CS271547B1 - 2-isopentylthio-6-salicylidenaminobenzothiazole and method of its preparation - Google Patents
2-isopentylthio-6-salicylidenaminobenzothiazole and method of its preparation Download PDFInfo
- Publication number
- CS271547B1 CS271547B1 CS89141A CS14189A CS271547B1 CS 271547 B1 CS271547 B1 CS 271547B1 CS 89141 A CS89141 A CS 89141A CS 14189 A CS14189 A CS 14189A CS 271547 B1 CS271547 B1 CS 271547B1
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- CS
- Czechoslovakia
- Prior art keywords
- compound
- preparation
- salicylidenaminobenzothiazole
- isopentylthio
- ethanol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- BKAWCAIXBHZLGV-UHFFFAOYSA-N 2-[[2-(3-methylbutylsulfanyl)-1,3-benzothiazol-6-yl]iminomethyl]phenol Chemical compound C(CC(C)C)SC=1SC2=C(N1)C=CC(=C2)N=CC=2C(O)=CC=CC2 BKAWCAIXBHZLGV-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims abstract description 8
- PDHNRCYRHHKKOJ-UHFFFAOYSA-N 2-(3-methylbutylsulfanyl)-1,3-benzothiazol-6-amine Chemical compound C1=C(N)C=C2SC(SCCC(C)C)=NC2=C1 PDHNRCYRHHKKOJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- -1 1- 2-Isopentylthio-6-salicylidenaminobenzothiazole Chemical compound 0.000 claims 1
- 241001464384 Hymenolepis nana Species 0.000 abstract description 6
- 108010034145 Helminth Proteins Proteins 0.000 abstract description 4
- 244000000013 helminth Species 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 description 3
- 230000009545 invasion Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 description 2
- 229960001920 niclosamide Drugs 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- 241000242722 Cestoda Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Predmetom vynálezu je 2-izopentyltio-6-salicylidénaminobenzotiazol a sposob Jeho přípravy.The present invention provides 2-isopentylthio-6-salicylidenaminobenzothiazole and a process for its preparation.
Doteraz známe 2-alkyltio-6-salicylidénaminobenzotiazoly (Sidoová# E· a Foltínová P., Chem· Zvěsti 34, 278 /1980/) prejavili fungietatickú účinnost.Hitherto known 2-alkylthio-6-salicylidenaminobenzothiazoles (Sido # E · and Foltin P., Chem · News 34, 278 (1980)) have shown fungietathic activity.
Teraz sme zistili, že doteraz neznáma zlúčenina vzorca >We have now found that the hitherto unknown compound of formula>
Je antihelninticky účinná proti modelovému helmintu Hymenolepis nana.ЙIt is antihelninticky effective against model helminth Hymenolepis nana.Й
Súčasne bol zistený sposob přípravy uvedenaj zlúčeniny na báze 6-amino-2-izopentyl-у tiobenzotiazolu, ktorý sa vyznačuje tým# že 6-amino-2-izopentyltíobenzotiazol sa necháί reagovat s ekvivalentným množstvom salicylaldehydu v etanole za varu po dobu 1 až 30 minút.ýAt the same time, a process for the preparation of said 6-amino-2-isopentyl-6-thiobenzothiazole compound characterized in that 6-amino-2-isopentylthiobenzothiazole is reacted with an equivalent amount of salicylaldehyde in ethanol is boiled for 1 to 30 minutes. .Y
Na a ledu júce příklady bližéie osvetlujú# ale nijako neobmedzujú přípravu# a vlastnosti zlúčeniny podlá vynálezu·| příklad i;The following examples illustrate but do not limit the preparation and properties of the compound of the invention. example i;
Příprava 2-izopentyltio-6-salicylidénaminobenzotiazolu>Preparation of 2-isopentylthio-6-salicylidenaminobenzothiazole
Surový 6-amino-2-izopentyltiobenzotiazol (5,05 g, o,02 mol), získaný podlá Sidoovej;Crude 6-amino-2-isopentylthiobenzothiazole (5.05 g, 0.02 mol), obtained according to Sido;
E· a odlerovej Ž· (Čs. АО 189212 /1978/) v podobě oleja sa rozpustil v etanole (30 cm3)·E · a odlerová Ž · (Čs. АО 189212/1978 /) in the form of oil dissolved in ethanol (30 cm 3 ) ·
К roztoku sa přidal salicylaldehyd (2,45 g# 0,02 mol) a reakčná zmes sa zahriala na 2 minúty do varu· Po přidaní dalfte) dávky etanolu (70 cm3) sa zmes odfarbila aktívnym uhlím·уК solution, salicylaldehyde (2.45 g # 0.02 mole) and the reaction was heated for 2 minutes at boiling after the addition dalfte ·) dose of ethanol (70 cm 3), the mixture was decolorized with activated carbon · у
Z filtrátu vypadnutý olejový produkt odstavením pri 5 °c cez noc stuhol na kryétalickú látku o t«t· 63 až 65 °C, ktorá nevyžadovala daláie Čistenie. výtažok činil 4,8 g, (67#6 %)·1The precipitated oil product solidified at room temperature overnight at 5 ° C to a crystalline solid of 63 ° -65 ° C, which did not require further purification. the yield was 4.8 g, (67 # 6%) · 1
Pre C19H20N2OS2ΪFor C 19 H 20 N 2 OS 2 Ϊ
Příklad 2Example 2
Antihelmintická účinnost zlúčeniny podle vynálezu proti modelovému helmintu Hymenolepis nana var· fraterna (Stiles, 1908)·Anthelmintic activity of the compound of the invention against the model helminth Hymenolepis nana var · fraterna (Stiles, 1908) ·
Antihelmintická účinnost bola stanovená no myáiach-samcoch kmeňa NMRI o žívej hmotnosti 12 až 15 g· Počet mySí v skupině tvořil vždy 6 kusov· 2 skupiny bolí kontrolně invadované# neliečené, Jedna skupina liečená dtandardným preparátor (piperazínová sol niklosamidu) a daláej skupině bola aplikovaná zlúčenina podlá vynálezu· Invázia sa vykonávala átandardným množstvom zrelých vajíčok Hymenolepis nana sondou per os· Zlúčenina podlá vynálezu sa aplikovala na 17· a 18· den po invázii vajíčok# rozpuštěná v Dorfmanovom činidle v dávke 150 mg kg*1 žívej hmoty· Myéiam v kontrolných neliečených skupinách sa zhodným spdsobom podalo Dorfmanovo činidlo· Po hladovke na 20· den po invázii vajíčok# bol pokus ukončený na 21«den zabitím myší a helmintologickou pitvou tenkého čreva· Počítali sa celé pásomnice (Hymenolepis nana) s hlavičkou·Anthelmintic efficacy was determined in male-male NMRI strains of 12-15 g body weight. · The number of mice per group consisted of 6 pieces · 2 groups were invasively controlled # untreated, One group treated with a standard preparator (piperazine salt of niclosamide) and another group was administered Compound of the Invention Invasion was performed with a standard amount of mature Hymenolepis nana probes per os. The compound of the invention was applied 17 and 18 days after the invasion of eggs # dissolved in Dorfman's reagent at a dose of 150 mg kg * 1 live mass. untreated groups were administered Dorfman's reagent in the same way · After hunger for 20 · day after egg invasion # the experiment was terminated on day 21 by killing mice and dissecting the small intestine helmintologically · Whole tapeworms (Hymenolepis nana) with head were counted ·
Zlúčenina podlá vynálezu prejavila účinnost# ktorá zodpovedá 69,5 % účinnosti piperazínovej soli niklosamidu·The compound of the invention showed an activity of # 69.5% of the piperazine salt of niclosamide.
Významný je fakt, že doteraz neznáma zlúčenina novej átruktúry prejevila účinnost proti modelovému helmintu Hymenolepis nana, ktorá představuje 69,5 účinnosti zavedeného preparátu.Significantly, the hitherto unknown compound of the new structure showed efficacy against the model helminth Hymenolepis nana, which represents 69.5 efficacy of the introduced preparation.
Zlúčeninu podlá vynálezu možno používat ako účinnú zložku antihelmintických prípravkov alebo ako medziprodukt pre dalšie syntézy.The compound of the invention may be used as an active ingredient of anthelmintic preparations or as an intermediate for other syntheses.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS89141A CS271547B1 (en) | 1989-01-09 | 1989-01-09 | 2-isopentylthio-6-salicylidenaminobenzothiazole and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS89141A CS271547B1 (en) | 1989-01-09 | 1989-01-09 | 2-isopentylthio-6-salicylidenaminobenzothiazole and method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS14189A1 CS14189A1 (en) | 1990-02-12 |
| CS271547B1 true CS271547B1 (en) | 1990-10-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS89141A CS271547B1 (en) | 1989-01-09 | 1989-01-09 | 2-isopentylthio-6-salicylidenaminobenzothiazole and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS271547B1 (en) |
-
1989
- 1989-01-09 CS CS89141A patent/CS271547B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS14189A1 (en) | 1990-02-12 |
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