BE559564A - - Google Patents
Info
- Publication number
- BE559564A BE559564A BE559564DA BE559564A BE 559564 A BE559564 A BE 559564A BE 559564D A BE559564D A BE 559564DA BE 559564 A BE559564 A BE 559564A
- Authority
- BE
- Belgium
- Prior art keywords
- gamma
- group
- beta
- esters
- sep
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000005204 hydroxybenzenes Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- -1 dimethylaminomethylen Chemical class 0.000 claims description 9
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 230000000875 corresponding Effects 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000003857 carboxamides Chemical group 0.000 claims 2
- SMGLHFBQMBVRCP-UHFFFAOYSA-N 3-hydroxypropanamide Chemical compound NC(=O)CCO SMGLHFBQMBVRCP-UHFFFAOYSA-N 0.000 claims 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 210000003169 Central Nervous System Anatomy 0.000 description 7
- BGBFVIKSTCLLDW-UHFFFAOYSA-N N,N-diethyl-2-(2-methoxy-6-prop-2-enylphenoxy)ethanamine Chemical compound CCN(CC)CCOC1=C(CC=C)C=CC=C1OC BGBFVIKSTCLLDW-UHFFFAOYSA-N 0.000 description 7
- 210000004291 Uterus Anatomy 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 230000001624 sedative Effects 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000004899 motility Effects 0.000 description 4
- 239000001184 potassium carbonate Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-Dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 2
- LHJZSWVADJCBNI-UHFFFAOYSA-N 2-methoxy-5-prop-1-enylphenol Chemical compound COC1=CC=C(C=CC)C=C1O LHJZSWVADJCBNI-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M Sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- BJIOGJUNALELMI-UHFFFAOYSA-N isoeugenol Chemical compound COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- CRPTXKKKIGGDBX-UHFFFAOYSA-N (Z)-but-2-ene Chemical group [CH2]C=CC CRPTXKKKIGGDBX-UHFFFAOYSA-N 0.000 description 1
- VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-Chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-N,N-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
- JQDXZJYAUSVHDH-UHFFFAOYSA-N 3-chloropropanamide Chemical compound NC(=O)CCCl JQDXZJYAUSVHDH-UHFFFAOYSA-N 0.000 description 1
- ZQPSHYPSWNKGNF-UHFFFAOYSA-N 3-methoxy-2-prop-2-enylphenol Chemical compound COC1=CC=CC(O)=C1CC=C ZQPSHYPSWNKGNF-UHFFFAOYSA-N 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N Arsine Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- UZKLBUBIOBUPBA-UHFFFAOYSA-N BrCCCOC1=C(C=CC(=C1)C=CC)OC Chemical compound BrCCCOC1=C(C=CC(=C1)C=CC)OC UZKLBUBIOBUPBA-UHFFFAOYSA-N 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N Chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 206010018987 Haemorrhage Diseases 0.000 description 1
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Chemical compound COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
- 206010061920 Psychotic disease Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000593 degrading Effects 0.000 description 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000070 megaphenic Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003010 neurosedative Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000008855 peristalsis Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940075581 sodium bromide Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE559564A true BE559564A (es) |
Family
ID=182200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE559564D BE559564A (es) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE559564A (es) |
-
0
- BE BE559564D patent/BE559564A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2504127A1 (fr) | Nouveaux derives d'acides phenyl aliphatique carboxyliques, procede pour leur preparation et leur application comme medicaments | |
| EP0022408A1 (fr) | Nouveaux dérivés de l'alpha-phényl 2-pyrrolidineméthanol et leurs sels, procédé de préparation, application à titre de médicaments et compositions les renfermant | |
| EP0074873B1 (fr) | Dérivés de phénoxy-3 propanol-2, leur préparation et leur application en thérapeutique | |
| EP0486385A1 (fr) | Dérivés d'imidazole, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
| BE779775A (fr) | Derives de l'uree, procede pour les preparer et leurs applications | |
| CA1217489A (fr) | Derives de la piperidine et leurs procedes de preparation | |
| BE559564A (es) | ||
| EP0061379B1 (fr) | Dérivés de pyridine, leur préparation et leur application en thérapeutique | |
| CH624089A5 (es) | ||
| BE806848A (fr) | Medicament a base d'un derive de la quinoleine | |
| EP0275221B1 (fr) | Nouveaux dérivés du N-(1H-indol 4-yl) benzamide ainsi que leurs sels, leur application à titre de médicaments et les compositions les renfermant | |
| CH625507A5 (es) | ||
| BE583205A (es) | ||
| EP0022022A1 (fr) | Nouveaux dérivés acylés de la taurine et leurs sels et procédé pour leur préparation | |
| EP0226475A1 (fr) | Nouveaux dérivés de la diphénoxyethylamine, leur procédé d'obtention et les compositions pharmaceutiques en renfermant | |
| CH629796A5 (en) | Therapeutically active compounds of 4-(2-thienylmethylamino)benzoic acid | |
| BE541651A (es) | ||
| BE516840A (es) | ||
| BE533436A (es) | ||
| BE503775A (es) | ||
| FR2524881A1 (fr) | Nouvelles indole-alkylene-amines substituees, leur preparation et leur utilisation comme medicaments | |
| FR2473512A1 (fr) | Nouveaux 2-aminomethyl-6-halogeno-phenols, leur preparation et leur application comme medicaments | |
| BE580872A (es) | ||
| BE482321A (es) | ||
| BE837320A (fr) | Derives ethers de 3-amino-1,2-propanodiol |