DE2357847A1 - Verfahren zur herstellung von n tief 1-(2'-furanidyl)- und n tief 1(2'-pyranidyl)-urazilen - Google Patents
Verfahren zur herstellung von n tief 1-(2'-furanidyl)- und n tief 1(2'-pyranidyl)-urazilenInfo
- Publication number
- DE2357847A1 DE2357847A1 DE2357847A DE2357847A DE2357847A1 DE 2357847 A1 DE2357847 A1 DE 2357847A1 DE 2357847 A DE2357847 A DE 2357847A DE 2357847 A DE2357847 A DE 2357847A DE 2357847 A1 DE2357847 A1 DE 2357847A1
- Authority
- DE
- Germany
- Prior art keywords
- furanidyl
- trimethylsilyl
- bis
- general formula
- mol
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 9
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000004292 cyclic ethers Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000004122 cyclic group Chemical class 0.000 claims 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XTDKZSUYCXHXJM-UHFFFAOYSA-N 2-methoxyoxane Chemical compound COC1CCCCO1 XTDKZSUYCXHXJM-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 210000005075 mammary gland Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- -1 pyranidyl Chemical group 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
- 229960001674 tegafur Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1848519 | 1972-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2357847A1 true DE2357847A1 (de) | 1974-06-20 |
Family
ID=20532678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2357847A Pending DE2357847A1 (de) | 1972-11-20 | 1973-11-20 | Verfahren zur herstellung von n tief 1-(2'-furanidyl)- und n tief 1(2'-pyranidyl)-urazilen |
Country Status (9)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2650918A1 (de) * | 1975-11-10 | 1977-05-26 | Asahi Chemical Ind | Verfahren zur herstellung von n tief 1-(2'-furanidyl)-5-fluor-uracil |
| DE2653398A1 (de) * | 1975-11-28 | 1977-06-08 | Takeda Chemical Industries Ltd | Verfahren zur herstellung von 5-fluor-uracil-derivaten |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5175079A (en) * | 1974-09-13 | 1976-06-29 | Mitsui Seiyaku Kogyo Kk | 11 * 22 tetorahidorofuriru * 55 furuororashiru no seizoho |
| US4039546A (en) * | 1975-04-28 | 1977-08-02 | Solomon Aronovich Giller | Method of preparing N1 -(2'-furanidyl)-5-substituted uracils |
| US4124765A (en) * | 1975-05-13 | 1978-11-07 | Ono Pharmaceutical Co., Ltd. | 5-Fluorouracil derivatives |
| 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 |
| IL50671A (en) * | 1976-10-12 | 1980-03-31 | Abic Ltd | Process for the preparation of n1-(2'furanidyl)-5-fluoro-uracil and bis-2'-furanidylether as intermediate therefor |
| US4125719A (en) * | 1977-08-01 | 1978-11-14 | Merck & Co., Inc. | 1,3,5-S-Hexahydrotrisubstituted triazines |
| EP0059307A1 (de) | 1981-02-26 | 1982-09-08 | Grünenthal GmbH | Verfahren zur Herstellung von 2-Oxabicyclo(3.3.0)octanderivaten und danach erhältliche Produkte |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352849A (en) * | 1965-10-24 | 1967-11-14 | Merck & Co Inc | 6-aza-2'-deoxyuridines |
-
1973
- 1973-06-01 US US366215A patent/US3912734A/en not_active Expired - Lifetime
- 1973-11-14 CA CA185,741A patent/CA999863A/en not_active Expired
- 1973-11-16 GB GB5320873A patent/GB1438987A/en not_active Expired
- 1973-11-16 CH CH1614673A patent/CH586696A5/xx not_active IP Right Cessation
- 1973-11-16 NL NL7315712A patent/NL7315712A/xx unknown
- 1973-11-19 SE SE7315630A patent/SE412232B/xx unknown
- 1973-11-20 DE DE2357847A patent/DE2357847A1/de active Pending
- 1973-11-20 FR FR7341199A patent/FR2207138B1/fr not_active Expired
- 1973-11-20 BE BE137955A patent/BE807556A/xx not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2650918A1 (de) * | 1975-11-10 | 1977-05-26 | Asahi Chemical Ind | Verfahren zur herstellung von n tief 1-(2'-furanidyl)-5-fluor-uracil |
| DE2650918C2 (de) * | 1975-11-10 | 1983-06-09 | Asahi Kasei Kogyo K.K., Osaka | Verfahren zur Herstellung von N↓1↓-(2-Tetrahydrofuranyl)-5-fluor-uracil |
| 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 |
|---|---|
| US3912734A (en) | 1975-10-14 |
| NL7315712A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-22 |
| CA999863A (en) | 1976-11-16 |
| BE807556A (fr) | 1974-05-20 |
| FR2207138B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-01 |
| FR2207138A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-14 |
| GB1438987A (en) | 1976-06-09 |
| CH586696A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-15 |
| SE412232B (sv) | 1980-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |