TW470750B - Reversible cysteine protease inhibitors - Google Patents

Info

Publication number

TW470750B

TW470750B TW085104392A TW85104392A TW470750B TW 470750 B TW470750 B TW 470750B TW 085104392 A TW085104392 A TW 085104392A TW 85104392 A TW85104392 A TW 85104392A TW 470750 B TW470750 B TW 470750B

Authority

TW

Taiwan

Prior art keywords

compound

formula

group

phenyl

patent application

Prior art date

1995-03-24

Links

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• 239000002852 cysteine proteinase inhibitor Substances 0.000 title description 22
• 230000002441 reversible effect Effects 0.000 title description 9
• -1 morpholinecarbonyl Chemical group 0.000 claims abstract description 240
• 150000001875 compounds Chemical class 0.000 claims abstract description 181
• 239000000203 mixture Substances 0.000 claims abstract description 110
• 101000749287 Clitocybe nebularis Clitocypin Proteins 0.000 claims abstract description 70
• 101000767029 Clitocybe nebularis Clitocypin-1 Proteins 0.000 claims abstract description 70
• 229940094664 Cysteine protease inhibitor Drugs 0.000 claims abstract description 70
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 64
• 239000001257 hydrogen Substances 0.000 claims abstract description 63
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 49
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 45
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 41
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 29
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 19
• 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 abstract description 18
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
• 239000003112 inhibitor Substances 0.000 claims description 72
• 108010005843 Cysteine Proteases Proteins 0.000 claims description 66
• 102000005927 Cysteine Proteases Human genes 0.000 claims description 65
• 125000000217 alkyl group Chemical group 0.000 claims description 62
• 230000002079 cooperative effect Effects 0.000 claims description 62
• 238000011049 filling Methods 0.000 claims description 58
• 238000000034 method Methods 0.000 claims description 49
• 150000001412 amines Chemical class 0.000 claims description 36
• 239000004365 Protease Substances 0.000 claims description 34
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 34
• 102000035195 Peptidases Human genes 0.000 claims description 31
• 108091005804 Peptidases Proteins 0.000 claims description 31
• 238000006243 chemical reaction Methods 0.000 claims description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 238000010494 dissociation reaction Methods 0.000 claims description 17
• 230000005593 dissociations Effects 0.000 claims description 17
• 230000002401 inhibitory effect Effects 0.000 claims description 14
• 239000002671 adjuvant Substances 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 239000011734 sodium Substances 0.000 claims description 11
• 229940124530 sulfonamide Drugs 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 229910052796 boron Inorganic materials 0.000 claims description 8
• 229910052708 sodium Inorganic materials 0.000 claims description 8
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 230000009467 reduction Effects 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 238000010511 deprotection reaction Methods 0.000 claims description 6
• 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 5
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
• 238000000338 in vitro Methods 0.000 claims description 5
• LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 claims description 4
• 108091005508 Acid proteases Proteins 0.000 claims description 4
• UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 4
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
• 229960003151 mercaptamine Drugs 0.000 claims description 4
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 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
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 9
• 125000003884 phenylalkyl group Chemical group 0.000 claims 2
• 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 claims 1
• 125000005907 alkyl ester group Chemical group 0.000 claims 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
• POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 claims 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
• DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
• 239000000243 solution Substances 0.000 description 104
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
• 230000015572 biosynthetic process Effects 0.000 description 59
• 238000003786 synthesis reaction Methods 0.000 description 59
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
• 230000002829 reductive effect Effects 0.000 description 46
• 125000003118 aryl group Chemical group 0.000 description 38
• 239000002904 solvent Substances 0.000 description 34
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 32
• 102000004190 Enzymes Human genes 0.000 description 31
• 108090000790 Enzymes Proteins 0.000 description 31
• 229940088598 enzyme Drugs 0.000 description 31
• 239000000047 product Substances 0.000 description 31
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
• 239000002253 acid Substances 0.000 description 28
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 27
• 230000000875 corresponding effect Effects 0.000 description 26
• 201000010099 disease Diseases 0.000 description 26
• 125000000753 cycloalkyl group Chemical group 0.000 description 24
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 23
• 229940024606 amino acid Drugs 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 235000001014 amino acid Nutrition 0.000 description 21
• 239000000543 intermediate Substances 0.000 description 21
• 235000019419 proteases Nutrition 0.000 description 21
• 125000004432 carbon atom Chemical group C* 0.000 description 20
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• 150000001299 aldehydes Chemical class 0.000 description 19
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
• 125000001424 substituent group Chemical group 0.000 description 18
• DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
• 239000000463 material Substances 0.000 description 17
• 108090000765 processed proteins & peptides Proteins 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• 150000001413 amino acids Chemical class 0.000 description 15
• 239000011737 fluorine Chemical group 0.000 description 15
• 229910052731 fluorine Inorganic materials 0.000 description 15
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
• 239000007787 solid Substances 0.000 description 15
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
• COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 14
• 229910000104 sodium hydride Inorganic materials 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 13
• 239000007864 aqueous solution Substances 0.000 description 13
• 229910052799 carbon Inorganic materials 0.000 description 13
• 239000000460 chlorine Substances 0.000 description 13
• 125000005843 halogen group Chemical group 0.000 description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
• 125000003710 aryl alkyl group Chemical group 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• 229910052801 chlorine Inorganic materials 0.000 description 12
• 239000000816 peptidomimetic Substances 0.000 description 12
• 229960005190 phenylalanine Drugs 0.000 description 12
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
• 206010028980 Neoplasm Diseases 0.000 description 11
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
• 229910052794 bromium Inorganic materials 0.000 description 11
• COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 11
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• 125000001072 heteroaryl group Chemical group 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
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• 101100240520 Caenorhabditis elegans nhr-14 gene Proteins 0.000 description 8
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• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
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• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 7
• 238000010586 diagram Methods 0.000 description 7
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
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• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
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