Deuterated analogs of pridopidine useful as dopaminergic stabilizers

Patent metadata

Field	Value
Publication number	US-2016166559-A1
Application number	US-201514968522-A
Country	US
Kind code	A1
Filing date	Dec 14, 2015
Priority date	Sep 3, 2010
Publication date	Jun 16, 2016
Grant date	—

Abstract

In other aspects the invention relates to pharmaceutical compositions comprising a deuterated analog of Pridopidine of the invention, and to therapeutic applications of these analogs.

First claim

1 - 11 . (canceled)

12 . A pharmaceutical composition comprising a compound represented by Formula 1

or a pharmaceutically acceptable salt thereof, wherein
at least one of R 1 -R 23 represents deuterium (D); and
the remaining of R 1 -R 23 represent hydrogen (H);

wherein the abundance of molecules of the compound having deuterium at a position designated by the at least one of R 1 -R 23 is substantially greater than the natural abundance of deuterium at that position.

13 . The pharmaceutical composition of claim 12 , wherein
R 1 -R 2 represent deuterium (D); and all of R 3 -R 23 represent hydrogen (H).

14 . The pharmaceutical composition of claim 12 , wherein at least one of R 1 -R 7 represents deuterium (D); and
the remaining of R 1 -R 23 represent hydrogen (H).

15 . The pharmaceutical composition of claim 12 , wherein
all of R 1 -R 7 represent deuterium (D); and all of R 8 -R 23 represent hydrogen (H).

16 . The pharmaceutical composition of claim 12 , wherein
R 8 , R 9 , R 10 and R 11 represent deuterium (D); and all of R 1 -R 7 and R 12 -R 23 represent hydrogen (H).

17 . The pharmaceutical composition of claim 12 , wherein
R 12 represents deuterium (D); and all of R 1 -R 11 and R 13 -R 23 represent hydrogen (H).

18 . The pharmaceutical composition of claim 12 , wherein
R 17 -R 20 represent deuterium (D); and all of R 1 -R 16 and R 21 -R 23 represent hydrogen (H).

19 . The pharmaceutical composition of claim 12 , wherein the compound or the pharmaceutically acceptable salt thereof is 4-(3-Methanesulfonyl-phenyl)-1-propyl-d7-piperidine hydrochloride.

20 . The pharmaceutical composition of claim 12 , wherein the abundance of molecules of the compound having deuterium at a position designated by the at least one of R 1 -R 23 is at least 3,340 times greater than the natural abundance of deuterium at that position, at least 3,500 times greater than the natural abundance of deuterium at that position, at least 4,000 times greater than the natural abundance of deuterium at that position, at least 5,000 times greater than the natural abundance of deuterium at that position, at least 6,000 times greater than the natural abundance of deuterium at that position, at least 6,466.7 times greater than the natural abundance of deuterium at that position, or at least 6,633.3 times greater than the natural abundance of deuterium at that position.

21 . The pharmaceutical composition of claim 12 , comprising the pharmaceutically acceptable salt of the compound.

22 . A therapeutically effective amount of the pharmaceutical composition of claim 12 together with at least one pharmaceutically acceptable carrier, excipient or diluent.

23 . The pharmaceutical composition according to claim wherein
R 1 -R 2 represent deuterium (D); and all of R 3 -R 23 represent hydrogen (H).

24 . The pharmaceutical composition according to claim 22 , wherein
at least one of R 1 -R 7 represents deuterium (D); and the remaining of R 1 -R 23 represent hydrogen (H).

25 . The pharmaceutical composition according to claim 22 , wherein
all of R 1 -R 7 represent deuterium (D); and all of R 8 - R 23 represent hydrogen (H).

26 . The pharmaceutical composition according to claim 22 , wherein
R 8 , R 9 , R 10 and R 11 represent deuterium (D); and all of R 1 -R 7 and R 12 -R 23 represent hydrogen (H).

27 . The pharmaceutical composition according to claim 22 , wherein
R 12 represents deuterium (D); and all of R 1 -R 11 and R 13 -R 23 represent hydrogen (H).

28 . The pharmaceutical composition according to claim 22 , wherein
R 17 - R 20 represent deuterium (D); and all of R 1 -R 16 and R 21 -R 23 represent hydrogen (H).

29 . The pharmaceutical composition of claim 22 comprising the pharmaceutically acceptable salt of the compound.

30 . A method of treating, preventing, or alleviating a symptom of, a dopamine mediated disorder in a living animal which comprises administering to the living animal a therapeutically effective amount of the pharmaceutical composition of claim 12 .

31 . A method of treating, or alleviating a symptom of, Huntington's Disease in a living animal which comprises administering to the living animal a therapeutically effective amount of the pharmaceutical composition of claim 12 .

Assignees

• Sonesson Clas
• Teva Pharmaceuticals Int Gmbh

Inventors

• Sonesson Clas

Classifications

• A61P25/28

  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 title

• A61P25/00

  Drugs for disorders of the nervous system · CPC title

• A61P25/14

  for treating abnormal movements, e.g. chorea, dyskinesia · CPC title

• A61K31/451 Primary

  having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine · CPC title

• C07B59/002

  Heterocyclic compounds · CPC title