JPS6221348B2 - - Google Patents
Info
- Publication number
- JPS6221348B2 JPS6221348B2 JP56006479A JP647981A JPS6221348B2 JP S6221348 B2 JPS6221348 B2 JP S6221348B2 JP 56006479 A JP56006479 A JP 56006479A JP 647981 A JP647981 A JP 647981A JP S6221348 B2 JPS6221348 B2 JP S6221348B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorouracil
- carbamoyl
- reaction solution
- formula
- reaction
- 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
Links
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 229960002949 fluorouracil Drugs 0.000 claims description 16
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 14
- FHLNOFIKNZLHOS-UHFFFAOYSA-N 5-fluoro-2,4-dioxopyrimidine-1-carboxamide Chemical compound NC(=O)N1C=C(F)C(=O)NC1=O FHLNOFIKNZLHOS-UHFFFAOYSA-N 0.000 claims description 13
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- -1 alicyclic hydrocarbon compound Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- AOCCBINRVIKJHY-UHFFFAOYSA-N Carmofur Chemical compound CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O AOCCBINRVIKJHY-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- QSTQPLFBYDUDHN-UHFFFAOYSA-N 1,3-dihexylurea Chemical compound CCCCCCNC(=O)NCCCCCC QSTQPLFBYDUDHN-UHFFFAOYSA-N 0.000 description 1
- SNKDCTFPQUHAPR-UHFFFAOYSA-N 1-fluoropyrimidine-2,4-dione Chemical compound FN1C=CC(=O)NC1=O SNKDCTFPQUHAPR-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- XORCSHBIHQYYJL-UHFFFAOYSA-N 5-fluoro-1-hexylpyrimidine-2,4-dione Chemical compound CCCCCCN1C=C(F)C(=O)NC1=O XORCSHBIHQYYJL-UHFFFAOYSA-N 0.000 description 1
- AVSGWXRHDLBYLK-UHFFFAOYSA-N 5-fluoro-2,4-dioxo-n-propan-2-ylpyrimidine-1-carboxamide Chemical compound CC(C)NC(=O)N1C=C(F)C(=O)NC1=O AVSGWXRHDLBYLK-UHFFFAOYSA-N 0.000 description 1
- PIUCHDXNDBQRTH-UHFFFAOYSA-N 5-fluoro-2,4-dioxo-n-propylpyrimidine-1-carboxamide Chemical compound CCCNC(=O)N1C=C(F)C(=O)NC1=O PIUCHDXNDBQRTH-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 230000021235 carbamoylation Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PVSNDBKXSKXPHM-UHFFFAOYSA-N n-butyl-5-fluoro-2,4-dioxopyrimidine-1-carboxamide Chemical compound CCCCNC(=O)N1C=C(F)C(=O)NC1=O PVSNDBKXSKXPHM-UHFFFAOYSA-N 0.000 description 1
- GDSVEJKZPZSFPE-UHFFFAOYSA-N n-tert-butyl-5-fluoro-2,4-dioxopyrimidine-1-carboxamide Chemical compound CC(C)(C)NC(=O)N1C=C(F)C(=O)NC1=O GDSVEJKZPZSFPE-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56006479A JPS57120578A (en) | 1981-01-21 | 1981-01-21 | Separation of 1-carbamoyl-5-fluorouracils |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56006479A JPS57120578A (en) | 1981-01-21 | 1981-01-21 | Separation of 1-carbamoyl-5-fluorouracils |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57120578A JPS57120578A (en) | 1982-07-27 |
| JPS6221348B2 true JPS6221348B2 (de) | 1987-05-12 |
Family
ID=11639604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56006479A Granted JPS57120578A (en) | 1981-01-21 | 1981-01-21 | Separation of 1-carbamoyl-5-fluorouracils |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57120578A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0310338B2 (de) * | 1987-02-16 | 1991-02-13 | Kaneki Nenryo Jugengaisha |
-
1981
- 1981-01-21 JP JP56006479A patent/JPS57120578A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0310338B2 (de) * | 1987-02-16 | 1991-02-13 | Kaneki Nenryo Jugengaisha |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57120578A (en) | 1982-07-27 |
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