JP2015531399A5 - - Google Patents
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- JP2015531399A5 JP2015531399A5 JP2015535842A JP2015535842A JP2015531399A5 JP 2015531399 A5 JP2015531399 A5 JP 2015531399A5 JP 2015535842 A JP2015535842 A JP 2015535842A JP 2015535842 A JP2015535842 A JP 2015535842A JP 2015531399 A5 JP2015531399 A5 JP 2015531399A5
- Authority
- JP
- Japan
- Prior art keywords
- chloromethyl
- methyl
- carbonate
- benzyl
- pyrimidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 3-methylbut-2-yl Chemical group 0.000 claims description 122
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229940079593 drug Drugs 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- MCEUCOMSCDMLPY-UHFFFAOYSA-N piperazin-1-ium;iodide Chemical compound I.C1CNCCN1 MCEUCOMSCDMLPY-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 230000002496 gastric effect Effects 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
- 230000009885 systemic effect Effects 0.000 claims description 6
- 208000035143 Bacterial infection Diseases 0.000 claims description 5
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 5
- 229940006461 iodide ion Drugs 0.000 claims description 5
- 230000003533 narcotic effect Effects 0.000 claims description 5
- 230000009385 viral infection Effects 0.000 claims description 5
- 241000701022 Cytomegalovirus Species 0.000 claims description 4
- 206010014614 Encephalitis western equine Diseases 0.000 claims description 4
- 241000829111 Human polyomavirus 1 Species 0.000 claims description 4
- 241000701460 JC polyomavirus Species 0.000 claims description 4
- 241000829100 Macaca mulatta polyomavirus 1 Species 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 208000005466 Western Equine Encephalomyelitis Diseases 0.000 claims description 4
- 201000005806 Western equine encephalitis Diseases 0.000 claims description 4
- LIUVJDYRXDXLJM-XXIQNXCHSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl [(1r)-1-phenylethyl] carbonate;iodide Chemical compound [I-].O([C@H](C)C=1C=CC=CC=1)C(=O)OC[N+](CC1)(C)CCN1CC(C=C1)=CC=C1C(=O)NC(C=1)=CC=C(C)C=1NC(N=1)=NC=CC=1C1=CC=CN=C1 LIUVJDYRXDXLJM-XXIQNXCHSA-N 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 4
- 239000000730 antalgic agent Substances 0.000 claims description 4
- 239000003242 anti bacterial agent Substances 0.000 claims description 4
- 239000003443 antiviral agent Substances 0.000 claims description 4
- BEPWYFBLGRQFFK-UHFFFAOYSA-N benzyl chloromethyl carbonate Chemical compound ClCOC(=O)OCC1=CC=CC=C1 BEPWYFBLGRQFFK-UHFFFAOYSA-N 0.000 claims description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- RJRPATMXXHZXSS-QMMMGPOBSA-N chloromethyl (2s)-2-phenylpropanoate Chemical compound ClCOC(=O)[C@@H](C)C1=CC=CC=C1 RJRPATMXXHZXSS-QMMMGPOBSA-N 0.000 claims description 4
- VHFSAFNPXFRUNE-KNVOCYPGSA-N chloromethyl (3r,5s)-3,5-dimethylmorpholine-4-carboxylate Chemical compound C[C@H]1COC[C@@H](C)N1C(=O)OCCl VHFSAFNPXFRUNE-KNVOCYPGSA-N 0.000 claims description 4
- AKJJZVNFZRSROB-UHFFFAOYSA-N chloromethyl 2-cyclohexylacetate Chemical compound ClCOC(=O)CC1CCCCC1 AKJJZVNFZRSROB-UHFFFAOYSA-N 0.000 claims description 4
- NLTCPNKKJDMJQD-UHFFFAOYSA-N chloromethyl 2-methylpropyl carbonate Chemical compound CC(C)COC(=O)OCCl NLTCPNKKJDMJQD-UHFFFAOYSA-N 0.000 claims description 4
- PTKGHLJGSLKWAM-UHFFFAOYSA-N chloromethyl piperidine-1-carboxylate Chemical compound ClCOC(=O)N1CCCCC1 PTKGHLJGSLKWAM-UHFFFAOYSA-N 0.000 claims description 4
- 239000008141 laxative Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 230000001850 reproductive effect Effects 0.000 claims description 4
- 230000002485 urinary effect Effects 0.000 claims description 4
- OVSDBIRVVIPYHU-AKGZTFGVSA-N CCC(C)[C@H](OC(=O)O)Cl Chemical compound CCC(C)[C@H](OC(=O)O)Cl OVSDBIRVVIPYHU-AKGZTFGVSA-N 0.000 claims description 3
- 241001115402 Ebolavirus Species 0.000 claims description 3
- 208000000832 Equine Encephalomyelitis Diseases 0.000 claims description 3
- 241000315672 SARS coronavirus Species 0.000 claims description 3
- 241000700605 Viruses Species 0.000 claims description 3
- 241000710886 West Nile virus Species 0.000 claims description 3
- 239000002535 acidifier Substances 0.000 claims description 3
- 239000000812 cholinergic antagonist Substances 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 230000002124 endocrine Effects 0.000 claims description 3
- 239000005556 hormone Substances 0.000 claims description 3
- 229940088597 hormone Drugs 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000003158 myorelaxant agent Substances 0.000 claims description 3
- 230000001613 neoplastic effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- PQQDLOKWXXFJOX-UHFFFAOYSA-N (2-chloro-1-morpholin-4-ylethyl) hydrogen carbonate Chemical compound OC(=O)OC(CCl)N1CCOCC1 PQQDLOKWXXFJOX-UHFFFAOYSA-N 0.000 claims description 2
- BGTMSNPWOMYNSZ-GSVOUGTGSA-N (2r)-2-amino-3-(chloromethoxycarbonyloxy)propanoic acid Chemical compound OC(=O)[C@H](N)COC(=O)OCCl BGTMSNPWOMYNSZ-GSVOUGTGSA-N 0.000 claims description 2
- ANVWVMSMDZIWRG-SECBINFHSA-N (2r)-2-amino-3-[4-(chloromethoxycarbonyloxy)phenyl]propanoic acid Chemical compound OC(=O)[C@H](N)CC1=CC=C(OC(=O)OCCl)C=C1 ANVWVMSMDZIWRG-SECBINFHSA-N 0.000 claims description 2
- WBWRWQOPPWZRMN-GSVOUGTGSA-N (2r)-2-amino-4-(chloromethoxycarbonyloxy)-4-oxobutanoic acid Chemical compound OC(=O)[C@H](N)CC(=O)OC(=O)OCCl WBWRWQOPPWZRMN-GSVOUGTGSA-N 0.000 claims description 2
- AEUFPTZGUQTJFO-SVGQVSJJSA-N (6r,7r)-7-(chloromethoxycarbonylamino)-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(OC)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)OCCl)[C@@H]12 AEUFPTZGUQTJFO-SVGQVSJJSA-N 0.000 claims description 2
- YKJXCOGADLWPCC-DRGSQQHPSA-N (6s)-3-chloro-7-(chloromethoxycarbonylamino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(Cl)CS[C@H]2C(NC(=O)OCCl)C(=O)N12 YKJXCOGADLWPCC-DRGSQQHPSA-N 0.000 claims description 2
- KAOWSQIAWSBJNZ-HSOSERFQSA-N (6s)-7-(chloromethoxycarbonylamino)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC)=C(C(O)=O)N2C(=O)C(NC(=O)OCCl)[C@H]12 KAOWSQIAWSBJNZ-HSOSERFQSA-N 0.000 claims description 2
- MIUCSCSKGLAGLV-HSOSERFQSA-N (6s)-7-(chloromethoxycarbonylamino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(C=C)CS[C@H]2C(NC(=O)OCCl)C(=O)N12 MIUCSCSKGLAGLV-HSOSERFQSA-N 0.000 claims description 2
- ZQOOVHOUNIFUBM-UHFFFAOYSA-N 1-chlorobutan-2-yl carbamate Chemical compound CCC(CCl)OC(N)=O ZQOOVHOUNIFUBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- ZONFEXLAEHDNNN-UHFFFAOYSA-N 1-o-(chloromethyl) 3-o-ethyl 2-oxopiperidine-1,3-dicarboxylate Chemical compound CCOC(=O)C1CCCN(C(=O)OCCl)C1=O ZONFEXLAEHDNNN-UHFFFAOYSA-N 0.000 claims description 2
- ARDPZBKTKOALJH-UHFFFAOYSA-N 1-o-(chloromethyl) 5-o-methyl 6-methyl-3,6-dihydro-2h-pyridine-1,5-dicarboxylate Chemical compound COC(=O)C1=CCCN(C(=O)OCCl)C1C ARDPZBKTKOALJH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- SDNLBDZOXQSXAP-UHFFFAOYSA-N 3-methylbutan-2-yl [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl carbonate;iodide Chemical compound [I-].C1C[N+](COC(=O)OC(C)C(C)C)(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 SDNLBDZOXQSXAP-UHFFFAOYSA-N 0.000 claims description 2
- OQBUKOLKICZMBY-UHFFFAOYSA-N 4-(chloromethoxycarbonyloxy)-2-hydroxy-4-oxobutanoic acid Chemical compound OC(=O)C(O)CC(=O)OC(=O)OCCl OQBUKOLKICZMBY-UHFFFAOYSA-N 0.000 claims description 2
- WLWBIKIIELTQHG-UHFFFAOYSA-N 4-methylbenzenesulfonate;[1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl 2-phenylacetate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=C(NC=2N=C(C=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)C(C=C1)=CC=C1CN(CC1)CC[N+]1(C)COC(=O)CC1=CC=CC=C1 WLWBIKIIELTQHG-UHFFFAOYSA-N 0.000 claims description 2
- NNPUCBBWOKKHDE-UHFFFAOYSA-N 4-methylbenzenesulfonate;piperazin-1-ium Chemical compound C1C[NH2+]CCN1.CC1=CC=C(S([O-])(=O)=O)C=C1 NNPUCBBWOKKHDE-UHFFFAOYSA-N 0.000 claims description 2
- HYOXVHNJEFRGBX-RJNKSYOCSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoyl 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoate Chemical compound N([C@H]1CS2)C(=O)N[C@@H]1[C@@H]2CCCCC(=O)OC(=O)CCCC[C@H]1[C@H]2NC(=O)N[C@H]2CS1 HYOXVHNJEFRGBX-RJNKSYOCSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 241000710929 Alphavirus Species 0.000 claims description 2
- 241000712891 Arenavirus Species 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- DNGWLWFSXHDKAI-RNJXMRFFSA-N C1C[C@@]2([H])[C@@H](NC(=O)OCCl)C[C@]1([H])C2 Chemical compound C1C[C@@]2([H])[C@@H](NC(=O)OCCl)C[C@]1([H])C2 DNGWLWFSXHDKAI-RNJXMRFFSA-N 0.000 claims description 2
- 206010007027 Calculus urinary Diseases 0.000 claims description 2
- 229930186147 Cephalosporin Natural products 0.000 claims description 2
- 241000606161 Chlamydia Species 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 241000588724 Escherichia coli Species 0.000 claims description 2
- 241000590002 Helicobacter pylori Species 0.000 claims description 2
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 claims description 2
- 101000823316 Homo sapiens Tyrosine-protein kinase ABL1 Proteins 0.000 claims description 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 2
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 2
- 241000186779 Listeria monocytogenes Species 0.000 claims description 2
- 241001115401 Marburgvirus Species 0.000 claims description 2
- 241000700627 Monkeypox virus Species 0.000 claims description 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 2
- 241000713112 Orthobunyavirus Species 0.000 claims description 2
- 229930182555 Penicillin Natural products 0.000 claims description 2
- 241001505332 Polyomavirus sp. Species 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 2
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims description 2
- 241000607762 Shigella flexneri Species 0.000 claims description 2
- 239000000150 Sympathomimetic Substances 0.000 claims description 2
- 239000004098 Tetracycline Substances 0.000 claims description 2
- 102100022596 Tyrosine-protein kinase ABL1 Human genes 0.000 claims description 2
- 206010046543 Urinary incontinence Diseases 0.000 claims description 2
- 206010046555 Urinary retention Diseases 0.000 claims description 2
- 241000700618 Vaccinia virus Species 0.000 claims description 2
- 241000700647 Variola virus Species 0.000 claims description 2
- UAYJEWDZMLLUHZ-AKGZTFGVSA-N [(2R)-2-(chloromethyl)oxolan-3-yl] hydrogen carbonate Chemical compound OC(=O)OC1CCO[C@H]1CCl UAYJEWDZMLLUHZ-AKGZTFGVSA-N 0.000 claims description 2
- UAYJEWDZMLLUHZ-BRJRFNKRSA-N [(2S)-2-(chloromethyl)oxolan-3-yl] hydrogen carbonate Chemical compound OC(=O)OC1CCO[C@@H]1CCl UAYJEWDZMLLUHZ-BRJRFNKRSA-N 0.000 claims description 2
- FAIWMYPDZUXZEE-YFKPBYRVSA-N [(2s)-butan-2-yl] chloromethyl carbonate Chemical compound CC[C@H](C)OC(=O)OCCl FAIWMYPDZUXZEE-YFKPBYRVSA-N 0.000 claims description 2
- XWVGKIGDAIRTSQ-UHFFFAOYSA-N [(3-tert-butyl-4-methoxyphenyl)-chloromethyl] hydrogen carbonate Chemical compound COc1ccc(cc1C(C)(C)C)C(Cl)OC(O)=O XWVGKIGDAIRTSQ-UHFFFAOYSA-N 0.000 claims description 2
- ILMLHBWSXGNEAT-BHQGJQQGSA-N [(R)-[(2S,4S)-2-bicyclo[2.2.1]heptanyl]-chloromethyl] hydrogen carbonate Chemical compound OC(=O)O[C@H](Cl)[C@H]1C[C@H]2CCC1C2 ILMLHBWSXGNEAT-BHQGJQQGSA-N 0.000 claims description 2
- RLLKBWJTCZYVCU-UHFFFAOYSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl 2,2-dimethylbutanoate;iodide Chemical compound [I-].C1C[N+](COC(=O)C(C)(C)CC)(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 RLLKBWJTCZYVCU-UHFFFAOYSA-N 0.000 claims description 2
- HAGWPPIISVKXPQ-UHFFFAOYSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl 2-methylpropanoate;iodide Chemical compound [I-].C1C[N+](COC(=O)C(C)C)(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 HAGWPPIISVKXPQ-UHFFFAOYSA-N 0.000 claims description 2
- YTRSSXIJSQLFAO-UHFFFAOYSA-O [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl 2-phenylacetate;nitrate Chemical compound [O-][N+]([O-])=O.C1=C(NC=2N=C(C=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)C(C=C1)=CC=C1CN(CC1)CC[N+]1(C)COC(=O)CC1=CC=CC=C1 YTRSSXIJSQLFAO-UHFFFAOYSA-O 0.000 claims description 2
- ZEVCHRSSKIKXKU-UHFFFAOYSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl 2-phenylacetate;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=C(NC=2N=C(C=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)C(C=C1)=CC=C1CN(CC1)CC[N+]1(C)COC(=O)CC1=CC=CC=C1 ZEVCHRSSKIKXKU-UHFFFAOYSA-N 0.000 claims description 2
- ITZMJLBKQFPNEB-UHFFFAOYSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl 2-phenylpropanoate;iodide Chemical compound [I-].C=1C=CC=CC=1C(C)C(=O)OC[N+](CC1)(C)CCN1CC(C=C1)=CC=C1C(=O)NC(C=1)=CC=C(C)C=1NC(N=1)=NC=CC=1C1=CC=CN=C1 ITZMJLBKQFPNEB-UHFFFAOYSA-N 0.000 claims description 2
- FOGBVZHICMRCFB-UHFFFAOYSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl 3-methylbutanoate;iodide Chemical compound [I-].C1C[N+](COC(=O)CC(C)C)(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 FOGBVZHICMRCFB-UHFFFAOYSA-N 0.000 claims description 2
- CGTJXBKMGQHERM-UHFFFAOYSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl morpholine-4-carboxylate;iodide Chemical compound [I-].C1=C(NC=2N=C(C=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)C(C=C1)=CC=C1CN(CC1)CC[N+]1(C)COC(=O)N1CCOCC1 CGTJXBKMGQHERM-UHFFFAOYSA-N 0.000 claims description 2
- GONTYOKQBSULEO-XXIQNXCHSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl n-[(1r)-1-phenylethyl]carbamate;iodide Chemical compound [I-].N([C@H](C)C=1C=CC=CC=1)C(=O)OC[N+](CC1)(C)CCN1CC(C=C1)=CC=C1C(=O)NC(C=1)=CC=C(C)C=1NC(N=1)=NC=CC=1C1=CC=CN=C1 GONTYOKQBSULEO-XXIQNXCHSA-N 0.000 claims description 2
- GONTYOKQBSULEO-JMAPEOGHSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl n-[(1s)-1-phenylethyl]carbamate;iodide Chemical compound [I-].N([C@@H](C)C=1C=CC=CC=1)C(=O)OC[N+](CC1)(C)CCN1CC(C=C1)=CC=C1C(=O)NC(C=1)=CC=C(C)C=1NC(N=1)=NC=CC=1C1=CC=CN=C1 GONTYOKQBSULEO-JMAPEOGHSA-N 0.000 claims description 2
- PYZURCKWGOOING-UHFFFAOYSA-N [1-methyl-4-[[4-[[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]carbamoyl]phenyl]methyl]piperazin-1-ium-1-yl]methyl n-propan-2-ylcarbamate;iodide Chemical compound [I-].C1C[N+](COC(=O)NC(C)C)(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 PYZURCKWGOOING-UHFFFAOYSA-N 0.000 claims description 2
- SFUHGODWABYWSJ-UHFFFAOYSA-N [2-(chloromethyl)oxan-4-yl] hydrogen carbonate Chemical compound OC(=O)OC1CCOC(CCl)C1 SFUHGODWABYWSJ-UHFFFAOYSA-N 0.000 claims description 2
- JMOLVBNSKJEGDL-UHFFFAOYSA-N [2-(chloromethyl)oxepan-4-yl] hydrogen carbonate Chemical compound OC(=O)OC1CCCOC(CCl)C1 JMOLVBNSKJEGDL-UHFFFAOYSA-N 0.000 claims description 2
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- SIIUCPOQSRHWKP-UHFFFAOYSA-N chloromethyl 1-cyclopentylethyl carbonate Chemical compound ClCOC(=O)OC(C)C1CCCC1 SIIUCPOQSRHWKP-UHFFFAOYSA-N 0.000 claims description 2
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- NJVVZVLPAPHXMK-UHFFFAOYSA-N chloromethyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OCCl NJVVZVLPAPHXMK-UHFFFAOYSA-N 0.000 claims description 2
- GKVPZOGIVLGMHD-UHFFFAOYSA-N chloromethyl 2,2,6,6-tetramethyl-4-oxopiperidine-1-carboxylate Chemical compound CC1(C)CC(=O)CC(C)(C)N1C(=O)OCCl GKVPZOGIVLGMHD-UHFFFAOYSA-N 0.000 claims description 2
- MMBUPQHJAZPRBF-UHFFFAOYSA-N chloromethyl 2,2-diethoxyethyl carbonate Chemical compound CCOC(OCC)COC(=O)OCCl MMBUPQHJAZPRBF-UHFFFAOYSA-N 0.000 claims description 2
- FDOKMWOVZVHOIF-UHFFFAOYSA-N chloromethyl 2,2-difluoroacetate Chemical compound FC(F)C(=O)OCCl FDOKMWOVZVHOIF-UHFFFAOYSA-N 0.000 claims description 2
- CKVJTTAYFWQVRS-UHFFFAOYSA-N chloromethyl 2,2-dimethylbutanoate Chemical compound CCC(C)(C)C(=O)OCCl CKVJTTAYFWQVRS-UHFFFAOYSA-N 0.000 claims description 2
- VOYXHVPLPQAGKJ-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropyl carbonate Chemical compound CC(C)(C)COC(=O)OCCl VOYXHVPLPQAGKJ-UHFFFAOYSA-N 0.000 claims description 2
- KYYMJEPYOQURGW-UHFFFAOYSA-N chloromethyl 2,3-dihydro-1h-inden-1-yl carbonate Chemical compound C1=CC=C2C(OC(=O)OCCl)CCC2=C1 KYYMJEPYOQURGW-UHFFFAOYSA-N 0.000 claims description 2
- BNSIGFYDTWRSFI-UHFFFAOYSA-N chloromethyl 2-(1-methylcyclobutyl)acetate Chemical compound ClCOC(=O)CC1(C)CCC1 BNSIGFYDTWRSFI-UHFFFAOYSA-N 0.000 claims description 2
- CABJHQHPXXLUBR-UHFFFAOYSA-N chloromethyl 2-cyanopyrrole-1-carboxylate Chemical compound ClCOC(=O)N1C=CC=C1C#N CABJHQHPXXLUBR-UHFFFAOYSA-N 0.000 claims description 2
- UVFLOGLBPPHREZ-UHFFFAOYSA-N chloromethyl 2-cyclobutylacetate Chemical compound ClCOC(=O)CC1CCC1 UVFLOGLBPPHREZ-UHFFFAOYSA-N 0.000 claims description 2
- PGUCFXJKDKACMW-UHFFFAOYSA-N chloromethyl 2-cyclopentylacetate Chemical compound ClCOC(=O)CC1CCCC1 PGUCFXJKDKACMW-UHFFFAOYSA-N 0.000 claims description 2
- YCUKZZYRTRKHNB-UHFFFAOYSA-N chloromethyl 2-cyclopropylacetate Chemical compound ClCOC(=O)CC1CC1 YCUKZZYRTRKHNB-UHFFFAOYSA-N 0.000 claims description 2
- AAACXXOAKLEEOX-UHFFFAOYSA-N chloromethyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OCCl AAACXXOAKLEEOX-UHFFFAOYSA-N 0.000 claims description 2
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- XIQFQYLHQIVRSP-UHFFFAOYSA-N chloromethyl 2-methoxyethyl carbonate Chemical compound COCCOC(=O)OCCl XIQFQYLHQIVRSP-UHFFFAOYSA-N 0.000 claims description 2
- MGAJDLGBTVHGNZ-UHFFFAOYSA-N chloromethyl 2-methylbutanoate Chemical compound CCC(C)C(=O)OCCl MGAJDLGBTVHGNZ-UHFFFAOYSA-N 0.000 claims description 2
- CQZQJUALVVBGPE-UHFFFAOYSA-N chloromethyl 2-methylcyclopropane-1-carboxylate Chemical compound CC1CC1C(=O)OCCl CQZQJUALVVBGPE-UHFFFAOYSA-N 0.000 claims description 2
- NAIOHKKOIKOYJK-UHFFFAOYSA-N chloromethyl 2-methylpentanoate Chemical compound CCCC(C)C(=O)OCCl NAIOHKKOIKOYJK-UHFFFAOYSA-N 0.000 claims description 2
- ILUWVORABZTBIU-UHFFFAOYSA-N chloromethyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCCl ILUWVORABZTBIU-UHFFFAOYSA-N 0.000 claims description 2
- YYCNPZAKBZUWFW-UHFFFAOYSA-N chloromethyl 2-oxopiperidine-1-carboxylate Chemical compound ClCOC(=O)N1CCCCC1=O YYCNPZAKBZUWFW-UHFFFAOYSA-N 0.000 claims description 2
- NADNXZCFRMBALJ-UHFFFAOYSA-N chloromethyl 2-phenylbutanoate Chemical compound ClCOC(=O)C(CC)C1=CC=CC=C1 NADNXZCFRMBALJ-UHFFFAOYSA-N 0.000 claims description 2
- RJRPATMXXHZXSS-UHFFFAOYSA-N chloromethyl 2-phenylpropanoate Chemical compound ClCOC(=O)C(C)C1=CC=CC=C1 RJRPATMXXHZXSS-UHFFFAOYSA-N 0.000 claims description 2
- KIXXNVIBZZJQFC-UHFFFAOYSA-N chloromethyl 2-propan-2-yloxyethyl carbonate Chemical compound CC(C)OCCOC(=O)OCCl KIXXNVIBZZJQFC-UHFFFAOYSA-N 0.000 claims description 2
- UKDNQXYTITZEEI-UHFFFAOYSA-N chloromethyl 2-propylpentanoate Chemical compound CCCC(CCC)C(=O)OCCl UKDNQXYTITZEEI-UHFFFAOYSA-N 0.000 claims description 2
- DECZFCGDZPWTSH-UHFFFAOYSA-N chloromethyl 3,5,5-trimethylhexanoate Chemical compound CC(C)(C)CC(C)CC(=O)OCCl DECZFCGDZPWTSH-UHFFFAOYSA-N 0.000 claims description 2
- ZDSUTFGZEQNBJA-UHFFFAOYSA-N chloromethyl 3,5-dimethylcyclohexane-1-carboxylate Chemical compound CC1CC(C)CC(C(=O)OCCl)C1 ZDSUTFGZEQNBJA-UHFFFAOYSA-N 0.000 claims description 2
- BNDXNOVGABUKDG-UHFFFAOYSA-N chloromethyl 3,7-dimethylocta-1,6-dien-3-yl carbonate Chemical compound CC(C)=CCCC(C)(C=C)OC(=O)OCCl BNDXNOVGABUKDG-UHFFFAOYSA-N 0.000 claims description 2
- AEANXUROVZGOPM-UHFFFAOYSA-N chloromethyl 3-(4-bromophenyl)pyrazole-1-carboxylate Chemical compound ClCOC(=O)N1C=CC(C=2C=CC(Br)=CC=2)=N1 AEANXUROVZGOPM-UHFFFAOYSA-N 0.000 claims description 2
- JPFOCZZDKMDZPV-UHFFFAOYSA-N chloromethyl 3-(4-chlorophenyl)pyrazole-1-carboxylate Chemical compound ClCOC(=O)N1C=CC(C=2C=CC(Cl)=CC=2)=N1 JPFOCZZDKMDZPV-UHFFFAOYSA-N 0.000 claims description 2
- FMHGDTGYXASJPE-UHFFFAOYSA-N chloromethyl 3-(4-fluorophenyl)pyrazole-1-carboxylate Chemical compound C1=CC(F)=CC=C1C1=NN(C(=O)OCCl)C=C1 FMHGDTGYXASJPE-UHFFFAOYSA-N 0.000 claims description 2
- WUEJDALLJUKQSL-UHFFFAOYSA-N chloromethyl 3-cyclohexylpropanoate Chemical compound ClCOC(=O)CCC1CCCCC1 WUEJDALLJUKQSL-UHFFFAOYSA-N 0.000 claims description 2
- YYXXWLULYWBKME-UHFFFAOYSA-N chloromethyl 3-cyclopentylpropanoate Chemical compound ClCOC(=O)CCC1CCCC1 YYXXWLULYWBKME-UHFFFAOYSA-N 0.000 claims description 2
- YYHNCJANZUSGKZ-UHFFFAOYSA-N chloromethyl 3-methoxyazetidine-1-carboxylate Chemical compound COC1CN(C(=O)OCCl)C1 YYHNCJANZUSGKZ-UHFFFAOYSA-N 0.000 claims description 2
- ZTUILWMNPFKKNU-UHFFFAOYSA-N chloromethyl 3-methoxycyclohexane-1-carboxylate Chemical compound COC1CCCC(C(=O)OCCl)C1 ZTUILWMNPFKKNU-UHFFFAOYSA-N 0.000 claims description 2
- FREZJJZSTYGDCD-UHFFFAOYSA-N chloromethyl 3-methyl-2-propan-2-ylbutanoate Chemical compound CC(C)C(C(C)C)C(=O)OCCl FREZJJZSTYGDCD-UHFFFAOYSA-N 0.000 claims description 2
- YPRHOYLAIXFISY-UHFFFAOYSA-N chloromethyl 3-methylbenzoate Chemical compound CC1=CC=CC(C(=O)OCCl)=C1 YPRHOYLAIXFISY-UHFFFAOYSA-N 0.000 claims description 2
- XDAODGDACJUZQS-UHFFFAOYSA-N chloromethyl 3-oxobutan-2-yl carbonate Chemical compound CC(=O)C(C)OC(=O)OCCl XDAODGDACJUZQS-UHFFFAOYSA-N 0.000 claims description 2
- FNKORMYAPQCQAU-UHFFFAOYSA-N chloromethyl 3-phenylpropanoate Chemical compound ClCOC(=O)CCC1=CC=CC=C1 FNKORMYAPQCQAU-UHFFFAOYSA-N 0.000 claims description 2
- LOJGINHKUDSFMP-UHFFFAOYSA-N chloromethyl 3-phenylpyrazole-1-carboxylate Chemical compound ClCOC(=O)N1C=CC(C=2C=CC=CC=2)=N1 LOJGINHKUDSFMP-UHFFFAOYSA-N 0.000 claims description 2
- TUUBZJJFTMCDMJ-UHFFFAOYSA-N chloromethyl 4,4-difluorocyclohexane-1-carboxylate Chemical compound FC1(F)CCC(C(=O)OCCl)CC1 TUUBZJJFTMCDMJ-UHFFFAOYSA-N 0.000 claims description 2
- RILHVTJTLBMNRW-UHFFFAOYSA-N chloromethyl 4-fluorobenzoate Chemical compound FC1=CC=C(C(=O)OCCl)C=C1 RILHVTJTLBMNRW-UHFFFAOYSA-N 0.000 claims description 2
- QMOBAVCASHSTEK-UHFFFAOYSA-N chloromethyl 4-methoxybenzoate Chemical compound COC1=CC=C(C(=O)OCCl)C=C1 QMOBAVCASHSTEK-UHFFFAOYSA-N 0.000 claims description 2
- PLSFCOSOHBUMJM-UHFFFAOYSA-N chloromethyl 4-methoxycyclohexane-1-carboxylate Chemical compound COC1CCC(C(=O)OCCl)CC1 PLSFCOSOHBUMJM-UHFFFAOYSA-N 0.000 claims description 2
- OTYHJHBXXQVLHK-UHFFFAOYSA-N chloromethyl 4-methylbenzoate Chemical compound CC1=CC=C(C(=O)OCCl)C=C1 OTYHJHBXXQVLHK-UHFFFAOYSA-N 0.000 claims description 2
- QYZUXNQHZUJSCM-UHFFFAOYSA-N chloromethyl 4-methylcyclohexane-1-carboxylate Chemical compound CC1CCC(C(=O)OCCl)CC1 QYZUXNQHZUJSCM-UHFFFAOYSA-N 0.000 claims description 2
- VFZFYNNBGDBIQP-UHFFFAOYSA-N chloromethyl 4-methylpiperazine-1-carboxylate Chemical compound CN1CCN(C(=O)OCCl)CC1 VFZFYNNBGDBIQP-UHFFFAOYSA-N 0.000 claims description 2
- JIDSHQQDCPHOJZ-UHFFFAOYSA-N chloromethyl 4-oxopiperidine-1-carboxylate Chemical compound ClCOC(=O)N1CCC(=O)CC1 JIDSHQQDCPHOJZ-UHFFFAOYSA-N 0.000 claims description 2
- WPAVBRUYTLXEID-UHFFFAOYSA-N chloromethyl 5,5-dimethyl-3-oxohexanoate Chemical compound CC(C)(C)CC(=O)CC(=O)OCCl WPAVBRUYTLXEID-UHFFFAOYSA-N 0.000 claims description 2
- IDDTZZTYVODXHH-OUAUKWLOSA-N chloromethyl [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] carbonate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)OCCl IDDTZZTYVODXHH-OUAUKWLOSA-N 0.000 claims description 2
- KPLRZVXTNPHYPD-QMMMGPOBSA-N chloromethyl [(1s)-1-phenylethyl] carbonate Chemical compound ClCOC(=O)O[C@@H](C)C1=CC=CC=C1 KPLRZVXTNPHYPD-QMMMGPOBSA-N 0.000 claims description 2
- SHHWJYCTAPYJCK-QMMMGPOBSA-N chloromethyl [(1s)-2,2,4-trimethylcyclopent-3-en-1-yl] carbonate Chemical compound CC1=CC(C)(C)[C@@H](OC(=O)OCCl)C1 SHHWJYCTAPYJCK-QMMMGPOBSA-N 0.000 claims description 2
- SMJYMSAPPGLBAR-UHFFFAOYSA-N chloromethyl acetate Chemical compound CC(=O)OCCl SMJYMSAPPGLBAR-UHFFFAOYSA-N 0.000 claims description 2
- PWFGJSQFSZRTLQ-UHFFFAOYSA-N chloromethyl azepane-1-carboxylate Chemical compound ClCOC(=O)N1CCCCCC1 PWFGJSQFSZRTLQ-UHFFFAOYSA-N 0.000 claims description 2
- SWIMRRJQXRFQEP-UHFFFAOYSA-N chloromethyl azetidine-1-carboxylate Chemical compound ClCOC(=O)N1CCC1 SWIMRRJQXRFQEP-UHFFFAOYSA-N 0.000 claims description 2
- FCZUUYNIDRIFHX-UHFFFAOYSA-N chloromethyl aziridine-1-carboxylate Chemical compound ClCOC(=O)N1CC1 FCZUUYNIDRIFHX-UHFFFAOYSA-N 0.000 claims description 2
- RMMJTPVYVFGTCD-UHFFFAOYSA-N chloromethyl bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylate Chemical compound C1=CC=C2C(C(=O)OCCl)CC2=C1 RMMJTPVYVFGTCD-UHFFFAOYSA-N 0.000 claims description 2
- BDPZFQLKFUONAG-UHFFFAOYSA-N chloromethyl butanoate Chemical compound CCCC(=O)OCCl BDPZFQLKFUONAG-UHFFFAOYSA-N 0.000 claims description 2
- ZOSJJKIXNSMVSJ-UHFFFAOYSA-N chloromethyl cyclobutanecarboxylate Chemical compound ClCOC(=O)C1CCC1 ZOSJJKIXNSMVSJ-UHFFFAOYSA-N 0.000 claims description 2
- MYYRBUPYHQNWMD-UHFFFAOYSA-N chloromethyl cyclobutyl carbonate Chemical compound ClCOC(=O)OC1CCC1 MYYRBUPYHQNWMD-UHFFFAOYSA-N 0.000 claims description 2
- ZFYFSEXLXRFOLD-UHFFFAOYSA-N chloromethyl cyclohexanecarboxylate Chemical compound ClCOC(=O)C1CCCCC1 ZFYFSEXLXRFOLD-UHFFFAOYSA-N 0.000 claims description 2
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| US9487500B2 (en) * | 2012-10-04 | 2016-11-08 | Inhibikase Therapeutics, Inc. | Compounds and compositions thereof |
| CN109700823B (zh) * | 2014-08-18 | 2021-07-06 | 中国医学科学院药物研究所 | 泰利霉素在抗埃博拉病毒感染中的应用 |
| JP6795518B2 (ja) | 2015-04-23 | 2020-12-02 | インヒビカーセ セラピューティクス，インコーポレーテッド | キナーゼを阻害する組成物及び方法 |
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| CN109180521B (zh) * | 2018-09-05 | 2021-08-31 | 中国人民解放军陆军军医大学 | 一种抗肿瘤化合物及其制备方法、用途 |
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