TWI840343B - AhR調節劑 - Google Patents

Info

Publication number

TWI840343B

TWI840343B TW108104425A TW108104425A TWI840343B TW I840343 B TWI840343 B TW I840343B TW 108104425 A TW108104425 A TW 108104425A TW 108104425 A TW108104425 A TW 108104425A TW I840343 B TWI840343 B TW I840343B

Authority

TW

Taiwan

Prior art keywords

methyl

trifluoromethyl

phenyl

quinazolin

dihydropyrazolo

Prior art date

2018-02-06

Links

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• 150000001875 compounds Chemical class 0.000 claims abstract description 406
• 239000000203 mixture Substances 0.000 claims abstract description 180
• -1 cyano, methyl Chemical group 0.000 claims description 242
• 125000000217 alkyl group Chemical group 0.000 claims description 98
• 229910052739 hydrogen Inorganic materials 0.000 claims description 76
• 150000003839 salts Chemical class 0.000 claims description 52
• 229910052736 halogen Inorganic materials 0.000 claims description 47
• 150000002367 halogens Chemical class 0.000 claims description 47
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 39
• 239000003795 chemical substances by application Substances 0.000 claims description 39
• 229910052805 deuterium Inorganic materials 0.000 claims description 39
• 206010028980 Neoplasm Diseases 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 33
• 239000000460 chlorine Substances 0.000 claims description 30
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 28
• 239000012453 solvate Substances 0.000 claims description 25
• 239000003814 drug Substances 0.000 claims description 24
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
• 150000002431 hydrogen Chemical class 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 238000009472 formulation Methods 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 201000011510 cancer Diseases 0.000 claims description 14
• 239000011737 fluorine Substances 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000003282 alkyl amino group Chemical group 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 125000004122 cyclic group Chemical group 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• KWHPWBXOLZTZMJ-UHFFFAOYSA-N 4-ethylpiperidine Chemical compound CCC1CCNCC1 KWHPWBXOLZTZMJ-UHFFFAOYSA-N 0.000 claims description 5
• DBNFGZAIYRBSIE-UHFFFAOYSA-N 4-methylpiperidin-3-one Chemical compound CC1CCNCC1=O DBNFGZAIYRBSIE-UHFFFAOYSA-N 0.000 claims description 5
• UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 5
• 125000001931 aliphatic group Chemical group 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 125000002843 carboxylic acid group Chemical group 0.000 claims description 5
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 201000005202 lung cancer Diseases 0.000 claims description 4
• 208000020816 lung neoplasm Diseases 0.000 claims description 4
• OYBNNAHIBWBZDW-UHFFFAOYSA-N 1-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4H-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CN1N=CC2=C1C(N(C2)C1=C(C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)C)=O OYBNNAHIBWBZDW-UHFFFAOYSA-N 0.000 claims description 3
• PUTWQCNJUYXTIW-UHFFFAOYSA-N 1-methyl-6-[2-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound CN1N=CC2=C1C(=O)N(CC2)C1=C(C)C=C(C=C1)C1=NC=C2N=C(C=CC2=N1)C(F)(F)F PUTWQCNJUYXTIW-UHFFFAOYSA-N 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
• WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• FKTPQGMKXGVOHC-UHFFFAOYSA-N 1-methyl-6-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound CN1N=CC2=C1C(=O)N(CC2)C1=C(C)C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F FKTPQGMKXGVOHC-UHFFFAOYSA-N 0.000 claims description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 208000034578 Multiple myelomas Diseases 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
• 201000002528 pancreatic cancer Diseases 0.000 claims description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
• XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
• 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims 2
• IAQSHBSXGJBPFR-UHFFFAOYSA-N 6,7-dihydropyrazolo[1,5-a]pyridine Chemical compound C1=CCCN2N=CC=C21 IAQSHBSXGJBPFR-UHFFFAOYSA-N 0.000 claims 1
• AFYJLKIXCUBJHD-UHFFFAOYSA-N 8-methyl-2-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-3,4-dihydropyrazolo[1,5-e][1,2,5]thiadiazine 1,1-dioxide Chemical compound CC=1C=NN2CCN(S(C2=1)(=O)=O)C1=C(C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)C AFYJLKIXCUBJHD-UHFFFAOYSA-N 0.000 claims 1
• 238000011319 anticancer therapy Methods 0.000 claims 1
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 73
• 201000010099 disease Diseases 0.000 abstract description 31
• 238000011282 treatment Methods 0.000 abstract description 30
• 238000000034 method Methods 0.000 abstract description 25
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 500
• 230000015572 biosynthetic process Effects 0.000 description 241
• 238000003786 synthesis reaction Methods 0.000 description 240
• 239000000243 solution Substances 0.000 description 223
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 206
• 239000007787 solid Substances 0.000 description 202
• 235000019439 ethyl acetate Nutrition 0.000 description 194
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 179
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 155
• 239000012299 nitrogen atmosphere Substances 0.000 description 123
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 116
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 112
• 239000012044 organic layer Substances 0.000 description 93
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
• 230000002829 reductive effect Effects 0.000 description 75
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 70
• 239000012043 crude product Substances 0.000 description 62
• 239000003208 petroleum Substances 0.000 description 56
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 52
• 238000005160 1H NMR spectroscopy Methods 0.000 description 51
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
• 239000000741 silica gel Substances 0.000 description 51
• 229910002027 silica gel Inorganic materials 0.000 description 51
• 238000010898 silica gel chromatography Methods 0.000 description 49
• 239000004698 Polyethylene Substances 0.000 description 46
• 239000011541 reaction mixture Substances 0.000 description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 43
• 208000035475 disorder Diseases 0.000 description 42
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• 238000006243 chemical reaction Methods 0.000 description 36
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• 239000003480 eluent Substances 0.000 description 34
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
• 230000000694 effects Effects 0.000 description 27
• 235000002639 sodium chloride Nutrition 0.000 description 27
• 239000010410 layer Substances 0.000 description 26
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• 239000002253 acid Substances 0.000 description 20
• 238000001953 recrystallisation Methods 0.000 description 20
• 238000012746 preparative thin layer chromatography Methods 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 17
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
• 238000000746 purification Methods 0.000 description 17
• 230000001225 therapeutic effect Effects 0.000 description 17
• 238000001914 filtration Methods 0.000 description 16
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 16
• 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 16
• 239000011734 sodium Substances 0.000 description 15
• 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 14
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 13
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• 235000019270 ammonium chloride Nutrition 0.000 description 13
• 210000004027 cell Anatomy 0.000 description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• 239000003112 inhibitor Substances 0.000 description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
• 239000012258 stirred mixture Substances 0.000 description 12
• XGKICHJOVNGJBU-UHFFFAOYSA-N 2-chloro-6-(trifluoromethyl)quinazoline Chemical compound ClC1=NC2=CC=C(C=C2C=N1)C(F)(F)F XGKICHJOVNGJBU-UHFFFAOYSA-N 0.000 description 11
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 11
• NWRQIAGXUQATEC-UHFFFAOYSA-N 2-chloro-6-(trifluoromethyl)pyrido[3,2-d]pyrimidine Chemical compound FC(F)(F)c1ccc2nc(Cl)ncc2n1 NWRQIAGXUQATEC-UHFFFAOYSA-N 0.000 description 10
