CH616936A5 - - Google Patents
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- Publication number
- CH616936A5 CH616936A5 CH1402276A CH1402276A CH616936A5 CH 616936 A5 CH616936 A5 CH 616936A5 CH 1402276 A CH1402276 A CH 1402276A CH 1402276 A CH1402276 A CH 1402276A CH 616936 A5 CH616936 A5 CH 616936A5
- Authority
- CH
- Switzerland
- Prior art keywords
- uracil
- fluoro
- bis
- furyl
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 22
- 229960002949 fluorouracil Drugs 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- 238000003797 solvolysis reaction Methods 0.000 claims description 11
- FLMBDTNCANYTCP-UHFFFAOYSA-N 5-fluoro-1,3-bis(oxolan-2-yl)pyrimidine-2,4-dione Chemical compound O=C1N(C2OCCC2)C(=O)C(F)=CN1C1CCCO1 FLMBDTNCANYTCP-UHFFFAOYSA-N 0.000 claims description 8
- WFWLQNSHRPWKFK-UHFFFAOYSA-N Tegafur Chemical compound O=C1NC(=O)C(F)=CN1C1OCCC1 WFWLQNSHRPWKFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 3
- TYWVHIPSNSXVJG-UHFFFAOYSA-N 5-fluoro-6-(oxolan-2-yl)-1h-pyrimidine-2,4-dione Chemical compound N1C(=O)NC(=O)C(F)=C1C1OCCC1 TYWVHIPSNSXVJG-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- ZVAKZVDJIUFFFP-UHFFFAOYSA-N 2-chlorooxolane Chemical compound ClC1CCCO1 ZVAKZVDJIUFFFP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14271775A JPS5268188A (en) | 1975-11-28 | 1975-11-28 | Preparation of 1-(tetrahydro-2-furyl)-5-fluorouracil |
| JP526076A JPS5289679A (en) | 1976-01-19 | 1976-01-19 | Preparation of 5-fluorouracil derivatives |
| JP8386376A JPS539778A (en) | 1976-07-13 | 1976-07-13 | Preparation of 5-fluorouracil derivativds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616936A5 true CH616936A5 (en, 2012) | 1980-04-30 |
Family
ID=27276677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1402276A CH616936A5 (en, 2012) | 1975-11-28 | 1976-11-08 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4249006A (en, 2012) |
| AT (1) | AT346858B (en, 2012) |
| AU (1) | AU501833B2 (en, 2012) |
| BE (1) | BE848662A (en, 2012) |
| CA (1) | CA1122983A (en, 2012) |
| CH (1) | CH616936A5 (en, 2012) |
| DE (1) | DE2653398C2 (en, 2012) |
| DK (1) | DK140635B (en, 2012) |
| FR (1) | FR2332991A1 (en, 2012) |
| GB (1) | GB1570219A (en, 2012) |
| GR (1) | GR62855B (en, 2012) |
| HK (1) | HK11283A (en, 2012) |
| HU (1) | HU176890B (en, 2012) |
| IE (1) | IE45046B1 (en, 2012) |
| MX (1) | MX3873E (en, 2012) |
| MY (1) | MY8400088A (en, 2012) |
| NL (1) | NL7613285A (en, 2012) |
| NO (1) | NO144887C (en, 2012) |
| PH (1) | PH12998A (en, 2012) |
| PL (1) | PL104613B1 (en, 2012) |
| PT (1) | PT65883B (en, 2012) |
| SE (1) | SE423389B (en, 2012) |
| SG (1) | SG783G (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004103382A1 (en) * | 2003-05-20 | 2004-12-02 | Aronex Pharmaceuticals, Inc. | Combination chemotherapy comprising 5-fluorouracil or a derivative thereof and a liposomal platinum complex |
| CN103159746B (zh) * | 2011-12-12 | 2015-09-02 | 山东新时代药业有限公司 | 一种工业法合成替加氟的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695297C3 (de) * | 1968-01-10 | 1978-12-07 | Institut Organitscheskogo Sinteza, Riga (Sowjetunion) | 5-Fluor-l-(2-tetrahydrofuryl)-uracil und dessen Alkal'imetaUsalze, Verfahren zu deren Herstellung und diese enthaltende Mittel |
| US3912734A (en) * | 1972-11-20 | 1975-10-14 | Solomon Aronovich Giller | Method for preparing N{HD 1{B -(2{40 -furanidyl)-and N{HD 1{B -2(2{40 -pyranidyl) uracils |
| US3960864A (en) * | 1974-05-06 | 1976-06-01 | The University Of Utah | Method of synthesizing 1-(tetrahydro-2-furanyl)-5-fluorouracil |
| DE2519079A1 (de) * | 1975-04-29 | 1976-11-11 | Inst Orch Sintesa Akademii Nau | Verfahren zur herstellung von n tief 1-(2'-furanicyl)-5-substituierten uracilen |
| JPS5259174A (en) * | 1975-11-10 | 1977-05-16 | Asahi Chem Ind Co Ltd | Preparation of n-substituted uracil compounds |
-
1976
- 1976-11-04 IE IE2461/76A patent/IE45046B1/en unknown
- 1976-11-05 GR GR52112A patent/GR62855B/el unknown
- 1976-11-05 CA CA265,062A patent/CA1122983A/en not_active Expired
- 1976-11-08 CH CH1402276A patent/CH616936A5/fr not_active IP Right Cessation
- 1976-11-12 GB GB47197/76A patent/GB1570219A/en not_active Expired
- 1976-11-15 FR FR7634249A patent/FR2332991A1/fr active Granted
- 1976-11-15 AU AU19655/76A patent/AU501833B2/en not_active Expired
- 1976-11-23 BE BE6045773A patent/BE848662A/xx not_active IP Right Cessation
- 1976-11-24 US US05/744,929 patent/US4249006A/en not_active Expired - Lifetime
- 1976-11-24 PT PT65883A patent/PT65883B/pt unknown
- 1976-11-24 PL PL1976193890A patent/PL104613B1/pl unknown
- 1976-11-24 DK DK528576AA patent/DK140635B/da not_active IP Right Cessation
- 1976-11-24 MX MX765150U patent/MX3873E/es unknown
- 1976-11-24 DE DE2653398A patent/DE2653398C2/de not_active Expired
- 1976-11-25 AT AT874876A patent/AT346858B/de not_active IP Right Cessation
- 1976-11-26 HU HU76TA1418A patent/HU176890B/hu unknown
- 1976-11-26 SE SE7613305A patent/SE423389B/xx not_active IP Right Cessation
- 1976-11-26 NO NO764048A patent/NO144887C/no unknown
- 1976-11-26 PH PH19171A patent/PH12998A/en unknown
- 1976-11-29 NL NL7613285A patent/NL7613285A/xx not_active Application Discontinuation
-
1983
- 1983-01-10 SG SG7/83A patent/SG783G/en unknown
- 1983-03-24 HK HK112/83A patent/HK11283A/xx unknown
-
1984
- 1984-12-30 MY MY88/84A patent/MY8400088A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE423389B (sv) | 1982-05-03 |
| HU176890B (en) | 1981-05-28 |
| PT65883A (en) | 1976-12-01 |
| FR2332991A1 (fr) | 1977-06-24 |
| PL104613B1 (pl) | 1979-08-31 |
| NO144887C (no) | 1981-12-02 |
| SG783G (en) | 1983-09-09 |
| NO144887B (no) | 1981-08-24 |
| DE2653398A1 (de) | 1977-06-08 |
| SE7613305L (sv) | 1977-05-29 |
| DE2653398C2 (de) | 1986-07-17 |
| DK140635B (da) | 1979-10-15 |
| BE848662A (fr) | 1977-05-23 |
| AT346858B (de) | 1978-11-27 |
| GR62855B (en) | 1979-06-23 |
| IE45046B1 (en) | 1982-06-16 |
| PH12998A (en) | 1979-10-29 |
| HK11283A (en) | 1983-03-24 |
| IE45046L (en) | 1977-05-28 |
| CA1122983A (en) | 1982-05-04 |
| DK528576A (en, 2012) | 1977-05-29 |
| ATA874876A (de) | 1978-04-15 |
| MX3873E (es) | 1981-08-26 |
| NL7613285A (nl) | 1977-06-01 |
| MY8400088A (en) | 1984-12-31 |
| DK140635C (en, 2012) | 1980-03-10 |
| AU1965576A (en) | 1978-05-25 |
| AU501833B2 (en) | 1979-06-28 |
| GB1570219A (en) | 1980-06-25 |
| FR2332991B1 (en, 2012) | 1980-03-21 |
| PT65883B (en) | 1978-10-12 |
| US4249006A (en) | 1981-02-03 |
| NO764048L (en, 2012) | 1977-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |