Camsylate salt

Patent metadata

Field	Value
Publication number	US-10548882-B2
Application number	US-201313916754-A
Country	US
Kind code	B2
Filing date	Jun 13, 2013
Priority date	Jun 21, 2012
Publication date	Feb 4, 2020
Grant date	Feb 4, 2020

Abstract

A camsylate salt of (1r,1′R,4R)-4-methoxy-5″-methyl-6′-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3′H-dispiro[cyclohexane-1,2′-inden-1′2′-imidazole]-4″-amine, pharmaceutical compositions containing the salt and therapeutic uses of the salt for treating Aβ-related pathologies such as Alzheimer's Disease, Down's syndrome, β-amyloid angiopathy and conditions such as dementia including dementia of mixed vascular and degenerative origin, pre-senile dementia, senile dementia and dementia associated with Parkinson's disease, progressive supranuclear palsy or cortical basal degeneration.

First claim

The invention claimed is:

1. A camsylate salt of (1r,1′R,4R)-4-methoxy-5″-methyl-6′-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3′H-dispiro[cyclohexane-1,2′-indene-1′,2″-imidazol]-4″-amine:

2. A crystalline camsylate salt of (1r,1′R,4R)-4-methoxy-5″-methyl-6′-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3′H-dispiro[cyclohexane-1,2′-indene-1′,2″-imidazol]-4″-amine:

characterized in that said crystalline camsylate salt has an X-ray powder diffraction (XRPD) pattern, exhibiting substantially the following very strong, strong and medium peaks with d-values:

Corrected
d-spacing
Relative

Angles
(Å)
intensity

5.66
15.60
vs

7.72
11.44
m

11.30
7.83
m

12.35
7.16
s

12.83
6.89
m

15.24
5.81
m

15.47
5.72
m

17.17
5.16
m

18.13
4.89
m

19.71
4.50
m

20.77
4.27
m

21.12
4.20
m

23.63
3.76
m

24.50
3.63
m

26.18
3.40
m

26.54
3.36
m

34.30
2.61
m

36.78
2.44
m.

3. A crystalline camsylate salt of (1r,1′R,4R)-4-methoxy-5″-methyl-6′-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3′H-dispiro[cyclohexane-1,2′-indene-1′,2″-imidazol]-4″-amine:

characterized in that said crystalline camsylate salt has an X-ray powder diffraction pattern essentially as shown in FIG. 1 .

4. A pharmaceutical composition comprising as active ingredient a therapeutically effective amount of a salt according to claim 1 , in association with at least one pharmaceutically acceptable excipient, carrier or diluent.

5. A method of treating an Aβ-related pathology in a patient in need thereof, comprising administering to said patient a therapeutically effective amount of a salt according to claim 1 , wherein said Aβ-related pathology is Down's syndrome, a β-amyloid angiopathy, cerebral amyloid angiopathy, MCI (“mild cognitive impairment”), Alzheimer's Disease, neurodegeneration associated with Alzheimer's disease, dementia of degenerative origin, pre-senile dementia, senile dementia, dementia associated with Parkinson's disease, or cortical basal degeneration.

6. A method of treating Alzheimer's Disease in a patient in need thereof, comprising administering to said patient a therapeutically effective amount of a salt according to claim 1 .

7. A crystalline camsylate salt of (1r,1′R,4R)-4-methoxy-5″-methyl-6′-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3′H-dispiro[cyclohexane-1,2′-indene-1′,2″-imidazol]-4″-amine:

Assignees

• Astrazeneca Ab

Inventors

• Bohlin Martin Hans
• Stewart Craig Robert

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

• A61P25/16

  Anti-Parkinson drugs · CPC title

• C07D401/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• A61P25/00

  Drugs for disorders of the nervous system · CPC title

• C07D235/02 Primary

  condensed with carbocyclic rings or ring systems · CPC title