PL89670B1 - - Google Patents

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PL89670B1
PL89670B1 PL1971148770A PL14877071A PL89670B1 PL 89670 B1 PL89670 B1 PL 89670B1 PL 1971148770 A PL1971148770 A PL 1971148770A PL 14877071 A PL14877071 A PL 14877071A PL 89670 B1 PL89670 B1 PL 89670B1
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
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    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
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    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Description

Przedmiotem wynalazku jest sposób wytwarzania nowych aminofenyloamidyn, nadajacych sie do zwalcza¬ nia pasozytów, zwlaszcza robaków.Z opisu patentowego St.Zjedn.Am. nr 3184482 znane sa zwiazki przedstawione na rysunku wzorem ogól¬ nym 2, w którym R oznacza fenyl, ewentualnie podstawiony miedzy innymi grupa alkiloaminowa, acyloamino- wa, alkiloaminokarboksylowa, zas R1 i R2 = H albo alkil. W cytowanym opisie patentowym wymienione sa znane acyloaminofenyloformaniidyny, takie jak N-/p-acetamidofenylo/-hW-dwumetyloformamidyna i N-fenylo- acetamidyny jak N-/p-chlorofenylo/-hTNMwumetyloacetamidyny. Zwiazki te jednak nie sa aktywne przeciwko nizej wymienionym robakom.Stwierdzono, ze do zwalczania pasozytów, zwlaszcza robaków, wybitnie nadaja sie nowe aminofenyloami- dyny o wzorze 1, w którym R oznacza grupe alkilowa o 1-3 atomach wegla, R1 oznacza atom wodoru, R2 oznacza grupe o wzorze -COR6 lub grupe o wzorze -S02R7, w których to wzorach R? oznacza atom wodoru, grupe alkilowa o 1-10 atomach wegla, ewentualnie podstawiona chlorowcem, grupa CF3 lub alkoksylowa o 1-3 atomach wegla, albo R6 oznacza grupe cykloalkilowa o 3-6 atomach wegla, grupe alkenylowa o 2-5 atomach wegla, albo oznacza grupe alkoksylowa o 1-8 atomach wegla, ewentualnie podstawiona grupa alkoksylowa o 1-3 atomach wegla lub R6 oznacza grupe fenylowa, ewentualnie podstawiona chlorem i/lub grupa acetyloksy- lowa, ponadto oznacza grupe furylowa lub metyloizoksazolilowa, a R7 oznacza grupe alkilowa o 1-3 atomach wegla, R3 oznacza atom wodoru lub chloru, R4 oznacza grupe alkilowa o 1-3 atomach wegla, lub alkoksylowa o 1-3 atomach wegla, Rs oznacza grupe alkilowa o 1-3 atomach wegla, a R8 i R9 oznaczaja atomy wodoru oraz ich sole.Sposobem wedlug wynalazku nowe aminofenyloamidyny o wzorze 1, w którym wszystkie symbole maja wyzej podane znaczenie, otrzymuje sie w ten sposób, ze pochodne aniliny o ogólnym wzorze 3, w którym R1, R2, R3, Rs i R9 posiadaja wyzej wymienione znaczenie, poddaje sie reakcji z amidami, kwasów karboksylowych o ogólnym wzorze 4, w którym W oznacza atom tlenu lub siarki, a R, R4 i R5 posiadaja wyzej wymienione znaczenie, albo z ich solami* albo z ich reaktywnymi pochodnymi, ewentualnie w obenosci srodków kondensuja-" 89670 cych i ewentualnie w obecnosci obojetnych rozpuszczalników, a produkty reakcji wyodrebnia sie pod postacia soli lub zasad i ewentualnie przeprowadza sie nastepnie w znany sposób w inne dowolne sole.Jako reaktywne pochodne amidowe stosuje sie na przyklad zwiazki otrzymywane przez reakcje amidów lub tioamidów o ogólnym wzorze 4 z kwasami nieorganicznymi, takimi jak kwas chlorowodorowy, trójchlorek boru, kwas siarkowy albo z nieorganicznymi lub organicznymi halogenkami kwasów, jak na przyklad z tleno¬ chlorkiem fosforu, pieciochlorkiem fosforu, fosgenem, chlorkiem tionylu, bromkiem benzoilu, p-tolucnosulfo- chlorkiem lub z mieszanina fosgen/chlorek glinowy, fosgen/chlorowodór, lub fosgen/tlenochlorek fosforu albo z fluoroboranami trójalkilooksaniowymi, w których grupy alkilowe zawieraja 1-5 atomów wegla albo z siarcza¬ nami dwualkilowymi, w których grupy alkilowe zawieraja 1-5 atomów wegla, albo z halogenkami alkilowymi, zawierajacymi 1-5 atomów wegla.Reaktywnymi pochodnymi amidowymi sa takze acetale i tioacetale o ogólnym wzorze 4a, w którym W, P, R4 i R5 posiadaja wyzej wymienione znaczenie, a grupy alkilowe zawieraja 1-4 atomów wegla.Jako srodki kondensujace stosuje sie na przyklad kwasy nieorganiczne, jak na przyklad kwas chlorowodo¬ rowy, trójchlorek boru, kwas siarkowy, albo nieorganiczne lub organiczne halogenki kwasowe, jak na przyklad tlenochlorek fosforu, pieciochlorek fosforu, fosgen, chlorek tionylu, bromek benzoilu, p-toluenosulfochlorek lub mieszanina fosgen/chlorek glinowy lub fosgen/chlorowodór lub fosgen/tlenochlorek fosforu albo fluoroborany, trójalkilooksonionojve zawierajace 1-5 atomówwegla w grupach alkilowych albo w siarczany dwualkilowe, zawie¬ rajacymi 1-5 atomów wegla w grupach alkilowych albo z halogenkami alkilowe zawierajace 1—5 atomów wegla.W przypadku' reakcji tioamidów o ogólnym wzorze 4, w którym W oznacza atom siarki, korzystne moze byc stosowanie dodatkowo do tych srodków kondensujacych, albo bez nich, srodków odsiarczajacych, jak na przyklad HgC, Ag2 O lub Hg/CN/2.Korzystne jest wprowadzanie reagentów w ilosciach stechiometrycznych.Jako rozpuszczalniki moga znalezc zastosowanie wszystkie obojetne rozpuszczalniki organiczne, jak aroma¬ tyczne, ewentualnie chlorowcowane, weglowodory, jak na przyklad benzen, toluen, dwuchlorobenzen, ewentual¬ nie chlorowane, alifatyczne weglowodory, jak na przyklad chlorek metylenu i chloroform lub czterometylenosul- fon, lub takze nizsze alifatyczne alkohole, jak na przyklad metanol i etanol.Reagenty miesza sie razem korzystnie w temperaturze pokojowej, okolo — 20°C i ewentualnie w celu doprowadzenia reakcji do konca ogrzewa sie je do temperatury okolo 30°-l50°C, kotrzystnie 70°-120°C.Kolejnosc dodawania do siebie reagentów jest dla wyniku reakcji bez znaczenia.Zwiazki otrzymywane sposobem wedlug wynalazku posiadaja charakter zasadowy. Moga byc stosowane jako wolne zasady lub pod postacia ich soli, na przyklad chlorowcowodorków, korzystnie chlorowodorków, siarczanów, fosforanów, azotanów, octanów lub naftalenosulfonianów.Szczególnie korzystne wlasciwosci posiadaja zwiazki o ogólnym wzorze 1, w którym R oznacza korzystnie grupe alkilowa, zawierajaca 1 lub 2 atomy wegla, R1 oznacza atom wodoru, R2 oznacza grupe o wzorze -COR6 lub grupe o wzorze S02 R7, przy czym R6 oznacza korzystnie atom wodoru, grupe alkilowa o prostym lub rozgalezionym lancuchu, zawierajaca 1 do 3 atomów wegla ewentualnie podstawiona grupa trójfiuoromel) Iowa lub grupa metoksylowa, albo grupe cykloalkilowa, zawierajaca 3 lub 5 atomów wegla, albo grupe furylowa, albo 3-metyloizoksazolilowa lub grupe fenylowa albo grupe alkoksylowa zawierajaca 1-4 atomów wegla, ewentualnie podstawiona grupa metoksylowa, a R7 oznacza korzystnie grupe alkilowa zawierajaca 1 lub 2 atomy wegla, R3 oznacza korzystnie atom wodoru, R8 oznacza atom wodoru, R5 oznacza grupe alkilowa, zawierajaca 1 lub 2 atomy wegla, a R4 oznacza grupe alkilowa, zawierajaca 1 lub 2 atomy wegla, albo grupe metoksylowa, oiaz ich sole z fizjologicznie dopuszczalnymi kwasami. Korzystnymi solami nowych zwiazków sa chlorowodorki.Sposób wedlug wynalazku jest blizej wyjasniony w nastepujacych przykladach. Wszystkie temperatury podano w stopniach Celsjusza.Jak juz wspomniano, nowe zwiazki nadaja sie wybitnie do zwalszania pasozytów, zwlaszcza robaków.Nalezy uwazac za wyjatkowo niespodziewane i nie dajace sie przewidziec, ze wprowadzenie grupy acyloamino* wej lub sulfonyloaminowej do pierscienia fenylowego N-fenyloacetamidyn spowoduje wystapienie wysokiej ak¬ tywnosci przeciw robakom. Nastepnie okazalo sie, ze zwiazki te w sposób istotny dzialaja lepiej, niz inne znane srodki przeciw robakom o tym samym kierunku dzialania, jak na przyklad zwiazek hydroksynaftoesan befe- nium, fenylonodwuizotiocyjanian/1,4/, perchloroetylen, tiabendazole i parbendazole. Szczególnie nalezy pod- kreslic, ze przy jednorazowym podaniu uzyskiwano bardzo dobre wyniki.Zwiazki otrzymane sposobem wedlug wynalazku wykazuja niespodziewanie dobre dzialanie o szerokim zakresie przeciwko nastepujacym robakom nicieniom i tasiemcom.89670 3 l. Nicienie. 1. Ancylostoma caninum, Uncinaria stenocephala i Bundostomum trigonocephalum z rodziny Ancyloastomati- dae; 2.%Haemonehus contortus, Trichostrongylus colubriformis, Cooparia punctata, Ostertagie circumcinata, Nippo- strongylus muris i Nematospircides dubius z rodziny Trichostrongylidae; 3. Ossephagostonum columbianum i Chabertiaovina z rodziny Strongylidae; 4. Strongyloides ratti z rodziny Rhabditidae; . Txocars canis, Toxascarislaonina i larwy Ascaria suum z rodziny Ascarididae; 6. Aspiculuris tetraptera z rodziny Cbcyuridae; 7. Heterskie spumosa z rodziny Heterakidae.U. "Bsiemce. 1. Hymenolepis nana i Hymenolepis mierostoma z nadrodziny Taenicidea.Skutecznosc zbadano za pomoca prób na zwierzetach zakazonych pasozytami stosujac podawanie doustne i pozajelitowe. Zwierzeta poddawane badaniom bardzo dobrze znosily stosowane dawki. Nawet przy podawaniu dawek 10 razy do 100 razy wiekszych niz terapeutycznie potrzebne, zwierzeta doswiadczalne przezyly leczenie.Przyklad I. Zwiazek o wzorze 5.Do 4-karboetoksyaminoniliny i 46,6 g N,N-dwumetyloacetamidu rozpuszczonych w 1000 ml toluenu wkra- pla sie w temperaturze 20° 79,5 g tlenochlorku fosforu, miesza w ciagu 90 minut w temperaturze 20°C i nastep¬ nie ogrzewa do wrzenia pod chlodnica zwrotna wciagu 4 godzin. Po zdekantowaniu toluenu przenosi sie pozostalosc do mieszaniny wody i chloroformu, dodaje chlodzac lugu sodowego, odsacza produkty nieorganicz¬ ne i oddziela faze organiczna. Po odparowaniu fazy organicznej otrzymuje sie 101 g surowej N-/4-karboetoksy- aminofenyloZ-N^-dwumetyloacetamidyny, która rozpuszcza sie w octanie etylowym i ponownie wytraca. Tem¬ peratura topnienia 130-131°C, wydajnosc 84 g. Przez rozpuszczenie w eterze etylowym i dodanie eterowego roztworu kwasu solnego otrzymuje sie chlorowodorek, który rozpuszcza sie w mieszaninie octanu etylowego i alkoholu i ponownie wytraca. Temperatura topnienia 222°C (z rozkladem). Ten sam zwiazek otrzymuje sie takze stosujac jako srodek kondensujacy fosgen lub p-toluenosulfochlorek.W analogiczny sposób otrzymuje sie nastepujace zwiazki: N-/4-karbometoksyaminofenylo/-N',N,-dwumetyloacetamidyne o temperaturze topnienia 137—139°, N-/4-karboetoksyaminofenylo/-N,,N,-dwumetylopropionoamidyne o temperaturze topnienia 114-115°, N-/4-karboksyaminofenylo/-N,,N,-dwuetyloacetamidyne o temperaturze topnienia 88-90°, N-/4-karboetoksyaminofenylo/-N*-etylo-N-metyloacetamidyne o temperaturze topnienia 103-107°, ' chlorowodorek o temperaturze topnienia 195—196°, Przyklad II. Zwiazek o wzorze 6.Wedlug metody opisanej w przykladzie I przez reakcje 4-aminoacetamilidu i dwuetyloacetamidu w obec¬ nosci tlenochlorku fosforowego jako srodka kondensujacego otrzymuje sie N-/4-acetyloaminofenylo/-Nv,N'-dwu- metyloacetamidyne o temperaturze topnienia 132—134°, wydajnosc 93% wartosci teoretycznej, temperatura topnienia chlorowodorku 258-260°.W analogiczny sposób otrzymuje sie nastepujace zwiazki: N-/4-cyklopentylokarbonyloaminofenylo/-N*,^-dwumetyloacetamidyne, chlorowodorek o temperaturze topnienia 244—247°, N-/4-trójfluoroacetyloaminofenylo/-N*.hT-dwumetyloacetamidyne, chlorowodorek o temperaturze topnienia 273—274°.Przyklad III. Zwiazek o wzorze 7.Wedlug metody opisanej w przykladzie I z 90 g 4-karboetoksyamino-3-chloroaniliny, 46,6 g N,N-dwumety- loacetamidu i 79,5 g tlenochlorku fosforowego w 100 ml toluenu otrzymuje sie 37 g N-/4-karboetoksyamino-3- -chlorofenylo/^N-dwumetyloacetamidyny o temperaturze topnienia 73-74°C.W analogiczny sposób otrzymuje sie nastepujace zwiazki o ogólnym wzorze 1, w którym R oznacza metyl, a R1, R8 i R9 oznaczaja atomy wodoru, a symbole R2, R3, R4 i R5 maja znaczenie podane w tablicy: R3' 1 2-a . 2-a 2-C1 R4 CH3 . CH3 CH3 fc5 CH3 CH3 CH3 R2 4-H3C2OOC 4-CH3-CO grupa o wzorze 8 Temperatura topnienia HC1212° 1 (z rozkladem) HQ 172-174° (z rozkladem) Ha 252-253° (z rozkladem)4 89670 Przyklad IV. Roztwór 51,5 g N,N-dwumetylotioacetamidu i 74 g p-aminoacetanilidu w 500 ml eta¬ nolu miesza sie energicznie z dodatkiem 185 g tlenku rteci wciagu 8 godzin w temperaturze 0°, a nastepnie wciagu 15 godzin w temperaturze 80°. Osad odsacza sie pod próznia, pozostalosc destyluje pod próznia i otrzy¬ muje sie 24,6 g N-/4-acetyloaminofenylo/-N\N'-dwumetyloacetamidyny o temperaturze wrzenia 190-200°/0,l mm Hg i temperatura topnienia 131-134°.Ten sam zwiazek otrzymuje sie takze w analogiczny sposób z 4-acetyloaminoacetanilidu i dwumetyloaminy w obecnosci rteci. PL

Claims (1)

1. Zastrzezenie patentowe Sposób wytwarzania nowych aminofenyloamidyn o ogólnym wzorze 1, w którym R oznacza grupe alkilo¬ wa o 1—3 atomach wegla, R1 oznacza atom wodoru, R2 oznacza grupe o wzorze -COR6 lub grupe o wzorze -S02R7, w których to wzorach R6 oznacza atom wodoru, grupe alkilowa o 1-10 atomach wegla, ewentualnie podstawiona chlorowcem, grupa CF3, lub alkoksylowa o 1-3 atomach wegla albo R6 oznacza cykloalkilowa o 3—6 atomach wegla, grupe alkenylowa o 2—5 atomach wegla, albo oznacza grupe alkoksylowa o 1—8 atomach wegla, ewentualnie podstawiona grupa alkoksylowa o 1—3 atomach wegla lub R6 oznacza grupe fenylowa ewentualnie podstawiona chlorem i/lub grupa acetyloksylowa, ponadto oznacza grupe furylowa albo metyloizo- ksazolilowa, a R7 oznacza grupe alkilowa o 1-3 atomach wegla, R3 oznacza atom wodoru lub chloru, R4 oznacza grupe alkilowa o 1-3 atomach wegla lub alkoksylowa o 1—3 atomach wegla, R5 oznacza grupe alkilowa o 1—3 atomach wegla, a R8 i R9 oznaczaja atomy wodoru, znamienny tym, ze pochodne aniliny o ogól¬ nym wzorze 3, w którym R1, R2, R3, R8 i R9 posiadaja wyzej wymienione znaczenie, poddaje sie reakcji z amidami kwasów karboksylowych o ogólnym wzorze 4, w którym W oznacza atom tlenu lub siarki, a R, R4 i R5 posiadaja wyzej wymienione znaczenie, albo z ich solami albo z ich reaktywnymi pochodnymi, ewentualnie w obecnosci srodków kondensujacychi ewentualnie w obecnosci rozpuszczalników. R-N=C-N I H Wzór 2 Wiór 3 ? R4 \R5 Wzór 4 -/UkU-Wx| ytf R5 Wzór4a v C~N\ ^Alkil-W789 670 H5C2O0C-NH-^ Y-N-C—N N==/ CH3 Wzór 5 CH3 CH3-C0-(VJH^J)-N-C-N^ ~~ CH3 Wzdr 6 H5C200C-HN-f VN=C-N /= XCH3 a Wzdr r 4-CH^C-C0 H3C Wzór B PL
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US4013676A (en) * 1970-06-13 1977-03-22 Bayer Aktiengesellschaft Aminophenylamidines, their production and their pharmaceutical use
US4015012A (en) * 1973-09-18 1977-03-29 Bayer Aktiengesellschaft 4-Acylaminophenylacetamidines and a method for their preparation
DE2346939A1 (de) * 1973-09-18 1975-04-03 Bayer Ag Acylamino-phenyl-acetamidine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US4140795A (en) * 1976-12-09 1979-02-20 Ciba-Geigy Corporation Pesticidal 1,3,5-triazapenta-1,4-dienes
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US4525663A (en) * 1982-08-03 1985-06-25 Burr-Brown Corporation Precision band-gap voltage reference circuit
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BR0107179A (pt) * 2000-09-07 2002-07-02 Bayer Ag Amidinas cìclicas e acìclicas e composições farmacêuticas contendo as mesmas para uso como agentes de ligação de receptor de progesterona
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