CZ298197A3 - Reverzibilní inhibitory proteas - Google Patents

Info

Publication number

CZ298197A3

CZ298197A3 CZ972981A CZ298197A CZ298197A3 CZ 298197 A3 CZ298197 A3 CZ 298197A3 CZ 972981 A CZ972981 A CZ 972981A CZ 298197 A CZ298197 A CZ 298197A CZ 298197 A3 CZ298197 A3 CZ 298197A3

Authority

CZ

Czechia

Prior art keywords

substituted

unsubstituted

alkyl

hydrogen

group

Prior art date

1995-03-24

Links

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• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title claims abstract description 83
• 239000004365 Protease Substances 0.000 title claims description 44
• 102000035195 Peptidases Human genes 0.000 title claims description 40
• 108091005804 Peptidases Proteins 0.000 title claims description 40
• 230000002441 reversible effect Effects 0.000 title abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 217
• 108010005843 Cysteine Proteases Proteins 0.000 claims abstract description 61
• 102000005927 Cysteine Proteases Human genes 0.000 claims abstract description 60
• 239000000137 peptide hydrolase inhibitor Substances 0.000 claims abstract description 23
• -1 carboxy, carbamoyl Chemical group 0.000 claims description 493
• 125000000217 alkyl group Chemical group 0.000 claims description 169
• 229910052739 hydrogen Inorganic materials 0.000 claims description 145
• 239000001257 hydrogen Substances 0.000 claims description 143
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 135
• 125000003118 aryl group Chemical group 0.000 claims description 120
• 239000000203 mixture Substances 0.000 claims description 115
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 78
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 68
• 229910052736 halogen Inorganic materials 0.000 claims description 68
• 150000002367 halogens Chemical class 0.000 claims description 68
• 150000002431 hydrogen Chemical class 0.000 claims description 68
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 59
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 59
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 53
• 239000000460 chlorine Substances 0.000 claims description 52
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 50
• 101000749287 Clitocybe nebularis Clitocypin Proteins 0.000 claims description 49
• 101000767029 Clitocybe nebularis Clitocypin-1 Proteins 0.000 claims description 49
• 229940094664 Cysteine protease inhibitor Drugs 0.000 claims description 49
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 46
• 238000000034 method Methods 0.000 claims description 45
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 41
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 40
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 38
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 35
• 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 33
• 238000006243 chemical reaction Methods 0.000 claims description 32
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 25
• 230000005764 inhibitory process Effects 0.000 claims description 25
• 125000004043 oxo group Chemical group O=* 0.000 claims description 25
• 125000005842 heteroatom Chemical group 0.000 claims description 23
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• 125000005647 linker group Chemical group 0.000 claims description 19
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000001624 naphthyl group Chemical group 0.000 claims description 18
• 238000010494 dissociation reaction Methods 0.000 claims description 17
• 230000005593 dissociations Effects 0.000 claims description 17
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 16
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
• 229910052794 bromium Inorganic materials 0.000 claims description 16
• 239000011737 fluorine Substances 0.000 claims description 16
• 229910052731 fluorine Inorganic materials 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 16
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 15
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 15
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 13
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 13
• 125000003282 alkyl amino group Chemical group 0.000 claims description 12
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
• 125000001246 bromo group Chemical group Br* 0.000 claims description 12
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
• 230000009467 reduction Effects 0.000 claims description 12
• 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 11
• 125000001041 indolyl group Chemical group 0.000 claims description 11
• 230000008685 targeting Effects 0.000 claims description 11
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 9
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
• 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 8
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000006239 protecting group Chemical group 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 claims description 7
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 7
• 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 7
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 6
• 125000001174 sulfone group Chemical group 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
• 125000003435 aroyl group Chemical group 0.000 claims description 5
• 150000001721 carbon Chemical group 0.000 claims description 5
• 238000010511 deprotection reaction Methods 0.000 claims description 5
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
• 239000011734 sodium Substances 0.000 claims description 5
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 4
• ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 claims description 4
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 4
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
• 229910052708 sodium Inorganic materials 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004423 acyloxy group Chemical group 0.000 claims description 3
• 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
• 125000001188 haloalkyl group Chemical group 0.000 claims description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
• 230000001590 oxidative effect Effects 0.000 claims description 2
• 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 2
• 150000003254 radicals Chemical class 0.000 claims 60
• 125000001589 carboacyl group Chemical group 0.000 claims 27
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 22
• 125000000547 substituted alkyl group Chemical group 0.000 claims 20
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 5
• AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 claims 4
• 238000004519 manufacturing process Methods 0.000 claims 4
• QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 abstract description 7
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 122
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
• 239000000243 solution Substances 0.000 description 82
• 230000015572 biosynthetic process Effects 0.000 description 70
• 238000003786 synthesis reaction Methods 0.000 description 69
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 60
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 43
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 43
• 235000019439 ethyl acetate Nutrition 0.000 description 41
• 239000002904 solvent Substances 0.000 description 35
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
• 102000004190 Enzymes Human genes 0.000 description 31
• 108090000790 Enzymes Proteins 0.000 description 31
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 31
• 229940088598 enzyme Drugs 0.000 description 31
• 229920006395 saturated elastomer Polymers 0.000 description 28
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 230000000875 corresponding effect Effects 0.000 description 25
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
• 239000000047 product Substances 0.000 description 25
• 239000002852 cysteine proteinase inhibitor Substances 0.000 description 23
• 229940024606 amino acid Drugs 0.000 description 22
• 235000001014 amino acid Nutrition 0.000 description 22
• 201000010099 disease Diseases 0.000 description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 22
• 108090000765 processed proteins & peptides Proteins 0.000 description 22
• 239000000758 substrate Substances 0.000 description 22
• 238000004809 thin layer chromatography Methods 0.000 description 22
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 21
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 20
• 239000000463 material Substances 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 150000001299 aldehydes Chemical class 0.000 description 18
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 18
• 235000019419 proteases Nutrition 0.000 description 17
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
• 239000000126 substance Substances 0.000 description 16
• 229910000104 sodium hydride Inorganic materials 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• 239000011780 sodium chloride Substances 0.000 description 13
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
• 150000001413 amino acids Chemical class 0.000 description 12
• 125000002252 acyl group Chemical group 0.000 description 11
• 125000003275 alpha amino acid group Chemical group 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 238000006722 reduction reaction Methods 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• 206010028980 Neoplasm Diseases 0.000 description 9
• 229960005190 phenylalanine Drugs 0.000 description 9
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 9
• 241001465754 Metazoa Species 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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• 239000012312 sodium hydride Substances 0.000 description 8
• 150000003457 sulfones Chemical class 0.000 description 8
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
• 206010061218 Inflammation Diseases 0.000 description 7
• QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 7
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• LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 description 7
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 7
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• 239000002253 acid Substances 0.000 description 7
• 235000004279 alanine Nutrition 0.000 description 7
• 125000004429 atom Chemical group 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• 230000004054 inflammatory process Effects 0.000 description 7
• 210000001519 tissue Anatomy 0.000 description 7
• 239000004475 Arginine Substances 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• 108090000624 Cathepsin L Proteins 0.000 description 6
• 102000004172 Cathepsin L Human genes 0.000 description 6
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 6
• 241000700605 Viruses Species 0.000 description 6
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 108090000711 cruzipain Proteins 0.000 description 6
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• 235000019253 formic acid Nutrition 0.000 description 6
• 230000007062 hydrolysis Effects 0.000 description 6
• 238000006460 hydrolysis reaction Methods 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
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