DE2519201A1 - Verfahren zur herstellung von 1-(tetrahydro-2-furanyl)-5-fluoruracil - Google Patents
Verfahren zur herstellung von 1-(tetrahydro-2-furanyl)-5-fluoruracilInfo
- Publication number
- DE2519201A1 DE2519201A1 DE19752519201 DE2519201A DE2519201A1 DE 2519201 A1 DE2519201 A1 DE 2519201A1 DE 19752519201 DE19752519201 DE 19752519201 DE 2519201 A DE2519201 A DE 2519201A DE 2519201 A1 DE2519201 A1 DE 2519201A1
- Authority
- DE
- Germany
- Prior art keywords
- fluorouracil
- tetrahydro
- furanyl
- molecular sieves
- process step
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 26
- WFWLQNSHRPWKFK-UHFFFAOYSA-N Tegafur Chemical compound O=C1NC(=O)C(F)=CN1C1OCCC1 WFWLQNSHRPWKFK-UHFFFAOYSA-N 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 229960002949 fluorouracil Drugs 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002808 molecular sieve Substances 0.000 claims description 12
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- ZVAKZVDJIUFFFP-UHFFFAOYSA-N 2-chlorooxolane Chemical compound ClC1CCCO1 ZVAKZVDJIUFFFP-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- JVCXAMPRNBMALM-UHFFFAOYSA-N 5-fluoro-3,6-bis(trimethylsilyl)-1h-pyrimidine-2,4-dione Chemical compound C[Si](C)(C)C=1NC(=O)N([Si](C)(C)C)C(=O)C=1F JVCXAMPRNBMALM-UHFFFAOYSA-N 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 239000003637 basic solution Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000002256 antimetabolite Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- -1 tetrahydro-2-furanyl Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/467,538 US3960864A (en) | 1974-05-06 | 1974-05-06 | Method of synthesizing 1-(tetrahydro-2-furanyl)-5-fluorouracil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2519201A1 true DE2519201A1 (de) | 1975-11-20 |
Family
ID=23856104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752519201 Ceased DE2519201A1 (de) | 1974-05-06 | 1975-04-30 | Verfahren zur herstellung von 1-(tetrahydro-2-furanyl)-5-fluoruracil |
Country Status (14)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653398A1 (de) * | 1975-11-28 | 1977-06-08 | Takeda Chemical Industries Ltd | Verfahren zur herstellung von 5-fluor-uracil-derivaten |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2648239C3 (de) * | 1975-10-24 | 1981-11-12 | Rikagaku Kenkyusho, Wako, Saitama | Di-(trialkylstannyl)-pyrimidinderivate, Verfahren zu ihrer Herstellung und Verfahren zu ihrer Weiterverarbeitung zu nucleosidartigen Pyrimidinderivaten |
| JPS5259174A (en) * | 1975-11-10 | 1977-05-16 | Asahi Chem Ind Co Ltd | Preparation of n-substituted uracil compounds |
| US4324895A (en) * | 1975-12-04 | 1982-04-13 | Rikagaku Kenkyusho | Novel process for producing pyrimidine nucleosides and novel pyrimidine nucleosides obtained thereby |
| DK142415B (da) * | 1975-12-24 | 1980-10-27 | Mitsui Toatsu Chemicals | Fremgangsmåde til fremstilling af 1-(2-tetrahydrofuryl)-5-fluoruracil. |
| 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1168391A (en) * | 1968-01-08 | 1969-10-22 | Inst Organocheskogo Sinteza An | Substituted Uracils |
-
1974
- 1974-05-06 US US05/467,538 patent/US3960864A/en not_active Expired - Lifetime
-
1975
- 1975-04-02 CA CA223,644A patent/CA1024145A/en not_active Expired
- 1975-04-04 ZA ZA00752145A patent/ZA752145B/xx unknown
- 1975-04-07 IL IL47033A patent/IL47033A/xx unknown
- 1975-04-08 NO NO751217A patent/NO141993C/no unknown
- 1975-04-14 GB GB15282/75A patent/GB1503614A/en not_active Expired
- 1975-04-21 AT AT305175A patent/AT337203B/de not_active IP Right Cessation
- 1975-04-30 JP JP50053085A patent/JPS50151884A/ja active Pending
- 1975-04-30 DE DE19752519201 patent/DE2519201A1/de not_active Ceased
- 1975-05-02 CH CH564175A patent/CH610897A5/xx not_active IP Right Cessation
- 1975-05-05 DK DK197175A patent/DK137759C/da active
- 1975-05-05 FR FR7513999A patent/FR2279746A1/fr active Granted
- 1975-05-06 ES ES437481A patent/ES437481A1/es not_active Expired
- 1975-05-06 NL NL7505305A patent/NL7505305A/xx not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653398A1 (de) * | 1975-11-28 | 1977-06-08 | Takeda Chemical Industries Ltd | Verfahren zur herstellung von 5-fluor-uracil-derivaten |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1024145A (en) | 1978-01-10 |
| NL7505305A (nl) | 1975-11-10 |
| NO141993C (no) | 1980-06-11 |
| GB1503614A (en) | 1978-03-15 |
| JPS50151884A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-06 |
| DK197175A (da) | 1975-11-07 |
| AT337203B (de) | 1977-06-27 |
| ATA305175A (de) | 1976-10-15 |
| FR2279746B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-07-06 |
| DK137759B (da) | 1978-05-01 |
| FR2279746A1 (fr) | 1976-02-20 |
| CH610897A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-15 |
| NO141993B (no) | 1980-03-03 |
| ES437481A1 (es) | 1977-07-01 |
| ZA752145B (en) | 1976-03-31 |
| NO751217L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-11-07 |
| AU7993375A (en) | 1976-10-14 |
| IL47033A (en) | 1978-06-15 |
| DK137759C (da) | 1978-10-02 |
| IL47033A0 (en) | 1975-06-25 |
| US3960864A (en) | 1976-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |