TWI706954B - 用於治療及預防病毒感染之新穎磺醯亞胺醯基嘌呤酮化合物及衍生物 - Google Patents

Info

Publication number

TWI706954B

TWI706954B TW105114192A TW105114192A TWI706954B TW I706954 B TWI706954 B TW I706954B TW 105114192 A TW105114192 A TW 105114192A TW 105114192 A TW105114192 A TW 105114192A TW I706954 B TWI706954 B TW I706954B

Authority

TW

Taiwan

Prior art keywords

methyl

purin

compound

amino

chloro

Prior art date

2015-05-08

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 746
• 238000011282 treatment Methods 0.000 title claims description 32
• 230000009385 viral infection Effects 0.000 title description 5
• 238000011321 prophylaxis Methods 0.000 title 1
• 150000003839 salts Chemical class 0.000 claims abstract description 78
• 238000000034 method Methods 0.000 claims abstract description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 382
• 238000002360 preparation method Methods 0.000 claims description 358
• -1 cyano, carboxy, carbamoyl Chemical group 0.000 claims description 286
• 125000000217 alkyl group Chemical group 0.000 claims description 116
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 94
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 63
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 33
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 239000003814 drug Substances 0.000 claims description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 18
• 229940079593 drug Drugs 0.000 claims description 18
• 125000004803 chlorobenzyl group Chemical group 0.000 claims description 17
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
• 125000006178 methyl benzyl group Chemical group 0.000 claims description 15
• 125000004076 pyridyl group Chemical group 0.000 claims description 15
• 239000003153 chemical reaction reagent Substances 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical group 0.000 claims description 14
• 229940044616 toll-like receptor 7 agonist Drugs 0.000 claims description 14
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 11
• 125000004175 fluorobenzyl group Chemical group 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 9
• 239000005711 Benzoic acid Substances 0.000 claims description 8
• 235000010233 benzoic acid Nutrition 0.000 claims description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 125000006287 difluorobenzyl group Chemical group 0.000 claims description 8
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
• QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 7
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
• 125000002946 cyanobenzyl group Chemical group 0.000 claims description 7
• 208000002672 hepatitis B Diseases 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000007800 oxidant agent Substances 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
• 102000006992 Interferon-alpha Human genes 0.000 claims description 6
• 108010047761 Interferon-alpha Proteins 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
• OMAUXCABUFLOCJ-UHFFFAOYSA-N CCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1Cl)C2=O)(=O)=O Chemical compound CCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1Cl)C2=O)(=O)=O OMAUXCABUFLOCJ-UHFFFAOYSA-N 0.000 claims description 5
• HKWOCPGCOHYWRT-UHFFFAOYSA-N CCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=C(C)C=C1)C2=O)(=O)=O Chemical compound CCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=C(C)C=C1)C2=O)(=O)=O HKWOCPGCOHYWRT-UHFFFAOYSA-N 0.000 claims description 5
• KFQUHIIWGIWPOP-UHFFFAOYSA-N COC1=CC=C(CN(C(C(N2)=C(N)N3)=NC3=NS(C)(=O)=O)C2=O)C=C1 Chemical compound COC1=CC=C(CN(C(C(N2)=C(N)N3)=NC3=NS(C)(=O)=O)C2=O)C=C1 KFQUHIIWGIWPOP-UHFFFAOYSA-N 0.000 claims description 5
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
• SAAQOQMUURDFIZ-UHFFFAOYSA-N CCCCS(NC(N=C1N2CC3=CC=CC=C3)=NC(N)=C1NC2=O)(=O)=O Chemical compound CCCCS(NC(N=C1N2CC3=CC=CC=C3)=NC(N)=C1NC2=O)(=O)=O SAAQOQMUURDFIZ-UHFFFAOYSA-N 0.000 claims description 4
• USDAXYCRTFKRMN-UHFFFAOYSA-N CCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=CC=C1)C2=O)(=O)=O Chemical compound CCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=CC=C1)C2=O)(=O)=O USDAXYCRTFKRMN-UHFFFAOYSA-N 0.000 claims description 4
• WOCWUWJTOMJERY-UHFFFAOYSA-N COC1=CC=C(CN(C(C(N2)=C(N)N3)=NC3=NS(CCCCl)(=O)=O)C2=O)C=C1 Chemical compound COC1=CC=C(CN(C(C(N2)=C(N)N3)=NC3=NS(CCCCl)(=O)=O)C2=O)C=C1 WOCWUWJTOMJERY-UHFFFAOYSA-N 0.000 claims description 4
• CONDEISNZPIQNI-UHFFFAOYSA-N CS(N=C(NC(N)=C1N2)N=C1N(CC1=NC=CC=C1)C2=O)(=O)=O Chemical compound CS(N=C(NC(N)=C1N2)N=C1N(CC1=NC=CC=C1)C2=O)(=O)=O CONDEISNZPIQNI-UHFFFAOYSA-N 0.000 claims description 4
• 125000006278 bromobenzyl group Chemical group 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• NKZGJZSQVAVNTQ-UHFFFAOYSA-N CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1Br)C2=O)(=O)=O Chemical compound CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1Br)C2=O)(=O)=O NKZGJZSQVAVNTQ-UHFFFAOYSA-N 0.000 claims description 3
• JTJJZZICOOTZGF-UHFFFAOYSA-N CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=N1)=CC=C1Cl)C2=O)(=O)=O Chemical compound CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=N1)=CC=C1Cl)C2=O)(=O)=O JTJJZZICOOTZGF-UHFFFAOYSA-N 0.000 claims description 3
• COIZLMXJRCNWHS-UHFFFAOYSA-N CS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=NC=C1)C2=O)(=O)=O Chemical compound CS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=NC=C1)C2=O)(=O)=O COIZLMXJRCNWHS-UHFFFAOYSA-N 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
• RIPRLDHCXFAHPT-UHFFFAOYSA-N NC(NC(N=C1N2CC3=CC=CC=C3)=NS(CC(F)(F)F)(=O)=O)=C1NC2=O Chemical compound NC(NC(N=C1N2CC3=CC=CC=C3)=NS(CC(F)(F)F)(=O)=O)=C1NC2=O RIPRLDHCXFAHPT-UHFFFAOYSA-N 0.000 claims description 3
• OTVYYLXWWFQZBY-UHFFFAOYSA-N NC(NC(N=C1N2CC3=CC=CC=C3)=NS(CC3CCCCC3)(=O)=O)=C1NC2=O Chemical compound NC(NC(N=C1N2CC3=CC=CC=C3)=NS(CC3CCCCC3)(=O)=O)=C1NC2=O OTVYYLXWWFQZBY-UHFFFAOYSA-N 0.000 claims description 3
• NTIBNBAEYFDWFP-UHFFFAOYSA-N NC1=C2NC(N(C2=NC(N1)=NS(=O)(=O)C)CC1=CC=C(C=C1)Cl)=O Chemical compound NC1=C2NC(N(C2=NC(N1)=NS(=O)(=O)C)CC1=CC=C(C=C1)Cl)=O NTIBNBAEYFDWFP-UHFFFAOYSA-N 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
• 125000006286 dichlorobenzyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 3
• YXBYASVJXXHYQN-UHFFFAOYSA-N CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1Cl)C2=O)(=O)=O Chemical compound CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1Cl)C2=O)(=O)=O YXBYASVJXXHYQN-UHFFFAOYSA-N 0.000 claims description 2
• UWDZFZMUBYBTAQ-UHFFFAOYSA-N CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1F)C2=O)(=O)=O Chemical compound CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1F)C2=O)(=O)=O UWDZFZMUBYBTAQ-UHFFFAOYSA-N 0.000 claims description 2
• 239000013543 active substance Substances 0.000 claims description 2
• 229940095102 methyl benzoate Drugs 0.000 claims description 2
• 108091027076 Spiegelmer Proteins 0.000 claims 2
• WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 claims 2
• HIUWJHBGMPYSMC-UHFFFAOYSA-N CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=CC=C1)=C1Cl)C2=O)(=O)=O Chemical compound CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=CC=C1)=C1Cl)C2=O)(=O)=O HIUWJHBGMPYSMC-UHFFFAOYSA-N 0.000 claims 1
• RGGVRTIZCYJQNU-UHFFFAOYSA-N COC1=CC=C(CN(C(C(N2)=C(N)N3)=NC3=NS(CCCN3CCCC3)(=O)=O)C2=O)C=C1 Chemical compound COC1=CC=C(CN(C(C(N2)=C(N)N3)=NC3=NS(CCCN3CCCC3)(=O)=O)C2=O)C=C1 RGGVRTIZCYJQNU-UHFFFAOYSA-N 0.000 claims 1
• POASRAGTZKKJOL-UHFFFAOYSA-N COCCCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=CC=C1)C2=O)(=O)=O Chemical compound COCCCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=CC=C1)C2=O)(=O)=O POASRAGTZKKJOL-UHFFFAOYSA-N 0.000 claims 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 48
• 239000000651 prodrug Substances 0.000 abstract description 24
• 229940002612 prodrug Drugs 0.000 abstract description 24
• 238000004949 mass spectrometry Methods 0.000 description 320
• 239000007787 solid Substances 0.000 description 286
• 238000005481 NMR spectroscopy Methods 0.000 description 101
• 125000002252 acyl group Chemical group 0.000 description 100
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 58
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 52
• 239000000243 solution Substances 0.000 description 52
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
• WPYNEOHJXNKMSR-UHFFFAOYSA-N 9-[(2-chlorophenyl)methyl]-6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C(C=CC=C1)CN1C2=NC(=NC(=C2NC1=O)NCC1=CC=C(C=C1)OC)SCCC WPYNEOHJXNKMSR-UHFFFAOYSA-N 0.000 description 34
• 239000011541 reaction mixture Substances 0.000 description 34
• 210000004027 cell Anatomy 0.000 description 29
• RYWCQJDEHXJHRI-XJMXIVSISA-N 2-[3-[5-[6-[3-[3-(carboxymethyl)phenyl]-4-[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]hexyl]-2-[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]acetic acid Chemical compound O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC(C(=C1)C=2C=C(CC(O)=O)C=CC=2)=CC=C1CCCCCCC(C=C1C=2C=C(CC(O)=O)C=CC=2)=CC=C1O[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 RYWCQJDEHXJHRI-XJMXIVSISA-N 0.000 description 27
• ZNSPHKJFQDEABI-NZQKXSOJSA-N Nc1nc(O[C@H](c2ccc(Cl)cc2-c2ccccc2)C(F)(F)F)cc(n1)N1CCC2(CN[C@@H](C2)C(O)=O)CC1 Chemical compound Nc1nc(O[C@H](c2ccc(Cl)cc2-c2ccccc2)C(F)(F)F)cc(n1)N1CCC2(CN[C@@H](C2)C(O)=O)CC1 ZNSPHKJFQDEABI-NZQKXSOJSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 229940125876 compound 15a Drugs 0.000 description 27
• TZSZZENYCISATO-WIOPSUGQSA-N rodatristat Chemical compound CCOC(=O)[C@@H]1CC2(CN1)CCN(CC2)c1cc(O[C@H](c2ccc(Cl)cc2-c2ccccc2)C(F)(F)F)nc(N)n1 TZSZZENYCISATO-WIOPSUGQSA-N 0.000 description 27
• KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 26
• XTZYFTXASKYXGM-UHFFFAOYSA-N 6-chloro-N-[(2-chlorophenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=C(C=CC=C1)Cl)[N+](=O)[O-] XTZYFTXASKYXGM-UHFFFAOYSA-N 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
• 238000010828 elution Methods 0.000 description 25
• DVWOYOSIEJRHKW-UIRZNSHLSA-M sodium (2S)-2-[[(2S)-2-[[(4,4-difluorocyclohexyl)-phenylmethoxy]carbonylamino]-4-methylpentanoyl]amino]-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propane-1-sulfonate Chemical compound FC1(CCC(CC1)C(OC(=O)N[C@H](C(=O)N[C@H](C(S(=O)(=O)[O-])O)C[C@H]1C(NCC1)=O)CC(C)C)C1=CC=CC=C1)F.[Na+] DVWOYOSIEJRHKW-UIRZNSHLSA-M 0.000 description 25
• 235000019439 ethyl acetate Nutrition 0.000 description 24
• RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 23
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
• 238000004458 analytical method Methods 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• 238000012360 testing method Methods 0.000 description 18
• PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 17
• HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 17
• SRMFHHGQKBMKFJ-UHFFFAOYSA-N 6-chloro-4-N-[(2-chlorophenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=C(C=CC=C1)Cl)N SRMFHHGQKBMKFJ-UHFFFAOYSA-N 0.000 description 17
• 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 description 17
• 238000004128 high performance liquid chromatography Methods 0.000 description 16
• 230000006698 induction Effects 0.000 description 16
• 239000012044 organic layer Substances 0.000 description 16
• 229940100389 Sulfonylurea Drugs 0.000 description 15
• 102100039390 Toll-like receptor 7 Human genes 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 14
• 239000002253 acid Substances 0.000 description 14
• CMYNXPLOCPEGOY-UHFFFAOYSA-N 9-benzyl-6-chloro-2-propylsulfanyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)Cl)SCCC CMYNXPLOCPEGOY-UHFFFAOYSA-N 0.000 description 13
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 13
• 229910052739 hydrogen Inorganic materials 0.000 description 13
• 238000000746 purification Methods 0.000 description 13
• 229960001930 valpromide Drugs 0.000 description 13
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 12
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
• 239000000523 sample Substances 0.000 description 12
• 238000000926 separation method Methods 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 229960003180 glutathione Drugs 0.000 description 11
• 150000002576 ketones Chemical class 0.000 description 11
• BOUNFBOFBGBYBT-UHFFFAOYSA-N purin-8-one Chemical compound C1=NC=NC2=NC(=O)N=C21 BOUNFBOFBGBYBT-UHFFFAOYSA-N 0.000 description 11
• WFSSNYXARPONJV-UHFFFAOYSA-N 6-aminopurin-8-one Chemical compound NC1=NC=NC2=NC(=O)N=C12 WFSSNYXARPONJV-UHFFFAOYSA-N 0.000 description 10
• 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 description 10
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
• 150000002500 ions Chemical class 0.000 description 10
• 150000004702 methyl esters Chemical class 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 10
• HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• 239000012267 brine Substances 0.000 description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 230000002503 metabolic effect Effects 0.000 description 9
• 229960004448 pentamidine Drugs 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• 125000004543 purin-7-yl group Chemical group N1=CN=C2N=CN(C2=C1)* 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 102000003945 NF-kappa B Human genes 0.000 description 8
• 108010057466 NF-kappa B Proteins 0.000 description 8
• 102100033110 Toll-like receptor 8 Human genes 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 239000002609 medium Substances 0.000 description 8
• 238000002953 preparative HPLC Methods 0.000 description 8
• 238000002560 therapeutic procedure Methods 0.000 description 8
• RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 7
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 7
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
• JHNLZOVBAQWGQU-UHFFFAOYSA-N 380814_sial Chemical compound CS(O)(=O)=O.O=P(=O)OP(=O)=O JHNLZOVBAQWGQU-UHFFFAOYSA-N 0.000 description 7
• SAZGJPXEDWRWQT-UHFFFAOYSA-N 4-amino-3-[(4-chlorophenyl)methyl]-2-oxo-1H-imidazole-5-carbonitrile Chemical compound NC=1N(C(NC=1C#N)=O)CC1=CC=C(C=C1)Cl SAZGJPXEDWRWQT-UHFFFAOYSA-N 0.000 description 7
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 7
• XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 7
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
• 239000000411 inducer Substances 0.000 description 7
• 238000001990 intravenous administration Methods 0.000 description 7
• 210000001853 liver microsome Anatomy 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
• VFOKSTCIRGDTBR-UHFFFAOYSA-N 4-amino-2-butoxy-8-[[3-(pyrrolidin-1-ylmethyl)phenyl]methyl]-5,7-dihydropteridin-6-one Chemical compound C12=NC(OCCCC)=NC(N)=C2NC(=O)CN1CC(C=1)=CC=CC=1CN1CCCC1 VFOKSTCIRGDTBR-UHFFFAOYSA-N 0.000 description 6
