Inhibitors of cognitive decline
AssigneeCognition Therapeutics, Inc.
InventorsGilbert M. Rishton, Susan Catalano
Life of this patent
Estimating the term…
Abstract
Compounds that are central nervous system drug candidates for the treatment of cognitive decline and, more particularly, Alzheimer's disease are provided. Methods of treating, inhibiting, and/or abatement of cognitive decline and/or Alzheimer's disease with a compound or pharmaceutically acceptable salt of the invention are also provided. Also provided are methods of preparing the compounds/compositions of the invention.
Claims41
A compound of Formula I-0:
- or pharmaceutically acceptable salt thereof, wherein:
- is a single bond or a double bond;
- R1 is H, CH3, CF3, F, Cl, Br, or —OCF3;
- R2 is H, C1-6 alkyl, C1-6 haloalkyl, C3-7 cycloalkyl, or C6-10 aryl, wherein each of the C1-6 alkyl, C1-6 haloalkyl, C3-7 cycloalkyl, or C6-10 aryl is substituted by 0, 1, 2, 3, 4, or 5 substituents each independently selected from OH, amino, halo, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, and C1-6 haloalkoxy;
- R3 is NR3aR3b;
- R3a is H, C1-6 alkyl, C1-6 haloalkyl, cycloalkylalkyl, C3-7 cycloalkyl, arylalkyl, or C6-10 aryl, wherein each of the C1-6 alkyl, C1-6 haloalkyl, cycloalkylalkyl, C3-7 cycloalkyl, or C6-10 aryl is substituted by 0, 1, 2, 3, 4, or 5 substituents each independently selected from OH, amino, halo, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, and C1-6 haloalkoxy;
- R3b is H, C1-6 alkyl, C1-6 haloalkyl, cycloalkylalkyl, cycloalkylalkyl, C3-7 cycloalkyl, arylalkyl, or C6-10 aryl, wherein each of the C1-6 alkyl, C1-6 haloalkyl, cycloalkylalkyl, C3-7 cycloalkyl, arylalkyl, or C6-10 aryl is substituted by 0, 1, 2, 3, 4, or 5 substituents each independently selected from OH, amino, halo, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, and C1-6 haloalkoxy;
- or R3a and R3b together with the N atom to which they are attached form a 4-, 5-, 6- or 7-membered heterocycloalkyl group that is substituted with 0, 1, 2, 3, 4, or 5 substituents each independently selected from OH, amino, halo, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, and heterocycloalkyl;
- and
- R4 is H, C1-6 alkyl, C1-6 haloalkyl, C3-7 cycloalkyl, or C6-10 aryl, wherein each of the C1-6 alkyl, C1-6 haloalkyl, C3-7 cycloalkyl, or C6-10 aryl is substituted by 0, 1, 2, 3, 4, or 5 substituents each independently selected from OH, amino, halo, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, and C1-6 haloalkoxy.
A compound selected from:
- N-isobutyl-2-methyl-6-p-tolylhept-2-en-4-amine;
- and
- (6S)—N-isobutyl-2-methyl-6-p-tolylhept-2-en-4-amine;
- or pharmaceutically acceptable salt thereof.
A compound or pharmaceutically acceptable salt thereof formed by a process comprising:
- (a) reacting a turmeric oil with 4-isobutylamine under reactive amination condition to produce a crude product, wherein the ratio of the ginger oil to 4-isobutylamine about 3.4:1 by weight;
- and
- (b) isolating a composition comprising at least 80%, 85%, 90%, or 95% by weight of a compound or a pharmaceutically acceptable salt thereof,
- wherein:
- the compound has an analytical mass spectrum peak of [M+H+] at about 274.3.
A compound or pharmaceutically acceptable salt thereof formed by a process comprising:
- (a) reacting a turmeric oil with 4-isobutylamine under reactive amination condition to produce a crude product, wherein the ratio of the ginger oil to 4-isobutylamine about 3.4:1 by weight;
- and
- (b) isolating a composition comprising at least 80%, by weight of a compound or a pharmaceutically acceptable salt thereof,
- wherein:
- the compound has an analytical mass spectrum peak of [M+H+] at about 276.3.
34-39. (canceled)
46-50. (canceled)
Dependencies are inferred from the claim text.