CS242023B1 - Anilide of 3-benzylsalicylic acid - Google Patents

Anilide of 3-benzylsalicylic acid Download PDF

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Publication number
CS242023B1
CS242023B1 CS847796A CS779684A CS242023B1 CS 242023 B1 CS242023 B1 CS 242023B1 CS 847796 A CS847796 A CS 847796A CS 779684 A CS779684 A CS 779684A CS 242023 B1 CS242023 B1 CS 242023B1
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CS
Czechoslovakia
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formula
mmol
anilide
benzylsalicylic
compound
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CS847796A
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Czech (cs)
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CS779684A1 (en
Inventor
Viktor Zikan
Dagmar Nemcova
Jaroslav Danek
Radmila Spaldonova
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Viktor Zikan
Dagmar Nemcova
Jaroslav Danek
Radmila Spaldonova
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Application filed by Viktor Zikan, Dagmar Nemcova, Jaroslav Danek, Radmila Spaldonova filed Critical Viktor Zikan
Priority to CS847796A priority Critical patent/CS242023B1/en
Publication of CS779684A1 publication Critical patent/CS779684A1/en
Publication of CS242023B1 publication Critical patent/CS242023B1/en

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Abstract

Anilid kyseliny 3-benzylsalicylové vzorce I Způsob jeho přípravy spočívá v reakci kyseliny 3-benzylsalicylové s anilinem v xylenu za přítomnosti fosfortrichloridu za zvýšené teploty. Tato nová, dosud nepopsaná látka vykazuje anthelmintickou účinnost proti modelovému helmintu Aspiculuris tetraptera.3-Benzylsalicylic acid anilide AND The method of its preparation lies in the reaction 3-benzylsalicylic acid with aniline v xylene in the presence of phosphorothrichloride elevated temperature. This new, not yet described substance shows anthelmintic activity against model helmint Aspiculuris tetraptera.

Description

(54 J Anilid kyseliny 3-benzylsalicylové(54 J 3-Benzylsalicylic acid anilide

22

Anilid kyseliny 3-benzylsalicylové vzorce I3-Benzylsalicylic anilide of formula I

Způsob jeho přípravy spočívá v reakci kyseliny 3-benzylsalicylové s anilinem v xylenu za přítomnosti fosfortrichloridu za zvýšené teploty.A process for its preparation consists in reacting 3-benzylsalicylic acid with aniline in xylene in the presence of phosphoricrichloride at elevated temperature.

Tato nová, dosud nepopsaná látka vykazuje anthelmintickou účinnost proti modelovému helmintu Aspiculuris tetraptera.This novel, yet undescribed substance exhibits anthelmintic activity against a model helminth of Aspiculuris tetraptera.

Vynález se týká anilidu kyseliny 3-benzylsalicylové vzorce IThe invention relates to a 3-benzylsalicylic acid anilide of the formula I

OHOH

Tato nová, dosud nepopsaná, sloučenina vykazuje použitelnou anthelmintickou účinnost, zejména proti modelovému helmintu Aspiculuris tetraptera.This novel, yet undescribed, compound exhibits useful anthelmintic activity, particularly against the Aspiculuris tetraptera model helminth.

Sloučeninu vzorce I lze podle vynálezu připravit reakcí o sobě známé kyseliny 3-benzylsalicylové (US pat. č. 2 042 343) s anilinem v přítomnosti fosfortrichloridu v prostředí inertního rozpouštědla za zvýšené teploty, výhodně s 0,35 molárním množstvím fosfortrichloridu v xylenu při teplotě 130 až 140 °C.The compound of formula (I) according to the invention can be prepared by reacting the known 3-benzylsalicylic acid (US Pat. No. 2,042,343) with aniline in the presence of phosphfortrichloride in an inert solvent at elevated temperature, preferably with 0.35 molar amount of phosphfortrichloride in xylene at 130-140 ° C.

Hodnocení antheímintické účinnosti proti modelovému helmintu Aspiculuris tetrapteraEvaluation of antheímintic efficacy against Aspiculuris tetraptera model helminth

Pokusy byly provedeny na myších samcích kmene SPF/Velaz s hmotností 18 až 20 gramů ve skupinách po 3 kusech. Myši by-The experiments were performed on male SPF / Velaz mice weighing 18-20 grams in groups of 3 pieces each. Mice were-

Claims (1)

pRedmžtpRedmžt Anilid kyseliny 3-benzylsalicylové vzorce I ly invadovány způsobem per os dávkou 80 až 100 vajíček/myš modelového helmintu Aspiculuris tetraptera a po ukončení vývinu parazita do pohlavní zralosti byla aplikována zkoušená látka vzorce I. Látka byla aplikována per os duodenální sondou v Dorfmanově činidle v dávce 150 mg/kg a 75 mg/kg po dobu 3 dní. Po 7 dnech -od prvé aplikace byl makroskopicky u dekapitovaných myší zjišťován počet červů ve střevě v porovnání s kontrolní skupinou neléčených zvířat a výpočtem podle Stewarda stanovena v průměru 93,3 % anthelmintická účinnost hodnocené látky vzorce I.The 3-benzylsalicylic anilide of formula I was invaded per os with a dose of 80-100 eggs / mouse of Aspiculuris tetraptera model helminth and, after parasite development to sexual maturity, the test compound of formula I was administered per os via duodenal gavage in Dorfman's reagent at a dose. 150 mg / kg and 75 mg / kg for 3 days. After 7 days from the first application, the number of worms in the intestine was determined macroscopically in decapitated mice as compared to a control group of untreated animals and an average of 93.3% anthelmintic activity of the compound of formula I was determined by the Steward calculation. Způsob přípravy látky vzorce I je jednoduchý, bližší podrobnosti vyplývají z následujícího příkladu provedení. Uvedený příklad vynález pouze ilustruje, nikoli omezuje:The method of preparation of the compound of formula (I) is simple; This example illustrates the invention but does not limit: Směs 7,53 g kyseliny 3-benzylsalicylové (33 mmol) a 3,07 g anilinu (33 mmol) a 70 mililitrů xylenu byla zahřáta k varu a k vroucímu roztoku přikapáno 1,58 g fosfortrichloridu (11,5 mmol). Reakční směs byla zahřívána při teplotě 130 až 140 °C po dobu 4 h pod zpětným chladičem a po ochlazení vytrepána 5% vodným roztokem hydrogenuhličitanu sodného. Organická vrstva byla destilací za tlaku 1,5 kPa zbavena rozpouštědla a odparek překrystalován ze směsi chloroformu s hexanem. Bylo získáno 9,1 g (91%) anilidu kyseliny 3-benzylsalicylovéA mixture of 7.53 g of 3-benzylsalicylic acid (33 mmol) and 3.07 g of aniline (33 mmol) and 70 ml of xylene was heated to boiling and 1.58 g of fosfortrichloride (11.5 mmol) was added dropwise to the boiling solution. The reaction mixture was heated at 130-140 ° C for 4 h under reflux and, after cooling, shaken with 5% aqueous sodium bicarbonate. The organic layer was freed from the solvent by distillation at 1.5 kPa and the residue was recrystallized from chloroform-hexane. 9.1 g (91%) of 3-benzylsalicylic acid anilide were obtained
CS847796A 1984-10-12 1984-10-12 Anilide of 3-benzylsalicylic acid CS242023B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CS847796A CS242023B1 (en) 1984-10-12 1984-10-12 Anilide of 3-benzylsalicylic acid

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Application Number Priority Date Filing Date Title
CS847796A CS242023B1 (en) 1984-10-12 1984-10-12 Anilide of 3-benzylsalicylic acid

Publications (2)

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CS779684A1 CS779684A1 (en) 1985-08-15
CS242023B1 true CS242023B1 (en) 1986-04-17

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