• 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 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 235000011054 acetic acid Nutrition 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 230000001684 chronic effect Effects 0.000 description 6
• 238000004440 column chromatography Methods 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 235000019253 formic acid Nutrition 0.000 description 6
• 230000001965 increasing effect Effects 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• PFGVNLZDWRZPJW-OPAMFIHVSA-N otamixaban Chemical compound C([C@@H](C(=O)OC)[C@@H](C)NC(=O)C=1C=CC(=CC=1)C=1C=C[N+]([O-])=CC=1)C1=CC=CC(C(N)=N)=C1 PFGVNLZDWRZPJW-OPAMFIHVSA-N 0.000 description 6
• XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 6
• DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 6
• 239000000546 pharmaceutical excipient Substances 0.000 description 6
• 102000005962 receptors Human genes 0.000 description 6
• 108020003175 receptors Proteins 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 6
• JQSHBVHOMNKWFT-DTORHVGOSA-N varenicline Chemical compound C12=CC3=NC=CN=C3C=C2[C@H]2C[C@@H]1CNC2 JQSHBVHOMNKWFT-DTORHVGOSA-N 0.000 description 6
• 229950003036 vesatolimod Drugs 0.000 description 6
• YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 5
• DDEDQHVHVPJFAC-UHFFFAOYSA-N 4,6-dichloro-5-nitro-2-propylsulfanylpyrimidine Chemical compound CCCSC1=NC(Cl)=C([N+]([O-])=O)C(Cl)=N1 DDEDQHVHVPJFAC-UHFFFAOYSA-N 0.000 description 5
• LBJHPOUSJLRRIE-UHFFFAOYSA-N 4-[(6-amino-8-oxo-2-propylsulfanyl-7H-purin-9-yl)methyl]benzonitrile Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C#N)C=C1)=O LBJHPOUSJLRRIE-UHFFFAOYSA-N 0.000 description 5
• UJMGBGIFVTZJHH-UHFFFAOYSA-N 6-amino-9-benzyl-2-methylsulfanyl-7h-purin-8-one Chemical compound C12=NC(SC)=NC(N)=C2N=C(O)N1CC1=CC=CC=C1 UJMGBGIFVTZJHH-UHFFFAOYSA-N 0.000 description 5
• 108091006146 Channels Proteins 0.000 description 5
• 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 5
• 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 5
• 241000711549 Hepacivirus C Species 0.000 description 5
• 102000002689 Toll-like receptor Human genes 0.000 description 5
• 108020000411 Toll-like receptor Proteins 0.000 description 5
• 230000004913 activation Effects 0.000 description 5
• 230000001270 agonistic effect Effects 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 239000007789 gas Substances 0.000 description 5
• 208000010710 hepatitis C virus infection Diseases 0.000 description 5
• 239000001257 hydrogen Substances 0.000 description 5
• 210000004185 liver Anatomy 0.000 description 5
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
• IRHUOBBBQIWSET-UHFFFAOYSA-N methyl 4-[(6-amino-8-oxo-2-propylsulfinyl-7H-purin-9-yl)methyl]benzoate Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=CC=C(C(=O)OC)C=C1)=O IRHUOBBBQIWSET-UHFFFAOYSA-N 0.000 description 5
• OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 5
• 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 5
• 229910000342 sodium bisulfate Inorganic materials 0.000 description 5
• 239000011550 stock solution Substances 0.000 description 5
• ASQOQJYHIYYTEJ-GBESFXJTSA-N (1r,7s,9as)-7-decyl-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-ol Chemical compound O[C@@H]1CCCN2C[C@@H](CCCCCCCCCC)CC[C@H]21 ASQOQJYHIYYTEJ-GBESFXJTSA-N 0.000 description 4
• NZPFQOXRHLUPRT-UHFFFAOYSA-N (6-methylpyridin-3-yl)methanamine Chemical compound CC1=CC=C(CN)C=N1 NZPFQOXRHLUPRT-UHFFFAOYSA-N 0.000 description 4
• DPRJPRMZJGWLHY-HNGSOEQISA-N (e,3r,5s)-7-[5-(4-fluorophenyl)-3-propan-2-yl-1-pyrazin-2-ylpyrazol-4-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)/C=C/C=1C(C(C)C)=NN(C=2N=CC=NC=2)C=1C1=CC=C(F)C=C1 DPRJPRMZJGWLHY-HNGSOEQISA-N 0.000 description 4
• 108091032973 (ribonucleotides)n+m Proteins 0.000 description 4
• GYIUDLLQLVWKPP-UHFFFAOYSA-N 2-propylpentanoyl 2-propylpentanoate Chemical compound CCCC(CCC)C(=O)OC(=O)C(CCC)CCC GYIUDLLQLVWKPP-UHFFFAOYSA-N 0.000 description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 4
• WRLVSFOJEGDHND-UHFFFAOYSA-N 4-[(2-chlorophenyl)methyl]-2-propylsulfanyl-1H-pyrimidine-4,5-diamine Chemical compound ClC1=C(C=CC=C1)CC1(NC(=NC=C1N)SCCC)N WRLVSFOJEGDHND-UHFFFAOYSA-N 0.000 description 4
• CBMWXHQXHJQKDE-UHFFFAOYSA-N 4-[(6-amino-8-oxo-2-propylsulfinyl-7H-purin-9-yl)methyl]benzonitrile Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=CC=C(C#N)C=C1)=O CBMWXHQXHJQKDE-UHFFFAOYSA-N 0.000 description 4
• LALNEYRQNPHKNY-UHFFFAOYSA-N 4-[(6-chloro-8-oxo-2-propylsulfanyl-7H-purin-9-yl)methyl]benzonitrile Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C#N)C=C1)=O LALNEYRQNPHKNY-UHFFFAOYSA-N 0.000 description 4
• CTOBGOYAJNXTEK-UHFFFAOYSA-N 6-amino-2-methylsulfanyl-9-(pyridin-4-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SC)CC1=CC=NC=C1)=O CTOBGOYAJNXTEK-UHFFFAOYSA-N 0.000 description 4
• GTYRLXXHXBTNQV-UHFFFAOYSA-N 6-amino-9-[(2-chlorophenyl)methyl]-2-propylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=C(C=CC=C1)Cl)=O GTYRLXXHXBTNQV-UHFFFAOYSA-N 0.000 description 4
• VGSBMDOWAWHTIU-UHFFFAOYSA-N 6-amino-9-benzyl-2-ethylsulfanyl-7h-purin-8-one Chemical compound C12=NC(SCC)=NC(N)=C2N=C(O)N1CC1=CC=CC=C1 VGSBMDOWAWHTIU-UHFFFAOYSA-N 0.000 description 4
• FACAHUFBMGKRCZ-UHFFFAOYSA-N 6-chloro-4-N-[(2-methylpyrimidin-5-yl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC=1C=NC(=NC=1)C)N FACAHUFBMGKRCZ-UHFFFAOYSA-N 0.000 description 4
• SGBUPHFNZJHTSW-UHFFFAOYSA-N 6-chloro-4-N-[(3-chloro-4-methylphenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)C)Cl)N SGBUPHFNZJHTSW-UHFFFAOYSA-N 0.000 description 4
• HUEILCRXENNYJE-UHFFFAOYSA-N 6-chloro-N-[(2,4-difluorophenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=C(C=C(C=C1)F)F)[N+](=O)[O-] HUEILCRXENNYJE-UHFFFAOYSA-N 0.000 description 4
• 102000002260 Alkaline Phosphatase Human genes 0.000 description 4
• 108020004774 Alkaline Phosphatase Proteins 0.000 description 4
• QUMCIHKVKQYNPA-RUZDIDTESA-N C1(CCCCC1)CN1[C@@H](C=2N(C=3C=NC(=NC1=3)NC1=C(C=C(C(=O)NC3CCN(CC3)C)C=C1)OC)C(=NN=2)C)CC Chemical compound C1(CCCCC1)CN1[C@@H](C=2N(C=3C=NC(=NC1=3)NC1=C(C=C(C(=O)NC3CCN(CC3)C)C=C1)OC)C(=NN=2)C)CC QUMCIHKVKQYNPA-RUZDIDTESA-N 0.000 description 4
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
• 241000124008 Mammalia Species 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 238000011529 RT qPCR Methods 0.000 description 4
• 108010018242 Transcription Factor AP-1 Proteins 0.000 description 4
• 102100023132 Transcription factor Jun Human genes 0.000 description 4
• YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
• 239000000556 agonist Substances 0.000 description 4
• 230000000840 anti-viral effect Effects 0.000 description 4
• 238000003556 assay Methods 0.000 description 4
• MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• SMJYMSAPPGLBAR-UHFFFAOYSA-N chloromethyl acetate Chemical compound CC(=O)OCCl SMJYMSAPPGLBAR-UHFFFAOYSA-N 0.000 description 4
• 238000003818 flash chromatography Methods 0.000 description 4
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
• 239000003446 ligand Substances 0.000 description 4
• 108020004999 messenger RNA Proteins 0.000 description 4
• 239000002207 metabolite Substances 0.000 description 4
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
• 239000002777 nucleoside Substances 0.000 description 4
• 150000003833 nucleoside derivatives Chemical class 0.000 description 4
• 230000001590 oxidative effect Effects 0.000 description 4
• 239000008363 phosphate buffer Substances 0.000 description 4
• 230000034190 positive regulation of NF-kappaB transcription factor activity Effects 0.000 description 4
• 239000001294 propane Substances 0.000 description 4
• 108090000623 proteins and genes Proteins 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• 238000001228 spectrum Methods 0.000 description 4
• 230000004936 stimulating effect Effects 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
• AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 4
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
• FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 3
• LAJAFFLJAJMYLK-CVOKMOJFSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[(7s)-4-methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N1([C@H]2CCC3=CC=C(C(=C3CC2)OC)NC=2N=C(C(=CN=2)Cl)N[C@H]2[C@H]([C@@]3([H])C[C@@]2(C=C3)[H])C(N)=O)CCOCC1 LAJAFFLJAJMYLK-CVOKMOJFSA-N 0.000 description 3
• KSOVGRCOLZZTPF-QMKUDKLTSA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-[3-methyl-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC(C=C1C)=CC=C1N1CCN(C)CC1 KSOVGRCOLZZTPF-QMKUDKLTSA-N 0.000 description 3
• SYSGWPLRRPINQC-UHFFFAOYSA-N (2-methylpyridin-4-yl)methanamine Chemical compound CC1=CC(CN)=CC=N1 SYSGWPLRRPINQC-UHFFFAOYSA-N 0.000 description 3
• OYRGKUTZSTXSQS-UHFFFAOYSA-N (2-methylpyrimidin-5-yl)methanamine Chemical compound CC1=NC=C(CN)C=N1 OYRGKUTZSTXSQS-UHFFFAOYSA-N 0.000 description 3
• HOBMGFDJYBEWLS-UHFFFAOYSA-N (2-methylpyrimidin-5-yl)methanol Chemical compound CC1=NC=C(CO)C=N1 HOBMGFDJYBEWLS-UHFFFAOYSA-N 0.000 description 3
• SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 3
• DAAXYQZSKBPJOX-FQEVSTJZSA-N (2S)-2-amino-3-[4-[5-[3-(4-hydroxyphenyl)-4-methoxyphenyl]-1,2,4-oxadiazol-3-yl]phenyl]propanoic acid Chemical compound COC1=C(C=C(C=C1)C2=NC(=NO2)C3=CC=C(C=C3)C[C@@H](C(=O)O)N)C4=CC=C(C=C4)O DAAXYQZSKBPJOX-FQEVSTJZSA-N 0.000 description 3
• SLTBMTIRYMGWLX-XMMPIXPASA-N (2r)-2-[(4-chloroanilino)carbamoylamino]-3-(1h-indol-3-yl)-n-(2-phenylethyl)propanamide Chemical compound C1=CC(Cl)=CC=C1NNC(=O)N[C@@H](C(=O)NCCC=1C=CC=CC=1)CC1=CNC2=CC=CC=C12 SLTBMTIRYMGWLX-XMMPIXPASA-N 0.000 description 3
• KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 description 3
• LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-N 0.000 description 3
• AEVBPXDFDKBGLT-YOUFYPILSA-N (2s,3s,4r,5r)-n-[2-[4-(diethoxyphosphorylmethyl)anilino]-2-oxoethyl]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolane-2-carboxamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NC(=O)CNC(=O)[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 AEVBPXDFDKBGLT-YOUFYPILSA-N 0.000 description 3
• TWYYFYNJOJGNFP-CUXYNZQBSA-N (2s,4r,5s,6s)-2-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-2-carbamoyl-4-[[(e,4s,6s)-4,6-dimethyloct-2-enoyl]oxymethyl]-5-hydroxy-1,3-dioxane-4,5,6-tricarboxylic acid Chemical compound O1[C@H](C(O)=O)[C@](C(O)=O)(O)[C@](COC(=O)/C=C/[C@@H](C)C[C@@H](C)CC)(C(O)=O)O[C@]1(C(N)=O)CCC(=C)[C@@H](OC(C)=O)[C@H](C)CC1=CC=CC=C1 TWYYFYNJOJGNFP-CUXYNZQBSA-N 0.000 description 3
• FAVREULOXHXCQX-UHFFFAOYSA-N (4-chloro-3-methylphenyl)methanamine Chemical compound CC1=CC(CN)=CC=C1Cl FAVREULOXHXCQX-UHFFFAOYSA-N 0.000 description 3
• VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 3
• FRJJJAKBRKABFA-TYFAACHXSA-N (4r,6s)-6-[(e)-2-[6-chloro-4-(4-fluorophenyl)-2-propan-2-ylquinolin-3-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C(\[C@H]1OC(=O)C[C@H](O)C1)=C/C=1C(C(C)C)=NC2=CC=C(Cl)C=C2C=1C1=CC=C(F)C=C1 FRJJJAKBRKABFA-TYFAACHXSA-N 0.000 description 3
• BSGIKRCNMBTGEB-UHFFFAOYSA-N (5-bromo-1-methylpyrrolo[2,3-c]pyridin-2-yl)-[6-[(dimethylamino)methyl]-4-methyl-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound BrC1=NC=C2N(C)C(C(=O)N3CC(C4=CC(CN(C)C)=CC=C4C3)C)=CC2=C1 BSGIKRCNMBTGEB-UHFFFAOYSA-N 0.000 description 3
• JHLIGYPHPBLDDL-UHFFFAOYSA-N (5-pyridin-3-ylthiophen-2-yl)methanamine Chemical compound S1C(CN)=CC=C1C1=CC=CN=C1 JHLIGYPHPBLDDL-UHFFFAOYSA-N 0.000 description 3
• RXNPEQZHMGFNAY-GEALJGNFSA-N (5R)-4-[(1S,6R)-5-[(2S)-2-(4-chlorophenyl)-3-(propan-2-ylamino)propanoyl]-2,5-diazabicyclo[4.1.0]heptan-2-yl]-5-methyl-6,8-dihydro-5H-pyrido[2,3-d]pyrimidin-7-one Chemical compound C[C@@H]1CC(=O)NC2=C1C(=NC=N2)N3CCN([C@H]4[C@@H]3C4)C(=O)[C@H](CNC(C)C)C5=CC=C(C=C5)Cl RXNPEQZHMGFNAY-GEALJGNFSA-N 0.000 description 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
• IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 3
• VICOOSNNZUPVHM-IGPZRPDBSA-M (e,3r,5s)-7-[2-(4-fluorophenyl)-4-(3-phenylpentan-3-yl)phenyl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=CC=1C(CC)(CC)C1=CC=CC=C1 VICOOSNNZUPVHM-IGPZRPDBSA-M 0.000 description 3
• MXPCZHSTOIKVST-UHFFFAOYSA-N 1-[3-amino-2,6-di(propan-2-yl)phenyl]-3-[1-butyl-4-[3-(2-hydroxyethoxy)phenyl]-2-oxo-1,8-naphthyridin-3-yl]urea;hydrochloride Chemical compound Cl.CC(C)C=1C=CC(N)=C(C(C)C)C=1NC(=O)NC=1C(=O)N(CCCC)C2=NC=CC=C2C=1C1=CC=CC(OCCO)=C1 MXPCZHSTOIKVST-UHFFFAOYSA-N 0.000 description 3
• OXTVBHDILDPYAS-UHFFFAOYSA-N 1-[4-(aminomethyl)-2,6-di(propan-2-yl)phenyl]-3-[1-butyl-4-[3-(3-hydroxypropoxy)phenyl]-2-oxo-1,8-naphthyridin-3-yl]urea;hydrochloride Chemical compound Cl.CC(C)C=1C=C(CN)C=C(C(C)C)C=1NC(=O)NC=1C(=O)N(CCCC)C2=NC=CC=C2C=1C1=CC=CC(OCCCO)=C1 OXTVBHDILDPYAS-UHFFFAOYSA-N 0.000 description 3
• YRTFLDFDKPFNCJ-UHFFFAOYSA-N 1-[4-amino-2,6-di(propan-2-yl)phenyl]-3-[1-butyl-2-oxo-4-[3-(3-pyrrolidin-1-ylpropoxy)phenyl]-1,8-naphthyridin-3-yl]urea;dihydrochloride Chemical compound Cl.Cl.CC(C)C=1C=C(N)C=C(C(C)C)C=1NC(=O)NC=1C(=O)N(CCCC)C2=NC=CC=C2C=1C(C=1)=CC=CC=1OCCCN1CCCC1 YRTFLDFDKPFNCJ-UHFFFAOYSA-N 0.000 description 3
• ZFNNBIMQDHBELV-UHFFFAOYSA-N 1-[4-amino-2,6-di(propan-2-yl)phenyl]-3-[1-butyl-4-[3-(3-cyclohexylpropoxy)phenyl]-2-oxo-1,8-naphthyridin-3-yl]urea;dihydrochloride Chemical compound Cl.Cl.CC(C)C=1C=C(N)C=C(C(C)C)C=1NC(=O)NC=1C(=O)N(CCCC)C2=NC=CC=C2C=1C(C=1)=CC=CC=1OCCCC1CCCCC1 ZFNNBIMQDHBELV-UHFFFAOYSA-N 0.000 description 3
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
• YKYWUHHZZRBGMG-JWTNVVGKSA-N 1-methyl-2-[[(1r,5s)-6-[[5-(trifluoromethyl)pyridin-2-yl]methoxymethyl]-3-azabicyclo[3.1.0]hexan-3-yl]methyl]benzimidazole Chemical compound C1([C@@H]2CN(C[C@@H]21)CC=1N(C2=CC=CC=C2N=1)C)COCC1=CC=C(C(F)(F)F)C=N1 YKYWUHHZZRBGMG-JWTNVVGKSA-N 0.000 description 3
• FJMQJSUOOGOWBD-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound O=C1N(CC(F)(F)C)CCOC=2C1=NN(C=1C(=CC=CC=1)Cl)C=2C1=CC=C(Cl)C=C1 FJMQJSUOOGOWBD-UHFFFAOYSA-N 0.000 description 3
• XZORQADPEUSNQJ-UHFFFAOYSA-N 2-(3-piperidin-4-yloxy-1-benzothiophen-2-yl)-5-[(1,3,5-trimethylpyrazol-4-yl)methyl]-1,3,4-oxadiazole Chemical compound CC1=NN(C)C(C)=C1CC1=NN=C(C2=C(C3=CC=CC=C3S2)OC2CCNCC2)O1 XZORQADPEUSNQJ-UHFFFAOYSA-N 0.000 description 3
• CJLZUKCACMUYFP-GOSISDBHSA-N 2-[(5R)-4-[2-[3-(3-methylbutanoyloxy)phenyl]acetyl]-8-(trifluoromethyl)-1,2,3,5-tetrahydropyrido[2,3-e][1,4]diazepin-5-yl]acetic acid Chemical compound CC(C)CC(=O)OC1=CC=CC(CC(=O)N2[C@@H](C3=CC=C(N=C3NCC2)C(F)(F)F)CC(O)=O)=C1 CJLZUKCACMUYFP-GOSISDBHSA-N 0.000 description 3
• PFOQIHIIOLBCEQ-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethoxyphenyl)-7-methyl-3h-benzimidazol-5-yl]piperidin-1-yl]-n-methylethanamine Chemical compound C1CN(CCNC)CCC1C1=CC(C)=C(NC(=N2)C=3C(=CC=CC=3OC)OC)C2=C1 PFOQIHIIOLBCEQ-UHFFFAOYSA-N 0.000 description 3
• AXHVEQQLKVIZLO-UHFFFAOYSA-N 2-[4-[2-[5-(2,2-dimethylbutyl)-1h-imidazol-2-yl]ethyl]phenyl]benzoic acid Chemical compound CCC(C)(C)CC1=CNC(CCC=2C=CC(=CC=2)C=2C(=CC=CC=2)C(O)=O)=N1 AXHVEQQLKVIZLO-UHFFFAOYSA-N 0.000 description 3
• WGABOZPQOOZAOI-UHFFFAOYSA-N 2-[4-[[(3,5-dimethoxy-4-methylbenzoyl)-(3-phenylpropyl)amino]methyl]phenyl]acetic acid Chemical compound COC1=C(C)C(OC)=CC(C(=O)N(CCCC=2C=CC=CC=2)CC=2C=CC(CC(O)=O)=CC=2)=C1 WGABOZPQOOZAOI-UHFFFAOYSA-N 0.000 description 3
• BCSHRERPHLTPEE-NRFANRHFSA-N 2-[[5-chloro-2-[[(6s)-6-[4-(2-hydroxyethyl)piperazin-1-yl]-1-methoxy-6,7,8,9-tetrahydro-5h-benzo[7]annulen-2-yl]amino]pyrimidin-4-yl]amino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=NC(NC=2C(=C3CCC[C@@H](CC3=CC=2)N2CCN(CCO)CC2)OC)=NC=C1Cl BCSHRERPHLTPEE-NRFANRHFSA-N 0.000 description 3
• MEUWQVWJLLBVQI-UHFFFAOYSA-N 2-aminopropanedinitrile;4-methylbenzenesulfonic acid Chemical compound N#CC([NH3+])C#N.CC1=CC=C(S([O-])(=O)=O)C=C1 MEUWQVWJLLBVQI-UHFFFAOYSA-N 0.000 description 3
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 3
• SBWJLHPCEHEABR-UHFFFAOYSA-N 2-methylpyridine-4-carbonitrile Chemical compound CC1=CC(C#N)=CC=N1 SBWJLHPCEHEABR-UHFFFAOYSA-N 0.000 description 3
• IJBONYUNKRDIFC-UHFFFAOYSA-N 2-methylpyrimidine-5-carbaldehyde Chemical compound CC1=NC=C(C=O)C=N1 IJBONYUNKRDIFC-UHFFFAOYSA-N 0.000 description 3
• VGOALPIDEXVYQI-UHFFFAOYSA-N 3-(2-imidazo[1,2-b]pyridazin-3-ylethynyl)-n-[3-imidazol-1-yl-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound C1=C(C#CC=2N3N=CC=CC3=NC=2)C(C)=CC=C1C(=O)NC(C=C(C=1)C(F)(F)F)=CC=1N1C=CN=C1 VGOALPIDEXVYQI-UHFFFAOYSA-N 0.000 description 3
• HNFMVVHMKGFCMB-UHFFFAOYSA-N 3-[3-[4-(1-aminocyclobutyl)phenyl]-5-phenylimidazo[4,5-b]pyridin-2-yl]pyridin-2-amine Chemical compound NC1=NC=CC=C1C1=NC2=CC=C(C=3C=CC=CC=3)N=C2N1C1=CC=C(C2(N)CCC2)C=C1 HNFMVVHMKGFCMB-UHFFFAOYSA-N 0.000 description 3
• HCLQARMRCPEALF-DNQXCXABSA-N 3-[[(2r)-2-[(1r)-2-[[1-(1-benzothiophen-2-yl)-2-methylpropan-2-yl]amino]-1-hydroxyethyl]pyrrolidin-1-yl]methyl]benzonitrile Chemical compound C([C@@H]1[C@H](O)CNC(C)(CC=2SC3=CC=CC=C3C=2)C)CCN1CC1=CC=CC(C#N)=C1 HCLQARMRCPEALF-DNQXCXABSA-N 0.000 description 3
• HBVIITUOCCASKD-UHFFFAOYSA-N 3-[[(6-chloro-5-nitro-2-propylsulfanylpyrimidin-4-yl)amino]methyl]benzonitrile Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC=1C=C(C#N)C=CC=1)[N+](=O)[O-] HBVIITUOCCASKD-UHFFFAOYSA-N 0.000 description 3
• NVVPMZUGELHVMH-UHFFFAOYSA-N 3-ethyl-4-[4-[4-(1-methylpyrazol-4-yl)imidazol-1-yl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-1-yl]benzamide Chemical compound CCC1=CC(C(N)=O)=CC=C1N1C2=NC=CC(N3C=C(N=C3)C3=CN(C)N=C3)=C2C(C(C)C)=N1 NVVPMZUGELHVMH-UHFFFAOYSA-N 0.000 description 3
• GHAWBARMICSLQS-UHFFFAOYSA-N 4,6-dichloro-2-methylsulfanyl-5-nitropyrimidine Chemical compound CSC1=NC(Cl)=C([N+]([O-])=O)C(Cl)=N1 GHAWBARMICSLQS-UHFFFAOYSA-N 0.000 description 3
• TXEBWPPWSVMYOA-UHFFFAOYSA-N 4-[3-[(1-amino-2-chloroethyl)amino]propyl]-1-[[3-(2-chlorophenyl)phenyl]methyl]-5-hydroxyimidazolidin-2-one Chemical compound NC(CCl)NCCCC1NC(=O)N(Cc2cccc(c2)-c2ccccc2Cl)C1O TXEBWPPWSVMYOA-UHFFFAOYSA-N 0.000 description 3
• WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 description 3
• NGASIZRYYFJUCS-UHFFFAOYSA-N 4-[[(5-amino-6-chloro-2-propylsulfanylpyrimidin-4-yl)amino]methyl]benzonitrile Chemical compound NC=1C(=NC(=NC=1Cl)SCCC)NCC1=CC=C(C#N)C=C1 NGASIZRYYFJUCS-UHFFFAOYSA-N 0.000 description 3
• WCDJOBJYEDOSQS-UHFFFAOYSA-N 4-[[(6-chloro-5-nitro-2-propylsulfanylpyrimidin-4-yl)amino]methyl]benzonitrile Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C#N)C=C1)[N+](=O)[O-] WCDJOBJYEDOSQS-UHFFFAOYSA-N 0.000 description 3
• MFLMXRSHJVIMRF-DHIUTWEWSA-L 4-[[[5-[(3r,5r)-6-carboxylato-3,5-dihydroxyhexyl]-1-ethyl-4-(4-fluorophenyl)-3-methylpyrrole-2-carbonyl]amino]methyl]benzoate Chemical compound CCN1C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=2C=CC(F)=CC=2)C(C)=C1C(=O)NCC1=CC=C(C([O-])=O)C=C1 MFLMXRSHJVIMRF-DHIUTWEWSA-L 0.000 description 3
• KQXAFVQKMMSRFL-UHFFFAOYSA-N 4-amino-3-[(4-fluorophenyl)methyl]-2-oxo-1h-imidazole-5-carbonitrile Chemical compound NC1=C(C#N)N=C(O)N1CC1=CC=C(F)C=C1 KQXAFVQKMMSRFL-UHFFFAOYSA-N 0.000 description 3
• WBQWVGJKURKLHU-UHFFFAOYSA-N 4-amino-3-[(4-methoxyphenyl)methyl]-2-oxo-1h-imidazole-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1CN1C(=O)NC(C#N)=C1N WBQWVGJKURKLHU-UHFFFAOYSA-N 0.000 description 3
• VTFFVSSBNRTWCJ-UHFFFAOYSA-N 4-amino-3-[(6-chloropyridin-3-yl)methyl]-2-oxo-1H-imidazole-5-carbonitrile Chemical compound NC=1N(C(NC=1C#N)=O)CC=1C=NC(=CC=1)Cl VTFFVSSBNRTWCJ-UHFFFAOYSA-N 0.000 description 3
• JJNLGGQLCGZEIB-UHFFFAOYSA-N 4-amino-3-benzyl-2-oxo-1h-imidazole-5-carbonitrile Chemical compound NC1=C(C#N)N=C(O)N1CC1=CC=CC=C1 JJNLGGQLCGZEIB-UHFFFAOYSA-N 0.000 description 3
• MVXAKOGJWVQPKC-UHFFFAOYSA-N 5-(3-ethynyl-5-fluorophenyl)-2-pyridin-2-yl-4,6,7,8-tetrahydro-[1,3]oxazolo[4,5-c]azepine Chemical compound FC1=CC(C#C)=CC(N2CC=3N=C(OC=3CCC2)C=2N=CC=CC=2)=C1 MVXAKOGJWVQPKC-UHFFFAOYSA-N 0.000 description 3
• ZDHQVQVNOIWLNX-UHFFFAOYSA-N 5-(7-chloro-10h-benzo[1,2]cyclohepta[2,4-c][1,3]thiazol-10-yl)-1-methyl-4-sulfanylidenepyrimidin-2-one Chemical compound S=C1NC(=O)N(C)C=C1C1C2=CC=C(Cl)C=C2C=CC2=C1N=CS2 ZDHQVQVNOIWLNX-UHFFFAOYSA-N 0.000 description 3
• OXVHQOPLGOPEQO-UHFFFAOYSA-N 5-(azidomethyl)-2-methylpyrimidine Chemical compound CC1=NC=C(CN=[N+]=[N-])C=N1 OXVHQOPLGOPEQO-UHFFFAOYSA-N 0.000 description 3
• BJFRWQNIMZVQCT-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-9-(pyrimidin-5-ylmethyl)-7H-purin-8-one Chemical compound COC1=CC=C(C=C1)CNC1=C2NC(N(C2=NC(=N1)SCCC)CC=1C=NC=NC=1)=O BJFRWQNIMZVQCT-UHFFFAOYSA-N 0.000 description 3
• DBMPIOFKGCJGNJ-UHFFFAOYSA-N 6-amino-2-(3-chloropropylsulfanyl)-9-[(4-methoxyphenyl)methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCCCl)CC1=CC=C(C=C1)OC)=O DBMPIOFKGCJGNJ-UHFFFAOYSA-N 0.000 description 3
• WZLWMPJFCVDACR-UHFFFAOYSA-N 6-amino-2-(3-chloropropylsulfinyl)-9-[(4-methoxyphenyl)methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCCCl)CC1=CC=C(C=C1)OC)=O WZLWMPJFCVDACR-UHFFFAOYSA-N 0.000 description 3
• GHUKPLITXIFSRK-UHFFFAOYSA-N 6-amino-2-ethylsulfanyl-9-[(4-fluorophenyl)methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCC)CC1=CC=C(C=C1)F)=O GHUKPLITXIFSRK-UHFFFAOYSA-N 0.000 description 3
• YMHLABHVGRFDEB-UHFFFAOYSA-N 6-amino-2-methylsulfanyl-9-(pyridin-2-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SC)CC1=NC=CC=C1)=O YMHLABHVGRFDEB-UHFFFAOYSA-N 0.000 description 3
• DKVUFKHNPXDUEA-UHFFFAOYSA-N 6-amino-2-methylsulfinyl-9-(pyridin-2-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)C)CC1=NC=CC=C1)=O DKVUFKHNPXDUEA-UHFFFAOYSA-N 0.000 description 3
• QJWPPRMYXGFYES-UHFFFAOYSA-N 6-amino-2-propylsulfanyl-9-(pyridin-2-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=NC=CC=C1)=O QJWPPRMYXGFYES-UHFFFAOYSA-N 0.000 description 3
• UTKOWHRNPQDYNX-UHFFFAOYSA-N 6-amino-9-[(2-chlorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=C(C=CC=C1)Cl)=O UTKOWHRNPQDYNX-UHFFFAOYSA-N 0.000 description 3
• ICPOUPIDKAVXEK-UHFFFAOYSA-N 6-amino-9-[(4-chloro-3-methylphenyl)methyl]-2-propylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=CC(=C(C=C1)Cl)C)=O ICPOUPIDKAVXEK-UHFFFAOYSA-N 0.000 description 3
• KRZHDKNRAJEVTE-UHFFFAOYSA-N 6-chloro-2-methylsulfanyl-4-N-(pyridin-2-ylmethyl)pyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SC)NCC1=NC=CC=C1)N KRZHDKNRAJEVTE-UHFFFAOYSA-N 0.000 description 3
• QXUVSSHJGKGJNJ-UHFFFAOYSA-N 6-chloro-2-methylsulfanyl-4-N-(pyridin-3-ylmethyl)pyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SC)NCC=1C=NC=CC=1)N QXUVSSHJGKGJNJ-UHFFFAOYSA-N 0.000 description 3
• WNRUNFGVYGGGEW-UHFFFAOYSA-N 6-chloro-2-methylsulfanyl-4-N-(pyridin-4-ylmethyl)pyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SC)NCC1=CC=NC=C1)N WNRUNFGVYGGGEW-UHFFFAOYSA-N 0.000 description 3
• RUCNHSPYGHWHHI-UHFFFAOYSA-N 6-chloro-2-methylsulfanyl-5-nitro-N-(pyridin-2-ylmethyl)pyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SC)NCC1=NC=CC=C1)[N+](=O)[O-] RUCNHSPYGHWHHI-UHFFFAOYSA-N 0.000 description 3
• UJASXHABCYKAAY-UHFFFAOYSA-N 6-chloro-2-methylsulfanyl-5-nitro-N-(pyridin-3-ylmethyl)pyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SC)NCC=1C=NC=CC=1)[N+](=O)[O-] UJASXHABCYKAAY-UHFFFAOYSA-N 0.000 description 3
• ZUWKQLJELLHMNF-UHFFFAOYSA-N 6-chloro-2-methylsulfanyl-5-nitro-N-(pyridin-4-ylmethyl)pyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SC)NCC1=CC=NC=C1)[N+](=O)[O-] ZUWKQLJELLHMNF-UHFFFAOYSA-N 0.000 description 3
• NMFIDGJEOBNXRX-UHFFFAOYSA-N 6-chloro-2-propylsulfanyl-4-N-(pyrimidin-5-ylmethyl)pyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC=1C=NC=NC=1)N NMFIDGJEOBNXRX-UHFFFAOYSA-N 0.000 description 3
• XEAFUKUFFYDCJW-UHFFFAOYSA-N 6-chloro-4-N-(2-methylpropyl)-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC(C)C)N XEAFUKUFFYDCJW-UHFFFAOYSA-N 0.000 description 3
• PGAZPPBBUCHVLC-UHFFFAOYSA-N 6-chloro-4-N-[(4-chlorophenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)Cl)N PGAZPPBBUCHVLC-UHFFFAOYSA-N 0.000 description 3
• AOKMWWYZIJZZPG-UHFFFAOYSA-N 6-chloro-4-N-[(4-methylsulfonylphenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)S(=O)(=O)C)N AOKMWWYZIJZZPG-UHFFFAOYSA-N 0.000 description 3
• QKYJEBSTOJMWSP-UHFFFAOYSA-N 6-chloro-5-nitro-2-propylsulfanyl-N-(pyrimidin-5-ylmethyl)pyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC=1C=NC=NC=1)[N+](=O)[O-] QKYJEBSTOJMWSP-UHFFFAOYSA-N 0.000 description 3
• LXXRXUXKBMMOND-UHFFFAOYSA-N 6-chloro-5-nitro-2-propylsulfanyl-N-[[4-(trifluoromethyl)phenyl]methyl]pyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)C(F)(F)F)[N+](=O)[O-] LXXRXUXKBMMOND-UHFFFAOYSA-N 0.000 description 3
• VVUGFKRMHUVWKW-UHFFFAOYSA-N 6-chloro-9-(2-methylpropyl)-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC(C)C)=O VVUGFKRMHUVWKW-UHFFFAOYSA-N 0.000 description 3
• JDOBRVSTRUYTDL-UHFFFAOYSA-N 6-chloro-9-[(4-chloro-3-methylphenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)Cl)C)=O JDOBRVSTRUYTDL-UHFFFAOYSA-N 0.000 description 3
• ORDPCCHDEXLZTD-UHFFFAOYSA-N 6-chloro-N-(2-methylpropyl)-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC(C)C)[N+](=O)[O-] ORDPCCHDEXLZTD-UHFFFAOYSA-N 0.000 description 3
• BNOSSHBESCFNTN-UHFFFAOYSA-N 6-chloro-N-[(2-methylpyridin-4-yl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=NC=C1)C)[N+](=O)[O-] BNOSSHBESCFNTN-UHFFFAOYSA-N 0.000 description 3
• ZDZWHRKMDNGFPZ-UHFFFAOYSA-N 6-chloro-N-[(3,4-difluorophenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)F)F)[N+](=O)[O-] ZDZWHRKMDNGFPZ-UHFFFAOYSA-N 0.000 description 3
• MUYFKRZEPDBDKF-UHFFFAOYSA-N 6-chloro-N-[(3-chlorophenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=CC=C1)Cl)[N+](=O)[O-] MUYFKRZEPDBDKF-UHFFFAOYSA-N 0.000 description 3
• BFUSDYFIXSTGJB-UHFFFAOYSA-N 6-chloro-N-[(4-chloro-3-fluorophenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)Cl)F)[N+](=O)[O-] BFUSDYFIXSTGJB-UHFFFAOYSA-N 0.000 description 3
• VVSKHEUAQMVQFU-UHFFFAOYSA-N 6-chloro-N-[(4-chlorophenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)Cl)[N+](=O)[O-] VVSKHEUAQMVQFU-UHFFFAOYSA-N 0.000 description 3
• KUISQZDVMKSVNP-UHFFFAOYSA-N 6-chloro-N-[(4-methylsulfonylphenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)S(=O)(=O)C)[N+](=O)[O-] KUISQZDVMKSVNP-UHFFFAOYSA-N 0.000 description 3
• HHHPGQBUWHNQDE-UHFFFAOYSA-N 6-chloro-N-[(6-methylpyridin-3-yl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC=1C=NC(=CC=1)C)[N+](=O)[O-] HHHPGQBUWHNQDE-UHFFFAOYSA-N 0.000 description 3
• PBLOYQAQGYUPCM-UHFFFAOYSA-N 6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C=N1 PBLOYQAQGYUPCM-UHFFFAOYSA-N 0.000 description 3
• XTJZKALDRPVFSN-HNNXBMFYSA-N 8-n-[(2s)-3,3-dimethylbutan-2-yl]-2-n-[2-methoxy-4-(1-methylpyrazol-4-yl)phenyl]pyrido[3,4-d]pyrimidine-2,8-diamine Chemical compound C=1C=C(NC=2N=C3C(N[C@@H](C)C(C)(C)C)=NC=CC3=CN=2)C(OC)=CC=1C=1C=NN(C)C=1 XTJZKALDRPVFSN-HNNXBMFYSA-N 0.000 description 3
• MCMSJVMUSBZUCN-UHFFFAOYSA-N 9,10-dimethoxy-3-methyl-2-(2,4,6-trimethylphenyl)imino-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C(N2C)=O)C1=CC2=NC1=C(C)C=C(C)C=C1C MCMSJVMUSBZUCN-UHFFFAOYSA-N 0.000 description 3
• VWVKUNOPTJGDOB-BDHVOXNPSA-N Anhydrous tofogliflozin Chemical compound C1=CC(CC)=CC=C1CC1=CC=C(CO[C@@]23[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C2=C1 VWVKUNOPTJGDOB-BDHVOXNPSA-N 0.000 description 3
• JAOGFYSXDYNYSX-UHFFFAOYSA-N CC(C)(C(N=CC(Cl)=C1)=C1C(C=CC(Cl)=C1)=C1N1C(C=C2)=CC=C2N(C2)CC2(CNC(CC2)CCC2C(O)=O)F)C1=O Chemical compound CC(C)(C(N=CC(Cl)=C1)=C1C(C=CC(Cl)=C1)=C1N1C(C=C2)=CC=C2N(C2)CC2(CNC(CC2)CCC2C(O)=O)F)C1=O JAOGFYSXDYNYSX-UHFFFAOYSA-N 0.000 description 3
• QCMHGCDOZLWPOT-FMNCTDSISA-N COC1=C(CC[C@@H]2CCC3=C(C2)C=CC(=C3)[C@H]2CC[C@](N)(CO)C2)C=CC=C1 Chemical compound COC1=C(CC[C@@H]2CCC3=C(C2)C=CC(=C3)[C@H]2CC[C@](N)(CO)C2)C=CC=C1 QCMHGCDOZLWPOT-FMNCTDSISA-N 0.000 description 3
• WUZBOJXXYMKMMF-UHFFFAOYSA-N COC1=CC2=NC=3N(C(N(C(C=3N2C=C1)=O)CCC)=O)CCCCNC(=O)C1=CC=C(C=C1)S(=O)(=O)F Chemical compound COC1=CC2=NC=3N(C(N(C(C=3N2C=C1)=O)CCC)=O)CCCCNC(=O)C1=CC=C(C=C1)S(=O)(=O)F WUZBOJXXYMKMMF-UHFFFAOYSA-N 0.000 description 3
• WLRJOPVHBALWFW-UHFFFAOYSA-N CS(NC(N=C1N2CC3=CC=CN=C3)=NC(N)=C1NC2=O)(=O)=O Chemical compound CS(NC(N=C1N2CC3=CC=CN=C3)=NC(N)=C1NC2=O)(=O)=O WLRJOPVHBALWFW-UHFFFAOYSA-N 0.000 description 3
• 229940126657 Compound 17 Drugs 0.000 description 3
• 108090000695 Cytokines Proteins 0.000 description 3
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
• 206010013710 Drug interaction Diseases 0.000 description 3
• 241000700721 Hepatitis B virus Species 0.000 description 3
• 101000652482 Homo sapiens TBC1 domain family member 8 Proteins 0.000 description 3
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
• HPKJGHVHQWJOOT-ZJOUEHCJSA-N N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide Chemical compound C1C(CCCC1)C[C@H](NC(=O)C=1NC2=CC=CC=C2C=1)C(=O)N[C@@H](C[C@H]1C(=O)NCC1)C=O HPKJGHVHQWJOOT-ZJOUEHCJSA-N 0.000 description 3
• OHVIRCSJFFPEGC-XMMPIXPASA-N N-[3-[[4-[[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]phenyl]methoxy]phenyl]benzamide Chemical compound OC[C@H]1CCCN1Cc1ccc(COc2cccc(NC(=O)c3ccccc3)c2)cc1 OHVIRCSJFFPEGC-XMMPIXPASA-N 0.000 description 3
• ZVDOSPMSDOICBO-UHFFFAOYSA-N N-benzyl-6-chloro-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound C(C1=CC=CC=C1)NC1=NC(=NC(=C1[N+](=O)[O-])Cl)SCCC ZVDOSPMSDOICBO-UHFFFAOYSA-N 0.000 description 3
• TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 3
• KISZAGQTIXIVAR-UHFFFAOYSA-N OC(=O)c1ccc2c(CCCC(c3ccc(Cl)cc3Cl)=C2c2ccc(OC3CCN(CCCF)C3)cc2)c1 Chemical compound OC(=O)c1ccc2c(CCCC(c3ccc(Cl)cc3Cl)=C2c2ccc(OC3CCN(CCCF)C3)cc2)c1 KISZAGQTIXIVAR-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 229930182555 Penicillin Natural products 0.000 description 3
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
• 102100030302 TBC1 domain family member 8 Human genes 0.000 description 3
• KZVWEOXAPZXAFB-BQFCYCMXSA-N Temocaprilat Chemical compound C([C@H](N[C@H]1CS[C@@H](CN(C1=O)CC(=O)O)C=1SC=CC=1)C(O)=O)CC1=CC=CC=C1 KZVWEOXAPZXAFB-BQFCYCMXSA-N 0.000 description 3
• 208000036142 Viral infection Diseases 0.000 description 3
• NPUXORBZRBIOMQ-RUZDIDTESA-N [(2R)-1-[[4-[[3-(benzenesulfonylmethyl)-5-methylphenoxy]methyl]phenyl]methyl]-2-pyrrolidinyl]methanol Chemical compound C=1C(OCC=2C=CC(CN3[C@H](CCC3)CO)=CC=2)=CC(C)=CC=1CS(=O)(=O)C1=CC=CC=C1 NPUXORBZRBIOMQ-RUZDIDTESA-N 0.000 description 3
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[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@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
• 150000001263 acyl chlorides Chemical class 0.000 description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
• SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 239000012298 atmosphere Substances 0.000 description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
• AJRQIXBBIDPNGK-BVSLBCMMSA-N benzyl n-[(2s)-1-[[(2s)-1-(1,3-benzothiazol-2-yl)-1-oxo-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](C[C@H]1C(NCC1)=O)C(=O)C=1SC2=CC=CC=C2N=1)C(=O)OCC1=CC=CC=C1 AJRQIXBBIDPNGK-BVSLBCMMSA-N 0.000 description 3
• 210000004369 blood Anatomy 0.000 description 3
• 239000008280 blood Substances 0.000 description 3
• OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 238000004113 cell culture Methods 0.000 description 3
• AEULIVPVIDOLIN-UHFFFAOYSA-N cep-11981 Chemical compound C1=C2C3=C4CNC(=O)C4=C4C5=CN(C)N=C5CCC4=C3N(CC(C)C)C2=CC=C1NC1=NC=CC=N1 AEULIVPVIDOLIN-UHFFFAOYSA-N 0.000 description 3
• 230000008859 change Effects 0.000 description 3
• JQXXHWHPUNPDRT-BQVAUQFYSA-N chembl1523493 Chemical compound O([C@](C1=O)(C)O\C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2C=NN1CCN(C)CC1 JQXXHWHPUNPDRT-BQVAUQFYSA-N 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 229940127206 compound 14d Drugs 0.000 description 3
• 229940126212 compound 17a Drugs 0.000 description 3
• 229940126209 compound 43b Drugs 0.000 description 3
• 229940126211 compound 54c Drugs 0.000 description 3
• 229940125873 compound 60b Drugs 0.000 description 3
• 239000012043 crude product Substances 0.000 description 3
• 125000000753 cycloalkyl group Chemical group 0.000 description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
• 238000001514 detection method Methods 0.000 description 3
• 239000003085 diluting agent Substances 0.000 description 3
• 208000035475 disorder Diseases 0.000 description 3
• 239000002552 dosage form Substances 0.000 description 3
• 238000012377 drug delivery Methods 0.000 description 3
• 229960002989 glutamic acid Drugs 0.000 description 3
• KUCDOJMOTMEEOF-UHFFFAOYSA-N gtpl6345 Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(SC=2C3=C4NCCOC4=CN=2)=C3N=C1 KUCDOJMOTMEEOF-UHFFFAOYSA-N 0.000 description 3
• FODONWGPMXPGNC-UHFFFAOYSA-N gtpl6346 Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C(SC=2C3=C4NCCOC4=CN=2)=C3N=C1 FODONWGPMXPGNC-UHFFFAOYSA-N 0.000 description 3
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
• 238000000338 in vitro Methods 0.000 description 3
• 238000001727 in vivo Methods 0.000 description 3
• 238000011534 incubation Methods 0.000 description 3
• 208000015181 infectious disease Diseases 0.000 description 3
• 230000005764 inhibitory process Effects 0.000 description 3
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 3
• 239000007937 lozenge Substances 0.000 description 3
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
• LBVOQOIJQBTHOE-UHFFFAOYSA-N methyl 4-[(6-amino-8-oxo-2-propylsulfanyl-7H-purin-9-yl)methyl]benzoate Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C(=O)OC)C=C1)=O LBVOQOIJQBTHOE-UHFFFAOYSA-N 0.000 description 3
• UIBNRGRUBIMSKX-UHFFFAOYSA-N methyl 4-[(6-chloro-8-oxo-2-propylsulfanyl-7H-purin-9-yl)methyl]benzoate Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C(=O)OC)C=C1)=O UIBNRGRUBIMSKX-UHFFFAOYSA-N 0.000 description 3
• WMLAZUKQQASVQF-UHFFFAOYSA-N methyl 4-[[(6-chloro-5-methyl-2-propylsulfanylpyrimidin-4-yl)amino]methyl]benzoate Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C(=O)OC)C=C1)C WMLAZUKQQASVQF-UHFFFAOYSA-N 0.000 description 3
• GYDHDHHCACIZIC-UHFFFAOYSA-N methyl 4-[[(6-chloro-5-nitro-2-propylsulfanylpyrimidin-4-yl)amino]methyl]benzoate Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C(=O)OC)C=C1)[N+](=O)[O-] GYDHDHHCACIZIC-UHFFFAOYSA-N 0.000 description 3
• SKEAGJWUKCNICJ-LSDHHAIUSA-N n-[(4-fluoro-3-methoxyphenyl)methyl]-6-[2-[[(2s,5r)-5-(hydroxymethyl)-1,4-dioxan-2-yl]methyl]tetrazol-5-yl]-2-methylpyrimidine-4-carboxamide Chemical compound C1=C(F)C(OC)=CC(CNC(=O)C=2N=C(C)N=C(C=2)C2=NN(C[C@@H]3OC[C@@H](CO)OC3)N=N2)=C1 SKEAGJWUKCNICJ-LSDHHAIUSA-N 0.000 description 3
• NFPUARSXIMWASK-GOEBONIOSA-N n-[(5r,7s)-2-(3-chlorophenyl)-1-oxa-3-azaspiro[4.5]dec-2-en-7-yl]acetamide Chemical compound C1[C@@H](NC(=O)C)CCC[C@@]11OC(C=2C=C(Cl)C=CC=2)=NC1 NFPUARSXIMWASK-GOEBONIOSA-N 0.000 description 3
• PHVXTQIROLEEDB-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-4-[[3-(2-methylphenyl)piperidin-1-yl]methyl]-n-pyrrolidin-3-ylbenzamide Chemical compound CC1=CC=CC=C1C1CN(CC=2C=CC(=CC=2)C(=O)N(CCC=2C(=CC=CC=2)Cl)C2CNCC2)CCC1 PHVXTQIROLEEDB-UHFFFAOYSA-N 0.000 description 3
• MUJNAWXXOJRNGK-UHFFFAOYSA-N n-[3-(6-methyl-1,2,3,4-tetrahydrocarbazol-9-yl)propyl]cyclohexanamine Chemical compound C1=2CCCCC=2C2=CC(C)=CC=C2N1CCCNC1CCCCC1 MUJNAWXXOJRNGK-UHFFFAOYSA-N 0.000 description 3
• CJPMSUUANYLPET-UHFFFAOYSA-N n-[3-[[5-cyclopropyl-2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCNC(C(=CN=1)C2CC2)=NC=1NC(C=C1)=CC=C1N1CCOCC1 CJPMSUUANYLPET-UHFFFAOYSA-N 0.000 description 3
• MUWDEQLPHWVPPA-GOTSBHOMSA-N n-[6-oxo-6-[(3s,4s)-3-[(4-phenoxyphenyl)sulfonylamino]-4-sulfanylpyrrolidin-1-yl]hexyl]acetamide Chemical compound C1N(C(=O)CCCCCNC(=O)C)C[C@H](S)[C@H]1NS(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 MUWDEQLPHWVPPA-GOTSBHOMSA-N 0.000 description 3
• YRCHYHRCBXNYNU-UHFFFAOYSA-N n-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide Chemical compound N1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=S)NC(=O)CC=4C=CC(F)=CC=4)=CC=3)F)=C2S1 YRCHYHRCBXNYNU-UHFFFAOYSA-N 0.000 description 3
• 239000012299 nitrogen atmosphere Substances 0.000 description 3
• ASOADIZOVZTJSR-UHFFFAOYSA-N opicapone Chemical compound CC1=C(Cl)C(C)=[N+]([O-])C(Cl)=C1C1=NOC(C=2C=C(C(O)=C(O)C=2)[N+]([O-])=O)=N1 ASOADIZOVZTJSR-UHFFFAOYSA-N 0.000 description 3
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
• 229940049954 penicillin Drugs 0.000 description 3
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
• 229920001296 polysiloxane Polymers 0.000 description 3
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
• 239000013641 positive control Substances 0.000 description 3
• 238000011533 pre-incubation Methods 0.000 description 3
• 230000008569 process Effects 0.000 description 3
• 230000001105 regulatory effect Effects 0.000 description 3
• RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 0.000 description 3
• 229960001225 rifampicin Drugs 0.000 description 3
• 230000019491 signal transduction Effects 0.000 description 3
• 239000000741 silica gel Substances 0.000 description 3
• 229910002027 silica gel Inorganic materials 0.000 description 3
• 229910052938 sodium sulfate Inorganic materials 0.000 description 3
• 235000011152 sodium sulphate Nutrition 0.000 description 3
• 230000000638 stimulation Effects 0.000 description 3
• 229960005322 streptomycin Drugs 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• 239000006228 supernatant Substances 0.000 description 3
• YKEGUYTXACKXKS-IRXDYDNUSA-N tert-butyl (1s,5s)-3-[5-methyl-6-(2-methylpyridin-3-yl)oxypyrimidin-4-yl]oxy-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound CC1=NC=CC=C1OC1=NC=NC(OC2C[C@@H]3CC[C@H](N3C(=O)OC(C)(C)C)C2)=C1C YKEGUYTXACKXKS-IRXDYDNUSA-N 0.000 description 3
• JYRWUSXRTGACLY-UHFFFAOYSA-N tert-butyl 4-[[3-(4-methylsulfonylphenyl)-[1,2]oxazolo[4,5-d]pyrimidin-7-yl]oxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC2=C1ON=C2C1=CC=C(S(C)(=O)=O)C=C1 JYRWUSXRTGACLY-UHFFFAOYSA-N 0.000 description 3
• FRACPXUHUTXLCX-BELIEFIBSA-N tert-butyl N-{1-[(1S)-1-{[(1R,2S)-1-(benzylcarbamoyl)-1-hydroxy-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]carbamoyl}-2-cyclopropylethyl]-2-oxopyridin-3-yl}carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CN(C1=O)[C@@H](CC2CC2)C(=O)N[C@@H](C[C@@H]3CCNC3=O)[C@H](C(=O)NCC4=CC=CC=C4)O FRACPXUHUTXLCX-BELIEFIBSA-N 0.000 description 3
• 239000003643 water by type Substances 0.000 description 3
• YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
• ZXGVFUKWWWNTTQ-VSGBNLITSA-N (3r,5r)-7-[4-[[3-(2-amino-2-oxoethyl)phenyl]sulfamoyl]-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NC=2C=C(CC(N)=O)C=CC=2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 ZXGVFUKWWWNTTQ-VSGBNLITSA-N 0.000 description 2
• HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 2
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
• 102000040650 (ribonucleotides)n+m Human genes 0.000 description 2
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
• CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
• CGKKDGMMKSOGLM-UHFFFAOYSA-N 1-chloroethyl acetate Chemical compound CC(Cl)OC(C)=O CGKKDGMMKSOGLM-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• XUXJHBAJZQREDB-UHFFFAOYSA-N 2-methylbutanamide Chemical compound CCC(C)C(N)=O XUXJHBAJZQREDB-UHFFFAOYSA-N 0.000 description 2
• UMFWRNLJDQMTFR-UHFFFAOYSA-N 2-methylpentyl 2-methylpentanoate Chemical compound CCCC(C)COC(=O)C(C)CCC UMFWRNLJDQMTFR-UHFFFAOYSA-N 0.000 description 2
• OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
• UNSHMXUHOHBLIQ-UHFFFAOYSA-N 3-[4-chloro-3-(2-methylphenoxy)naphthalen-1-yl]-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione Chemical compound ClC1=C(C=C(C2=CC=CC=C12)N1C(NC(=CC1=O)C(F)(F)F)=O)OC1=C(C=CC=C1)C UNSHMXUHOHBLIQ-UHFFFAOYSA-N 0.000 description 2
• XYLHEQDKJGBQSZ-UHFFFAOYSA-N 3-[[(5-amino-6-chloro-2-propylsulfanylpyrimidin-4-yl)amino]methyl]benzonitrile Chemical compound NC=1C(=NC(=NC=1Cl)SCCC)NCC=1C=C(C#N)C=CC=1 XYLHEQDKJGBQSZ-UHFFFAOYSA-N 0.000 description 2
• JLOFVZKCYFDECG-UHFFFAOYSA-N 4-N-[(4-bromophenyl)methyl]-6-chloro-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)Br)N JLOFVZKCYFDECG-UHFFFAOYSA-N 0.000 description 2
• UJDPPTCEWWVWCL-UHFFFAOYSA-N 4-benzyl-6-chloro-2-propylsulfanyl-1H-pyrimidine-4,5-diamine Chemical compound C(C1=CC=CC=C1)C1(NC(=NC(=C1N)Cl)SCCC)N UJDPPTCEWWVWCL-UHFFFAOYSA-N 0.000 description 2
• VLWRKVBQUANIGI-UHFFFAOYSA-N 4-fluoro-n-methylaniline Chemical compound CNC1=CC=C(F)C=C1 VLWRKVBQUANIGI-UHFFFAOYSA-N 0.000 description 2
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
• SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 2
• OQCBZUQZGVEIGQ-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylamino]-2-methylsulfanyl-9-(pyridin-2-ylmethyl)-7H-purin-8-one Chemical compound COC1=CC=C(C=C1)CNC1=C2NC(N(C2=NC(=N1)SC)CC1=NC=CC=C1)=O OQCBZUQZGVEIGQ-UHFFFAOYSA-N 0.000 description 2
• VDOPMXYXDRHECX-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylamino]-2-methylsulfanyl-9-(pyridin-3-ylmethyl)-7H-purin-8-one Chemical compound COC1=CC=C(C=C1)CNC1=C2NC(N(C2=NC(=N1)SC)CC=1C=NC=CC=1)=O VDOPMXYXDRHECX-UHFFFAOYSA-N 0.000 description 2
• WRRFKRBECKNCGX-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylamino]-9-(2-methylpropyl)-2-propylsulfanyl-7H-purin-8-one Chemical compound C(C(C)C)N1C2=NC(=NC(=C2NC1=O)NCC1=CC=C(C=C1)OC)SCCC WRRFKRBECKNCGX-UHFFFAOYSA-N 0.000 description 2
• XDBHURGONHZNJF-UHFFFAOYSA-N 6-[2-(3,4-diethoxyphenyl)-1,3-thiazol-4-yl]pyridine-2-carboxylic acid Chemical compound C1=C(OCC)C(OCC)=CC=C1C1=NC(C=2N=C(C=CC=2)C(O)=O)=CS1 XDBHURGONHZNJF-UHFFFAOYSA-N 0.000 description 2
• GJZIAFLOUZRSMO-UHFFFAOYSA-N 6-amino-2-methylsulfinyl-9-(pyridin-3-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)C)CC=1C=NC=CC=1)=O GJZIAFLOUZRSMO-UHFFFAOYSA-N 0.000 description 2
• GNNWYIXQIMYPDF-UHFFFAOYSA-N 6-amino-2-propylsulfinyl-9-[[4-(trifluoromethyl)phenyl]methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=CC=C(C=C1)C(F)(F)F)=O GNNWYIXQIMYPDF-UHFFFAOYSA-N 0.000 description 2
• PAAMUPBWXLCXNH-UHFFFAOYSA-N 6-amino-9-[(4-chlorophenyl)methyl]-2-ethylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCC)CC1=CC=C(C=C1)Cl)=O PAAMUPBWXLCXNH-UHFFFAOYSA-N 0.000 description 2
• FBFBHKHVBSHQDY-UHFFFAOYSA-N 6-amino-9-[(4-chlorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)Cl)=O FBFBHKHVBSHQDY-UHFFFAOYSA-N 0.000 description 2
• XNENYEMLFACNFU-UHFFFAOYSA-N 6-amino-9-[(4-chlorophenyl)methyl]-2-sulfanylidene-1,7-dihydropurin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S)CC1=CC=C(C=C1)Cl)=O XNENYEMLFACNFU-UHFFFAOYSA-N 0.000 description 2
• CIJFULQSEGMRNI-UHFFFAOYSA-N 6-amino-9-[(4-fluorophenyl)methyl]-2-propylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=CC=C(C=C1)F)=O CIJFULQSEGMRNI-UHFFFAOYSA-N 0.000 description 2
• FATSPKACVVCXGN-UHFFFAOYSA-N 6-amino-9-[(4-methylphenyl)methyl]-2-propylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=CC=C(C=C1)C)=O FATSPKACVVCXGN-UHFFFAOYSA-N 0.000 description 2
• TWIUELNOSZKELU-UHFFFAOYSA-N 6-amino-9-[(6-chloropyridin-3-yl)methyl]-2-sulfanylidene-1,7-dihydropurin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S)CC=1C=NC(=CC=1)Cl)=O TWIUELNOSZKELU-UHFFFAOYSA-N 0.000 description 2
• VFZUVWZQMMOSCU-UHFFFAOYSA-N 6-amino-9-benzyl-2-(2,2,2-trifluoroethylsulfanyl)-7h-purin-8-one Chemical compound OC1=NC=2C(N)=NC(SCC(F)(F)F)=NC=2N1CC1=CC=CC=C1 VFZUVWZQMMOSCU-UHFFFAOYSA-N 0.000 description 2
• BMIUMQBNFDNIMK-UHFFFAOYSA-N 6-amino-9-benzyl-2-(2-methoxyethylsulfanyl)-7h-purin-8-one Chemical compound C12=NC(SCCOC)=NC(N)=C2N=C(O)N1CC1=CC=CC=C1 BMIUMQBNFDNIMK-UHFFFAOYSA-N 0.000 description 2
• RKOAQZHSBQHMDM-UHFFFAOYSA-N 6-amino-9-benzyl-2-(2-methoxyethylsulfinyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCOC)CC1=CC=CC=C1)=O RKOAQZHSBQHMDM-UHFFFAOYSA-N 0.000 description 2
• UYYSNQIRKWLHAD-UHFFFAOYSA-N 6-amino-9-benzyl-2-butylsulfanyl-7h-purin-8-one Chemical compound C12=NC(SCCCC)=NC(N)=C2N=C(O)N1CC1=CC=CC=C1 UYYSNQIRKWLHAD-UHFFFAOYSA-N 0.000 description 2
• AYHFCRLYOXQOIM-UHFFFAOYSA-N 6-chloro-2-methylsulfanyl-9-(pyridin-2-ylmethyl)-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SC)CC1=NC=CC=C1)=O AYHFCRLYOXQOIM-UHFFFAOYSA-N 0.000 description 2
• YPWGGFUUDUCVMW-UHFFFAOYSA-N 6-chloro-2-methylsulfanyl-9-(pyridin-4-ylmethyl)-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SC)CC1=CC=NC=C1)=O YPWGGFUUDUCVMW-UHFFFAOYSA-N 0.000 description 2
• AYNPKJQFAPISAZ-UHFFFAOYSA-N 6-chloro-2-propylsulfanyl-4-N-[[4-(trifluoromethyl)phenyl]methyl]pyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)C(F)(F)F)N AYNPKJQFAPISAZ-UHFFFAOYSA-N 0.000 description 2
