DE2429247A1 - Tetrahydrofuranderivate und verfahren zu deren herstellung - Google Patents
Tetrahydrofuranderivate und verfahren zu deren herstellungInfo
- Publication number
- DE2429247A1 DE2429247A1 DE2429247A DE2429247A DE2429247A1 DE 2429247 A1 DE2429247 A1 DE 2429247A1 DE 2429247 A DE2429247 A DE 2429247A DE 2429247 A DE2429247 A DE 2429247A DE 2429247 A1 DE2429247 A1 DE 2429247A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- group
- compounds according
- pentyl
- carbon atoms
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 238000003747 Grignard reaction Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 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 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000004458 analytical method Methods 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 239000012230 colorless oil Substances 0.000 description 15
- 238000004821 distillation Methods 0.000 description 10
- JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical compound CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 description 10
- -1 5-dimethoxymethyl-tetrahydro-2-furyl Chemical group 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- 239000012259 ether extract Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 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
- ZJTPMIDURCBBTK-UHFFFAOYSA-N methyl 8-(5-formyloxolan-2-yl)octanoate Chemical compound COC(=O)CCCCCCCC1CCC(C=O)O1 ZJTPMIDURCBBTK-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000005051 trimethylchlorosilane Substances 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
- YEJOEVSVZNHDBJ-UHFFFAOYSA-N 2-oxoheptyl dihydrogen phosphate Chemical compound CCCCCC(=O)COP(O)(O)=O YEJOEVSVZNHDBJ-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101100286286 Dictyostelium discoideum ipi gene Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000003529 luteolytic effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- KVERUONTDNOFQL-UHFFFAOYSA-N methyl 8-[5-(dimethoxymethyl)oxolan-2-yl]octanoate Chemical compound COC(OC)C1CCC(CCCCCCCC(=O)OC)O1 KVERUONTDNOFQL-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- GBECUEIQVRDUKB-UHFFFAOYSA-M thallium monochloride Chemical compound [Tl]Cl GBECUEIQVRDUKB-UHFFFAOYSA-M 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 101150072193 traB gene Proteins 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 |
|---|---|
| DE2429247A1 true DE2429247A1 (de) | 1975-01-16 |
Family
ID=10288383
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2429247A Pending DE2429247A1 (de) | 1973-06-20 | 1974-06-19 | Tetrahydrofuranderivate und verfahren zu deren herstellung |
| DE2429248A Pending DE2429248A1 (de) | 1973-06-20 | 1974-06-19 | Furanderivate und verfahren zu deren herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2429248A Pending DE2429248A1 (de) | 1973-06-20 | 1974-06-19 | Furanderivate und verfahren zu deren herstellung |
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 |
|---|---|
| CA1053686A (en) | 1979-05-01 |
| 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 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2126236A1 (de) | Neue Cyclopentanderivate | |
| DE2627704C2 (de) | Bicycloheptenverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE2723237A1 (de) | 12-azaprostansaeuren | |
| DE2150361A1 (de) | Prostanoesaeurederivate | |
| DE2359891A1 (de) | Verfahren zur herstellung von furanonderivaten | |
| DE2032919A1 (de) | Verfahren zur Herstellung von Polyen verbindungen | |
| DE2424806A1 (de) | Antikoagulantien, verfahren zu ihrer herstellung und ihre verwendung | |
| DE3034040C2 (de) | Verfahren zur Herstellung von Muscon, 16-Oxa-14-methyl-bicyclo[10.3.1]-hexadec-1-en als Zwischenprodukt für dieses Verfahren und ein Verfahren zu dessen Herstellung | |
| DE2319017C3 (de) | Verfahren zur Herstellung von Prostaglandinen der Eins-Reihe | |
| DE2429247A1 (de) | Tetrahydrofuranderivate und verfahren zu deren herstellung | |
| DE2044698A1 (de) | Verfahren zur Herstellung von Cyclopentandenvaten | |
| DE2739277A1 (de) | 11-deoxy-11-oxaprostaglandinverbindungen | |
| DE2852975C2 (de) | 5-Cyano-1-alkylpyrrol-2-essigsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE4027241A1 (de) | Verfahren zur herstellung von (alpha)-alkyllactonen | |
| DE3879551T2 (de) | Hydrogenationsverfahren. | |
| DE68909143T2 (de) | Prostaglandin-Vorläufer und ihre Herstellung. | |
| CH638480A5 (de) | Prostaglandinverbindungen. | |
| DE2404306B2 (de) | Optisch aktive Pinanderivate | |
| DE2020762A1 (de) | Azainden-3-niedrigaliphatische-Saeuren und Verfahren zu deren Herstellung | |
| DE69221564T2 (de) | Verfahren zur herstellung 4-substituierter gamma-lactone und so hergestellte neue substanzen | |
| AT359210B (de) | Verfahren zur herstellung von desoxyvincamin- amiden | |
| EP0123113A2 (de) | Chromon- und Thiochromon-8-aldehyde, sowie ein Verfahren zu ihrer Herstellung | |
| DE2024614C3 (de) | Neues Verfahren zur Herstellung von d-trans-Pyrethrinsäure-(1R.2R) | |
| DE2613306C2 (enExample) | ||
| DE1249851B (de) | Morel Ariesheim (Schweiz) j Verfahren zur Herstellung neuer Phenoxyessigsäure amide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |