C GUWLBPBOFNPZMH-UHFFFAOYSA-N 0.000 claims 1
• IJMDMLXEYJDOBP-UHFFFAOYSA-N 4-[3-[2-(4-fluorophenyl)pyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)N1N=CC=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C IJMDMLXEYJDOBP-UHFFFAOYSA-N 0.000 claims 1
• YWCOLPSGTQCDIG-UHFFFAOYSA-N 4-[3-[2-(4-methoxyphenoxy)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound COC1=CC=C(OC2=C(C=CC=C2)C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C=C1 YWCOLPSGTQCDIG-UHFFFAOYSA-N 0.000 claims 1
• LFMVNZBHUANXBJ-UHFFFAOYSA-N 4-[3-[2-(4-methoxyphenyl)-2-methylpropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC1=CC=C(C=C1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)(C)C LFMVNZBHUANXBJ-UHFFFAOYSA-N 0.000 claims 1
• SOFVLLRQVDZNPL-UHFFFAOYSA-N 4-[3-[2-(5-chlorothiophen-2-yl)-2-methoxyethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(S1)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)OC SOFVLLRQVDZNPL-UHFFFAOYSA-N 0.000 claims 1
• NMQIQWRLVCHJKW-UHFFFAOYSA-N 4-[3-[2-(5-methyl-2-phenyl-1,2,4-triazol-3-yl)ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CC1=NN(C(=N1)CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C1=CC=CC=C1 NMQIQWRLVCHJKW-UHFFFAOYSA-N 0.000 claims 1
• YGZAYMKQXGCUEW-UHFFFAOYSA-N 4-[3-[2-(benzenesulfonyl)ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CCS(=O)(=O)C1=CC=CC=C1 YGZAYMKQXGCUEW-UHFFFAOYSA-N 0.000 claims 1
• AFLDFTJESKKONU-UHFFFAOYSA-N 4-[3-[2-(cyclopropylmethoxy)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)COC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C AFLDFTJESKKONU-UHFFFAOYSA-N 0.000 claims 1
• BUALUYYMEUGEKR-UHFFFAOYSA-N 4-[3-[2-[1-(4-methylphenyl)tetrazol-5-yl]ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CCC1=NN=NN1C1=CC=C(C=C1)C BUALUYYMEUGEKR-UHFFFAOYSA-N 0.000 claims 1
• VHZVQJSZMUKTQF-UHFFFAOYSA-N 4-[3-[2-[4-(4-methylphenyl)triazol-1-yl]ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CCN1N=NC(=C1)C1=CC=C(C=C1)C VHZVQJSZMUKTQF-UHFFFAOYSA-N 0.000 claims 1
• YJWUBPKWJXXWSL-UHFFFAOYSA-N 4-[3-[2-[5-(4-methylphenyl)triazol-1-yl]ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CCN1N=NC=C1C1=CC=C(C=C1)C YJWUBPKWJXXWSL-UHFFFAOYSA-N 0.000 claims 1
• ORZGOAKESJWEFL-UHFFFAOYSA-N 4-[3-[2-amino-2-(3-chloro-4-fluorophenyl)ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound NC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C1=CC(=C(C=C1)F)Cl ORZGOAKESJWEFL-UHFFFAOYSA-N 0.000 claims 1
• CLUTUUVGDGVCHG-UHFFFAOYSA-N 4-[3-[2-methoxy-2-(4-methoxyphenyl)ethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C1=CC=C(C=C1)OC CLUTUUVGDGVCHG-UHFFFAOYSA-N 0.000 claims 1
• QRLPKYQOLMLFQM-UHFFFAOYSA-N 4-[3-[3-(3,4-difluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1F)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)C QRLPKYQOLMLFQM-UHFFFAOYSA-N 0.000 claims 1
• ZUVVCTYGCZHFSH-UHFFFAOYSA-N 4-[3-[3-(3,4-difluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1F)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C ZUVVCTYGCZHFSH-UHFFFAOYSA-N 0.000 claims 1
• VRSGDEDIYQNIMV-UHFFFAOYSA-N 4-[3-[3-(3-fluorophenyl)-1,5-dimethylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)C1=NN(C(=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C)C VRSGDEDIYQNIMV-UHFFFAOYSA-N 0.000 claims 1
• VKDPXSVTRXKBCV-UHFFFAOYSA-N 4-[3-[3-(3-fluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)C VKDPXSVTRXKBCV-UHFFFAOYSA-N 0.000 claims 1
• OYADILOLAICTEY-UHFFFAOYSA-N 4-[3-[3-(3-fluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C OYADILOLAICTEY-UHFFFAOYSA-N 0.000 claims 1
• KDVURKJNIRCOHA-UHFFFAOYSA-N 4-[3-[3-(4-chlorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)C KDVURKJNIRCOHA-UHFFFAOYSA-N 0.000 claims 1
• GEUJUTWFBAMITO-UHFFFAOYSA-N 4-[3-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C)C GEUJUTWFBAMITO-UHFFFAOYSA-N 0.000 claims 1
• NMNWUKPZLVDWJQ-UHFFFAOYSA-N 4-[3-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)C1=NN(C=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C NMNWUKPZLVDWJQ-UHFFFAOYSA-N 0.000 claims 1
• OAIXZCLSNGXSEM-UHFFFAOYSA-N 4-[3-[3-[(3-fluorophenyl)methyl]-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN(C=C2C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C)C=CC=1 OAIXZCLSNGXSEM-UHFFFAOYSA-N 0.000 claims 1
• FNJACKMJAIILIC-UHFFFAOYSA-N 4-[3-[3-[(4-fluorophenyl)methyl]-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(CC2=NN(C=C2C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C)C=C1 FNJACKMJAIILIC-UHFFFAOYSA-N 0.000 claims 1
• IHZTZEWWCFAKSI-UHFFFAOYSA-N 4-[3-[3-[(4-fluorophenyl)methyl]-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(CC2=NN(C=C2C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C)C=C1 IHZTZEWWCFAKSI-UHFFFAOYSA-N 0.000 claims 1
• GEFRJGUMRZCHTR-UHFFFAOYSA-N 4-[3-[3-fluoro-2-(fluoromethyl)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FCC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)CF GEFRJGUMRZCHTR-UHFFFAOYSA-N 0.000 claims 1
• VCUJEEQJZXKLKB-UHFFFAOYSA-N 4-[3-[4-(3-chlorophenyl)-1-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(C=CC=1)C=1C(=NN(C=1)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C VCUJEEQJZXKLKB-UHFFFAOYSA-N 0.000 claims 1
• BWVDHWYNHRISLO-UHFFFAOYSA-N 4-[3-[4-(3-chlorophenyl)-2,5-dimethylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(C=CC=1)C=1C(=NN(C=1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C)C BWVDHWYNHRISLO-UHFFFAOYSA-N 0.000 claims 1
• RJSOOKFPTMISDK-UHFFFAOYSA-N 4-[3-[4-(3-chlorophenyl)-2-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(C=CC=1)C=1C=NN(C=1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C RJSOOKFPTMISDK-UHFFFAOYSA-N 0.000 claims 1
• NSCXMNQYJKFUIP-UHFFFAOYSA-N 4-[3-[4-(4-chlorophenyl)-1-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C=1C(=NN(C=1)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C NSCXMNQYJKFUIP-UHFFFAOYSA-N 0.000 claims 1
• BWKLAASTGKNIAU-UHFFFAOYSA-N 4-[3-[4-(4-chlorophenyl)-2,5-dimethylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C=1C(=NN(C=1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C)C BWKLAASTGKNIAU-UHFFFAOYSA-N 0.000 claims 1
• VDLMBEPZJBTORI-UHFFFAOYSA-N 4-[3-[4-(4-chlorophenyl)-2-methylpyrazol-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C=1C=NN(C=1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C VDLMBEPZJBTORI-UHFFFAOYSA-N 0.000 claims 1
• HTWVXGAFYACKDS-UHFFFAOYSA-N 4-[3-[4-(cyclopropylmethyl)morpholin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1(CC1)CN1CC(OCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C HTWVXGAFYACKDS-UHFFFAOYSA-N 0.000 claims 1
• JVKFYJQOZIVFAD-UHFFFAOYSA-N 4-[3-[5-(2,6-difluorophenoxy)-1-methylpiperidin-3-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(C3CC(CN(C)C3)OC3=C(F)C=CC=C3F)N2C=C1 JVKFYJQOZIVFAD-UHFFFAOYSA-N 0.000 claims 1
• OARHSYGQCNVSQG-UHFFFAOYSA-N 4-[3-[5-(3,4-difluorophenyl)-1,3-dimethylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1F)C1=C(C(=NN1C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C OARHSYGQCNVSQG-UHFFFAOYSA-N 0.000 claims 1
• WKMBQALOCNMYDQ-UHFFFAOYSA-N 4-[3-[5-(3,4-difluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1F)C1=C(C=NN1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C WKMBQALOCNMYDQ-UHFFFAOYSA-N 0.000 claims 1
• QTAJYFDFKIFQDG-UHFFFAOYSA-N 4-[3-[5-(3-chlorophenyl)-1,3-dimethylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC=1C=C(C=CC=1)C1=C(C(=NN1C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C QTAJYFDFKIFQDG-UHFFFAOYSA-N 0.000 claims 1
• GZUPGEPKLRHYPX-UHFFFAOYSA-N 4-[3-[5-(3-fluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)C1=C(C=NN1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C GZUPGEPKLRHYPX-UHFFFAOYSA-N 0.000 claims 1
• ZZYJCHLJFJKHBP-UHFFFAOYSA-N 4-[3-[5-(3-fluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(C=CC=1)C1=C(C=NN1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C ZZYJCHLJFJKHBP-UHFFFAOYSA-N 0.000 claims 1
• HNORWZDKQVYCEA-UHFFFAOYSA-N 4-[3-[5-(4-chloro-3-fluorophenyl)-1,3-dimethylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=C(C=C(C=C1)C1=C(C(=NN1C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)F HNORWZDKQVYCEA-UHFFFAOYSA-N 0.000 claims 1
• YNSLAKOUQBNAMO-UHFFFAOYSA-N 4-[3-[5-(4-chlorophenyl)-1,3-dimethylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C1=C(C(=NN1C)C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YNSLAKOUQBNAMO-UHFFFAOYSA-N 0.000 claims 1
• NQFZENWLYYFQGG-UHFFFAOYSA-N 4-[3-[5-(4-chlorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound ClC1=CC=C(C=C1)C1=C(C=NN1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC=1C=NN(C=1)C NQFZENWLYYFQGG-UHFFFAOYSA-N 0.000 claims 1
• HJGIRSJHZNCHOB-UHFFFAOYSA-N 4-[3-[5-(4-fluorophenyl)-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(C=C1)C1=C(C=NN1C)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C HJGIRSJHZNCHOB-UHFFFAOYSA-N 0.000 claims 1
• AJNZGRUTCASXRV-UHFFFAOYSA-N 4-[3-[5-[(3-fluorophenyl)methyl]-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=C(C=NN2C)C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C=CC=1 AJNZGRUTCASXRV-UHFFFAOYSA-N 0.000 claims 1
• UKZAOWLILLQSGO-UHFFFAOYSA-N 4-[3-[5-[(3-fluorophenyl)methyl]-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=C(C=NN2C)C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=1 UKZAOWLILLQSGO-UHFFFAOYSA-N 0.000 claims 1
• GREZEBSTEHTUKF-UHFFFAOYSA-N 4-[3-[5-[(4-fluorophenyl)methyl]-1-methylpyrazol-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound FC1=CC=C(CC2=C(C=NN2C)C2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC=2C=NN(C=2)C)C=C1 GREZEBSTEHTUKF-UHFFFAOYSA-N 0.000 claims 1
• MTMMWPCOIRCZKC-UHFFFAOYSA-N 4-[3-[[1-(2-fluoroethoxy)cyclopropyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FCCOC1(CC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C MTMMWPCOIRCZKC-UHFFFAOYSA-N 0.000 claims 1
• BMUDCHNJJAICSC-UHFFFAOYSA-N 4-[3-[[1-(2-methylpropoxy)cyclopropyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C(C(C)C)OC1(CC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C BMUDCHNJJAICSC-UHFFFAOYSA-N 0.000 claims 1
• JRZCZYCBYSJZOG-UHFFFAOYSA-N 4-[3-[[2-fluoro-4-(trifluoromethyl)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=CC=NN2C)C=CC(=C1)C(F)(F)F JRZCZYCBYSJZOG-UHFFFAOYSA-N 0.000 claims 1
• OWOJTHYODXXCQX-UHFFFAOYSA-N 4-[3-[[2-fluoro-4-(trifluoromethyl)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC(=C1)C(F)(F)F OWOJTHYODXXCQX-UHFFFAOYSA-N 0.000 claims 1
• ZHYRLNXTLXQFHW-UHFFFAOYSA-N 4-[3-[[3-(2-fluoro-4-methylphenyl)triazol-4-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=C(C=CC(=C1)C)N1N=NC=C1CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C ZHYRLNXTLXQFHW-UHFFFAOYSA-N 0.000 claims 1
• VVENUPHXJNCIFY-UHFFFAOYSA-N 4-[3-[[3-(difluoromethoxy)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC(OC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=CC=1)F VVENUPHXJNCIFY-UHFFFAOYSA-N 0.000 claims 1
• FSVWPOSUGCFHQI-UHFFFAOYSA-N 4-[3-[[3-fluoro-4-(trifluoromethoxy)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2CCOCC2)C=CC=1OC(F)(F)F FSVWPOSUGCFHQI-UHFFFAOYSA-N 0.000 claims 1
• AJOKSVOKEWATJL-UHFFFAOYSA-N 4-[3-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC=1C=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C(C=1)C(F)(F)F AJOKSVOKEWATJL-UHFFFAOYSA-N 0.000 claims 1
• BZOISNKQYXCSER-UHFFFAOYSA-N 4-[3-[[4-(difluoromethoxy)-2-fluorophenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound FC(OC1=CC(=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=CC=NN2C)C=C1)F)F BZOISNKQYXCSER-UHFFFAOYSA-N 0.000 claims 1
• NXQJGFGJLOIMQK-UHFFFAOYSA-N 4-[3-[[4-(difluoromethoxy)-2-fluorophenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC(OC1=CC(=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C1)F)F NXQJGFGJLOIMQK-UHFFFAOYSA-N 0.000 claims 1
• QEJBMKHWNQZRSB-UHFFFAOYSA-N 4-[3-[[4-(difluoromethoxy)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound FC(OC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=CC(=NC=C2)NC2=CC=NN2C)C=C1)F QEJBMKHWNQZRSB-UHFFFAOYSA-N 0.000 claims 1
• CAHRYWGOEOULFZ-UHFFFAOYSA-N 4-[3-[[4-(difluoromethoxy)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC(OC1=CC=C(CC2=NN=C3N2C=CC(=C3)C2=NC(=NC=C2)NC2=CC=NN2C)C=C1)F CAHRYWGOEOULFZ-UHFFFAOYSA-N 0.000 claims 1
• BVJOFBQMIIUIMJ-UHFFFAOYSA-N 4-[3-[difluoro-(3-fluoro-4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound FC(C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1)(C1=CC(=C(C=C1)OC)F)F BVJOFBQMIIUIMJ-UHFFFAOYSA-N 0.000 claims 1
• BXRXTKQHAKJPPN-UHFFFAOYSA-N 4-[3-[dimethylamino-(4-fluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN(C)C(C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C1=CC=C(C=C1)F BXRXTKQHAKJPPN-UHFFFAOYSA-N 0.000 claims 1
• AJDLYRJMRIPBMP-UHFFFAOYSA-N 4-fluoro-3-[[3-[7-[2-(oxan-4-ylamino)pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]piperidin-1-yl]methyl]benzonitrile Chemical compound FC1=C(C=C(C#N)C=C1)CN1CC(CCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 AJDLYRJMRIPBMP-UHFFFAOYSA-N 0.000 claims 1
• HAECXPHZFJUTLK-UHFFFAOYSA-N 5,5,5-trifluoro-1-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]pentan-2-ol Chemical compound FC(CCC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)O)(F)F HAECXPHZFJUTLK-UHFFFAOYSA-N 0.000 claims 1
• OZERFYUJXCBFHD-UHFFFAOYSA-N 5-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]-1H-pyridin-2-one Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC=1C=CC(=NC=1)O OZERFYUJXCBFHD-UHFFFAOYSA-N 0.000 claims 1
• DQVNOAMZWYHRAT-UHFFFAOYSA-N 5-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]thiophene-2-carbonitrile Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=CC=C(S1)C#N DQVNOAMZWYHRAT-UHFFFAOYSA-N 0.000 claims 1
• OITMQGWTMKHBGW-UHFFFAOYSA-N 5-cyclopropyl-3-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]-1H-pyridin-2-one Chemical compound C1(CC1)C=1C=C(C(=NC=1)O)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C OITMQGWTMKHBGW-UHFFFAOYSA-N 0.000 claims 1
• KWJJNXOWCYWWGF-UHFFFAOYSA-N 5-fluoro-4-[3-[(4-methoxyphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(oxan-4-yl)pyrimidin-2-amine Chemical compound COC1=CC=C(CC2=NN=C3C=C(C=CN23)C2=C(F)C=NC(NC3CCOCC3)=N2)C=C1 KWJJNXOWCYWWGF-UHFFFAOYSA-N 0.000 claims 1
• YHIPIOKUORSWFP-UHFFFAOYSA-N 6-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]-1H-pyridin-2-one Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=CC=CC(=N1)O YHIPIOKUORSWFP-UHFFFAOYSA-N 0.000 claims 1
• UDBAVAXCXIFEMV-UHFFFAOYSA-N 6-[[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]methyl]pyridine-2-carbonitrile Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=CC=CC(=N1)C#N UDBAVAXCXIFEMV-UHFFFAOYSA-N 0.000 claims 1
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
• ZHZWSEGEGGEJDV-UHFFFAOYSA-N N-(1-methylpyrazol-4-yl)-4-[3-(1-methyl-3-pyridin-3-ylpyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC(=C1)NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C=1C(=NN(C=1)C)C=1C=NC=CC=1 ZHZWSEGEGGEJDV-UHFFFAOYSA-N 0.000 claims 1
• QALJTEPVNWMCHJ-UHFFFAOYSA-N N-(1-methylpyrazol-4-yl)-4-[3-[(6-methylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC(=C1)NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC(=CC=C1)C QALJTEPVNWMCHJ-UHFFFAOYSA-N 0.000 claims 1
• XKQSNROHUKQZIQ-UHFFFAOYSA-N N-(1-methylpyrazol-4-yl)-4-[3-[[6-(trifluoromethyl)pyridin-2-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC(=C1)NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC(=CC=C1)C(F)(F)F XKQSNROHUKQZIQ-UHFFFAOYSA-N 0.000 claims 1
• ZWUBSKWYJZMYIW-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-(3-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C ZWUBSKWYJZMYIW-UHFFFAOYSA-N 0.000 claims 1
• KCHSJLMPAITLKC-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-(3-propyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CCC KCHSJLMPAITLKC-UHFFFAOYSA-N 0.000 claims 1
• BIMLFMRHEGUFAG-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-([1,2,4]triazolo[4,3-a]pyridin-7-yl)pyrimidin-2-amine Chemical compound N=1N=CN2C=1C=C(C=C2)C1=NC(=NC=C1)NC1=CC=NN1C BIMLFMRHEGUFAG-UHFFFAOYSA-N 0.000 claims 1
• PTOBNSAWQQPVJC-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(1,3-thiazol-2-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC=1SC=CN=1 PTOBNSAWQQPVJC-UHFFFAOYSA-N 0.000 claims 1
• PKFYXRTWLVBXQU-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(1-phenylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C(C)C1=CC=CC=C1 PKFYXRTWLVBXQU-UHFFFAOYSA-N 0.000 claims 1
• SMQRDOTVWZRHCA-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(2,2,3,3-tetramethylcyclopropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C1C(C1(C)C)(C)C SMQRDOTVWZRHCA-UHFFFAOYSA-N 0.000 claims 1
• GRROMAIVBYOMLS-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(2-methylsulfanylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(CC)SC GRROMAIVBYOMLS-UHFFFAOYSA-N 0.000 claims 1
• VLKUPJWUIZGDPE-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(2-methylsulfanylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CCSC VLKUPJWUIZGDPE-UHFFFAOYSA-N 0.000 claims 1
• STCIPISBGIBFRA-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(2-methylsulfanylpropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(C)SC STCIPISBGIBFRA-UHFFFAOYSA-N 0.000 claims 1
• YZROOINDHWSQTL-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(2-phenylsulfanylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CCSC3=CC=CC=C3)N2C=C1 YZROOINDHWSQTL-UHFFFAOYSA-N 0.000 claims 1
• OBEIYIHDRUNVMX-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(3,3,3-trifluoro-2-methoxypropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC(C(F)(F)F)OC OBEIYIHDRUNVMX-UHFFFAOYSA-N 0.000 claims 1
• DFKGZSLVVAQEDV-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(3,3,3-trifluoro-2-methoxypropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(C(F)(F)F)OC DFKGZSLVVAQEDV-UHFFFAOYSA-N 0.000 claims 1
• FGDQPUOVOYUOPL-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(3,3,3-trifluoro-2-methylpropyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(C(F)(F)F)C FGDQPUOVOYUOPL-UHFFFAOYSA-N 0.000 claims 1
• KFRLEBDOWMSTEO-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(4,4,4-trifluoro-2-methylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CC(CC1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1)CC(F)(F)F KFRLEBDOWMSTEO-UHFFFAOYSA-N 0.000 claims 1
• IMYLFCBOTYPMOT-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(5,5,5-trifluoro-2-methoxypentyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(CCC(F)(F)F)OC IMYLFCBOTYPMOT-UHFFFAOYSA-N 0.000 claims 1
• UPHYIJKETIFZAC-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(oxan-2-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC1OCCCC1 UPHYIJKETIFZAC-UHFFFAOYSA-N 0.000 claims 1
• JNWWILZRNKHGEG-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(oxan-2-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1OCCCC1 JNWWILZRNKHGEG-UHFFFAOYSA-N 0.000 claims 1
• PXAIWYKJDJZXNN-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(oxan-3-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1COCCC1 PXAIWYKJDJZXNN-UHFFFAOYSA-N 0.000 claims 1
• SWLLRCSWPCJLBN-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(oxan-4-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1CCOCC1 SWLLRCSWPCJLBN-UHFFFAOYSA-N 0.000 claims 1
• ZCGUBZVAHUIQFW-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(oxolan-3-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1COCC1 ZCGUBZVAHUIQFW-UHFFFAOYSA-N 0.000 claims 1
• KJZGJOBEUPWTKB-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(phenylsulfanylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CSC3=CC=CC=C3)N2C=C1 KJZGJOBEUPWTKB-UHFFFAOYSA-N 0.000 claims 1
• DXCUKVUIQRTJGD-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(piperidin-1-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CN1CCCCC1 DXCUKVUIQRTJGD-UHFFFAOYSA-N 0.000 claims 1
• GBCLVOUWXMAQTB-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(propan-2-ylsulfanylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound C(C)(C)SCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C GBCLVOUWXMAQTB-UHFFFAOYSA-N 0.000 claims 1
• XYPLTWUBVIVEAI-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(pyrazin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC=CN=C1 XYPLTWUBVIVEAI-UHFFFAOYSA-N 0.000 claims 1
• ZXFLIIBHWVJVPT-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(pyrimidin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC=CC=N1 ZXFLIIBHWVJVPT-UHFFFAOYSA-N 0.000 claims 1
• OCMGRVPKQFLJQV-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(pyrimidin-5-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC=1C=NC=NC=1 OCMGRVPKQFLJQV-UHFFFAOYSA-N 0.000 claims 1
• ABLFQGWZXGHLDK-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-(pyrrolidin-1-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CN1CCCC1 ABLFQGWZXGHLDK-UHFFFAOYSA-N 0.000 claims 1
• HYMSRNAUKGIWPB-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(1-methylpyrazol-4-yl)-phenylmethyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC(=C1)C(C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)C1=CC=CC=C1 HYMSRNAUKGIWPB-UHFFFAOYSA-N 0.000 claims 1
• REQWOXCJDIQCAN-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(1-methylpyrazol-4-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC(=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C REQWOXCJDIQCAN-UHFFFAOYSA-N 0.000 claims 1
• SFTXWOLJZBAROK-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(1-propan-2-ylcyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CC(C)C1(CC2=NN=C3C=C(C=CN23)C2=CC=NC(NC3=CC=NN3C)=N2)CC1 SFTXWOLJZBAROK-UHFFFAOYSA-N 0.000 claims 1
• YCIJBXIMJVQJQR-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(1-propan-2-yloxycyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound C(C)(C)OC1(CC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C YCIJBXIMJVQJQR-UHFFFAOYSA-N 0.000 claims 1
• FKEZLQZYUJCHJP-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2-methylpyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC=1C(=NC=CC=1)C FKEZLQZYUJCHJP-UHFFFAOYSA-N 0.000 claims 1
• VBLAHBRJLSOFAK-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2-methylpyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC=1C(=NC=CC=1)C VBLAHBRJLSOFAK-UHFFFAOYSA-N 0.000 claims 1
• LWIMSCFRWVBTMN-QGZVFWFLSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2R)-3,3,3-trifluoro-2-(4-fluorophenyl)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@@H](C(F)(F)F)C1=CC=C(C=C1)F LWIMSCFRWVBTMN-QGZVFWFLSA-N 0.000 claims 1
• UZMFKWOHHPPMBW-GOSISDBHSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2R)-3,3,3-trifluoro-2-(4-methoxyphenyl)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@@H](C(F)(F)F)C1=CC=C(C=C1)OC UZMFKWOHHPPMBW-GOSISDBHSA-N 0.000 claims 1
• DFKGZSLVVAQEDV-CYBMUJFWSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2R)-3,3,3-trifluoro-2-methoxypropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@H](C(F)(F)F)OC DFKGZSLVVAQEDV-CYBMUJFWSA-N 0.000 claims 1
• IMYLFCBOTYPMOT-CQSZACIVSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2R)-5,5,5-trifluoro-2-methoxypentyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@@H](CCC(F)(F)F)OC IMYLFCBOTYPMOT-CQSZACIVSA-N 0.000 claims 1
• LWIMSCFRWVBTMN-KRWDZBQOSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2S)-3,3,3-trifluoro-2-(4-fluorophenyl)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@H](C(F)(F)F)C1=CC=C(C=C1)F LWIMSCFRWVBTMN-KRWDZBQOSA-N 0.000 claims 1
• UZMFKWOHHPPMBW-SFHVURJKSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2S)-3,3,3-trifluoro-2-(4-methoxyphenyl)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@H](C(F)(F)F)C1=CC=C(C=C1)OC UZMFKWOHHPPMBW-SFHVURJKSA-N 0.000 claims 1
• DFKGZSLVVAQEDV-ZDUSSCGKSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2S)-3,3,3-trifluoro-2-methoxypropyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@@H](C(F)(F)F)OC DFKGZSLVVAQEDV-ZDUSSCGKSA-N 0.000 claims 1
• IMYLFCBOTYPMOT-AWEZNQCLSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(2S)-5,5,5-trifluoro-2-methoxypentyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C[C@H](CCC(F)(F)F)OC IMYLFCBOTYPMOT-AWEZNQCLSA-N 0.000 claims 1
• MCIZPNRPBFPGIT-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(4-methyl-1,3-thiazol-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC=1SC=C(N=1)C MCIZPNRPBFPGIT-UHFFFAOYSA-N 0.000 claims 1
• QDEKWGPEVPUQLG-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(4-methylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC=CC(=C1)C QDEKWGPEVPUQLG-UHFFFAOYSA-N 0.000 claims 1
• OBLDEWVCPLUKCV-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(4-methylsulfanylphenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CSC1=CC=C(CC2=NN=C3C=C(C=CN23)C2=CC=NC(NC3=CC=NN3C)=N2)C=C1 OBLDEWVCPLUKCV-UHFFFAOYSA-N 0.000 claims 1
• XFGAFEVSQPQVJS-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(4-propan-2-ylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound C(C)(C)C1=CC(=NC=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C XFGAFEVSQPQVJS-UHFFFAOYSA-N 0.000 claims 1
• MQYLZYSHDVXKCW-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(5-methyl-1,3-thiazol-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC=1SC(=CN=1)C MQYLZYSHDVXKCW-UHFFFAOYSA-N 0.000 claims 1
• VJWUSGTYKUIUQS-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(5-methylpyridin-3-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC=1C=NC=C(C=1)C VJWUSGTYKUIUQS-UHFFFAOYSA-N 0.000 claims 1
• VAJMRBDOWXZZPN-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(6-methylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC(=CC=C1)C VAJMRBDOWXZZPN-UHFFFAOYSA-N 0.000 claims 1
• ZFSKPXBJOLQPEZ-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(6-methylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC(=CC=C1)C ZFSKPXBJOLQPEZ-UHFFFAOYSA-N 0.000 claims 1
• AJZLDMPBAGDZJW-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(6-phenylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC(=CC=C1)C1=CC=CC=C1 AJZLDMPBAGDZJW-UHFFFAOYSA-N 0.000 claims 1
• VVXHBLGGVWHKJH-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[(6-propan-2-ylpyridin-2-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound C(C)(C)C1=CC=CC(=N1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C VVXHBLGGVWHKJH-UHFFFAOYSA-N 0.000 claims 1
• YFWNGNUKNMTJEM-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[2-(trifluoromethyl)butyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(CC)C(F)(F)F YFWNGNUKNMTJEM-UHFFFAOYSA-N 0.000 claims 1
• KJNNDELKOCORQG-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[2-(trifluoromethyl)cyclobutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C1C(CC1)C(F)(F)F KJNNDELKOCORQG-UHFFFAOYSA-N 0.000 claims 1
• LWIMSCFRWVBTMN-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[3,3,3-trifluoro-2-(4-fluorophenyl)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(C(F)(F)F)C1=CC=C(C=C1)F LWIMSCFRWVBTMN-UHFFFAOYSA-N 0.000 claims 1
• UZMFKWOHHPPMBW-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[3,3,3-trifluoro-2-(4-methoxyphenyl)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(C(F)(F)F)C1=CC=C(C=C1)OC UZMFKWOHHPPMBW-UHFFFAOYSA-N 0.000 claims 1
• OVCRRCPDRQFKCC-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[3,3,3-trifluoro-2-(4-methoxyphenyl)propyl]-[1,2,4]triazolo[4,3-b]pyridazin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(N=C1)C(=NN=2)CC(C(F)(F)F)C1=CC=C(C=C1)OC OVCRRCPDRQFKCC-UHFFFAOYSA-N 0.000 claims 1
• GIQRLLQJGPBVMO-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[3,3,3-trifluoro-2-(trifluoromethyl)propyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(C(F)(F)F)C(F)(F)F GIQRLLQJGPBVMO-UHFFFAOYSA-N 0.000 claims 1
• CYQQDSYDZHYCCN-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[1-(trifluoromethyl)cyclobutyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1(CCC1)C(F)(F)F CYQQDSYDZHYCCN-UHFFFAOYSA-N 0.000 claims 1
• OKDZCQWSGIGYBF-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[1-(trifluoromethyl)cyclopropyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC1(CC1)C(F)(F)F OKDZCQWSGIGYBF-UHFFFAOYSA-N 0.000 claims 1
• AJGOBFNSSPZHMR-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[1-(trifluoromethyl)cyclopropyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(CC3(CC3)C(F)(F)F)N2C=C1 AJGOBFNSSPZHMR-UHFFFAOYSA-N 0.000 claims 1
• KSPGNKUDAORPNU-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[2-(trifluoromethyl)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=C(C=CC=C1)C(F)(F)F KSPGNKUDAORPNU-UHFFFAOYSA-N 0.000 claims 1
• JIUXSFQBARSNLK-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[3-(trifluoromethoxy)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=CC(=CC=C1)OC(F)(F)F JIUXSFQBARSNLK-UHFFFAOYSA-N 0.000 claims 1
• GCMOKWDPYYQFJJ-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[3-(trifluoromethyl)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=CC(=CC=C1)C(F)(F)F GCMOKWDPYYQFJJ-UHFFFAOYSA-N 0.000 claims 1
• QXIJQGZSDIZHKX-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[4-(trifluoromethoxy)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=CC=C(C=C1)OC(F)(F)F QXIJQGZSDIZHKX-UHFFFAOYSA-N 0.000 claims 1
• MXUXKSXWMCLFIU-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[4-(trifluoromethyl)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC1=CC=C(C=C1)C(F)(F)F MXUXKSXWMCLFIU-UHFFFAOYSA-N 0.000 claims 1
• MBAJONYFMNHRMR-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[4-(trifluoromethyl)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=CC=C(C=C1)C(F)(F)F MBAJONYFMNHRMR-UHFFFAOYSA-N 0.000 claims 1
• ZAQOTTSSCWFOMK-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[4-(trifluoromethyl)pyrazol-1-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CN1N=CC(=C1)C(F)(F)F ZAQOTTSSCWFOMK-UHFFFAOYSA-N 0.000 claims 1
• LZMVAWRZRYPVFU-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[4-(trifluoromethyl)pyridin-2-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC=CC(=C1)C(F)(F)F LZMVAWRZRYPVFU-UHFFFAOYSA-N 0.000 claims 1
• IQYJBOCCAFUXEH-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[6-(trifluoromethyl)pyridin-2-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyridin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=C1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC(=CC=C1)C(F)(F)F IQYJBOCCAFUXEH-UHFFFAOYSA-N 0.000 claims 1
• VJYDXFJTKAGKFU-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[[6-(trifluoromethyl)pyridin-2-yl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=NC(=CC=C1)C(F)(F)F VJYDXFJTKAGKFU-UHFFFAOYSA-N 0.000 claims 1
• DMTHUMSVDAWJQP-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)-4-[3-[phenyl(piperidin-1-yl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(C(N3CCCCC3)C3=CC=CC=C3)N2C=C1 DMTHUMSVDAWJQP-UHFFFAOYSA-N 0.000 claims 1
• HAHDHSOVIHKVMX-UHFFFAOYSA-N N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound CN1N=CC=C1NC1=NC=CC=N1 HAHDHSOVIHKVMX-UHFFFAOYSA-N 0.000 claims 1
• DTPQQASTFUOZFY-UHFFFAOYSA-N N-(2-methyltriazol-4-yl)-4-[3-[(1-propan-2-ylcyclopropyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound C(C)(C)C1(CC1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=NN(N=C1)C DTPQQASTFUOZFY-UHFFFAOYSA-N 0.000 claims 1
• JPMHHPUIWYCXGK-UHFFFAOYSA-N N-(4-fluorophenyl)-2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]acetamide Chemical compound FC1=CC=C(C=C1)NC(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)=O JPMHHPUIWYCXGK-UHFFFAOYSA-N 0.000 claims 1
