BE569686A - - Google Patents
Info
- Publication number
- BE569686A BE569686A BE569686DA BE569686A BE 569686 A BE569686 A BE 569686A BE 569686D A BE569686D A BE 569686DA BE 569686 A BE569686 A BE 569686A
- Authority
- BE
- Belgium
- Prior art keywords
- formula
- amine
- bis
- diaminopentadecane
- preparation
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 34
- 230000003569 amebicidal effect Effects 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 22
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 claims description 13
- -1 alkylene radical Chemical class 0.000 claims description 12
- 229940081310 piperonal Drugs 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000007513 acids Chemical class 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
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 64
- 239000000155 melt Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 230000000694 effects Effects 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241000224489 Amoeba Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229940124323 amoebicide Drugs 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- SSUWRFARPKMZPT-UHFFFAOYSA-N 2,13-dimethyltetradecane-5,10-diamine Chemical compound NC(CCC(C)C)CCCCC(CCC(C)C)N SSUWRFARPKMZPT-UHFFFAOYSA-N 0.000 description 1
- ZEVBKQPODJYIGU-UHFFFAOYSA-N 2,14-dimethylpentadecane-5,11-diamine Chemical compound NC(CCC(C)C)CCCCCC(CCC(C)C)N ZEVBKQPODJYIGU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 208000004881 Amebiasis Diseases 0.000 description 1
- 206010001935 American trypanosomiasis Diseases 0.000 description 1
- 206010001980 Amoebiasis Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000223109 Trypanosoma cruzi Species 0.000 description 1
- 239000000059 antiamebic agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- GUZLQNDQUZUIOC-UHFFFAOYSA-N tetradecane-5,10-diamine Chemical compound CCCCC(N)CCCCC(N)CCCC GUZLQNDQUZUIOC-UHFFFAOYSA-N 0.000 description 1
- 208000037972 tropical disease Diseases 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE569686A true BE569686A (de) |
Family
ID=188545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE569686D BE569686A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE569686A (de) |
-
0
- BE BE569686D patent/BE569686A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR840002021B1 (ko) | 트랜스-4-페닐-1, 2, 3, 4-테트라하이드로-1-나프탈렌아민 유도체의 제조방법 | |
| SU1487810A3 (ru) | СПОСОБ ПОЛУЧЕНИЯ N-[2-(4-ФТОР-. ФЕНИЛ)-1-МЕТИЛ >3ΤΗΠ-Ν-ΜΕΤΗΠ-Ν-ΠΡ0ПИНИЛАМИНА | |
| EP0373998A1 (de) | Propenonoximether, Verfahren zu dessen Herstellung sowie diese enthaltende Arzneinmittel | |
| JPH02167253A (ja) | フェニルアルキルアミノサリチルアミド及びその製造方法 | |
| EP0174242B1 (de) | 1-(Aminophenyl)-2-amino-propanon-Derivate, deren Verwendung in Therapie und Verfahren zu deren Herstellung | |
| FR2663328A1 (fr) | Derives d'hexahydroazepines, un procede pour leur preparation et compositions pharmaceutiques les contenant. | |
| FR2730490A1 (fr) | Derives 1-(2-(vinyl-substitues))-3,4-dihydro-5h-2,3- benzodiazepine | |
| PT92761B (pt) | Processo para preparacao de derivados do benzeno, activos sobre o sistema imunitario | |
| JPH0517900B2 (de) | ||
| EP0211746B1 (de) | Phenyl-Piperazin-Derivate, Verfahren zu deren Herstellung und Verwendung als Heilmittel | |
| FR2553413A1 (fr) | Derives de 4-alkyl-2-hydroxy-3-methyl-2-phenyl-morpholine, procede de preparation et utilisation en therapeutique | |
| EP0061406B1 (de) | Benzamido-alkyl-hydroxamsäurederivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel | |
| EP0065908B1 (de) | ((Alkyl- und Alkenyl-3-piperidyl-4)-2-äthyl)-3-indole und ihre Verwendung als Arzneimittel | |
| EP0322391B1 (de) | Neue Phenylalkylamin-Derivate | |
| FR2476644A1 (fr) | Orthoarylydeneaminophenethylamine, leur preparation et leur utilisation therapeutique | |
| CH627451A5 (en) | Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles | |
| KR960007523B1 (ko) | 4-아릴카르보닐-1-[(4-모르폴리닐)-저급-알킬]-1h-인돌, 그 제조 방법 및 이를 포함한 조성물 | |
| EP0354078B1 (de) | Derivate von Benzocyclohepten, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| CA1223595A (fr) | Derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanamine et de (quinolyl-4)-1 (piperidyl-4)-3 propanamine, procedes pour leur preparation et medicaments les contenant | |
| BE543388A (de) | ||
| BE569697A (de) | ||
| FR2473512A1 (fr) | Nouveaux 2-aminomethyl-6-halogeno-phenols, leur preparation et leur application comme medicaments | |
| LU84194A1 (fr) | Nouveaux derives d'amino-2 phenethylamines,leur methode de preparation et leur application therapeutique | |
| FR2504138A1 (fr) | Procede de preparation de l'isoquinuclidine | |
| BE536124A (de) |