• PCHYYOCUCGCSBU-UHFFFAOYSA-N 4-bromo-2-methylaniline Chemical compound CC1=CC(Br)=CC=C1N PCHYYOCUCGCSBU-UHFFFAOYSA-N 0.000 description 10
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
• 229930040373 Paraformaldehyde Natural products 0.000 description 10
• 229940079593 drug Drugs 0.000 description 10
• 239000003446 ligand Substances 0.000 description 10
• 229920002866 paraformaldehyde Polymers 0.000 description 10
• 229910052717 sulfur Inorganic materials 0.000 description 10
• 229940124597 therapeutic agent Drugs 0.000 description 10
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 239000013543 active substance Substances 0.000 description 9
• 239000000556 agonist Substances 0.000 description 9
• 238000002648 combination therapy Methods 0.000 description 9
• 230000007246 mechanism Effects 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 8
• 239000000427 antigen Substances 0.000 description 8
• 108091007433 antigens Proteins 0.000 description 8
• 102000036639 antigens Human genes 0.000 description 8
• 239000003085 diluting agent Substances 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 108090000623 proteins and genes Proteins 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• 208000024891 symptom Diseases 0.000 description 8
• 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 description 7
• IQTOSYIKAKCIBO-UHFFFAOYSA-N 4-methyl-2-(2-phenylmethoxyethyl)pyrazole-3-carboxylic acid Chemical compound C(C1=CC=CC=C1)OCCN1N=CC(=C1C(=O)O)C IQTOSYIKAKCIBO-UHFFFAOYSA-N 0.000 description 7
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
• 230000004913 activation Effects 0.000 description 7
• 230000002401 inhibitory effect Effects 0.000 description 7
• 239000007924 injection Substances 0.000 description 7
• 238000002347 injection Methods 0.000 description 7
• 239000000546 pharmaceutical excipient Substances 0.000 description 7
• 230000003449 preventive effect Effects 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• 125000001424 substituent group Chemical group 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• NCOWBQRCCMJSKW-UHFFFAOYSA-N 2-bromo-6-(trifluoromethyl)pyridin-3-amine Chemical compound NC1=CC=C(C(F)(F)F)N=C1Br NCOWBQRCCMJSKW-UHFFFAOYSA-N 0.000 description 6
• CUZKCNWZBXLAJX-UHFFFAOYSA-N 2-phenylmethoxyethanol Chemical compound OCCOCC1=CC=CC=C1 CUZKCNWZBXLAJX-UHFFFAOYSA-N 0.000 description 6
• 229910015844 BCl3 Inorganic materials 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• 239000007821 HATU Substances 0.000 description 6
• 239000007832 Na2SO4 Substances 0.000 description 6
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• 239000003242 anti bacterial agent Substances 0.000 description 6
• 125000003118 aryl group Chemical group 0.000 description 6
• 230000001580 bacterial effect Effects 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 238000011161 development Methods 0.000 description 6
• 230000018109 developmental process Effects 0.000 description 6
• 239000000032 diagnostic agent Substances 0.000 description 6
• 229940039227 diagnostic agent Drugs 0.000 description 6
• ODRGOJOJIWIZTC-UHFFFAOYSA-N ethyl 4-methyl-2-(2-phenylmethoxyethyl)pyrazole-3-carboxylate Chemical compound C1(=C(C=NN1CCOCC1=CC=CC=C1)C)C(=O)OCC ODRGOJOJIWIZTC-UHFFFAOYSA-N 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 229940002612 prodrug Drugs 0.000 description 6
• 239000000651 prodrug Substances 0.000 description 6
• 239000000376 reactant Substances 0.000 description 6
• 102000005962 receptors Human genes 0.000 description 6
• 108020003175 receptors Proteins 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910052938 sodium sulfate Inorganic materials 0.000 description 6
• 235000011152 sodium sulphate Nutrition 0.000 description 6
• FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 6
• 230000003612 virological effect Effects 0.000 description 6
• QJSVGSVTONZEPX-UHFFFAOYSA-N 1-methyl-6-[2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound CN1N=CC2=C1C(=O)N(CC2)C1=C(C)C=C(C=C1)B1OC(C)(C)C(C)(C)O1 QJSVGSVTONZEPX-UHFFFAOYSA-N 0.000 description 5
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 5
• 102000037982 Immune checkpoint proteins Human genes 0.000 description 5
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