DE3122540A1 - In 3-stellung substituierte 2-propenimidamide und verfahren zu deren herstellung - Google Patents
In 3-stellung substituierte 2-propenimidamide und verfahren zu deren herstellungInfo
- Publication number
- DE3122540A1 DE3122540A1 DE19813122540 DE3122540A DE3122540A1 DE 3122540 A1 DE3122540 A1 DE 3122540A1 DE 19813122540 DE19813122540 DE 19813122540 DE 3122540 A DE3122540 A DE 3122540A DE 3122540 A1 DE3122540 A1 DE 3122540A1
- Authority
- DE
- Germany
- Prior art keywords
- propenimidamide
- cyano
- formula
- chlorophenyl
- compound
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- AXPUQAAUHKSVKR-UHFFFAOYSA-N prop-2-enimidamide Chemical group NC(=N)C=C AXPUQAAUHKSVKR-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 3-furyl- Chemical group 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 6
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 230000028327 secretion Effects 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 210000004051 gastric juice Anatomy 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims 3
- QURNIZVSEYGQSL-UHFFFAOYSA-N n-cyanoprop-2-enamide Chemical class C=CC(=O)NC#N QURNIZVSEYGQSL-UHFFFAOYSA-N 0.000 claims 2
- BXMQZGVLWACQGB-UHFFFAOYSA-N N'-cyanoprop-2-enimidamide Chemical compound C(#N)N=C(C=C)N BXMQZGVLWACQGB-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract description 3
- GDYXPZCCNRBQNS-UHFFFAOYSA-N 3-phenylprop-2-enimidamide Chemical class NC(=N)C=CC1=CC=CC=C1 GDYXPZCCNRBQNS-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003699 antiulcer agent Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JQDXRKWMURCIAL-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-cyano-n'-methylprop-2-enimidamide Chemical compound N#CN=C(NC)C=CC1=CC=CC=C1Cl JQDXRKWMURCIAL-UHFFFAOYSA-N 0.000 description 3
- 208000007107 Stomach Ulcer Diseases 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- OTTNYXZOYWVJLH-UHFFFAOYSA-N ethyl 3-(furan-2-yl)prop-2-enimidate Chemical compound CCOC(=N)C=CC1=CC=CO1 OTTNYXZOYWVJLH-UHFFFAOYSA-N 0.000 description 3
- YYRGWDSRYPGNHQ-UHFFFAOYSA-N ethyl 3-thiophen-2-ylprop-2-enimidate Chemical compound CCOC(=N)C=CC1=CC=CS1 YYRGWDSRYPGNHQ-UHFFFAOYSA-N 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- NQDWYJOLHBMRHH-UHFFFAOYSA-N n-cyano-3-(4-methoxyphenyl)-n'-(2-methylpropyl)prop-2-enimidamide Chemical compound COC1=CC=C(C=CC(NCC(C)C)=NC#N)C=C1 NQDWYJOLHBMRHH-UHFFFAOYSA-N 0.000 description 3
- JGADPKDZTNULHV-UHFFFAOYSA-N n-cyano-n'-methyl-3-phenylprop-2-enimidamide Chemical compound N#CN=C(NC)C=CC1=CC=CC=C1 JGADPKDZTNULHV-UHFFFAOYSA-N 0.000 description 3
- FABMEELZRQHGOL-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-cyano-n'-(2-methylpropyl)prop-2-enimidamide Chemical compound CC(C)CNC(=NC#N)C=CC1=CC=CC=C1Cl FABMEELZRQHGOL-UHFFFAOYSA-N 0.000 description 2
- AFICOWYBPBHEGF-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-cyano-n'-(4-methylcyclohexyl)prop-2-enimidamide Chemical compound C1CC(C)CCC1NC(=NC#N)C=CC1=CC=CC=C1Cl AFICOWYBPBHEGF-UHFFFAOYSA-N 0.000 description 2
- UXEZAMNUTOALCP-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-cyano-n'-cyclohexylprop-2-enimidamide Chemical compound ClC1=CC=CC=C1C=CC(=NC#N)NC1CCCCC1 UXEZAMNUTOALCP-UHFFFAOYSA-N 0.000 description 2
- JTCHRDKAJUQPLN-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-cyano-n'-ethylprop-2-enimidamide Chemical compound CCNC(=NC#N)C=CC1=CC=CC=C1Cl JTCHRDKAJUQPLN-UHFFFAOYSA-N 0.000 description 2
- XVIKTJVZQVDLNG-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-cyano-n'-propan-2-ylprop-2-enimidamide Chemical compound CC(C)NC(=NC#N)C=CC1=CC=CC=C1Cl XVIKTJVZQVDLNG-UHFFFAOYSA-N 0.000 description 2
- HTWOCQJQYFWCKY-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-cyano-n'-propylprop-2-enimidamide Chemical compound CCCNC(=NC#N)C=CC1=CC=CC=C1Cl HTWOCQJQYFWCKY-UHFFFAOYSA-N 0.000 description 2
- LGVZLJFAFXQVMA-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-cyano-n'-(2-methylpropyl)prop-2-enimidamide Chemical compound CC(C)CNC(=NC#N)C=CC1=CC=C(Cl)C=C1 LGVZLJFAFXQVMA-UHFFFAOYSA-N 0.000 description 2
- AMKPMEFRRXMLJQ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-cyano-n'-(4-methylcyclohexyl)prop-2-enimidamide Chemical compound C1CC(C)CCC1NC(=NC#N)C=CC1=CC=C(Cl)C=C1 AMKPMEFRRXMLJQ-UHFFFAOYSA-N 0.000 description 2
- FOUHRINERYVCSS-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-cyano-n'-cyclohexylprop-2-enimidamide Chemical compound C1=CC(Cl)=CC=C1C=CC(=NC#N)NC1CCCCC1 FOUHRINERYVCSS-UHFFFAOYSA-N 0.000 description 2
- ABJZJEOZEAANNK-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-cyano-n'-ethylprop-2-enimidamide Chemical compound CCNC(=NC#N)C=CC1=CC=C(Cl)C=C1 ABJZJEOZEAANNK-UHFFFAOYSA-N 0.000 description 2
- NZBVQELEGKMBEJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-cyano-n'-propan-2-ylprop-2-enimidamide Chemical compound CC(C)NC(=NC#N)C=CC1=CC=C(Cl)C=C1 NZBVQELEGKMBEJ-UHFFFAOYSA-N 0.000 description 2
- GKZBJHDWSAAIKL-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-cyano-n'-propylprop-2-enimidamide Chemical compound CCCNC(=NC#N)C=CC1=CC=C(Cl)C=C1 GKZBJHDWSAAIKL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IMJXKMYLQBXIKQ-UHFFFAOYSA-N [1-amino-3-(furan-2-yl)prop-2-enylidene]urea;hydrochloride Chemical compound Cl.NC(=O)N=C(N)C=CC1=CC=CO1 IMJXKMYLQBXIKQ-UHFFFAOYSA-N 0.000 description 2
- ATDWWLDNNGGUKZ-UHFFFAOYSA-N [c-(2-phenylethenyl)-n-propan-2-ylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.CC(C)NC(=NC(N)=O)C=CC1=CC=CC=C1 ATDWWLDNNGGUKZ-UHFFFAOYSA-N 0.000 description 2
- FVHOIBSGKDJHIE-UHFFFAOYSA-N [c-[2-(2-chlorophenyl)ethenyl]-n-(4-methylcyclohexyl)carbonimidoyl]urea;hydrochloride Chemical compound Cl.C1CC(C)CCC1NC(=NC(N)=O)C=CC1=CC=CC=C1Cl FVHOIBSGKDJHIE-UHFFFAOYSA-N 0.000 description 2
- BVWVFFLHKVEDRA-UHFFFAOYSA-N [c-[2-(2-chlorophenyl)ethenyl]-n-cyclohexylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1C=CC(=NC(=O)N)NC1CCCCC1 BVWVFFLHKVEDRA-UHFFFAOYSA-N 0.000 description 2
- BOKAQVGFWBVFNR-UHFFFAOYSA-N [c-[2-(2-chlorophenyl)ethenyl]-n-ethylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.CCNC(=NC(N)=O)C=CC1=CC=CC=C1Cl BOKAQVGFWBVFNR-UHFFFAOYSA-N 0.000 description 2
- IKNWYBUZEHAYGA-UHFFFAOYSA-N [c-[2-(2-chlorophenyl)ethenyl]-n-methylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.NC(=O)N=C(NC)C=CC1=CC=CC=C1Cl IKNWYBUZEHAYGA-UHFFFAOYSA-N 0.000 description 2
- PNGOLITYLMUYOF-UHFFFAOYSA-N [c-[2-(2-chlorophenyl)ethenyl]-n-propan-2-ylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.CC(C)NC(=NC(N)=O)C=CC1=CC=CC=C1Cl PNGOLITYLMUYOF-UHFFFAOYSA-N 0.000 description 2
- VHPRHXFAKNPOMR-UHFFFAOYSA-N [c-[2-(2-chlorophenyl)ethenyl]-n-propylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.CCCNC(=NC(N)=O)C=CC1=CC=CC=C1Cl VHPRHXFAKNPOMR-UHFFFAOYSA-N 0.000 description 2
- MNEHDLKOBQMBPG-UHFFFAOYSA-N [c-[2-(4-chlorophenyl)ethenyl]-n-(4-methylcyclohexyl)carbonimidoyl]urea;hydrochloride Chemical compound Cl.C1CC(C)CCC1NC(=NC(N)=O)C=CC1=CC=C(Cl)C=C1 MNEHDLKOBQMBPG-UHFFFAOYSA-N 0.000 description 2
- PHWQEZSYICGLGF-UHFFFAOYSA-N [c-[2-(4-chlorophenyl)ethenyl]-n-cyclohexylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C=CC(=NC(=O)N)NC1CCCCC1 PHWQEZSYICGLGF-UHFFFAOYSA-N 0.000 description 2
- DVPKQKOQGSNWGW-UHFFFAOYSA-N [c-[2-(4-chlorophenyl)ethenyl]-n-propan-2-ylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.CC(C)NC(=NC(N)=O)C=CC1=CC=C(Cl)C=C1 DVPKQKOQGSNWGW-UHFFFAOYSA-N 0.000 description 2
- SXGXORBQCUGQFM-UHFFFAOYSA-N [c-[2-(4-methoxyphenyl)ethenyl]-n-(4-methylcyclohexyl)carbonimidoyl]urea;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C=CC(=NC(N)=O)NC1CCC(C)CC1 SXGXORBQCUGQFM-UHFFFAOYSA-N 0.000 description 2
- RUWXYHRTNOENDL-UHFFFAOYSA-N [c-[2-(4-methoxyphenyl)ethenyl]-n-propan-2-ylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.COC1=CC=C(C=CC(NC(C)C)=NC(N)=O)C=C1 RUWXYHRTNOENDL-UHFFFAOYSA-N 0.000 description 2
- QNCPDUHPJCPXJZ-UHFFFAOYSA-N [c-[2-(furan-2-yl)ethenyl]-n-(4-methylcyclohexyl)carbonimidoyl]urea;hydrochloride Chemical compound Cl.C1CC(C)CCC1NC(=NC(N)=O)C=CC1=CC=CO1 QNCPDUHPJCPXJZ-UHFFFAOYSA-N 0.000 description 2
- PFIZQTIUTMHYTG-UHFFFAOYSA-N [n-(3-methylcyclohexyl)-c-(2-phenylethenyl)carbonimidoyl]urea;hydrochloride Chemical compound Cl.C1C(C)CCCC1NC(=NC(N)=O)C=CC1=CC=CC=C1 PFIZQTIUTMHYTG-UHFFFAOYSA-N 0.000 description 2
- ZSKQEJADGUZNCX-UHFFFAOYSA-N [n-(4-methylcyclohexyl)-c-(2-phenylethenyl)carbonimidoyl]urea;hydrochloride Chemical compound Cl.C1CC(C)CCC1NC(=NC(N)=O)C=CC1=CC=CC=C1 ZSKQEJADGUZNCX-UHFFFAOYSA-N 0.000 description 2
- IDWYBGUXNNHADX-UHFFFAOYSA-N [n-cyclohexyl-c-(2-phenylethenyl)carbonimidoyl]urea;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C=CC(=NC(=O)N)NC1CCCCC1 IDWYBGUXNNHADX-UHFFFAOYSA-N 0.000 description 2
- OJZPSAGPMFLJFU-UHFFFAOYSA-N [n-cyclohexyl-c-[2-(4-methoxyphenyl)ethenyl]carbonimidoyl]urea;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C=CC(=NC(N)=O)NC1CCCCC1 OJZPSAGPMFLJFU-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940127573 compound 38 Drugs 0.000 description 2
- PTPNMBZOCYSHJF-UHFFFAOYSA-N ethyl 3-(2-chlorophenyl)prop-2-enimidate;hydrochloride Chemical compound Cl.CCOC(=N)C=CC1=CC=CC=C1Cl PTPNMBZOCYSHJF-UHFFFAOYSA-N 0.000 description 2
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- WWIFINLMFRCOJR-UHFFFAOYSA-N n'-cyano-3-(furan-2-yl)-n-(propanoylamino)prop-2-enimidamide Chemical compound CCC(=O)NNC(=NC#N)C=CC1=CC=CO1 WWIFINLMFRCOJR-UHFFFAOYSA-N 0.000 description 2
- UDGVDEKLAOSCTL-UHFFFAOYSA-N n'-cyano-3-(furan-2-yl)prop-2-enimidamide Chemical compound N#CN=C(N)C=CC1=CC=CO1 UDGVDEKLAOSCTL-UHFFFAOYSA-N 0.000 description 2
- VOSVGBRSDACKLO-UHFFFAOYSA-N n'-cyano-3-thiophen-2-ylprop-2-enimidamide Chemical compound N#CN=C(N)C=CC1=CC=CS1 VOSVGBRSDACKLO-UHFFFAOYSA-N 0.000 description 2
- FERKRQBIROZISR-UHFFFAOYSA-N n-cyano-3-(4-methoxyphenyl)-n'-(4-methylcyclohexyl)prop-2-enimidamide Chemical compound C1=CC(OC)=CC=C1C=CC(=NC#N)NC1CCC(C)CC1 FERKRQBIROZISR-UHFFFAOYSA-N 0.000 description 2
- YPBYAHJZMDXRIP-UHFFFAOYSA-N n-cyano-3-(4-methoxyphenyl)-n'-methylprop-2-enimidamide Chemical compound N#CN=C(NC)C=CC1=CC=C(OC)C=C1 YPBYAHJZMDXRIP-UHFFFAOYSA-N 0.000 description 2
- IHWKPIBPROVMHP-UHFFFAOYSA-N n-cyano-3-(4-methoxyphenyl)-n'-propylprop-2-enimidamide Chemical compound CCCNC(=NC#N)C=CC1=CC=C(OC)C=C1 IHWKPIBPROVMHP-UHFFFAOYSA-N 0.000 description 2
- NRUYESUMEPJDMX-UHFFFAOYSA-N n-cyano-3-(furan-2-yl)-n'-(2-phenylethyl)prop-2-enimidamide Chemical compound C=1C=COC=1C=CC(=NC#N)NCCC1=CC=CC=C1 NRUYESUMEPJDMX-UHFFFAOYSA-N 0.000 description 2
- VQWOLFXRPUNFLG-UHFFFAOYSA-N n-cyano-3-(furan-2-yl)-n'-(3-methylcyclohexyl)prop-2-enimidamide Chemical compound C1C(C)CCCC1NC(=NC#N)C=CC1=CC=CO1 VQWOLFXRPUNFLG-UHFFFAOYSA-N 0.000 description 2
- HJRLTIMZFJARTD-UHFFFAOYSA-N n-cyano-3-(furan-2-yl)-n'-propylprop-2-enimidamide Chemical compound CCCNC(=NC#N)C=CC1=CC=CO1 HJRLTIMZFJARTD-UHFFFAOYSA-N 0.000 description 2
- YANKEOVEXDMPFM-UHFFFAOYSA-N n-cyano-3-phenyl-n'-propan-2-ylprop-2-enimidamide Chemical compound CC(C)NC(=NC#N)C=CC1=CC=CC=C1 YANKEOVEXDMPFM-UHFFFAOYSA-N 0.000 description 2
- ONPALTFSJNUGSP-UHFFFAOYSA-N n-cyano-n'-(2-methylpropyl)-3-phenylprop-2-enimidamide Chemical compound CC(C)CNC(=NC#N)C=CC1=CC=CC=C1 ONPALTFSJNUGSP-UHFFFAOYSA-N 0.000 description 2
- UFVIQWOHQVNMOL-UHFFFAOYSA-N n-cyano-n'-(3-methylcyclohexyl)-3-phenylprop-2-enimidamide Chemical compound C1C(C)CCCC1NC(=NC#N)C=CC1=CC=CC=C1 UFVIQWOHQVNMOL-UHFFFAOYSA-N 0.000 description 2
- RWLBFJCVURFUNB-UHFFFAOYSA-N n-cyano-n'-(4-methylcyclohexyl)-3-phenylprop-2-enimidamide Chemical compound C1CC(C)CCC1NC(=NC#N)C=CC1=CC=CC=C1 RWLBFJCVURFUNB-UHFFFAOYSA-N 0.000 description 2
- AQNZTKAEVGAUNQ-UHFFFAOYSA-N n-cyano-n'-cyclohexyl-3-(4-methoxyphenyl)prop-2-enimidamide Chemical compound C1=CC(OC)=CC=C1C=CC(=NC#N)NC1CCCCC1 AQNZTKAEVGAUNQ-UHFFFAOYSA-N 0.000 description 2
- AIUIUMYAQXCKJO-UHFFFAOYSA-N n-cyano-n'-cyclohexyl-3-phenylprop-2-enimidamide Chemical compound C=1C=CC=CC=1C=CC(=NC#N)NC1CCCCC1 AIUIUMYAQXCKJO-UHFFFAOYSA-N 0.000 description 2
- IHBCGVOHRACGCA-UHFFFAOYSA-N n-cyano-n'-ethyl-3-(4-methoxyphenyl)prop-2-enimidamide Chemical compound CCNC(=NC#N)C=CC1=CC=C(OC)C=C1 IHBCGVOHRACGCA-UHFFFAOYSA-N 0.000 description 2
- ZOPMDSQBLMPNNP-UHFFFAOYSA-N n-cyano-n'-ethyl-3-phenylprop-2-enimidamide Chemical compound CCNC(=NC#N)C=CC1=CC=CC=C1 ZOPMDSQBLMPNNP-UHFFFAOYSA-N 0.000 description 2
- UFZKUBLBVWYOFP-UHFFFAOYSA-N n-cyano-n'-methyl-3-thiophen-2-ylprop-2-enimidamide Chemical compound N#CN=C(NC)C=CC1=CC=CS1 UFZKUBLBVWYOFP-UHFFFAOYSA-N 0.000 description 2
- JERPSFQXLFLXJE-UHFFFAOYSA-N n-cyano-n'-propan-2-yl-3-thiophen-2-ylprop-2-enimidamide Chemical compound CC(C)NC(=NC#N)C=CC1=CC=CS1 JERPSFQXLFLXJE-UHFFFAOYSA-N 0.000 description 2
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- CFYSRJGOOUDQOD-UHFFFAOYSA-N (e)-1-aminoprop-2-enylideneurea Chemical compound NC(=O)N=C(N)C=C CFYSRJGOOUDQOD-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
- PWWUUGALKZGDSD-UHFFFAOYSA-N 3-(2-chlorophenyl)prop-2-enenitrile Chemical compound ClC1=CC=CC=C1C=CC#N PWWUUGALKZGDSD-UHFFFAOYSA-N 0.000 description 1
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 229940126639 Compound 33 Drugs 0.000 description 1
- 229940127007 Compound 39 Drugs 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 240000004670 Glycyrrhiza echinata Species 0.000 description 1
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 1
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 1
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
- 238000003482 Pinner synthesis reaction Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- SCGZUYZCNFOPOR-UHFFFAOYSA-N [c-(2-phenylethenyl)-n-propylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.CCCNC(=NC(N)=O)C=CC1=CC=CC=C1 SCGZUYZCNFOPOR-UHFFFAOYSA-N 0.000 description 1
- IQNWCWXENLWZEV-UHFFFAOYSA-N [c-[2-(furan-2-yl)ethenyl]-n-propan-2-ylcarbonimidoyl]urea;hydrochloride Chemical compound Cl.CC(C)NC(=NC(N)=O)C=CC1=CC=CO1 IQNWCWXENLWZEV-UHFFFAOYSA-N 0.000 description 1
- NMBBFEUPPICCPY-UHFFFAOYSA-N [n-butyl-c-(2-phenylethenyl)carbonimidoyl]urea;hydrochloride Chemical compound Cl.CCCCNC(=NC(N)=O)C=CC1=CC=CC=C1 NMBBFEUPPICCPY-UHFFFAOYSA-N 0.000 description 1
- QHQZEPZWKOZPHH-UHFFFAOYSA-N [n-methyl-c-(2-phenylethenyl)carbonimidoyl]urea Chemical compound NC(=O)N=C(NC)C=CC1=CC=CC=C1 QHQZEPZWKOZPHH-UHFFFAOYSA-N 0.000 description 1
- HHRCMOCAEKABJA-UHFFFAOYSA-N [n-methyl-c-(2-phenylethenyl)carbonimidoyl]urea;hydrochloride Chemical compound Cl.NC(=O)N=C(NC)C=CC1=CC=CC=C1 HHRCMOCAEKABJA-UHFFFAOYSA-N 0.000 description 1
- XJZHBBMQTDMUFG-UHFFFAOYSA-N [n-propan-2-yl-c-(2-thiophen-2-ylethenyl)carbonimidoyl]urea Chemical compound CC(C)NC(=NC(N)=O)C=CC1=CC=CS1 XJZHBBMQTDMUFG-UHFFFAOYSA-N 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125961 compound 24 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 229940127271 compound 49 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229940126545 compound 53 Drugs 0.000 description 1
- 229940127113 compound 57 Drugs 0.000 description 1
- 229940125900 compound 59 Drugs 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- KNFVEWZHAMWJFT-UHFFFAOYSA-N ethyl 3-phenylprop-2-enimidate Chemical compound CCOC(=N)C=CC1=CC=CC=C1 KNFVEWZHAMWJFT-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940010454 licorice Drugs 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FPRRQWFQFWTJBM-UHFFFAOYSA-N n'-butyl-n-cyano-3-(furan-2-yl)prop-2-enimidamide Chemical compound CCCCNC(=NC#N)C=CC1=CC=CO1 FPRRQWFQFWTJBM-UHFFFAOYSA-N 0.000 description 1
- QGRCQIKJKREVOH-UHFFFAOYSA-N n'-butyl-n-cyano-3-phenylprop-2-enimidamide Chemical compound CCCCNC(=NC#N)C=CC1=CC=CC=C1 QGRCQIKJKREVOH-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HHSWHTLDDXRLJE-UHFFFAOYSA-N n-cyano-3-(4-methoxyphenyl)-n'-propan-2-ylprop-2-enimidamide Chemical compound COC1=CC=C(C=CC(NC(C)C)=NC#N)C=C1 HHSWHTLDDXRLJE-UHFFFAOYSA-N 0.000 description 1
- LUIYAYNPIOBZFW-UHFFFAOYSA-N n-cyano-3-(furan-2-yl)-n'-(4-methylcyclohexyl)prop-2-enimidamide Chemical compound C1CC(C)CCC1NC(=NC#N)C=CC1=CC=CO1 LUIYAYNPIOBZFW-UHFFFAOYSA-N 0.000 description 1
- MGLBPNQIWCKAJH-UHFFFAOYSA-N n-cyano-3-(furan-2-yl)-n'-propan-2-ylprop-2-enimidamide Chemical compound CC(C)NC(=NC#N)C=CC1=CC=CO1 MGLBPNQIWCKAJH-UHFFFAOYSA-N 0.000 description 1
- VYLHLFVDKDWCBV-UHFFFAOYSA-N n-cyano-3-phenyl-n'-propylprop-2-enimidamide Chemical compound CCCNC(=NC#N)C=CC1=CC=CC=C1 VYLHLFVDKDWCBV-UHFFFAOYSA-N 0.000 description 1
- LOZLNZHDFSXWKY-UHFFFAOYSA-N n-cyano-n'-cyclohexyl-3-(furan-2-yl)prop-2-enimidamide Chemical compound C=1C=COC=1C=CC(=NC#N)NC1CCCCC1 LOZLNZHDFSXWKY-UHFFFAOYSA-N 0.000 description 1
- VRYJWLRDJKFBTH-UHFFFAOYSA-N n-cyano-n'-ethyl-3-(furan-2-yl)prop-2-enimidamide Chemical compound CCNC(=NC#N)C=CC1=CC=CO1 VRYJWLRDJKFBTH-UHFFFAOYSA-N 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/44—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups doubly-bound to carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10906080A JPS5735555A (en) | 1980-08-08 | 1980-08-08 | 3-substituted 2-propenenitrile derivative and its preparation |
| JP15434880A JPS5777662A (en) | 1980-11-01 | 1980-11-01 | 3-substituted 2-propenenitrile derivative and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3122540A1 true DE3122540A1 (de) | 1982-03-25 |
Family
ID=26448850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813122540 Withdrawn DE3122540A1 (de) | 1980-08-08 | 1981-06-05 | In 3-stellung substituierte 2-propenimidamide und verfahren zu deren herstellung |
Country Status (4)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN158869B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1981-03-18 | 1987-02-07 | Ici Plc | |
| DE3267110D1 (de) * | 1981-05-18 | 1985-12-05 | Ici Plc | Amidine derivatives |
| US5272164A (en) * | 1988-12-27 | 1993-12-21 | Kirin Beer Kabushiki Kaisha | Carboximidamide derivatives |
| JPH0662567B2 (ja) * | 1988-12-27 | 1994-08-17 | 麒麟麦酒株式会社 | ピリジンカルボキシイミダミド誘導体、その製造中間体、製造法および用途 |
| US7241776B2 (en) * | 2004-08-02 | 2007-07-10 | Abbott Laboratories | Cyanoamidine P2X7 antagonists for the treatment of pain |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1181693B (de) * | 1963-04-01 | 1964-11-19 | Hoechst Ag | Verfahren zur Herstellung von Harnstoffen |
| JPS5444660A (en) * | 1977-08-29 | 1979-04-09 | Yamanouchi Pharmaceut Co Ltd | Heterocyclic compound and its preparation |
-
1981
- 1981-04-28 GB GB8113046A patent/GB2085871B/en not_active Expired
- 1981-06-04 FR FR8111043A patent/FR2488255A1/fr active Granted
- 1981-06-05 DE DE19813122540 patent/DE3122540A1/de not_active Withdrawn
- 1981-08-04 US US06/289,903 patent/US4407816A/en not_active Expired - Fee Related
Non-Patent Citations (3)
| Title |
|---|
| "Gazz. Chem. Ital" 41 II., S. 98, 1911 |
| "Journal of Organic Chemistry" 26, S. 412 |
| "Shay et al" in Gastroenterology 26, 906 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4407816A (en) | 1983-10-04 |
| FR2488255B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-12-28 |
| GB2085871B (en) | 1984-07-25 |
| GB2085871A (en) | 1982-05-06 |
| FR2488255A1 (fr) | 1982-02-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2734070C2 (de) | Aminoalkylfuranderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE60212759T2 (de) | Alpha-Aminosäure-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Dipeptidylpeptidase-IV Inhibitoren (DPP IV) | |
| DE1964516C3 (de) | 1-Substituierte 3-Propionyl-anilinopyrrolidine, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE69014351T2 (de) | Pyridincarbonsäureamid-Derivate und diese enthaltende pharmazeutische Zusammensetzungen. | |
| DE2065636B2 (de) | Tricyclische Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE2856753A1 (de) | N-substituierte omega -aminoalkanoyl- omega -aminoalkansaeuren, ihre verwendung und verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel | |
| DE69222459T2 (de) | Thiazolidindionderivate, ihre Herstellung und Anwendung | |
| DE2851028A1 (de) | Neue indolo eckige klammer auf 2.3-a eckige klammer zu chinolizidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitung | |
| DE2006978A1 (de) | Neue Aminosäuren, ihre Derivate und ihr Herstellungsverfahren | |
| DE3240727A1 (de) | Ergolinderivate, verfahren zu deren herstellung sowie pharmazeutische zubereitungen, die diese enthalten | |
| DE2455353C3 (de) | Substituierte a -Aminooxvcarbonsäurehydrazidderivate und ihre Säureadditionssalze sowie ihre Verwendung vnd Verfahren zur Herstellung derselben | |
| DE69005861T2 (de) | Benzoxepin-Derivate. | |
| CH372667A (de) | Verfahren zur Herstellung von 3-Aryl-3-pyrrolidinolen | |
| DE2745222A1 (de) | Alkanolaminderivate | |
| DE2720545A1 (de) | Neue chinazolinderivate, ihre herstellung und pharmazeutische mittel | |
| DE2723051C3 (de) | NKAcyO-p-amino-NMn-decyl- und n-tridecyl)-benzamide sowie diese enthaltende Arzneimittel | |
| DE3122540A1 (de) | In 3-stellung substituierte 2-propenimidamide und verfahren zu deren herstellung | |
| DE2705416A1 (de) | Neue derivate des m-trifluormethylphenylpiperidins und deren salze, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen | |
| DD202019A5 (de) | Verfahren zur herstellung von 3,4-disubstituierten 1,2,5-oxadiazol-2-oxiden | |
| EP0345591B1 (de) | Propanolaminderivate | |
| DE1915230B2 (de) | Hydroxyphenylalkylaminderivate, verfahren zu deren herstellung und arzneimittel auf deren basis | |
| DE1770915A1 (de) | Neue Isoindolino-sulfonylharnstoffderivate und Verfahren zu ihrer Herstellung | |
| DE2428200A1 (de) | Essigsaeurederivate, verfahren zu deren herstellung und diese derivate enthaltende arzneimittel | |
| DE2655232A1 (de) | Aethanolaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen | |
| EP0571795A1 (de) | Neue 3-Phenyl-1,2,5-Oxadiazole und ihre Verwendung in der Therapie von cardiovasculären Störungen, insbesondere von Angina-Pectoris und Erektionsstörungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |