PL93694B1 - - Google Patents

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PL93694B1
PL93694B1 PL1971188508A PL18850871A PL93694B1 PL 93694 B1 PL93694 B1 PL 93694B1 PL 1971188508 A PL1971188508 A PL 1971188508A PL 18850871 A PL18850871 A PL 18850871A PL 93694 B1 PL93694 B1 PL 93694B1
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    • 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
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P33/00—Antiparasitic agents
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    • 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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    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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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    • C07D307/10—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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    • C07D307/18—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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    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Organic Chemistry (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Description

Przedmiotem wynalazku jest sposób wytwarza¬ nia nowych aminofenyloamidyn, nadajacych sie do zwalczania pasozytów, zwlaszcza robaków.Z opisu patentowego St. Zjedn. Am. nr 3184482 znane sa zwiazki przedstawione na rysunku wzo- 5 rem ogólnym 2, w którym R oznacza fenyl, ewen¬ tualnie podstawiony miedzy innymi grupa alki- loaminowa, acyloaminowa, alkiloaminokarboksylowa, zas R1 i R2 = H lub alkil. W cytowanym opisie pa¬ tentowym wymienione sa znane acyloaminofeny- io loformamidyny, takie jak N-(p-acetamidofenylo)- N'N'-dwumetyloformamidyna i N-fenyloacetamidy- ny, jak N-(p-chlorofenylo)-N'N'-dwumetyloacetami- dyny. Zwiazki te jednak niie sa aktywne przeciw¬ ko nizej wymienionym robakom. !5 Stwierdzono, ze do zwalczania pasozytów, zwlasz¬ cza robaków, wybitnie nadaja sie nowe amimofeny- loamidyny 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 20 grupe o wzorze -S02R7, w których to wzorach R6 oznacza atom wodoru, grupe alkilowa o 1—10 ato¬ mach wegla, ewentualnie podstawiona chlorowcem, grupa CF3 lub alkoksylowa o 1—3 atomach wegla, albo R5 oznacza grupe cykloalkilowa o 3—6 ato- 25 mach wegla, grupe alkenylowa o 2—5 atomach wegla, albo oznacza grupe alkoksylowa o 1—8 ato¬ mach wegla, ewentualnie podstawiona grupa alko¬ ksylowa o 1—3 atomach wegla lub R6 oznacza grupe fenylowa, ewentualnie podstawiona chlorem 30 i/lub grupa acetoksylowa, ponadto oznacza grupe furylowa, lub metyloizoksazolilowa, a R7 .oznacza grupe alkilowa o 1—3 atomach wegla, R3* oznacza atom wodoru lub chlorku, R4 oznacza grupe alki¬ lowa 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 oraz ich sole.Sposobem wedlug wynalazku nowe aminofenylo- amidyny o wzorze 1, w którym wszystkie symbole maja wyzej podane znaczenie, otrzymuje sie w ten sposób, ze aminy o ogólnym wzorze 3, w którym R4 i R5 posiadaja wyzej wymienione znaczenie, poddaje sie reakcji z anilidami o ogólnym wzorze 4, w którym W, R, R1, R2, R3, R8 i R9 posiadaja wyzej wymieniane znaczenie, albo z ich solami albo z ich reaktywnymi pochodnymi, ewentualnie w obecnosci rozpuszczalników i ewentualnie w o- becnosci srodków kondensujacych.Reaktywnymi pochodnymi anilidowymi sa na przyklad zwiazki otrzymywane przez reakcje ani- lidów o wzorze 4 z kwasami nieorganicznymi, jak na przyklad z chlorowodorem, trójchlorkiem boru, kwasem siarkowym albo z nieorganicznymi lub organicznymi halogenkami kwasów, jak na przy¬ klad z tlenochlorkiem fosforu, pieciochlorkiem fos¬ foru, fosfogenem, chlorkiem tionylu, bromkiem ben¬ zoilu, p-toluenosulfochlorkiem z mieszanina fosge- nu (chlorek glinowy, fosgen) chlorowodór lub fos- gen/tlenochlorek fosforu albo z fluoroboranami 93 69493 694 3 trójalkilooksaniowymi, w których grupy alkilowe zawieraja 1—5 atomów wegla lub z siarczanami dwualkilowymi, w których grupy alkilowe zawieraja 1—5 atomów wegla lub z halogenkami alkilowymi, w których grupy alkilowe zawieraja 1—5 atomów wegla. Jako dalsze, reaktywne pochodne anilidowe mozna wymienic acetale i tioacetale o ogólnym wzorze 4a, w którym W, R, R1, R2, R8, R8 i R9 posiadaja wyzej podane znaczenie, a „Alkil" grupy alkilowe zawierajace 1—4 atomów wegla i w któ¬ rych obie grupy alkilowe moga lacznie stanowic czesci skladowe pierscienia o pieciu, szesciu lub siedmiu czlonach.Dalszymi reaktywnymi pochodnymi anilidowymi sa iminoestry o ogólnym wzorze 4b, w którym W, R, R1, R2, R8, R8 i R9 posiadaja wyzej wymienio- fff TD?nit™^ a „Alkil" oznacza grupe alkilowa za- wjef^fefas l—A atomów wegla. r Reakcje wedlug powyzszego wariantu prowadzi Sie w takich samych warunkach reakcji (stosunek frfoow^^emperatura srodki kondensujace, roz- *#»•*] »* . l •:-. ¦ puszczaloiki),- jak proces wedlug wariantu pierw¬ szego.Jako srodki kondensujace stosuje sie na przy¬ klad kwasy nieorganiczne, jak na przyklad kwas chlorowodorowy, trójchlorek baru, kwas siarko¬ wy, albo nieorganiczne lub organiczne halogenki kwasowe, jak na przyklad tlenochlorek fosforu, pieciochlorek fosforu, fosgen, chlorek tionylu, bro¬ mek benzoilu, p-tolunosulfochlorek lub mieszanina fosgen/chlorek glinowy lub fosgen/chlorowodór lub fosgen/tlenochlorek fosforu albo fluoroborany, trójalkilooksaniowe zawierajace 1—5 atomów we¬ gla w grupach alkilowych, albo w siarczany dwualkilowe, zawierajace 1—5 atomów wegla w grupach alkilowych albo z halogenkami alkilo¬ we zawierajace 1—5 atomów wegla.W przypadku reakcji tioamidów o ogólnym wzo¬ rze 4, w którym W oznacza atom siarki, korzystne moze byc stosowanie dodatkowo do tych srodków kondensujacych, albo bez nich, srodków odsiarcza¬ jacych, jak na przyklad HgC, Ag20 lub Hg(CN)? Korzystnie jest wprowadzanie reagentów w ilos¬ ciach stechiometrycznych.Jako rozpuszczalniki moga znalezc zastosowanie wszystkie obojetne rozpuszczalniki organiczne, jak aromatyczne, ewentualnie chlorowcowane, weglo¬ wodory, jak na przyklad benzen, toluen, dwuchlo- robenzen, ewentualnie chlorowane, alifatyczne we¬ glowodory, jak na przyklad chlorek metylenu i chloroform lub czterometylenosulfon, lub takze niz¬ sze alifatyczne alkohole, jak na przyklad metanol i etanol.Reagenty miesza sie razem korzystnie w tem¬ peraturze pokojowej, okolo 20°C i ewentualnie w celu doprowadzenia reakcji do konca ogrzewa sie je do temperatury okolo 30°—150°C, korzystnie 70°—120°C.Zwiazki otrzymywane sposobem wedlug wyna¬ lazku posiadaja charakter zasadowy. Moga byc stosowane jako wolne zasady lub pod postacia ich soli, na przyklad chlorowcowodorków, korzystnie chlorowodorków, siarczanów, fosforanów, azota¬ nów, octanów lub naftalenosulfonianów.Szczególnie korzystne wlasciwosci posiadaja 40 45 50 55 65 zwiazki o ogólnym wzorze 1, w którym R ozmacza korzystnie grupe alkilowa, zawierajaca 1 lub 2 atomy wegla, R1 oznacza atom wodoru, R2 pznacza grupe o wzorze -COR6 lub grupe o wzorze S02R7, przy czym R6 oznacza korzystnie atom wodoru, grupe alkilowa o prostym lub rozgalezionym lan¬ cuchu, zawierajaca 1 do 3 atomów wegla i posia¬ dajaca ewentualnie wiazanie podwójne i ewentualnie podstawiona grupa trójfluorometylowa lub grupa me- toksylowa, albo grupe cykloalkilowa, zawierajaca 3 lub 5 atomów wegla, albo grupa furylowa, albo 3-metyloizoksazolilowa lub grupe fenylowa albo grupe alkoksylowa zawierajaca 1—4 atomów wegla, posiadajaca ewentualnie wiazanie potrójne i ewen¬ tualnie podstawione grupa metoksylowa, a R7 ozna¬ cza korzystnie grupe alkilowa zawierajaca 1 lub 2 atomy wegla, R3 oznacza korzystnie atom wodoru, R8 oznacza atom wodoru, R5 oznacza grupe alki¬ lowa, zawierajaca 1 lub 2 atomy wegla, a R4 ozna¬ cza grupe alkilowa, zawierajaca 1 lub 2 atomy wegla, albo grupe metoksylowa oraz ich sole z fizjo¬ logicznie dopuszczalnymi kwasami. Korzystnymi solami nowych zwiazków sa chlorowodorki.Sposób wedlug wynalazku jest blizej wyjasnio¬ ny w nastepujacych przykladach. Wszystkie tem¬ peratury podano w stopniach Celsjusza.Jak juz wspomniano, nowe zwiazki nadaja sie wybitnie do zwalczania pasozytów, zwlaszcza ro¬ baków. Nalezy uwazac za wyjatkowo niespodzie¬ wane i niedajace sie przewidziec, ze wprowadzenie grupy acyloaminowej lub sulfonyloaminowej do pierscienia fenylowego N-fenyloacetamidyn spowo¬ duje wystapienie wysokiej aktywnosci przeciw ro¬ bakom. Nastepnie okazalo sie, ze zwiazki te w sposób istotny dzialaja lepiej, niz inne znane srod¬ ki przeciw robakom o tym samym kierunku dzia¬ lania, jak na przyklad (hydroksynaftoesan befe- nium), fenylonodwuizotiocyjanian-(l,4), perchloro- etylen, tiabendazole i parbendazole. Szczególnie nalezy pokreslic, ze przy jednorazowym podaniu uzyskiwano bardzo dobre wyniki.Zwiazki otrzymane sposobem wedlug wynalaz¬ ku wykazuja niespodziewanie dobre dzialanie o szerokim zakresie przeciwko nastepujacym roba¬ kom i nicieniom i tasiemcom.I. Nicienie 1. Ancylostoma caninum, Uncinaria stenocephala i Bumiostomum trinonocaphalum z rodziny Ancy- loastomatidae; 2. Haemonehus contortus, Trichostrongylus co- lubriformia, Cooporia pumctata, Ostertagie circumc- inata, Nippostrongylus muris i Nemstospircides du- bius z rodziny Trichostrongylidne; 3. Ossephagostonum columbianum i Chabertia- ovina z rodziny Strongylidae; 4. Strongyloides ratti z rodziny Rhabddtidae; . Toxocarm canis, Toxascaris laonina i larwy Ascaria suum z rodziny Ascarididae; 6. Aspiculuris tetraptera z rodziny Oxyuridae* 7. Heterakie spumosa z rodziny Heterakidae.II. Tasiemce 1. Hymenolepis nana i Hymenolepis mierostoma z nadrodziny Taenioidea.Skutecznosc zbadano za pomoca prób na zwie-93 694 6 rzetach zakazonych pasozytami stosujac podawanie doustne i pozajelitowe. Zwierzeta poddawane ba¬ daniom bardzo dobrze znosily stosowane dawki.Nawet przy podawaniu dawek 10 razy do 100 razy wiekszych niz terapeutycznie potrzebna, zwierzeta doswiadczalne przezyly leczenie.Przyklad I. 96 g 4-acetyloaminoacetanilidu w 300 ml toluenu miesza sie w ciagu 6 godzin w temperaturze 20° z 76 g tlenochlorku fosforu. Na¬ stepnie wkrapla sie roztwór 60 g dwumetyloaminy w 200 ml toluenu i ogrzewa do wrzenia pod chlod¬ nica zwrotna w ciagu nocy. Po przeróbce analo¬ gicznej do opisanej w przykladzie I otrzymuje sie 27 g N-(4-acetyloaminofenylo)-N',N'-dwumetyloace- tamidyny o temperaturze wrzenia 190—20.0°/0,l ma Hg. Po rozpuszczeniu i wytraceniu zwiazek ten topi sie w temperaturze 131—134°C.Przyklad II. 98 g eteru 4-acetyloaminofenylo- acetyloiminoetylowego ogrzewa sie z roztworem 26 g dwumetyloaminy w 100 ml etanolu w ciagu 2 dni w temperaturze 28°, a nastepnie w ciagu 6 godzin w zamknietej rurze w temperaturze 120— 130°C. Po odparowaniu i destylacji otrzymuje sie 57 g N-(4-acetyloaminofenylo)-N',N'-dwumetyloace- tamidyny o temperaturze topnienia 131—134°. Ana¬ logicznie otrzymuje sie N-(4-acetyloaminofenylo)- acetamidyne przez reakcje eteru 4-acetyloiminofe- nylo-acetyloiminoetylowego z amoniakiem. Ten sam zwiazek powstaje takze przez reakcje 4-aminoace- tanilidu z eterem acetyloiminoetylowym. PL

Claims (1)

1. Zastrzezenie patentowe Sposób wytwarzania nowych aminofenyloamidyn o ogólnym 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 R6 oznacza atom wodoru, grupe alkilowa o 1—10 ato¬ mach wegla, ewentualnie podstawiona chlorowcem, grupa CF3 lub alkoksylowa o 1—3 atomach wegla albo R6 oznacza grupe cykloalkilowa o 3—6 ato¬ mach wegla, grupe alkenylowa o 2—5 atomach wegla, albo oznacza grupe alkoksylowa o 1—8 ato¬ mach wegla, ewentualnie podstawiona grupa al¬ koksylowa o 1—3 atomach wegla lub R6 oznacza grupe fenylowa — ewentualnie podstawiona chlo¬ rem i/lub grupa acetyloksylowa, ponadto oznacza grupe furylowa albo metyloizoksazolilowa, a R7 oznacza grupe alkilowa o 1—3 atomach wegla, R8 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 i—3 atomach wegla, a R8 i R9 oznaczaja atomy wodoru, znamienny tym, ze aminy o ogólnym wzo¬ rze 3, w którym R4 i R5 posiadaja wyzej wymie¬ nione znaczenie, poddaje sie reakcji z analidami o ogólnym wzorze 4, w którym W, R, R1, R2, R8, R8 i R9 posiadaja wyzej wymienione znaczenie, albo z ich solami albo z ich reaktywnymi pochodnymi, ewentualnie w obecnosci rozpuszczalników i ewen¬ tualnie w obecnosci srodków kondensujacych. WzóM R-N=C-W I H Wzór 2 HN Wzór 393 694 .8 Wzór A W Vnh-£-r NH-C Wzór Aa R .W-AlkiK W-AlkU'' HzcMb OZGraf. Lz. 1441 (110+25 egz.) Cena 10 zl 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
DE2758005A1 (de) * 1977-12-24 1979-06-28 Bayer Ag Phosphonylureidobenzol-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US4525663A (en) * 1982-08-03 1985-06-25 Burr-Brown Corporation Precision band-gap voltage reference circuit
JPS6118603A (ja) * 1984-07-04 1986-01-27 極東開発工業株式会社 塵芥収集車における安全装置
JPS6230943U (pl) * 1985-08-09 1987-02-24
GB8903592D0 (en) * 1989-02-16 1989-04-05 Boots Co Plc Therapeutic agents
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
KR20040105250A (ko) * 2002-05-03 2004-12-14 이 아이 듀폰 디 네모아 앤드 캄파니 아미디닐페닐 화합물 및 그의 살진균제로서의 용도
DE102007061262A1 (de) 2007-12-19 2009-06-25 Bayer Animal Health Gmbh Neue Verwendung von Tribendimidin
DE102008030764A1 (de) 2008-06-28 2009-12-31 Bayer Animal Health Gmbh Kombination von Amidin-Derivaten mit cyclischen Depsipeptiden
CN102344391B (zh) * 2011-07-28 2013-12-25 山东新华制药股份有限公司 N-(4-乙酰氨基苯基)-n′，n′-二甲基乙脒的合成方法

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RO58997A (pl) 1976-02-15
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