Therapeutic compounds

Patent metadata

Field	Value
Publication number	US-10745366-B2
Application number	US-201716327284-A
Country	US
Kind code	B2
Filing date	Aug 24, 2017
Priority date	Aug 25, 2016
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

The invention provides compounds having the general formula I: and pharmaceutically acceptable salts thereof, wherein the variables R 1 , R 2 , R 3 , R 4 , subscipt m and n, have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

First claim

What is claimed is:

1. A compound of formula I:

or a pharmaceutically acceptable salt thereof, wherein:
R 1 is C 12-20 alkyl, C 12-20 alkenyl or C 12-20 alkynyl, and wherein the C 12-20 alkyl, C 12-20 alkenyl and C 12-20 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —OR a , —SR a , —NR a R b , oxo, —NO 2 and —CN;
R 2 is methyl
each R 3 is independently selected from the group consisting of —F, —Cl, —Br, —I, —OH, —OR a , —SR a , —NR a R b , —CN, C 1-4 alkyl, C 2-4 alkenyl and C 2-4 alkynyl, and wherein the C 1-4 alkyl, C 2-4 alkenyl and C 2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —OR a , —SR a , —NR a R b , oxo, —NO 2 and —CN;
each R a is independently selected from the group consisting of —F, —C 1 , —Br, —I, —OR a , —SR a , —NR a R b , —NO 2 , —CN, C 1-4 alkyl, C 2-4 alkenyl and C 2-4 alkynyl, and wherein the C 1-4 alkyl, C 2-4 alkenyl and C 2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —OR, —SR a , —NR a R b , oxo, —NO 2 and —CN;
each R 3 is independently hydrogen or C 1-4 alkyl;
each R b is independently hydrogen or C 1-4 alkyl;
the subscript m is 0, 1, 2 or 3; and
the subscript n is 0, 1, 2, or 3.

2. The compound of claim 1 that is a compound of formula Ia:

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , wherein R 1 is n-pentadecyl.

4. The compound of claim 1 , that is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition comprising a compound of formula (I) as described in claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

6. A method to prepare a compound of formula I or a pharmaceutically acceptable salt thereof, as described in claim 1 , comprising converting a corresponding compound of formula II or a salt thereof to the compound of formula I or the pharmaceutically acceptable salt thereof:

wherein:
R 5 is C 1-10 alkyl that is optionally substituted with one or more groups independently, selected from —F, —Cl, —Br, —I, —OR a , —SR a , oxo, —NO 2 and —CN; and
R 6 is hydrogen or C 1-6 alkyl that is optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —OR a , —SR a , —NR a R b , oxo, —NO 2 and —CN.

7. A pharmaceutical composition comprising the compound of claim 4 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

Assignees

• Univ Arizona State
• Arizon Board Of Regents On Behalf Of Arizona State Univ

Inventors

• Hecht Sidney
• Khdour Omar
• Chowdhury Sandipan Roy
• Visavadiya Nishant P

Classifications

• C07D279/14

  condensed with carbocyclic rings or ring systems · CPC title

• A61K31/5415

  ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam · CPC title

• C07D279/18 Primary

  [b, e]-condensed with two six-membered rings · CPC title

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• 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