• 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 beta -Phenethanolamine of the following formula is effective in promoting growth and improving feed efficiency and leanness in animals: <CHEM> or an acid addition salt thereof. m
    公开号:SU1523043A3
    申请号:SU843692327
    申请日:1984-01-30
    公开日:1989-11-15
    发明作者:Беннет Андерсон Дэвид；Курт Шмигел Клаус；Ли Винхуизен Эдвард
    申请人:Эли Лилли Энд Компани (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to animal husbandry and can be used for about 1 feed of farm animals and poultry.
    The aim of the invention is to increase the increase in body weight and improve the quality of meat.
    This goal is achieved by using 1-4 (hydroxyphenyl) -2 -2-methyl-3- (4-hydroxyphenyl) propylamino-ethanol (I) or 1- (4-hydroxyphenyl) -2- as a growth-enhancing additive. -methyl-3- (4-hydroxyphenyl) propyl amino ethanol hydrochloride (s), or 1- (4-hydroxyphenyl), 1 dimethyl-3-phenylpropylamino ethanol succinate (ill) or
    1- (2-fluorophenyl), 1-dimethyl-3- (4-aminocarbonylphenyl) -propyl-MHHoJ-ethanol (IV). Compound (D) can be obtained by reacting styrene oxide with 3-phenylproduct amine derivatives, for example, by reacting 2-fluorostyrene oxide with an approximately equimolar amount of an amine such as 1-methyl-3- (4-nitrophenyl) - propyl amine, in a non-reactive solvent (ethanol, methanol, n-propanol, dioxane). The reaction is carried out at a temperature of from 50 to 120 ° C, after 6-10 hours it. usually finished. The finished product is evaporated at a low temperature to remove the solvent.
    cl
    yu so
    00

    s
    The purification was carried out by recrystallization, chromatography with acid-base extraction.
    An alternative method of obtaining compounds5 used in the present invention as growth-stimulating additives includes the interaction of the almond derivative
    acids with the derivative of 3 phenylpropyl
    amine, resulting in an amide, which, when subsequently dissolved, yields a compound of the above formula Formula: A phenylpropyl amine derivative, for example, 1-methyl-3- (3-fluorophenyl-1nyl) -propylamine, interacts with an acylating agent such as oxo-substituted mandelic acid, or (preferably) with a mineral acid in the presence of the usual | NO pentidating reagent; - races as a benzene or H, I-dimethylformamide, and complete in 2-48 hours (if it is carried out at a temperature of from 30 to), the readmission product is amyl, which is easily isolated by simply filtering the reaction mixture, followed by removing the reaction solvent o. The resulting amide is reduced by reacting with a reducing agent, for example diborane or a similar compound, to give compound I
    Another method of synthesis is the interaction of phenethanolamine with phenylethyl ketone, resulting in the formation of a Schiff base, which, when reduced, gives the compound used in the present invention.
    Phenethanolamine, for example, 2-hydroxy-2- (4-hydroxyphenyl) ethylamine, can react with a ketone such as methyl 2- (4-hydroxyphenyl) methyl ketone to form the corresponding imine, which, for example, can be reduced % palladium on carbon is 1- (4-hydroxyphenyl) -2-l-methyl-3- (4-hydroxyphenyl) propamino ethanol o
    In a preferred embodiment of the present invention, a mixture of optical isomers is used. For example, 1- (4-hydroxyphenyl) -2-p-met.yl-3- (4-hydroxyphenyl) propylamino ethanol is obtained from a racemic mixture of starting materials — d51-1- methyl 3- (4 hydroxyphenyl) propyl
    5 0 o c
    Q
    5 Q
    five
    amine and 1,1-4-oxystyrene oxide, thus obtaining a mixture of all four possible optical isomers of the product “
    The mixture of optical isomers can be used without subsequent separation of the isomers.
    Since / 3 -phenethanolamines inherently have a basic character, they can form. salts with a variety of organic and inorganic acids.
    Preferred salts used in the proposed method are 1-4 (hydroxyphenyl) -2-O-methyl-3-4-hydroxyphenyl propylamino ethanol hydrochloride or 1-f4-oxyphenyl} -2-lf l-dimethyl-3- phenyl-propylene-e-etha-nol succinate.
    These compounds are preferably administered orally with food in an amount of 0.1-0.5 mg / kg of life. They are mixed with fillers such as corn, soybean flour, alfalfa flour, rice flour, soybean meal, bone for flour, reed molasses, sodium chloride, urea, and Top.
    Compounds can be administered in the form of granules, salt cubes, and also added directly to drinking water.
    The invention is illustrated by the following examples.
    Example 1, a solution of 32.8 g (0.1 mol) of methyl-2- (4-hydroxy-1) ethyl ketone with 42.6 g (0.2 mol) of 1- (4-hydroxyphenyl) -2-aminoethanol in 380 ml of ethanol containing 3.8 g of p of percentage palladium supported on carbon is stirred for 16 hours at 60 ° C under a hydrogen atmosphere at a pressure of 378.93 kPa. The reaction mixture is filtered, the filtrate is diluted with 350 ml of water. The aqueous mixture is concentrated to a volume of 400 ml, washed with dichloromethane, acidified with 50 ml of concentrated hydrochloric acid. After exposure, at room temperature for two hours the acidic aqueous mixture is filtered, the filter residue is washed with 40 ml of ice. water and dried at 50 ° C in vacuum
    47 g of 1- (4-hydroxyphensh1) -2-l-methyl-3- (4-hydroxyphenyl) propylamino-ethanol hydrochloride (compound II) are obtained. Melting point 124-129 ° C.
    PRI me R 2o Premix for chickens containing (in% by weight):
    1- (4-hydroxyphenyl) -2-C1.1 dimethyl-3-phenylpropylamino ethanol
    succinate
    Ground Corn
    Sodium chloride
    Example 3. Premix for gum: x animals, containing,%
    1- (2-fluorophenyl) -2- 1-dimethyl-3- - (4-aminocarbonyl
    phenyl) propylamino ethanol
    Ground yellow25, 0 74.0 1.0,
    that corn alfalfa flour
    was obtained with less food intake "
    Example The efficacy of compound II was also tested in turkeys for broilers aged 21 days, orally daily with the main feed administered compound II up to the age of 56 days, Q the results are shown in table 2
    The premix contains vitamins: 3000 mg of vitamin A, 900 mg of vitamin D, 40 mg E, 0.7 mg of vitamin K, 1000 mg of choline, 70 mg of niadine, 15 4 mg of pantothenic acid, 4 mg of riboflavin, 100 μg of vitamin B, 100 mcg of biotin and 125 mg of ethoxy per 60.0 kg of ready-made nnjsfj, 10.0 Premix contains the following mic30, 0
    PRI me R 4 Premix for pigs, 20 roelements, mg: manganese 75; zinc
    containing,% by weight: 1- (4-hydroxyphenyl) -2- -metsh1-3 (4-hydroxyphenyl) propyl-aMHHoJ ethanol hydrochloride Soybean cake Oil product
    50; iron 0.25; iodine 1 per 1 kg of the basic diet.
    The animals were analyzed for weight gain and the efficiency of food digestion. 25 The results (change in weight of broilers) are presented in Table.
    Example 7. Tabl4 illustrates the results obtained when feeding the castrated ram compound 10, 0 88.0 2.0
    The above ingredients are mixed until homogeneous, obtaining a dry ZO-NII II,
    bulk premix that can be added - EXAMPLE 8 Action of I- (4-Oxiphenyl) -2- -methyl-3- (4-hydroxyphenyl) nponHnaMKHol ethanol (compound 1) and 1-С2-fluorophenyl-2 - (1,1-dimethylZ-37, - - (4-aminocarbonylphenyl) propylamino etatt chto I G ff TTTJf TTTTiTi (if tt about gtt
    l in the main food of animals so that the diet contains 20 ml of the active ingredient
    The proposed growth-promoting supplements may be administered in combination with other compounds, for example, an antibiotic. Such combinations include from 1 to 2 parts by weight. of the proposed compound and from 1 to 10 parts by weight. associated Q component.
    Froze A group of pigs received a basic diet and additionally compound II (as in Example O in the amount of 20 g / t in combination with the antibiotic tylosin in the amount of 40 g / t.
    The results are summarized in Table I. ,, As can be seen from the table, treatment with compound 11 produces carcass with a lower fat content and a higher content of congenital tissue.
    45
    nola (compound PO was evaluated by the result of a 42-day study on pigs.
    The results are presented in table 5
    The proposed supplements stimulate the growth of animals, improve the efficiency of food digestion and improve the composition of ca sao
    Formula inventions
    The method of feeding of farm animals and poultry, including the use in the diet of growth-stimulating, 50 dormant additives, which, in order to increase the calculated amount of muscle
    growth of live weight and improving the quality of mac; 1-4 (hydroxyphenyl) - parts of the carcass are used as a growth-promoting additive when treated with a combination of 55 2- | 1-methyl-3- (4-hydroxyphenyl) propipamytylosin plus compound II ethanol, or 1-4 (hydroxyphenyl) with that amount which was hemisyl-3- (4-hydroxyphenyl) propylamino ethanol hydrochloride or 1- (4-hydroxyphenyl), 1-dimethyl-3-phenyl-y) was treatment with tylosin alone and in control, however, this result
    50; iron 0.25; iodine 1 per 1 kg of the basic diet.
    The animals were analyzed for weight gain and the efficiency of food digestion. Results (change in weight of broilers) are presented in Table.
    Example 7. Tabl4 illustrates the results obtained when feeding the NII II compound to castrated rams,
    EXAMPLE 8 Action of I- (4-Oxiphenyl) -2- -methyl-3- (4-hydroxyphenyl) nponHnaMKHol-ethanol (Compound I) and 1-C2-Fluorophenyl-2- (1,1-Dimethyl) -37 4-aminocarbonylphenyl) propylamino etatt cgto IG ff TTTJf TTTTiTi (if tt o gtt
    nola (compound PO was evaluated by a 42-day study on pigs.
    The results are presented in table 5
    The proposed supplements stimulate the growth of animals, improve the efficiency of food digestion and improve the composition of ca sao
    Formula inventions
    A method for feeding farm animals and poultry, including the use of growth-stimulating additives in the diet, characterized in that, in order to increase weight gain and improve meat quality, 1-4 (hydroxyphenyl 2- | 1-methyl-3- (4-hydroxyphenyl) propypane but ethanol, or 1-4 (hydroxyphenyl) methyl 3- (4-hydroxyphenyl) propylamino ethanol hydrochloride or 1- (4-hydroxyphenyl), 1-dimethyl-3- phenyl-y) opi71523043 8
    Lenamino Zethanol succinate, or 1- (2-carbonylphenyl) -propylamino ethanol and phyhornyl-2-L 1 dimethyl-3 -. (4-amino- injected it in an amount of 0.1-0.4 mg / kg.
    Table 1
    Note, 1, Results are based on measurements.
    the fat layer in the 1st rib after the carcass is divided across the spine,
    2. In determining the digital data on the weight of the small part of the carcass, the regression equation was used 1.Animal Icience, 1977, 14: 8: 17,
    66, 40 60.2 1, 53 13.7
    4.0 36.2
    19.19. 173,952 2.50 22.65
    1.01 15.402 2.50 22.65 0.83 6.51 0.3 2.718
    Table 2
    O0.18616.678889

    400,17916,358,64
    800,21416,177,56
    Table5
    152304310
    Continuation of table 2
    Tab, Faces
    Table4
    权利要求:
    Claims (2)
    [1]
    Claim
    A method of feeding farm animals and poultry, including the use of growth-promoting additives in the diet, characterized in that, in order to increase the gain in live weight and improving meat quality, 1-4 (hydroxyphenyl) -2-f 1-methyl- is used as growth-promoting additives 3- (4-hydroxyphenyl) propylamino) ethanol, or 1-4 (hydroxyphenyl) -2- [Ϊmethyl-3- (4-hydroxyphenyl) propylamino) ethanol hydrochloride or 1- (4-hydroxyphenyl) -2- [1, 1-dimethyl-3-phenyl-propylene-amino '} ethanol succinate, or 1- (2 fluorophenyl-2- [1,1 dimethyl-3 -. (4-amino carbonylphenyl) propylamino] ethanol and e in an amount of 0.1-0.4 mg / kg.
    Table 1
    Result The control Tylosin Compound II Tylosin + + Compound II The average gain per day, kg 1, 63 1,64 1.36 1,50 The average food intake per day, kg 5.64 5.77 5.10 5.38. 3.46 3,51 3.77 3,59 Mascara Weight (lbs) 150.3 151.5 140.1 146.3 Fat Depth (jO-e rib) inch 0.96 0.96 0.80 0.85 Center area., Loin, inch 4.60 4.68 4.92 5.00 Calculated% of muscle 49.2 49.2 51,4 51,2 The calculated weight of the muscle, pound 65.3 76.5 74.1 76.8
    Note. 1, The results are based on measurements of the fat layer at the 1st rib after the carcass is divided across the spine <,
    [2]
    2. In determining the digital data on the weight of the muscle part of the carcass, the I.Animal regression equation was used
    Icience, 1977, 14: 8: 17,
    Table 2
    The composition of the main diet (control) By weight kg / t 1 2 3
    Ground yellow
    melted corn 66.40 60,2 Animal-plantfat 1,53 13.7 Corn flour(60%) 4.0 36,2 Soya flour (48%) 19.19 173,952 Fish flour 2,50 22.65 Secondary sourcalcium phosphate 1, 01 15,402 Feather flour 2,50 22.65 Shredded • vestnik 0.83 6.51 Salt 0.3 2,718
    Continuation of Table 2
    1 e 3 Premix:vitamin 0.50 4,53 trace elements 0.10 0,906 methionine 0.15 1.36 lysine 0.29 2.63
    Tab b, face II
    1585
    1613
    1550
    1669
    7.6
    9.5
    5.2
    13.3
    2,292
    2,298
    2,312
    2,221
    1.9
    1.6 1.0
    4.9
    Table4
    Group
    Weight change The average food intake per day, kg Efficiency of digestion Dose,Modo The average increase. per day, kg
    Control 0 0.186 16.67 8.89 Compound-- A 40 0.179 16.35 8.64 80 0.214 16.17 7.56
    Table5
    Group Dose Average Average pot Effectgrowth ribbing tivilityper day, cabbage soup per day assimilatekg kg food
    The control 1.60 (0.725), 4.7 2.98 UnitedI 20 1.60 (0.725) 4.26 (1.96) 2.66 Compound-IV IV 20 1.52 (0.69) 4.57 (2.08) 3.01
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US46258783A| true| 1983-01-31|1983-01-31|
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