BE565282A - - Google Patents
Info
- Publication number
- BE565282A BE565282A BE565282DA BE565282A BE 565282 A BE565282 A BE 565282A BE 565282D A BE565282D A BE 565282DA BE 565282 A BE565282 A BE 565282A
- Authority
- BE
- Belgium
- Prior art keywords
- methyl
- group
- tetrahydrofuran
- oxo
- converted
- Prior art date
Links
- -1 2-methyl-3-hydroxy-tetrahydrofuran-5-carboxylic acid dimethylamide Chemical compound 0.000 claims description 27
- 238000006722 reduction reaction Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- 230000000875 corresponding Effects 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000000468 ketone group Chemical group 0.000 claims description 9
- MQZOYKWIDAOENK-UHFFFAOYSA-N 5-methyl-4-oxooxolane-2-carboxylic acid Chemical compound CC1OC(C(O)=O)CC1=O MQZOYKWIDAOENK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000004036 acetal group Chemical group 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Chemical compound [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 claims description 6
- YNOGYQAEJGADFJ-UHFFFAOYSA-O oxolan-2-ylmethylazanium Chemical class [NH3+]CC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-O 0.000 claims description 5
- 238000006359 acetalization reaction Methods 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- 150000004681 metal hydrides Chemical class 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- RYHWIGJYXWKNHY-UHFFFAOYSA-N 5-(aminomethyl)-2-methyloxolan-3-ol Chemical compound CC1OC(CN)CC1O RYHWIGJYXWKNHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- ZWCFPVVHRISJNF-UHFFFAOYSA-N 4-hydroxy-5-methyloxolane-2-carboxylic acid Chemical compound CC1OC(C(O)=O)CC1O ZWCFPVVHRISJNF-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000012022 methylating agents Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000001241 acetals Chemical class 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 230000001131 transforming Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- ZTZMUUSDSRMEDM-UHFFFAOYSA-N methyl 5-methyl-4-oxooxolane-2-carboxylate Chemical compound COC(=O)C1CC(=O)C(C)O1 ZTZMUUSDSRMEDM-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 4
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- UQOFGTXDASPNLL-UHFFFAOYSA-N (2S,4R,5S)-Muscarine Chemical compound CC1OC(C[N+](C)(C)C)CC1O UQOFGTXDASPNLL-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L Barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WGWHQILKSZRLDQ-UHFFFAOYSA-N CC1OC(CC1(OC)OC)C(=O)N(C)C Chemical compound CC1OC(CC1(OC)OC)C(=O)N(C)C WGWHQILKSZRLDQ-UHFFFAOYSA-N 0.000 description 2
- WUOOMJSTTFTWGG-UHFFFAOYSA-N CC1OC(CC1(OC)OC)CO Chemical compound CC1OC(CC1(OC)OC)CO WUOOMJSTTFTWGG-UHFFFAOYSA-N 0.000 description 2
- FTTIZABOGGBXKB-UHFFFAOYSA-N CC1OC(CC1(OC)OC)COS(=O)(=O)C1=CC=C(C)C=C1 Chemical compound CC1OC(CC1(OC)OC)COS(=O)(=O)C1=CC=C(C)C=C1 FTTIZABOGGBXKB-UHFFFAOYSA-N 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M Silver chloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N Trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N Trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- WUFRNEJYZWHXLC-UHFFFAOYSA-M (4-hydroxy-5-methyloxolan-2-yl)methyl-trimethylazanium;chloride Chemical compound [Cl-].CC1OC(C[N+](C)(C)C)CC1O WUFRNEJYZWHXLC-UHFFFAOYSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YDRWXKNFHCZTJF-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-N-methylethanamine;hydroiodide Chemical class [I-].C[NH2+]CCC1=CC=C(OC)C(OC)=C1 YDRWXKNFHCZTJF-UHFFFAOYSA-N 0.000 description 1
- WOLOBPUZOUBNCH-UHFFFAOYSA-N 5-(iodomethyl)-3,3-dimethoxy-2-methyloxolane Chemical compound COC1(OC)CC(CI)OC1C WOLOBPUZOUBNCH-UHFFFAOYSA-N 0.000 description 1
- RRJMVBOQGJYNPF-UHFFFAOYSA-N 5-[(dimethylamino)methyl]-2-methyloxolan-3-ol Chemical compound CC1OC(CN(C)C)CC1O RRJMVBOQGJYNPF-UHFFFAOYSA-N 0.000 description 1
- ZFZWXIOZZVTDFD-UHFFFAOYSA-N 5-[(dimethylamino)methyl]-2-methyloxolan-3-one Chemical compound CC1OC(CN(C)C)CC1=O ZFZWXIOZZVTDFD-UHFFFAOYSA-N 0.000 description 1
- 229960004373 Acetylcholine Drugs 0.000 description 1
- 241000134914 Amanita muscaria Species 0.000 description 1
- UCOIECPRWIJUMK-UHFFFAOYSA-N CC1OC(CC1(OC)OC)CCl Chemical compound CC1OC(CC1(OC)OC)CCl UCOIECPRWIJUMK-UHFFFAOYSA-N 0.000 description 1
- SFZIGYHGVHQSCK-UHFFFAOYSA-N CC1OC(CC1=O)C(=O)N(C)C Chemical compound CC1OC(CC1=O)C(=O)N(C)C SFZIGYHGVHQSCK-UHFFFAOYSA-N 0.000 description 1
- COBBZOXSSFQTKE-UHFFFAOYSA-N CC1OC(CC1=O)CN Chemical compound CC1OC(CC1=O)CN COBBZOXSSFQTKE-UHFFFAOYSA-N 0.000 description 1
- AIYUHDOJVYHVIT-UHFFFAOYSA-M Caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 1
- OZWKMVRBQXNZKK-UHFFFAOYSA-N Ketorolac Chemical group OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
- UQOFGTXDASPNLL-XHNCKOQMSA-N Muscarine Chemical compound C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O UQOFGTXDASPNLL-XHNCKOQMSA-N 0.000 description 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Orthoformic acid Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
- 229940083599 Sodium Iodide Drugs 0.000 description 1
- ZFVWBUVYNPLIIS-UHFFFAOYSA-N Tetrahydro-2-methyl-3-furanol Chemical compound CC1OCCC1O ZFVWBUVYNPLIIS-UHFFFAOYSA-N 0.000 description 1
- 239000005703 Trimethylamine hydrochloride Substances 0.000 description 1
- HQNWNXASNSAXLV-UHFFFAOYSA-N [B+3].[H-].[Na+].[H-].[H-].[H-] Chemical compound [B+3].[H-].[Na+].[H-].[H-].[H-] HQNWNXASNSAXLV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229940098124 cesium chloride Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000002140 halogenating Effects 0.000 description 1
- KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical group C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE565282A true BE565282A (xx) |
Family
ID=185847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE565282D BE565282A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE565282A (xx) |
-
0
- BE BE565282D patent/BE565282A/fr unknown
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