BE571842A - - Google Patents
Info
- Publication number
- BE571842A BE571842A BE571842DA BE571842A BE 571842 A BE571842 A BE 571842A BE 571842D A BE571842D A BE 571842DA BE 571842 A BE571842 A BE 571842A
- Authority
- BE
- Belgium
- Prior art keywords
- hydrazine
- alkyl
- aralkyl
- aryl
- general formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- -1 3-phenylcinnamoyl Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- SXTUVELWCHPJMA-UHFFFAOYSA-N 3-hydroxy-3,3-diphenylpropanehydrazide Chemical compound C=1C=CC=CC=1C(O)(CC(=O)NN)C1=CC=CC=C1 SXTUVELWCHPJMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 230000001264 neutralization Effects 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PLNNJQXIITYYTN-UHFFFAOYSA-N 2-methylpropanehydrazide Chemical compound CC(C)C(=O)NN PLNNJQXIITYYTN-UHFFFAOYSA-N 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N Barbituric acid Chemical class O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N Benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000001773 anti-convulsant Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- CPOPSLBZVNIING-UHFFFAOYSA-N ethyl 3-hydroxy-3,3-diphenylpropanoate Chemical compound C=1C=CC=CC=1C(O)(CC(=O)OCC)C1=CC=CC=C1 CPOPSLBZVNIING-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
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- SCZGZDLUGUYLRV-UHFFFAOYSA-N (2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NN SCZGZDLUGUYLRV-UHFFFAOYSA-N 0.000 description 1
- YBBSKAGTEPBSNK-UHFFFAOYSA-N 2,2-diphenylacetohydrazide Chemical compound C=1C=CC=CC=1C(C(=O)NN)C1=CC=CC=C1 YBBSKAGTEPBSNK-UHFFFAOYSA-N 0.000 description 1
- YAQLSKVCTLCIIE-UHFFFAOYSA-M 2-bromobutanoate Chemical compound CCC(Br)C([O-])=O YAQLSKVCTLCIIE-UHFFFAOYSA-M 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WFBRYBSJIVIVJT-UHFFFAOYSA-N C1(=CC=CC=C1)C=1C=C(C=CC(=O)NNC=O)C=CC1 Chemical compound C1(=CC=CC=C1)C=1C=C(C=CC(=O)NNC=O)C=CC1 WFBRYBSJIVIVJT-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N Ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229940042795 Hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- HIRPBEGJCGOCKI-UHFFFAOYSA-N ethane;zinc Chemical compound [Zn].[CH2-]C HIRPBEGJCGOCKI-UHFFFAOYSA-N 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VMFUMDXVTKTZQY-UHFFFAOYSA-N naphthalene-1-carbohydrazide Chemical compound C1=CC=C2C(C(=O)NN)=CC=CC2=C1 VMFUMDXVTKTZQY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PJBQYCIDGYKEMN-UHFFFAOYSA-N pentanehydrazide Chemical class CCCCC(=O)NN PJBQYCIDGYKEMN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE571842A true BE571842A (sv) |
Family
ID=189884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE571842D BE571842A (sv) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE571842A (sv) |
-
0
- BE BE571842D patent/BE571842A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0591057B1 (fr) | Arylalkyl(thio)amides ayant une affinité sélective pour les récepteurs de la mélatonine et leur procédé de préparation | |
| EP0001534B1 (fr) | Nouveaux dérivés du pyrrole, leur procédé de préparation et leurs applications en thérapeutique | |
| EP0248734A1 (fr) | Dérivés de benzo[b]thiophène et benzo[b]furannecarboxamides, leurs procédés de préparation et les médicaments les contenant | |
| CH616161A5 (sv) | ||
| EP0008249A2 (fr) | Dérivés de fluorènes et fluoranthènes, leur procédé de préparation et leur application en thérapeutique | |
| FR2676057A1 (fr) | Derives de 1,2-dithiole-3-thione, procede de preparation de ces derives, ainsi que l'utilisation de ces derives comme intermediaires de synthese ou comme medicaments. | |
| BE779775A (fr) | Derives de l'uree, procede pour les preparer et leurs applications | |
| BE884387A (fr) | Composition a base d'acides aryloxyalkylaminobenzoiques, leurs sels et leurs esters | |
| BE571842A (sv) | ||
| CH594650A5 (en) | Antiinflammatory (1,2)-benzothiazine derivs. prepn. | |
| BE571404A (sv) | ||
| CH392483A (fr) | Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques | |
| CH644603A5 (en) | Aurone derivatives and process for their preparation | |
| BE563113A (sv) | ||
| BE503348A (sv) | ||
| BE706623A (sv) | ||
| EP0233801A1 (fr) | Nouveaux amides substitués, leur préparation et les compositions pharmaceutiques qui les contiennent | |
| BE474887A (sv) | ||
| BE528490A (sv) | ||
| FR2473512A1 (fr) | Nouveaux 2-aminomethyl-6-halogeno-phenols, leur preparation et leur application comme medicaments | |
| FR2528832A1 (fr) | Nouveaux derives du benzene, leur preparation et leur utilisation comme medicaments | |
| BE519639A (sv) | ||
| BE878185A (fr) | Derives de 1-phtalazone, leur procede de preparation et leur utilisation | |
| BE887039A (fr) | Nouveaux 2-aminomethyl-6-halogeno-phenols, leur preparation et leur application comme medicaments | |
| BE630571A (sv) |