NO328208B1 - Inhibitorer for cruzipain og andre cysteinproteaser, fremgangsmate for validering av en kjent eller antatt cysteinproteaseinhibitor som et terapeutisk mal, anvendelser av forbindelsene i fremgangsmaten og ved fremstilling av medikamenter, samt farmasoytiske eller veterinaermedisinske preparater og fremgangsmate for fremstilling derav - Google Patents

Info

Publication number

NO328208B1

NO328208B1 NO20033220A NO20033220A NO328208B1 NO 328208 B1 NO328208 B1 NO 328208B1 NO 20033220 A NO20033220 A NO 20033220A NO 20033220 A NO20033220 A NO 20033220A NO 328208 B1 NO328208 B1 NO 328208B1

Authority

NO

Norway

Prior art keywords

oxohexahydrofuro

oxo

pyrrol

ethyl

alkyl

Prior art date

2001-01-17

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 211
• 239000003814 drug Substances 0.000 title claims abstract description 20
• 230000001225 therapeutic effect Effects 0.000 title claims abstract description 13
• 238000002360 preparation method Methods 0.000 title claims description 58
• 238000000034 method Methods 0.000 title claims description 48
• 102000005927 Cysteine Proteases Human genes 0.000 title claims description 37
• 108010005843 Cysteine Proteases Proteins 0.000 title claims description 37
• 101000749287 Clitocybe nebularis Clitocypin Proteins 0.000 title claims description 7
• 101000767029 Clitocybe nebularis Clitocypin-1 Proteins 0.000 title claims description 7
• 229940094664 Cysteine protease inhibitor Drugs 0.000 title claims description 7
• 238000004519 manufacturing process Methods 0.000 title claims description 5
• 239000003112 inhibitor Substances 0.000 title abstract description 46
• 108090000711 cruzipain Proteins 0.000 title abstract description 22
• 206010001935 American trypanosomiasis Diseases 0.000 claims abstract description 15
• 208000024699 Chagas disease Diseases 0.000 claims abstract description 14
• 125000003118 aryl group Chemical group 0.000 claims description 83
• 102000035195 Peptidases Human genes 0.000 claims description 47
• 108091005804 Peptidases Proteins 0.000 claims description 47
• 230000000694 effects Effects 0.000 claims description 46
• 239000004365 Protease Substances 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 238000011282 treatment Methods 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 26
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 24
• 201000010099 disease Diseases 0.000 claims description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 229940079593 drug Drugs 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 238000000338 in vitro Methods 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• 239000003550 marker Substances 0.000 claims description 7
• 238000011321 prophylaxis Methods 0.000 claims description 7
• 108090000631 Trypsin Proteins 0.000 claims description 6
• 102000004142 Trypsin Human genes 0.000 claims description 6
• 238000010171 animal model Methods 0.000 claims description 5
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 239000012588 trypsin Substances 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 230000007170 pathology Effects 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 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
• 238000002156 mixing Methods 0.000 claims description 2
• 239000002852 cysteine proteinase inhibitor Substances 0.000 abstract description 3
• 229940124597 therapeutic agent Drugs 0.000 abstract description 2
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 220
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 197
• 238000004128 high performance liquid chromatography Methods 0.000 description 176
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 172
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 165
• 150000001408 amides Chemical class 0.000 description 139
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 136
• 239000011734 sodium Substances 0.000 description 130
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 122
• -1 tetrahydrofurancarbonyl residue Chemical group 0.000 description 118
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 116
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 91
• 238000006243 chemical reaction Methods 0.000 description 91
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 85
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 77
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
• 239000000243 solution Substances 0.000 description 74
• 239000000203 mixture Substances 0.000 description 63
• 239000000758 substrate Substances 0.000 description 59
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 52
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
• 235000019439 ethyl acetate Nutrition 0.000 description 46
• 150000002148 esters Chemical class 0.000 description 45
• 239000002904 solvent Substances 0.000 description 43
• 229910001868 water Inorganic materials 0.000 description 43
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
• 238000003556 assay Methods 0.000 description 39
• 239000007790 solid phase Substances 0.000 description 39
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 38
• 125000005647 linker group Chemical group 0.000 description 37
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 34
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
• 230000002829 reductive effect Effects 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• 238000004458 analytical method Methods 0.000 description 31
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 31
• 238000004809 thin layer chromatography Methods 0.000 description 31
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
• 239000000047 product Substances 0.000 description 28
• 239000007787 solid Substances 0.000 description 27
• 239000000741 silica gel Substances 0.000 description 26
• 229910002027 silica gel Inorganic materials 0.000 description 26
• 102000004190 Enzymes Human genes 0.000 description 25
• 108090000790 Enzymes Proteins 0.000 description 25
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
• 238000005859 coupling reaction Methods 0.000 description 25
• 229940088598 enzyme Drugs 0.000 description 25
• 230000008878 coupling Effects 0.000 description 24
• 238000010168 coupling process Methods 0.000 description 24
• 239000003921 oil Substances 0.000 description 24
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 21
• 230000005764 inhibitory process Effects 0.000 description 21
• 238000003786 synthesis reaction Methods 0.000 description 21
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 20
• 239000001301 oxygen Substances 0.000 description 20
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 18
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 17
• 230000015572 biosynthetic process Effects 0.000 description 17
• 235000019419 proteases Nutrition 0.000 description 17
• 235000002639 sodium chloride Nutrition 0.000 description 17
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000000543 intermediate Substances 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• 238000010276 construction Methods 0.000 description 14
• 239000010410 layer Substances 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 13
• 102100024940 Cathepsin K Human genes 0.000 description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 12
• 238000003776 cleavage reaction Methods 0.000 description 12
• 239000010779 crude oil Substances 0.000 description 12
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
• 244000045947 parasite Species 0.000 description 12
• 230000007017 scission Effects 0.000 description 12
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• 125000001424 substituent group Chemical group 0.000 description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
• OIEAXXWLLCWXTO-UHFFFAOYSA-N 4,5,6,6a-tetrahydro-3ah-furo[3,2-b]pyrrol-3-one Chemical compound C1CNC2C(=O)COC21 OIEAXXWLLCWXTO-UHFFFAOYSA-N 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• 208000015181 infectious disease Diseases 0.000 description 11
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
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• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 229940024606 amino acid Drugs 0.000 description 10
• 235000001014 amino acid Nutrition 0.000 description 10
• 150000001413 amino acids Chemical group 0.000 description 10
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• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• WHEGUFRCPJIXTI-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydrofuro[3,2-b]pyridin-3-one Chemical compound C1CCNC2C(=O)COC21 WHEGUFRCPJIXTI-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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• 229910052757 nitrogen Inorganic materials 0.000 description 9
• LCRIQYBVMHKKQY-WOJBJXKFSA-N 9h-fluoren-9-ylmethyl (3as,6ar)-3-oxo-3a,5,6,6a-tetrahydrofuro[3,2-b]pyrrole-4-carboxylate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)N1[C@@H]2C(=O)CO[C@@H]2CC1 LCRIQYBVMHKKQY-WOJBJXKFSA-N 0.000 description 8
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
• 150000001280 alpha hydroxy acids Chemical class 0.000 description 8
• 238000012544 monitoring process Methods 0.000 description 8
• CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 8
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 8
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• UIYKSYBJKIMANV-UHFFFAOYSA-N (4-tert-butylphenyl)methanethiol Chemical compound CC(C)(C)C1=CC=C(CS)C=C1 UIYKSYBJKIMANV-UHFFFAOYSA-N 0.000 description 6
• YBZSZBMPLNFKHZ-UHFFFAOYSA-N 1,2,3,4,4a,7a-hexahydrofuro[3,2-c]pyridazin-7-one Chemical compound C1CNNC2C(=O)COC21 YBZSZBMPLNFKHZ-UHFFFAOYSA-N 0.000 description 6
• XQMISVCEOCKXDM-UHFFFAOYSA-N 1,2,3,4,4a,7a-hexahydrothieno[3,2-c]pyridazin-7-one Chemical compound C1CNNC2C(=O)CSC21 XQMISVCEOCKXDM-UHFFFAOYSA-N 0.000 description 6
• SDSMTVZDVOWXEW-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydro-1h-cyclopenta[b]pyrrol-6-one Chemical compound C1CNC2C(=O)CCC21 SDSMTVZDVOWXEW-UHFFFAOYSA-N 0.000 description 6
• TYESAUSOQPZWJN-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydro-1h-cyclopenta[c]pyrazol-6-one Chemical compound C1NNC2C(=O)CCC21 TYESAUSOQPZWJN-UHFFFAOYSA-N 0.000 description 6
• ISKGDMGVYKKRNB-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydro-1h-pyrrolo[3,2-c]pyrazol-6-one Chemical compound C1NNC2C(=O)CNC21 ISKGDMGVYKKRNB-UHFFFAOYSA-N 0.000 description 6
• AYWILFZKEQCPRG-UHFFFAOYSA-N 2,3,3a,6a-tetrahydro-1h-furo[3,2-c]pyrazol-6-one Chemical compound C1NNC2C(=O)COC21 AYWILFZKEQCPRG-UHFFFAOYSA-N 0.000 description 6
• ARPKZUFJSMWIDF-UHFFFAOYSA-N 2,3,3a,6a-tetrahydro-1h-thieno[3,2-c]pyrazol-6-one Chemical compound C1NNC2C(=O)CSC21 ARPKZUFJSMWIDF-UHFFFAOYSA-N 0.000 description 6
• LSQFTCHHVMCXMO-UHFFFAOYSA-N 4-[(hydrazinecarbonylamino)methyl]cyclohexane-1-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NNC(=O)NCC1CCC(C(O)=O)CC1 LSQFTCHHVMCXMO-UHFFFAOYSA-N 0.000 description 6
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• 239000007989 BIS-Tris Propane buffer Substances 0.000 description 6
• 102100035654 Cathepsin S Human genes 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
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• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• HHKZCCWKTZRCCL-UHFFFAOYSA-N bis-tris propane Chemical compound OCC(CO)(CO)NCCCNC(CO)(CO)CO HHKZCCWKTZRCCL-UHFFFAOYSA-N 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
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• 239000007789 gas Substances 0.000 description 6
• 238000011068 loading method Methods 0.000 description 6
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• 229910000104 sodium hydride Inorganic materials 0.000 description 6
• PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 5
• GGPQSXXVEVFBQI-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydro-1h-pyrrolo[3,2-b]pyrrol-6-one Chemical compound C1CNC2C(=O)CNC21 GGPQSXXVEVFBQI-UHFFFAOYSA-N 0.000 description 5
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 5
• RPGUXSFNXRNACR-UHFFFAOYSA-N 2-hydroxyethyl 2-piperazin-1-ylethanesulfonate Chemical compound OCCOS(=O)(=O)CCN1CCNCC1 RPGUXSFNXRNACR-UHFFFAOYSA-N 0.000 description 5
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
• NOZHZZBNUKSIAF-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydrothieno[3,2-b]pyridin-3-one Chemical compound C1CCNC2C(=O)CSC21 NOZHZZBNUKSIAF-UHFFFAOYSA-N 0.000 description 5
• NTFPNOFKJYNOPR-UHFFFAOYSA-N 4,5,6,6a-tetrahydro-3ah-thieno[3,2-b]pyrrol-3-one Chemical compound C1CNC2C(=O)CSC21 NTFPNOFKJYNOPR-UHFFFAOYSA-N 0.000 description 5
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• 102000004172 Cathepsin L Human genes 0.000 description 5
• 101000761509 Homo sapiens Cathepsin K Proteins 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
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• 230000004913 activation Effects 0.000 description 5
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• 239000000969 carrier Substances 0.000 description 5
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