• JGJZMBYOSLNMPD-UHFFFAOYSA-N 6-chloro-4-N-[(2,4-difluorophenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=C(C=C(C=C1)F)F)N JGJZMBYOSLNMPD-UHFFFAOYSA-N 0.000 description 2
• ZCPVHVBGHGLDMY-UHFFFAOYSA-N 6-chloro-4-N-[(2-methylpyridin-4-yl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=NC=C1)C)N ZCPVHVBGHGLDMY-UHFFFAOYSA-N 0.000 description 2
• TUVQTRGKVDPLDU-UHFFFAOYSA-N 6-chloro-4-N-[(3,4-dichlorophenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)Cl)Cl)N TUVQTRGKVDPLDU-UHFFFAOYSA-N 0.000 description 2
• LSGHMFVUOHSPAY-UHFFFAOYSA-N 6-chloro-4-N-[(3,4-difluorophenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)F)F)N LSGHMFVUOHSPAY-UHFFFAOYSA-N 0.000 description 2
• CIONPFPQYXHPEX-UHFFFAOYSA-N 6-chloro-4-N-[(3-chlorophenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=CC=C1)Cl)N CIONPFPQYXHPEX-UHFFFAOYSA-N 0.000 description 2
• POOOKUXMUVRWEZ-UHFFFAOYSA-N 6-chloro-4-N-[(4-chloro-3-methylphenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)Cl)C)N POOOKUXMUVRWEZ-UHFFFAOYSA-N 0.000 description 2
• QZDNOLMTPVUQHZ-UHFFFAOYSA-N 6-chloro-4-N-[(4-fluorophenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)F)N QZDNOLMTPVUQHZ-UHFFFAOYSA-N 0.000 description 2
• FXCLRQAKICJUSM-UHFFFAOYSA-N 6-chloro-N-[(2-methylpyrimidin-5-yl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC=1C=NC(=NC=1)C)[N+](=O)[O-] FXCLRQAKICJUSM-UHFFFAOYSA-N 0.000 description 2
• FDLQLLZNIHGIRR-UHFFFAOYSA-N 6-chloro-N-[(3,4-dichlorophenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)Cl)Cl)[N+](=O)[O-] FDLQLLZNIHGIRR-UHFFFAOYSA-N 0.000 description 2
• DPQXAZCRPOKENP-UHFFFAOYSA-N 6-chloro-N-[(3-chloro-4-methylphenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)C)Cl)[N+](=O)[O-] DPQXAZCRPOKENP-UHFFFAOYSA-N 0.000 description 2
• WOQFKWOLHQNZSN-UHFFFAOYSA-N 6-chloro-N-[(4-chloro-3-methylphenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)Cl)C)[N+](=O)[O-] WOQFKWOLHQNZSN-UHFFFAOYSA-N 0.000 description 2
• CQVGRZRTSHHQAQ-UHFFFAOYSA-N 6-chloro-N-[(4-fluorophenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)F)[N+](=O)[O-] CQVGRZRTSHHQAQ-UHFFFAOYSA-N 0.000 description 2
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
• YMCQCKIZSFHFFM-UHFFFAOYSA-N 9-[(3-chlorophenyl)methyl]-6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC=1C=C(C=CC=1)CN1C2=NC(=NC(=C2NC1=O)NCC1=CC=C(C=C1)OC)SCCC YMCQCKIZSFHFFM-UHFFFAOYSA-N 0.000 description 2
• LASYSHUXPGRDMN-UHFFFAOYSA-N 9-[(4-bromophenyl)methyl]-6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-7H-purin-8-one Chemical compound BrC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NCC1=CC=C(C=C1)OC)SCCC LASYSHUXPGRDMN-UHFFFAOYSA-N 0.000 description 2
• WOUHLAXHUODHMZ-UHFFFAOYSA-N 9-[(4-fluorophenyl)methyl]-6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-7H-purin-8-one Chemical compound FC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NCC1=CC=C(C=C1)OC)SCCC WOUHLAXHUODHMZ-UHFFFAOYSA-N 0.000 description 2
• OWUFMTCUOJNOCA-UHFFFAOYSA-N 9-benzyl-6-(propylamino)-2-propylsulfinyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NCCC)S(=O)CCC OWUFMTCUOJNOCA-UHFFFAOYSA-N 0.000 description 2
• STYMBJDEOUPVSU-UHFFFAOYSA-N 9-benzyl-6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NCC1=CC=C(C=C1)OC)SCCC STYMBJDEOUPVSU-UHFFFAOYSA-N 0.000 description 2
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
• 229920001817 Agar Polymers 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
• ZXPHAVCZTBGHCJ-UHFFFAOYSA-N CCCC(CCC)CNC1=C2C(=NC(=N1)SCCC)N(C(=O)N2)CC3=CC=CC=C3 Chemical class CCCC(CCC)CNC1=C2C(=NC(=N1)SCCC)N(C(=O)N2)CC3=CC=CC=C3 ZXPHAVCZTBGHCJ-UHFFFAOYSA-N 0.000 description 2
• IYZZWMCSHFSKJC-UHFFFAOYSA-N CCCS(c(nc1N)nc(N2Cc(cc3)cc(C)c3Cl)c1NC2=O)(=N)=O Chemical compound CCCS(c(nc1N)nc(N2Cc(cc3)cc(C)c3Cl)c1NC2=O)(=N)=O IYZZWMCSHFSKJC-UHFFFAOYSA-N 0.000 description 2
• BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 2
• GDAADULAJPQRNE-UHFFFAOYSA-N CCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1F)C2=O)(=O)=O Chemical compound CCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC=C1F)C2=O)(=O)=O GDAADULAJPQRNE-UHFFFAOYSA-N 0.000 description 2
• 206010048610 Cardiotoxicity Diseases 0.000 description 2
• 229940126639 Compound 33 Drugs 0.000 description 2
• 102000004328 Cytochrome P-450 CYP3A Human genes 0.000 description 2
• 108010081668 Cytochrome P-450 CYP3A Proteins 0.000 description 2
• 102000004127 Cytokines Human genes 0.000 description 2
• RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• 102000004190 Enzymes Human genes 0.000 description 2
• 108090000790 Enzymes Proteins 0.000 description 2
• 101100501444 Escherichia phage P1 17 gene Proteins 0.000 description 2
• 101710142246 External core antigen Proteins 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 2
• 229930182566 Gentamicin Natural products 0.000 description 2
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 239000007821 HATU Substances 0.000 description 2
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• 102000007576 Interferon Regulatory Factor-7 Human genes 0.000 description 2
• 108010032036 Interferon Regulatory Factor-7 Proteins 0.000 description 2
• 102100026720 Interferon beta Human genes 0.000 description 2
• 108090000467 Interferon-beta Proteins 0.000 description 2
• 108010063738 Interleukins Proteins 0.000 description 2
• 102000015696 Interleukins Human genes 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 102000010168 Myeloid Differentiation Factor 88 Human genes 0.000 description 2
• 108010077432 Myeloid Differentiation Factor 88 Proteins 0.000 description 2
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
• TWTXTWSFXYSAGO-UHFFFAOYSA-N N-[(4-bromophenyl)methyl]-6-chloro-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC=C(C=C1)Br)[N+](=O)[O-] TWTXTWSFXYSAGO-UHFFFAOYSA-N 0.000 description 2
• USMWWQSLSNFTDU-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-propylsulfanyl-7H-purin-6-yl]-2-methylbutanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(CC)C)=O)SCCC USMWWQSLSNFTDU-UHFFFAOYSA-N 0.000 description 2
• QAADZYUXQLUXFX-UHFFFAOYSA-N N-phenylmethylthioformamide Natural products S=CNCC1=CC=CC=C1 QAADZYUXQLUXFX-UHFFFAOYSA-N 0.000 description 2
• 229930193140 Neomycin Natural products 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
• 108700008625 Reporter Genes Proteins 0.000 description 2
• PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 229940124614 TLR 8 agonist Drugs 0.000 description 2
• 108010060825 Toll-Like Receptor 7 Proteins 0.000 description 2
• 102000008236 Toll-Like Receptor 7 Human genes 0.000 description 2
• 208000018452 Torsade de pointes Diseases 0.000 description 2
• 208000002363 Torsades de Pointes Diseases 0.000 description 2
• 102000040945 Transcription factor Human genes 0.000 description 2
• 108091023040 Transcription factor Proteins 0.000 description 2
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
• SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 2
• 238000002835 absorbance Methods 0.000 description 2
• 102000035181 adaptor proteins Human genes 0.000 description 2
• 108091005764 adaptor proteins Proteins 0.000 description 2
• 230000002411 adverse Effects 0.000 description 2
• 239000008272 agar Substances 0.000 description 2
• 150000001350 alkyl halides Chemical class 0.000 description 2
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
• 239000012491 analyte Substances 0.000 description 2
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
• 238000013459 approach Methods 0.000 description 2
• 125000003118 aryl group Chemical group 0.000 description 2
• 210000003719 b-lymphocyte Anatomy 0.000 description 2
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 125000002619 bicyclic group Chemical group 0.000 description 2
• 230000004071 biological effect Effects 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 239000007853 buffer solution Substances 0.000 description 2
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 231100000259 cardiotoxicity Toxicity 0.000 description 2
• 238000005119 centrifugation Methods 0.000 description 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
• 229940125877 compound 31 Drugs 0.000 description 2
• 239000000356 contaminant Substances 0.000 description 2
• 239000012228 culture supernatant Substances 0.000 description 2
• 125000006317 cyclopropyl amino group Chemical group 0.000 description 2
• 230000001086 cytosolic effect Effects 0.000 description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 239000012091 fetal bovine serum Substances 0.000 description 2
• 235000003599 food sweetener Nutrition 0.000 description 2
• 229960002518 gentamicin Drugs 0.000 description 2
• 239000008103 glucose Substances 0.000 description 2
• 235000013922 glutamic acid Nutrition 0.000 description 2
• 239000004220 glutamic acid Substances 0.000 description 2
• KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
• 229940093915 gynecological organic acid Drugs 0.000 description 2
• 230000036541 health Effects 0.000 description 2
• 210000003494 hepatocyte Anatomy 0.000 description 2
• 102000045715 human TLR7 Human genes 0.000 description 2
• 102000045720 human TLR8 Human genes 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 2
• 230000001976 improved effect Effects 0.000 description 2
• 230000015788 innate immune response Effects 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• 239000000543 intermediate Substances 0.000 description 2
• 238000007912 intraperitoneal administration Methods 0.000 description 2
• 150000002513 isocyanates Chemical class 0.000 description 2
• 239000004310 lactic acid Substances 0.000 description 2
• 235000014655 lactic acid Nutrition 0.000 description 2
• 239000010410 layer Substances 0.000 description 2
• 238000010841 mRNA extraction Methods 0.000 description 2
• 229910001629 magnesium chloride Inorganic materials 0.000 description 2
• 235000019359 magnesium stearate Nutrition 0.000 description 2
• 239000001630 malic acid Substances 0.000 description 2
• 235000011090 malic acid Nutrition 0.000 description 2
• 210000001161 mammalian embryo Anatomy 0.000 description 2
• IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
• 230000004060 metabolic process Effects 0.000 description 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
• 230000003228 microsomal effect Effects 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 238000012544 monitoring process Methods 0.000 description 2
• 231100000219 mutagenic Toxicity 0.000 description 2
• 230000003505 mutagenic effect Effects 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 2
• LVBWRNKEBGYENR-UHFFFAOYSA-N n-cyclopropyl-4-[8-(oxan-4-ylmethylamino)-6-[(1,1,1-trifluoro-2-methylpropan-2-yl)amino]imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C12=NC=C(C=3C=CC(=CC=3)C(=O)NC3CC3)N2N=C(NC(C)(C)C(F)(F)F)C=C1NCC1CCOCC1 LVBWRNKEBGYENR-UHFFFAOYSA-N 0.000 description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 229960004927 neomycin Drugs 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• 229960000381 omeprazole Drugs 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 239000012074 organic phase Substances 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• 244000052769 pathogen Species 0.000 description 2
• HLEKYJVHEBHTMR-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O.CCCCC(N)=O HLEKYJVHEBHTMR-UHFFFAOYSA-N 0.000 description 2
• 239000000825 pharmaceutical preparation Substances 0.000 description 2
• 239000012071 phase Substances 0.000 description 2
• DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
• 229960002695 phenobarbital Drugs 0.000 description 2
• 230000000704 physical effect Effects 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 239000008057 potassium phosphate buffer Substances 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 239000002243 precursor Substances 0.000 description 2
• 238000012545 processing Methods 0.000 description 2
• 125000006308 propyl amino group Chemical group 0.000 description 2
• 235000018102 proteins Nutrition 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
• 239000000376 reactant Substances 0.000 description 2
• 230000009257 reactivity Effects 0.000 description 2
• 230000008929 regeneration Effects 0.000 description 2
• 238000011069 regeneration method Methods 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 238000012216 screening Methods 0.000 description 2
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
• 238000013207 serial dilution Methods 0.000 description 2
• 150000003384 small molecules Chemical class 0.000 description 2
• 239000007921 spray Substances 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• 239000003765 sweetening agent Substances 0.000 description 2
• 208000024891 symptom Diseases 0.000 description 2
• 230000009885 systemic effect Effects 0.000 description 2
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
• 125000001302 tertiary amino group Chemical group 0.000 description 2
• YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
• 230000000699 topical effect Effects 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 2
• OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 description 2
• ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-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
• GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
• IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 1
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
• VMNXLLDFGVEBLE-UHFFFAOYSA-N (4-methylsulfonylphenyl)methanamine Chemical compound CS(=O)(=O)C1=CC=C(CN)C=C1 VMNXLLDFGVEBLE-UHFFFAOYSA-N 0.000 description 1
• XPARFBOWIYMLMY-UHFFFAOYSA-N (6-chloropyridin-3-yl)methanamine Chemical compound NCC1=CC=C(Cl)N=C1 XPARFBOWIYMLMY-UHFFFAOYSA-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
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• RKOUFQLNMRAACI-UHFFFAOYSA-N 1,1,1-trifluoro-2-iodoethane Chemical compound FC(F)(F)CI RKOUFQLNMRAACI-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
• QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 1
• YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
• CEVMYGZHEJSOHZ-UHFFFAOYSA-N 1-bromo-3-methoxypropane Chemical compound COCCCBr CEVMYGZHEJSOHZ-UHFFFAOYSA-N 0.000 description 1
• MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
• VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
• RPGDVPAENGWKAO-UHFFFAOYSA-N 2,4-difluoro-n-methylaniline Chemical compound CNC1=CC=C(F)C=C1F RPGDVPAENGWKAO-UHFFFAOYSA-N 0.000 description 1
• FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
• WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
• MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
• QRXBTPFMCTXCRD-UHFFFAOYSA-N 2-chloropyridine-4-carbonitrile Chemical compound ClC1=CC(C#N)=CC=N1 QRXBTPFMCTXCRD-UHFFFAOYSA-N 0.000 description 1
• BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
• 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
• YCURDTPXHPXCKH-UHFFFAOYSA-N 2-ethylbutanoyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OC(=O)C(CC)CC YCURDTPXHPXCKH-UHFFFAOYSA-N 0.000 description 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• WRTPVONNQPWNRH-UHFFFAOYSA-N 2-methylbutanoyl 2-methylbutanoate Chemical compound CCC(C)C(=O)OC(=O)C(C)CC WRTPVONNQPWNRH-UHFFFAOYSA-N 0.000 description 1
• WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
• DXKLAQMZDYZMFM-UHFFFAOYSA-N 2-sulfanylidene-7,9-dihydro-3h-purin-8-one Chemical compound C1=NC(=S)NC2=C1NC(=O)N2 DXKLAQMZDYZMFM-UHFFFAOYSA-N 0.000 description 1
• SULGSLUIIZBEEN-UHFFFAOYSA-N 3,4-difluoro-n-methylaniline Chemical compound CNC1=CC=C(F)C(F)=C1 SULGSLUIIZBEEN-UHFFFAOYSA-N 0.000 description 1
• XFKPORAVEUOIRF-UHFFFAOYSA-N 3-(aminomethyl)benzonitrile Chemical compound NCC1=CC=CC(C#N)=C1 XFKPORAVEUOIRF-UHFFFAOYSA-N 0.000 description 1
• ODZCKFNCAFHXRG-UHFFFAOYSA-N 3-[(6-amino-8-oxo-2-propylsulfanyl-7H-purin-9-yl)methyl]benzonitrile Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC=1C=C(C#N)C=CC=1)=O ODZCKFNCAFHXRG-UHFFFAOYSA-N 0.000 description 1
• UTOQNBVFPWFMNZ-UHFFFAOYSA-N 3-[(6-chloro-2-methylsulfanyl-8-oxo-7H-purin-9-yl)methyl]benzonitrile Chemical compound ClC1=C2NC(N(C2=NC(=N1)SC)CC=1C=C(C#N)C=CC=1)=O UTOQNBVFPWFMNZ-UHFFFAOYSA-N 0.000 description 1
• WSFZCPSHUKUTFD-UHFFFAOYSA-N 3-[(6-chloro-8-oxo-2-propylsulfanyl-7H-purin-9-yl)methyl]benzonitrile Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC=1C=C(C#N)C=CC=1)=O WSFZCPSHUKUTFD-UHFFFAOYSA-N 0.000 description 1
• GRUPMMBRLDBTDD-UHFFFAOYSA-N 3-[2-(2-methyl-1,3-thiazol-4-yl)ethynyl]benzonitrile Chemical compound S1C(C)=NC(C#CC=2C=C(C=CC=2)C#N)=C1 GRUPMMBRLDBTDD-UHFFFAOYSA-N 0.000 description 1
• IWPOXJOSPLPXLN-UHFFFAOYSA-N 3-[[(5-amino-6-chloro-2-methylsulfanylpyrimidin-4-yl)amino]methyl]benzonitrile Chemical compound NC=1C(=NC(=NC=1Cl)SC)NCC=1C=C(C#N)C=CC=1 IWPOXJOSPLPXLN-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• UFBWOBPUOXILAT-UHFFFAOYSA-N 3-chloro-4-methylbenzamide Chemical compound CC1=CC=C(C(N)=O)C=C1Cl UFBWOBPUOXILAT-UHFFFAOYSA-N 0.000 description 1
• JDGUVFZDTYKQJS-UHFFFAOYSA-N 3-chloro-n,4-dimethylaniline Chemical compound CNC1=CC=C(C)C(Cl)=C1 JDGUVFZDTYKQJS-UHFFFAOYSA-N 0.000 description 1
• WFGYSQDPURFIFL-UHFFFAOYSA-N 3-chloro-n-methylaniline Chemical compound CNC1=CC=CC(Cl)=C1 WFGYSQDPURFIFL-UHFFFAOYSA-N 0.000 description 1
• LFIWXXXFJFOECP-UHFFFAOYSA-N 4-(aminomethyl)benzonitrile Chemical compound NCC1=CC=C(C#N)C=C1 LFIWXXXFJFOECP-UHFFFAOYSA-N 0.000 description 1
• DNCQUWBSWUTJPX-UHFFFAOYSA-N 4-N-benzyl-6-chloro-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound C(C1=CC=CC=C1)NC1=NC(=NC(=C1N)Cl)SCCC DNCQUWBSWUTJPX-UHFFFAOYSA-N 0.000 description 1
• GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 description 1
• ZMXIMWNANZYPQP-UHFFFAOYSA-N 4-[[6-[(4-methoxyphenyl)methylamino]-8-oxo-2-propylsulfanyl-7H-purin-9-yl]methyl]benzonitrile Chemical compound COC1=CC=C(C=C1)CNC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C#N)C=C1)=O ZMXIMWNANZYPQP-UHFFFAOYSA-N 0.000 description 1
• VFRQJCXMZAJFNM-UHFFFAOYSA-N 4-amino-3-[(4-methylphenyl)methyl]-2-oxo-1h-imidazole-5-carbonitrile Chemical compound C1=CC(C)=CC=C1CN1C(=O)NC(C#N)=C1N VFRQJCXMZAJFNM-UHFFFAOYSA-N 0.000 description 1
• AYVPVDWQZAAZCM-UHFFFAOYSA-N 4-bromo-n-methylaniline Chemical compound CNC1=CC=C(Br)C=C1 AYVPVDWQZAAZCM-UHFFFAOYSA-N 0.000 description 1
• NHWTUJPCXDRQNF-UHFFFAOYSA-N 4-chloro-3-methylbenzamide Chemical compound CC1=CC(C(N)=O)=CC=C1Cl NHWTUJPCXDRQNF-UHFFFAOYSA-N 0.000 description 1
• MRUKIIWRMSYKML-UHFFFAOYSA-N 4-chloro-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1Cl MRUKIIWRMSYKML-UHFFFAOYSA-N 0.000 description 1
• MMZMROHDQCJAJT-UHFFFAOYSA-N 4-chloro-4-oxobutanoic acid Chemical compound OC(=O)CCC(Cl)=O MMZMROHDQCJAJT-UHFFFAOYSA-N 0.000 description 1
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
• JHJXDGMATBLARH-UHFFFAOYSA-N 6-(ethylamino)-9-[(6-methylpyridin-3-yl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound C(C)NC1=C2NC(N(C2=NC(=N1)SCCC)CC=1C=NC(=CC=1)C)=O JHJXDGMATBLARH-UHFFFAOYSA-N 0.000 description 1
• NMXGUZXVUKGKIR-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylamino]-2-methylsulfanyl-9-(pyridin-4-ylmethyl)-7H-purin-8-one Chemical compound COC1=CC=C(C=C1)CNC1=C2NC(N(C2=NC(=N1)SC)CC1=CC=NC=C1)=O NMXGUZXVUKGKIR-UHFFFAOYSA-N 0.000 description 1
• OSGAFGPHWBCQFX-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-9-[[4-(trifluoromethyl)phenyl]methyl]-7H-purin-8-one Chemical compound COC1=CC=C(C=C1)CNC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)C(F)(F)F)=O OSGAFGPHWBCQFX-UHFFFAOYSA-N 0.000 description 1
• UIBHXZITWIPTPT-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylamino]-2-propylsulfinyl-9-(pyrimidin-5-ylmethyl)-7H-purin-8-one Chemical compound COC1=CC=C(C=C1)CNC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC=1C=NC=NC=1)=O UIBHXZITWIPTPT-UHFFFAOYSA-N 0.000 description 1
• JNOVZHIANGOQTM-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylamino]-7-(2-methylpropyl)-2-propylsulfanyl-9H-purin-8-one Chemical compound C(C(C)C)N1C(NC2=NC(=NC(=C12)NCC1=CC=C(C=C1)OC)SCCC)=O JNOVZHIANGOQTM-UHFFFAOYSA-N 0.000 description 1
• XKRVQTQQYGDWKO-UHFFFAOYSA-N 6-[(4-methoxyphenyl)methylamino]-9-[(4-methylsulfonylphenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound COC1=CC=C(C=C1)CNC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)S(=O)(=O)C)=O XKRVQTQQYGDWKO-UHFFFAOYSA-N 0.000 description 1
• QGZQLFVPRLVEJR-UHFFFAOYSA-N 6-[(4-methylphenyl)methyl]-5-nitro-2-propylsulfanylpyrimidin-4-amine Chemical compound C1(=CC=C(C=C1)CC1=C(C(=NC(=N1)SCCC)N)[N+](=O)[O-])C QGZQLFVPRLVEJR-UHFFFAOYSA-N 0.000 description 1
• LHRSFBRLPAJSMK-UHFFFAOYSA-N 6-amino-2-ethylsulfanyl-9-[(4-methylphenyl)methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCC)CC1=CC=C(C=C1)C)=O LHRSFBRLPAJSMK-UHFFFAOYSA-N 0.000 description 1
• KAPQRBANZCFAFB-UHFFFAOYSA-N 6-amino-2-ethylsulfinyl-9-[(4-fluorophenyl)methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CC)CC1=CC=C(C=C1)F)=O KAPQRBANZCFAFB-UHFFFAOYSA-N 0.000 description 1
• IXERKOMQMNLWAX-UHFFFAOYSA-N 6-amino-2-ethylsulfinyl-9-[(4-methylphenyl)methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CC)CC1=CC=C(C=C1)C)=O IXERKOMQMNLWAX-UHFFFAOYSA-N 0.000 description 1
• OWHOVQKHZCNMAL-UHFFFAOYSA-N 6-amino-2-methylsulfanyl-9-(pyridin-3-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SC)CC=1C=NC=CC=1)=O OWHOVQKHZCNMAL-UHFFFAOYSA-N 0.000 description 1
• XQIXBJPSZOOHPE-UHFFFAOYSA-N 6-amino-2-methylsulfinyl-9-(pyridin-4-ylmethyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)C)CC1=CC=NC=C1)=O XQIXBJPSZOOHPE-UHFFFAOYSA-N 0.000 description 1
• FWOGSCODNNTDOW-UHFFFAOYSA-N 6-amino-2-propylsulfanyl-9-[[4-(trifluoromethyl)phenyl]methyl]-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)C(F)(F)F)=O FWOGSCODNNTDOW-UHFFFAOYSA-N 0.000 description 1
• COTFBCNBTRCHOI-UHFFFAOYSA-N 6-amino-9-(2-methylpropyl)-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC(C)C)=O COTFBCNBTRCHOI-UHFFFAOYSA-N 0.000 description 1
• AABAIKFHSWQIFO-UHFFFAOYSA-N 6-amino-9-(3,4-dichlorophenyl)-2-propylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)C1=CC(=C(C=C1)Cl)Cl)=O AABAIKFHSWQIFO-UHFFFAOYSA-N 0.000 description 1
• REAXDVUVMGLJJT-UHFFFAOYSA-N 6-amino-9-[(2,4-difluorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=C(C=C(C=C1)F)F)=O REAXDVUVMGLJJT-UHFFFAOYSA-N 0.000 description 1
• JYEGCOQQEWQOMI-UHFFFAOYSA-N 6-amino-9-[(2,4-difluorophenyl)methyl]-2-propylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=C(C=C(C=C1)F)F)=O JYEGCOQQEWQOMI-UHFFFAOYSA-N 0.000 description 1
• AKYNQXFQVZXKTE-UHFFFAOYSA-N 6-amino-9-[(2-methylpyridin-4-yl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=NC=C1)C)=O AKYNQXFQVZXKTE-UHFFFAOYSA-N 0.000 description 1
• CMOPSXCJQWZWNI-UHFFFAOYSA-N 6-amino-9-[(3,4-dichlorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)Cl)Cl)=O CMOPSXCJQWZWNI-UHFFFAOYSA-N 0.000 description 1
• WBFUQOPVMJQIAL-UHFFFAOYSA-N 6-amino-9-[(3,4-dichlorophenyl)methyl]-2-propylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=CC(=C(C=C1)Cl)Cl)=O WBFUQOPVMJQIAL-UHFFFAOYSA-N 0.000 description 1
• AWMRXUUYVORZPB-UHFFFAOYSA-N 6-amino-9-[(3,4-difluorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)F)F)=O AWMRXUUYVORZPB-UHFFFAOYSA-N 0.000 description 1
• HMWSWNCISULJJJ-UHFFFAOYSA-N 6-amino-9-[(3-chloro-4-methylphenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)C)Cl)=O HMWSWNCISULJJJ-UHFFFAOYSA-N 0.000 description 1
• NXUYFJDQVXISPX-UHFFFAOYSA-N 6-amino-9-[(3-chlorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=CC=C1)Cl)=O NXUYFJDQVXISPX-UHFFFAOYSA-N 0.000 description 1
• YEOAWWOBFYFPBW-UHFFFAOYSA-N 6-amino-9-[(4-bromophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)Br)=O YEOAWWOBFYFPBW-UHFFFAOYSA-N 0.000 description 1
• SKXREALOLSMPMS-UHFFFAOYSA-N 6-amino-9-[(4-bromophenyl)methyl]-2-propylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCC)CC1=CC=C(C=C1)Br)=O SKXREALOLSMPMS-UHFFFAOYSA-N 0.000 description 1
• SITQWHVVXNSHSG-UHFFFAOYSA-N 6-amino-9-[(4-chloro-3-fluorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)Cl)F)=O SITQWHVVXNSHSG-UHFFFAOYSA-N 0.000 description 1
• LCZPJVDNHFISPW-UHFFFAOYSA-N 6-amino-9-[(4-chloro-3-methylphenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)Cl)C)=O LCZPJVDNHFISPW-UHFFFAOYSA-N 0.000 description 1
• JAOGLXMHMAGPSB-UHFFFAOYSA-N 6-amino-9-[(4-chlorophenyl)methyl]-2-ethylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CC)CC1=CC=C(C=C1)Cl)=O JAOGLXMHMAGPSB-UHFFFAOYSA-N 0.000 description 1
• AEVQYQZGVSLRES-UHFFFAOYSA-N 6-amino-9-[(4-chlorophenyl)methyl]-2-methylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SC)CC1=CC=C(C=C1)Cl)=O AEVQYQZGVSLRES-UHFFFAOYSA-N 0.000 description 1
• NBHMULUYJAUPGF-UHFFFAOYSA-N 6-amino-9-[(4-fluorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)F)=O NBHMULUYJAUPGF-UHFFFAOYSA-N 0.000 description 1
• FXQAYXPLOMMSDA-UHFFFAOYSA-N 6-amino-9-[(4-fluorophenyl)methyl]-2-sulfanylidene-1,7-dihydropurin-8-one Chemical compound OC1=NC=2C(N)=NC(S)=NC=2N1CC1=CC=C(F)C=C1 FXQAYXPLOMMSDA-UHFFFAOYSA-N 0.000 description 1
• FLASPAQGZOEWHF-UHFFFAOYSA-N 6-amino-9-[(4-methoxyphenyl)methyl]-2-methylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SC)CC1=CC=C(C=C1)OC)=O FLASPAQGZOEWHF-UHFFFAOYSA-N 0.000 description 1
• KIHSDTHJQITPOC-UHFFFAOYSA-N 6-amino-9-[(4-methoxyphenyl)methyl]-2-sulfanylidene-1,7-dihydropurin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S)CC1=CC=C(C=C1)OC)=O KIHSDTHJQITPOC-UHFFFAOYSA-N 0.000 description 1
• PPVXJMYJMODOPW-UHFFFAOYSA-N 6-amino-9-[(4-methylphenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)C)=O PPVXJMYJMODOPW-UHFFFAOYSA-N 0.000 description 1
• WFPGKBGNSQAKOR-UHFFFAOYSA-N 6-amino-9-[(4-methylphenyl)methyl]-2-sulfanylidene-1,7-dihydropurin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S)CC1=CC=C(C=C1)C)=O WFPGKBGNSQAKOR-UHFFFAOYSA-N 0.000 description 1
• CDHYXPUAMUVANH-UHFFFAOYSA-N 6-amino-9-[(4-methylsulfonylphenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)S(=O)(=O)C)=O CDHYXPUAMUVANH-UHFFFAOYSA-N 0.000 description 1
• QMUUHLBGKXHOMV-UHFFFAOYSA-N 6-amino-9-[(6-chloropyridin-3-yl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC=1C=NC(=CC=1)Cl)=O QMUUHLBGKXHOMV-UHFFFAOYSA-N 0.000 description 1
• XTYSOULVGVCCTL-UHFFFAOYSA-N 6-amino-9-[(6-methylpyridin-3-yl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCC)CC=1C=NC(=CC=1)C)=O XTYSOULVGVCCTL-UHFFFAOYSA-N 0.000 description 1
• FDLPDJHVEKXWLI-UHFFFAOYSA-N 6-amino-9-benzyl-2-(2,2,2-trifluoroethylsulfinyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CC(F)(F)F)CC1=CC=CC=C1)=O FDLPDJHVEKXWLI-UHFFFAOYSA-N 0.000 description 1
• BYCVOHQIYWOEQU-UHFFFAOYSA-N 6-amino-9-benzyl-2-(3-methoxypropylsulfanyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)SCCCOC)CC1=CC=CC=C1)=O BYCVOHQIYWOEQU-UHFFFAOYSA-N 0.000 description 1
• XDLSAEMIECHJEI-UHFFFAOYSA-N 6-amino-9-benzyl-2-(3-methoxypropylsulfinyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CCCOC)CC1=CC=CC=C1)=O XDLSAEMIECHJEI-UHFFFAOYSA-N 0.000 description 1
• FGGHMITXKSUZKF-UHFFFAOYSA-N 6-amino-9-benzyl-2-(cyclohexylmethylsulfanyl)-7h-purin-8-one Chemical compound N=1C=2N(CC=3C=CC=CC=3)C(O)=NC=2C(N)=NC=1SCC1CCCCC1 FGGHMITXKSUZKF-UHFFFAOYSA-N 0.000 description 1
• DFPKSCBPNVPRIY-UHFFFAOYSA-N 6-amino-9-benzyl-2-(cyclohexylmethylsulfinyl)-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)CC1CCCCC1)CC1=CC=CC=C1)=O DFPKSCBPNVPRIY-UHFFFAOYSA-N 0.000 description 1
• HONIKIYFGCHQSJ-UHFFFAOYSA-N 6-amino-9-benzyl-2-methylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)C)CC1=CC=CC=C1)=O HONIKIYFGCHQSJ-UHFFFAOYSA-N 0.000 description 1
• XJZJHVOQISEZRS-UHFFFAOYSA-N 6-amino-9-benzyl-2-propan-2-ylsulfanyl-7h-purin-8-one Chemical compound C12=NC(SC(C)C)=NC(N)=C2N=C(O)N1CC1=CC=CC=C1 XJZJHVOQISEZRS-UHFFFAOYSA-N 0.000 description 1
• RVOTWKKVMSPCLK-UHFFFAOYSA-N 6-amino-9-benzyl-2-propan-2-ylsulfinyl-7H-purin-8-one Chemical compound NC1=C2NC(N(C2=NC(=N1)S(=O)C(C)C)CC1=CC=CC=C1)=O RVOTWKKVMSPCLK-UHFFFAOYSA-N 0.000 description 1
• YVHWMATXRMXZJI-UHFFFAOYSA-N 6-amino-9-benzyl-2-sulfanylidene-1,7-dihydropurin-8-one Chemical compound OC1=NC=2C(N)=NC(S)=NC=2N1CC1=CC=CC=C1 YVHWMATXRMXZJI-UHFFFAOYSA-N 0.000 description 1
• LJGIPYPDOABDLJ-UHFFFAOYSA-N 6-chloro-2-methylsulfanyl-9-(pyridin-3-ylmethyl)-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SC)CC=1C=NC=CC=1)=O LJGIPYPDOABDLJ-UHFFFAOYSA-N 0.000 description 1
• WRAPBXXZFBVXPB-UHFFFAOYSA-N 6-chloro-2-propylsulfanyl-9-(pyrimidin-5-ylmethyl)-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC=1C=NC=NC=1)=O WRAPBXXZFBVXPB-UHFFFAOYSA-N 0.000 description 1
• WLQUEKUHGFEFBK-UHFFFAOYSA-N 6-chloro-2-propylsulfanyl-9-[[4-(trifluoromethyl)phenyl]methyl]-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)C(F)(F)F)=O WLQUEKUHGFEFBK-UHFFFAOYSA-N 0.000 description 1
• RBZBVXCLOKTTQT-UHFFFAOYSA-N 6-chloro-4-N-[(4-chloro-3-fluorophenyl)methyl]-2-propylsulfanylpyrimidine-4,5-diamine Chemical compound ClC1=C(C(=NC(=N1)SCCC)NCC1=CC(=C(C=C1)Cl)F)N RBZBVXCLOKTTQT-UHFFFAOYSA-N 0.000 description 1
• VMRLPDGYMSGDAJ-UHFFFAOYSA-N 6-chloro-9-[(2,4-difluorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=C(C=C(C=C1)F)F)=O VMRLPDGYMSGDAJ-UHFFFAOYSA-N 0.000 description 1
• GNMOFFHKLDZUBH-UHFFFAOYSA-N 6-chloro-9-[(2-chlorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=C(C=CC=C1)Cl)=O GNMOFFHKLDZUBH-UHFFFAOYSA-N 0.000 description 1
• VHLMRZXQXOAKFV-UHFFFAOYSA-N 6-chloro-9-[(2-methylpyridin-4-yl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=NC=C1)C)=O VHLMRZXQXOAKFV-UHFFFAOYSA-N 0.000 description 1
• ADSPKPCBBNTTHA-UHFFFAOYSA-N 6-chloro-9-[(2-methylpyrimidin-5-yl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC=1C=NC(=NC=1)C)=O ADSPKPCBBNTTHA-UHFFFAOYSA-N 0.000 description 1
• ICHLHUJTUCTZOV-UHFFFAOYSA-N 6-chloro-9-[(3,4-dichlorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)Cl)Cl)=O ICHLHUJTUCTZOV-UHFFFAOYSA-N 0.000 description 1
• BCVOPHQQQAQPJC-UHFFFAOYSA-N 6-chloro-9-[(3,4-difluorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)F)F)=O BCVOPHQQQAQPJC-UHFFFAOYSA-N 0.000 description 1
• BCCIMILKWSTHDD-UHFFFAOYSA-N 6-chloro-9-[(3-chloro-4-methylphenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)C)Cl)=O BCCIMILKWSTHDD-UHFFFAOYSA-N 0.000 description 1
• FELAQEZHOPNTLG-UHFFFAOYSA-N 6-chloro-9-[(3-chlorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=CC=C1)Cl)=O FELAQEZHOPNTLG-UHFFFAOYSA-N 0.000 description 1
• RSSUZYSUKRLKJD-UHFFFAOYSA-N 6-chloro-9-[(4-chloro-3-fluorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC(=C(C=C1)Cl)F)=O RSSUZYSUKRLKJD-UHFFFAOYSA-N 0.000 description 1
• JMVGWDKXXPHGBQ-UHFFFAOYSA-N 6-chloro-9-[(4-chlorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)Cl)=O JMVGWDKXXPHGBQ-UHFFFAOYSA-N 0.000 description 1
• AFWDOXBIZKOMKO-UHFFFAOYSA-N 6-chloro-9-[(4-fluorophenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)F)=O AFWDOXBIZKOMKO-UHFFFAOYSA-N 0.000 description 1
• CXIZBZRUTNLIFN-UHFFFAOYSA-N 6-chloro-9-[(4-methylsulfonylphenyl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)S(=O)(=O)C)=O CXIZBZRUTNLIFN-UHFFFAOYSA-N 0.000 description 1
• WNIFXTZUXYGFQT-UHFFFAOYSA-N 6-chloro-9-[(6-methylpyridin-3-yl)methyl]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC=1C=NC(=CC=1)C)=O WNIFXTZUXYGFQT-UHFFFAOYSA-N 0.000 description 1
• RZOKQIPOABEQAM-UHFFFAOYSA-N 6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=N1 RZOKQIPOABEQAM-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• LPWKFUVWWQYLOD-UHFFFAOYSA-N 9-(dimethylamino)-3-(4-methylphenyl)pyrido[2,3]thieno[2,4-d]pyrimidin-4-one Chemical compound C1=2C(N(C)C)=CN=CC=2SC(C2=O)=C1N=CN2C1=CC=C(C)C=C1 LPWKFUVWWQYLOD-UHFFFAOYSA-N 0.000 description 1
• XYUIZXKZMNNNJW-UHFFFAOYSA-N 9-[(2,4-difluorophenyl)methyl]-6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-7H-purin-8-one Chemical compound FC1=C(C=CC(=C1)F)CN1C2=NC(=NC(=C2NC1=O)NCC1=CC=C(C=C1)OC)SCCC XYUIZXKZMNNNJW-UHFFFAOYSA-N 0.000 description 1
• WDRZHACBPKYTLK-UHFFFAOYSA-N 9-[(2,4-difluorophenyl)methyl]-N-[(4-methoxyphenyl)methyl]-2-propylsulfanyl-7,8-dihydropurin-6-amine Chemical compound FC1=C(C=CC(=C1)F)CN1C2=NC(=NC(=C2NC1)NCC1=CC=C(C=C1)OC)SCCC WDRZHACBPKYTLK-UHFFFAOYSA-N 0.000 description 1
• LTHOHQUDPIEOKR-UHFFFAOYSA-N 9-[(3,4-dichlorophenyl)methyl]-6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC=1C=C(C=CC=1Cl)CN1C2=NC(=NC(=C2NC1=O)NCC1=CC=C(C=C1)OC)SCCC LTHOHQUDPIEOKR-UHFFFAOYSA-N 0.000 description 1
• ZHRKYMWXQJRXBI-UHFFFAOYSA-N 9-[(3,4-dichlorophenyl)methyl]-N-[(4-methoxyphenyl)methyl]-2-propylsulfanyl-7,8-dihydropurin-6-amine Chemical compound ClC=1C=C(C=CC=1Cl)CN1C2=NC(=NC(=C2NC1)NCC1=CC=C(C=C1)OC)SCCC ZHRKYMWXQJRXBI-UHFFFAOYSA-N 0.000 description 1
• KSNWHZKBCNEOCV-UHFFFAOYSA-N 9-[(3,4-difluorophenyl)methyl]-6-[(4-methoxyphenyl)methylamino]-2-propylsulfanyl-7H-purin-8-one Chemical compound FC=1C=C(C=CC=1F)CN1C2=NC(=NC(=C2NC1=O)NCC1=CC=C(C=C1)OC)SCCC KSNWHZKBCNEOCV-UHFFFAOYSA-N 0.000 description 1
• FUEBWLWAQRITDI-UHFFFAOYSA-N 9-[(3,4-difluorophenyl)methyl]-N-[(4-methoxyphenyl)methyl]-2-propylsulfanyl-7,8-dihydropurin-6-amine Chemical compound FC=1C=C(C=CC=1F)CN1C2=NC(=NC(=C2NC1)NCC1=CC=C(C=C1)OC)SCCC FUEBWLWAQRITDI-UHFFFAOYSA-N 0.000 description 1
• JUQMATGKETVMOU-UHFFFAOYSA-N 9-[(4-bromophenyl)methyl]-6-chloro-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=C2NC(N(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)Br)=O JUQMATGKETVMOU-UHFFFAOYSA-N 0.000 description 1
• MGHINPRYGWYVFO-UHFFFAOYSA-N 9-[(4-chlorophenyl)methyl]-6-(ethylamino)-2-propylsulfanyl-7H-purin-8-one Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NCC)SCCC MGHINPRYGWYVFO-UHFFFAOYSA-N 0.000 description 1
• IFWBZWHYVNRMMC-UHFFFAOYSA-N 9-benzyl-6-(cyclopropylamino)-2-propylsulfanyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NC1CC1)SCCC IFWBZWHYVNRMMC-UHFFFAOYSA-N 0.000 description 1
• GCKJISLYRYLNAR-UHFFFAOYSA-N 9-benzyl-6-(cyclopropylamino)-2-propylsulfinyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NC1CC1)S(=O)CCC GCKJISLYRYLNAR-UHFFFAOYSA-N 0.000 description 1
• ATJCVTPFAIOTFI-UHFFFAOYSA-N 9-benzyl-6-(ethylamino)-2-propylsulfanyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NCC)SCCC ATJCVTPFAIOTFI-UHFFFAOYSA-N 0.000 description 1
• TWWIKYSVNRCTOK-UHFFFAOYSA-N 9-benzyl-6-(ethylamino)-2-propylsulfinyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NCC)S(=O)CCC TWWIKYSVNRCTOK-UHFFFAOYSA-N 0.000 description 1
• BEACBILQFFTGQE-UHFFFAOYSA-N 9-benzyl-6-(propan-2-ylamino)-2-propylsulfanyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NC(C)C)SCCC BEACBILQFFTGQE-UHFFFAOYSA-N 0.000 description 1
• IRMPAYQHUIXYHY-UHFFFAOYSA-N 9-benzyl-6-(propan-2-ylamino)-2-propylsulfinyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NC(C)C)S(=O)CCC IRMPAYQHUIXYHY-UHFFFAOYSA-N 0.000 description 1
• HGNGKXBOLIGONP-UHFFFAOYSA-N 9-benzyl-6-(propylamino)-2-propylsulfanyl-7H-purin-8-one Chemical compound C(C1=CC=CC=C1)N1C2=NC(=NC(=C2NC1=O)NCCC)SCCC HGNGKXBOLIGONP-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 244000144725 Amygdalus communis Species 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• WCBGIQHHWPGCEI-UHFFFAOYSA-N C(CC)SC1=NC=C2NC(NC2=N1)=O Chemical compound C(CC)SC1=NC=C2NC(NC2=N1)=O WCBGIQHHWPGCEI-UHFFFAOYSA-N 0.000 description 1
• DZCVXMPHBCPMGY-UHFFFAOYSA-N C(CCC)(=O)O.O.C(CCC)(=O)O Chemical compound C(CCC)(=O)O.O.C(CCC)(=O)O DZCVXMPHBCPMGY-UHFFFAOYSA-N 0.000 description 1
• XMZDKNOVRKWWBN-UHFFFAOYSA-N CCCC(C)C(Nc(nc(nc1N2Cc(cc3)ccc3Cl)SCCC)c1NC2=O)=O Chemical compound CCCC(C)C(Nc(nc(nc1N2Cc(cc3)ccc3Cl)SCCC)c1NC2=O)=O XMZDKNOVRKWWBN-UHFFFAOYSA-N 0.000 description 1
• XJEVQCHAETXVIB-UHFFFAOYSA-N CCCCC(Nc(nc(nc1N2Cc3ccccc3)S(CCC)=O)c1NC2=O)=O Chemical compound CCCCC(Nc(nc(nc1N2Cc3ccccc3)S(CCC)=O)c1NC2=O)=O XJEVQCHAETXVIB-UHFFFAOYSA-N 0.000 description 1
• UBOWBPXWABHXOV-UHFFFAOYSA-N CCCNC(N=C(NS(CCC)(=O)=O)N=C1N2CC3=CC=CC=C3)=C1NC2=O Chemical compound CCCNC(N=C(NS(CCC)(=O)=O)N=C1N2CC3=CC=CC=C3)=C1NC2=O UBOWBPXWABHXOV-UHFFFAOYSA-N 0.000 description 1
• GBTUNBGAVAMIRX-UHFFFAOYSA-N CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC(F)=C1Cl)C2=O)(=O)=O Chemical compound CCCS(N=C(NC(N)=C1N2)N=C1N(CC(C=C1)=CC(F)=C1Cl)C2=O)(=O)=O GBTUNBGAVAMIRX-UHFFFAOYSA-N 0.000 description 1
• LSOLFDMQAGGOKO-UHFFFAOYSA-N CCCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC(Cl)=CC=C1)C2=O)(=O)=O Chemical compound CCCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC(Cl)=CC=C1)C2=O)(=O)=O LSOLFDMQAGGOKO-UHFFFAOYSA-N 0.000 description 1
• WGXYBJXUGPOTAP-UHFFFAOYSA-N CCCS(N=C(NC(NC1CC1)=C1N2)N=C1N(CC1=CC=CC=C1)C2=O)(=O)=O Chemical compound CCCS(N=C(NC(NC1CC1)=C1N2)N=C1N(CC1=CC=CC=C1)C2=O)(=O)=O WGXYBJXUGPOTAP-UHFFFAOYSA-N 0.000 description 1
• MBQBYGUMANOLRF-UHFFFAOYSA-N CCCS(c(nc1N2Cc(cc3)cc(Cl)c3Cl)nc(N)c1NC2=O)(=N)=O Chemical compound CCCS(c(nc1N2Cc(cc3)cc(Cl)c3Cl)nc(N)c1NC2=O)(=N)=O MBQBYGUMANOLRF-UHFFFAOYSA-N 0.000 description 1
• RXVPTJHAOBJTOO-UHFFFAOYSA-N CCCS(c(nc1N2Cc(cc3)cc(F)c3Cl)nc(N)c1NC2=O)(=N)=O Chemical compound CCCS(c(nc1N2Cc(cc3)cc(F)c3Cl)nc(N)c1NC2=O)(=N)=O RXVPTJHAOBJTOO-UHFFFAOYSA-N 0.000 description 1
• OEMOAEPBLIYKJT-UHFFFAOYSA-N CCCS(c(nc1N2Cc(cc3)cc(F)c3F)nc(N)c1NC2=O)=O Chemical compound CCCS(c(nc1N2Cc(cc3)cc(F)c3F)nc(N)c1NC2=O)=O OEMOAEPBLIYKJT-UHFFFAOYSA-N 0.000 description 1
• HJPNICYHBIWMIN-UHFFFAOYSA-N CCCS(c(nc1N2Cc3cc(Cl)c(C)cc3)nc(N)c1NC2=O)=O Chemical compound CCCS(c(nc1N2Cc3cc(Cl)c(C)cc3)nc(N)c1NC2=O)=O HJPNICYHBIWMIN-UHFFFAOYSA-N 0.000 description 1
• APBICSQRGKTYKB-UHFFFAOYSA-N CCCS(c(nc1N2Cc3ccc(C(F)(F)F)cc3)nc(N)c1NC2=O)(=N)=O Chemical compound CCCS(c(nc1N2Cc3ccc(C(F)(F)F)cc3)nc(N)c1NC2=O)(=N)=O APBICSQRGKTYKB-UHFFFAOYSA-N 0.000 description 1
• BQGJLGCRAYYVSZ-UHFFFAOYSA-N CCCS(c(nc1N2Cc3ccc(C)nc3)nc(N)c1NC2=O)(=N)=O Chemical compound CCCS(c(nc1N2Cc3ccc(C)nc3)nc(N)c1NC2=O)(=N)=O BQGJLGCRAYYVSZ-UHFFFAOYSA-N 0.000 description 1
• ZMNFFJHJNOPQLT-UHFFFAOYSA-N CCCS(c(nc1N2Cc3cnc(C)nc3)nc(N)c1NC2=O)(=N)=O Chemical compound CCCS(c(nc1N2Cc3cnc(C)nc3)nc(N)c1NC2=O)(=N)=O ZMNFFJHJNOPQLT-UHFFFAOYSA-N 0.000 description 1
• XYCHAVDXFFLWQJ-UHFFFAOYSA-N CCCS(c(nc1NC2CC2)nc(N2Cc3ccccc3)c1NC2=O)(=N)=O Chemical compound CCCS(c(nc1NC2CC2)nc(N2Cc3ccccc3)c1NC2=O)(=N)=O XYCHAVDXFFLWQJ-UHFFFAOYSA-N 0.000 description 1
• 0 CCCSC1=C(C)CCC(N(Cc(cc2)ccc2F)C(*C)=O)=C(C)C(N)=CC2[C@]1CC2 Chemical compound CCCSC1=C(C)CCC(N(Cc(cc2)ccc2F)C(*C)=O)=C(C)C(N)=CC2[C@]1CC2 0.000 description 1
• IPEHJFCBJPHQSW-UHFFFAOYSA-N CCCSc(nc1Cl)nc(NCc2cccc(C#N)c2)c1[NH+]([O-])[O-] Chemical compound CCCSc(nc1Cl)nc(NCc2cccc(C#N)c2)c1[NH+]([O-])[O-] IPEHJFCBJPHQSW-UHFFFAOYSA-N 0.000 description 1
• UTHROXJUYVNHHL-UHFFFAOYSA-N CCS(c(nc1N2Cc(cc3)ccc3Cl)nc(N)c1NC2=O)(=N)=O Chemical compound CCS(c(nc1N2Cc(cc3)ccc3Cl)nc(N)c1NC2=O)(=N)=O UTHROXJUYVNHHL-UHFFFAOYSA-N 0.000 description 1
• XFDVJIPIVPRMJX-UHFFFAOYSA-N CCS(c(nc1N2Cc3ccccc3)nc(N)c1NC2=O)(=N)=O Chemical compound CCS(c(nc1N2Cc3ccccc3)nc(N)c1NC2=O)(=N)=O XFDVJIPIVPRMJX-UHFFFAOYSA-N 0.000 description 1
• SGDOHGMUPCQNRK-UHFFFAOYSA-O CCSc(nc1N2Cc(cc3)ccc3[ClH+])nc(N)c1NC2=O Chemical compound CCSc(nc1N2Cc(cc3)ccc3[ClH+])nc(N)c1NC2=O SGDOHGMUPCQNRK-UHFFFAOYSA-O 0.000 description 1
• ZWIAPAKNGCZFHO-UHFFFAOYSA-N COCCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=CC=C1)C2=O)(=O)=O Chemical compound COCCS(N=C(NC(N)=C1N2)N=C1N(CC1=CC=CC=C1)C2=O)(=O)=O ZWIAPAKNGCZFHO-UHFFFAOYSA-N 0.000 description 1
• CWOJIRAKBSFUFR-UHFFFAOYSA-N COc1ccc(CN(C(N)=C(N)N2)C2=O)cc1 Chemical compound COc1ccc(CN(C(N)=C(N)N2)C2=O)cc1 CWOJIRAKBSFUFR-UHFFFAOYSA-N 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 208000000419 Chronic Hepatitis B Diseases 0.000 description 1
• 208000006154 Chronic hepatitis C Diseases 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• 102000012422 Collagen Type I Human genes 0.000 description 1
• 108010022452 Collagen Type I Proteins 0.000 description 1
• 208000035473 Communicable disease Diseases 0.000 description 1
• 229940127007 Compound 39 Drugs 0.000 description 1
• 241000699802 Cricetulus griseus Species 0.000 description 1
• 229920002785 Croscarmellose sodium Polymers 0.000 description 1
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
• 102000008144 Cytochrome P-450 CYP1A2 Human genes 0.000 description 1
• 108010074922 Cytochrome P-450 CYP1A2 Proteins 0.000 description 1
• 102000009666 Cytochrome P-450 CYP2B6 Human genes 0.000 description 1
• 108010020070 Cytochrome P-450 CYP2B6 Proteins 0.000 description 1
• NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
• 230000009946 DNA mutation Effects 0.000 description 1
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
• OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
• 206010059866 Drug resistance Diseases 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
• 108010024636 Glutathione Proteins 0.000 description 1
• 229910004373 HOAc Inorganic materials 0.000 description 1
• 208000005176 Hepatitis C Diseases 0.000 description 1
• 208000001688 Herpes Genitalis Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000855342 Homo sapiens Cytochrome P450 1A2 Proteins 0.000 description 1
• 101000957383 Homo sapiens Cytochrome P450 2B6 Proteins 0.000 description 1
• 101000745711 Homo sapiens Cytochrome P450 3A4 Proteins 0.000 description 1
• 101000831496 Homo sapiens Toll-like receptor 3 Proteins 0.000 description 1
• 101001057508 Homo sapiens Ubiquitin-like protein ISG15 Proteins 0.000 description 1
• 241000701806 Human papillomavirus Species 0.000 description 1
• MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
• 108010050904 Interferons Proteins 0.000 description 1
• 102000014150 Interferons Human genes 0.000 description 1
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
• 102000012011 Isocitrate Dehydrogenase Human genes 0.000 description 1
• 108010075869 Isocitrate Dehydrogenase Proteins 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 description 1
• 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 1
• 206010027480 Metastatic malignant melanoma Diseases 0.000 description 1
• LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
• CUWDZLCRDFFZBV-UHFFFAOYSA-N N-[(4-methoxyphenyl)methyl]-2-propylsulfanyl-9-[[4-(trifluoromethyl)phenyl]methyl]-7,8-dihydropurin-6-amine Chemical compound COC1=CC=C(C=C1)CNC1=C2NCN(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)C(F)(F)F CUWDZLCRDFFZBV-UHFFFAOYSA-N 0.000 description 1
• CPHZIZBAAHZMAC-UHFFFAOYSA-N N-[(4-methoxyphenyl)methyl]-9-[(2-methylpyridin-4-yl)methyl]-2-propylsulfanyl-7,8-dihydropurin-6-amine Chemical compound COC1=CC=C(C=C1)CNC1=C2NCN(C2=NC(=N1)SCCC)CC1=CC(=NC=C1)C CPHZIZBAAHZMAC-UHFFFAOYSA-N 0.000 description 1
• GPUATOFQYOVBCW-UHFFFAOYSA-N N-[(4-methoxyphenyl)methyl]-9-[(2-methylpyrimidin-5-yl)methyl]-2-propylsulfanyl-7,8-dihydropurin-6-amine Chemical compound COC1=CC=C(C=C1)CNC1=C2NCN(C2=NC(=N1)SCCC)CC=1C=NC(=NC=1)C GPUATOFQYOVBCW-UHFFFAOYSA-N 0.000 description 1
• LGXHISAEMZGRPW-UHFFFAOYSA-N N-[(4-methoxyphenyl)methyl]-9-[(4-methylsulfonylphenyl)methyl]-2-propylsulfanyl-7,8-dihydropurin-6-amine Chemical compound COC1=CC=C(C=C1)CNC1=C2NCN(C2=NC(=N1)SCCC)CC1=CC=C(C=C1)S(=O)(=O)C LGXHISAEMZGRPW-UHFFFAOYSA-N 0.000 description 1
• DCDWDFPLBXWYKD-UHFFFAOYSA-N N-[(4-methoxyphenyl)methyl]-9-[(6-methylpyridin-3-yl)methyl]-2-propylsulfanyl-7,8-dihydropurin-6-amine Chemical compound COC1=CC=C(C=C1)CNC1=C2NCN(C2=NC(=N1)SCCC)CC=1C=NC(=CC=1)C DCDWDFPLBXWYKD-UHFFFAOYSA-N 0.000 description 1
• YCLSUCMIRCSBJJ-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-propylsulfanyl-7H-purin-6-yl]-2,2-dimethylpropanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(C)(C)C)=O)SCCC YCLSUCMIRCSBJJ-UHFFFAOYSA-N 0.000 description 1
• IWRSPXMJFKGXRG-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-propylsulfanyl-7H-purin-6-yl]-2-ethylbutanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(CC)CC)=O)SCCC IWRSPXMJFKGXRG-UHFFFAOYSA-N 0.000 description 1
• SZOLEYUWCQFUIF-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-propylsulfanyl-7H-purin-6-yl]-2-propylpentanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(CCC)CCC)=O)SCCC SZOLEYUWCQFUIF-UHFFFAOYSA-N 0.000 description 1
• WSLPWOKZOATGMZ-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-propylsulfanyl-7H-purin-6-yl]acetamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C)=O)SCCC WSLPWOKZOATGMZ-UHFFFAOYSA-N 0.000 description 1
• GXBDXJALKOQXRE-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-propylsulfinyl-7H-purin-6-yl]-2,2-dimethylpropanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(C)(C)C)=O)S(=O)CCC GXBDXJALKOQXRE-UHFFFAOYSA-N 0.000 description 1
• TYOKNHSCNCBJSB-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-propylsulfinyl-7H-purin-6-yl]-2-propylpentanamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C(CCC)CCC)=O)S(=O)CCC TYOKNHSCNCBJSB-UHFFFAOYSA-N 0.000 description 1
• CLNXVCDSACPEIT-UHFFFAOYSA-N N-[9-[(4-chlorophenyl)methyl]-8-oxo-2-propylsulfinyl-7H-purin-6-yl]acetamide Chemical compound ClC1=CC=C(C=C1)CN1C2=NC(=NC(=C2NC1=O)NC(C)=O)S(=O)CCC CLNXVCDSACPEIT-UHFFFAOYSA-N 0.000 description 1
• HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• KODTXJWDHHLCTF-UHFFFAOYSA-N NC1=C2NC(N(C2=NC(=N1)NS(=O)(=O)CCC)CC1=CC=CC=C1)=O Chemical compound NC1=C2NC(N(C2=NC(=N1)NS(=O)(=O)CCC)CC1=CC=CC=C1)=O KODTXJWDHHLCTF-UHFFFAOYSA-N 0.000 description 1
• SKFRHTQDUBAAOJ-UHFFFAOYSA-N NC1=C2NC(N(C2=NC(N1)=NS(=O)(=O)C)CC1=CC=CC=C1)=O Chemical compound NC1=C2NC(N(C2=NC(N1)=NS(=O)(=O)C)CC1=CC=CC=C1)=O SKFRHTQDUBAAOJ-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 239000006057 Non-nutritive feed additive Substances 0.000 description 1
• 101150053185 P450 gene Proteins 0.000 description 1
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 102000004257 Potassium Channel Human genes 0.000 description 1
• 235000003893 Prunus dulcis var amara Nutrition 0.000 description 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
• 238000002123 RNA extraction Methods 0.000 description 1
• 101100288143 Rattus norvegicus Klkb1 gene Proteins 0.000 description 1
• 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-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
• 108010060818 Toll-Like Receptor 9 Proteins 0.000 description 1
• 102000008235 Toll-Like Receptor 9 Human genes 0.000 description 1
• 229940123384 Toll-like receptor (TLR) agonist Drugs 0.000 description 1
• 102100024324 Toll-like receptor 3 Human genes 0.000 description 1
• 206010066901 Treatment failure Diseases 0.000 description 1
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
• 102100027266 Ubiquitin-like protein ISG15 Human genes 0.000 description 1
• 241000700605 Viruses Species 0.000 description 1
• HOOMGTNENMZAFP-NYNCVSEMSA-N [(2r,3r,5s)-2-(5-amino-2-oxo-[1,3]thiazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)oxolan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1C[C@@H](CO)O[C@H]1N1C(=O)SC2=CN=C(N)N=C21 HOOMGTNENMZAFP-NYNCVSEMSA-N 0.000 description 1
• PRDBLLIPPDOICK-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=C(C(F)(F)F)C=C1 PRDBLLIPPDOICK-UHFFFAOYSA-N 0.000 description 1
• 239000008351 acetate buffer Substances 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 230000008484 agonism Effects 0.000 description 1
• 229940060265 aldara Drugs 0.000 description 1
• 150000001335 aliphatic alkanes Chemical group 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 230000002152 alkylating effect Effects 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 229960004977 anhydrous lactose Drugs 0.000 description 1
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 230000002072 anti-mutant effect Effects 0.000 description 1
• 239000003146 anticoagulant agent Substances 0.000 description 1
• 229940127219 anticoagulant drug Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 235000006708 antioxidants Nutrition 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 206010003119 arrhythmia Diseases 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 229960005261 aspartic acid Drugs 0.000 description 1
• 230000001580 bacterial effect Effects 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 229960002903 benzyl benzoate Drugs 0.000 description 1
• WIJRMGQOERPOJA-UHFFFAOYSA-N benzyl cyanate Chemical compound N#COCC1=CC=CC=C1 WIJRMGQOERPOJA-UHFFFAOYSA-N 0.000 description 1
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• 229960003237 betaine Drugs 0.000 description 1
• 230000036782 biological activation Effects 0.000 description 1
• 239000013060 biological fluid Substances 0.000 description 1
• 229960002685 biotin Drugs 0.000 description 1
• 235000020958 biotin Nutrition 0.000 description 1
• 239000011616 biotin Substances 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
• RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
• UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
• 239000007975 buffered saline Substances 0.000 description 1
• 239000004067 bulking agent Substances 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
• 238000010805 cDNA synthesis kit Methods 0.000 description 1
• 229960001948 caffeine Drugs 0.000 description 1
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 238000004364 calculation method Methods 0.000 description 1
• 238000011088 calibration curve Methods 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 150000003857 carboxamides Chemical class 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 230000006037 cell lysis Effects 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 229940106681 chloroacetic acid Drugs 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 208000016350 chronic hepatitis B virus infection Diseases 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 229960004106 citric acid Drugs 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 229940121657 clinical drug Drugs 0.000 description 1
• 238000011260 co-administration Methods 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000012230 colorless oil Substances 0.000 description 1
• 239000002299 complementary DNA Substances 0.000 description 1
• 229940125904 compound 1 Drugs 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• 229940127573 compound 38 Drugs 0.000 description 1
• 229940125900 compound 59 Drugs 0.000 description 1
• 238000012790 confirmation Methods 0.000 description 1
• 239000013068 control sample Substances 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 150000001879 copper Chemical class 0.000 description 1
• 229960001681 croscarmellose sodium Drugs 0.000 description 1
• 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 238000011461 current therapy Methods 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 230000009089 cytolysis Effects 0.000 description 1
• 210000005220 cytoplasmic tail Anatomy 0.000 description 1
• 229960001270 d- tartaric acid Drugs 0.000 description 1
• 238000007405 data analysis Methods 0.000 description 1
• 238000013480 data collection Methods 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
• 229960001259 diclofenac Drugs 0.000 description 1
• PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical compound CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 description 1
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000004069 differentiation Effects 0.000 description 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
• DXPIZCZNFUTPEI-UHFFFAOYSA-N diphenylphosphane;azide Chemical compound [N-]=[N+]=[N-].C=1C=CC=CC=1PC1=CC=CC=C1 DXPIZCZNFUTPEI-UHFFFAOYSA-N 0.000 description 1
• 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 231100000673 dose–response relationship Toxicity 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 238000009509 drug development Methods 0.000 description 1
• 238000007876 drug discovery Methods 0.000 description 1
• 229940125542 dual agonist Drugs 0.000 description 1
• 230000007831 electrophysiology Effects 0.000 description 1
• 238000002001 electrophysiology Methods 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 210000001163 endosome Anatomy 0.000 description 1
• 238000005516 engineering process Methods 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• IXZFDJXHLQQSGQ-UHFFFAOYSA-N ethyl 4-chloro-4-oxobutanoate Chemical compound CCOC(=O)CCC(Cl)=O IXZFDJXHLQQSGQ-UHFFFAOYSA-N 0.000 description 1
• KMJTTWREVXZPTK-UHFFFAOYSA-N ethyl(methyl)carbamic acid Chemical compound CCN(C)C(O)=O KMJTTWREVXZPTK-UHFFFAOYSA-N 0.000 description 1
• 229940012017 ethylenediamine Drugs 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 239000012634 fragment Substances 0.000 description 1
• 239000003205 fragrance Substances 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 229960002598 fumaric acid Drugs 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 201000004946 genital herpes Diseases 0.000 description 1
• 239000000174 gluconic acid Substances 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 229960002442 glucosamine Drugs 0.000 description 1
• 244000144993 groups of animals Species 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 208000006454 hepatitis Diseases 0.000 description 1
• 231100000283 hepatitis Toxicity 0.000 description 1
• 231100000304 hepatotoxicity Toxicity 0.000 description 1
• 125000001072 heteroaryl group Chemical group 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 229960001340 histamine Drugs 0.000 description 1
• 229960002885 histidine Drugs 0.000 description 1
• 102000057459 human CYP1A2 Human genes 0.000 description 1
• 102000047894 human CYP2B6 Human genes 0.000 description 1
• 102000044284 human CYP3A4 Human genes 0.000 description 1
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
• 238000010191 image analysis Methods 0.000 description 1
• 229960002751 imiquimod Drugs 0.000 description 1
• 210000002865 immune cell Anatomy 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 230000001939 inductive effect Effects 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 230000000977 initiatory effect Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 229940079322 interferon Drugs 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 150000002497 iodine compounds Chemical class 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 150000002505 iron Chemical class 0.000 description 1
• ODBLHEXUDAPZAU-UHFFFAOYSA-N isocitric acid Chemical compound OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• 210000004731 jugular vein Anatomy 0.000 description 1
• 229960000448 lactic acid Drugs 0.000 description 1
• FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
• 238000002514 liquid chromatography mass spectrum Methods 0.000 description 1
• 210000005229 liver cell Anatomy 0.000 description 1
• 230000007056 liver toxicity Effects 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000012931 lyophilized formulation Substances 0.000 description 1
• 239000012139 lysis buffer Substances 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 229940099690 malic acid Drugs 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 150000002696 manganese Chemical class 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 208000021039 metastatic melanoma Diseases 0.000 description 1
• QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
• AQBJGAUQEJFPKZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CN)C=C1 AQBJGAUQEJFPKZ-UHFFFAOYSA-N 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 210000001589 microsome Anatomy 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
• 230000007886 mutagenicity Effects 0.000 description 1
• 231100000299 mutagenicity Toxicity 0.000 description 1
• GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 1
• VRBKIVRKKCLPHA-UHFFFAOYSA-N nefazodone Chemical compound O=C1N(CCOC=2C=CC=CC=2)C(CC)=NN1CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 VRBKIVRKKCLPHA-UHFFFAOYSA-N 0.000 description 1
• 229960001800 nefazodone Drugs 0.000 description 1
• 239000013642 negative control Substances 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
• 239000006186 oral dosage form Substances 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
• 239000003002 pH adjusting agent Substances 0.000 description 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 230000001717 pathogenic effect Effects 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 239000000137 peptide hydrolase inhibitor Substances 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
• 239000002953 phosphate buffered saline Substances 0.000 description 1
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
• 230000036470 plasma concentration Effects 0.000 description 1
• 210000004180 plasmocyte Anatomy 0.000 description 1
• 229920000768 polyamine Polymers 0.000 description 1
• 229920000137 polyphosphoric acid Polymers 0.000 description 1
• 239000011148 porous material Substances 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 108020001213 potassium channel Proteins 0.000 description 1
• 239000001103 potassium chloride Substances 0.000 description 1
• 235000011164 potassium chloride Nutrition 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• 238000002540 product ion scan Methods 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000004544 purin-8-yl group Chemical group N1=CN=C2N=C(NC2=C1)* 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 230000010076 replication Effects 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• BXNMTOQRYBFHNZ-UHFFFAOYSA-N resiquimod Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)O)C3=C(N)N=C21 BXNMTOQRYBFHNZ-UHFFFAOYSA-N 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 238000010839 reverse transcription Methods 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 239000013049 sediment Substances 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 206010040882 skin lesion Diseases 0.000 description 1
• 231100000444 skin lesion Toxicity 0.000 description 1
• 239000012748 slip agent Substances 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000001488 sodium phosphate Substances 0.000 description 1
• 229910000162 sodium phosphate Inorganic materials 0.000 description 1
• 239000012064 sodium phosphate buffer Substances 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 229940014800 succinic anhydride Drugs 0.000 description 1
• 230000000475 sunscreen effect Effects 0.000 description 1
• 239000000516 sunscreening agent 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
• 238000003786 synthesis reaction Methods 0.000 description 1
• 230000002194 synthesizing effect Effects 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 230000001839 systemic circulation Effects 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 238000004885 tandem mass spectrometry Methods 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 229960001367 tartaric acid Drugs 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• 229960004559 theobromine Drugs 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 239000003970 toll like receptor agonist Substances 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 102000035160 transmembrane proteins Human genes 0.000 description 1
• 108091005703 transmembrane proteins Proteins 0.000 description 1
• SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
• GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
• 229960001641 troglitazone Drugs 0.000 description 1
• GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 150000003751 zinc Chemical class 0.000 description 1