CS271297B1 - 1-/bicyclo/2,2,1/hept-5-en-2, 3-dicarboximido/2, 6-diethylbenzene - Google Patents
1-/bicyclo/2,2,1/hept-5-en-2, 3-dicarboximido/2, 6-diethylbenzene Download PDFInfo
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- CS271297B1 CS271297B1 CS891427A CS142789A CS271297B1 CS 271297 B1 CS271297 B1 CS 271297B1 CS 891427 A CS891427 A CS 891427A CS 142789 A CS142789 A CS 142789A CS 271297 B1 CS271297 B1 CS 271297B1
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- Czechoslovakia
- Prior art keywords
- hept
- bicyclo
- diethylbenzene
- dicarboximido
- compound
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 238000009835 boiling Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 claims description 2
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 claims description 2
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 108010034145 Helminth Proteins Proteins 0.000 abstract description 5
- 244000000013 helminth Species 0.000 abstract description 5
- 241001126259 Nippostrongylus brasiliensis Species 0.000 abstract description 3
- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000009545 invasion Effects 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 3
- 230000000507 anthelmentic effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229960001614 levamisole Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- -1 2,6-diethylaniline acid anhydride Chemical class 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Predmetom vynálezu je l-[bicyklo(2.2.l)hept-5-en-2,3-dikarboximido]2,6-dietylbenzén.The present invention provides 1- [bicyclo (2.2.1) hept-5-ene-2,3-dicarboximido] 2,6-diethylbenzene.
Doteraz bolí známe viacerě biologicky aktivně zlúčeniny na báze 2,6-dialkylanilí· nov, z imidov boli známe iba ftálimidy.To date, several biologically active compounds based on 2,6-dialkylanilines have been known, only phthalimides have been known from the imides.
Terez ame zlatili, že doteraz neznáma zlúčenina vzorcaTerez ame golded that a hitherto unknown compound of the formula
C2H5 je antihelminticky účinná proti poměrně odolnému modelovému helmintu Nippoetrongylus braailienaia.C 2 H5 is antihelmintically effective against relatively resistant model helminth Nippoetrongylus braailienaia.
Súčaene bol zlatěný eposob přípravy uvedenej zlúčeniny na báze anhydridu kyaeliny bicyklo(2.2.1)hept-5-en-2,3-dikarboxylovej a 2,6-dietylanilínu, ktorý ea vyznačuje tým, Že ekvivalentně množetvá uvedených dvoch východiakových látok ea apolu nechejú reagovat’ najprv v benzéne za varu a potom v acetanhydride za varu.There was also a golden epoxy of bicyclo (2.2.1) hept-5-ene-2,3-dicarboxylic acid and 2,6-diethylaniline acid anhydride, which is characterized in that equivalent amounts of the two starting materials ea and apol are left to leave The reaction is first carried out in benzene at boiling and then in acetic anhydride at boiling.
Nasledujúce příklady bližšie oevetTujú, ale nijako neobmedzujú přípravu a vlaatnoati zlúčeniny podl’a vynálezu.The following examples illustrate in more detail, but do not limit the preparation and the formulations of the compounds of the invention.
Příklad 1Example 1
Příprava l-[bicyklo(2.2.1)hept-5-en-2,3-dikarboximidoj2,6-dietylbenzénuPreparation of 1- [bicyclo (2.2.1) hept-5-ene-2,3-dicarboximidoyl-2,6-diethylbenzene
2,6-Dietylanilín (14,9 g, 0,1 mol) a anhydrid kyaeliny bicyklo(2.2.1)hept-5-en-2,3-dikarboxylovej (16,4 g, 0,1 mol) ea apolu povarili 10 minut v benzéne (50 cnP). Po ochladení ea z reakčnej zmeai vylúčil kryštalický aurový produkt. К matečnému luhu ea přidala zmes cyklohexánu a petroléteru v pomere 1 : 1 v takom množatve, aby roztok zoatal právě homogénny a zmes aa odatavila к JaTSej kryštalizácii pri 10 °C cez noc. Vypadol JaTší podiel kryštalického produktu, obe kryštalické frakcie ea refluxovali a acetanhydridom (30 cnr) po dobu 30 minút, potom ea reakčná zmee doplnila teplou vodou (60 °C) na 500 cm^ a povarila ea 5 minút. Po ochladení na 5 °C sa tuhý podiel izoloval a prekrystalizoval zo zmeai etanol - voda v pomere 3 : 1 za použitia aktívneho uhlia. Potom ea látka rozpuatila v octane etylovom a opať aa odfarbila aktívným uhlím za varu.2,6-Diethylaniline (14.9 g, 0.1 mol) and bicyclo (2.2.1) hept-5-ene-2,3-dicarboxylic acid anhydride (16.4 g, 0.1 mol) and cooked with apol 10 minutes in benzene (50 cnP). Upon cooling ea, a crystalline auric product precipitated from the reaction mixture. To the mother liquor ea, a 1: 1 mixture of cyclohexane and petroleum ether was added in an amount such that the solution became just homogeneous and the mixture aa melted to crystallize at 10 ° C overnight. More crystalline product was dropped, both crystalline fractions e and refluxed with acetic anhydride (30 cm @ 3) for 30 minutes, then the reaction mixture was made up to 500 cm @ 3 with warm water (60 DEG C.) and boiled for 5 minutes. After cooling to 5 ° C, the solid was isolated and recrystallized from a 3: 1 mixture of ethanol-water using activated carbon. Then, the substance was dissolved in ethyl acetate and again and decolourised with charcoal at boiling.
Příklad 2Example 2
Antihelmintická účinnost* zlúčeniny podlá vynálezu proti modelovému helmintu Nippostrongylua braailien8iaThe anthelmintic activity of a compound of the invention against a model helminth of Nippostrongylua braailien8ia
Antihelmintická účinnost’ bola stanovená na krysách - aamcoch veku 4 až 6 týždňov a váhy 120 až 140 g, Pokuanú skupinu tvořilo vždy 6 krýa. Dve skupiny boli kontrolně,The anthelmintic efficacy was determined on rats of 4-6 weeks of age and weights of 120-140 g, and the test group consisted of 6 rats each. Two groups were control,
CS 271297 Bl invadované, neliečené, jedna skupina liečená štandardným preparátom Levamisol a áaTšej skupině bola aplikovaná zlúčenina podlá vynálezu. Invázia sa vykonávala čerstvými larvami Nippostrongylus brasiliensis III. invázneho štádia v počte 500 lariev na jednu krysu. Prvá aplikácia sa vykonala v 3. den po invázii (4. den pokusu), druhá aplikácia v 6. deň po invázii. VeTkosf dávky bola 2 krát a 150 mg.kg*^· živej hmoty. Aplikácia bola vykonaná bez predchádzajúcej hladovky. Látky boli suspendované v Dorfmanovom činidle a aplikované podlá hmotnosti v objeme 0,65 až 12 cm< Krysám v kontrolných neliečených skupinách bolo zhodným spósobom aplikované per os samotné Dorfmanovo činidlo. Koprologické vyšetrenie trusu bolo vykonané v 6. den po invázii (7. deň pokusu) před druhou aplikáciou testovanej látky alebo Dorímanovho činidla u kontrolných skupin. Poa kus bol ukončený hladovkou na 7. deň po invázii a zabitím krýs na 8. deň po invázii (9, deň pokusu). Účinnosť bola vyhodnotená vykonáním helmintologickej pitvy prvých 2/3 tenkého čreva. Účinnosť liečby bola vyjádřená v percentách metodou nepriamej aktivity ’ podlá Stewarda.CS 271297 B1 invaded, untreated, one group treated with standard Levamisol and the other group received the compound of the invention. The invasion was performed with fresh larvae of Nippostrongylus brasiliensis III. invasive stage of 500 larvae per rat. The first application was performed on day 3 post invasion (day 4 of the experiment), the second application on day 6 post invasion. At the dose the dose was 2 times and 150 mg / kg body weight. The application was performed without a hunger strike. The substances were suspended in Dorfman's reagent and applied by weight in a volume of 0.65 to 12 cm. The rats in the untreated control groups were treated with Dorfman's reagent alone per os in an identical manner. Droppings were performed on day 6 after invasion (day 7 of the experiment) before the second administration of test substance or Doriman reagent in control groups. Poa piece was fasted on day 7 after invasion and killing rats on day 8 after invasion (day 9 of the experiment). Efficacy was evaluated by performing a helminthologic autopsy on the first 2/3 of the small intestine. Treatment efficacy was expressed as a percentage of indirect activity, according to Steward.
Zlúčenina podlá vynálezu projevila účinnost, ktorá zodpovedá 49,7 % účinnosti standardu (Levamisol),The compound of the invention showed an activity equivalent to 49.7% of that of the standard (Levamisol),
Významný je fakt, že doteraz neznáma zlúčenina novej štruktúry prejavila účinnosť proti modelovému helmintu Nippostrongylus brasiliensis, ktorá představuje 49,7 % Štandardného preparátu levamisol (u uvedeného modelového helmintu se považuje za pozoruhodná účinnosť nad 20 %).Significantly, the hitherto unknown compound of the new structure showed efficacy against the model helminth of Nippostrongylus brasiliensis, which represents 49.7% of the standard levamisole preparation (said model helminth is considered to be remarkable for efficacy above 20%).
Zlúčeninu podlá vynálezu možno pouŽívať ako účinnú zložku antihelmintických prípravkov, alebo ako medziprodukt pre číalšie syntézy.The compound of the invention may be used as an active ingredient of anthelmintic preparations, or as an intermediate for further syntheses.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS891427A CS271297B1 (en) | 1989-03-07 | 1989-03-07 | 1-/bicyclo/2,2,1/hept-5-en-2, 3-dicarboximido/2, 6-diethylbenzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS891427A CS271297B1 (en) | 1989-03-07 | 1989-03-07 | 1-/bicyclo/2,2,1/hept-5-en-2, 3-dicarboximido/2, 6-diethylbenzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS142789A1 CS142789A1 (en) | 1989-12-13 |
| CS271297B1 true CS271297B1 (en) | 1990-09-12 |
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ID=5348623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS891427A CS271297B1 (en) | 1989-03-07 | 1989-03-07 | 1-/bicyclo/2,2,1/hept-5-en-2, 3-dicarboximido/2, 6-diethylbenzene |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS271297B1 (en) |
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1989
- 1989-03-07 CS CS891427A patent/CS271297B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS142789A1 (en) | 1989-12-13 |
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