CH396884A - Process for making new hydrazones - Google Patents
Process for making new hydrazonesInfo
- Publication number
- CH396884A CH396884A CH1488864A CH1488864A CH396884A CH 396884 A CH396884 A CH 396884A CH 1488864 A CH1488864 A CH 1488864A CH 1488864 A CH1488864 A CH 1488864A CH 396884 A CH396884 A CH 396884A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- formula
- salts
- compounds
- making new
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 150000007857 hydrazones Chemical class 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 3
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- KYEMJVGXLJXCSM-UHFFFAOYSA-N 1-[3-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=CC(C(C)=O)=C1 KYEMJVGXLJXCSM-UHFFFAOYSA-N 0.000 description 1
- WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
- PNJJKWLRMWJONM-UHFFFAOYSA-N 2,2,3-trihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)(O)C(O)=O PNJJKWLRMWJONM-UHFFFAOYSA-N 0.000 description 1
- VBAVUJVITOLCFI-UHFFFAOYSA-N 2-[1-[4-(dimethylamino)phenyl]ethylideneamino]guanidine Chemical compound CN(C)C1=CC=C(C(C)=NN=C(N)N)C=C1 VBAVUJVITOLCFI-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- XDXFALYQLCMAQN-WLHGVMLRSA-N butanedioic acid;(e)-but-2-enedioic acid Chemical compound OC(=O)CCC(O)=O.OC(=O)\C=C\C(O)=O XDXFALYQLCMAQN-WLHGVMLRSA-N 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
- 239000012876 carrier material Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung neuer Hydrazone Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Guanylhydrazonen der Formel
EMI1.1
worin R Wasserstoff oder Methyl und Ph einen Phenylenrest bedeutet, oder ihren Salzen.
In den neuen Verbindungen kann der Phenylenrest Ph unsubstituiert oder substituiert sein, z. B. durch Niederalkylreste, wie Methyl, Aethyl-, oder i-Propyl-, gerade oder verzweigte, in n beliebiger Stel- lung verbundene Butyl-, Pentyl- oder Hexylreste, Niederalkoxyreste, wie Methoxy-, Aethoxy-, Propoxyoder Butoxyreste, Halogen-niederaikylreste, wie Trifluormethylreste, oder Halogenatome, wie Fluor-, Chlor- oder Bromatome.
Die neuen Hydrazone und ihre Salze besitzen wertvolle pharmakologische Eigenschaften. So zeigen sie z. B. eine antiinflammatorische Wirkung. Sie können daher als Heilmittel in der Human- oder Veterinärmedizin bei entzündlichen Prozessen verwendet werden. Sie sind aber auch als Zwischenprodukte für die Herstellung von Heilmitteln wertvoll.
Besonders hervorzuheben sind die Verbindungen der Formel
EMI1.2
oder der Formel
EMI1.3
worin R Methyl oder Wasserstoff bedeutet, und ihre Salze und insbesondere das p-Dimethylamino-acetophenon-guanylhydrazon und seine Salze.
Das erfindungsgemässe Verfahren zur Hertellung der neuen Verbindungen ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI2.1
worin Ph und R die angegebenen Bedeutungen haben oder ein Salz davon mit einem verätherten Isoharnstoff oder Isothioharnstoff, z. B. einem S-Alkyi-iso- thioharnstoff oder einem O-Alkyl-isoharnstoff, oder Cyanamid oder einem l-Guanylpyrazol oder einem Salz dieser Verbindungen, vorzugsweise einem Salz mit einer Mineralsäure, wie einer Halogenwasserstoff säure, umsetzt.
Die genannte Reaktion kann in üblicher Weise durchgeführt werden.
Die Ausgangsstoffe sind bekannt oder lassen sich nach an sich bekannten Methoden herstellen.
Für das genannte Verfahren lassen sich die Ausgangsstoffe auch in Form eines unter den Reaktionsbedingungen gebildeten Reaktionsgemisches verwenden.
Je nach den Verfahrensbedingungen werden die neuen Verbindungen als freie Basen oder in Form ihrer Salze gewonnen. Als Salze kommen insbesondere in Frage diejenigen von therapeutisch verwendbaren Säuren, wie anorganischen Säuren, z. B. Halogenwasserstoffsäuren, beispielsweise Salzsäure oder Bromwasserstoffsäure, Perchlorsäure, Salpetersäure oder Thiocyansäure, Schwefel- oder Thiocyansäure, Schwefel- oder Phosphorsäuren, oder organischer Säuren, wie Ameisensäure, Essigsäure, Propionsäure, Glykolsäure, Milchsäure, Brenztraubensäure, Oxalsäure, Malonsäure, Bernsteinsäure, Maleinsäure, Fumarsäure, Aepfelsäure, Weinsäure, Zitronensäure, Ascorbinsäure, Hydroxymaleinsäure, Dihydroxymal einsäure, Benzoesäure, Phenylessigsäure, 4-Aminobenzoesäure, 4-Hydroxy-benzoesäure, Anthranilrsäure, Zimtsäure, Mandelsäure, Salicylsäure,
4-Aminosalicylsäure, 2-Phenoxy-benzoesäure, 2-Acetoxy-benzoesäure, Embonsäure, Methansulfonsäure, Aethansul- fonsäure, Hydroxy-äthansulfonsäure, Benzolsulfonsäure, p-Chlorbenzolsulfonsäure, p-Toluolsulfonsäure, Naphthalinsulfonsäure oder Sulfamylsäuren oder Methionin, Tryptophan, Lysin oder Arginin.
Erhaltene Salze lassen sich in üblicher Weise in die freien Basen, freie Basen in ihre Salze, z. B. die oben genannten, verwandeln.
Die neuen Verbindungen können als Heilmittel, z. B. in Form pharmazeutischer Präparate Verwendung finden, welche sie oder ihre Salze in Mischung mit einem für die enterale, parenterale oder topicale Applikation geeigneten pharmazeutischen organischen oder anorganischen, festen oder flüssigen Trägermaterial enthalten.
Im folgenden Beispiel sind die Temperaturen in Celsiusgraden angegeben.
Beispiel
17,7 g p-Dimethylaminoacetophenon-sydrazon, gelöst in 250 cm3 abs. Alkohol werden mit einer Lösung von 4,4 g Cyanamid in 50 cm3 abs. Alkohol unter Rückfluss 6 Stunden gekocht. Die Lösung wird durch Zugabe von ca. 50 cm3 alkoholischer 2-n. Salzsäure schwach sauer gestellt und unter vermindertem Druck verdampft. Dabei wird ein Kristallisat erhalten, das aus 300 cm3 Isopropanol unter Zusatz von
10 cm3 Wasser umknstallisiert wird, indem die filtrierte Lösung sorgfältig bis zur beginnenden Kristallisation eingeengt wird. Das erhaltene p-Dimethylaminoacetophenon-guanylhydrazon-hydrochlorid der Formel
EMI2.2
schmilzt bei 238-2400.
In analoger Weise kann man das m-Dimethylami- noacetophenon-guanylhydrazon-hydrochlorid, F. 1961980 erhalten.
Process for the preparation of new hydrazones The invention relates to a process for the preparation of guanylhydrazones of the formula
EMI1.1
where R is hydrogen or methyl and Ph is a phenylene radical, or their salts.
In the new compounds, the phenylene radical Ph can be unsubstituted or substituted, e.g. B. by lower alkyl radicals such as methyl, ethyl, or i-propyl, straight or branched butyl, pentyl or hexyl radicals connected in any position, lower alkoxy radicals such as methoxy, ethoxy, propoxy or butoxy radicals, halogen lower alkyl, such as trifluoromethyl, or halogen atoms, such as fluorine, chlorine or bromine atoms.
The new hydrazones and their salts have valuable pharmacological properties. So they show z. B. an anti-inflammatory effect. They can therefore be used as remedies in human or veterinary medicine in inflammatory processes. But they are also valuable as intermediate products in the manufacture of medicines.
Particularly noteworthy are the compounds of the formula
EMI1.2
or the formula
EMI1.3
wherein R denotes methyl or hydrogen, and their salts and in particular p-dimethylamino-acetophenone-guanylhydrazone and its salts.
The process according to the invention for preparing the new compounds is characterized in that a compound of the formula
EMI2.1
wherein Ph and R have the meanings given or a salt thereof with an etherified isourea or isothiourea, e.g. B. an S-alkyl-isothiourea or an O-alkyl-isourea, or cyanamide or a l-guanylpyrazole or a salt of these compounds, preferably a salt with a mineral acid, such as a hydrohalic acid.
The reaction mentioned can be carried out in a customary manner.
The starting materials are known or can be produced by methods known per se.
For the process mentioned, the starting materials can also be used in the form of a reaction mixture formed under the reaction conditions.
Depending on the process conditions, the new compounds are obtained as free bases or in the form of their salts. Particularly suitable salts are those of therapeutically useful acids, such as inorganic acids, e.g. B. hydrohalic acids, for example hydrochloric acid or hydrobromic acid, perchloric acid, nitric acid or thiocyanic acid, sulfuric or thiocyanic acid, sulfuric or phosphoric acids, or organic acids such as formic acid, acetic acid, propionic acid, glycolic acid, lactic acid, pyruvic acid, maleic acid, malonic acid, succinic acid Fumaric acid, malic acid, tartaric acid, citric acid, ascorbic acid, hydroxymaleic acid, dihydroxymalic acid, benzoic acid, phenylacetic acid, 4-aminobenzoic acid, 4-hydroxy-benzoic acid, anthranilic acid, cinnamic acid, mandelic acid, salicylic acid,
4-aminosalicylic acid, 2-phenoxy-benzoic acid, 2-acetoxy-benzoic acid, emboxylic acid, methanesulphonic acid, ethanesulphonic acid, hydroxyethanesulphonic acid, benzenesulphonic acid, p-chlorobenzenesulphonic acid, p-toluenesulphonic acid, naphthalenesulphonic acid, laphthalenesulphonic acid or sulfionamylic acids, or tryptylsulphonic acid, naphthalenesulphonic acid or tryptylic acids.
Salts obtained can be converted into the free bases in the usual way, and free bases into their salts, eg. B. the above, transform.
The new compounds can be used as remedies, e.g. B. can be used in the form of pharmaceutical preparations which contain them or their salts in a mixture with a pharmaceutical organic or inorganic, solid or liquid carrier material suitable for enteral, parenteral or topical application.
In the following example the temperatures are given in degrees Celsius.
example
17.7 g of p-dimethylaminoacetophenone sydrazone, dissolved in 250 cm3 of abs. Alcohol with a solution of 4.4 g of cyanamide in 50 cm3 of abs. Alcohol boiled under reflux for 6 hours. The solution is made by adding approx. 50 cm3 of alcoholic 2-n. Hydrochloric acid made weakly acidic and evaporated under reduced pressure. This gives a crystallizate which is made from 300 cm3 of isopropanol with the addition of
10 cm3 of water is converted by carefully concentrating the filtered solution until crystallization begins. The resulting p-dimethylaminoacetophenone guanylhydrazone hydrochloride of the formula
EMI2.2
melts at 238-2400.
The m-dimethylaminoacetophenone guanylhydrazone hydrochloride, F. 1961980, can be obtained in an analogous manner.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1488864A CH396884A (en) | 1961-01-16 | 1961-01-16 | Process for making new hydrazones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1488864A CH396884A (en) | 1961-01-16 | 1961-01-16 | Process for making new hydrazones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH396884A true CH396884A (en) | 1965-08-15 |
Family
ID=4404584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1488864A CH396884A (en) | 1961-01-16 | 1961-01-16 | Process for making new hydrazones |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH396884A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2642023A1 (en) | 1976-09-18 | 1978-03-23 | Sueddeutsche Kalkstickstoff | PROCESS FOR STABILIZATION OF Aqueous CYANAMIDE SOLUTIONS |
-
1961
- 1961-01-16 CH CH1488864A patent/CH396884A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2642023A1 (en) | 1976-09-18 | 1978-03-23 | Sueddeutsche Kalkstickstoff | PROCESS FOR STABILIZATION OF Aqueous CYANAMIDE SOLUTIONS |
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