NO771124L - Fremgangsm}te ved fremstilling av uracilderivater - Google Patents
Fremgangsm}te ved fremstilling av uracilderivaterInfo
- Publication number
- NO771124L NO771124L NO771124A NO771124A NO771124L NO 771124 L NO771124 L NO 771124L NO 771124 A NO771124 A NO 771124A NO 771124 A NO771124 A NO 771124A NO 771124 L NO771124 L NO 771124L
- Authority
- NO
- Norway
- Prior art keywords
- fluoro
- hexahydro
- dioxopyrimidine
- carboxylate
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 43
- 238000002360 preparation method Methods 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 109
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 86
- -1 difluoro-6-hydroxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carbonitrile Chemical compound 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
- LKVICQBNKHTHLL-UHFFFAOYSA-N ethyl 5-fluoro-4-hydroxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(O)NC(=O)NC1=O LKVICQBNKHTHLL-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- JUUPPQURHPYPOI-UHFFFAOYSA-N methyl 5-fluoro-4-hydroxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound COC(=O)C1(F)C(O)NC(=O)NC1=O JUUPPQURHPYPOI-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- CMZYDQKKDNXWKW-UHFFFAOYSA-N methyl 5-fluoro-4-methoxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound COC1NC(=O)NC(=O)C1(F)C(=O)OC CMZYDQKKDNXWKW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- TXDAAMARMYNDQO-UHFFFAOYSA-N 5-fluoro-4-hydroxy-2,6-dioxo-1,3-diazinane-5-carbonitrile Chemical compound OC1NC(=O)NC(=O)C1(F)C#N TXDAAMARMYNDQO-UHFFFAOYSA-N 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- MFRHIPNZBVHNHI-UHFFFAOYSA-N ethyl 4-(butylamino)-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCNC1NC(=O)NC(=O)C1(F)C(=O)OCC MFRHIPNZBVHNHI-UHFFFAOYSA-N 0.000 claims description 3
- QYIJQWZDUJULHZ-UHFFFAOYSA-N ethyl 4-butoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCOC1NC(=O)NC(=O)C1(F)C(=O)OCC QYIJQWZDUJULHZ-UHFFFAOYSA-N 0.000 claims description 3
- ZMORFPWKNBKXDK-UHFFFAOYSA-N ethyl 4-ethoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC1NC(=O)NC(=O)C1(F)C(=O)OCC ZMORFPWKNBKXDK-UHFFFAOYSA-N 0.000 claims description 3
- LWJBHTCHFVBTLM-UHFFFAOYSA-N ethyl 5-fluoro-4-octoxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCOC1NC(=O)NC(=O)C1(F)C(=O)OCC LWJBHTCHFVBTLM-UHFFFAOYSA-N 0.000 claims description 3
- UDZQLSVHLCDXBG-UHFFFAOYSA-N methyl 4-acetyloxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound COC(=O)C1(F)C(OC(C)=O)NC(=O)NC1=O UDZQLSVHLCDXBG-UHFFFAOYSA-N 0.000 claims description 3
- MUJVMVJSXYNXOE-UHFFFAOYSA-N methyl 5-fluoro-6-hydroxy-2,4-dioxo-1-(oxolan-2-yl)-1,3-diazinane-5-carboxylate Chemical compound O=C1NC(=O)C(C(=O)OC)(F)C(O)N1C1OCCC1 MUJVMVJSXYNXOE-UHFFFAOYSA-N 0.000 claims description 3
- AJUCOZCPWRGIFR-UHFFFAOYSA-N propan-2-yl 5-fluoro-4-hydroxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CC(C)OC(=O)C1(F)C(O)NC(=O)NC1=O AJUCOZCPWRGIFR-UHFFFAOYSA-N 0.000 claims description 3
- RSNNXYLNQRDWQY-UHFFFAOYSA-N 2-chloroethyl 5-fluoro-4-hydroxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound OC1NC(=O)NC(=O)C1(F)C(=O)OCCCl RSNNXYLNQRDWQY-UHFFFAOYSA-N 0.000 claims description 2
- GKXFZYYVJZKXHK-UHFFFAOYSA-N 4-ethoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxamide Chemical compound CCOC1NC(=O)NC(=O)C1(F)C(N)=O GKXFZYYVJZKXHK-UHFFFAOYSA-N 0.000 claims description 2
- FRKGVMPQSQNPCA-UHFFFAOYSA-N 5-fluoro-4-hydroxy-2,6-dioxo-1,3-diazinane-5-carboxamide Chemical compound NC(=O)C1(F)C(O)NC(=O)NC1=O FRKGVMPQSQNPCA-UHFFFAOYSA-N 0.000 claims description 2
- XABIAHJPIBXQGW-UHFFFAOYSA-N 5-fluoro-6-hydroxy-5-(morpholine-4-carbonyl)-1,3-diazinane-2,4-dione Chemical compound OC1NC(=O)NC(=O)C1(F)C(=O)N1CCOCC1 XABIAHJPIBXQGW-UHFFFAOYSA-N 0.000 claims description 2
- OWCXQWMIPWWOPH-UHFFFAOYSA-N butyl 5-fluoro-4-hydroxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCOC(=O)C1(F)C(O)NC(=O)NC1=O OWCXQWMIPWWOPH-UHFFFAOYSA-N 0.000 claims description 2
- UYIWQSSEOZIULH-UHFFFAOYSA-N ethyl 4-(2,2-dimethylpropoxy)-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(OCC(C)(C)C)NC(=O)NC1=O UYIWQSSEOZIULH-UHFFFAOYSA-N 0.000 claims description 2
- LCIFCESYFWZYHS-UHFFFAOYSA-N ethyl 4-(benzylamino)-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OCC)(F)C1NCC1=CC=CC=C1 LCIFCESYFWZYHS-UHFFFAOYSA-N 0.000 claims description 2
- UHWWOURBQRAETC-UHFFFAOYSA-N ethyl 4-anilino-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OCC)(F)C1NC1=CC=CC=C1 UHWWOURBQRAETC-UHFFFAOYSA-N 0.000 claims description 2
- DAKGVCCXFKOHQB-UHFFFAOYSA-N ethyl 4-butan-2-yloxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(OC(C)CC)NC(=O)NC1=O DAKGVCCXFKOHQB-UHFFFAOYSA-N 0.000 claims description 2
- SIVQWATWCHERSB-UHFFFAOYSA-N ethyl 4-cyclohexylsulfanyl-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OCC)(F)C1SC1CCCCC1 SIVQWATWCHERSB-UHFFFAOYSA-N 0.000 claims description 2
- XLVATWFNLODVDQ-UHFFFAOYSA-N ethyl 4-tert-butylsulfanyl-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(SC(C)(C)C)NC(=O)NC1=O XLVATWFNLODVDQ-UHFFFAOYSA-N 0.000 claims description 2
- KYXOFENPRAATBD-UHFFFAOYSA-N ethyl 5-fluoro-2,4-dioxo-6-phenoxy-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OCC)(F)C1OC1=CC=CC=C1 KYXOFENPRAATBD-UHFFFAOYSA-N 0.000 claims description 2
- YXVLNOQVYQPWGT-UHFFFAOYSA-N ethyl 5-fluoro-2,4-dioxo-6-phenylsulfanyl-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OCC)(F)C1SC1=CC=CC=C1 YXVLNOQVYQPWGT-UHFFFAOYSA-N 0.000 claims description 2
- JXUOHPWXGULPOD-UHFFFAOYSA-N ethyl 5-fluoro-2,4-dioxo-6-piperidin-1-yl-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OCC)(F)C1N1CCCCC1 JXUOHPWXGULPOD-UHFFFAOYSA-N 0.000 claims description 2
- FXTMNPPVWUWLGS-UHFFFAOYSA-N ethyl 5-fluoro-2,4-dioxo-6-prop-2-ynoxy-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(OCC#C)NC(=O)NC1=O FXTMNPPVWUWLGS-UHFFFAOYSA-N 0.000 claims description 2
- WKAHUIZPKIPDJV-UHFFFAOYSA-N ethyl 5-fluoro-4-[(2-methylpropan-2-yl)oxy]-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(OC(C)(C)C)NC(=O)NC1=O WKAHUIZPKIPDJV-UHFFFAOYSA-N 0.000 claims description 2
- PFAYNMDOJHRHFA-UHFFFAOYSA-N ethyl 5-fluoro-4-methoxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(OC)NC(=O)NC1=O PFAYNMDOJHRHFA-UHFFFAOYSA-N 0.000 claims description 2
- OHCKNLHJUAXTID-UHFFFAOYSA-N methyl 4-benzoyloxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OC)(F)C1OC(=O)C1=CC=CC=C1 OHCKNLHJUAXTID-UHFFFAOYSA-N 0.000 claims description 2
