# US 4,391,826 A · Phenethanolamines, compositions containing the same, and method for effecting weight control

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- Number: US 4,391,826 A
- Document ID: US4391826A
- Status: Granted
- Kind: A
- Application number: 06/096,361
- Filed: 1979-11-21
- Granted: 1983-07-05
- Earliest claimed: 1978-07-03
- Assignees: Eli Lilly and Company
- Inventors: Jack Mills; Klaus K. Schmiegel; Walter N. Shaw
- Web page: https://patentgrep.com/patent/US4391826A

## CPC

- C07C 255/00: Carboxylic acid nitriles (cyanogen or compounds thereof C01C3/00)
- A61K 31/13: Amines {(A61K31/04 takes precedence)}
- C07C 29/147: of carboxylic acids or derivatives thereof
- C07C 51/487: by treatment giving rise to chemical modification (by chemisorption C07C51/47)
- C07C 229/38: having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C 243/38: with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C07D 303/04: containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
- C07B 2200/07: Optical isomers
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Optically active N-3-(4-substituted phenyl)propyl-.beta.-phenethanolamines are provided as well as pharmaceutical compositions containing such compounds. A method for effecting weight control in obese animals utilizing optically active phenethanolamines is disclosed. Novel intermediates useful in the preparation of optically active .beta.-phenethanolamines are provided.

## Claims

### Claim 1

A pharmaceutical formulation useful in the control of weight in obese animals comprising as active principle an amount effective for controlling weight of an optically active phenethanolamine of the formula ##STR11## wherein: R.sub.2 is hydrogen, methyl or ethyl;
R.sub.3 is aminocarbonyl or methylaminocarbonyl;
C is an asymmetric carbon atom having the R absolute stereochemical configuration;
C is an asymmetric carbon atom when R.sub.2 is methyl or ethyl, and when asymmetric is of the S absolute stereochemical configuration; and the non-toxic pharmaceutically acceptable acid addition salts thereof, in combination with a suitable pharmaceutical carrier therefor.

### Claim 2 (depends on 1)

The formulation of claim 1 wherein R.sub.2 is methyl.

### Claim 3 (depends on 2)

The formulation of claim 2 employing R,S-N-(2-phenyl-2-hydroxyethyl)-1-methyl-3(4-methylaminocarbonylphenyl)pro pylamine.

### Claim 4 (depends on 2)

The formulation of claim 2 wherein the active principle is R,S-N-(2-phenyl-2-hydroxyethyl)-1-methyl-3-(4-aminocarbonylphenyl)propylam ine.

### Claim 5 (depends on 1)

The formulation of claim 1 wherein R.sub.2 is hydrogen.

### Claim 6

A method for effecting weight control in an obese animal in need of treatment which comprises administering to such animal an amount effective for controlling weight of a compound of the formula ##STR12## wherein: R.sub.2 is hydrogen, methyl or ethyl;
R.sub.3 is aminocarbonyl or methylaminocarbonyl;
C is an assymetric carbon atom having the R absolute stereochemical configuration;
C is an asymmetric carbon atom when R.sub.2 is methyl or ethyl, and when asymmetric is of the S absolute stereochemical configuration; and the non-toxic pharmaceutically acceptable acid addition salts thereof.

### Claim 7 (depends on 3)

A method according to claim 3 wherein a compound is administered to a mature obese animal effect a weight loss.

### Claim 8 (depends on 6)

A method according to claim 6 wherein a compound is administered to an immature obese animal to prevent excessive weight gain.

### Claim 9 (depends on 6)

The method of claim 6 employing a compound wherein R.sub.2 is methyl or ethyl.

### Claim 10 (depends on 9)

The method of claim 9 wherein the active principle administered in R,S-N-(2-phenyl-2-hydroxyethyl)-1-methyl-3-(4-methylaminocarbonylphenyl)pr opylamine.

### Claim 11 (depends on 9)

The method according to claim 9 wherein the active principle administered is R,S-N-(2-phenyl-2-hydroxyethyl)-1-methyl-3-(4-aminocarbonylphenyl)propylam ine.

### Claim 12 (depends on 6)

The method of claim 6 employing a compound wherein R.sub.2 is hydrogen.

### Claim 13

A method for improving the leanness of meat in livestock animals comprising administering an effective amount of a compound of the formula ##STR13## wherein: R.sub.2 is hydrogen, methyl or ethyl;
R.sub.3 is aminocarbonyl or methylaminocarbonyl;
C is an asymmetric carbon atom having the R absolute stereochemical configuration;
C is an asymmetric carbon atom when R.sub.2 is methyl or ethyl, and when asymmetric is of the S absolute stereochemical configuration; and the non-toxic pharmaceutically acceptable acid addition salts thereof.

### Claim 14 (depends on 13)

The method of claim 13 wherein the animal species treated is swine.

### Claim 15 (depends on 13)

The method of claim 13 employing a compound wherein R.sub.2 is hydrogen.

### Claim 16 (depends on 15)

The method of claim 15 wherein the compound administered is dl-N-(2-phenyl-2-hydroxyethyl)-3-(4-methylaminocarbonylphenyl)propylamine.

### Claim 17 (depends on 15)

The method of claim 15 wherein the compound administered is dl-N-(2-phenyl-2-hydroxyethyl)-3-(4-aminocarbonylphenyl)propylamine.

### Claim 18 (depends on 13)

The method of claim 13 employing a compound wherein R.sub.2 is methyl or ethyl.

### Claim 19 (depends on 18)

The method of claim 18 wherein the compound administered is R,S-N-(2-phenyl-2-hydroxyethyl)-1-methyl-3-(4-aminocarbonylphenyl)propylam ine.

### Claim 20 (depends on 18)

The method of claim 18 wherein the compound administered is R,S-N-(2-phenyl-2-hydroxyethyl)-1-methyl-3-(4-methylaminocarbonylphenyl)pr opylamine.