• 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:
    The invention relates to new cycloalkane derivatives, a process for the preparation thereof and compositions-particularly feed additives and animal feeds-containing the same. The new compounds of the present invention correspond to the general formula I <IMAGE> I wherein n is 3, 4, 5 or 6; R denotes a phenyl group optionally carrying one or more substituent/s/ selected from the group consisting of halogen, lower alkoxy and lower alkyl; R1 and R2 each represent hydrogen or form together a valence bond; R3 represents lower alkoxy or a phenyl optionally substituted by one or more C1-12 alkoxy. The fodder additives and fodders according to the invention contain as active ingredient an amount of 1 ppm to 85% by weight of a compound of the general formula I in admixture with inert solid or liquid carriers or diluents and can be used to advantage in animal husbandry.
    公开号:SU1274620A3
    申请号:SU833590059
    申请日:1983-05-04
    公开日:1986-11-30
    发明作者:Бенко Пал；Будаи Золтан；Ратц Илдико；Ракоци Ева；Мадьяр Карой；Келемен Иожеф；Манди Аттила
    申请人:Эдьт Дьедьсерведьесети Дьяр (Инопредприятие)；
    IPC主号:
    专利说明:

    The invention relates to a process for the production of new cycloalka new products that can be used to increase the weight gain of farm animals. New derivatives of alkaline alkanes correspond to the general formula I, C: N-lSiH-C-Rii and R, ° 3 or 5; - a phenyl residue which may contain one or two chlorine atoms or lower alkoxy residues, - hydrogen or together R2 and Rj form a valence bond; - a lower alkoxy residue or phenyl containing, as substituents, three lower alkoxy groups with 1-4 carbon atoms. The aim of the invention is to develop a method for producing new derivatives in a series of cycloalkylidene hydrazine, having growth-stimulating activity. Example 1. Getting M- (labels sicarbonyl) -Y - (2-phenylmethylene cyclohexylidene) -hydrazine. To a solution of 37.2 g (0.2 mol) of 2-phenylmethylene cyclohexanone-1 and 200 ml of anhydrous ethyl alcohol was added with stirring a solution prepared from 18.0 g (0.2 mol) of N-methoxycarbonylhydrazine and 40 ml of anhydrous ethyl alcohol. The reaction mixture is heated for a short period of time at its boiling point and refluxed with NIKOM, then cooled, clarified with activated charcoal, filtered, and the filtrate is dried. 50.63 g of the title compound are obtained. The yield is 98%. M.p. 170 - 17GS. Example 2. Preparation of M- (methoxycarbonyl) -H (p-methoxyphenyl metshlen) -cyclohexylidene) -hydrazine To a solution of 22.68 g (0.252 mol) of N-methoxycarbonylhydrazine and 100 ml of benzene with vigorous stirring, add a solution prepared from 50 , 0 (0.23 mol) 2- (p-methoxyphenylmethylene) -cyclohexanol-1 and 300 ml of anhydrous methyl alcohol. The reaction mixture is stirred for 1 hour, clarified with activated carbon and filtered, and the filtrate is cooled. The result is 63.05 g of the title compound as a crystalline substance. Yield 94.65%. M.p. 162 -. Example 3, Preparation of M- (methoxycarbonyl) (phenylmethylene) -cycloheptylideneJ-hydrazine. 9.0 g (0.1 mol) of N-methoxycarbonyl hydrazine is dissolved in 250 ml of anhydrous ETI. POD alcohol, after which, with stirring, 20.0 g (0.1 mol) of 22-phenylmethylene cycloheptanone-1 is added to the prepared solution. The reaction mixture, with stirring, is heated with activated carbon, filtered, and then the frit fraction is cooled to carry out crystallization. The result is 24.78 g of the title compound. Yield 91%. M.p. 143-145 ° C. Example4. Preparation of H- (methoxycarbonyl) -H (p-chlorophenylmethylene) -cyclohexylidene -hydrazine. 33.32 g (1.515 mol) of 2- (p-chlorophenylmethylene) -cyclohexanone-1 and 13.5 g: (0.151 mol) C-methoxycarbonylhydra-. Zina is dissolved in 230 ml of isopropyl alcohol. The reaction mixture is heated at reflux temperature for several hours, then cooled, clarified with activated carbon, filtered, and then the filtrate is cooled to effect crystallization. The result is 41.2 g specified in the end of the output of 93.2%. M.p. connection of 160.5 to 162 C. Example 5. Preparation of N- (Metoxycarbonyl) -M (2, 6-dichlorophenylmethylene) -cyclohexylidene-hydrazine. 25.52 g (0.1 mol) of 2- (2, b-dichlorophenylmethylene) -cyclohexanone-1 and 9.0 g (0.1 mol) of M-methoxycarbonylhydrazine are heated in 150 ml of anhydrous ethyl alcohol for 3 hours at boiling point the reaction mixture. The reaction mixture was clarified with activated charcoal, filtered, and the filtrate was then cooled to crystallize. 28.47 g of the title compound are obtained. Exit 87%. Calculated,%: C 55.06; H 4.93; C1 21.67; N 8.56. 15,., (327.20) 15 16 a Found,%: C 55.21; H 4.90; C1 21.58; N 8.55. Example 6. Preparation of N- (methodic cicarbonate) -N (3 4 -dimethoxyphenylmethylene) -cyclohexylidene-hydrazine. A solution containing 24.63 g (0.1 mol) of 2- (3,4-dimethoxyphenylmethylene) -cyclohexanone-1 and 9.0 g (0.1 mol) of H-methoxycarbonyl hydrazine in 150 ml of methyl alcohol, heated for 2 hours at its boiling point. After cooling, the crystallized product that precipitated out is filtered off. As a result, 21.87 g of the title compound are obtained. Yield 68.7%. Calculated,%: C 64.13; H 6.97; N 8,8. (318.37) Found,%: C 63.85; H 6.77; N 8.78. Example 7. Obtaining H- (methoxycarbonyl) -N - (2-benzylcyclohexylidene) -hydrazine. A solution containing 18.83 g (0.1 Vol) of 2-benzylcyclohexanone-1 9.0 g (0.1 mol) of N-methoxycarbonyl hydrazine and 100 ml of anhydrous ethanol is heated for 2 hours at boiling point. After cooling, the crystallized product precipitated from the filtrate. As a result, 18.2 g of the title compound are obtained. Yield 69.9%. ; Calculated,%: C 69.2; H 7.74; N 10.76. C. (260.33) Found,%: C 69.0; H 7.50; N 10.75. EXAMPLE 8 Preparation of N- (3,5-Dimethoxy-4-hexyloxybenzoyl) -N 2 (phenylmethylene) -cyclohexylidene-hydropasine. To a solution of 29.6 g (0.1 mol) of hydrazide of 3,5-dimethoxy-4-hexyloxybenzoic acid in 110 ml of anhydrous
    ethyl alcohol was added a solution, js containing 18.6 g (0.1 mol) of 2-phenylmethylene cyclohexanone-1 in 50 ml of anhydrous ethyl alcohol. Reaction.
    boil and then cool. The precipitated crystalline substance is filtered off. As a result, 35.3 g of the product specified in 620 620, 4 are obtained. The mixture is heated for 1 h at its boiling point, after which the mixture is cooled and filtered. 36.3 g of the title compound are obtained. The yield is 78.2%. M.p. 158 160С. Example 9. Obtaining N- (3,4, 5-trimethoxybenzoyl) -Y - (phenylmethylene) -cyclohexylidene -hydrazine. To a solution of 22.6 g (0.1 mol) of hydrazide of 3,4,5-trimethoxybenzoic acid in 220 ml of anhydrous ethyl alcohol was added a solution prepared from 18.6 g (0.1 mol) of 2-phenyl-methyl-cyclohexanone-1 and 90 ml of anhydrous ethyl alcohol. The reaction mixture is heated for 1 h at its boiling point, after which it is cooled and filtered. 68.3 g of the title compound are obtained. Yield 68.3%. M.p. 181 - 182С. Example 10. Preparation of N- (3. 5-dimethoxy-4-decyloxybenzoyl) -K - (phenylmethylene) -cyclohexylidene-hydrazine. To a solution containing 17.6 g (0.05 mol) of 3,5-dimethoxy-4-decyloxybenzoic acid hydrazide in 100 to 100 ml of anhydrous ethyl alcohol, a solution prepared from 9.2 g (0.05 mol ) 2-phenylmethnlen. Cyclohexanone- and 40 ml of anhydrous ethyl alcohol. The reaction mixture is heated at reflux temperature e6 for 2 hours and then cooled. The crystalline product which has precipitated out is filtered off. 18.85 g of the title compound are obtained. The yield is 72.4%. M.p. 161 - 162С. Example 11. Obtaining N- (3, 5-dimethoxy-4-butoxybenzoyl) -Y (phenylmethylene) -cyclopentylidene-hydrazine. To a solution containing 26.8 g (0.1 mol) of 3,5-dimethoxy-4-butoxybenzoic acid hydrazide in 200 ml of anhydrous ethyl alcohol, add a solution prepared from 17.2 g (0.1 mol) 2 -phenylmethylene cyclopentanone-1- and 50 ml of anhydrous, ethyl alcohol. The reaction mixture is heated for 1 hour at its compound head. The output of 83.8%. M.p. 226 - 227 ° C. Calculated,%: C, 71.07; H, 7.16; N 6.63. (53) Found: C, 70.86; H 7.32; N 6.66. 326 nm (30,200). Example 12. Getting N-. J3,5-dimethoxy-A-ethoxybenzoyl) -N - (. Phenylmethylene) -cyclopentio7idene-hydrazine. To a solution containing 30.2 g (0.126 mol) of 3,5-dimethoxy-4-ethoxybenoic acid hydrazide in 250 ml of anhydrous ethyl alcohol, is added a solution prepared from 21.8 g (0.126 mol) of 2-phenylmethylenecyclopentanone-1 and 50 ml of anhydrous ethyl alcohol. The reaction mixture is heated for 1 hour at its boiling point, after which it is cooled. The precipitated crystalline material is filtered off and dried. 39.78 g of the title compound are obtained. The output of 80.0%. Mp 239-240 ° C. EXAMPLE 13 Preparation of N- (3, 5-Dimethoxy-4-butoxybenzoyl) -N-phenylmethylene) -cyclohexyl hydrazine. To a solution containing 12.5 g (0.045 mol) of 3,5-dimethoxy-4-butoxybenzoic acid hydrazide in 150 ml of anhydrous ethyl alcohol was added a solution prepared from 9.3 g (0.05 mol) of 2-phenylmetershylene cyclohexanone- 1 and 100 ml of anhydrous ethyl alcohol. The reaction mixture is heated for 1 hour at its boiling point, after which it is cooled, and the crystalline substance is precipitated. 12.38 g of the title compound are obtained. Vkskhod 63%. M.p. 180 - 181С. Example 14. Obtaining N (3,5-dimethoxy-4-ethoxybenzoyl) -Y (phenylmethylene) -cyclohexylidene -hydrazine. To a solution containing 24.0 g (0.1 mol) of 3,5-dimethoxy-4-ethoxybenzoic acid hydrazide in 200 ml of anhydrous ethyl alcohol, a solution prepared from 18.6 g (0.1 mol) 2 is added. -phenylmethylene cyclohexanone-1 and 200 ml of anhydrous 206 th ethyl alcohol. The reaction mixture is heated for 1 hour at its boiling point, after which it is cooled. Precipitated in the sediment. the crystalline substance is filtered off and the calathe. The result is 26.5 g of the title compound. Yield 65%. M.p. 176 -. 177C. The activity of the compounds of general formula I according to the invention, which is manifested in the increase of the weight gain of animals, has been proven by means of follow-up experiments. Pigs were used as experimental animals. For each test, a group of six animals was taken, and each experiment (in each case with 6 pigs) was repeated 3 times. The feed used for feeding pigs contained 50 mg / kg of the compound used in the dough. The animals were fed under identical conditions, and all groups of animals ate the same amount of feed of identical composition. Another group received the same amount of feed, but this feed contained flavomycin. The control group received the same amount of feed, but without the test compound. Weight gain was recorded every day. The results are presented in Table. 1. Table 1 Required dl weight of 1 kg of the exact weight ratio,% of the amount of feed per control group,% Example 2 Flavomycin Control The activity of the new compounds of general formula I corresponding to the invention was also tested on groups of groups. consisting of 10 animals. The feed contained 50 mg / kg of the test compound. Experimental animals fed
    feed for 40 days. Each experiment was repeated 3 times.
    The results are presented in Table. 2
    Table 2.
    Presented in table. 1 and 2, the results show that animals receiving feed using the new derivatives of cycloalkyls corresponding to the invention, give a significantly higher weight gain than. animals of the control groups. At the same time, a certain weight gain is achieved with a significantly smaller amount of feed, which indicates a significantly better absorption of feed.
    Thus, new derivatives of cycloalkanes are almost non-toxic to useful animals.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    Method for preparing cycloalkylidene hydrazine derivatives of general formula I
    (CH2) nC —N — NH — C — R / i
     five
    RI-C-R2 H
    n - 3 or 5;
    R, is phenyl, which may be substituted by one or two
    chlorine atoms, one or two lower alkoxy residues;
    and RJ is hydrogen or together form a valence bond;
    R is a lower alkoxy residue or phenyl, substituted by three alkoxy groups with 1-4 carbon atoms, and y and i with the fact that keo tl and h
    tone of general formula II
    (sn) n with
    Rj-c-R2
    n
    Rj
    have indicated
    and
    introduced into interaction with the hydrazine derivative of general formula HI
    H2N-1 H-C R / O
    where RJ has the indicated values in the environment of an aromatic hydrocarbon or lower alcohol at a temperature of from 40 ° C to the boiling point of the reaction mass.
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    法律状态:
    优先权:
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