JPS62258376A - ３−ニコチノイル−５−フルオロウラシルおよびその製造方法 - Google Patents
３−ニコチノイル−５−フルオロウラシルおよびその製造方法Info
- Publication number
- JPS62258376A JPS62258376A JP8788686A JP8788686A JPS62258376A JP S62258376 A JPS62258376 A JP S62258376A JP 8788686 A JP8788686 A JP 8788686A JP 8788686 A JP8788686 A JP 8788686A JP S62258376 A JPS62258376 A JP S62258376A
- Authority
- JP
- Japan
- Prior art keywords
- fluorouracil
- reaction
- formula
- nicotinoyl
- reacted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- RBIRALFBSWVTFC-UHFFFAOYSA-N 5-fluoro-3-(pyridine-3-carbonyl)-1H-pyrimidine-2,4-dione Chemical compound C(C1=CN=CC=C1)(=O)N1C(NC=C(C1=O)F)=O RBIRALFBSWVTFC-UHFFFAOYSA-N 0.000 title claims description 8
- 229960002949 fluorouracil Drugs 0.000 claims abstract description 17
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims abstract description 14
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 claims abstract description 8
- YAUASQIAQHIEGR-UHFFFAOYSA-N 5-fluoro-1,3-bis(pyridine-3-carbonyl)pyrimidine-2,4-dione Chemical compound O=C1N(C(=O)C=2C=NC=CC=2)C(=O)C(F)=CN1C(=O)C1=CC=CN=C1 YAUASQIAQHIEGR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- 150000001875 compounds Chemical class 0.000 abstract description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
- 230000000259 anti-tumor effect Effects 0.000 abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 239000007810 chemical reaction solvent Substances 0.000 abstract description 2
- 210000004798 organs belonging to the digestive system Anatomy 0.000 abstract description 2
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- -1 methanol Chemical compound 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 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
- 206010028980 Neoplasm Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001093 anti-cancer Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 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
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OAPBZIITNDJWQW-UHFFFAOYSA-N 3-benzoyl-5-fluoro-1h-pyrimidine-2,4-dione Chemical compound O=C1C(F)=CNC(=O)N1C(=O)C1=CC=CC=C1 OAPBZIITNDJWQW-UHFFFAOYSA-N 0.000 description 1
- AOCCBINRVIKJHY-UHFFFAOYSA-N Carmofur Chemical compound CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O AOCCBINRVIKJHY-UHFFFAOYSA-N 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229960003261 carmofur Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8788686A JPS62258376A (ja) | 1986-04-18 | 1986-04-18 | ３−ニコチノイル−５−フルオロウラシルおよびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8788686A JPS62258376A (ja) | 1986-04-18 | 1986-04-18 | ３−ニコチノイル−５−フルオロウラシルおよびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62258376A true JPS62258376A (ja) | 1987-11-10 |
| JPH032156B2 JPH032156B2 (enrdf_load_stackoverflow) | 1991-01-14 |
Family
ID=13927354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8788686A Granted JPS62258376A (ja) | 1986-04-18 | 1986-04-18 | ３−ニコチノイル−５−フルオロウラシルおよびその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62258376A (enrdf_load_stackoverflow) |
-
1986
- 1986-04-18 JP JP8788686A patent/JPS62258376A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH032156B2 (enrdf_load_stackoverflow) | 1991-01-14 |
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