- RZIASUFBLIFPTB-UHFFFAOYSA-N methyl 4-butoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCOC1NC(=O)NC(=O)C1(F)C(=O)OC RZIASUFBLIFPTB-UHFFFAOYSA-N 0.000 claims description 2
- STTPGIRVAZQZPE-UHFFFAOYSA-N methyl 4-butylsulfanyl-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCSC1NC(=O)NC(=O)C1(F)C(=O)OC STTPGIRVAZQZPE-UHFFFAOYSA-N 0.000 claims description 2
- LWHNMXJILHLHHJ-UHFFFAOYSA-N methyl 4-ethoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC1NC(=O)NC(=O)C1(F)C(=O)OC LWHNMXJILHLHHJ-UHFFFAOYSA-N 0.000 claims description 2
- IOJAMWBDIXBKQY-UHFFFAOYSA-N methyl 5-fluoro-2,4-dioxo-6-phenylmethoxy-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OC)(F)C1OCC1=CC=CC=C1 IOJAMWBDIXBKQY-UHFFFAOYSA-N 0.000 claims description 2
- ATPVHJAUAKINHW-UHFFFAOYSA-N methyl 5-fluoro-2,4-dioxo-6-phenylsulfanyl-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OC)(F)C1SC1=CC=CC=C1 ATPVHJAUAKINHW-UHFFFAOYSA-N 0.000 claims description 2
- WCXREEXHVQXJKH-UHFFFAOYSA-N methyl 5-fluoro-4-octoxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCOC1NC(=O)NC(=O)C1(F)C(=O)OC WCXREEXHVQXJKH-UHFFFAOYSA-N 0.000 claims description 2
- ZIKMUFBULPEOTD-UHFFFAOYSA-N methyl 6-acetyloxy-5-fluoro-2,4-dioxo-1-(oxolan-2-yl)-1,3-diazinane-5-carboxylate Chemical compound O=C1NC(=O)C(C(=O)OC)(F)C(OC(C)=O)N1C1OCCC1 ZIKMUFBULPEOTD-UHFFFAOYSA-N 0.000 claims description 2
- XDJVPQDRNIXAEX-UHFFFAOYSA-N octadecyl 4-ethoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1(F)C(OCC)NC(=O)NC1=O XDJVPQDRNIXAEX-UHFFFAOYSA-N 0.000 claims description 2
- SLYSXMKRDKOISA-UHFFFAOYSA-N octyl 4-acetyloxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCOC(=O)C1(F)C(OC(C)=O)NC(=O)NC1=O SLYSXMKRDKOISA-UHFFFAOYSA-N 0.000 claims description 2
- VPNPBNCDECUBAK-UHFFFAOYSA-N octyl 5-fluoro-4-hydroxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCOC(=O)C1(F)C(O)NC(=O)NC1=O VPNPBNCDECUBAK-UHFFFAOYSA-N 0.000 claims description 2
- CAJJLUCGAUXMTD-UHFFFAOYSA-N octyl 5-fluoro-4-octoxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCOC1NC(=O)NC(=O)C1(F)C(=O)OCCCCCCCC CAJJLUCGAUXMTD-UHFFFAOYSA-N 0.000 claims description 2
- YLVFGDYYISETNH-UHFFFAOYSA-N propan-2-yl 5-fluoro-2,4-dioxo-6-propan-2-yloxy-1,3-diazinane-5-carboxylate Chemical compound CC(C)OC1NC(=O)NC(=O)C1(F)C(=O)OC(C)C YLVFGDYYISETNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 4
- JIEWFGXFAADPJW-UHFFFAOYSA-N (5-cyano-5-fluoro-2,6-dioxo-1,3-diazinan-4-yl) acetate Chemical compound CC(=O)OC1NC(=O)NC(=O)C1(F)C#N JIEWFGXFAADPJW-UHFFFAOYSA-N 0.000 claims 1
- HTYAAGMCFICFRV-UHFFFAOYSA-N 4,6-dioxo-1H-pyrimidine-5-carboxylic acid Chemical compound O=C1C(C(N=CN1)=O)C(=O)O HTYAAGMCFICFRV-UHFFFAOYSA-N 0.000 claims 1
- IFHZJMXHALLKJR-UHFFFAOYSA-N 4-ethoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carbonitrile Chemical compound CCOC1NC(=O)NC(=O)C1(F)C#N IFHZJMXHALLKJR-UHFFFAOYSA-N 0.000 claims 1
- BXLKWCBPTMCWIN-UHFFFAOYSA-N butyl 4-butoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCOC1NC(=O)NC(=O)C1(F)C(=O)OCCCC BXLKWCBPTMCWIN-UHFFFAOYSA-N 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- LAVPXHZXBLGZOM-UHFFFAOYSA-N ethyl 4-(diethylamino)-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(N(CC)CC)NC(=O)NC1=O LAVPXHZXBLGZOM-UHFFFAOYSA-N 0.000 claims 1
- HPFMOBVEJFCFAP-UHFFFAOYSA-N ethyl 4-acetyloxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(OC(C)=O)NC(=O)NC1=O HPFMOBVEJFCFAP-UHFFFAOYSA-N 0.000 claims 1
- JJKOQXPGWQIXGK-UHFFFAOYSA-N ethyl 4-benzylsulfanyl-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OCC)(F)C1SCC1=CC=CC=C1 JJKOQXPGWQIXGK-UHFFFAOYSA-N 0.000 claims 1
- YZRYUEOPVFCWAZ-UHFFFAOYSA-N ethyl 4-ethylsulfanyl-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(SCC)NC(=O)NC1=O YZRYUEOPVFCWAZ-UHFFFAOYSA-N 0.000 claims 1
- MEWACMSHTGXDBO-UHFFFAOYSA-N ethyl 5-fluoro-2,4-dioxo-6-phenylmethoxy-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OCC)(F)C1OCC1=CC=CC=C1 MEWACMSHTGXDBO-UHFFFAOYSA-N 0.000 claims 1
- OXWAQXFQXQOWAZ-UHFFFAOYSA-N ethyl 5-fluoro-2,4-dioxo-6-propan-2-yloxy-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(OC(C)C)NC(=O)NC1=O OXWAQXFQXQOWAZ-UHFFFAOYSA-N 0.000 claims 1
- QYFIQVSQJNVSEB-UHFFFAOYSA-N ethyl 5-fluoro-4-(2-methylpropoxy)-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCOC(=O)C1(F)C(OCC(C)C)NC(=O)NC1=O QYFIQVSQJNVSEB-UHFFFAOYSA-N 0.000 claims 1
- BGBKBZNBXQWOHZ-UHFFFAOYSA-N methyl 5-fluoro-2,4-dioxo-6-piperidin-1-yl-1,3-diazinane-5-carboxylate Chemical compound N1C(=O)NC(=O)C(C(=O)OC)(F)C1N1CCCCC1 BGBKBZNBXQWOHZ-UHFFFAOYSA-N 0.000 claims 1
- LIESVEXYQBSERF-UHFFFAOYSA-N methyl 5-fluoro-4-hydroxy-1-methyl-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound COC(=O)C1(F)C(O)NC(=O)N(C)C1=O LIESVEXYQBSERF-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 133
- 239000011541 reaction mixture Substances 0.000 description 105
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 94
- 239000000203 mixture Substances 0.000 description 89
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 88
- 239000000243 solution Substances 0.000 description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 238000002844 melting Methods 0.000 description 74
- 230000008018 melting Effects 0.000 description 74
- 239000002904 solvent Substances 0.000 description 72
- 238000000921 elemental analysis Methods 0.000 description 66
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 64
- 239000000741 silica gel Substances 0.000 description 64
- 229910002027 silica gel Inorganic materials 0.000 description 64
- 239000007787 solid Substances 0.000 description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 50
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
- 239000007789 gas Substances 0.000 description 43
- 229910052731 fluorine Inorganic materials 0.000 description 42
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 41
- 239000011737 fluorine Substances 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 38
- 238000010992 reflux Methods 0.000 description 38
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 35
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
- 239000000843 powder Substances 0.000 description 33
- 238000003756 stirring Methods 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000007858 starting material Substances 0.000 description 27
- 238000001816 cooling Methods 0.000 description 26
- 229960001701 chloroform Drugs 0.000 description 25
- 229940098779 methanesulfonic acid Drugs 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000725 suspension Substances 0.000 description 24
- PBQWMVZQUIWTIL-UHFFFAOYSA-N chloroform;hexane;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl.CCCCCC PBQWMVZQUIWTIL-UHFFFAOYSA-N 0.000 description 23
- 238000001914 filtration Methods 0.000 description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
- 238000004440 column chromatography Methods 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000040 effect on leukemia Effects 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- AFBFSJRKJTWIDB-UHFFFAOYSA-N ethyl 4-decylsulfanyl-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCCCSC1NC(=O)NC(=O)C1(F)C(=O)OCC AFBFSJRKJTWIDB-UHFFFAOYSA-N 0.000 description 1
- FBIACOBKZSNFHX-UHFFFAOYSA-N ethyl 5-fluoro-4-octadecylsulfanyl-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCCCCCCCCCCCSC1NC(=O)NC(=O)C1(F)C(=O)OCC FBIACOBKZSNFHX-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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 238000004334 fluoridation Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- XJUJXVATKIRSAM-UHFFFAOYSA-N fluoro(phenyl)methanol Chemical compound OC(F)C1=CC=CC=C1 XJUJXVATKIRSAM-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- CABDFQZZWFMZOD-UHFFFAOYSA-N hydrogen peroxide;hydrochloride Chemical compound Cl.OO CABDFQZZWFMZOD-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- VMUWIFNDNXXSQA-UHFFFAOYSA-N hypofluorite Chemical compound F[O-] VMUWIFNDNXXSQA-UHFFFAOYSA-N 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical class FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- UNBQPLSYQNSBRM-UHFFFAOYSA-N methyl 2,4-bis(trimethylsilyloxy)pyrimidine-5-carboxylate Chemical compound COC(=O)C1=CN=C(O[Si](C)(C)C)N=C1O[Si](C)(C)C UNBQPLSYQNSBRM-UHFFFAOYSA-N 0.000 description 1
- DPOGIRBKYKHNNM-UHFFFAOYSA-N methyl 2,4-dioxo-1,3-bis(oxolan-2-yl)pyrimidine-5-carboxylate Chemical compound O=C1N(C2OCCC2)C(=O)C(C(=O)OC)=CN1C1CCCO1 DPOGIRBKYKHNNM-UHFFFAOYSA-N 0.000 description 1
- DZPVSYRDDPOTGO-UHFFFAOYSA-N methyl 2,4-dioxo-1h-pyrimidine-5-carboxylate;hydrate Chemical compound O.COC(=O)C1=CNC(=O)NC1=O DZPVSYRDDPOTGO-UHFFFAOYSA-N 0.000 description 1
- DQXQVJIEYOFCFQ-UHFFFAOYSA-N methyl 3-methyl-2,4-dioxo-1h-pyrimidine-5-carboxylate Chemical compound COC(=O)C1=CNC(=O)N(C)C1=O DQXQVJIEYOFCFQ-UHFFFAOYSA-N 0.000 description 1
- PQLAKWDZFYKIDX-UHFFFAOYSA-N methyl 5-chloro-4-methoxy-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound COC1NC(=O)NC(=O)C1(Cl)C(=O)OC PQLAKWDZFYKIDX-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- UFZZSDNLEJADAN-UHFFFAOYSA-N octadecyl 2,4-dioxo-1h-pyrimidine-5-carboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CNC(=O)NC1=O UFZZSDNLEJADAN-UHFFFAOYSA-N 0.000 description 1
- XEFSYBJBSHAHPU-UHFFFAOYSA-N octyl 2,4-dioxo-1h-pyrimidine-5-carboxylate Chemical compound CCCCCCCCOC(=O)C1=CNC(=O)NC1=O XEFSYBJBSHAHPU-UHFFFAOYSA-N 0.000 description 1
- JYEWTTRXGBYSRW-UHFFFAOYSA-N octyl 4-acetyloxy-5-fluoro-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCOC(=O)C1(F)CNCNC1OC(C)=O JYEWTTRXGBYSRW-UHFFFAOYSA-N 0.000 description 1
- QLKJYRLGNKZENN-UHFFFAOYSA-N octyl 4-ethoxy-5-fluoro-2,6-dioxo-1,3-diazinane-5-carboxylate Chemical compound CCCCCCCCOC(=O)C1(F)C(OCC)NC(=O)NC1=O QLKJYRLGNKZENN-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 125000000552 p-cresyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1O*)C([H])([H])[H] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- YGSFNCRAZOCNDJ-UHFFFAOYSA-N propan-2-one Chemical compound CC(C)=O.CC(C)=O YGSFNCRAZOCNDJ-UHFFFAOYSA-N 0.000 description 1
- AITJVHNPNLILEG-UHFFFAOYSA-N propan-2-yl 2,4-dioxo-1h-pyrimidine-5-carboxylate Chemical compound CC(C)OC(=O)C1=CNC(=O)NC1=O AITJVHNPNLILEG-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004911 serous fluid Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3665376A JPS52118480A (en) | 1976-03-31 | 1976-03-31 | Synthesis of uracil derivatives |
JP12993276A JPS5353672A (en) | 1976-10-27 | 1976-10-27 | Fluoropyrimidine deivatives |
JP14679576A JPS5371086A (en) | 1976-12-06 | 1976-12-06 | Preparation of uracil derivs. |
Publications (1)
Publication Number | Publication Date |
---|---|
NO771124L true NO771124L (no) | 1977-10-03 |
Family
ID=27289176
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO771124A NO771124L (no) | 1976-03-31 | 1977-03-30 | Fremgangsm}te ved fremstilling av uracilderivater |
Country Status (18)
Country | Link |
---|---|
US (1) | US4329460A (xx) |
CA (1) | CA1081226A (xx) |
CH (1) | CH632748A5 (xx) |
DD (2) | DD137353A5 (xx) |
DE (1) | DE2714392A1 (xx) |
DK (1) | DK142029B (xx) |
ES (1) | ES469098A1 (xx) |
FI (1) | FI770904A (xx) |
FR (1) | FR2346337A1 (xx) |
GB (1) | GB1546346A (xx) |
GR (1) | GR68935B (xx) |
NL (1) | NL7703541A (xx) |
NO (1) | NO771124L (xx) |
PH (1) | PH14553A (xx) |
PL (1) | PL106917B1 (xx) |
PT (1) | PT66374B (xx) |
SE (1) | SE7703721L (xx) |
SU (1) | SU795467A3 (xx) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57179188A (en) * | 1981-04-28 | 1982-11-04 | Shionogi & Co Ltd | 5-fluorouracil derivative |
DK167280B1 (da) * | 1985-03-20 | 1993-10-04 | Ciba Geigy Ag | 3-aryluracilderivater, fremgangsmaade til fremstilling deraf, ukrudtsbekaempelsesmidler indeholdende disse derivater samt anvendelsen af derivaterne til ukrudtsbekaempelse |
US4669081A (en) * | 1986-02-04 | 1987-05-26 | Raytheon Company | LSI fault insertion |
US4816585A (en) * | 1987-03-05 | 1989-03-28 | Olin Corporation | Tetraalkylpiperidinyl substituted uracil derivatives and their use as ultraviolet light stabilizers |
US4904714A (en) * | 1987-10-02 | 1990-02-27 | Olin Corporation | Synthetic resin composition and its method of use |
US4920126A (en) * | 1988-05-10 | 1990-04-24 | Uniroyal Chemical Ltd/Uniroyal Chemical Ltee | Barbituric acid derivative and treatment of leukemia and tumors therewith |
US5312919A (en) * | 1992-06-12 | 1994-05-17 | Baylor Research Institute | Photooxidation products and derivatives thereof of merocyanine-540, their preparation and uses |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3221010A (en) * | 1963-05-02 | 1965-11-30 | Hoffmann La Roche | 5,6-substituted dihydro-5-fluoropyrimidine nucleosides |
US3277092A (en) * | 1963-05-02 | 1966-10-04 | Hoffmann La Roche | 5, 6-substituted dihydro-5-fluoropyrimidines |
US3201387A (en) * | 1963-09-18 | 1965-08-17 | Heidelberger Charles | 5-trifluoromethyluracil, derivatives thereof, and processes for preparing the same |
US3360523A (en) * | 1964-06-17 | 1967-12-26 | Du Pont | 3, 5, 6-substituted hydrouracils |
US3406023A (en) * | 1966-10-31 | 1968-10-15 | Du Pont | Herbicidal method |
US3954758A (en) * | 1970-05-27 | 1976-05-04 | Pcr, Inc. | Process for fluorinating uracil and derivatives thereof |
CH553195A (de) * | 1971-03-19 | 1974-08-30 | Sandoz Ag | Verfahren zur herstellung neuer 2,6-dichlor-benzaldoximo-(s-triazinyl-(6))-aether. |
US3987045A (en) * | 1971-05-03 | 1976-10-19 | Basf Aktiengesellschaft | Disperse dyes based on isoindolene derivatives |
US3954759A (en) * | 1972-07-13 | 1976-05-04 | Pcr, Inc. | Process for preparation of 6-substituted 5-fluorouracil derivatives |
DE2401619C2 (de) * | 1974-01-14 | 1986-04-03 | Kailash Kumar Prof. Dr. 2359 Lentföhrden Gauri | Fungistatisch wirksame Uracilderivate und Verfahren zu ihrer Herstellung |
DE2602175B2 (de) * | 1975-01-22 | 1978-05-03 | Asahi Kasei Kogyo K.K., Osaka (Japan) | 1 -Alkanoyl-5-fluor-uracilderivate und ihre Verwendung |
US4071519A (en) * | 1975-11-05 | 1978-01-31 | Mitsui Toatsu Chemicals, Incorporated | 1-Carbamoyl-5-fluorouracil derivatives |
US4080455A (en) * | 1975-12-16 | 1978-03-21 | Taisho Pharmaceutical Company Limited | 5-Fluoropyrimidin-4-one compositions |
-
1977
- 1977-03-17 GR GR53014A patent/GR68935B/el unknown
- 1977-03-22 FI FI770904A patent/FI770904A/fi not_active Application Discontinuation
- 1977-03-24 CA CA274,676A patent/CA1081226A/en not_active Expired
- 1977-03-24 CH CH373577A patent/CH632748A5/de not_active IP Right Cessation
- 1977-03-25 GB GB12789/77A patent/GB1546346A/en not_active Expired
- 1977-03-29 FR FR7709280A patent/FR2346337A1/fr active Granted
- 1977-03-30 DK DK141177AA patent/DK142029B/da not_active IP Right Cessation
- 1977-03-30 NO NO771124A patent/NO771124L/no unknown
- 1977-03-30 PL PL1977197045A patent/PL106917B1/pl unknown
- 1977-03-30 PT PT66374A patent/PT66374B/pt unknown
- 1977-03-30 SE SE7703721A patent/SE7703721L/xx unknown
- 1977-03-31 SU SU772466666A patent/SU795467A3/ru active
- 1977-03-31 NL NL7703541A patent/NL7703541A/xx not_active Application Discontinuation
- 1977-03-31 PH PH19603A patent/PH14553A/en unknown
- 1977-03-31 DE DE19772714392 patent/DE2714392A1/de not_active Withdrawn
- 1977-03-31 DD DD77206212A patent/DD137353A5/xx unknown
- 1977-03-31 DD DD7700198177A patent/DD132790A5/xx unknown
-
1978
- 1978-04-01 ES ES469098A patent/ES469098A1/es not_active Expired
-
1979
- 1979-06-13 US US06/048,169 patent/US4329460A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
ES469098A1 (es) | 1979-09-16 |
DE2714392A1 (de) | 1977-12-22 |
PT66374B (en) | 1978-08-25 |
SU795467A3 (ru) | 1981-01-07 |
FR2346337B1 (xx) | 1983-05-13 |
CA1081226A (en) | 1980-07-08 |
DK142029C (xx) | 1981-01-05 |
PL106917B1 (pl) | 1980-01-31 |
PL197045A1 (pl) | 1978-02-13 |
DK141177A (xx) | 1977-10-01 |
CH632748A5 (de) | 1982-10-29 |
FR2346337A1 (fr) | 1977-10-28 |
GR68935B (xx) | 1982-03-29 |
SE7703721L (sv) | 1977-10-01 |
PT66374A (en) | 1977-04-01 |
US4329460A (en) | 1982-05-11 |
DD132790A5 (de) | 1978-11-01 |
GB1546346A (en) | 1979-05-23 |
NL7703541A (nl) | 1977-10-04 |
PH14553A (en) | 1981-09-24 |
DK142029B (da) | 1980-08-11 |
FI770904A (xx) | 1977-10-01 |
DD137353A5 (de) | 1979-08-29 |
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