HRP20010737A2 - N-cyanomethylamides as protease inhibitors - Google Patents
N-cyanomethylamides as protease inhibitors Download PDFInfo
- Publication number
- HRP20010737A2 HRP20010737A2 HR20010737A HRP20010737A HRP20010737A2 HR P20010737 A2 HRP20010737 A2 HR P20010737A2 HR 20010737 A HR20010737 A HR 20010737A HR P20010737 A HRP20010737 A HR P20010737A HR P20010737 A2 HRP20010737 A2 HR P20010737A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- compound
- benzamide
- substituted
- halo
- Prior art date
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- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical class NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 title abstract description 34
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 51
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims description 488
- 125000000217 alkyl group Chemical group 0.000 claims description 246
- -1 trimethylene, tetramethylene Chemical group 0.000 claims description 144
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 117
- 229910052739 hydrogen Inorganic materials 0.000 claims description 107
- 239000001257 hydrogen Substances 0.000 claims description 105
- 125000003118 aryl group Chemical group 0.000 claims description 101
- 239000000203 mixture Substances 0.000 claims description 99
- 125000005842 heteroatom Chemical group 0.000 claims description 91
- 239000002253 acid Substances 0.000 claims description 90
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 87
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 79
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 201000010099 disease Diseases 0.000 claims description 33
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 29
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 23
- 150000007513 acids Chemical class 0.000 claims description 23
- 125000001118 alkylidene group Chemical group 0.000 claims description 20
- 239000000651 prodrug Substances 0.000 claims description 20
- 229940002612 prodrug Drugs 0.000 claims description 20
- 125000001072 heteroaryl group Chemical class 0.000 claims description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 125000002723 alicyclic group Chemical group 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical class 0.000 claims description 17
- 241001465754 Metazoa Species 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 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 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 102000005927 Cysteine Proteases Human genes 0.000 claims description 11
- 108010005843 Cysteine Proteases Proteins 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical class 0.000 claims description 10
- 230000009471 action Effects 0.000 claims description 9
- 108090000625 Cathepsin K Proteins 0.000 claims description 8
- 102000004171 Cathepsin K Human genes 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 7
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 230000007170 pathology Effects 0.000 claims description 6
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 6
- 208000001132 Osteoporosis Diseases 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 5
- 102000015694 estrogen receptors Human genes 0.000 claims description 5
- 108010038795 estrogen receptors Proteins 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
- KOUXXQSBRWTPSF-UHFFFAOYSA-N n-[1-(cyanomethylamino)-4-methyl-1-oxopentan-2-yl]-3-(pyridin-2-ylcarbamoylamino)benzamide Chemical compound N#CCNC(=O)C(CC(C)C)NC(=O)C1=CC=CC(NC(=O)NC=2N=CC=CC=2)=C1 KOUXXQSBRWTPSF-UHFFFAOYSA-N 0.000 claims description 4
- ZVXVCSFLPDQOFS-UHFFFAOYSA-N n-[1-(cyanomethylamino)-4-methyl-1-oxopentan-2-yl]-4-(piperidin-4-ylcarbamoylamino)benzamide Chemical compound C1=CC(C(=O)NC(CC(C)C)C(=O)NCC#N)=CC=C1NC(=O)NC1CCNCC1 ZVXVCSFLPDQOFS-UHFFFAOYSA-N 0.000 claims description 4
- TYJLGELUBBAGKK-UHFFFAOYSA-N n-[1-(cyanomethylcarbamoyl)cyclohexyl]-4-(2-morpholin-4-yl-1,3-thiazol-4-yl)benzamide Chemical compound C=1C=C(C=2N=C(SC=2)N2CCOCC2)C=CC=1C(=O)NC1(C(=O)NCC#N)CCCCC1 TYJLGELUBBAGKK-UHFFFAOYSA-N 0.000 claims description 4
- HJOXUKZNYOVXDZ-UHFFFAOYSA-N n-[1-(cyanomethylcarbamoyl)cyclohexyl]-4-(2-piperazin-1-yl-1,3-thiazol-4-yl)benzamide Chemical compound C=1C=C(C=2N=C(SC=2)N2CCNCC2)C=CC=1C(=O)NC1(C(=O)NCC#N)CCCCC1 HJOXUKZNYOVXDZ-UHFFFAOYSA-N 0.000 claims description 4
- JVPVQZVJMIEJPE-UHFFFAOYSA-N n-[1-(cyanomethylcarbamoyl)cyclohexyl]-4-[2-(piperazin-1-ylmethyl)-1,3-thiazol-4-yl]benzamide Chemical compound C=1C=C(C=2N=C(CN3CCNCC3)SC=2)C=CC=1C(=O)NC1(C(=O)NCC#N)CCCCC1 JVPVQZVJMIEJPE-UHFFFAOYSA-N 0.000 claims description 4
- SIPOTAOXKMZPFX-UHFFFAOYSA-N n-[1-(cyanomethylcarbamoyl)cyclohexyl]-4-[2-(piperidin-4-ylamino)-1,3-thiazol-4-yl]benzamide Chemical compound C=1C=C(C=2N=C(NC3CCNCC3)SC=2)C=CC=1C(=O)NC1(C(=O)NCC#N)CCCCC1 SIPOTAOXKMZPFX-UHFFFAOYSA-N 0.000 claims description 4
- WIJNHFXLYZGIJV-UHFFFAOYSA-N n-[1-[(4-cyanooxan-4-yl)carbamoyl]cyclohexyl]-4-[2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]benzamide Chemical compound C1CN(C)CCN1C1=NC(C=2C=CC(=CC=2)C(=O)NC2(CCCCC2)C(=O)NC2(CCOCC2)C#N)=CS1 WIJNHFXLYZGIJV-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- OSXJMKADIOMXMP-IBGZPJMESA-N n-[(2s)-1-(cyanomethylamino)-4-methyl-1-oxopent-4-en-2-yl]-4-[2-(pyridin-4-ylamino)-1,3-thiazol-4-yl]benzamide Chemical compound C1=CC(C(=O)N[C@@H](CC(=C)C)C(=O)NCC#N)=CC=C1C1=CSC(NC=2C=CN=CC=2)=N1 OSXJMKADIOMXMP-IBGZPJMESA-N 0.000 claims description 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- KVKJSQQQFLTFKO-UHFFFAOYSA-N C1=CC(C(=O)NC(CC(C)C)C(=O)NCC#N)=CC=C1NC(=O)N1CCC(N(C)C)CC1 Chemical compound C1=CC(C(=O)NC(CC(C)C)C(=O)NCC#N)=CC=C1NC(=O)N1CCC(N(C)C)CC1 KVKJSQQQFLTFKO-UHFFFAOYSA-N 0.000 claims description 2
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical group [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 2
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 2
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 2
- VULXDFLCVUUTAQ-FQEVSTJZSA-N n-[(2s)-1-[(1-cyanocyclopropyl)amino]-4-methyl-1-oxopentan-2-yl]-4-[2-(piperazin-1-ylmethyl)-1,3-thiazol-4-yl]benzamide Chemical compound N([C@@H](CC(C)C)C(=O)NC1(CC1)C#N)C(=O)C(C=C1)=CC=C1C(N=1)=CSC=1CN1CCNCC1 VULXDFLCVUUTAQ-FQEVSTJZSA-N 0.000 claims description 2
- ZKTHKRQXMDNCKL-UHFFFAOYSA-N n-[1-(cyanomethylamino)-4-methyl-1-oxopentan-2-yl]-3-(3-morpholin-4-ylpropylcarbamoylamino)benzamide Chemical compound N#CCNC(=O)C(CC(C)C)NC(=O)C1=CC=CC(NC(=O)NCCCN2CCOCC2)=C1 ZKTHKRQXMDNCKL-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000002852 cysteine proteinase inhibitor Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 2
- 229940124597 therapeutic agent Drugs 0.000 abstract description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 359
- 238000005160 1H NMR spectroscopy Methods 0.000 description 173
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 68
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 62
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 59
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 30
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- 125000006239 protecting group Chemical group 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 150000003254 radicals Chemical class 0.000 description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- GQHJCLXWRQHKPT-SSDOTTSWSA-N (2R)-2-amino-N-(cyanomethyl)-4-methylpentanamide Chemical compound C(#N)CNC([C@H](N)CC(C)C)=O GQHJCLXWRQHKPT-SSDOTTSWSA-N 0.000 description 13
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 10
- 108090000790 Enzymes Proteins 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 150000003842 bromide salts Chemical class 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- ZZUXTLHHXTUBKA-UHFFFAOYSA-N 3-amino-n-[1-(cyanomethylamino)-4-methyl-1-oxopentan-2-yl]benzamide Chemical compound N#CCNC(=O)C(CC(C)C)NC(=O)C1=CC=CC(N)=C1 ZZUXTLHHXTUBKA-UHFFFAOYSA-N 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000012131 assay buffer Substances 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 238000010511 deprotection reaction Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000012085 test solution Substances 0.000 description 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
- XFKYKTBPRBZDFG-UHFFFAOYSA-N 2-aminoacetonitrile;hydrochloride Chemical compound Cl.NCC#N XFKYKTBPRBZDFG-UHFFFAOYSA-N 0.000 description 7
- 238000010790 dilution Methods 0.000 description 7
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- 230000000694 effects Effects 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 6
- OJPFWONQJWTJTI-UHFFFAOYSA-N 4-amino-N-[1-(cyanomethylamino)-4-methyl-1-oxopentan-2-yl]benzamide Chemical compound N#CCNC(=O)C(CC(C)C)NC(=O)C1=CC=C(N)C=C1 OJPFWONQJWTJTI-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 108090000712 Cathepsin B Proteins 0.000 description 6
- 102000004225 Cathepsin B Human genes 0.000 description 6
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 230000000670 limiting effect Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 230000001575 pathological effect Effects 0.000 description 6
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- UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 description 1
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- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
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- 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 1
- JNDZDNXOXWGQII-UHFFFAOYSA-N tert-butyl 4-[4-[(4-methoxycarbonylpiperidin-1-yl)methyl]-1,3-thiazol-2-yl]piperidine-1-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CC1=CSC(C2CCN(CC2)C(=O)OC(C)(C)C)=N1 JNDZDNXOXWGQII-UHFFFAOYSA-N 0.000 description 1
- GPCSKWXTSPEMSU-UHFFFAOYSA-N tert-butyl 4-[[2-(4-methoxycarbonylanilino)-1,3-thiazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NC(CN2CCN(CC2)C(=O)OC(C)(C)C)=CS1 GPCSKWXTSPEMSU-UHFFFAOYSA-N 0.000 description 1
- JBKRAGACGOPWFP-UHFFFAOYSA-N tert-butyl 4-carbamothioylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(N)=S)CC1 JBKRAGACGOPWFP-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
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- C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- 2001-10-12 HR HR20010737A patent/HRP20010737A2/hr not_active Application Discontinuation
- 2001-10-12 HR HR20010738A patent/HRP20010738B1/xx not_active IP Right Cessation
- 2001-12-14 US US10/017,851 patent/US6593327B2/en not_active Expired - Fee Related
-
2002
- 2002-01-18 HK HK02100444.0A patent/HK1039108A1/zh unknown
- 2002-07-24 US US10/205,600 patent/US20030096796A1/en not_active Abandoned
- 2002-08-13 HK HK02105942A patent/HK1044755A1/xx not_active IP Right Cessation
- 2002-09-09 US US10/241,001 patent/US20030119788A1/en not_active Abandoned
-
2004
- 2004-01-15 US US10/758,893 patent/US20040147745A1/en not_active Abandoned
-
2006
- 2006-09-20 US US11/533,582 patent/US20070015755A1/en not_active Abandoned
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