DE1418518C - Hydroquinone sulfonic acid salts and process for their preparation - Google Patents
Hydroquinone sulfonic acid salts and process for their preparationInfo
- Publication number
- DE1418518C DE1418518C DE1418518C DE 1418518 C DE1418518 C DE 1418518C DE 1418518 C DE1418518 C DE 1418518C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- sulfonic acid
- acid salts
- hydroquinone sulfonic
- seconds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 4
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical class OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 206010018987 Haemorrhage Diseases 0.000 description 4
- 230000000740 bleeding Effects 0.000 description 4
- 231100000319 bleeding Toxicity 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000002364 anti-haemorrhagic Effects 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 239000000262 estrogen Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 229940011871 Estrogens Drugs 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 240000007711 Peperomia pellucida Species 0.000 description 1
- 229940030484 SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM ESTROGENS Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000003247 decreasing Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylazanium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 229940046080 endocrine therapy drugs Estrogens Drugs 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002934 lysing Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 231100000730 tolerability Toxicity 0.000 description 1
Description
Die Erfindung betrifft Salze der I Ijdrnehjnonsiilinnsäure der allgemeinen FormelThe invention relates to salts of Ijdrnehjnonsilinic acid the general formula
OHOH
SO., R
OH ln SO., R
OH ln
in der R chis Diäthylammonium- oder das Tiiäthanolammouiumion ist. sowie ein Verfahren /u ihrer I lerstellung. das dadurch gekennzeichnet ist, dall man in an -,ich bekannter Weise p-Benzochinon mit einem Hi- »ullil der allgemeinen Formel RIISO1, in der R die vorstehend angegebene Bedeutung hat. nniset/t.in which R chis is diethylammonium or the Tiiäthanolammouiumion. as well as a process for their creation. which is characterized by the fact that in an -, I known manner p-benzoquinone with a hi »ullil of the general formula RIISO 1 , in which R has the meaning given above. nniset / t.
Is wurde gefunden, dall Verbindungen der angegebenen Art hervorragende antihaemorrhagische Wirksamkeit besitzen, die derjenigen \·μι für den gleichen /weck nach dem Stand der Technik herangezogenen Verbindungen, wie der Gruppe der Östrogene, wesentlich überlegen ist.Is was found all connections of the specified Kind of excellent antihaemorrhagic effectiveness own that of those \ · μι for the same / awaken compounds used according to the state of the art, such as the group of estrogens is superior.
Bei Vcrgleichsversiichen mit bekannten antihaemorr'iagischen Mitteln (.1. I. a purl e. Cheinoiheropia, 3 [1961). S. fi2 bis 80) wurde festgestellt, dall die mutiere lilutungs/eit nach R ο s k a 111 am Kauinchenohr in signifikanter Weise abnimmt, und /war für eine bekannte Östrogenkonibination: lacobsuii. Wot. .1. Surgery. <<) (l'>55). S. 711: Hvdio\\tr\ptamm-Kreatinin-Doppelsulfat: Shoer et al.. J. Charm. c\p. Πι.·ι·.. : ■'! (l'iv·). S. 232 M- 23h; N.itmmisal/ dv, l-Amiuo-4-suHonaplilhalins Lsieve el al. Communication al XII rung. Int.Quinica Industrial. Barcelona, Oktober FM1), um etwa 33"',,: für I Ivdiowtryplamin-Kreatinin - Doppelsulfat und das Nairiunisal/. der 4-•N.niino'.iaphlhalin-l-sulfoniiiure um etwa -K)" „ und für (.las erliiuluiiüsgeiniil.le Diatlivlamnioniums.il/ der llydrochinoiisiilfonsäiire um etwa 47",,.In comparison with known anti-haemorrhagic agents (.1. I. a purl e. Cheinoiheropia, 3 [1961). S. fi2 to 80) it was found that the mutant lysis time according to R ο ska 111 decreases significantly in the cheeky ear, and / was for a known estrogen combination: lacobsuii. Wot. .1. Surgery. <<) (l '> 55). S. 711: Hvdio \\ tr \ ptamm-creatinine double sulfate: Shoer et al .. J. Charm. c \ p. Πι. · Ι · .. : ■ '! (l'iv ·). P. 232 M-23h; N.itmmisal / dv, l-Amiuo-4-suHonaplilhalins Lsieve el al. Communication al XII tion. Int.Quinica Industrial. Barcelona, October FM 1 ), at about 33 "',,: for I Ivdiowtryplamin-creatinine - double sulfate and the nairiunisal /. Der 4- • N.niino'.iaphlhalin-l-sulfoniiiure at about -K)""and for (.las erliiuluiiüsgeiniil.le Diatlivlamnioniums.il/ der llydrochinoiisiilfonsäiire by about 47 ",,.
