• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:

    公开号:SU1402259A3
    申请号:SU853864853
    申请日:1985-03-11
    公开日:1988-06-07
    发明作者:Реснер Манфред；Ретер Вольфганг
    申请人:Хехст Аг (Фирма)；
    IPC主号:
    专利说明:

    (21) 3864853 / 23-04
    (22) P.03.85 (3V) R 3408924.1
    (32) 03/12/84
    (33) DE
    (46) 07.06.88.Byul. Number 21
    (71) Hoechst AG (DE)
    (72) Manfred Rösner and Wolfgang Reter (DR)
    (53) 547.874.07 (088.8)
    (56) French Application No. 2391203, cl. C 07 D 253/06, published 1979
    U.S. Patent No. 4,198,407, Cl. C 07 D 253/06, Published 1980.
    (54) METHOD FOR PREPARING SUBSTITUTED
    (57) The invention relates to substituted triazines, in particular the preparation of substituted 2-phenylhexahydro-1, 2,4-triazine-3,5-diones, in which C (-C4 alkylthiophenoxy or alkylsulfonylphenoxy-phenoxy groups are present in the phenyl moiety. activity, which can be used, for example, in poultry farming for the prevention of coccidosis. The goal is to create new more active and low-toxic substances of the specified class. Their synthesis is carried out by the restoration of the corresponding substituted 2-phenyl-1,2,4-tryaazin-3,5 (2H, 4H) -diones with zinc in ice CHjCGO H or SnCl in HC1, if necessary, in the presence of an inert solvent or diluent at a temperature of from 50 ° C to the boiling point of the reaction mixture. New substances exhibit pronounced activity with respect to pathogens of coccidosis in birds and other animals, and with an increase in the dose of substances in less the extent of the effect is with their effect on weight gain than in the well-known cases.
    i
    WITH
     cm
    The invention relates to a process for the preparation of new substituted 2-phenylhexahydro-1,2,4-triazine-3, 5-diones of the general formula
    ABOUT
    ) -Sh (I)
    R- (o
    Have
    n
    where R is an alkylthiophenoxy group or an alkylsulfonylphenoxy group containing from 1 to 4 carbon atoms in alkyl elements having coccidiostatic activity. The aim of the invention is new derivatives of phenylhexahydro-1,2,4-triazin-3,5-dione, possessing coccidiostatic activity, which is not inferior in its level at low concentrations to structural analogues - derivatives of phenyl-1,2,4-three - ezin-3,5-dione of the general formula
    (Ii)
    where R is 4-methylthiophenoxy (Na) or I 4-metsulfonylphenoxy of group I (116), but exhibiting; compared to the latter
    35
    better tolerability and having a higher chemotherapy index. Example. , 5-Lichloro-4- (A-methylthiophenoxy) -phenyl-hex-Q hydrotriazine-3,5-dione (1a).
    20 g, 5-Dichlor-4- (4-methylthio-phenoxy) phenyl -1,2,4-triazin-3, 5 (2H, 4H) -dione is dissolved by heating in 250 ml of glacial acetic acid . To the prepared solution, 30 g of zinc was added, the mixture is heated for 4 hours under reflux at its boiling point. Then the reaction mass is filtered, the residue containing zinc is heated again with glacial acetic acid and / or 2-methoxyethanol, and then filtered. Solutions
    50
    combined and evaporated in vacuo, water was added to the residue. The precipitate formed is filtered off, washed with water, dried and recrystallized from glacial acetic acid.
    0
    five
    0
    0
    five
    Q

    0
    five
    or 2-methoxyethanol (crystallization can PIG performed in the presence of activated carbon). T. pl. 239 ° C (from 2-methoxyethanol) ..
    NMR spectrum (60 MHz, DMSO-dgTMS), MD: - NH-CH - 3.7-d, I 8 Hz; —NH — CHj— 6.33 Tr, I 8 Hz.
    IR spectrum, KBr, cm-: - NH-CH, 3280; NH-CHi 2910; 1680, 1735.
    P p and M a p 2., 5-Dichloro-4- (4-methylthiophenoxy) -phenyl hexahydro-1,2,4-triazin-3, 5-dione (1a).
    20 g, 5-Lichloro-4- (4-methylthiophenoxy) -phenyl -1,2,4-triazin-3,5- (2H, 4H) -dione is dissolved by heating in 200 ml of glacial acetic acid. To the prepared solution was added 25 g of tin (II) chloride dihydrate and immediately thereafter 100 ml of 1 concentrated hydrochloric acid. The mixture is boiled under reflux for 4 hours, then cooled, the precipitated precipitate is filtered, washed with water until neutral. Recrystallized from 2-methoxyethanol. T. pl. 239 with.
    Example 8 p 3. 2- 3,5-Dichloro-4- (4-methylsulfonylphenoxy) phenyl 3 hexa-hydro-1,2,4-triazine-3,5-dione (16).
    10 g, 5-dichloro-4- (4-methylsulfonylphenoxy) phenyl -1,2,4-triazine-3,5- (2H, 4H) -dione is dissolved by heating in 150 ml of acetic acid, added they are 10 g of zinc dust and boil for 2 hours under reflux, filtered hot, the zinc-containing residue is washed with acetic acid (3 × 50 ml). The mother liquor is evaporated in vacuo. Water is added to the residue, and the precipitated precipitate is filtered off. dried, Recrystallized from methanol in the presence of. activated carbon So pl.240 ° C (with decomposition).
    Example 4, 5-Dichloro-4- (4-methylsulfonylphenox) phenylhexahydro-1,2,4-triazin-3,5-dione (16)
    2 g, 5-Dichlorop-4- (4-methylphosphonylphenyl) phenyl-1,2,4-triazine 3,5- (2H, 4H) -dione is dissolved by heating in 25 ml of acetic acid. 3 g of zinc dust are added and heated for 3 hours at 50 ° C. After filtration of the warm reaction mixture, the zinc containing residue is boiled twice more with acetic acid and filtered. The combined mother liquors are poured into water, the precipitated precipitate is filtered, washed with water, dried and recrystallized from acetic acid or 2-methoxyethanol (if desired in the presence of activated carbon). M.p. 240 C (with decomposition).
    The compounds of formula (I) possess coccidiostatic activity and can be used by both therapeutic and prophylactic agents, for example, when introduced into feed.
    Already in small doses, the compounds of formula (I) show pronounced activity in relation to various pathogens of coccidosis of birds and other animal species with good tolerability. In addition, they affect resistant strains of known drugs.
    The compounds of formula (I) may be administered with drinking water, however, it is preferable to use them in a mixture with suitable carriers. As a carrier material, conventional feed mixtures can be used. In this case, the biologically active substance is admixed to the root in a concentration of from 0.1 to 300 hours, preferably from 0.5 to 30 hours per 1 million hours of feed.
    Coccidiostatic activity and tolerability are studied as follows.
    Cockerels of the leggorn breed at the age of 2 days of the Lomzna selection, weighing 39-41 g at the beginning of the test (1st day), were kept in cages (4 birds per cage). A group of 12 birds (with a randomly selected body weight) received various concentrations, h: 3,10,30,100 parts of compounds (I a, b) and (II a, b) per 1 million hours of feed and tap water from 1st to 22nd day.
    A control group of 12 birds received non-medicated feed and tap water.
    Mean body weight and standard deviation are determined on day 22 and
    statistically compared with the T-test test (, 05).
    The research results are summarized in the table.
    It follows from the table, compounds (1a, b) exhibit such as well-known compounds (Na, b) (at a dose of 3 h per 1 mln. Feed) condiostatic activity (of a single dead animal) with a simultaneous undisturbed increase in weight. With increasing dosage, it can be seen that compounds (1a, b) interfere less with the growth of animals than structural analogues (Na, b).
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining substituted 2-phenylhexahydro-1,2,4-triazin-3, 5-dione of the general formula
    C1
    where R is alkylthiophenoxy or
    alkylsulfonylphenoxy group containing 1-4 carbon atoms in the alkyl moieties,
    characterized in that
    substituted 2-phenyl-1,2,4-triazin-3, 5 (2H, 4H) -dione of the general formula
    ABOUT
    where R has the indicated meanings; zinc is reduced in glacial acetic acid or tin chloride in hydrochloric acid, if necessary in the presence of an inert solvent or diluent at a temperature of from 50 ° C to the boiling point.
    类似技术:
    公开号 | 公开日 | 专利标题
    SU1402259A3|1988-06-07|Method of producing substituted 2-phenylhexahydro-1,2,4-triazine-3,5-diones
    US3949085A|1976-04-06|Anabolic-weight-gain promoting compositions containing isoflavone derivatives and method using same
    SU1140685A3|1985-02-15|Method of obtaining pyradizine substituted derivatives
    US4147780A|1979-04-03|α-Amino-phosphonous acids for inhibiting bacteria and yeast
    SU1371500A3|1988-01-30|Method of producing triazine or acid-additive salts thereof
    WO1984000875A1|1984-03-15|Acyl guanidines
    RU2002737C1|1993-11-15|-1-|-2-isopropylaminoethanol or physiologically acceptable acid addition salt thereof with beta-mimetic and function-stimulating effects in animals
    RU2233278C9|2009-11-27|Pyrimidinone compounds, method for their preparing and pharmaceutical composition
    SU1517760A3|1989-10-23|Method of producing substituted 2-pnenylhexahydro-1,2,4-triazine-3,5 diones
    DD152934A5|1981-12-16|METHOD FOR THE PRODUCTION OF SUBSTITUTED 3-AMINO-SYNDNONIMINES
    Sunkel et al.1988|Synthesis, platelet aggregation inhibitory activity, and in vivo antithrombotic activity of new 1, 4-dihydropyridines
    IL30782A|1972-08-30|Amino guanidines
    US2522854A|1950-09-19|5, 6-dimethylbenzimidazole and acid salts thereof
    US3493572A|1970-02-03|Process for producing quinoxaline-di-n-oxides
    US3907830A|1975-09-23|Isoflavone derivatives
    US4378359A|1983-03-29|Theophyllinylmethyldioxolane derivatives, methods for their preparation and pharmaceutical compositions containing them
    HU195486B|1988-05-30|Process for preparing new pyridine derivatives
    US3658832A|1972-04-25|Novel antimicrobial nitroimidazolyl-1 2 4-oxadiazoles
    US4044130A|1977-08-23|Compositions for the control of microorganisms
    CA1240326A|1988-08-09|2-|-AND 2-|- 3-|-PHTALIMIDINES
    FI63568C|1983-07-11|PROCEDURE FOR THE PREPARATION OF THERAPEUTIC THERAPEUTIC MEASURES I 7-STATIONARY SUBSTITUTES OF 8-AMINOMETHYLSOPHLAVONDERIVAT
    US3086910A|1963-04-23|Central nervous system depressants 3-|-4-quinazolones
    SU1438612A3|1988-11-15|Method of producing |-1 beta-ethyl-1 alpha-|-1,2,3,4,6,6,7,12, 12 b alpha-octahydroindolo |-quinolisin or hydrobromide thereof
    DE1795151B2|1974-08-29|7-square bracket on D-alpha-amino- | square bracket on -cephalosporanic acid
    EP0026989B1|1984-04-18|Nitrosourea derivatives, process for preparing them, and pharmaceutical compositions containing them
    同族专利:
    公开号 | 公开日
    PT80092B|1987-01-05|
    AU3977185A|1985-09-19|
    BG43856A3|1988-08-15|
    EP0154885B1|1989-01-18|
    EP0154885A1|1985-09-18|
    DK110985D0|1985-03-11|
    FI850924A0|1985-03-08|
    CA1238904A|1988-07-05|
    DK110985A|1985-09-13|
    MA20371A1|1988-10-01|
    DD232270A5|1986-01-22|
    ES8602707A1|1985-12-01|
    AU564682B2|1987-08-20|
    CS247098B2|1986-11-13|
    HU192267B|1987-05-28|
    HUT37606A|1986-01-23|
    ZA851794B|1985-11-27|
    US4640917A|1987-02-03|
    PT80092A|1985-04-01|
    NO850951L|1985-09-13|
    IL74554D0|1985-06-30|
    DE3567649D1|1989-02-23|
    GR850608B|1985-07-09|
    PL252340A1|1986-05-06|
    DE3408924A1|1985-09-26|
    IL74554A|1988-09-30|
    FI850924L|1985-09-13|
    PL144518B1|1988-06-30|
    AT40125T|1989-02-15|
    JPS60208969A|1985-10-21|
    PH21079A|1987-07-10|
    KR850006197A|1985-10-02|
    NZ211387A|1988-07-28|
    ES541141A0|1985-12-01|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3655891A|1968-10-16|1972-04-11|Pfizer|2-benzyl-as-triazine-3 5 diones for the control of coccidiosis|
    US3560496A|1968-10-16|1971-02-02|Pfizer & Co C|2-benzyl-as-triazine-3,5 diones|
    DE2149645A1|1970-10-07|1972-09-14|Pfizer|2-Phenyl-as-triazine-3.5- -diones and the use of these compounds for combating coccidiosis|
    US3905971A|1971-03-29|1975-09-16|Pfizer|2-Phenyl-as-triazine-3,5diones|
    US3912723A|1971-03-29|1975-10-14|Pfizer|2-Phenyl-as-triazine-3,5diones|
    DE2606850A1|1976-02-20|1977-09-15|Hoechst Ag|SUBSTITUTED P-AMINOPHENYL-AS-TRIAZINDIONES AND THEIR PRODUCTION|
    DE2722537A1|1977-05-18|1978-11-23|Hoechst Ag|SUBSTITUTED 2-PHENYL-1,2,4-TRIAZINE-3,5- -DIONE, METHOD FOR THE PRODUCTION THEREOF AND THEIR CONTAINING COCCIDIOSTATIC AGENTS|
    IL62151A|1981-02-18|1984-10-31|Abic B M|Hexahydro-1,2,4-triazine-3,5-dione derivatives,their preparation and feed compositions,drinking water and pharmaceutical compositions containing said derivatives|BR8602556A|1984-06-12|1987-02-03|Fmc Corp|HERBICIDE COMPOUND; HERBICIDE COMPOSITION AND PROCESS TO CONTROL THE GROWTH OF UNWANTED PLANTS|
    DE3531919A1|1985-09-07|1987-03-19|Hoechst Ag|SUBSTITUTED 2-PHENYL-HEXAHYDRO-1,2,4-TRIAZINE-3,5-DIONE, METHOD FOR THE PRODUCTION THEREOF, MEANS CONTAINING IT AND THEIR USE|
    GB8602342D0|1986-01-30|1986-03-05|Janssen Pharmaceutica Nv|5 6-dihydro-2--1 2 4-triazine-3 5-diones|
    US4970210A|1987-07-17|1990-11-13|Abbott Laboratories|Triazinone lipoxygenase compounds|
    US4878941A|1987-12-29|1989-11-07|Fmc Corporation|Herbicides|
    DE3814323A1|1988-04-28|1989-11-09|Hoechst Ag|WATER-SOLUBLE PREPARATIONS BY COCCIDIOSTATICA|
    GB8810185D0|1988-04-29|1988-06-02|Glaxo Group Ltd|Chemical compounds|
    DE3826058A1|1988-07-30|1990-02-08|Bayer Ag|AGAINST FISH PARASITES|
    EP0377903A3|1989-01-09|1991-07-17|Bayer Ag|Substituted hexahydro-1,2,4-triazine diones, processes for their preparation, intermediates and their use|
    CN1044905A|1989-02-16|1990-08-29|赫彻斯特股份公司|Fish and entomophagous parasite worm antagonist|
    CA2012004A1|1989-03-15|1990-09-15|Frank Ellis|Chemical compounds|
    US4956004A|1989-05-10|1990-09-11|Fmc Corporation|Herbicidal triazinediones|
    US4985065A|1989-05-10|1991-01-15|Fmc Corporation|Tetrazolinone herbicides|
    DE4030042A1|1990-05-17|1991-11-21|Bayer Ag|USE OF SUBSTITUTED 1,2,4-TRIAZINDIONES|
    EP0476439A1|1990-09-18|1992-03-25|Bayer Ag|Substituted 1,2,4-triazindiones, method for their preparation, intermdiates for it and their use|
    DE4120138A1|1991-06-19|1992-12-24|Bayer Ag|SUBSTITUTED HEXAHYDRO-1,2,4-TRIAZINDIONES, METHOD FOR THE PRODUCTION THEREOF, INTERMEDIATE PRODUCTS THEREOF AND THEIR USE|
    EP0661976A1|1991-08-08|1995-07-12|Mallinckrodt Veterinary Limited|Defaunation method|
    US6787652B1|1999-09-30|2004-09-07|Pfizer, Inc.|6-Azauracil derivatives as thyroid receptor ligands|
    CN110183386A|2016-06-02|2019-08-30|华中师范大学|Diclazuril derivative and its application and the fungicide containing the derivative|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19843408924|DE3408924A1|1984-03-12|1984-03-12|SUBSTITUTED 2-PHENYL-HEXAHYDRO-1,2,4-TRIAZINE-3,5-DIONE, METHOD FOR THE PRODUCTION THEREOF, MEANS CONTAINING IT AND THEIR USE|
    [返回顶部]