Aminocarbonylcarbamate compounds

Patent metadata

Field	Value
Publication number	US-10314808-B2
Application number	US-201715805293-A
Country	US
Kind code	B2
Filing date	Nov 7, 2017
Priority date	Feb 28, 2014
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

The present disclosure provides a compound represented by Formula (I) and a pharmaceutically acceptable salt which are effective as a dopamine reuptake inhibitor and a method of using the compound:

wherein X is independently halo, alkyl, alkoxy or nitro; m is 0, 1, 2, 3 or 4; n is 1 or 2; R 1 and R 2 are independently H— or alkyl; R 3 is H—, alkyl or aralkyl; and R 4 is H— or aryl.

First claim

What is claimed is:

1. A combination of a compound of Formula I or pharmaceutically acceptable salt thereof and a therapeutic agent selected from the group consisting of adderall, concerta, dexedrine, focalin, metadate, methylin, ritalin, vyvanse, daytrana, and quillivant,

wherein
X is independently halo, alkyl, alkoxy or nitro;
m is 0, 1, 2, 3 or 4
n is 1 or 2;
R 1 and R 2 are independently H— or alkyl;
R 3 is H—, alkyl or aralkyl; and
R 4 is H— or aryl,
wherein at least one of R 1 , R 2 , R 3 and R 4 is not H—.

2. The combination of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
2-(isopropylamino)-3-phenylpropyl (aminocarbonyl)carbamate;
2-(dimethylamino)-3-phenylpropyl (aminocarbonyl)carbamate;
2-(methylamino)-3-phenylpropyl (aminocarbonyl)carbamate; and
2-amino-3-phenylpropyl (anilinocarbonyl)carbamate.

3. The combination of claim 1 , wherein the compound of Formula I is selected from the group consisting of:
(2R)-2-(isopropylamino)-3-phenylpropyl (aminocarbonyl)carbamate;
(2R)-2-(dimethylamino)-3-phenylpropyl (aminocarbonyl)carbamate;
(2R)-2-(methylamino)-3-phenylpropyl (aminocarbonyl)carbamate; and
(2R)-2-amino-3-phenylpropyl (anilinocarbonyl)carbamate.

4. The combination of claim 1 , formulated for oral administration.

5. A method for inhibiting dopamine reuptake comprising:
administrating to a subject in need thereof a therapeutically effective amount of the combination of claim 1 .

6. The method of claim 5 , which is for the treatment of a central nervous system disease.

7. The method of claim 5 , which is for the treatment of attention deficit hyperactivity disorder (ADHD).

8. A combination of a compound selected from a group consisting of:
2-amino-3-(2-chlorophenyl)propyl (aminocarbonyl)carbamate;
2-amino-3-(2,4-dichlorophenyl)propyl (aminocarbonyl)carbamate;
2-amino-3-(3,4-dichlorophenyl)propyl (aminocarbonyl)carbamate;
2-amino-3-(4-chlorophenyl)propyl (aminocarbonyl)carbamate;
2-amino-3-(3-chlorophenyl)propyl (aminocarbonyl)carbamate;
2-amino-3-(4-nitrophenyl)propyl (aminocarbonyl)carbamate;
2-amino-3-(4-tert-butylphenyl)propyl (aminocarbonyl)carbamate;
2-amino-3-(2-fluorophenyl)propyl (aminocarbonyl)carbamate;
(2R)-2-amino-3-(2-chlorophenyl)propyl (aminocarbonyl)carbamate;
(2R)-2-amino-3-(2,4-dichlorophenyl)propyl (aminocarbonyl)carbamate; and
(2R)-2-amino-3-(3,4-dichlorophenyl)propyl (aminocarbonyl)carbamate or pharmaceutically acceptable salt thereof and a therapeutic agent selected from the group consisting of adderall, concerta, dexedrine, focalin, metadate, methylin, ritalin, vyvanse, daytrana, and quillivant.

9. The combination of claim 8 formulated for oral administration.

10. A method for inhibiting dopamine reuptake comprising:
administrating to a subject in need thereof a therapeutically effective amount of the combination of claim 8 .

11. The method of claim 10 , which is for the treatment of a central nervous system disease.

12. The method of claim 10 , which is for the treatment of attention deficit hyperactivity disorder (ADHD).

Assignees

• Sk Biopharmaceuticals Co Ltd

Inventors

• Kang Young-Soon
• Chung Jin-Yong
• Maeng Cheol-Young
• Yi Han-Ju
• Lee Ki-Ho
• Heo Joon
• Chae Eun-Hee
• Shin Yu-Jin

Classifications

• A61K9/0053 Primary

  Mouth and digestive tract, i.e. intraoral and peroral administration · CPC title

• A61K31/325 Primary

  Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof (thiurams A61K31/145) · CPC title

• A61P25/00

  Drugs for disorders of the nervous system · CPC title

• C07C275/60 Primary

  Y being an oxygen atom, e.g. allophanic acids · CPC title

• A61K31/27 Primary

  of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine · CPC title