• 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 carbazic acid derivatives, a process for the preparation thereof and compositions-particularly feed additives and animal feeds-containing the same. The new compounds according to the invention correspond to the formula (I) R1=N-NH-COOR3 (I) wherein R1 stands for a C7-12 cycloalkylidene group, an indanylidene group or a group of the formula (IX) <IMAGE> (IX) wherein A represents a phenyl group optionally carrying one or more identical or different substituents selected from the group consisting of halo, nitro, hydroxy, C1-4 alkoxy, C1-4 alkyl, amino or C1-4 alkoxycarbonylhydrazino; phenyl-(C1-4 alkyl), C1-16 alkyl, C3-7 cycloalkyl or indolyl, or a C3-C6 cycloalkyl group substituted by a C3-C6 cycloalkyl group; R2 denotes a hydrogen atom, a C1-16 alkyl or a C3-7 cycloalkyl group; and R3 represents a C1-4 alkyl group.
    公开号:SU1299503A3
    申请号:SU833593065
    申请日:1983-05-04
    公开日:1987-03-23
    发明作者:Бенко Пал；Будаи Золтан；Ратц Илдико；Ракоци Ева；Мадьяр Карой；Келемен Йожеф；Манди Аттила
    申请人:Эдьт Дьедьсерведьесети Дьяр (Инопредприятие)；
    IPC主号:
    专利说明:

    The invention relates to a process for the preparation of new derivatives of hydrazino carbonic acid of the formula
    R, N - NH - COOR,
    (one)
    where R, is cycloalkylidene Cg-C, 2, indanilidene or a group of formulas
    A - C in which A is a phenyl group “2 0
    a pa that may be substituted by one or more substituents selected from halogen, nitro, amino, hydroxy, lower alkoxy groups, or A is indolyl, lower alkyl, cyclohexane
    R is hydrogen, lower alkyl, al-, kil C,
    f5
    R, - C, M5
    C alkyl.
    25
    These compounds have properties to increase the weight gain of useful animals.
    The aim of the invention is to develop a method for producing new derivatives of hydrazinolic acid, which have a higher efficiency in increasing the weight gain of animals.
    Example 1. Preparation of 3- (o6-isopropyl-benzylidene) -hydrazinolic acid methyl ester.
    To a solution of 44.46 g (0.3 mol) of isobutyrophenone and 200 ml of methanol, 3 ml of acetic acid are first added and then 27 g of methyl carbazate
    To a solution of 39.65 g (0.3 mol) of 1-in-5 danone and 300 ml of methanol, 3 ml of acetic acid are first added and then 27 g (0.3 mol) of methyl carbazate. The reaction mixture is heated to boiling point for 1 hour, then it is clarified by boiling with charcoal and filtered. The filtrate is cooled with ice water. 43.7 g of the expected compound are obtained. The resulting white crystals melt at 155-156 ° C. As a result of the evaporation of the mother liquor to about a quarter of the original volume, an additional amount (12.3 g) of the desired compound is obtained. Yield 91.5%.
    Example 4: Preparation of 3- (o-amino-benzylidene) -hydride-rasinugnolic acid methyl ester.
    The experiment was carried out as described in Example 3, with the only difference that 36.35 g (0.3 mol) of 2-aminobenzine dehydrate were taken as the starting material. 50 g of the expected compound are obtained. Vkod 86.35%. M.p. 149-150 ° C.
    Example 5. Preparation of 3-cyclooctylidene-hydrazincaric acid methyl ester.
    The test was carried out as described in Example 1, with the only difference that 20 was used as the starting compound.
    1 .f i I iw i ±, iiiV4 4 - “- - -..-. N-ir / - chl V
    The reaction mixture is heated for 5 minutes 37.86 g (0.3 mol) of cyclooctanone. 49 g of the expected compound are obtained.
    , about ,
    1 h before boiling, then clarified and evaporated under reduced pressure to half the original volume. The residue is cooled. A white oily substance precipitates. 64.2 g of the expected compound are obtained. Yield 97.3%., M.p. 78-80 C. The product can be purified by recrystallization from gasoline.
    Example 2. Obtaining methyl ester of E- (3-indolyl-methylene) 7 hydrazugolla acid.
    To a solution of 36.29 g (0.25 mol), the yield of 82.5%. M.p. 93-94 S.
    Example 6. Obtaining methyl ester of 3- (p-nitro-benzylidene) -hyd On rasinugnol acid.
    The test was carried out as described in Example 3, with the difference that 45.34 g (0.3 mol) of p-nitro-benzalde 5 guide were used as the starting compound. 61.5 g of the title compound are obtained. Zykhod 91.9%. M.p. 212-213 p.
    Example 7. Obtaining methyl ester of 3- (t-phenyl-hexadecylidene) - dol-3-aldepad and 300 ml of methanol. hydrazuginic acid, 3 ml of acetic acid, 47.48 g (0.15 mol), palmitopheno- and then 0.25 mol of methylcarbazene and 13.5 g (0.15 mol) of methylcarbazate are added to the mixture. The reaction mixture is reacted for 1 hour in the same way as it is heated to the boiling point, example 1. Obtain 47.3 g (81.3%) of which are clarified. From the filtrate at 55 of the title compound. Yield 81.3%.
    50 ml of water are added to precipitate crystals. 51.5 g of the expected compound are obtained. Yield 94.9%. T.Sh1.144-145 with.
    M.p. 68-69 ° C.
    Example 8. Obtaining methyl ester of 3- (1-benzyl-propylidene) - hydrazugolic acid.
    Example 3. Preparation of 3- (1-indanilidene-hydrazincaric acid methyl ester.
    To a solution of 39.65 g (0.3 mol) of 1-indone and 300 ml of methanol, 3 ml of acetic acid are first added and then 27 g (0.3 mol) of methyl carbazate. The reaction mixture is heated to boiling point for 1 hour, then it is clarified by boiling with charcoal and filtered. The filtrate is cooled with ice water. 43.7 g of the expected compound are obtained. The resulting white crystals melt at 155-156 ° C. As a result of the evaporation of the mother liquor to about a quarter of the original volume, an additional amount (12.3 g) of the desired compound is obtained. Yield 91.5%.
    Example 4: Preparation of 3- (o-amino-benzylidene) -hydride-rasinugnolic acid methyl ester.
    The experiment was carried out as described in Example 3, with the only difference that 36.35 g (0.3 mol) of 2-aminobenzine dehydrate were taken as the starting material. 50 g of the expected compound are obtained. Vkod 86.35%. M.p. 149-150 ° C.
    Example 5. Preparation of 3-cyclooctylidene-hydrazincaric acid methyl ester.
    The experiment was carried out as described in Example 1, with the only difference that as the starting compound,
    , about ,
    Yield 82.5%. M.p. 93-94 S.
    Example 6. Obtaining methyl ester of 3- (p-nitro-benzylidene) -hyd On rasinugnol acid.
    The test was carried out as described in Example 3, with the difference that 45.34 g (0.3 mol) of p-nitro-benzalde 5 guide were used as the starting compound. 61.5 g of the title compound are obtained. Zykhod 91.9%. M.p. 212-213 p.
    Example 7. Preparation of methyl 3- (t-phenyl-hexadecylidene) -hydrazuunic acid, 47.48 g (0.15 mol) palmitopheno-a and 13.5 g (0.15 mol) methylcarbazate are reacted in the same way as in example 1. 47.3 g (81.3%) of the title compound are obtained. Yield 81.3%.
    M.p. 68-69 ° C.
    Example 8. Obtaining methyl ester of 3- (1-benzyl-propylidene) - hydrazugolic acid.
    The experiment was carried out analogously to Example 1 with the difference that 44.46 g (0.3 mol) of ethyl benzyl ketone was used as the starting compound. 66 g of the expected compound are obtained. The output g of 99.9%. M.p. SiD c.
    Example 9. Preparation of methyl 3- (2, 4-dihydroxy-benzylidene) -hydrazinugoic acid ester.
    To a solution of 34.5 g (0.25 mol) of 2.4-10 dihydroxybenzaldehyde and 300 ml of methanol are first added 3 ml of acetic acid and then 22.5 g (0.25 mol) of methyl carbazate. The reaction mixture is heated for 2 hours to t5 at the boiling point, after which the solution is clarified by boiling with charcoal, filtered and the filtrate is cooled. 49.2 g of the expected compound are obtained. Yield 93.4%. M.p. 205 ° C.20
    Example 10. Preparation of 3- (3, 4, 5-trimethoxy-benzylidene) -hydrazinugolic acid methyl ester.
    30.86 g (0.2 mol) of 3,4,5-trimethoxy-benzaldehyde and 18 g (0.2 mol) of 25 methyl carbacate are reacted in a manner similar to Example 1. 48.6 g of the title compound are obtained. Yield 86%. White crystals melt at 140-141 ° C. 30
    Example 11. Preparation of 3- (l-ethyl-propyliden) methyl ester) - hydrazine hydroxy acid.
    The experiment was carried out as described in Example 9, with the difference that 34.4 g (0.4 mol) of diethyl ketone was used as the starting compound. 57.15 g of the expected compound are obtained in the form of white crystals. Yield 90.4%. M.p. 66-67 C (after recrystallization from benzene).
    Example 12. Preparation of 3- (3-ethoxy-4-hydroxybenzylidene) -hydrazinugolic acid methyl ester.
    The test was carried out as described in Example 45 of Re 9, with the difference that 41.6 g (0.25 mol) 3-ethoxy-4-hydroxy-benzaldehyde was used as the starting compound. 56.3 g of the expected compound are obtained in the form of white crystals. . O Yield 94.6%. M.p. 172-173 ° C.
    Example 13: Preparation of 3- (1-ethyl-pentylidene) -hydrazinugoic acid methyl ester. 55
    The experiment was carried out as described in Example 9, with the difference that 34.25-g (0.3 mol) of ethyl- (n-butyl) ketone was used as the starting compound. 35.4 g of the expected compound are obtained. Yield 63.4%. M.p. 67-68 ° C.
    Example 14. Obtaining methyl ester of H- (cyclopentylidene) -hydrazuinogolic acid.
    The test was carried out as described in Example 1, with the difference that 33.6 g (0.3 mol) of cyclopentanone was used as the starting compound. The target compound in the form of white crystals is obtained in the amount of 49.25 g. The yield is 89.1%. M.p. 75 ° C.
    Note e- p. 15. Preparation of methyl 3 - (((L-ethyl) -p-hydroxy-benzylidene) -hydrazuinolic acid.
    The experiment was carried out as described in Example 1, with the difference that 37.54 g (0.25 mol) of p-hydroxy-pyrophenone was used as the starting compound. 43.8 g of the expected compound are obtained in the form of white crystals. The yield is 78.85%. M.p. 167 ° C.
    Example 16. Obtaining methyl ester of 3- (cyclododecdenedine) -hydrazinuganic acid.
    The experiment was carried out as described in Example 9, with the difference that 45.6 g (0.25 mol) of cyclododecanone was used as the starting compound. The target compound is obtained in the form of white crystals in the amount of 52.5 g. The yield is 83.2%. M.p. 141-142 p.
    Example 17. The preparation of methyl. Of the ester of 3- (cyclohexen 1-methyl) -hydr. Of acidic acid,
    To a solution of 11.2 g (0.1 mol) of cyclohexanecarbonal and 100 ml of methanol are first added 2 ml of acetic acid and then 9.0 g (0.1 mol) of the methyl carbonate. The reaction mixture is heated to reflux for 2 hours, then clarified, filtered and the filtrate is evaporated under reduced pressure. 15.6 g of the expected compound are obtained in the form of B. crystals. The yield is 84.8%. M.p. 103 ° C.
    Example 18. Preparation of methyl 3- (4-hydroxy-3-n-benzylidene) -hydrazinogolic acid.
    The experiment was carried out as described in example 3, with the difference that using 33.4 g (0.2 mol) of 4-hydroxy-3-nitro benzaldehyde as the starting compound. 41.65 g of the expected compound are obtained. The yield is 87.1%. . M.p. PZ-Pb S.
    Example 19. Preparation of methyl 3- (2-nitro-benzylidene) -hydrazine acid sour-x.
    The experiment was carried out as described in Example 9, with the difference that 30.2 g (0.2 mol) of 2-nitro-benzaldehyde was used as the starting material of the starting compound. 36.85 g of the desired compound are obtained in the form of yellowish crystals. Yield 82.6%. M.p. 152 ° С Ш
    Example 20. Preparation of 3- (4,5-dimethoxy-2-nitrobenzylidene) -1 1 -srazinugolic acid methyl ester.
    specified
    The test was carried out as described in f5. Mp. . measure 9, with the difference that 52.8 g (0.25 mol) of 2-nitro-4,5-dimethoxy-benzaldehyde is used as the starting compound. Get 57.6 g
    (92.4%) indicated in the title of dineni. M.p. .
    Example 25. Methyl ester of 3- (2-cyclohexane cyclohexylidene) carbazic acid.
    35.66 g (0.2 mol) of 2-cyclohexane cyclohexanone are dissolved in 250 m of methanol and 18 g (0.2 m of methyl carbazate and 3 ml of acetic acid) are added. After 2 h, they are clarified by evaporation and the resulting oil is separated. After the suspension in gasoline, 46.4 g (87.2%) in the title of the compound are obtained.
    Example 26. Methyl ether (2,4-dichlorobenzlidene) carbazic acid.
    Starting from 43.75 g (0.25 mol)
    target compound. Yield 81.5%. Yellow 20 2,4-dichlorobenzaldehyde and 22.5 g
    This product melts at 230-231 C.
    Example 21. Preparation of 3- (3-chloro-5-nitro-benzylidene) -hydrazinugoic acid methyl ester.
    The experiment was carried out as described in Example 3, with the difference that 3-chloro-5-nitro-benzaldehyde was used as the starting compound.
    Example 22: Preparation of methyl (0.25 mol) methylcarbazate as described in Example 1. 53.2 g (86.2%) of the title compound are obtained. M.p. 156-157 ° C.
    Example 27. Methyl 3- (3 4-dichlorobenzylidene) -carbazic acid ester.
    Starting from 43.75 g (0.25 mol) of 3,4-dichlorobenzaldehyde and 22.5 g
    of 3- (o-ethyl) -p-chloro-benzyl-30 (0.25 mol) methylcarbazate and the preparation of) -carboxylic acid. 57.25 g (92.7%) of the ester as described in in example 1 with the difference that as the starting compound is used
    35
    p-chloro-propiophenone.
    Example 23. Methyl ether. 3- (o4-cyclopropyl-4-methoxy) -benzydiene-carbazic acid.
    To a solution of 17.6 g (0.1 mol) of cyclopropyl-4-methoxyphenyl ketone in 100 ml of methanol was added 3 ml of acetic acid and then another 9.0 g (0.1 mol) of methyl carbazate.
    The reaction mixture is boiled for 5 hours, then clarified and filtered while hot. The filtrate is evaporated under vacuum, treated with 10 ml of ether to the separated, white crystals are filtered off. Get
    the compound “m.p. 154-155 C.
    EXAMPLE 28 Methyl ester of 3- (2-chloro-6-fluorobenzylidene) -carbazine acid.
    Outcome of 47.65 g (0.3 mol) of 2-chloro-6-fluorobenzaldehyde and 27 g (0.3 mol) of methyl carbazate, as described in Example 1, and 45 g of 40 (65.2%) indicated in compound name. M.p. 152-153 p.
    Compound efficacy
    formula (T), contributing to an increase in weight gain of animals is proved by 45 the following experiments.
    A. Pigs were used as test animals. For each test, six groups of animals were used. and each experiment was repeated with each group of animals three times.
    18.3 g (73.7%) of the compound indicated —50 11/11 with G T of feeding of the experimental group of pigs
    in the title. M.p., S. used food containing 50 mg / kg
    Example 24. Methyl ether "to
    (4 chloro-3-nitrobenzylidene) -carbacid.
    Out of 18.55 g (0.1 mol) of 4-chloro-3-nitrobenzaldehyde and 9 g (0.1 mol) of methyl carbazate, and as described in Example 1, 23.8 g are obtained.
    tested compounds. The feeding of animals was carried out under the same conditions, 55 and all: the groups of animals were fed with the same amount of food of the same composition. The comparative group received feed in the same amount, but with flavomycin content.
    specified
    M.p. .
    (92.4%) of the title compound. M.p. .
    Example 25. Methyl ester of 3- (2-cyclohexane cyclohexylidene) - carbazic acid.
    35.66 g (0.2 mol) of 2-cyclohexyl-cyclohexanone are dissolved in 250 ml of methanol and 18 g (0.2 mol of methyl carbazate and 3 ml of acetic acid) are added. After 2 h, clarify, evaporate and recover from the resulting oil white crystals are obtained. After suspension in gasoline, 46.4 g (87.2%) are obtained in the title compound.
    M.p. .
    Example 26. Methyl ether (2,4-dichlorobenzlidene) carbazic acid.
    Starting from 43.75 g (0.25 mol)
    (0.25 mol) of methyl carbazate as described in Example 1., and 53.2 g (86.2%) of the title compound are obtained. M.p. 156-157 ° C.
    Example 27. Methyl 3- (3 4-dichlorobenzylidene) -carbazic acid ester.
    Starting from 43.75 g (0.25 mol) of 3,4-dichlorobenzaldehyde and 22.5 g
    the compound “m.p. 154-155 C.
    EXAMPLE 28 Methyl ester of 3- (2-chloro-6-fluorobenzylidene) -carbazine acid.
    Outputs from 47.65 g (0.3 mol) of 2-chloro-6-fluorobenzaldehyde and 27 g (0.3 mol) of methyl carbazate, as described in Example 1, and 45 g (65.2%) of the title are obtained. compounds. M.p. 152-153 p.
    Compound efficacy
    formula (T), contributing to an increase in weight gain of animals is proved by the following experiments.
    A. Pigs were used as test animals. For each test, groups of animals were used. and each experiment was repeated with each group of animals three times.
    l fed with an experienced group of pigs
      "To
    tested compounds. Fattening animals was carried out under the same conditions and all: the groups of animals were fed the same amount of food of the same composition. The comparative group received feed in the same amount, but with flavomycin content.
    The control group received feed in the same amount, but without the test compound.
    A 5 weight gain was recorded daily and the daily average weight gain in weight percent was calculated using the following formula:
    Average daily weight gain
    in an experienced group.
    Average daily weight gain
    in the control group
    fO
    X 100
    The amount of feed fed to the respective experimental group was divided by the weight gain achieved in this experiment, and the criterion thus obtained was assigned to a criterion calculated similarly for the control rpynnbf. This value is the amount of feed, which in the relevant experimental group gives an increase in weight of 1 kg, counting on the amount of feed, which in the control group gives an increase in weight of 1 kg, in weight percent.
    The results are shown in table 1.
    Following the example:
    6
    21
    22 flavomitsin
    Carbadox (structural
    analog)
    eight
    Table 1
    463 345
    336
    82 95
    100,,.
    i B. Experience, described in paragraph A, was carried out with a group of pigs of 50 mt each. The period of fattening 60 days. The dose of the test compound is 50 mg / kg. The results were compared with the results of experiments obtained with feeds containing flavomycin. Results obtained with flavomycin were taken as 100%.
    The results are presented in table 2.
    table 2
    2.23
    96.2
    91299503
    The increase in pig growth was investigated according to the test procedure A „-
    The results are presented in table 3.5.
    Table 3
    Table 3 contains the results obtained from - on three individuals of male chant on the beds. All data are female (sheep) and three females with average values from the results, gender (sheep).
    10 Continuation of tab. 3
    8 9 13 14 16 17 19 10 11 7
    20 arbadoks
    108.5
    118
    109
    105
    114
    107.5
    109
    106
    104
    105.5
    105
    103
    94
    84
    95
    96
    92
    89.5
    92
    96
    93
    87
    93
    97
    The action, which increases the weight gain, was also studied on chickens. The data in Table 4 show the average value of the measurements carried out each time on 6 animals.
    Table 4
    From the results of the experiments of Table 5, it can be seen that the animals, which were fattened with the use of new derivatives of hydrazugolic acid in accordance with the VII with the invention, showed a significantly higher weight gain than animals of the control and comparative groups. At the same time, the same weight gain can be achieved with a significantly smaller amount of feed, which indicates a significantly better implementation of feed (digestibility).
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of obtaining derivatives of hydrazinone acid of the general formula
    R, N - NH - COORj,
    Editor N. Margolin
    Compiled by L. Joffe
    Tehred L. Serdyukova Proofreader A. Obruchar
    Order 905/63 Circulation 372 Subscription
    VNISh State Committee of the USSR
    for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5
    Production and printing company, Uzhgorod, st. Project, 4
    Table 5
    25
    thirty
    35
    40
    where R, is cycloalkylidene Cg-C, g, indanylidene or a group of formulas; D -
    RI
    wherein A is a phenyl group which may be substituted by one or more substituents selected from halogen, nitro, amino, hydroxy lower alkoxy groups or A is indolyl, lower alkyl, cyclohexyl;
    RJ is hydrogen, lower alkyl, alkyl
    15
     C, - C alkyl, characterized in that the carbonyl compound of general formula R, 0, where it has the indicated meaning, is reacted with methyl carbazate, followed by isolation of the desired product.
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    引用文献:
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    优先权:
    申请号 | 申请日 | 专利标题
    HU821381A|HU190795B|1982-05-04|1982-05-04|Process for producing carbazinic derivatives and compositions containing them for increasing weight yield|
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