Deuterium-enriched alkyl sulfonamides

• US 8,530,479 B2
• Filed: 08/09/2010
• Issued: 09/10/2013
• Est. Priority Date: 08/10/2009
• Status: Active Grant

• Current Assignee: Daljit Singh Dhanoa
• Original Assignee: Daljit Singh Dhanoa
• Inventors: Dhanoa, Daljit Singh
• Primary Examiner(s): VAJDA, KRISTIN ANN
• Application Number:
  US12/806,279
• Publication Number:
  US 20110034479A1
• Time in Patent Office: 1,128 Days
• Field of Search: 514/255.03, 544/393
• US Class Current: 514/255.03
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/06 Antimigraine agents
• CPC Class Codes: A61P 25/18 Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
• CPC Class Codes: A61P 25/22 Anxiolytics
• CPC Class Codes: A61P 25/24 Antidepressants
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: C07D 295/135 with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Abstract

The present invention is concerned with deuterium-enriched isobutyl and cyclohexylmethyl sulfonamides of formula I and II, and pharmaceutically acceptable salts and methods of use thereof for the treatment of general anxiety disorders, major depressive disorders, attention deficit disorders, attention deficit hyperactivity disorder, Alzheimer'"'"'s disease, frontotemporal dementia, cognitive impairment associated with age-related dementia, schizophrenia, migraine, sleep disorders, neurodegenerative diseases and obesity.

Claims

1. A deuterium-enriched compound of formula I and II, or the pharmaceutically acceptable salt thereof, wherein:

R₁-R₃₄ of formula I are independently selected from H and D;

R₁-R₃₈ of formula II are independently selected from H and D;

R₂₅ in both formula I and II is independently selected from H, D and CD₃;

2. A deuterium-enriched compound of claim 1 selected from the group consisting of:

Deuterated N-3-(Acetyl(d₃)amino(d₁)phenyl(d₃)-1-piperazinyl-4-n-butyl)-isobutyl(d₉)-sulfonamide(N-d₁), deuterium chloride (2DCl);

3. The deuterium enriched compound of claim 1, wherein the deuterium-enriched compound is

N-3-(Acetyl(d₃)amino(d₁)phenyl (d₃)-1-piperazinyl-4-n-butyl)-isobutyl(d₉)-sulfonamide (N-d₁), deuterium chloride (2DCl) salt,

4. The deuterium enriched compound of claim 1, wherein the deuterium-enriched compound is

N-3-(Acetyl(d₃)amino(d₁)phenyl (d₃)-1-piperazinyl-4-n-butyl) isobutyl(d₉)-N-methyl(d₃)sulfonamide, deuterium chloride (2DCl) salt,

5. The deuterium enriched compound of claim 1, wherein the deuterium-enriched compound is

N-3-(Acetyl(d₃)amino(d₁)phenyl (d₃)-1-piperazinyl-4-n-butyl)-cyclohexylmethyl(d₁₃)-sulfonamide (N-d₁), deuterium chloride (2DCl) salt,

6. The deuterium enriched compound of claim 1, wherein the deuterium-enriched compound is

N-3-(Acetyl(d₃)amino(d₁)phenyl (d₃)-1-piperazinyl-4-n-butyl)-cyclohexylmethyl(d₁₃)-N-methyl(d₃)-sulfonamide, deuterium chloride (2DCl) salt,

7. A deuterium enriched compound of claim 1, or the pharmaceutically acceptable salts thereof wherein a compound is selected from the group consisting of: