JPH0441145B2 - - Google Patents
Info
- Publication number
- JPH0441145B2 JPH0441145B2 JP59268199A JP26819984A JPH0441145B2 JP H0441145 B2 JPH0441145 B2 JP H0441145B2 JP 59268199 A JP59268199 A JP 59268199A JP 26819984 A JP26819984 A JP 26819984A JP H0441145 B2 JPH0441145 B2 JP H0441145B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- tetrahydro
- hydroxy
- thioxo
- oxo
- 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.)
- Expired - Lifetime
Links
- -1 2-methoxy-5-methylphenyl group Chemical group 0.000 claims description 42
- 238000004519 manufacturing process Methods 0.000 claims description 41
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 208000032839 leukemia Diseases 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 10
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- XQJCZYJJUILVCC-UHFFFAOYSA-N N-oxo-2-sulfanylidene-1H-pyrimidine-5-carboxamide Chemical compound O=NC(=O)C=1C=NC(NC1)=S XQJCZYJJUILVCC-UHFFFAOYSA-N 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 5
- 239000002612 dispersion medium Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 4
- GFYRZTLCYQQVHZ-UHFFFAOYSA-N 6-hydroxy-4-oxo-n-phenyl-2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical compound N1C(=S)NC(=O)C(C(=O)NC=2C=CC=CC=2)=C1O GFYRZTLCYQQVHZ-UHFFFAOYSA-N 0.000 claims 4
- NAOIGSHYLMLVFK-UHFFFAOYSA-N 6-hydroxy-n-(2-methoxy-5-methylphenyl)-4-oxo-2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical compound COC1=CC=C(C)C=C1NC(=O)C1=C(O)NC(=S)NC1=O NAOIGSHYLMLVFK-UHFFFAOYSA-N 0.000 claims 4
- OXKVARFOQDAIKQ-UHFFFAOYSA-N 6-hydroxy-n-(2-methylphenyl)-4-oxo-2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=C(O)NC(=S)NC1=O OXKVARFOQDAIKQ-UHFFFAOYSA-N 0.000 claims 3
- PMSGAOJRVIHPCQ-UHFFFAOYSA-N 6-hydroxy-n-(4-methoxyphenyl)-4-oxo-2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=C(O)NC(=S)NC1=O PMSGAOJRVIHPCQ-UHFFFAOYSA-N 0.000 claims 3
- ORXNJGMITSNRKH-UHFFFAOYSA-N 2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical compound NC(=O)C=1C=NC(=S)NC=1 ORXNJGMITSNRKH-UHFFFAOYSA-N 0.000 claims 2
- UZRISXBJOMPOTH-UHFFFAOYSA-N n-(2,4-difluorophenyl)-6-hydroxy-4-oxo-2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical compound N1C(=S)NC(=O)C(C(=O)NC=2C(=CC(F)=CC=2)F)=C1O UZRISXBJOMPOTH-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 64
- 150000001875 compounds Chemical class 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 238000012360 testing method Methods 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 28
- 239000000047 product Substances 0.000 description 25
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 239000000843 powder Substances 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 14
- 230000000694 effects Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 230000002354 daily effect Effects 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- LIEDRBQDSZEAQR-UHFFFAOYSA-N n-sulfanylidenepyrimidine-5-carboxamide Chemical compound S=NC(=O)C1=CN=CN=C1 LIEDRBQDSZEAQR-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 229910052717 sulfur Chemical group 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- 230000004614 tumor growth Effects 0.000 description 4
- DLMPJSWFKZILOI-UHFFFAOYSA-N 1-methyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CN1C(=O)CC(=O)NC1=S DLMPJSWFKZILOI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 125000000837 carbohydrate group Chemical group 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical class NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 229910052711 selenium Chemical group 0.000 description 3
- 239000011669 selenium Chemical group 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- RLDQPRHGNKPAKS-UHFFFAOYSA-N O=C1CC(=O)NC(=[Se])N1 Chemical compound O=C1CC(=O)NC(=[Se])N1 RLDQPRHGNKPAKS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000003070 absorption delaying agent Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 201000008275 breast carcinoma Diseases 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000003843 furanosyl group Chemical group 0.000 description 2
- 239000007951 isotonicity adjuster Substances 0.000 description 2
- 208000003747 lymphoid leukemia Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000003132 pyranosyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- IYKVLICPFCEZOF-UHFFFAOYSA-N selenourea Chemical compound NC(N)=[Se] IYKVLICPFCEZOF-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- NWWZLDXOHWTTKD-UHFFFAOYSA-N 1,3-dimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CN1C(=O)CC(=O)N(C)C1=S NWWZLDXOHWTTKD-UHFFFAOYSA-N 0.000 description 1
- ZFIMUSUHAOSEIE-UHFFFAOYSA-N 1,3-diphenyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound O=C1CC(=O)N(C=2C=CC=CC=2)C(=S)N1C1=CC=CC=C1 ZFIMUSUHAOSEIE-UHFFFAOYSA-N 0.000 description 1
- LJJRXPXDTAUVQU-UHFFFAOYSA-N 1-butyl-4-isocyanatobenzene Chemical compound CCCCC1=CC=C(N=C=O)C=C1 LJJRXPXDTAUVQU-UHFFFAOYSA-N 0.000 description 1
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- FMYVTFRADSNGDN-UHFFFAOYSA-N 1-ethoxy-4-isocyanatobenzene Chemical compound CCOC1=CC=C(N=C=O)C=C1 FMYVTFRADSNGDN-UHFFFAOYSA-N 0.000 description 1
- RIKWVZGZRYDACA-UHFFFAOYSA-N 1-fluoro-3-isocyanatobenzene Chemical compound FC1=CC=CC(N=C=O)=C1 RIKWVZGZRYDACA-UHFFFAOYSA-N 0.000 description 1
- DSVGFKBFFICWLZ-UHFFFAOYSA-N 1-fluoro-4-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C=C1 DSVGFKBFFICWLZ-UHFFFAOYSA-N 0.000 description 1
- SUVCZZADQDCIEQ-UHFFFAOYSA-N 1-isocyanato-2-methoxybenzene Chemical compound COC1=CC=CC=C1N=C=O SUVCZZADQDCIEQ-UHFFFAOYSA-N 0.000 description 1
- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 1
- BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- NPXACSUWYDROMZ-UHFFFAOYSA-N 1-phenyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound S=C1NC(=O)CC(=O)N1C1=CC=CC=C1 NPXACSUWYDROMZ-UHFFFAOYSA-N 0.000 description 1
- HNMQOBQNWWMABB-UHFFFAOYSA-N 2,4,6-trioxo-n-phenyl-1,3-diazinane-5-carboxamide Chemical compound O=C1NC(=O)NC(=O)C1C(=O)NC1=CC=CC=C1 HNMQOBQNWWMABB-UHFFFAOYSA-N 0.000 description 1
- HNENEALJPWJWJY-UHFFFAOYSA-N 2,4-difluoro-1-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C(F)=C1 HNENEALJPWJWJY-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical group NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- PQFOUIMVTGBFRN-UHFFFAOYSA-N 2-isocyanato-1-methyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N=C=O PQFOUIMVTGBFRN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 description 1
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 1
- PIRGOOJPOCMVOK-UHFFFAOYSA-N 4-hydroxy-1,3-dimethyl-6-oxo-N-phenyl-2-sulfanylidenepyrimidine-5-carboxamide Chemical compound OC1=C(C(N(C(N1C)=S)C)=O)C(=O)NC1=CC=CC=C1 PIRGOOJPOCMVOK-UHFFFAOYSA-N 0.000 description 1
- MJJXWPHZDBIHIM-UHFFFAOYSA-N 5-isocyanato-1,2,3-trimethoxybenzene Chemical compound COC1=CC(N=C=O)=CC(OC)=C1OC MJJXWPHZDBIHIM-UHFFFAOYSA-N 0.000 description 1
- STUQITWXBMZUGY-UHFFFAOYSA-N 6-hydroxy-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound OC1=CC(O)=NC(S)=N1 STUQITWXBMZUGY-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 208000001382 Experimental Melanoma Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000006552 Lewis Lung Carcinoma Diseases 0.000 description 1
- 206010025538 Malignant ascites Diseases 0.000 description 1
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- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- UQFFIFUYIQXSPD-UHFFFAOYSA-N diethyl 2-(phenylcarbamoyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)NC1=CC=CC=C1 UQFFIFUYIQXSPD-UHFFFAOYSA-N 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
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- 239000007928 intraperitoneal injection Substances 0.000 description 1
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- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
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- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
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- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
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- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
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- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56269383A | 1983-12-19 | 1983-12-19 | |
| US562693 | 1983-12-19 | ||
| US665201 | 1984-10-26 | ||
| US665267 | 1984-10-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60166669A JPS60166669A (ja) | 1985-08-29 |
| JPH0441145B2 true JPH0441145B2 (fi) | 1992-07-07 |
Family
ID=24247362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26819984A Granted JPS60166669A (ja) | 1983-12-19 | 1984-12-19 | ５−ピリミジンカルボキサミドおよびチオカルボキサミド、ならびにこれらによる白血病および腫瘍の治療法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS60166669A (fi) |
| GB (1) | GB8431832D0 (fi) |
| ZA (1) | ZA849819B (fi) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL73840A (en) * | 1983-12-19 | 1988-11-15 | Uniroyal Chem Co Inc | 2-thio-5-(thio)carbamoyl barbituric acid derivatives,their preparation and pharmaceutical compositions containing them |
| TWI772309B (zh) | 2016-06-30 | 2022-08-01 | 美商艾克奎斯特有限責任公司 | 化合物及其於降低尿酸位準之用途(二) |
| TWI749024B (zh) | 2016-07-06 | 2021-12-11 | 美商艾克奎斯特有限責任公司 | 化合物及其於降低尿酸位準之用途 |
| IT201700028709A1 (it) | 2017-03-15 | 2018-09-15 | Fondazione St Italiano Tecnologia | Acidi-5-carbossamide-2-tiobarbiturici e loro uso come medicamenti |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50107141A (fi) * | 1974-02-07 | 1975-08-23 | ||
| JPS5538396A (en) * | 1978-09-12 | 1980-03-17 | Ciba Geigy Ag | Method of protecting keratin material from keratin eating insect and novel 55phenylcarbamoyllbarbituric acid compond |
-
1984
- 1984-12-17 GB GB848431832A patent/GB8431832D0/en active Pending
- 1984-12-17 ZA ZA849819A patent/ZA849819B/xx unknown
- 1984-12-19 JP JP26819984A patent/JPS60166669A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50107141A (fi) * | 1974-02-07 | 1975-08-23 | ||
| JPS50112381A (fi) * | 1974-02-07 | 1975-09-03 | ||
| JPS5538396A (en) * | 1978-09-12 | 1980-03-17 | Ciba Geigy Ag | Method of protecting keratin material from keratin eating insect and novel 55phenylcarbamoyllbarbituric acid compond |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA849819B (en) | 1985-07-31 |
| GB8431832D0 (en) | 1985-01-30 |
| JPS60166669A (ja) | 1985-08-29 |
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