CA1053686A - Furane derivatives and production thereof - Google Patents
Furane derivatives and production thereofInfo
- Publication number
- CA1053686A CA1053686A CA202,704A CA202704A CA1053686A CA 1053686 A CA1053686 A CA 1053686A CA 202704 A CA202704 A CA 202704A CA 1053686 A CA1053686 A CA 1053686A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- hydrogen
- group
- carbon atoms
- compound
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 150000002240 furans Chemical class 0.000 title description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- -1 sodium tetrahydroborate Chemical compound 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- SVNYWXLUVGKHJN-UHFFFAOYSA-N 1-(5-methylfuran-2-yl)oct-1-en-3-one Chemical compound CCCCCC(=O)C=CC1=CC=C(C)O1 SVNYWXLUVGKHJN-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007818 Grignard reagent Substances 0.000 claims description 2
- 150000004795 grignard reagents Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 238000003747 Grignard reaction Methods 0.000 claims 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000002541 furyl group Chemical group 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 238000004821 distillation Methods 0.000 description 20
- 239000003921 oil Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 239000000839 emulsion Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- FHVMRBDWSFCISO-UHFFFAOYSA-N methyl 8-[5-(3-oxooct-1-enyl)furan-2-yl]octanoate Chemical compound CCCCCC(=O)C=CC1=CC=C(CCCCCCCC(=O)OC)O1 FHVMRBDWSFCISO-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- YKGORFVWCDOEGO-UHFFFAOYSA-N 8-[5-(3-oxooct-1-enyl)furan-2-yl]octanoic acid Chemical compound CCCCCC(=O)C=CC1=CC=C(CCCCCCCC(O)=O)O1 YKGORFVWCDOEGO-UHFFFAOYSA-N 0.000 description 4
- ITXZBSMMKKOOQN-UHFFFAOYSA-N 8-[5-(3-oxooctyl)furan-2-yl]octanoic acid Chemical compound CCCCCC(=O)CCC1=CC=C(CCCCCCCC(O)=O)O1 ITXZBSMMKKOOQN-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- FCVMAXLARFVTEB-UHFFFAOYSA-N methyl 8-[5-(3-hydroxy-3-methyloctyl)furan-2-yl]octanoate Chemical compound CCCCCC(C)(O)CCC1=CC=C(CCCCCCCC(=O)OC)O1 FCVMAXLARFVTEB-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- ZIOZYRSDNLNNNJ-IBGZPJMESA-N (12s)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid Chemical compound CCCCCC=CC[C@H](OO)C=CC=CCC=CCCCC(O)=O ZIOZYRSDNLNNNJ-IBGZPJMESA-N 0.000 description 1
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 1
- YJDNVKFUJMKXFR-UHFFFAOYSA-N 1-(5-methylfuran-2-yl)oct-1-en-3-ol Chemical compound CCCCCC(O)C=CC1=CC=C(C)O1 YJDNVKFUJMKXFR-UHFFFAOYSA-N 0.000 description 1
- LQZCYXCHWNQBKX-UHFFFAOYSA-N 1-dimethoxyphosphorylheptan-2-one Chemical compound CCCCCC(=O)CP(=O)(OC)OC LQZCYXCHWNQBKX-UHFFFAOYSA-N 0.000 description 1
- XHNZBOQQCNCBBC-UHFFFAOYSA-N 4,7-ditert-butyl-1,3-benzodioxole Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C2=C1OCO2 XHNZBOQQCNCBBC-UHFFFAOYSA-N 0.000 description 1
- PFJFNQUFMTYCHB-UHFFFAOYSA-N C[SiH2]N[SiH3] Chemical compound C[SiH2]N[SiH3] PFJFNQUFMTYCHB-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YMWBTMBPEHUMBA-FAKHFBMMSA-N [(3r,3as,4s,8as)-3-hydroxy-6,8a-dimethyl-8-oxo-3-propan-2-yl-2,3a,4,5-tetrahydro-1h-azulen-4-yl] (e)-2-methylbut-2-enoate Chemical compound C\C=C(/C)C(=O)O[C@H]1CC(C)=CC(=O)[C@@]2(C)CC[C@@](O)(C(C)C)[C@H]12 YMWBTMBPEHUMBA-FAKHFBMMSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- WEZZCDZRFLUCRU-UHFFFAOYSA-N methyl 8-[5-(3-oxooctyl)furan-2-yl]octanoate Chemical compound CCCCCC(=O)CCC1=CC=C(CCCCCCCC(=O)OC)O1 WEZZCDZRFLUCRU-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D307/10—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2924173A GB1466256A (en) | 1973-06-20 | 1973-06-20 | 2,5-substituted furans and their production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053686A true CA1053686A (en) | 1979-05-01 |
Family
ID=10288383
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA202,704A Expired CA1053686A (en) | 1973-06-20 | 1974-06-18 | Furane derivatives and production thereof |
| CA202,705A Expired CA1052801A (en) | 1973-06-20 | 1974-06-18 | Tetrahydrofurane derivatives and production thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA202,705A Expired CA1052801A (en) | 1973-06-20 | 1974-06-18 | Tetrahydrofurane derivatives and production thereof |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS5032165A (enExample) |
| BE (2) | BE816569A (enExample) |
| CA (2) | CA1053686A (enExample) |
| DD (2) | DD113356A5 (enExample) |
| DE (2) | DE2429247A1 (enExample) |
| DK (2) | DK329674A (enExample) |
| FI (2) | FI187474A7 (enExample) |
| FR (2) | FR2234301B1 (enExample) |
| GB (1) | GB1466256A (enExample) |
| IL (2) | IL45065A (enExample) |
| NL (2) | NL7408200A (enExample) |
| NO (2) | NO742234L (enExample) |
| SE (2) | SE7408097L (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03502882A (ja) * | 1987-12-15 | 1991-07-04 | ザ トラスティーズ オブ プリンストン ユニヴァーシティ | 変異原物質および発癌物質に関するトランスジェニック試験システム |
-
1973
- 1973-06-20 GB GB2924173A patent/GB1466256A/en not_active Expired
-
1974
- 1974-06-18 CA CA202,704A patent/CA1053686A/en not_active Expired
- 1974-06-18 CA CA202,705A patent/CA1052801A/en not_active Expired
- 1974-06-19 FI FI1874/74A patent/FI187474A7/fi unknown
- 1974-06-19 IL IL45065A patent/IL45065A/xx unknown
- 1974-06-19 FI FI1873/74A patent/FI187374A7/fi unknown
- 1974-06-19 BE BE145628A patent/BE816569A/xx unknown
- 1974-06-19 NO NO742234A patent/NO742234L/no unknown
- 1974-06-19 NO NO742235A patent/NO742235L/no unknown
- 1974-06-19 IL IL45066A patent/IL45066A/en unknown
- 1974-06-19 DD DD179283A patent/DD113356A5/xx unknown
- 1974-06-19 JP JP49069267A patent/JPS5032165A/ja active Pending
- 1974-06-19 NL NL7408200A patent/NL7408200A/xx not_active Application Discontinuation
- 1974-06-19 SE SE7408097A patent/SE7408097L/xx unknown
- 1974-06-19 DD DD179281A patent/DD112755A5/xx unknown
- 1974-06-19 BE BE145629A patent/BE816570A/xx unknown
- 1974-06-19 FR FR7421232A patent/FR2234301B1/fr not_active Expired
- 1974-06-19 JP JP49069266A patent/JPS5032164A/ja active Pending
- 1974-06-19 DE DE2429247A patent/DE2429247A1/de active Pending
- 1974-06-19 SE SE7408096A patent/SE7408096L/xx unknown
- 1974-06-19 DE DE2429248A patent/DE2429248A1/de active Pending
- 1974-06-19 NL NL7408199A patent/NL7408199A/xx not_active Application Discontinuation
- 1974-06-19 FR FR7421231A patent/FR2234302B1/fr not_active Expired
- 1974-06-20 DK DK329674A patent/DK329674A/da unknown
- 1974-06-20 DK DK329874A patent/DK329874A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2234301B1 (enExample) | 1978-09-22 |
| FR2234301A1 (enExample) | 1975-01-17 |
| IL45065A0 (en) | 1974-09-10 |
| JPS5032164A (enExample) | 1975-03-28 |
| BE816570A (fr) | 1974-10-16 |
| FI187374A7 (enExample) | 1974-12-21 |
| IL45066A (en) | 1977-07-31 |
| IL45065A (en) | 1978-06-15 |
| SE7408096L (enExample) | 1974-12-23 |
| DD113356A5 (enExample) | 1975-06-05 |
| FR2234302B1 (enExample) | 1978-12-01 |
| IL45066A0 (en) | 1974-09-10 |
| GB1466256A (en) | 1977-03-02 |
| NL7408199A (enExample) | 1974-12-24 |
| FR2234302A1 (enExample) | 1975-01-17 |
| CA1052801A (en) | 1979-04-17 |
| DK329674A (enExample) | 1975-02-10 |
| DE2429248A1 (de) | 1975-01-16 |
| DK329874A (enExample) | 1975-02-10 |
| NO742234L (enExample) | 1975-01-13 |
| JPS5032165A (enExample) | 1975-03-28 |
| DD112755A5 (enExample) | 1975-05-05 |
| DE2429247A1 (de) | 1975-01-16 |
| NO742235L (enExample) | 1975-01-13 |
| BE816569A (fr) | 1974-10-16 |
| SE7408097L (enExample) | 1974-12-23 |
| NL7408200A (enExample) | 1974-12-24 |
| FI187474A7 (enExample) | 1974-12-21 |
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