BE554347A - - Google Patents
Info
- Publication number
- BE554347A BE554347A BE554347DA BE554347A BE 554347 A BE554347 A BE 554347A BE 554347D A BE554347D A BE 554347DA BE 554347 A BE554347 A BE 554347A
- Authority
- BE
- Belgium
- Prior art keywords
- phenyl
- morpholino
- butanol
- ethyl
- ethyl7
- Prior art date
Links
- -1 2-dipropylaminoethyl Chemical group 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 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 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 206010041349 Somnolence Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AZZDBAMLOMKUQR-UHFFFAOYSA-N 1-(diethylamino)butan-1-ol Chemical compound CCCC(O)N(CC)CC AZZDBAMLOMKUQR-UHFFFAOYSA-N 0.000 description 1
- IFGNOHARBDIOII-UHFFFAOYSA-N 4-(dimethylamino)-2-[2-(dimethylamino)ethyl]-2-phenylbutanoic acid Chemical compound CN(C)CCC(CCN(C)C)(C(O)=O)C1=CC=CC=C1 IFGNOHARBDIOII-UHFFFAOYSA-N 0.000 description 1
- 238000006820 Bouveault-Blanc reduction reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 208000032140 Sleepiness Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- VAMOHKZVXBCIKF-UHFFFAOYSA-N ethyl 4-(diethylamino)-2-[2-(diethylamino)ethyl]-2-phenylbutanoate Chemical compound CCN(CC)CCC(C(=O)OCC)(CCN(CC)CC)C1=CC=CC=C1 VAMOHKZVXBCIKF-UHFFFAOYSA-N 0.000 description 1
- CUEIAIGRDVRBNR-UHFFFAOYSA-N ethyl 4-(dimethylamino)-2-[2-(dimethylamino)ethyl]-2-phenylbutanoate Chemical compound CCOC(=O)C(CCN(C)C)(CCN(C)C)C1=CC=CC=C1 CUEIAIGRDVRBNR-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE554347A true BE554347A (d) |
Family
ID=178816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE554347D BE554347A (d) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE554347A (d) |
-
0
- BE BE554347D patent/BE554347A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1720848A1 (fr) | Derives de alkylpiperazine- et alkylhomopiperazine- carboxylates, leur preparation et leur application en tant qu'inhibiteurs de l'enzyme faah | |
| CH622770A5 (en) | Process for the preparation of heterocyclic aminoalcohol derivatives | |
| EP0418933A1 (fr) | Dérivés d'alcadiènes, leurs préparations, les médicaments les contenant et produits intermédiaires | |
| EP0002978B1 (fr) | Dérivés de thiazolidinedione-2,4, leur préparation et leur application en thérapeutique | |
| BE616646A (d) | ||
| FR2534915A1 (fr) | Nouveaux derives de 2-(phenoxymethyl)-morpholine, utilisation en therapeutique et procede de preparation | |
| BE554347A (d) | ||
| CA1196331A (fr) | Derives substitues de la thiamorpholinone et leurs procedes de preparation | |
| EP0037344A1 (fr) | Amino-alcoxy pyrazoles, procédé pour leur préparation, et médicaments les contenant | |
| EP0097546B1 (fr) | Benzhydrylsulfinyléthylamines, procédé de préparation et utilisation en thérapeutique | |
| BE554346A (d) | ||
| EP0929515B1 (fr) | Nouveaux derives de la phenoxyethylamine, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les contenant | |
| CH354084A (fr) | Procédé de préparation de pipérazines | |
| CH420107A (fr) | Procédé de préparation de nouveaux dérivés d'aralcoylaminoalcoylcyclohexanes substitués | |
| BE554918A (d) | ||
| BE482321A (d) | ||
| BE503775A (d) | ||
| BE661226A (fr) | Acides arylacethydroxamiques, amides correspondants et procedes de preparation. | |
| CH515873A (fr) | Procédé de préparation de composés dérivés de l'acide phénoxy-alkyl-carboxylique | |
| BE565079A (d) | ||
| BE551032A (d) | ||
| BE555290A (d) | ||
| BE550894A (d) | ||
| BE530795A (d) | ||
| CH637378A5 (fr) | Benzamides cycloalkylalkyliques. |