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US 9,045,403 B2Granted
Geranyl geranyl acetone (GGA) derivatives and compositions thereof
AssigneeCoyote Pharmaceuticals, Inc.
InventorsHiroaki Serizawa, Ankush B. Argade, Akash Datwani, Natalie Spencer, Yonghua Pan, Florian Ermini
Life of this patent
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Abstract
This invention relates to geranylgeranyl acetone (GGA) derivatives and the use of GGA, its isomers, and GGA derivatives in methods for inhibiting neural death, increasing neural activity, increasing axon growth and cell viability, and increasing the survival rate of subjects administered the GGA or GGA derivatives.
Claims8
A compound of Formula (I):
- or pharmaceutically acceptable salt thereof, wherein
- n1 is 1 or 2;
- Q1 is —(C═O)—, —(C═S)—, or —S(O2)—;
- Q2 is —NR7R8;
- each R1 and R2 are independently C1-C6 alkyl, or R1 and R2 together with the carbon atom they are attached to form a C5-C7 cycloalkyl ring optionally substituted with 1-3 C1-C6 alkyl groups;
- each of R3, R4, and R5 independently are C1-C6 alkyl;
- R6 is:
- C1-C6 alkyl, optionally substituted with —CO2H or an ester thereof, C1-C6 alkoxy, oxo, —OH, —CR═CR2, —C≡CR, C3-C10 cycloalkyl, C3-C8 heterocyclyl, C6-C10 aryl, C2-C10heteroaryl, wherein each R independently is hydrogen or C1-C6 alkyl;
- C3-C10 cycloalkyl;
- C3-C8 heterocyclyl;
- C6-C10 aryl;
- or
- C2-C10 heteroaryl, provided that when n1 is 2, and one of R7 and R8 is hydrogen, R6 excludes C2-C10 heteroaryl
- wherein each cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with 1-3 alkyl groups;
- —CF3, 1-3 halo;
- 1-3 nitro groups;
- 1-3 C1-C6 alkoxy groups;
- —CO-phenyl;
- or —NR18R19;
- each R7 and R8 are independently hydrogen or defined as R6, provided that if n1 is 1 and one of R7 and R8 is hydrogen, the other excludes hydrogen
- each R18 and R19 independently is hydrogen;
- C1-C6 alkyl, optionally substituted with —CO2H or an ester thereof, C1-C6 alkoxy, oxo, —CR═CR2, —C≡CR, C3-C10 cycloalkyl, C3-C8 heterocyclyl, C6-C10 aryl, or C2-C10 heteroaryl, wherein each R independently is hydrogen or C1-C6 alkyl;
- C3-C10 cycloalkyl;
- C3-C8 heterocyclyl;
- C6-C10 aryl;
- or C2-C10 heteroaryl;
- wherein each cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally substituted with 1-3 alkyl groups, optionally substituted with 1-3 halo, or where R18 and R19 together with the nitrogen atom they are attached to form a 5-7 membered heterocycle.
24 more elements
A compound selected from the group consisting of:
- 7a
- 7b
- 7c
- 7d
- 7e
- 7f
- 7g
- 7h
- 7i
- 7j
- 7k
- 7l
- 7m
- 7n
- 7o
- 7p
- 7q
- 7r
- 7s
- 7t
- 7u
- 7v
- 7w
- 7x
- 7y
- 7z
- 7aa
- 8a
- 8b
- 8c
- 8d
- 8e
- 8f
- 8g
- 8h
- 8i
- 8j
- 8k
- 8l
- 8m
- 8n
- 8o
- 9a
- 9b
- 9c
- 9d
- 9e
- 9f
- 9g
- 9h
- 9i
- 9j
- 9k
- 10a
- 10b
- 10c
- 10d
- 10e
- 10f
- 10g
- 10h
- 10i
- 10j
- 10k
- 10l
- 10m
- 38a
- 38b
- 39
- 40a
- 40b
- 41
- 42
- 43
- or a pharmaceutically acceptable salt thereof.
72 more elements
Dependencies are inferred from the claim text.