FI63570C - Foerfarande foer framstaellning av n'-(2'-furanidyl)-5-fluor-uracil d v s ftorafur - Google Patents
Foerfarande foer framstaellning av n'-(2'-furanidyl)-5-fluor-uracil d v s ftorafur Download PDFInfo
- Publication number
- FI63570C FI63570C FI772933A FI772933A FI63570C FI 63570 C FI63570 C FI 63570C FI 772933 A FI772933 A FI 772933A FI 772933 A FI772933 A FI 772933A FI 63570 C FI63570 C FI 63570C
- Authority
- FI
- Finland
- Prior art keywords
- process according
- fluorouracil
- dihydrofuran
- ftorafur
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 229960002949 fluorouracil Drugs 0.000 title claims description 19
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 title claims description 13
- 229960001674 tegafur Drugs 0.000 title claims description 13
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 13
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 239000007858 starting material Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000007517 lewis acids Chemical group 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- -1 for example Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- ZUEYOPWNPPBVET-UHFFFAOYSA-N 3-(2H-furan-2-id-3-yloxy)-2H-furan-2-ide Chemical compound C1=CO[C-]=C1OC=1C=CO[C-]=1 ZUEYOPWNPPBVET-UHFFFAOYSA-N 0.000 description 1
- YGUWRMHFQQAUMB-UHFFFAOYSA-N 5-fluoro-3-(2H-furan-2-id-3-yl)-1H-pyrimidine-2,4-dione Chemical compound O=C1C(F)=CNC(=O)N1C1=[C-]OC=C1 YGUWRMHFQQAUMB-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution 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
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical class ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- 108700021180 rat Mnt Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL5067176 | 1976-10-12 | ||
| IL50671A IL50671A (en) | 1976-10-12 | 1976-10-12 | Process for the preparation of n1-(2'furanidyl)-5-fluoro-uracil and bis-2'-furanidylether as intermediate therefor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772933A FI772933A (fi) | 1978-04-13 |
| FI63570B FI63570B (fi) | 1983-03-31 |
| FI63570C true FI63570C (fi) | 1983-07-11 |
Family
ID=11049169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772933A FI63570C (fi) | 1976-10-12 | 1977-10-05 | Foerfarande foer framstaellning av n'-(2'-furanidyl)-5-fluor-uracil d v s ftorafur |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4174446A (da) |
| JP (2) | JPS5346960A (da) |
| AT (1) | AT363101B (da) |
| AU (1) | AU508758B2 (da) |
| BE (1) | BE859529A (da) |
| CH (1) | CH637127A5 (da) |
| DE (1) | DE2744956A1 (da) |
| DK (1) | DK143230C (da) |
| ES (1) | ES463072A1 (da) |
| FI (1) | FI63570C (da) |
| FR (1) | FR2367762A1 (da) |
| GB (1) | GB1554393A (da) |
| IL (1) | IL50671A (da) |
| NL (1) | NL7711171A (da) |
| NO (1) | NO146911C (da) |
| NZ (1) | NZ185348A (da) |
| RO (1) | RO72832A (da) |
| SE (1) | SE7711381L (da) |
| YU (1) | YU243177A (da) |
| ZA (1) | ZA776011B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6135521Y2 (da) * | 1981-01-16 | 1986-10-16 | ||
| JPS57199883A (en) * | 1981-06-03 | 1982-12-07 | Teijin Ltd | Deep color process of fabric |
| JP2009102076A (ja) * | 2009-01-05 | 2009-05-14 | Masayuki Makita | ボトルキャップ |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1976
- 1976-10-12 IL IL50671A patent/IL50671A/xx unknown
-
1977
- 1977-10-05 FI FI772933A patent/FI63570C/fi not_active IP Right Cessation
- 1977-10-05 JP JP12044777A patent/JPS5346960A/ja active Pending
- 1977-10-05 NZ NZ185348A patent/NZ185348A/xx unknown
- 1977-10-05 JP JP12044677A patent/JPS5346987A/ja active Pending
- 1977-10-05 ES ES463072A patent/ES463072A1/es not_active Expired
- 1977-10-06 DE DE19772744956 patent/DE2744956A1/de not_active Withdrawn
- 1977-10-06 GB GB41580/77A patent/GB1554393A/en not_active Expired
- 1977-10-07 ZA ZA00776011A patent/ZA776011B/xx unknown
- 1977-10-10 BE BE181577A patent/BE859529A/xx not_active IP Right Cessation
- 1977-10-10 DK DK449477A patent/DK143230C/da not_active IP Right Cessation
- 1977-10-10 SE SE7711381A patent/SE7711381L/xx not_active Application Discontinuation
- 1977-10-10 YU YU02431/77A patent/YU243177A/xx unknown
- 1977-10-11 NO NO773463A patent/NO146911C/no unknown
- 1977-10-11 RO RO7791810A patent/RO72832A/ro unknown
- 1977-10-11 NL NL7711171A patent/NL7711171A/xx not_active Application Discontinuation
- 1977-10-11 CH CH1239577A patent/CH637127A5/de not_active IP Right Cessation
- 1977-10-11 US US05/841,023 patent/US4174446A/en not_active Expired - Lifetime
- 1977-10-11 AT AT0725277A patent/AT363101B/de not_active IP Right Cessation
- 1977-10-12 FR FR7730685A patent/FR2367762A1/fr active Granted
- 1977-10-12 AU AU29618/77A patent/AU508758B2/en not_active Expired
-
1979
- 1979-04-30 US US06/034,422 patent/US4212814A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FI63570B (fi) | 1983-03-31 |
| FI772933A (fi) | 1978-04-13 |
| GB1554393A (en) | 1979-10-17 |
| AT363101B (de) | 1981-07-10 |
| NO146911B (no) | 1982-09-20 |
| YU243177A (en) | 1983-01-21 |
| DE2744956A1 (de) | 1978-04-13 |
| JPS5346987A (en) | 1978-04-27 |
| ES463072A1 (es) | 1978-11-16 |
| CH637127A5 (de) | 1983-07-15 |
| NZ185348A (en) | 1980-04-28 |
| FR2367762B1 (da) | 1982-03-05 |
| AU508758B2 (en) | 1980-04-03 |
| ATA725277A (de) | 1980-12-15 |
| BE859529A (fr) | 1978-04-10 |
| ZA776011B (en) | 1978-11-29 |
| RO72832A (ro) | 1982-09-09 |
| DK449477A (da) | 1978-04-13 |
| SE7711381L (sv) | 1978-04-13 |
| JPS5346960A (en) | 1978-04-27 |
| FR2367762A1 (fr) | 1978-05-12 |
| NO146911C (no) | 1982-12-29 |
| AU2961877A (en) | 1979-04-26 |
| NL7711171A (nl) | 1978-04-14 |
| NO773463L (no) | 1978-04-13 |
| US4212814A (en) | 1980-07-15 |
| DK143230C (da) | 1981-11-30 |
| DK143230B (da) | 1981-07-27 |
| IL50671A (en) | 1980-03-31 |
| IL50671A0 (en) | 1976-12-31 |
| US4174446A (en) | 1979-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: ABIC LTD. |