JPH032156B2 - - Google Patents
Info
- Publication number
- JPH032156B2 JPH032156B2 JP8788686A JP8788686A JPH032156B2 JP H032156 B2 JPH032156 B2 JP H032156B2 JP 8788686 A JP8788686 A JP 8788686A JP 8788686 A JP8788686 A JP 8788686A JP H032156 B2 JPH032156 B2 JP H032156B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorouracil
- reaction
- present
- nicotinoyl
- temperature
- 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
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 13
- 229960002949 fluorouracil Drugs 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 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 claims description 7
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 5
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 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
- 230000000259 anti-tumor effect Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 230000004083 survival effect Effects 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
- 238000006136 alcoholysis reaction Methods 0.000 description 3
- 230000001093 anti-cancer Effects 0.000 description 3
- 230000000694 effects 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
- 238000003756 stirring Methods 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
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 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
- 238000005160 1H NMR spectroscopy Methods 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
- ZINXKWMTURNPGZ-UHFFFAOYSA-N 3-fluoro-1h-pyrimidine-2,4-dione Chemical compound FN1C(=O)C=CNC1=O ZINXKWMTURNPGZ-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
- 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
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002198 insoluble material Substances 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
- -1 nicotinoyl-5-fluorouracil Chemical compound 0.000 description 1
- 210000004798 organs belonging to the digestive system Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification 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
- 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 JPS62258376A (ja) | 1987-11-10 |
JPH032156B2 true JPH032156B2 (US20100223739A1-20100909-C00005.png) | 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 (US20100223739A1-20100909-C00005.png) |
-
1986
- 1986-04-18 JP JP8788686A patent/JPS62258376A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS62258376A (ja) | 1987-11-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1080086A1 (de) | Dihydropyrimidine | |
JPS63275582A (ja) | 2−アミノイミダゾ〔4,5−b〕ピリジン誘導体の製造方法 | |
JPH05194359A (ja) | 新規尿素誘導体、その製法と治療用途 | |
JP7205059B2 (ja) | エボジアミンの製造方法 | |
EP1791841A1 (en) | 2-substituted-1-deaza purine derivatives with adenosine receptor modulating activity | |
JPH032156B2 (US20100223739A1-20100909-C00005.png) | ||
CN111233750B (zh) | 一种3,3-二氟-1,2,3,6-四氢哌啶类衍生物及其制备方法 | |
JPH0641135A (ja) | イミダゾプテリジン誘導体及びその製造方法 | |
KR20100110319A (ko) | 2-(1차/2차 아미노)히드로카르빌)-카르바모일-7-옥소-2,6-디아자-바이시클로[3.2.0.]헵탄-6-술폰산 유도체의 제조 방법 | |
JPS6272662A (ja) | 4−アルコキシ−3−ピロリン−2−オン−1−イル−酢酸アルキルエステルおよびその製造方法 | |
JP3018185B1 (ja) | キナゾリン誘導体又はその塩の製造方法 | |
JPH061776A (ja) | 置換ピラジンカルボニトリルの製造方法 | |
JP2719841B2 (ja) | チオ尿素誘導体及びその製造方法 | |
JPS6024102B2 (ja) | 5−フルオロウラシル誘導体の製法 | |
CN115850240B (zh) | 一种治疗急性髓系白血病药物奥卢他西尼的合成方法 | |
JPH0558985A (ja) | シアノグアニジン誘導体の製造法 | |
CN111925336B (zh) | 一种含1,2,4-巯基三氮唑的衍生物及其制备方法和应用 | |
JP3161999B2 (ja) | 2,4−ジオキソ−3−アザビシクロ[3.1.0]ヘキサンの製法 | |
JPS5946511B2 (ja) | 1−(n−ヒドロキシアルキルカルバモイル)−5−フルオロウラシル類およびその製造法 | |
JPS6310958B2 (US20100223739A1-20100909-C00005.png) | ||
JPH051053A (ja) | 6−(3−ジメチルアミノプロピオニル)フオルスコリンの新規製造法 | |
JPS6144868A (ja) | 新規なフレデリカマイシンa誘導体 | |
JPS607624B2 (ja) | 1―(n―アラルキルカルバモイル)―5―フルオロウラシル類およびその製造法 | |
US6333414B1 (en) | Process for the synthesis of trisubstituted oxazoles | |
JPS5843969A (ja) | ベンゾチアジンカルボキサミド類の製造方法 |