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United States Patent (19) 11 Patent Number: 4,754,047 Kiernan Et Al

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United States Patent (19) 11 Patent Number: 4,754,047 Kiernan Et Al United States Patent (19) 11 Patent Number: 4,754,047 Kiernan et al. (45) Date of Patent: Jun. 28, 1988 54 PHENYLETHANOLAMINEDERIVATIVES 2,938,921 5/1960 Mills .................................... 564/363 AND ACID ADDITION SALTS THEREOF 3,236,892 2/1966 Petracek ............... ... 564/363 FOR ENHANCING THE GROWTH RATE OF 3,344,188 9/1967 Wollweber et al. ... 564/363 3,348,999 10/1967 Woroch et al........... ... 424/272 MEAT-PRODUCING ANIMALS AND/OR 3,536,712 10/1970 Keck et al........ ... 564/363 IMPROVING THE EFFICIENCY OF FEED 3,574,211 4/1971 Keck et al. ....... ... 564/363 UTILIZATION THEREBY 3,657,319 4/1972 Kaiser et al. .......................... 560/29 3,759,979 9/1973 Beregi et al...... ... 564/164 (75. Inventors: Jane A. Kiernan, Kendall Park; 3,869,492 3/1975 Biel et al. .............................. 560/29 Pamela K. Baker, Hopewell, both of 3,870,715 3/1975 Hansl............ ... 562/442 N.J. 3,896,141 7/1975 Keck et al. ....... ... 564/363 73) Assignee: American Cyanamid Company, 3,954,871 5/1976 Buu-Hoi et al. ..... ... 562/432 4,063,025 12/1977 Murakami et al. .. 560/29 Stamford, Conn. 4,119,710 10/1978 Engelhardt et al. ... 55.8/422 (21) Appl. No.: 679,714 4,163,060 7/1979 Hartog et al. ............ ... 564/165 4,179,442 12/1979 Köllensperger et al............ 424/272 22 Filed: Dec. 10, 1984 4,186,129 1/1980 Huth et al. .......................... 424/272 4,188,323 2/1980 Pestellini et al. ................... 424/272 Related U.S. Application Data 4,211,794 7/1980 Kraska ................................ 564/363 4,214,001 7/1980 Engelhardt et al................... 560/29 60 Division of Ser. No. 528,765, Sep. 2, 1982, Pat. No. 4,238,506 12/1980 Stach .................... ... 562/442 4,501,751, which is a division of Ser. No. 219,054, Dec. 22, 1980, Pat. No. 4,404,222, which is a continuation-in 4,338,455 7/1982 Zupan ................................... 560/29 part of Ser. No. 181,254, Aug. 25, 1980, abandoned, 4,385,066 5/1983 Ainsworth et al. ... 562/451 which is a continuation-in-part of Ser. No. 143,069, 4,396,627 8/1983 Ainsworth et al.................. 562/451 Apr. 24, 1980, abandoned, which is a continuation-in FOREIGN PATENT DOCUMENTS part of Ser. No. 066,908, Aug. 16, 1979, abandoned. 2935902 2/1981 Fed. Rep. of Germany ...... 424/272 51) Int. Cl.' .................. C07C 101/00; CO7C 149/40; 41-6462 4/1966 Japan ................................... 564/340 C07C 103/28; C07C 125/06 7504917 10/1975 Netherlands ........................ 564/164 52 U.S. C. ...................................... 558/422; 560/19, 560/29; 560/32; 560/33; 562/426; 562/432; Primary Examiner-Douglas W. Robinson 562/442; 562/451; 564/164; 564/165; 564/363; Attorney, Agent, or Firm-Alice C. Brennan - 564/340; 564/365 57 ABSTRACT 58 Field of Search ............... 514/522, 523, 524, 529, 514/533,540, 538,562,563, 567,570,571, 619, There is provided a method for enhancing the growth 626, 613, 653,654; 560/19, 29, 32,33; 562/426, rate of meat-producing animals and/or improving the 432, 442, 451; 564/164, 165, 363, 340, 365; efficiency of feed utilization thereby, which involves, 558/422 orally or parenterally, administering to said animals a growth-enhancing amount of a phenylethanolamine (56) References Cited compound or the acid addition salt thereof. U.S. PATENT DOCUMENTS 2,754,000 8/1953 Fauran et al. ....................... 424/272 10 Claims, No Drawings 4,754,047 1. 2 -continued PHENYLETHANOLAMINEDERVATIVES AND (Ia) ACD ADDITION SALTS THEREOF FOR ENHANCING THE GROWTH RATE OF -CH MEAT-PRODUCING ANIMALS AND/OR 5 CH N-R3; and IMPROVING THE EFFICIENCY OF FEED O CHR7 UTLZATION THEREBY This is a division of application Ser. No. 528,765, filed Sept. 2, 1982, which issued on Feb. 26, 1985, as U.S. Pat. 10 (Ib) No. 4,501,751, which is a division of application Ser. No. 219,054, filed Dec. 22, 1980, which issued on Sept. 13, 1983, as U.S. Pat. No. 4,404,222, which is a continua tion-in-part of application Ser. No. 181,254, filed Aug. 25, 1980, now abandoned, which is a continuation-in 15 part of application Ser. No. 143,069, filed Apr. 24, 1980, now abandoned, which in turn is a continuation-in-part wherein, of application Ser. No. 066,908, filed Aug. 16, 1979, X is hydrogen, halogen or -CN; now abandoned. Y is hydrogen, NR8R9 or NHCORs; Z is hydrogen, halogen, OH, CN, CF3, COOR1, SUMMARY OF THE INVENTION CONH2, C1-C4 alkyl, C1-C4 alkoxy, NO2, C1-C4-dialk Substitution products of 1-(amino-dihalophenyl)-2- ylaminomethyl or hydroxymethyl; aminoethanes, and the acid addition salts thereof, are R1 is hydrogen or C1-C4 alkyl; disclosed in U.S. Pat. No. 3,536,712, issued Oct. 27, R2 is hydrogen, C1-C6 alkyl, C3-C4 alkenyl, C2-C5 1970. Specifically, methods for the synthesis of said 25 alkanoyl or compounds are disclosed as useful for enhancing the blood circulation, and as bronchodilators, analgesics, sedatives, antipyretics, antiphlogistics and antitussives in warm-blooded animals. However, only the analgesic 30 utility is examplified. The preparation of other related CO; 1-(amino-dihalophenyl)-2-aminoethanols and their de rivatives are disclosed in Japanese Kokai No. 7783,619 (Chemical Abstracts, 87,201061r), German Offen R3 is hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, me legungsschrift No. 2,804,625 (1979), German Offen 35 thoxypropyl, C3-C4 alkenyl, phenyl, 2-hydroxyethyl, legungsschrift No. 2,157,040 (1973), German Offen a,a-dimethylphenethyl, benzyl, 3-phenylpropyl or 3-(4- legungsshrift No. 2,261,914 (1974), Europen Patent carbomethoxyphenyl)propyl; and when R2 and R3 are Application No. 8,715 (1980), Netherlands Patent Ap taken together with the nitrogen to which they are plication No. 7,303,612 (1973). These applications dis attached, they represent morpholino or N'-C1-C4 alkyl close uses selected from analgesics, broncholytic, anti 40 piperazino; inflammatory, uterine, spasmolytic, 6-blocking activi R4 is hydrogen, OH, OR6 or SR11; ties, antispasmolytic acitvity on cross-striped muscle R5 is hydrogen, C1-C4 alkyl, C1-C4 alkoxy, structure, for tocology, reducing blood pressure by peripheral vasodilation and mobilizing body fat, and for R10 R10 treating allergies. There is no indication or suggestion in 45 any of these disclosures that said compounds are effec tive as growth-promoting agents for meat-producing animals, such as poultry, cattle, sheep or the like; nor is ()-- ()- O N(R)2; there any suggestion that said compounds improve the efficiency of feed utilization by said meat-producing 50 R6 is C1-C6 alkyl, C2-C5 alkanoyl, animals. In accordance with the process of the invention, it has been found that the growth rate of meat-producing RO RO RO animals such as chickens, turkeys, rabbits, sheep, goats and cattle, including calves, can be increased and/or the 55 efficiency of feed utilization thereby measurably im proved by the oral or parenteral administration to said ()- ()- ()-- animals of an effective amount of a compound selected from the group consisting of: R7 is hydrogen, C1-C4 alkyl or phenyl; 60 R8 is hydrogen, C1-C4 alkyl or C3-C4 alkenyl; R9 is hydrogen, C1-C6 alkyl, C4-C6 cycloalkyl, X (I) C3-C4 alkenyl, or benzyl; and when R8 and R9 are taken together with the nitrogen to which they are attached, they represent pyrrolidino; 65 R10 is chloro, dichloro, methyl, dimethyl, methoxy, R. R. dimethoxy or nitro; R11 is C1-C6 alkyl, phenyl or benzyl; with the provi sos that when R3 is phenyl, 2-hydroxyethyl, a,c-dime 4,754,047 3. 4. thylphenethyl, C3-C6 cycloalkyl, benzyl, methoxypro butylamino)methyl-3,5-dichlorobenzyl alcohol hydro pyl, 3-phenylpropyl, or 3-(4-carbomethoxyphenyl)pro chloride, 4-amino-N-tert-butyl-3,5-dichloro-3-methox pyl, R2 is hydrogen; and when R3 is hydroxyethyl, R4 is yphenethylamine hydrochloride, a-Ctert-butylamino)- hydroxyl and the compound is (); and when Ré is al methyl-3,5-dichloro-4-methylamino-benzyl alcohol; kanoyl or a-(tert-butylamino)methyl-3,5-dichloro-4-iso propylaminobenzyl alcohol; a-(tert-butylamino)me thyl-3,5-dichloro-4-ethylaminobenzyl alcohol; 5-2- (tert-butylamino)-1-hydroxyethyl-3-chloroan thranilonitrile; N-tert-butyl-3,5-dichloro-g-methoxy-4- CO, O methylaminophenethylamine; 3-chloro-5-2-(tert butylamino)-1-hydroxyethyllanthranilonitrile; R2 and R3 are substituents other than hydrogen, except Although it is evident from the above discussion that when R3 is an alkyl or substituted alkyl group which certain compounds represented by formula I above are contains a tertiary carbon attached to nitrogen; and 15 described in the literature, many compounds repre when Y is hydrogen, X and Z are halogen, and R2 is sented by formula I are new and unobvious. The novel hydrogen, C3-C5 alkanoyl or and unobvious compounds of the present invention are represented by the structure of formula I, R10 20 X (I) CO, R3 is isopropyl, 2-butyl, or t-butyl; and when R8 is 25 C1-C4 alkyl or C3-C4 alkenyl, R9 is hydrogen, C1-C4 alkyl or C3-C4 alkenyl; and when Z is OH, X and Y are wherein hydrogen; and that at least one of X, Y, and Z repre sents a substituent other than hydrogen; and when X is X is hydrogen, halogen or -CN; -CN, Z is -CN; and when Z is hydroxymethyl, R4 is 30 Y is hydrogen, NR8R9 or NHCOR5; - OH; and when Z is a group other than halogen, Y is Z is halogen, -CN, CF3, COOR, CONH2, C1-C4 NR8R9 or NHCOR5; and when R5 is NOR)2, R4 is OH; alkyl, C1-C4 alkoxy, NO2 or C1-C4 dialk racemic mixtures of the above-identified compounds ylaminomethyl; and the optically active isomers, and non-toxic, pharma R1 is hydrogen or C1-C4 alkyl; cologically acceptable acid addition salts thereof.
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