Int folgenden werden die biologischen Eigenschaften der crlindiingsgemäßen Verbindungen mitgeteill:Int the following are the biological properties of the connections according to the principle:
Die To\i/ität Dl.,,,, bestimmt durch intravenöse Injektion an Mausen, beträgt 725 mg kg.The to \ i / ität Dl. ,,,, determined by intravenous Injection to mice, is 725 mg kg.
Die antihäniorrhagische Wirksamkeit bestimmt nach der Methode von Roskam am Kanincheuohr. ergibt folgende Resultate:The anti-hemorrhagic effectiveness is determined the method of Roskam on the rabbit ear. results the following results:
Mittlere Zeit der normalen Blutung
(100 Versiit he) 300 SekundenMean time of normal bleeding
(100 Versiit he) 300 seconds
Miltlere /ei! der Blutung nach intravenöser Verabreichung von 5 111 si des
Produktes pm kg (icwicht tie-, Kaninchens,
I Stunde nach der Injektion gemessen (,I|M) Versuche) 175 SekundenMiltlere / egg! of bleeding after intravenous administration of 5 111 si des
Product pm kg (weight weight, rabbit, measured 1 hour after injection (, I | M) attempts) 175 seconds
Mittlere Zeit der Blutung, unter gleichen
Bedingungen, jedoch fi Stunden nachMean time of bleeding, among same
Conditions, however, fi hours later
der Injektion gemessen 23 1 Sekundenthe injection measured 23 1 seconds
Die mittlere Koagulations/cit, bestimmt nach der bekannten Methode im geeichten lliimolysiemthr, ist I Stunde nach der Injektion von 5 mg des Produktes fio pro kg Tiergewicht auf etwa (lic Hälfte herabgesetzt.The mean coagulation / cit, determined according to the known method in the calibrated lliimolysiemthr, is I hour after the injection of 5 mg of the product fio per kg animal weight reduced to about (lic half.
In klinischen Versuchen an Menschen wurden in Bezug auf lokale und allgemeine Verträglichkeit so.vvohl bei intravenöser wie intramuskulärer Applikation ebenfalls sehr günstige Resultate erhalten.In human clinical trials, local and general tolerability were recommended also obtained very favorable results with intravenous and intramuscular administration.
Die klinische Wirksamkeit wurde durch Besting mint» der Dlutungs- und Koagulations/eil untersucht.The clinical effectiveness was examined by determining the flow and coagulation speed.
Die Messungen wurden eine Stunde nach der Injektion von 2 ecm einer Losung vorgenommen, welche K)",, reines Produkt enthielt. Uutcrdicscu Bedingungen sank bei 20 Patienten die gemessene Blulungs/eii von 2 Minuten. 4S Sekunden auf 2 Minuten. 3 Sekunden, was einer mittleren Verminderung '.on 2d.7"„ entspricht. Die mittleren Koagulation ilen sanken von 4 Minuten. 51 Sekunden auf 3 Mini .en. .V) Sekunden, was einer Verminderung um 30",,, entspricht.The measurements were made one hour after the injection of 2 ecm of a solution, which K) ",, contained pure product. Uutcrdicscu conditions fell in 20 patients the measured bleeding / eii of 2 minutes. 4S seconds to 2 minutes. 3 seconds, which corresponds to a mean reduction '.on 2d.7 "". The mean coagulation ils decreased by 4 minutes. 51 seconds on 3 mini. .V) seconds, which corresponds to a reduction of 30 ",,,.
Im folgenden werden Beispiele des erlindungsgemälJjn Verfahrens /ur Herstellung einiger Vertreter der neuc-i Derivate gegeben.In the following, examples of the invention Process / ur production of some representatives of the neuc-i derivatives given.
I. Diäthylammoniunisal/ der I lulrochinou-,ulfniisäure I. Diethylammoniunisal / I lulroquinou-, sulphonic acid
/u einer alkoholischen Lösung Vi-.n H)Su reinem p-Ben/ochinon werden Ifvig i )iälli\lammoiiiumhisiiHii unter Rühren bei einer Tempjr.iiur ν,ιιι höchsten-. 5 ( zugegeben. Nach der Reaklion v.iid der Alknhul im Vakuum abgedampft und das erhaltene Produkt aus SO" „igem Alkohol umkrisiallMcri./ u an alcoholic solution Vi-.n H) Su pure p-Ben / ochinon become Ifvig i) iälli \ lammoiiiumhisiiHii with stirring at a Tempjr.iiur ν, ιιι maximum. 5 ( admitted. After the Reaklion v.iid der Alknhul im Evaporated in vacuo and the product obtained from SO "" alcohol is crystallized.
Ausbeute: l')S g Diälhvlammoiiiimisalz der ilydrnchinousulfonsiiure. Yield: 1 ½ g of dihydric ammonium sulfonic acid.
Schmelzpunkt: 125 C.Melting point: 125 C.
2. Triäthanolammoniimisal/ der I Ivdrnehinonsulfoiisäure. 2. Triäthanolammoniimisal / der Ivdrnehinonsulfoiisäure.
/u einer Lösung von KlXg p-Ben/ochiiion in Inchloräthylen wird eine Liisuiiü von 23Og Tri.'iihair.'lammoniunibisultil in Mkohi>l uegeben. Die /w: die erfolgt tropfenweise unter Kühlung. Wühlend einer Stunde wird kräftig gerührt, ilieranl And ui-- oi en. Schicht abgetrennt und Ivjili mit η-Bui\ !alkohol behandelt und dann abgekiilill. Bei R.inmtenperatur IViIIt d.is Produkt als eine dicke Flüssigkeit aus. -\usbeuie 1HSg. Diese Verbindung wird verniiilels IR-Spektrum identifiziert, wob.'i die Verbindung in einer Kalii::< <'nromidpastille mit einem Perkiii-I !nur Spektrophotometer Modell 257 aufgenommen und. K '.verden hierbei die folgenden charakteristischen Absorplionsina\ini:i (WeI-lenzahlen in cm ') erhalten :A solution of 23Og tri.'iihair.'lammoniunibisultil in Mkohi> l is given to a solution of KlXg p-ben / ochiiion in inchlorethylene. Die / w: die takes place drop by drop with cooling. For an hour it is stirred vigorously, ilieranl and ui- oi en. Layer separated and Ivjili treated with η-Bui \! Alcohol and then chilled off. At room temperature IViIIt the product as a thick liquid. - \ usbeuie 1 HSg. This compound is identified in the IR spectrum, with the compound in a Kalii :: <<'nromide paste with a Perkiii-I! Only spectrophotometer model 257 and recorded. K '. The following characteristic absorptionsina \ ini: i (wave numbers in cm') are obtained:
11X0 (Sulfogruppe): 33.1^ IaS1OzUeHeS ll)dro\vh. K)HO(C Oll): 2915 und 21M)O(C II): 1515 und 1445 (C C aromatisch): S25 (C II aulV-rhalb der liju/olringebeii'--): 1025 (C N der Nmivogruppe).11X0 (sulfo group): 33.1 ^ IaS 1 OzUeHeS ll) dro \ vh. K) HO (C Oll): 2915 and 2 1 M) O (C II): 1515 and 1445 (CC aromatic): S25 (C II outside the liju / olringebeii '-): 1025 (CN of the Nmivo group) .
Claims (2)
meinen Formel1. Salts tier Hulrocltmonsiill \ <iis: iire of a
my formula
Family
ID=
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