TWI593688B - 泛素活化酶之吡唑并嘧啶基抑制劑 - Google Patents

Info

Publication number

TWI593688B

TWI593688B TW102105676A TW102105676A TWI593688B TW I593688 B TWI593688 B TW I593688B TW 102105676 A TW102105676 A TW 102105676A TW 102105676 A TW102105676 A TW 102105676A TW I593688 B TWI593688 B TW I593688B

Authority

TW

Taiwan

Prior art keywords

pyrimidin

pyrazolo

methyl ester

group

aminosulfonic acid

Prior art date

2012-02-17

Links

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• -1 Pyrazolopyrimidinyl Chemical group 0.000 title claims description 327
• 108010091546 Ubiquitin-Activating Enzymes Proteins 0.000 title description 46
• 102000018478 Ubiquitin-Activating Enzymes Human genes 0.000 title description 46
• 239000003112 inhibitor Substances 0.000 title description 17
• 150000001875 compounds Chemical class 0.000 claims description 226
• 150000004702 methyl esters Chemical class 0.000 claims description 181
• UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 161
• 239000002253 acid Substances 0.000 claims description 153
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 115
• 125000005843 halogen group Chemical group 0.000 claims description 103
• 125000001931 aliphatic group Chemical group 0.000 claims description 94
• IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 92
• 150000005829 chemical entities Chemical class 0.000 claims description 87
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 79
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 43
• 206010028980 Neoplasm Diseases 0.000 claims description 40
• 125000003118 aryl group Chemical group 0.000 claims description 40
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 33
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 33
• 125000000623 heterocyclic group Chemical group 0.000 claims description 33
• 125000001072 heteroaryl group Chemical group 0.000 claims description 32
• 201000011510 cancer Diseases 0.000 claims description 31
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000002837 carbocyclic group Chemical group 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 238000011282 treatment Methods 0.000 claims description 21
• 150000004682 monohydrates Chemical class 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 18
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 230000005764 inhibitory process Effects 0.000 claims description 15
• 238000006467 substitution reaction Methods 0.000 claims description 15
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 12
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 12
• 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 10
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 9
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 7
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• 201000005202 lung cancer Diseases 0.000 claims description 6
• 208000020816 lung neoplasm Diseases 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 206010009944 Colon cancer Diseases 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 5
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• QCPOIDRINIAUKU-SRBBEKPSSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[(2-naphthalen-1-ylpyrazolo[1,5-a]pyrimidin-7-yl)amino]cyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C4=CC=CC=C4C=CC=3)=NN12 QCPOIDRINIAUKU-SRBBEKPSSA-N 0.000 claims description 4
• 208000029742 colonic neoplasm Diseases 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• PZOHRIXWJNTDKJ-TXEWCOSVSA-N [(1r,2r,3s,4r)-4-[(5-chloro-2-naphthalen-1-ylpyrazolo[1,5-a]pyrimidin-7-yl)amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC(Cl)=NC2=CC(C=3C4=CC=CC=C4C=CC=3)=NN12 PZOHRIXWJNTDKJ-TXEWCOSVSA-N 0.000 claims description 3
• XZDNWFAFRLQQDX-FCNFAXOHSA-N [(1r,2r,3s,4r)-4-[[2-(3-ethynylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(C=CC=3)C#C)=NN12 XZDNWFAFRLQQDX-FCNFAXOHSA-N 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
• HSQSIEIPMZGXCI-QBJHHKJPSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[2-(2-phenoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino]cyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C(=CC=CC=3)OC=3C=CC=CC=3)=NN12 HSQSIEIPMZGXCI-QBJHHKJPSA-N 0.000 claims description 2
• HRSBOFUEDXCMBN-RWJCITIMSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[2-(3-phenoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino]cyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(OC=4C=CC=CC=4)C=CC=3)=NN12 HRSBOFUEDXCMBN-RWJCITIMSA-N 0.000 claims description 2
• SYJSIKOBBZVNJB-IBKQYLNMSA-N [(1r,2r,3s,4r)-4-[(5-chloro-2-phenylpyrazolo[1,5-a]pyrimidin-7-yl)amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC(Cl)=NC2=CC(C=3C=CC=CC=3)=NN12 SYJSIKOBBZVNJB-IBKQYLNMSA-N 0.000 claims description 2
• YKXAYIRICCLAQW-ZULDRFPXSA-N [(1r,2r,3s,4r)-4-[[2-(2,4-dichlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C(=CC(Cl)=CC=3)Cl)=NN12 YKXAYIRICCLAQW-ZULDRFPXSA-N 0.000 claims description 2
• HVBJVLOBMWYYOB-SPRUFDBQSA-N [(1r,2r,3s,4r)-4-[[2-[3-(cyclopropylmethylsulfanyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(SCC4CC4)C=CC=3)=NN12 HVBJVLOBMWYYOB-SPRUFDBQSA-N 0.000 claims description 2
• NXZQFYVLPBGRDK-GMNOIFNYSA-N [(1r,2r,3s,4r)-4-[[2-[5-chloro-2-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C(=CC=C(Cl)C=3)OC(F)(F)F)=NN12 NXZQFYVLPBGRDK-GMNOIFNYSA-N 0.000 claims description 2
• 125000004145 cyclopenten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• 201000009613 breast lymphoma Diseases 0.000 claims 3
• SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
• RRSYSNJGDYQWLR-IHHCABKOSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[2-(2-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino]cyclopentyl]methyl sulfamate Chemical compound COC1=CC=CC=C1C1=NN2C(N[C@H]3[C@@H]([C@H](O)[C@@H](COS(N)(=O)=O)C3)O)=CC=NC2=C1 RRSYSNJGDYQWLR-IHHCABKOSA-N 0.000 claims 1
• ZDZZITXJLONZJL-SAVREHANSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[2-(3-pyridin-2-ylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino]cyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(C=CC=3)C=3N=CC=CC=3)=NN12 ZDZZITXJLONZJL-SAVREHANSA-N 0.000 claims 1
• ODKUMVDDQKSXSW-BGOALBTHSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[2-[2-(trifluoromethylsulfanyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]amino]cyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C(=CC=CC=3)SC(F)(F)F)=NN12 ODKUMVDDQKSXSW-BGOALBTHSA-N 0.000 claims 1
• CVVPJYPKTBTYGX-GBALOUKSSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[2-[2-methoxy-5-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]amino]cyclopentyl]methyl sulfamate Chemical compound COC1=CC=C(OC(F)(F)F)C=C1C1=NN2C(N[C@H]3[C@@H]([C@H](O)[C@@H](COS(N)(=O)=O)C3)O)=CC=NC2=C1 CVVPJYPKTBTYGX-GBALOUKSSA-N 0.000 claims 1
• VDKQLCNDZXRJOC-DGWLBADLSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[2-[3-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]amino]cyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(OC(F)(F)F)C=CC=3)=NN12 VDKQLCNDZXRJOC-DGWLBADLSA-N 0.000 claims 1
• YFTJRTRZJVPEGW-DGWLBADLSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[2-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]amino]cyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(C=CC=3)C(F)(F)F)=NN12 YFTJRTRZJVPEGW-DGWLBADLSA-N 0.000 claims 1
• KJDAGXLMHXUAGV-DGWLBADLSA-N [(1r,2r,3s,4r)-2,3-dihydroxy-4-[[2-[3-(trifluoromethylsulfanyl)phenyl]pyrazolo[1,5-a]pyrimidin-7-yl]amino]cyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(SC(F)(F)F)C=CC=3)=NN12 KJDAGXLMHXUAGV-DGWLBADLSA-N 0.000 claims 1
• XBFRVNJVAJTVDV-PPZUDANNSA-N [(1r,2r,3s,4r)-4-[[2-(3-benzylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(CC=4C=CC=CC=4)C=CC=3)=NN12 XBFRVNJVAJTVDV-PPZUDANNSA-N 0.000 claims 1
• KUHKFAQORFAPCV-DGWLBADLSA-N [(1r,2r,3s,4r)-4-[[2-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(Cl)C=CC=3)=NN12 KUHKFAQORFAPCV-DGWLBADLSA-N 0.000 claims 1
• KSGRGEPWGIAWEM-BAJOOJPFSA-N [(1r,2r,3s,4r)-4-[[2-(3-cyclopentylphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound O[C@@H]1[C@H](O)[C@@H](COS(=O)(=O)N)C[C@H]1NC1=CC=NC2=CC(C=3C=C(C=CC=3)C3CCCC3)=NN12 KSGRGEPWGIAWEM-BAJOOJPFSA-N 0.000 claims 1
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
• 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 237
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 202
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 144
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 124
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
• 239000000203 mixture Substances 0.000 description 79
• 238000000034 method Methods 0.000 description 66
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 54
• 239000000243 solution Substances 0.000 description 47
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 37
• 102000044159 Ubiquitin Human genes 0.000 description 34
• 108090000848 Ubiquitin Proteins 0.000 description 34
• 238000000634 powder X-ray diffraction Methods 0.000 description 34
• 125000004432 carbon atom Chemical group C* 0.000 description 32
• 235000019439 ethyl acetate Nutrition 0.000 description 32
• 238000001069 Raman spectroscopy Methods 0.000 description 28
• 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 27
• 238000006243 chemical reaction Methods 0.000 description 27
• 235000019253 formic acid Nutrition 0.000 description 27
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
• 239000011541 reaction mixture Substances 0.000 description 25
• 210000004027 cell Anatomy 0.000 description 24
• UFDGEFUTYSMTPD-UHFFFAOYSA-N 1-chloro-4-iodonaphthalene Chemical compound C1=CC=C2C(Cl)=CC=C(I)C2=C1 UFDGEFUTYSMTPD-UHFFFAOYSA-N 0.000 description 23
• 230000015572 biosynthetic process Effects 0.000 description 23
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
• 239000007787 solid Substances 0.000 description 22
• 238000003786 synthesis reaction Methods 0.000 description 22
• 239000000460 chlorine Substances 0.000 description 21
• 230000000694 effects Effects 0.000 description 21
• 239000000523 sample Substances 0.000 description 20
• 239000000725 suspension Substances 0.000 description 20
• 239000002585 base Substances 0.000 description 19
• 150000002148 esters Chemical class 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• 125000003342 alkenyl group Chemical group 0.000 description 17
• 239000012044 organic layer Substances 0.000 description 17
• 239000002904 solvent Substances 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 125000005842 heteroatom Chemical group 0.000 description 15
• 238000002411 thermogravimetry Methods 0.000 description 15
• 238000000113 differential scanning calorimetry Methods 0.000 description 14
• 239000013058 crude material Substances 0.000 description 13
• 102000004169 proteins and genes Human genes 0.000 description 13
• 108090000623 proteins and genes Proteins 0.000 description 13
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• 125000006413 ring segment Chemical group 0.000 description 12
• 238000001228 spectrum Methods 0.000 description 12
• 125000000304 alkynyl group Chemical group 0.000 description 11
• 238000004458 analytical method Methods 0.000 description 11
• 125000001309 chloro group Chemical group Cl* 0.000 description 11
• 238000004440 column chromatography Methods 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 229940124597 therapeutic agent Drugs 0.000 description 11
• 102000004190 Enzymes Human genes 0.000 description 10
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• 239000002552 dosage form Substances 0.000 description 10
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
• 239000000463 material Substances 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 9
• 239000003480 eluent Substances 0.000 description 9
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• 229920006395 saturated elastomer Polymers 0.000 description 9
• 210000001519 tissue Anatomy 0.000 description 9
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 230000004913 activation Effects 0.000 description 8
• 125000003545 alkoxy group Chemical group 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 8
• 230000008878 coupling Effects 0.000 description 8
• 238000010168 coupling process Methods 0.000 description 8
• 238000005859 coupling reaction Methods 0.000 description 8
• 208000035475 disorder Diseases 0.000 description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
• 229910052731 fluorine Inorganic materials 0.000 description 8
• 230000034512 ubiquitination Effects 0.000 description 8
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
• 125000004414 alkyl thio group Chemical group 0.000 description 7
• 239000012267 brine Substances 0.000 description 7
• 230000006870 function Effects 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 150000002430 hydrocarbons Chemical group 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 230000007111 proteostasis Effects 0.000 description 7
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
• 238000001757 thermogravimetry curve Methods 0.000 description 7
• 238000010798 ubiquitination Methods 0.000 description 7
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