Growth promotion

• US 5,643,967 A
• Filed: 03/18/1993
• Issued: 07/01/1997
• Est. Priority Date: 01/31/1983
• Status: Expired due to Fees

• Current Assignee: Eli Lilly and Company
• Original Assignee: Eli Lilly and Company
• Inventors: Anderson, David B., Tuttle, Ronald R., Schmiegel, Klaus K., Veenhuizen, Edward L.
• Primary Examiner(s): Weddington, Kevin E.
• Application Number:
  US08/037,789
• Time in Patent Office: 1,566 Days
• Field of Search: 514/653
• US Class Current: 514/653
• CPC Class Codes: A23K 20/111 Aromatic compounds
• CPC Class Codes: A61K 31/135 having aromatic rings , e.g. ketamine, nortriptyline methadone A61K31/137
• CPC Class Codes: C07C 215/30 containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
• CPC Class Codes: C07C 217/62 linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
• CPC Class Codes: C07C 51/347 by reactions not involving formation of carboxyl groups
• CPC Class Codes: C07C 51/487 by treatment giving rise to chemical modification by chemisorption C07C51/47
• CPC Class Codes: C07C 59/68 the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring

Abstract

β-Phenethanolamines are effective in promoting growth and improving feed efficiency and leanness in animals.

Claims

1. A method for promoting the growth of a domesticated warm blooded animal other than a ruminant, swine, or poultry, which comprises administering to the animal an effective amount of 1-(4-hydroxyphenyl)-2-(1-methyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

2. The method of claim 1 wherein the animal is one raised for human meat consumption.

3. A method for improving the feed efficiency of a domesticated warm blooded animal other than a ruminant, swine, or poultry, which comprises administering to the animal an effective amount of 1-(4-hydroxyphenyl)-2-(1-methyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

4. The method of claim 3 wherein the animal is one raised for human meat consumption.

5. A method for promoting the growth of a domesticated warm blooded animal which comprises administering to the animal an effective amount of a compound having the formula ##STR4## wherein R¹ is hydrogen, hydroxy, or methoxy;

R² is hydrogen or fluoro;

R³ is hydrogen or C₁ -C₂ alkyl;

R⁴ is hydrogen or methyl;

R⁵ is hydrogen, fluoro, nitro, hydroxy, SO₂ CH₃ or CONH₂ ;

provided that R¹ is hydrogen only when R⁵ is nitro or SO₂ CH₃, or an acid addition salt thereof;

excluding the compounds 1-(4-hydroxyphenyl)-2-(1-methyl-3-(4-hydroxyphenyl)propylamino)ethanol and 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-phenylpropylamino)ethanol and their acid addition salts.

6. The method of claim 5 employing 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

7. The method of claim 5 wherein the animal is one raised for human meat consumption.

8. The method of claim 7 wherein the animal is a ruminant.

9. The method of claim 7 wherein the animal is a swine.

10. The method of claim 7 wherein the animal is poultry.

11. The method of claim 10 employing 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

12. The method of claim 11 wherein the poultry is a turkey.

13. The method of claim 11 wherein the poultry is a chicken.

14. A method for improving the efficiency of feed utilization by a domesticated warm blooded animal which comprises administering an effective amount of a compound of the formula ##STR5## wherein:

R¹ is hydrogen, hydroxy, or methoxy;

R² is hydrogen or fluoro;

R³ is hydrogen or C_l -C₂ alkyl;

R⁴ is hydrogen or methyl;

R⁵ is hydrogen, fluoro, nitro, hydroxy, SO₂ CH₃ or CONH₂ ;

provided that R¹ is hydrogen only when R⁵ is nitro or SO₂ CH₃, or an acid addition salt thereof;

excluding the compounds 1-(4-hydroxyphenyl)-2-(1-methyl-3-(4-hydroxyphenyl)propylamino)ethanol and 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-phenylpropylamino)ethanol and their acid addition salts.

15. The method of claim 14 employing 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

16. The method of claim 14 wherein the animal is one raised for human meat consumption.

17. The method of claim 16 wherein the animal is a ruminant.

18. The method of claim 16 wherein the animal is a swine.

19. The method of claim 16 wherein the animal is poultry.

20. The method of claim 19 employing 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

21. The method of claim 20 wherein the poultry is a turkey.

22. The method of claim 20 wherein the poultry is a chicken.

23. A method for improving leanness in a domesticated warm blooded animal which comprises administering to the animal an effective amount of a compound of the formula ##STR6## wherein:

R¹ is hydrogen, hydroxy, or methoxy;

R² is hydrogen or fluoro;

R³ is hydrogen or C₁ -C₂ alkyl;

R⁴ is hydrogen or methyl;

R⁵ is hydrogen, fluoro, nitro, hydroxy, SO₂ CH₃ or CONH₂ ;

provided that R¹ is hydrogen only when R⁵ is nitro or SO₂ CH₃, or an acid addition salt thereof;

excluding the compounds 1-(4-hydroxyphenyl)-2-(1-methyl-3-(4-hydroxyphenyl)propylamino)ethanol and 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-phenylpropylamino)ethanol and their acid addition salts.

24. The method of claim 23 employing 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

25. The method of claim 23 wherein the animal is one raised for human meat consumption.

26. The method of claim 25 wherein the animal is a ruminant.

27. The method of claim 25 wherein the animal is a swine.

28. The method of claim 25 wherein the animal is poultry.

29. The method of claim 28 employing 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt.

30. The method of claim 23 wherein the animal is a dog.

31. The method of claim 23 wherein the animal is a cat.

32. An animal feedstuff comprising a β

-phenethanolamine of the formula ##STR7## wherein;

R¹ is hydrogen, hydroxy, or methoxy;

R² is hydrogen or fluoro;

R³ is hydrogen or C₁ -C₂ alkyl;

R⁴ is hydrogen or methyl;

R⁵ is hydrogen, fluoro, nitro, hydroxy, SO₂ CH₃ or CONH₂ ;

provided that R¹ is hydrogen only when R⁵ is nitro or SO₂ CH₃, or an acid addition salt thereof;

excluding the compound 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-phenylpropylamino)ethanol and its acid addition salts.

33. The feedstuff of claim 32 wherein the β

-phenethanolamine is 1-(4-hydroxyphenyl)-2-(1-methyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

34. The feedstuff of claim 32 wherein the β

-phenethanolamine is 1-(4-hydroxyphenyl)-2-(1,1-dimethyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

35. The feedstuff of claim 32 containing from about 5 to about 95 percent by weight of the β

-phenethanolamine.

36. The feedstuff of claim 35 comprising corncob meal as a carrier.

37. The feedstuff of claim 36 wherein the β

-phenethanolamine is 1-(4-hydroxyphenyl)-2-(1-methyl-3-(4-hydroxyphenyl)propylamino)ethanol or an acid addition salt thereof.

38. The feedstuff of claim 37 wherein the β

-phenethanolamine is 1-(4-hydroxyphenyl)-2-(1-methyl-3-(4-hydroxyphenyl)propylamino)ethanol hydrochloride.