• VJJORXVSVWTIJA-UHFFFAOYSA-N N-(oxan-4-yl)-4-(3-phenyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)pyrimidin-2-amine Chemical compound C1(=CC=CC=C1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 VJJORXVSVWTIJA-UHFFFAOYSA-N 0.000 claims 1
• CZGIBSLQLBDQTL-UHFFFAOYSA-N N-(oxan-4-yl)-4-(3-piperidin-3-yl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)pyrimidin-2-amine Chemical compound N1CC(CCC1)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 CZGIBSLQLBDQTL-UHFFFAOYSA-N 0.000 claims 1
• YIUPASLXSGQIGI-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-(2-phenylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound C1(=CC=CC=C1)CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 YIUPASLXSGQIGI-UHFFFAOYSA-N 0.000 claims 1
• BIPSVEZBEQGRBR-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-(2-phenylpyrazol-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound C1(=CC=CC=C1)N1N=CC=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 BIPSVEZBEQGRBR-UHFFFAOYSA-N 0.000 claims 1
• JVMRBYVZECNRIM-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-(2-pyridin-2-ylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound N1=C(C=CC=C1)CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 JVMRBYVZECNRIM-UHFFFAOYSA-N 0.000 claims 1
• PYSUFODSKDXHDX-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-(2-pyridin-3-ylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound N1=CC(=CC=C1)CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 PYSUFODSKDXHDX-UHFFFAOYSA-N 0.000 claims 1
• IMPCHIPWTGYMQE-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-(2-pyridin-4-ylethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound N1=CC=C(C=C1)CCC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 IMPCHIPWTGYMQE-UHFFFAOYSA-N 0.000 claims 1
• IGUNXUFAOZPWBY-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-(5-phenyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound C1(=CC=CC=C1)C1=NNC=C1C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 IGUNXUFAOZPWBY-UHFFFAOYSA-N 0.000 claims 1
• NZIFNDYFESFOAP-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-(pyridin-2-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound N1=C(C=CC=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 NZIFNDYFESFOAP-UHFFFAOYSA-N 0.000 claims 1
• MLQHXRDQXNTCNX-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-(pyridin-3-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound N1=CC(=CC=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 MLQHXRDQXNTCNX-UHFFFAOYSA-N 0.000 claims 1
• HGSCXZPIVWKFPK-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-(pyridin-4-ylmethyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound N1=CC=C(C=C1)CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1CCOCC1 HGSCXZPIVWKFPK-UHFFFAOYSA-N 0.000 claims 1
• YPMPMYABRYFBPH-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-[4-(3,3,3-trifluoropropyl)morpholin-2-yl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound O1CCC(CC1)NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C1CN(CCO1)CCC(F)(F)F YPMPMYABRYFBPH-UHFFFAOYSA-N 0.000 claims 1
• PWOVDTAMPAFYBR-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-[[2-(trifluoromethyl)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound O1CCC(CC1)NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=C(C=CC=C1)C(F)(F)F PWOVDTAMPAFYBR-UHFFFAOYSA-N 0.000 claims 1
• CXXMKGJEUBGTOS-UHFFFAOYSA-N N-(oxan-4-yl)-4-[3-[[4-(trifluoromethoxy)phenyl]methyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]pyrimidin-2-amine Chemical compound O1CCC(CC1)NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC1=CC=C(C=C1)OC(F)(F)F CXXMKGJEUBGTOS-UHFFFAOYSA-N 0.000 claims 1
• QYESILPYRFSBFT-UHFFFAOYSA-N N-[1-(3-chloro-4-fluorophenyl)-2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]ethyl]acetamide Chemical compound ClC=1C=C(C=CC=1F)C(CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)NC(C)=O QYESILPYRFSBFT-UHFFFAOYSA-N 0.000 claims 1
• GFRZDTNUKIYXLI-UHFFFAOYSA-N N-[2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]-1-phenylethyl]acetamide Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)CC(C1=CC=CC=C1)NC(C)=O GFRZDTNUKIYXLI-UHFFFAOYSA-N 0.000 claims 1
• WJQVMYTUYZFNLW-UHFFFAOYSA-N N-methyl-7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridine-3-carboxamide Chemical compound CNC(=O)C1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C WJQVMYTUYZFNLW-UHFFFAOYSA-N 0.000 claims 1
• WLRFAYXOGPJRRN-UHFFFAOYSA-N [7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]-pyrrolidin-1-ylmethanone Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)C(=O)N1CCCC1 WLRFAYXOGPJRRN-UHFFFAOYSA-N 0.000 claims 1
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
• MPHWXORUAMKZIT-UHFFFAOYSA-N n-(oxan-4-yl)pyrimidin-2-amine Chemical compound C1COCCC1NC1=NC=CC=N1 MPHWXORUAMKZIT-UHFFFAOYSA-N 0.000 claims 1
• CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims 1
• 230000002685 pulmonary effect Effects 0.000 claims 1
• 230000002381 testicular Effects 0.000 claims 1
• 238000002560 therapeutic procedure Methods 0.000 claims 1
• 230000002265 prevention Effects 0.000 abstract description 4
• 238000003745 diagnosis Methods 0.000 abstract 1
• 238000001727 in vivo Methods 0.000 abstract 1
• 238000011065 in-situ storage Methods 0.000 abstract 1
• 230000001575 pathological effect Effects 0.000 abstract 1
• 239000000203 mixture Substances 0.000 description 133
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 116
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 104
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 95
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 74
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
• 235000019439 ethyl acetate Nutrition 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 37
• 238000005160 1H NMR spectroscopy Methods 0.000 description 36
• 238000006243 chemical reaction Methods 0.000 description 33
• 239000000243 solution Substances 0.000 description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
• 210000004027 cell Anatomy 0.000 description 24
• 239000007787 solid Substances 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
• 235000019341 magnesium sulphate Nutrition 0.000 description 21
• 239000002253 acid Substances 0.000 description 20
• 125000005843 halogen group Chemical group 0.000 description 20
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
• 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 description 19
• 102000007665 Extracellular Signal-Regulated MAP Kinases Human genes 0.000 description 19
• 239000012267 brine Substances 0.000 description 19
• 241000124008 Mammalia Species 0.000 description 18
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
• 239000010410 layer Substances 0.000 description 17
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
• 230000015572 biosynthetic process Effects 0.000 description 15
• 239000000543 intermediate Substances 0.000 description 15
• 239000003921 oil Substances 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 239000000047 product Substances 0.000 description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• 238000003556 assay Methods 0.000 description 12
• 239000003153 chemical reaction reagent Substances 0.000 description 12
• 238000000926 separation method Methods 0.000 description 12
• YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
• FXFHLUDXIDHSRR-UHFFFAOYSA-N Cn1nccc1Nc1nccc(n1)-c1cc[nH]c(c1)=N/N Chemical compound Cn1nccc1Nc1nccc(n1)-c1cc[nH]c(c1)=N/N FXFHLUDXIDHSRR-UHFFFAOYSA-N 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 10
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 125000003118 aryl group Chemical group 0.000 description 9
• 238000005859 coupling reaction Methods 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 8
• 239000000460 chlorine Chemical group 0.000 description 8
• 229910052801 chlorine Chemical group 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 238000003818 flash chromatography Methods 0.000 description 8
• 239000000463 material Substances 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• 239000000741 silica gel Substances 0.000 description 8
• 229910002027 silica gel Inorganic materials 0.000 description 8
• 229910052938 sodium sulfate Inorganic materials 0.000 description 8
• 235000011152 sodium sulphate Nutrition 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 8
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
• 239000007832 Na2SO4 Substances 0.000 description 7
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
• 238000002953 preparative HPLC Methods 0.000 description 7
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 7
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 6
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
• 208000002193 Pain Diseases 0.000 description 6
• BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
• 238000004440 column chromatography Methods 0.000 description 6
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 230000037361 pathway Effects 0.000 description 6
• 239000002953 phosphate buffered saline Substances 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 208000024891 symptom Diseases 0.000 description 6
• 238000004809 thin layer chromatography Methods 0.000 description 6
• 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 description 5
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
• AHMLFHMRRBJCRM-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)acetic acid Chemical compound CSC1=CC=C(CC(O)=O)C=C1 AHMLFHMRRBJCRM-UHFFFAOYSA-N 0.000 description 5
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
• PHEDXBVPIONUQT-UHFFFAOYSA-N Cocarcinogen A1 Natural products CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C1(OC(C)=O)C2(C)C PHEDXBVPIONUQT-UHFFFAOYSA-N 0.000 description 5
• 108040008097 MAP kinase activity proteins Proteins 0.000 description 5
• 102000019149 MAP kinase activity proteins Human genes 0.000 description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
• 229910000024 caesium carbonate Inorganic materials 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 238000004587 chromatography analysis Methods 0.000 description 5
• 239000012043 crude product Substances 0.000 description 5
• 208000037765 diseases and disorders Diseases 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
• 125000003566 oxetanyl group Chemical group 0.000 description 5
• PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 230000008569 process Effects 0.000 description 5
• 230000019491 signal transduction Effects 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 4
• 102100031181 Glyceraldehyde-3-phosphate dehydrogenase Human genes 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 4
• 230000002378 acidificating effect Effects 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• 150000001408 amides Chemical class 0.000 description 4
• 235000011114 ammonium hydroxide Nutrition 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
• 125000002619 bicyclic group Chemical group 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
• ZFDIRQKJPRINOQ-UHFFFAOYSA-N ethyl but-2-enoate Chemical compound CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 4
• 229960002949 fluorouracil Drugs 0.000 description 4
• 239000011521 glass Substances 0.000 description 4
• 108020004445 glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 4
• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• 239000003112 inhibitor Substances 0.000 description 4
• HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 4
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 4
• 230000001404 mediated effect Effects 0.000 description 4
• YVOAQDZUARKSRL-SNAWJCMRSA-N methyl (e)-4-methylpent-2-enoate Chemical compound COC(=O)\C=C\C(C)C YVOAQDZUARKSRL-SNAWJCMRSA-N 0.000 description 4
• 125000001624 naphthyl group Chemical group 0.000 description 4
• 239000012299 nitrogen atmosphere Substances 0.000 description 4
• 230000003287 optical effect Effects 0.000 description 4
• 239000001301 oxygen Substances 0.000 description 4
• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• 125000003386 piperidinyl group Chemical group 0.000 description 4
• 235000015320 potassium carbonate Nutrition 0.000 description 4
• 125000003226 pyrazolyl group Chemical group 0.000 description 4
• 238000004007 reversed phase HPLC Methods 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 239000000758 substrate Substances 0.000 description 4
• 239000011593 sulfur Chemical group 0.000 description 4
• WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 4
• WXGBZJJAGLSBPR-UHFFFAOYSA-N (2-fluoropyridin-4-yl)boronic acid Chemical compound OB(O)C1=CC=NC(F)=C1 WXGBZJJAGLSBPR-UHFFFAOYSA-N 0.000 description 3
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 description 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• KYNNBXCGXUOREX-UHFFFAOYSA-N 2-(3-bromophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1 KYNNBXCGXUOREX-UHFFFAOYSA-N 0.000 description 3
• LLOBDGYMMSDMEV-UHFFFAOYSA-N 2-benzyl-5-iodopyridazin-3-one Chemical compound O=C1C=C(I)C=NN1CC1=CC=CC=C1 LLOBDGYMMSDMEV-UHFFFAOYSA-N 0.000 description 3
• PTPTZLXZHPPVKG-UHFFFAOYSA-N 4-bromo-2-fluoropyridine Chemical compound FC1=CC(Br)=CC=N1 PTPTZLXZHPPVKG-UHFFFAOYSA-N 0.000 description 3
• UZWMMCWOUBWROK-UHFFFAOYSA-N 4-iodo-1h-pyridazin-6-one Chemical class IC=1C=NNC(=O)C=1 UZWMMCWOUBWROK-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
• 241000282414 Homo sapiens Species 0.000 description 3
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 3
• 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 3
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
• 229930012538 Paclitaxel Natural products 0.000 description 3
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
• 239000004809 Teflon Substances 0.000 description 3
• 229920006362 Teflon® Polymers 0.000 description 3
• FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 3
• DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
• 125000000304 alkynyl group Chemical group 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• 230000033115 angiogenesis Effects 0.000 description 3
• 229910052786 argon Inorganic materials 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• HXCHCVDVKSCDHU-LULTVBGHSA-N calicheamicin Chemical compound C1[C@H](OC)[C@@H](NCC)CO[C@H]1O[C@H]1[C@H](O[C@@H]2C\3=C(NC(=O)OC)C(=O)C[C@](C/3=C/CSSSC)(O)C#C\C=C/C#C2)O[C@H](C)[C@@H](NO[C@@H]2O[C@H](C)[C@@H](SC(=O)C=3C(=C(OC)C(O[C@H]4[C@@H]([C@H](OC)[C@@H](O)[C@H](C)O4)O)=C(I)C=3C)OC)[C@@H](O)C2)[C@@H]1O HXCHCVDVKSCDHU-LULTVBGHSA-N 0.000 description 3
• 229930195731 calicheamicin Natural products 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• 229940125898 compound 5 Drugs 0.000 description 3
• 238000010790 dilution Methods 0.000 description 3
• 239000012895 dilution Substances 0.000 description 3
• CINXGNHRKLMYRK-UHFFFAOYSA-N ethyl 2-cyclopropylideneacetate Chemical compound CCOC(=O)C=C1CC1 CINXGNHRKLMYRK-UHFFFAOYSA-N 0.000 description 3
• OIAFJKAMCULVJE-UHFFFAOYSA-N ethyl 4,4,5,5,5-pentafluoro-3-hydroxypentanoate Chemical compound CCOC(=O)CC(O)C(F)(F)C(F)(F)F OIAFJKAMCULVJE-UHFFFAOYSA-N 0.000 description 3
• 238000001640 fractional crystallisation Methods 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 125000004404 heteroalkyl group Chemical group 0.000 description 3
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
• 238000011534 incubation Methods 0.000 description 3
• 230000005764 inhibitory process Effects 0.000 description 3
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 3
• BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 description 3
• GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 3
• 229960000485 methotrexate Drugs 0.000 description 3
• QISLABNKAMRFPT-UHFFFAOYSA-N methyl 2-(4,4-difluorocyclohexyl)acetate Chemical compound COC(=O)CC1CCC(F)(F)CC1 QISLABNKAMRFPT-UHFFFAOYSA-N 0.000 description 3
• 230000004048 modification Effects 0.000 description 3
• 238000012986 modification Methods 0.000 description 3
• 239000012452 mother liquor Substances 0.000 description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 125000004123 n-propyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 208000002154 non-small cell lung carcinoma Diseases 0.000 description 3
• 229960001592 paclitaxel Drugs 0.000 description 3
• 239000012071 phase Substances 0.000 description 3
• 230000026731 phosphorylation Effects 0.000 description 3
• 238000006366 phosphorylation reaction Methods 0.000 description 3
• 125000006239 protecting group Chemical group 0.000 description 3
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
• 238000000746 purification Methods 0.000 description 3
• 125000004076 pyridyl group Chemical group 0.000 description 3
• 150000003254 radicals Chemical class 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• 125000004434 sulfur atom Chemical group 0.000 description 3
• 235000011149 sulphuric acid Nutrition 0.000 description 3
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
• 125000001425 triazolyl group Chemical group 0.000 description 3
• KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
• IGIDLTISMCAULB-YFKPBYRVSA-N (3s)-3-methylpentanoic acid Chemical compound CC[C@H](C)CC(O)=O IGIDLTISMCAULB-YFKPBYRVSA-N 0.000 description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 description 2
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
• GIGRWGTZFONRKA-UHFFFAOYSA-N 1-(bromomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CBr)C=C1 GIGRWGTZFONRKA-UHFFFAOYSA-N 0.000 description 2
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 2
• BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical class ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 2
• DIHBLPYATRFCCM-UHFFFAOYSA-N 2-(1-propan-2-yloxycyclopropyl)acetic acid Chemical compound C(C)(C)OC1(CC1)CC(=O)O DIHBLPYATRFCCM-UHFFFAOYSA-N 0.000 description 2
• MQIZLGQPDADKKW-UHFFFAOYSA-N 2-(4,4-difluorocyclohexyl)acetic acid Chemical compound OC(=O)CC1CCC(F)(F)CC1 MQIZLGQPDADKKW-UHFFFAOYSA-N 0.000 description 2
• GEIMWMFFBCMDFB-UHFFFAOYSA-N 2-(6-chloropyridin-2-yl)-N'-[4-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]pyridin-2-yl]acetohydrazide Chemical compound ClC1=CC=CC(=N1)CC(=O)NNC1=NC=CC(=C1)C1=NC(=NC=C1)NC1=CC=NN1C GEIMWMFFBCMDFB-UHFFFAOYSA-N 0.000 description 2
• MLGLMYYGCWPFOV-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methyl]-5-(2-methylsulfanylpyrimidin-4-yl)pyridazin-3-one Chemical compound COC1=CC=C(CN2N=CC(=CC2=O)C2=NC(=NC=C2)SC)C=C1 MLGLMYYGCWPFOV-UHFFFAOYSA-N 0.000 description 2
• BDTYVHBHUIRQIM-UHFFFAOYSA-N 2-[1-(2-methylpropoxy)cyclopropyl]acetic acid Chemical compound C(C(C)C)OC1(CC1)CC(=O)O BDTYVHBHUIRQIM-UHFFFAOYSA-N 0.000 description 2
• DWRYUBZHFBATBD-UHFFFAOYSA-N 2-[1-(trifluoromethyl)cyclobutyl]acetic acid Chemical compound FC(C1(CCC1)CC(=O)O)(F)F DWRYUBZHFBATBD-UHFFFAOYSA-N 0.000 description 2
• OZIJSVBXYXXOLD-UHFFFAOYSA-N 2-[1-(trifluoromethyl)cyclobutyl]acetonitrile Chemical compound FC(C1(CCC1)CC#N)(F)F OZIJSVBXYXXOLD-UHFFFAOYSA-N 0.000 description 2
• AJHBQZQCDCTOFD-UHFFFAOYSA-N 2-benzyl-4,5-dichloropyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1CC1=CC=CC=C1 AJHBQZQCDCTOFD-UHFFFAOYSA-N 0.000 description 2
• FDEAZDLUUDWXIE-UHFFFAOYSA-N 2-chloro-4-(2-fluoropyridin-4-yl)pyrimidine Chemical compound C1=NC(F)=CC(C=2N=C(Cl)N=CC=2)=C1 FDEAZDLUUDWXIE-UHFFFAOYSA-N 0.000 description 2
• JESRNIJXVIFVOV-UHFFFAOYSA-N 2-methylpyrazol-3-amine Chemical compound CN1N=CC=C1N JESRNIJXVIFVOV-UHFFFAOYSA-N 0.000 description 2
• FFQIQSUQSSESSS-UHFFFAOYSA-N 3,3-difluorobutanoic acid Chemical compound CC(F)(F)CC(O)=O FFQIQSUQSSESSS-UHFFFAOYSA-N 0.000 description 2
• IRFHYWBOWROGDC-UHFFFAOYSA-N 3-(2-fluoroethoxy)butanoic acid Chemical compound FCCOC(CC(=O)O)C IRFHYWBOWROGDC-UHFFFAOYSA-N 0.000 description 2
• IPGSVSITNZNQLD-UHFFFAOYSA-N 3-(3-fluorophenyl)-1,5-dimethylpyrazole-4-carboxylic acid Chemical compound CN1C(C)=C(C(O)=O)C(C=2C=C(F)C=CC=2)=N1 IPGSVSITNZNQLD-UHFFFAOYSA-N 0.000 description 2
• GXBJCFNNILMYPA-UHFFFAOYSA-N 3-(cyclopropylmethoxy)butanoic acid Chemical compound OC(=O)CC(C)OCC1CC1 GXBJCFNNILMYPA-UHFFFAOYSA-N 0.000 description 2
• UWBFKJIVHZZGHM-UHFFFAOYSA-N 3-(trifluoromethyl)pentanoic acid Chemical compound CCC(C(F)(F)F)CC(O)=O UWBFKJIVHZZGHM-UHFFFAOYSA-N 0.000 description 2
• CXQODPGMMDMGKR-UHFFFAOYSA-N 3-chloro-5-(2-methylsulfanylpyrimidin-4-yl)pyridazine Chemical compound ClC=1N=NC=C(C1)C1=NC(=NC=C1)SC CXQODPGMMDMGKR-UHFFFAOYSA-N 0.000 description 2
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
• FUFJVRUCYBOPHF-UHFFFAOYSA-N 3-cyclopropyl-3-methoxypropanoic acid Chemical compound OC(=O)CC(OC)C1CC1 FUFJVRUCYBOPHF-UHFFFAOYSA-N 0.000 description 2
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
• OHXIAMADVYIVGJ-UHFFFAOYSA-N 3-methoxy-4-methyl-N'-[4-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]pyridin-2-yl]pentanehydrazide Chemical compound COC(CC(=O)NNC1=NC=CC(=C1)C1=NC(=NC=C1)NC1=CC=NN1C)C(C)C OHXIAMADVYIVGJ-UHFFFAOYSA-N 0.000 description 2
• XJNXRENICWSAHP-UHFFFAOYSA-N 3-methoxy-4-methylpentanoic acid Chemical compound COC(C(C)C)CC(O)=O XJNXRENICWSAHP-UHFFFAOYSA-N 0.000 description 2
• WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
• OKLTXCRXJXJTDJ-UHFFFAOYSA-N 4-(2,3-difluoropyridin-4-yl)-N-(oxan-4-yl)pyridin-2-amine Chemical compound FC1=NC=CC(=C1F)C1=CC(=NC=C1)NC1CCOCC1 OKLTXCRXJXJTDJ-UHFFFAOYSA-N 0.000 description 2
• XNVILGQVSVJIIF-UHFFFAOYSA-N 4-(2-fluoropyridin-4-yl)-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound FC1=NC=CC(=C1)C1=CC(=NC=C1)NC1=CC=NN1C XNVILGQVSVJIIF-UHFFFAOYSA-N 0.000 description 2
• CCRACUQLURPMQO-UHFFFAOYSA-N 4-(2-fluoropyridin-4-yl)-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound FC1=NC=CC(=C1)C1=NC(=NC=C1)NC1=CC=NN1C CCRACUQLURPMQO-UHFFFAOYSA-N 0.000 description 2
• BHGCOOZXVLVPKM-UHFFFAOYSA-N 4-(2-hydrazinylpyridin-4-yl)-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound N(N)C1=NC=CC(=C1)C1=CC(=NC=C1)NC=1N(N=CC1)C BHGCOOZXVLVPKM-UHFFFAOYSA-N 0.000 description 2
• IJBXHMIMWJJESB-UHFFFAOYSA-N 4-(2-methylsulfanylpyrimidin-4-yl)-1H-pyridazin-6-one Chemical compound CSC1=NC=CC(=N1)C1=CC(NN=C1)=O IJBXHMIMWJJESB-UHFFFAOYSA-N 0.000 description 2
• ZGLRZSATOMFNTM-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-methyl-2h-furan-5-one Chemical compound C1=CC(OC)=CC=C1C1=C(C)COC1=O ZGLRZSATOMFNTM-UHFFFAOYSA-N 0.000 description 2
• PLRIUUDPEHQBNC-UHFFFAOYSA-N 4-bromo-N-(2-methylpyrazol-3-yl)pyridin-2-amine Chemical compound BrC1=CC(=NC=C1)NC=1N(N=CC1)C PLRIUUDPEHQBNC-UHFFFAOYSA-N 0.000 description 2
• QTGNVIGXFHEDCA-UHFFFAOYSA-N 4-bromo-n-(oxan-4-yl)pyridin-2-amine Chemical compound BrC1=CC=NC(NC2CCOCC2)=C1 QTGNVIGXFHEDCA-UHFFFAOYSA-N 0.000 description 2
• QGQRJEQRFXERSF-UHFFFAOYSA-N 4-fluoro-3-(fluoromethyl)butanoic acid Chemical compound OC(=O)CC(CF)CF QGQRJEQRFXERSF-UHFFFAOYSA-N 0.000 description 2
• NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 2
• DRZMZZCDQYCBGM-UHFFFAOYSA-N 5-iodo-2-[(4-methoxyphenyl)methyl]pyridazin-3-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C=C(I)C=N1 DRZMZZCDQYCBGM-UHFFFAOYSA-N 0.000 description 2
• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 2
• MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 description 2
• OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 2
• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 2
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical class [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
• 108010092160 Dactinomycin Proteins 0.000 description 2
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
• 239000012824 ERK inhibitor Substances 0.000 description 2
• VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 2
• 230000005526 G1 to G0 transition Effects 0.000 description 2
• 101001052493 Homo sapiens Mitogen-activated protein kinase 1 Proteins 0.000 description 2
• 101000984753 Homo sapiens Serine/threonine-protein kinase B-raf Proteins 0.000 description 2
• 206010061218 Inflammation Diseases 0.000 description 2
• 239000005551 L01XE03 - Erlotinib Substances 0.000 description 2
• 239000005511 L01XE05 - Sorafenib Substances 0.000 description 2
• 239000002136 L01XE07 - Lapatinib Substances 0.000 description 2
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
• 102000043136 MAP kinase family Human genes 0.000 description 2
• 108091054455 MAP kinase family Proteins 0.000 description 2
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
• 108700015928 Mitogen-activated protein kinase 13 Proteins 0.000 description 2
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
• FTXHKCJZICFOML-UHFFFAOYSA-N N'-[4-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]pyridin-2-yl]-2-(4-methylsulfanylphenyl)acetohydrazide Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC(=NC=C1)NNC(CC1=CC=C(C=C1)SC)=O FTXHKCJZICFOML-UHFFFAOYSA-N 0.000 description 2
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 2
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
• 229910019213 POCl3 Inorganic materials 0.000 description 2
• 108091000080 Phosphotransferase Proteins 0.000 description 2
• 229920001213 Polysorbate 20 Polymers 0.000 description 2
• 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 description 2
• 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 description 2
• LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
• 102100027103 Serine/threonine-protein kinase B-raf Human genes 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• 208000005718 Stomach Neoplasms Diseases 0.000 description 2
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 2
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 2
• UQSIEHVSHVIAPB-UHFFFAOYSA-N [1-(trifluoromethyl)cyclobutyl]methanol Chemical compound OCC1(C(F)(F)F)CCC1 UQSIEHVSHVIAPB-UHFFFAOYSA-N 0.000 description 2
• AGPWWILGGUBTKU-UHFFFAOYSA-N [1-(trifluoromethyl)cyclobutyl]methyl methanesulfonate Chemical compound CS(=O)(=O)OCC1(C(F)(F)F)CCC1 AGPWWILGGUBTKU-UHFFFAOYSA-N 0.000 description 2
• ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 2
• 230000002159 abnormal effect Effects 0.000 description 2
• WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 2
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
• 239000013543 active substance Substances 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• 125000000278 alkyl amino alkyl group Chemical group 0.000 description 2
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
• ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 2
• 229960003437 aminoglutethimide Drugs 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
• IGIDLTISMCAULB-UHFFFAOYSA-N anteisohexanoic acid Natural products CCC(C)CC(O)=O IGIDLTISMCAULB-UHFFFAOYSA-N 0.000 description 2
• 239000003242 anti bacterial agent Substances 0.000 description 2
• 230000001093 anti-cancer Effects 0.000 description 2
• 229940088710 antibiotic agent Drugs 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• MJOPETUIAAVFAQ-UHFFFAOYSA-N benzyl 4-fluoro-3-(fluoromethyl)but-2-enoate Chemical compound FCC(=CC(=O)OCC1=CC=CC=C1)CF MJOPETUIAAVFAQ-UHFFFAOYSA-N 0.000 description 2
• XIRIZTBJKNJGRI-UHFFFAOYSA-N benzyl 4-fluoro-3-(fluoromethyl)butanoate Chemical compound FCC(CC(=O)OCC1=CC=CC=C1)CF XIRIZTBJKNJGRI-UHFFFAOYSA-N 0.000 description 2
• 230000000903 blocking effect Effects 0.000 description 2
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 2
• 210000000481 breast Anatomy 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 230000004663 cell proliferation Effects 0.000 description 2
• 230000001413 cellular effect Effects 0.000 description 2
• 229940125758 compound 15 Drugs 0.000 description 2
• 229940126214 compound 3 Drugs 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
• STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 2
• 150000002085 enols Chemical group 0.000 description 2
• AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical class CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• HXBCPBSHJYHXQV-AATRIKPKSA-N ethyl (e)-3-cyclopropylprop-2-enoate Chemical compound CCOC(=O)\C=C\C1CC1 HXBCPBSHJYHXQV-AATRIKPKSA-N 0.000 description 2
• ZMFMGSXJZIKSDX-UHFFFAOYSA-N ethyl 3-(3-fluorophenyl)-1,5-dimethylpyrazole-4-carboxylate Chemical compound CCOC(=O)C1=C(C)N(C)N=C1C1=CC(F)=CC=C1 ZMFMGSXJZIKSDX-UHFFFAOYSA-N 0.000 description 2
• CQJZLAJDJHFQIE-UHFFFAOYSA-N ethyl 3-(trifluoromethyl)pent-2-enoate Chemical class CCOC(=O)C=C(CC)C(F)(F)F CQJZLAJDJHFQIE-UHFFFAOYSA-N 0.000 description 2
• 229940087476 femara Drugs 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
• 235000003599 food sweetener Nutrition 0.000 description 2
• 238000004508 fractional distillation Methods 0.000 description 2
• 230000006870 function Effects 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 2
• 206010017758 gastric cancer Diseases 0.000 description 2
• XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 2
• 150000004676 glycans Chemical class 0.000 description 2
• 229940093915 gynecological organic acid Drugs 0.000 description 2
• 230000002440 hepatic effect Effects 0.000 description 2
• 229960001101 ifosfamide Drugs 0.000 description 2
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 2
• YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
• 230000004054 inflammatory process Effects 0.000 description 2
• 125000000468 ketone group Chemical group 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 229960003881 letrozole Drugs 0.000 description 2
• 208000014018 liver neoplasm Diseases 0.000 description 2
• 210000004072 lung Anatomy 0.000 description 2
• 229960001428 mercaptopurine Drugs 0.000 description 2
• CSSDTWVHHFOMHI-UHFFFAOYSA-N methyl 3-cyclopropyl-3-methoxypropanoate Chemical compound COC(=O)CC(OC)C1CC1 CSSDTWVHHFOMHI-UHFFFAOYSA-N 0.000 description 2
• 229960001156 mitoxantrone Drugs 0.000 description 2
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 2
• 125000002950 monocyclic group Chemical group 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• 210000000214 mouth Anatomy 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• QZGIWPZCWHMVQL-UIYAJPBUSA-N neocarzinostatin chromophore Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3([C@@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-UIYAJPBUSA-N 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 150000002894 organic compounds Chemical class 0.000 description 2
• 229910052763 palladium Inorganic materials 0.000 description 2
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
• 230000008823 permeabilization Effects 0.000 description 2
• 239000000825 pharmaceutical preparation Substances 0.000 description 2
• 210000003800 pharynx Anatomy 0.000 description 2
• DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
• 125000003884 phenylalkyl group Chemical group 0.000 description 2
• 102000020233 phosphotransferase Human genes 0.000 description 2
• 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
• 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
• 229920001282 polysaccharide Polymers 0.000 description 2
• 239000005017 polysaccharide Substances 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 108090000765 processed proteins & peptides Proteins 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 2
• 125000003373 pyrazinyl group Chemical group 0.000 description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 229960004622 raloxifene Drugs 0.000 description 2
• GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 2
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 2
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 2
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 2
• 238000012552 review Methods 0.000 description 2
• 229940095743 selective estrogen receptor modulator Drugs 0.000 description 2
• 239000000333 selective estrogen receptor modulator Substances 0.000 description 2
• 238000010898 silica gel chromatography Methods 0.000 description 2
• 239000000377 silicon dioxide Substances 0.000 description 2
• 229960002930 sirolimus Drugs 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 230000000638 stimulation Effects 0.000 description 2
• 201000011549 stomach cancer Diseases 0.000 description 2
• PVYJZLYGTZKPJE-UHFFFAOYSA-N streptonigrin Chemical compound C=1C=C2C(=O)C(OC)=C(N)C(=O)C2=NC=1C(C=1N)=NC(C(O)=O)=C(C)C=1C1=CC=C(OC)C(OC)=C1O PVYJZLYGTZKPJE-UHFFFAOYSA-N 0.000 description 2
• 230000004083 survival effect Effects 0.000 description 2
• 239000003765 sweetening agent Substances 0.000 description 2
• FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 2
• LWKMTSRRGUVABD-UHFFFAOYSA-N tert-butyl 2-formylmorpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOC(C=O)C1 LWKMTSRRGUVABD-UHFFFAOYSA-N 0.000 description 2
• 238000012360 testing method Methods 0.000 description 2
• 229940124597 therapeutic agent Drugs 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• 125000000335 thiazolyl group Chemical group 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• 229960001196 thiotepa Drugs 0.000 description 2
• 229960003087 tioguanine Drugs 0.000 description 2
• 210000001519 tissue Anatomy 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 150000008523 triazolopyridines Chemical class 0.000 description 2
• 229960005486 vaccine Drugs 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
• IKVDXUFZJARKPF-UHFFFAOYSA-M zinc;cyclopropane;bromide Chemical compound Br[Zn+].C1C[CH-]1 IKVDXUFZJARKPF-UHFFFAOYSA-M 0.000 description 2
• NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 1
• RRDPWAPIJGSANI-SSDOTTSWSA-N (2r)-2-cyclohexyl-2-hydroxyacetic acid Chemical compound OC(=O)[C@H](O)C1CCCCC1 RRDPWAPIJGSANI-SSDOTTSWSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• FLWWDYNPWOSLEO-HQVZTVAUSA-N (2s)-2-[[4-[1-(2-amino-4-oxo-1h-pteridin-6-yl)ethyl-methylamino]benzoyl]amino]pentanedioic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1C(C)N(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FLWWDYNPWOSLEO-HQVZTVAUSA-N 0.000 description 1
• PAORVUMOXXAMPL-SECBINFHSA-N (2s)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride Chemical compound CO[C@](C(Cl)=O)(C(F)(F)F)C1=CC=CC=C1 PAORVUMOXXAMPL-SECBINFHSA-N 0.000 description 1
• CGMTUJFWROPELF-YPAAEMCBSA-N (3E,5S)-5-[(2S)-butan-2-yl]-3-(1-hydroxyethylidene)pyrrolidine-2,4-dione Chemical compound CC[C@H](C)[C@@H]1NC(=O)\C(=C(/C)O)C1=O CGMTUJFWROPELF-YPAAEMCBSA-N 0.000 description 1
• DWWCRHUNNQBQRA-ZDUSSCGKSA-N (3S)-3-hydroxy-N'-[4-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]pyridin-2-yl]pentanehydrazide Chemical compound O[C@H](CC(=O)NNC1=NC=CC(=C1)C1=NC(=NC=C1)NC1=CC=NN1C)CC DWWCRHUNNQBQRA-ZDUSSCGKSA-N 0.000 description 1
• TVIRNGFXQVMMGB-OFWIHYRESA-N (3s,6r,10r,13e,16s)-16-[(2r,3r,4s)-4-chloro-3-hydroxy-4-phenylbutan-2-yl]-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone Chemical compound C1=C(Cl)C(OC)=CC=C1C[C@@H]1C(=O)NC[C@@H](C)C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@H](C)[C@@H](O)[C@@H](Cl)C=2C=CC=CC=2)C/C=C/C(=O)N1 TVIRNGFXQVMMGB-OFWIHYRESA-N 0.000 description 1
• KIUPCUCGVCGPPA-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) carbonochloridate Chemical compound CC(C)C1CCC(C)CC1OC(Cl)=O KIUPCUCGVCGPPA-UHFFFAOYSA-N 0.000 description 1
• XRBSKUSTLXISAB-XVVDYKMHSA-N (5r,6r,7r,8r)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H](CO)[C@@H]2C(O)=O)=C1 XRBSKUSTLXISAB-XVVDYKMHSA-N 0.000 description 1
• XRBSKUSTLXISAB-UHFFFAOYSA-N (7R,7'R,8R,8'R)-form-Podophyllic acid Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C(CO)C2C(O)=O)=C1 XRBSKUSTLXISAB-UHFFFAOYSA-N 0.000 description 1
• INAUWOVKEZHHDM-PEDBPRJASA-N (7s,9s)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7-[(2r,4s,5s,6s)-5-hydroxy-6-methyl-4-morpholin-4-yloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCOCC1 INAUWOVKEZHHDM-PEDBPRJASA-N 0.000 description 1
• NOPNWHSMQOXAEI-PUCKCBAPSA-N (7s,9s)-7-[(2r,4s,5s,6s)-4-(2,3-dihydropyrrol-1-yl)-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCC=C1 NOPNWHSMQOXAEI-PUCKCBAPSA-N 0.000 description 1
• FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 1
• IEXUMDBQLIVNHZ-YOUGDJEHSA-N (8s,11r,13r,14s,17s)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(3-hydroxypropyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(O)CCCO)[C@@]2(C)C1 IEXUMDBQLIVNHZ-YOUGDJEHSA-N 0.000 description 1
• FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
• LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UWTATZPHSA-M (R)-lactate Chemical class C[C@@H](O)C([O-])=O JVTAAEKCZFNVCJ-UWTATZPHSA-M 0.000 description 1
• LVRFTAZAXQPQHI-YFKPBYRVSA-N (S)-2-hydroxy-4-methylpentanoic acid Chemical compound CC(C)C[C@H](O)C(O)=O LVRFTAZAXQPQHI-YFKPBYRVSA-N 0.000 description 1
• REKYPYSUBKSCAT-BYPYZUCNSA-N (S)-3-hydroxypentanoic acid Chemical compound CC[C@H](O)CC(O)=O REKYPYSUBKSCAT-BYPYZUCNSA-N 0.000 description 1
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
• MYKUKUCHPMASKF-VIFPVBQESA-N (S)-nornicotine Chemical compound C1CCN[C@@H]1C1=CC=CN=C1 MYKUKUCHPMASKF-VIFPVBQESA-N 0.000 description 1
• AGNGYMCLFWQVGX-AGFFZDDWSA-N (e)-1-[(2s)-2-amino-2-carboxyethoxy]-2-diazonioethenolate Chemical compound OC(=O)[C@@H](N)CO\C([O-])=C\[N+]#N AGNGYMCLFWQVGX-AGFFZDDWSA-N 0.000 description 1
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
• QBVHMPFSDVNFAY-UHFFFAOYSA-N 1,1,1-trifluorobutan-2-one Chemical compound CCC(=O)C(F)(F)F QBVHMPFSDVNFAY-UHFFFAOYSA-N 0.000 description 1
• FONKWHRXTPJODV-DNQXCXABSA-N 1,3-bis[2-[(8s)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydro-3h-pyrrolo[3,2-e]indole-6-carbonyl]-1h-indol-5-yl]urea Chemical compound C1([C@H](CCl)CN2C(=O)C=3NC4=CC=C(C=C4C=3)NC(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C4=CC(O)=C5NC=C(C5=C4[C@H](CCl)C3)C)=C2C=C(O)C2=C1C(C)=CN2 FONKWHRXTPJODV-DNQXCXABSA-N 0.000 description 1
• HKIPCXRNASWFRU-UHFFFAOYSA-N 1,3-difluoropropan-2-one Chemical compound FCC(=O)CF HKIPCXRNASWFRU-UHFFFAOYSA-N 0.000 description 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
• 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
• 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
• SDTORDSXCYSNTD-UHFFFAOYSA-N 1-methoxy-4-[(4-methoxyphenyl)methoxymethyl]benzene Chemical group C1=CC(OC)=CC=C1COCC1=CC=C(OC)C=C1 SDTORDSXCYSNTD-UHFFFAOYSA-N 0.000 description 1
• AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 1
• BTOTXLJHDSNXMW-POYBYMJQSA-N 2,3-dideoxyuridine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(=O)NC(=O)C=C1 BTOTXLJHDSNXMW-POYBYMJQSA-N 0.000 description 1
• BOMZMNZEXMAQQW-UHFFFAOYSA-N 2,5,11-trimethyl-6h-pyrido[4,3-b]carbazol-2-ium-9-ol;acetate Chemical compound CC([O-])=O.C[N+]1=CC=C2C(C)=C(NC=3C4=CC(O)=CC=3)C4=C(C)C2=C1 BOMZMNZEXMAQQW-UHFFFAOYSA-N 0.000 description 1
• SZDGQFPJGQOZGC-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-N'-[4-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]pyridin-2-yl]acetohydrazide Chemical compound BrC=1C=C(C=NC=1)CC(=O)NNC1=NC=CC(=C1)C1=NC(=NC=C1)NC1=CC=NN1C SZDGQFPJGQOZGC-UHFFFAOYSA-N 0.000 description 1
• UETIDNDXXGCJCE-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)acetic acid Chemical compound OC(=O)CC1=CN=CC(Br)=C1 UETIDNDXXGCJCE-UHFFFAOYSA-N 0.000 description 1
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
• QCXJFISCRQIYID-IAEPZHFASA-N 2-amino-1-n-[(3s,6s,7r,10s,16s)-3-[(2s)-butan-2-yl]-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-10-propan-2-yl-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-4,6-dimethyl-3-oxo-9-n-[(3s,6s,7r,10s,16s)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propa Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N=C2C(C(=O)N[C@@H]3C(=O)N[C@H](C(N4CCC[C@H]4C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]3C)=O)[C@@H](C)CC)=C(N)C(=O)C(C)=C2O2)C2=C(C)C=C1 QCXJFISCRQIYID-IAEPZHFASA-N 0.000 description 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
• AWLVTQRRKPBQEQ-UHFFFAOYSA-N 2-benzylsulfanylacetic acid Chemical compound OC(=O)CSCC1=CC=CC=C1 AWLVTQRRKPBQEQ-UHFFFAOYSA-N 0.000 description 1
• 125000005999 2-bromoethyl group Chemical group 0.000 description 1
• AXAQZUPPTUBENW-UHFFFAOYSA-N 2-chloro-1h-pyridazine Chemical compound ClN1NC=CC=C1 AXAQZUPPTUBENW-UHFFFAOYSA-N 0.000 description 1
• FDAYLTPAFBGXAB-UHFFFAOYSA-N 2-chloro-n,n-bis(2-chloroethyl)ethanamine Chemical compound ClCCN(CCCl)CCCl FDAYLTPAFBGXAB-UHFFFAOYSA-N 0.000 description 1
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
• UIOAYOIJMYMOEU-UHFFFAOYSA-N 2-fluoro-6-methoxybenzaldehyde Chemical compound COC1=CC=CC(F)=C1C=O UIOAYOIJMYMOEU-UHFFFAOYSA-N 0.000 description 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• SMJRBWINMFUUDS-UHFFFAOYSA-N 2-thienylacetic acid Chemical group OC(=O)CC1=CC=CS1 SMJRBWINMFUUDS-UHFFFAOYSA-N 0.000 description 1
• YIMDLWDNDGKDTJ-QLKYHASDSA-N 3'-deamino-3'-(3-cyanomorpholin-4-yl)doxorubicin Chemical compound N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCOCC1C#N YIMDLWDNDGKDTJ-QLKYHASDSA-N 0.000 description 1
• PLNJTJQKEPTIRY-UHFFFAOYSA-N 3-(3-chlorophenyl)-1,5-dimethylpyrazole-4-carboxylic acid Chemical compound ClC=1C=C(C=CC=1)C1=NN(C(=C1C(=O)O)C)C PLNJTJQKEPTIRY-UHFFFAOYSA-N 0.000 description 1
• PWMYMKOUNYTVQN-UHFFFAOYSA-N 3-(8,8-diethyl-2-aza-8-germaspiro[4.5]decan-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C1C[Ge](CC)(CC)CCC11CN(CCCN(C)C)CC1 PWMYMKOUNYTVQN-UHFFFAOYSA-N 0.000 description 1
• JZTPKAROPNTQQV-UHFFFAOYSA-N 3-fluorobenzonitrile Chemical compound FC1=CC=CC(C#N)=C1 JZTPKAROPNTQQV-UHFFFAOYSA-N 0.000 description 1
• AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
• ZYPIPHPPKPCWMR-UHFFFAOYSA-N 4,4,5,5,5-pentafluoro-3-hydroxypentanoic acid Chemical compound FC(C(CC(=O)O)O)(C(F)(F)F)F ZYPIPHPPKPCWMR-UHFFFAOYSA-N 0.000 description 1
• VJWXIRQLLGYIDI-UHFFFAOYSA-N 4,5-dichloro-1h-pyridazin-6-one Chemical compound OC1=NN=CC(Cl)=C1Cl VJWXIRQLLGYIDI-UHFFFAOYSA-N 0.000 description 1
• PMHDRJOEBSDGKK-UHFFFAOYSA-N 4-(2-hydrazinylpyridin-4-yl)-N-(1-methylpyrazol-4-yl)pyrimidin-2-amine Chemical compound N(N)C1=NC=CC(=C1)C1=NC(=NC=C1)NC=1C=NN(C1)C PMHDRJOEBSDGKK-UHFFFAOYSA-N 0.000 description 1
• AZDSUNOFVADTDU-UHFFFAOYSA-N 4-(2-hydrazinylpyridin-4-yl)-N-(oxan-4-yl)pyrimidin-2-amine Chemical group N(N)C1=NC=CC(=C1)C1=NC(=NC=C1)NC1CCOCC1 AZDSUNOFVADTDU-UHFFFAOYSA-N 0.000 description 1
• UAFICGOIFXAWEK-UHFFFAOYSA-N 4-(3-fluoro-2-hydrazinylpyridin-4-yl)-N-(oxan-4-yl)pyridin-2-amine Chemical compound FC=1C(=NC=CC1C1=CC(=NC=C1)NC1CCOCC1)NN UAFICGOIFXAWEK-UHFFFAOYSA-N 0.000 description 1
• CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 description 1
• DODQJNMQWMSYGS-QPLCGJKRSA-N 4-[(z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-phenylbut-1-en-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 DODQJNMQWMSYGS-QPLCGJKRSA-N 0.000 description 1
• IMYRHVKHGDGDDU-UHFFFAOYSA-N 4-[3-(2-methoxy-3-methylbutyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound COC(CC1=NN=C2C=C(C=CN12)C1=CC=NC(NC2=CC=NN2C)=N1)C(C)C IMYRHVKHGDGDDU-UHFFFAOYSA-N 0.000 description 1
• HRLWYDXJJGKPIR-CYBMUJFWSA-N 4-[3-[(2R)-2-fluorobutyl]-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-N-(2-methylpyrazol-3-yl)pyrimidin-2-amine Chemical compound F[C@@H](CC1=NN=C2N1C=CC(=C2)C1=NC(=NC=C1)NC1=CC=NN1C)CC HRLWYDXJJGKPIR-CYBMUJFWSA-N 0.000 description 1
• TVZGACDUOSZQKY-LBPRGKRZSA-N 4-aminofolic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 TVZGACDUOSZQKY-LBPRGKRZSA-N 0.000 description 1
• WJWYOXIYLBXRKS-UHFFFAOYSA-N 4-bis[4-(dimethylamino)phenyl]phosphoryl-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1P(=O)(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 WJWYOXIYLBXRKS-UHFFFAOYSA-N 0.000 description 1
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
• IDPUKCWIGUEADI-UHFFFAOYSA-N 5-[bis(2-chloroethyl)amino]uracil Chemical compound ClCCN(CCCl)C1=CNC(=O)NC1=O IDPUKCWIGUEADI-UHFFFAOYSA-N 0.000 description 1
• NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
• WYXSYVWAUAUWLD-SHUUEZRQSA-N 6-azauridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=N1 WYXSYVWAUAUWLD-SHUUEZRQSA-N 0.000 description 1
• VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 1
• ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 description 1
• CEIZFXOZIQNICU-UHFFFAOYSA-N Alternaria alternata Crofton-weed toxin Natural products CCC(C)C1NC(=O)C(C(C)=O)=C1O CEIZFXOZIQNICU-UHFFFAOYSA-N 0.000 description 1
• 206010061424 Anal cancer Diseases 0.000 description 1
• 108090000644 Angiozyme Proteins 0.000 description 1
• 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
• 102000014654 Aromatase Human genes 0.000 description 1
• 108010078554 Aromatase Proteins 0.000 description 1
• VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical compound CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 229940122361 Bisphosphonate Drugs 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• 238000007125 Buchwald synthesis reaction Methods 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
• DXPIOVPZSIXYIJ-KBPBESRZSA-N CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)[C@@H]1[C@H](C1)C(=O)OCC Chemical compound CN1N=CC=C1NC1=NC=CC(=N1)C1=CC=2N(C=C1)C(=NN=2)[C@@H]1[C@H](C1)C(=O)OCC DXPIOVPZSIXYIJ-KBPBESRZSA-N 0.000 description 1
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical class [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• SHHKQEUPHAENFK-UHFFFAOYSA-N Carboquone Chemical compound O=C1C(C)=C(N2CC2)C(=O)C(C(COC(N)=O)OC)=C1N1CC1 SHHKQEUPHAENFK-UHFFFAOYSA-N 0.000 description 1
• AOCCBINRVIKJHY-UHFFFAOYSA-N Carmofur Chemical compound CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O AOCCBINRVIKJHY-UHFFFAOYSA-N 0.000 description 1
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
• 108090000994 Catalytic RNA Proteins 0.000 description 1
• 102000053642 Catalytic RNA Human genes 0.000 description 1
• 241000700198 Cavia Species 0.000 description 1
• 108010001857 Cell Surface Receptors Proteins 0.000 description 1
• 206010008342 Cervix carcinoma Diseases 0.000 description 1
• JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
• MKQWTWSXVILIKJ-LXGUWJNJSA-N Chlorozotocin Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)NC(=O)N(N=O)CCCl MKQWTWSXVILIKJ-LXGUWJNJSA-N 0.000 description 1
• 235000001258 Cinchona calisaya Nutrition 0.000 description 1
• 241000699800 Cricetinae Species 0.000 description 1
• 229930188224 Cryptophycin Natural products 0.000 description 1
• VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
• DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical class OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical class OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
• FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical class [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 1
• WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
• NNJPGOLRFBJNIW-UHFFFAOYSA-N Demecolcine Natural products C1=C(OC)C(=O)C=C2C(NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-UHFFFAOYSA-N 0.000 description 1
• 108010002156 Depsipeptides Proteins 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• AUGQEEXBDZWUJY-ZLJUKNTDSA-N Diacetoxyscirpenol Chemical compound C([C@]12[C@]3(C)[C@H](OC(C)=O)[C@@H](O)[C@H]1O[C@@H]1C=C(C)CC[C@@]13COC(=O)C)O2 AUGQEEXBDZWUJY-ZLJUKNTDSA-N 0.000 description 1
• 101000876610 Dictyostelium discoideum Extracellular signal-regulated kinase 2 Proteins 0.000 description 1
• ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 1
• 102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 description 1
• 101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 description 1
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
• 229930193152 Dynemicin Natural products 0.000 description 1
• 206010014733 Endometrial cancer Diseases 0.000 description 1
• 206010014759 Endometrial neoplasm Diseases 0.000 description 1
• AFMYMMXSQGUCBK-UHFFFAOYSA-N Endynamicin A Natural products C1#CC=CC#CC2NC(C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(O)=C3)=C3C34OC32C(C)C(C(O)=O)=C(OC)C41 AFMYMMXSQGUCBK-UHFFFAOYSA-N 0.000 description 1
• SAMRUMKYXPVKPA-VFKOLLTISA-N Enocitabine Chemical compound O=C1N=C(NC(=O)CCCCCCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 SAMRUMKYXPVKPA-VFKOLLTISA-N 0.000 description 1
• HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
• OBMLHUPNRURLOK-XGRAFVIBSA-N Epitiostanol Chemical compound C1[C@@H]2S[C@@H]2C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 OBMLHUPNRURLOK-XGRAFVIBSA-N 0.000 description 1
• 241000588724 Escherichia coli Species 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
• BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 description 1
• 108010069236 Goserelin Proteins 0.000 description 1
• 239000007995 HEPES buffer Substances 0.000 description 1
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
• MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 description 1
• XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
• XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
• 206010065390 Inflammatory pain Diseases 0.000 description 1
• 102100023012 Kallistatin Human genes 0.000 description 1
• 229930194542 Keto Natural products 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical class OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical class C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical class [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
• 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
• 239000002147 L01XE04 - Sunitinib Substances 0.000 description 1
• JLERVPBPJHKRBJ-UHFFFAOYSA-N LY 117018 Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(O)C=C2S1 JLERVPBPJHKRBJ-UHFFFAOYSA-N 0.000 description 1
• 229920001491 Lentinan Polymers 0.000 description 1
• 108010000817 Leuprolide Proteins 0.000 description 1
• GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• 108060006687 MAP kinase kinase kinase Proteins 0.000 description 1
• 230000037364 MAPK/ERK pathway Effects 0.000 description 1
• 229940124647 MEK inhibitor Drugs 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical class [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
• 229930126263 Maytansine Natural products 0.000 description 1
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
• IVDYZAAPOLNZKG-KWHRADDSSA-N Mepitiostane Chemical compound O([C@@H]1[C@]2(CC[C@@H]3[C@@]4(C)C[C@H]5S[C@H]5C[C@@H]4CC[C@H]3[C@@H]2CC1)C)C1(OC)CCCC1 IVDYZAAPOLNZKG-KWHRADDSSA-N 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• VFKZTMPDYBFSTM-KVTDHHQDSA-N Mitobronitol Chemical compound BrC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-KVTDHHQDSA-N 0.000 description 1
• 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 1
• 229930192392 Mitomycin Natural products 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 description 1
• KGTDRFCXGRULNK-UHFFFAOYSA-N Nogalamycin Natural products COC1C(OC)(C)C(OC)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=C4C5(C)OC(C(C(C5O)N(C)C)O)OC4=C3C3=O)=C3C=C2C(C(=O)OC)C(C)(O)C1 KGTDRFCXGRULNK-UHFFFAOYSA-N 0.000 description 1
• 239000006057 Non-nutritive feed additive Substances 0.000 description 1
• MYKUKUCHPMASKF-UHFFFAOYSA-N Nornicotine Natural products C1CCNC1C1=CC=CN=C1 MYKUKUCHPMASKF-UHFFFAOYSA-N 0.000 description 1
• QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
• 229920003189 Nylon 4,6 Polymers 0.000 description 1
• VNPGTICXGLGIHA-UHFFFAOYSA-N OBOC1=CC=CN=C1F Chemical compound OBOC1=CC=CN=C1F VNPGTICXGLGIHA-UHFFFAOYSA-N 0.000 description 1
• 229930187135 Olivomycin Natural products 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• VREZDOWOLGNDPW-ALTGWBOUSA-N Pancratistatin Chemical compound C1=C2[C@H]3[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)[C@@H]3NC(=O)C2=C(O)C2=C1OCO2 VREZDOWOLGNDPW-ALTGWBOUSA-N 0.000 description 1
• VREZDOWOLGNDPW-MYVCAWNPSA-N Pancratistatin Natural products O=C1N[C@H]2[C@H](O)[C@H](O)[C@H](O)[C@H](O)[C@@H]2c2c1c(O)c1OCOc1c2 VREZDOWOLGNDPW-MYVCAWNPSA-N 0.000 description 1
• 229910002666 PdCl2 Inorganic materials 0.000 description 1
• YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
• 108010057150 Peplomycin Proteins 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
• KMSKQZKKOZQFFG-HSUXVGOQSA-N Pirarubicin Chemical compound O([C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1CCCCO1 KMSKQZKKOZQFFG-HSUXVGOQSA-N 0.000 description 1
• 239000004743 Polypropylene Substances 0.000 description 1
• HRHKSTOGXBBQCB-UHFFFAOYSA-N Porfiromycine Chemical compound O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 description 1
• HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 1
• 241000288906 Primates Species 0.000 description 1
• 102100024924 Protein kinase C alpha type Human genes 0.000 description 1
• 101710109947 Protein kinase C alpha type Proteins 0.000 description 1
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• 108091005682 Receptor kinases Proteins 0.000 description 1
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
• 208000006265 Renal cell carcinoma Diseases 0.000 description 1
• OWPCHSCAPHNHAV-UHFFFAOYSA-N Rhizoxin Natural products C1C(O)C2(C)OC2C=CC(C)C(OC(=O)C2)CC2CC2OC2C(=O)OC1C(C)C(OC)C(C)=CC=CC(C)=CC1=COC(C)=N1 OWPCHSCAPHNHAV-UHFFFAOYSA-N 0.000 description 1
• NSFWWJIQIKBZMJ-YKNYLIOZSA-N Roridin A Chemical compound C([C@]12[C@]3(C)[C@H]4C[C@H]1O[C@@H]1C=C(C)CC[C@@]13COC(=O)[C@@H](O)[C@H](C)CCO[C@H](\C=C\C=C/C(=O)O4)[C@H](O)C)O2 NSFWWJIQIKBZMJ-YKNYLIOZSA-N 0.000 description 1
• 206010061934 Salivary gland cancer Diseases 0.000 description 1
• 229940124639 Selective inhibitor Drugs 0.000 description 1
• 201000010208 Seminoma Diseases 0.000 description 1
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
• 208000000453 Skin Neoplasms Diseases 0.000 description 1
• 206010041067 Small cell lung cancer Diseases 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 238000006069 Suzuki reaction reaction Methods 0.000 description 1
• BXFOFFBJRFZBQZ-QYWOHJEZSA-N T-2 toxin Chemical compound C([C@@]12[C@]3(C)[C@H](OC(C)=O)[C@@H](O)[C@H]1O[C@H]1[C@]3(COC(C)=O)C[C@@H](C(=C1)C)OC(=O)CC(C)C)O2 BXFOFFBJRFZBQZ-QYWOHJEZSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• CGMTUJFWROPELF-UHFFFAOYSA-N Tenuazonic acid Natural products CCC(C)C1NC(=O)C(=C(C)/O)C1=O CGMTUJFWROPELF-UHFFFAOYSA-N 0.000 description 1
• 101710183280 Topoisomerase Proteins 0.000 description 1
• IWEQQRMGNVVKQW-OQKDUQJOSA-N Toremifene citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 IWEQQRMGNVVKQW-OQKDUQJOSA-N 0.000 description 1
• UMILHIMHKXVDGH-UHFFFAOYSA-N Triethylene glycol diglycidyl ether Chemical compound C1OC1COCCOCCOCCOCC1CO1 UMILHIMHKXVDGH-UHFFFAOYSA-N 0.000 description 1
• FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 description 1
• 229920004890 Triton X-100 Polymers 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
• 206010047741 Vulval cancer Diseases 0.000 description 1
• 208000004354 Vulvar Neoplasms Diseases 0.000 description 1
• ZYVSOIYQKUDENJ-ASUJBHBQSA-N [(2R,3R,4R,6R)-6-[[(6S,7S)-6-[(2S,4R,5R,6R)-4-[(2R,4R,5R,6R)-4-[(2S,4S,5S,6S)-5-acetyloxy-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-7-[(3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-4,10-dihydroxy-3-methyl-5-oxo-7,8-dihydro-6H-anthracen-2-yl]oxy]-4-[(2R,4R,5R,6R)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy-2-methyloxan-3-yl] acetate Chemical class COC([C@@H]1Cc2cc3cc(O[C@@H]4C[C@@H](O[C@@H]5C[C@@H](O)[C@@H](OC)[C@@H](C)O5)[C@H](OC(C)=O)[C@@H](C)O4)c(C)c(O)c3c(O)c2C(=O)[C@H]1O[C@H]1C[C@@H](O[C@@H]2C[C@@H](O[C@H]3C[C@](C)(O)[C@@H](OC(C)=O)[C@H](C)O3)[C@H](O)[C@@H](C)O2)[C@H](O)[C@@H](C)O1)C(=O)[C@@H](O)[C@@H](C)O ZYVSOIYQKUDENJ-ASUJBHBQSA-N 0.000 description 1
• SPJCRMJCFSJKDE-ZWBUGVOYSA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] 2-[4-[bis(2-chloroethyl)amino]phenyl]acetate Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)C(=O)CC1=CC=C(N(CCCl)CCCl)C=C1 SPJCRMJCFSJKDE-ZWBUGVOYSA-N 0.000 description 1
• IFJUINDAXYAPTO-UUBSBJJBSA-N [(8r,9s,13s,14s,17s)-17-[2-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyloxy]acetyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4OC(=O)COC(=O)CCCC=1C=CC(=CC=1)N(CCCl)CCCl)C)CC2=CC=3OC(=O)C1=CC=CC=C1 IFJUINDAXYAPTO-UUBSBJJBSA-N 0.000 description 1
• YRACHDVMKITFAZ-UHFFFAOYSA-N [1,2,4]triazolo[4,3-b]pyridazine Chemical class C1=CC=NN2C=NN=C21 YRACHDVMKITFAZ-UHFFFAOYSA-N 0.000 description 1
• XZSRRNFBEIOBDA-CFNBKWCHSA-N [2-[(2s,4s)-4-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]-2-oxoethyl] 2,2-diethoxyacetate Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)C(OCC)OCC)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 XZSRRNFBEIOBDA-CFNBKWCHSA-N 0.000 description 1
• NCHNHUJFGVPJJD-UHFFFAOYSA-N [5-(2-methylsulfanylpyrimidin-4-yl)pyridazin-3-yl]hydrazine Chemical compound N(N)C=1N=NC=C(C1)C1=NC(=NC=C1)SC NCHNHUJFGVPJJD-UHFFFAOYSA-N 0.000 description 1
• BBKCOQYMKGEAAJ-UHFFFAOYSA-M [Br-].[Zn+]C1CCC1 Chemical compound [Br-].[Zn+]C1CCC1 BBKCOQYMKGEAAJ-UHFFFAOYSA-M 0.000 description 1
• AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 description 1
• 108010023617 abarelix Proteins 0.000 description 1
• 229960002184 abarelix Drugs 0.000 description 1
• 229940028652 abraxane Drugs 0.000 description 1
• ZOZKYEHVNDEUCO-XUTVFYLZSA-N aceglatone Chemical compound O1C(=O)[C@H](OC(C)=O)[C@@H]2OC(=O)[C@@H](OC(=O)C)[C@@H]21 ZOZKYEHVNDEUCO-XUTVFYLZSA-N 0.000 description 1
• 229950002684 aceglatone Drugs 0.000 description 1
• IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
• SAIXAWJRUGENIS-UHFFFAOYSA-N acetohydrazide Chemical compound CC(=O)NN.CC(=O)NN SAIXAWJRUGENIS-UHFFFAOYSA-N 0.000 description 1
• 229930183665 actinomycin Natural products 0.000 description 1
• RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 229950004955 adozelesin Drugs 0.000 description 1
• BYRVKDUQDLJUBX-JJCDCTGGSA-N adozelesin Chemical compound C1=CC=C2OC(C(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C[C@H]4C[C@]44C5=C(C(C=C43)=O)NC=C5C)=CC2=C1 BYRVKDUQDLJUBX-JJCDCTGGSA-N 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 230000002411 adverse Effects 0.000 description 1
• 108700025316 aldesleukin Proteins 0.000 description 1
• 150000001336 alkenes Chemical class 0.000 description 1
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
• 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
• 150000008052 alkyl sulfonates Chemical class 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
• LVRFTAZAXQPQHI-UHFFFAOYSA-N alpha-hydroxyisocaproic acid Natural products CC(C)CC(O)C(O)=O LVRFTAZAXQPQHI-UHFFFAOYSA-N 0.000 description 1
• 229960000473 altretamine Drugs 0.000 description 1
• 150000001409 amidines Chemical class 0.000 description 1
• 125000004103 aminoalkyl group Chemical group 0.000 description 1
• 229960002749 aminolevulinic acid Drugs 0.000 description 1
• 229960003896 aminopterin Drugs 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 229940025084 amphetamine Drugs 0.000 description 1
• 229960001220 amsacrine Drugs 0.000 description 1
• XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
• 201000007538 anal carcinoma Diseases 0.000 description 1
• 229960002932 anastrozole Drugs 0.000 description 1
• YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
• BBDAGFIXKZCXAH-CCXZUQQUSA-N ancitabine Chemical compound N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 BBDAGFIXKZCXAH-CCXZUQQUSA-N 0.000 description 1
• 229950000242 ancitabine Drugs 0.000 description 1
• 239000004037 angiogenesis inhibitor Substances 0.000 description 1
• 230000002280 anti-androgenic effect Effects 0.000 description 1
• 229940124650 anti-cancer therapies Drugs 0.000 description 1
• 229940046836 anti-estrogen Drugs 0.000 description 1
• 230000001833 anti-estrogenic effect Effects 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• 239000000051 antiandrogen Substances 0.000 description 1
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
• 238000011319 anticancer therapy Methods 0.000 description 1
• 239000013059 antihormonal agent Substances 0.000 description 1
• 229940100197 antimetabolite Drugs 0.000 description 1
• 239000002256 antimetabolite Substances 0.000 description 1
• 229940045686 antimetabolites antineoplastic purine analogs Drugs 0.000 description 1
• 229940045687 antimetabolites folic acid analogs Drugs 0.000 description 1
• 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 1
• 229940045713 antineoplastic alkylating drug ethylene imines Drugs 0.000 description 1
• 229940045688 antineoplastic antimetabolites pyrimidine analogues Drugs 0.000 description 1
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 239000000074 antisense oligonucleotide Substances 0.000 description 1
• 238000012230 antisense oligonucleotides Methods 0.000 description 1
• 150000008209 arabinosides Chemical class 0.000 description 1
• 229940087620 aromasin Drugs 0.000 description 1
• 239000003886 aromatase inhibitor Substances 0.000 description 1
• 229940046844 aromatase inhibitors Drugs 0.000 description 1
• 125000003710 aryl alkyl group Chemical group 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 229940120638 avastin Drugs 0.000 description 1
• 229960002756 azacitidine Drugs 0.000 description 1
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
• 229950011321 azaserine Drugs 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 150000001541 aziridines Chemical class 0.000 description 1
• 125000004069 aziridinyl group Chemical group 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical class [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• INKMLGJBBDRIQR-UHFFFAOYSA-N benzyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)=CC(=O)OCC1=CC=CC=C1 INKMLGJBBDRIQR-UHFFFAOYSA-N 0.000 description 1
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
• 229960000397 bevacizumab Drugs 0.000 description 1
• 229960000997 bicalutamide Drugs 0.000 description 1
• 210000000941 bile Anatomy 0.000 description 1
• 230000027455 binding Effects 0.000 description 1
• 238000004166 bioassay Methods 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 229950008548 bisantrene Drugs 0.000 description 1
• 150000004663 bisphosphonates Chemical class 0.000 description 1
• 229950006844 bizelesin Drugs 0.000 description 1
• 201000001531 bladder carcinoma Diseases 0.000 description 1
• 201000000053 blastoma Diseases 0.000 description 1
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical class 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 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
• 229960001467 bortezomib Drugs 0.000 description 1
• 210000000133 brain stem Anatomy 0.000 description 1
• RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
• RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
• 229960005520 bryostatin Drugs 0.000 description 1
• MJQUEDHRCUIRLF-TVIXENOKSA-N bryostatin 1 Chemical compound C([C@@H]1CC(/[C@@H]([C@@](C(C)(C)/C=C/2)(O)O1)OC(=O)/C=C/C=C/CCC)=C\C(=O)OC)[C@H]([C@@H](C)O)OC(=O)C[C@H](O)C[C@@H](O1)C[C@H](OC(C)=O)C(C)(C)[C@]1(O)C[C@@H]1C\C(=C\C(=O)OC)C[C@H]\2O1 MJQUEDHRCUIRLF-TVIXENOKSA-N 0.000 description 1
• MUIWQCKLQMOUAT-AKUNNTHJSA-N bryostatin 20 Natural products COC(=O)C=C1C[C@@]2(C)C[C@]3(O)O[C@](C)(C[C@@H](O)CC(=O)O[C@](C)(C[C@@]4(C)O[C@](O)(CC5=CC(=O)O[C@]45C)C(C)(C)C=C[C@@](C)(C1)O2)[C@@H](C)O)C[C@H](OC(=O)C(C)(C)C)C3(C)C MUIWQCKLQMOUAT-AKUNNTHJSA-N 0.000 description 1
• 239000004067 bulking agent Substances 0.000 description 1
• 229960002092 busulfan Drugs 0.000 description 1
• 108700002839 cactinomycin Proteins 0.000 description 1
• 229950009908 cactinomycin Drugs 0.000 description 1
• IVFYLRMMHVYGJH-PVPPCFLZSA-N calusterone Chemical compound C1C[C@]2(C)[C@](O)(C)CC[C@H]2[C@@H]2[C@@H](C)CC3=CC(=O)CC[C@]3(C)[C@H]21 IVFYLRMMHVYGJH-PVPPCFLZSA-N 0.000 description 1
• 229950009823 calusterone Drugs 0.000 description 1
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
• 229940127093 camptothecin Drugs 0.000 description 1
• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
• 229960004117 capecitabine Drugs 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 150000001721 carbon Chemical group 0.000 description 1
• 229960004562 carboplatin Drugs 0.000 description 1
• 229960002115 carboquone Drugs 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 229960003261 carmofur Drugs 0.000 description 1
• 229960005243 carmustine Drugs 0.000 description 1
• BBZDXMBRAFTCAA-AREMUKBSSA-N carzelesin Chemical compound C1=2NC=C(C)C=2C([C@H](CCl)CN2C(=O)C=3NC4=CC=C(C=C4C=3)NC(=O)C3=CC4=CC=C(C=C4O3)N(CC)CC)=C2C=C1OC(=O)NC1=CC=CC=C1 BBZDXMBRAFTCAA-AREMUKBSSA-N 0.000 description 1
• 229950007509 carzelesin Drugs 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 230000022131 cell cycle Effects 0.000 description 1
• 230000010261 cell growth Effects 0.000 description 1
• 230000005754 cellular signaling Effects 0.000 description 1
• 210000003169 central nervous system Anatomy 0.000 description 1
• 201000010881 cervical cancer Diseases 0.000 description 1
• 210000003679 cervix uteri Anatomy 0.000 description 1
• 238000001311 chemical methods and process Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 230000000973 chemotherapeutic effect Effects 0.000 description 1
• 229960004630 chlorambucil Drugs 0.000 description 1
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
• BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
• 229960001480 chlorozotocin Drugs 0.000 description 1
• LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 238000002983 circular dichroism Methods 0.000 description 1
• 229960004316 cisplatin Drugs 0.000 description 1
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
• ACSIXWWBWUQEHA-UHFFFAOYSA-N clodronic acid Chemical compound OP(O)(=O)C(Cl)(Cl)P(O)(O)=O ACSIXWWBWUQEHA-UHFFFAOYSA-N 0.000 description 1
• 229960002286 clodronic acid Drugs 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 238000002648 combination therapy Methods 0.000 description 1
• 230000000295 complement effect Effects 0.000 description 1
• 229940125904 compound 1 Drugs 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 229940125810 compound 20 Drugs 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000007822 coupling agent Substances 0.000 description 1
• 108010089438 cryptophycin 1 Proteins 0.000 description 1
• PSNOPSMXOBPNNV-VVCTWANISA-N cryptophycin 1 Chemical compound C1=C(Cl)C(OC)=CC=C1C[C@@H]1C(=O)NC[C@@H](C)C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@H](C)[C@@H]2[C@H](O2)C=2C=CC=CC=2)C/C=C/C(=O)N1 PSNOPSMXOBPNNV-VVCTWANISA-N 0.000 description 1
• 108010090203 cryptophycin 8 Proteins 0.000 description 1
• PSNOPSMXOBPNNV-UHFFFAOYSA-N cryptophycin-327 Natural products C1=C(Cl)C(OC)=CC=C1CC1C(=O)NCC(C)C(=O)OC(CC(C)C)C(=O)OC(C(C)C2C(O2)C=2C=CC=CC=2)CC=CC(=O)N1 PSNOPSMXOBPNNV-UHFFFAOYSA-N 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 description 1
• GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 1
• 229960000684 cytarabine Drugs 0.000 description 1
• 229940104302 cytosine Drugs 0.000 description 1
• 230000003436 cytoskeletal effect Effects 0.000 description 1
• KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
• 229960003901 dacarbazine Drugs 0.000 description 1
• 229960000640 dactinomycin Drugs 0.000 description 1
• 229960000975 daunorubicin Drugs 0.000 description 1
• 229960005052 demecolcine Drugs 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 229950003913 detorubicin Drugs 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
• WVYXNIXAMZOZFK-UHFFFAOYSA-N diaziquone Chemical compound O=C1C(NC(=O)OCC)=C(N2CC2)C(=O)C(NC(=O)OCC)=C1N1CC1 WVYXNIXAMZOZFK-UHFFFAOYSA-N 0.000 description 1
• 229950002389 diaziquone Drugs 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
• 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
• 229960003668 docetaxel Drugs 0.000 description 1
• AMRJKAQTDDKMCE-UHFFFAOYSA-N dolastatin Chemical compound CC(C)C(N(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(C(C)C)C(OC)CC(=O)N1CCCC1C(OC)C(C)C(=O)NC(C=1SC=CN=1)CC1=CC=CC=C1 AMRJKAQTDDKMCE-UHFFFAOYSA-N 0.000 description 1
• 229930188854 dolastatin Natural products 0.000 description 1
• 239000002552 dosage form Substances 0.000 description 1
• 230000007783 downstream signaling Effects 0.000 description 1
• ZWAOHEXOSAUJHY-ZIYNGMLESA-N doxifluridine Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ZWAOHEXOSAUJHY-ZIYNGMLESA-N 0.000 description 1
• 229950005454 doxifluridine Drugs 0.000 description 1
• 229960004679 doxorubicin Drugs 0.000 description 1
• 229950004203 droloxifene Drugs 0.000 description 1
• NOTIQUSPUUHHEH-UXOVVSIBSA-N dromostanolone propionate Chemical compound C([C@@H]1CC2)C(=O)[C@H](C)C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](OC(=O)CC)[C@@]2(C)CC1 NOTIQUSPUUHHEH-UXOVVSIBSA-N 0.000 description 1
• 229950004683 drostanolone propionate Drugs 0.000 description 1
• 238000012377 drug delivery Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 229960005501 duocarmycin Drugs 0.000 description 1
• VQNATVDKACXKTF-XELLLNAOSA-N duocarmycin Chemical compound COC1=C(OC)C(OC)=C2NC(C(=O)N3C4=CC(=O)C5=C([C@@]64C[C@@H]6C3)C=C(N5)C(=O)OC)=CC2=C1 VQNATVDKACXKTF-XELLLNAOSA-N 0.000 description 1
• 229930184221 duocarmycin Natural products 0.000 description 1
• AFMYMMXSQGUCBK-AKMKHHNQSA-N dynemicin a Chemical compound C1#C\C=C/C#C[C@@H]2NC(C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(O)=C3)=C3[C@@]34O[C@]32[C@@H](C)C(C(O)=O)=C(OC)[C@H]41 AFMYMMXSQGUCBK-AKMKHHNQSA-N 0.000 description 1
• FSIRXIHZBIXHKT-MHTVFEQDSA-N edatrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CC(CC)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FSIRXIHZBIXHKT-MHTVFEQDSA-N 0.000 description 1
• 229950006700 edatrexate Drugs 0.000 description 1
• VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 description 1
• 229920001971 elastomer Polymers 0.000 description 1
• 229950000549 elliptinium acetate Drugs 0.000 description 1
• 229940120655 eloxatin Drugs 0.000 description 1
• 201000008184 embryoma Diseases 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 201000003914 endometrial carcinoma Diseases 0.000 description 1
• 230000002357 endometrial effect Effects 0.000 description 1
• JOZGNYDSEBIJDH-UHFFFAOYSA-N eniluracil Chemical compound O=C1NC=C(C#C)C(=O)N1 JOZGNYDSEBIJDH-UHFFFAOYSA-N 0.000 description 1
• 229950010213 eniluracil Drugs 0.000 description 1
• 229950011487 enocitabine Drugs 0.000 description 1
• 238000007824 enzymatic assay Methods 0.000 description 1
• 238000001952 enzyme assay Methods 0.000 description 1
• 229960002179 ephedrine Drugs 0.000 description 1
• 229960001904 epirubicin Drugs 0.000 description 1
• 229950002973 epitiostanol Drugs 0.000 description 1
• 229930013356 epothilone Natural products 0.000 description 1
• 150000003883 epothilone derivatives Chemical class 0.000 description 1
• 229960001433 erlotinib Drugs 0.000 description 1
• 210000003238 esophagus Anatomy 0.000 description 1
• ITSGNOIFAJAQHJ-BMFNZSJVSA-N esorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)C[C@H](C)O1 ITSGNOIFAJAQHJ-BMFNZSJVSA-N 0.000 description 1
• 229950002017 esorubicin Drugs 0.000 description 1
• 229960001842 estramustine Drugs 0.000 description 1
• FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 description 1
• 229940011871 estrogen Drugs 0.000 description 1
• 239000000262 estrogen Substances 0.000 description 1
• 239000000328 estrogen antagonist Substances 0.000 description 1
• FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
• FGCGWHVDPBOFJE-UHFFFAOYSA-N ethyl 2-cyclobutylideneacetate Chemical compound CCOC(=O)C=C1CCC1 FGCGWHVDPBOFJE-UHFFFAOYSA-N 0.000 description 1
• JSMRUPPAFDYIRD-UHFFFAOYSA-N ethyl 3,3-difluorobutanoate Chemical compound CCOC(=O)CC(C)(F)F JSMRUPPAFDYIRD-UHFFFAOYSA-N 0.000 description 1
• MWGSZQXKIYWSFS-UHFFFAOYSA-N ethyl 4,4,5,5,5-pentafluoro-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)C(F)(F)F MWGSZQXKIYWSFS-UHFFFAOYSA-N 0.000 description 1
• 229960005237 etoglucid Drugs 0.000 description 1
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
• 230000005284 excitation Effects 0.000 description 1
• 230000007717 exclusion Effects 0.000 description 1
• 229960000255 exemestane Drugs 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 229950011548 fadrozole Drugs 0.000 description 1
• 229940043168 fareston Drugs 0.000 description 1
• 229940087861 faslodex Drugs 0.000 description 1
• KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
• 239000012091 fetal bovine serum Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 229960000961 floxuridine Drugs 0.000 description 1
• ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
• 229960000390 fludarabine Drugs 0.000 description 1
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 1
• MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
• 229960002074 flutamide Drugs 0.000 description 1
• 235000019152 folic acid Nutrition 0.000 description 1
• 239000011724 folic acid Substances 0.000 description 1
• 229960000304 folic acid Drugs 0.000 description 1
• 150000002224 folic acids Chemical class 0.000 description 1
• VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 1
• 235000008191 folinic acid Nutrition 0.000 description 1
• 239000011672 folinic acid Substances 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 229960004783 fotemustine Drugs 0.000 description 1
• YAKWPXVTIGTRJH-UHFFFAOYSA-N fotemustine Chemical compound CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O YAKWPXVTIGTRJH-UHFFFAOYSA-N 0.000 description 1
• 229960002258 fulvestrant Drugs 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 108020001507 fusion proteins Proteins 0.000 description 1
• 102000037865 fusion proteins Human genes 0.000 description 1
• 229940044658 gallium nitrate Drugs 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 229960002584 gefitinib Drugs 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 229960005277 gemcitabine Drugs 0.000 description 1
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
• 229940020967 gemzar Drugs 0.000 description 1
• 238000001415 gene therapy Methods 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 229940080856 gleevec Drugs 0.000 description 1
• 229960001731 gluceptate Drugs 0.000 description 1
• KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 229940097042 glucuronate Drugs 0.000 description 1
• 229930182470 glycoside Natural products 0.000 description 1
• 229960002913 goserelin Drugs 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
• 125000001188 haloalkyl group Chemical group 0.000 description 1
• UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 230000036571 hydration Effects 0.000 description 1
• 238000006703 hydration reaction Methods 0.000 description 1
• 150000002429 hydrazines Chemical class 0.000 description 1
• 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 229960001330 hydroxycarbamide Drugs 0.000 description 1
• 229940015872 ibandronate Drugs 0.000 description 1
• 229960000908 idarubicin Drugs 0.000 description 1
• 229960003685 imatinib mesylate Drugs 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
• DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 description 1
• 229950008097 improsulfan Drugs 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 238000003331 infrared imaging Methods 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 230000002452 interceptive effect Effects 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 238000005342 ion exchange Methods 0.000 description 1
• 238000004255 ion exchange chromatography Methods 0.000 description 1
• 229940084651 iressa Drugs 0.000 description 1
• UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
• FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical class CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 108010050180 kallistatin Proteins 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• 229940116871 l-lactate Drugs 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229960004891 lapatinib Drugs 0.000 description 1
• 210000002429 large intestine Anatomy 0.000 description 1
• 210000000867 larynx Anatomy 0.000 description 1
• 229940115286 lentinan Drugs 0.000 description 1
• 229960001691 leucovorin Drugs 0.000 description 1
• GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 1
• 229960004338 leuprorelin Drugs 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 210000000088 lip Anatomy 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• 201000007270 liver cancer Diseases 0.000 description 1
• 229960002247 lomustine Drugs 0.000 description 1
• DHMTURDWPRKSOA-RUZDIDTESA-N lonafarnib Chemical compound C1CN(C(=O)N)CCC1CC(=O)N1CCC([C@@H]2C3=C(Br)C=C(Cl)C=C3CCC3=CC(Br)=CN=C32)CC1 DHMTURDWPRKSOA-RUZDIDTESA-N 0.000 description 1
• YROQEQPFUCPDCP-UHFFFAOYSA-N losoxantrone Chemical compound OCCNCCN1N=C2C3=CC=CC(O)=C3C(=O)C3=C2C1=CC=C3NCCNCCO YROQEQPFUCPDCP-UHFFFAOYSA-N 0.000 description 1
• 229950008745 losoxantrone Drugs 0.000 description 1
• 238000003819 low-pressure liquid chromatography Methods 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 201000005243 lung squamous cell carcinoma Diseases 0.000 description 1
• RVFGKBWWUQOIOU-NDEPHWFRSA-N lurtotecan Chemical compound O=C([C@]1(O)CC)OCC(C(N2CC3=4)=O)=C1C=C2C3=NC1=CC=2OCCOC=2C=C1C=4CN1CCN(C)CC1 RVFGKBWWUQOIOU-NDEPHWFRSA-N 0.000 description 1
• 229950002654 lurtotecan Drugs 0.000 description 1
• 229910001629 magnesium chloride Inorganic materials 0.000 description 1
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical class OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 230000036210 malignancy Effects 0.000 description 1
• 210000004962 mammalian cell Anatomy 0.000 description 1
• 238000007726 management method Methods 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• MQXVYODZCMMZEM-ZYUZMQFOSA-N mannomustine Chemical compound ClCCNC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNCCCl MQXVYODZCMMZEM-ZYUZMQFOSA-N 0.000 description 1
• 229950008612 mannomustine Drugs 0.000 description 1
• WKPWGQKGSOKKOO-RSFHAFMBSA-N maytansine Chemical compound CO[C@@H]([C@@]1(O)C[C@](OC(=O)N1)([C@H]([C@@H]1O[C@@]1(C)[C@@H](OC(=O)[C@H](C)N(C)C(C)=O)CC(=O)N1C)C)[H])\C=C\C=C(C)\CC2=CC(OC)=C(Cl)C1=C2 WKPWGQKGSOKKOO-RSFHAFMBSA-N 0.000 description 1
• 229960004961 mechlorethamine Drugs 0.000 description 1
• HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 1
• 229960004296 megestrol acetate Drugs 0.000 description 1
• 102000006240 membrane receptors Human genes 0.000 description 1
• 229950009246 mepitiostane Drugs 0.000 description 1
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
• QRMNENFZDDYDEF-GOSISDBHSA-N methyl (8s)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-7,8-dihydro-3h-pyrrolo[3,2-e]indole-1-carboxylate Chemical compound C1([C@H](CBr)CN(C1=C1)C(=O)C=2NC3=C(OC)C(OC)=C(OC)C=C3C=2)=C2C(C(=O)OC)=C(C)NC2=C1OC(=O)N1CCN(C)CC1 QRMNENFZDDYDEF-GOSISDBHSA-N 0.000 description 1
• MBAHGFJTIVZLFB-SNAWJCMRSA-N methyl (e)-pent-2-enoate Chemical group CC\C=C\C(=O)OC MBAHGFJTIVZLFB-SNAWJCMRSA-N 0.000 description 1
• IDNCXVFXABLDSK-UHFFFAOYSA-N methyl 1-(trifluoromethyl)cyclobutane-1-carboxylate Chemical compound COC(=O)C1(C(F)(F)F)CCC1 IDNCXVFXABLDSK-UHFFFAOYSA-N 0.000 description 1
• AEZHUDXZHNLVKG-UHFFFAOYSA-N methyl 2-(4-oxocyclohexyl)acetate Chemical compound COC(=O)CC1CCC(=O)CC1 AEZHUDXZHNLVKG-UHFFFAOYSA-N 0.000 description 1
• JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical class COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
• HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
• 230000005012 migration Effects 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 239000008267 milk Substances 0.000 description 1
• 210000004080 milk Anatomy 0.000 description 1
• 235000013336 milk Nutrition 0.000 description 1
• 239000002480 mineral oil Substances 0.000 description 1
• 235000010446 mineral oil Nutrition 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 229960005485 mitobronitol Drugs 0.000 description 1
• 239000003226 mitogen Substances 0.000 description 1
• 229960003539 mitoguazone Drugs 0.000 description 1
• MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 description 1
• VFKZTMPDYBFSTM-GUCUJZIJSA-N mitolactol Chemical compound BrC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-GUCUJZIJSA-N 0.000 description 1
• 229950010913 mitolactol Drugs 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 229960000350 mitotane Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 229960000951 mycophenolic acid Drugs 0.000 description 1
• HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 description 1
• NJSMWLQOCQIOPE-OCHFTUDZSA-N n-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCN=C1N\N=C\C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1\C=N\NC1=NCCN1 NJSMWLQOCQIOPE-OCHFTUDZSA-N 0.000 description 1
• LBWFXVZLPYTWQI-IPOVEDGCSA-N n-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C LBWFXVZLPYTWQI-IPOVEDGCSA-N 0.000 description 1
• 239000002105 nanoparticle Substances 0.000 description 1
• 229950006327 napsilate Drugs 0.000 description 1
• 229930014626 natural product Natural products 0.000 description 1
• 229940086322 navelbine Drugs 0.000 description 1
• 230000001613 neoplastic effect Effects 0.000 description 1
• 208000004296 neuralgia Diseases 0.000 description 1
• 208000021722 neuropathic pain Diseases 0.000 description 1
• 229940080607 nexavar Drugs 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
• 229960002653 nilutamide Drugs 0.000 description 1
• 229960001420 nimustine Drugs 0.000 description 1
• VFEDRRNHLBGPNN-UHFFFAOYSA-N nimustine Chemical compound CC1=NC=C(CNC(=O)N(CCCl)N=O)C(N)=N1 VFEDRRNHLBGPNN-UHFFFAOYSA-N 0.000 description 1
• KGTDRFCXGRULNK-JYOBTZKQSA-N nogalamycin Chemical compound CO[C@@H]1[C@@](OC)(C)[C@@H](OC)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=C4[C@@]5(C)O[C@H]([C@H]([C@@H]([C@H]5O)N(C)C)O)OC4=C3C3=O)=C3C=C2[C@@H](C(=O)OC)[C@@](C)(O)C1 KGTDRFCXGRULNK-JYOBTZKQSA-N 0.000 description 1
• 229950009266 nogalamycin Drugs 0.000 description 1
• 229940085033 nolvadex Drugs 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• 229940127073 nucleoside analogue Drugs 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• CZDBNBLGZNWKMC-MWQNXGTOSA-N olivomycin Chemical class O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1)O[C@H]1O[C@@H](C)[C@H](O)[C@@H](OC2O[C@@H](C)[C@H](O)[C@@H](O)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@H](O)[C@H](OC)[C@H](C)O1 CZDBNBLGZNWKMC-MWQNXGTOSA-N 0.000 description 1
• 229950011093 onapristone Drugs 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical class OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
• 229960001756 oxaliplatin Drugs 0.000 description 1
• AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• 239000003002 pH adjusting agent Substances 0.000 description 1
• 208000027753 pain disease Diseases 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• VREZDOWOLGNDPW-UHFFFAOYSA-N pancratistatine Natural products C1=C2C3C(O)C(O)C(O)C(O)C3NC(=O)C2=C(O)C2=C1OCO2 VREZDOWOLGNDPW-UHFFFAOYSA-N 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 208000030940 penile carcinoma Diseases 0.000 description 1
• 201000008174 penis carcinoma Diseases 0.000 description 1
• 229960002340 pentostatin Drugs 0.000 description 1
• FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 1
• QIMGFXOHTOXMQP-GFAGFCTOSA-N peplomycin 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)NCCCN[C@@H](C)C=1C=CC=CC=1)[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=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C QIMGFXOHTOXMQP-GFAGFCTOSA-N 0.000 description 1
• 229950003180 peplomycin Drugs 0.000 description 1
• 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 239000002304 perfume Substances 0.000 description 1
• 201000002628 peritoneum cancer Diseases 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 229940127557 pharmaceutical product Drugs 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 238000003566 phosphorylation assay Methods 0.000 description 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• 229960000952 pipobroman Drugs 0.000 description 1
• NJBFOOCLYDNZJN-UHFFFAOYSA-N pipobroman Chemical compound BrCCC(=O)N1CCN(C(=O)CCBr)CC1 NJBFOOCLYDNZJN-UHFFFAOYSA-N 0.000 description 1
• NUKCGLDCWQXYOQ-UHFFFAOYSA-N piposulfan Chemical compound CS(=O)(=O)OCCC(=O)N1CCN(C(=O)CCOS(C)(=O)=O)CC1 NUKCGLDCWQXYOQ-UHFFFAOYSA-N 0.000 description 1
• 229950001100 piposulfan Drugs 0.000 description 1
• 229960001221 pirarubicin Drugs 0.000 description 1
• 150000003057 platinum Chemical class 0.000 description 1
• 229920001155 polypropylene Polymers 0.000 description 1
• 230000029279 positive regulation of transcription, DNA-dependent Effects 0.000 description 1
• 235000011181 potassium carbonates Nutrition 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 229960004694 prednimustine Drugs 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
• 229960000624 procarbazine Drugs 0.000 description 1
• 229940087463 proleukin Drugs 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 239000003909 protein kinase inhibitor Substances 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• WOLQREOUPKZMEX-UHFFFAOYSA-N pteroyltriglutamic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)C=C1 WOLQREOUPKZMEX-UHFFFAOYSA-N 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 229950010131 puromycin Drugs 0.000 description 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
• 150000004892 pyridazines Chemical class 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 150000003230 pyrimidines Chemical class 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 229960000948 quinine Drugs 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 229940099538 rapamune Drugs 0.000 description 1
• 108700042226 ras Genes Proteins 0.000 description 1
• BMKDZUISNHGIBY-UHFFFAOYSA-N razoxane Chemical compound C1C(=O)NC(=O)CN1C(C)CN1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-UHFFFAOYSA-N 0.000 description 1
• 229960000460 razoxane Drugs 0.000 description 1
• 230000009257 reactivity Effects 0.000 description 1
• 230000007115 recruitment Effects 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 201000010174 renal carcinoma Diseases 0.000 description 1
• 239000013557 residual solvent Substances 0.000 description 1
• 229930002330 retinoic acid Natural products 0.000 description 1
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
• OWPCHSCAPHNHAV-LMONGJCWSA-N rhizoxin Chemical compound C/C([C@H](OC)[C@@H](C)[C@@H]1C[C@H](O)[C@]2(C)O[C@@H]2/C=C/[C@@H](C)[C@]2([H])OC(=O)C[C@@](C2)(C[C@@H]2O[C@H]2C(=O)O1)[H])=C\C=C\C(\C)=C\C1=COC(C)=N1 OWPCHSCAPHNHAV-LMONGJCWSA-N 0.000 description 1
• 108091092562 ribozyme Proteins 0.000 description 1
• 238000006798 ring closing metathesis reaction Methods 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• MBABCNBNDNGODA-WPZDJQSSSA-N rolliniastatin 1 Natural products O1[C@@H]([C@@H](O)CCCCCCCCCC)CC[C@H]1[C@H]1O[C@@H]([C@H](O)CCCCCCCCCC[C@@H](O)CC=2C(O[C@@H](C)C=2)=O)CC1 MBABCNBNDNGODA-WPZDJQSSSA-N 0.000 description 1
• IMUQLZLGWJSVMV-UOBFQKKOSA-N roridin A Natural products CC(O)C1OCCC(C)C(O)C(=O)OCC2CC(=CC3OC4CC(OC(=O)C=C/C=C/1)C(C)(C23)C45CO5)C IMUQLZLGWJSVMV-UOBFQKKOSA-N 0.000 description 1
• HHJUWIANJFBDHT-ZVTSDNJWSA-N rsa8ko39wh Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 HHJUWIANJFBDHT-ZVTSDNJWSA-N 0.000 description 1
• VHXNKPBCCMUMSW-FQEVSTJZSA-N rubitecan Chemical compound C1=CC([N+]([O-])=O)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VHXNKPBCCMUMSW-FQEVSTJZSA-N 0.000 description 1
• 201000003804 salivary gland carcinoma Diseases 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 208000000587 small cell lung carcinoma Diseases 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000017550 sodium carbonate Nutrition 0.000 description 1
• MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
• 235000019345 sodium thiosulphate Nutrition 0.000 description 1
• 229960003787 sorafenib Drugs 0.000 description 1
• 241000894007 species Species 0.000 description 1
• VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
• 229950006315 spirogermanium Drugs 0.000 description 1
• ICXJVZHDZFXYQC-UHFFFAOYSA-N spongistatin 1 Natural products OC1C(O2)(O)CC(O)C(C)C2CCCC=CC(O2)CC(O)CC2(O2)CC(OC)CC2CC(=O)C(C)C(OC(C)=O)C(C)C(=C)CC(O2)CC(C)(O)CC2(O2)CC(OC(C)=O)CC2CC(=O)OC2C(O)C(CC(=C)CC(O)C=CC(Cl)=C)OC1C2C ICXJVZHDZFXYQC-UHFFFAOYSA-N 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 208000017572 squamous cell neoplasm Diseases 0.000 description 1
• 230000006641 stabilisation Effects 0.000 description 1
• 238000011105 stabilization Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 229960001052 streptozocin Drugs 0.000 description 1
• ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000000859 sublimation Methods 0.000 description 1
• 230000008022 sublimation Effects 0.000 description 1
• 125000000547 substituted alkyl group Chemical group 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical class [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1
• 239000013589 supplement Substances 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 229940034785 sutent Drugs 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 229960001603 tamoxifen Drugs 0.000 description 1
• 229960003454 tamoxifen citrate Drugs 0.000 description 1
• 229940120982 tarceva Drugs 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 238000003419 tautomerization reaction Methods 0.000 description 1
• 229940063683 taxotere Drugs 0.000 description 1
• NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
• 229960001278 teniposide Drugs 0.000 description 1
• DWRCDBHZFVSZIS-UHFFFAOYSA-N tert-butyl 2-[7-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]morpholine-4-carboxylate Chemical compound CN1N=CC=C1NC1=NC(=CC=N1)C1=CC2=NN=C(C3CN(CCO3)C(=O)OC(C)(C)C)N2C=C1 DWRCDBHZFVSZIS-UHFFFAOYSA-N 0.000 description 1
• CTVHINDANRPFIL-UHFFFAOYSA-N tert-butyl 3-formylpiperidine-1-carboxylate Chemical group CC(C)(C)OC(=O)N1CCCC(C=O)C1 CTVHINDANRPFIL-UHFFFAOYSA-N 0.000 description 1
• 210000001550 testis Anatomy 0.000 description 1
• BPEWUONYVDABNZ-DZBHQSCQSA-N testolactone Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(OC(=O)CC4)[C@@H]4[C@@H]3CCC2=C1 BPEWUONYVDABNZ-DZBHQSCQSA-N 0.000 description 1
• 229960005353 testolactone Drugs 0.000 description 1
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 125000004525 thiadiazinyl group Chemical group S1NN=C(C=C1)* 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
• 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
• 210000001685 thyroid gland Anatomy 0.000 description 1
• YFTWHEBLORWGNI-UHFFFAOYSA-N tiamiprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC(N)=NC2=C1NC=N2 YFTWHEBLORWGNI-UHFFFAOYSA-N 0.000 description 1
• 229950011457 tiamiprine Drugs 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 210000002105 tongue Anatomy 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
• 229960000303 topotecan Drugs 0.000 description 1
• UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 229950001353 tretamine Drugs 0.000 description 1
• IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
• 229960001727 tretinoin Drugs 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• PXSOHRWMIRDKMP-UHFFFAOYSA-N triaziquone Chemical compound O=C1C(N2CC2)=C(N2CC2)C(=O)C=C1N1CC1 PXSOHRWMIRDKMP-UHFFFAOYSA-N 0.000 description 1
• 229960004560 triaziquone Drugs 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 229930013292 trichothecene Natural products 0.000 description 1
• 150000003327 trichothecene derivatives Chemical class 0.000 description 1
• GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• KVJXBPDAXMEYOA-CXANFOAXSA-N trilostane Chemical compound OC1=C(C#N)C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@@]32O[C@@H]31 KVJXBPDAXMEYOA-CXANFOAXSA-N 0.000 description 1
• 229960001670 trilostane Drugs 0.000 description 1
• NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
• 229960001099 trimetrexate Drugs 0.000 description 1
• NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
• 229960000875 trofosfamide Drugs 0.000 description 1
• UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 1
• 229950010147 troxacitabine Drugs 0.000 description 1
• RXRGZNYSEHTMHC-BQBZGAKWSA-N troxacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)OC1 RXRGZNYSEHTMHC-BQBZGAKWSA-N 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• 230000005751 tumor progression Effects 0.000 description 1
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
• 229940094060 tykerb Drugs 0.000 description 1
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
• 229950009811 ubenimex Drugs 0.000 description 1
• 238000011144 upstream manufacturing Methods 0.000 description 1
• 229960001055 uracil mustard Drugs 0.000 description 1
• 208000010570 urinary bladder carcinoma Diseases 0.000 description 1
• 206010046766 uterine cancer Diseases 0.000 description 1
• 208000012991 uterine carcinoma Diseases 0.000 description 1
• 229950000578 vatalanib Drugs 0.000 description 1
• YCOYDOIWSSHVCK-UHFFFAOYSA-N vatalanib Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 YCOYDOIWSSHVCK-UHFFFAOYSA-N 0.000 description 1
• 229940099039 velcade Drugs 0.000 description 1
• 229960003048 vinblastine Drugs 0.000 description 1
• JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
• 229960004528 vincristine Drugs 0.000 description 1
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
• GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 1
• 229960002066 vinorelbine Drugs 0.000 description 1
• CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
• 229960001771 vorozole Drugs 0.000 description 1
• XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
• 201000005102 vulva cancer Diseases 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 239000011995 wilkinson's catalyst Substances 0.000 description 1
• UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
• 229940053867 xeloda Drugs 0.000 description 1
• 229950009268 zinostatin Drugs 0.000 description 1
• FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
• 229960000641 zorubicin Drugs 0.000 description 1