# US 10,370,370 B2 · Aminobenzisoxazole compounds as agonists of α7-nicotinic acetylcholine receptors

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- Number: US 10,370,370 B2
- Document ID: US10370370B2
- Status: Granted
- Kind: B2
- Application number: 15/736,235
- Filed: 2016-06-09
- Published: 2018-05-17
- Granted: 2019-08-06
- Earliest claimed: 2015-06-10
- Assignees: Axovant Sciences GmbH
- Applicants: Forum Pharmaceuticals, Inc.
- Inventors: Raksha Acharya; Duane A. Burnett; Matthew Gregory Bursavich; Andrew Simon Cook; Bryce Alden Harrison; Andrew J. McRiner
- Web page: https://patentgrep.com/patent/US10370370B2

## CPC

- C07D 453/02: containing not further condensed quinuclidine ring systems
- A61P 25/00: Drugs for disorders of the nervous system
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to novel aminobenzisoxazole compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of Alpha7-nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

## Claims

### Claim 1

A compound represented by Formula (Ia) or Formula (Ib):
wherein:
R1, R2, R3, and R4 independently represent —H, -D, halogen radical, —CN, an unbranched C1-C4-alkyl radical, a branched C3-C4-alkyl radical, a C3-C6-cycloalkyl radical, an unbranched —OC1-C4-alkyl, a branched or cyclic —OC3-C4-alkyl, —N(R5)(R6), —(CO)N(R5)(R6), —NR5(CO)(R6), —SO2C1-C4-alkyl, —SO2N(R5)(R6), —(CH2)mSO2C1-C4-alkyl, —(CH2)mSO2N(R5)(R6), —N(R5)SO2C1-C4-alkyl, an aryl radical, or a heteroaryl radical; wherein the alkyl portion of the unbranched C1-C4-alkyl radical, the branched C3-C4-alkyl radical, the C3-C6-cycloalkyl radical, the unbranched —OC1-C4-alkyl, the branched or cyclic —OC3-C4-alkyl, the —SO2C1-C4-alkyl, the —(CH2)mSO2C1-C4-alkyl, or the —N(R5)SO2C1-C4-alkyl, may be independently substituted with up to 5 radical substituents comprising: -D, halogen radical, ═O, —OR5, —(CH2)mOR5, —N(R5)(R6), —NR5(CO)(R6), —(CH2)mN(R5)(R6), —SO2C1-C4-alkyl, —SO2N(R5)(R6), —(CH2)mSO2C1-C4-alkyl, —(CH2)mSO2N(R5)(R6), —N(R5)SO2C1-C4-alkyl, —(CO)(CH2)mR5, —(CO)N(R5)(R6), an unbranched C1-C6-alkyl radical, a branched C3-C6-alkyl radical, a C3-C6-cycloalkyl radical, a C1-C6-hydroxyalkyl radical, a C1-C2-haloalkyl radical, or —OC1-C2-haloalkyl radical; and wherein the aryl radical or the heteroaryl radical may be independently substituted with up to 5 radical substituents comprising: -D, halogen radical, —CN, —OR5, —(CH2)mOR5, —N(R5)(R6), —NR5(CO)(R6), —(CH2)mN(R5)(R6), —SO2C1-C4-alkyl, —SO2N(R5)(R6), —(CH2)mSO2C1-C4-alkyl, —(CH2)mSO2N(R5)(R6), —N(R5)SO2C1-C4-alkyl, —(CO)(CH2)mR5, —(CO)N(R5)(R6), an unbranched C1-C6-alkyl radical, a branched C3-C6-alkyl radical, a C3-C6-cycloalkyl radical, a C1-C6-hydroxyalkyl radical, a C1-C2-haloalkyl radical, or —OC1-C2-haloalkyl radical;
R5 and R6 independently represent —H; an unbranched C1-C6-alkyl radical, a branched C3-C6-alkyl radical; a C3-C6-cycloalkyl radical; or the N(R5)(R6) moiety forms a cycle, wherein R5 and R6 taken together represent a C2-C6-alkyl di-radical or a (3-6 membered)-heteroalkyl di-radical; wherein the (3-6 membered)-heteroalkyl di-radical comprises at least one ring atom selected from the group consisting of oxygen, nitrogen, and sulfur, with the proviso that when the at least one ring atom is nitrogen, the nitrogen is independently substituted with —H, an unbranched C1-C4-alkyl radical, a branched C3-C4-alkyl radical, a C3-C4-cycloalkyl radical, —(CO)-unbranched C1-C4-alkyl, —(CO)-branched C3-C4-alkyl, —(SO2)-unbranched C1-C4-alkyl, or —(SO2)-branched C3-C4-alkyl, and with the further proviso that when the at least one ring atom is sulfur, the sulfur may be independently substituted with 0 to 2 ═O; wherein the C2-C6-alkyl di-radical or the alkyl portion of said (3-6 membered)-heteroalkyl di-radical may be independently substituted with up to 5 radical substituents comprising: -D, halogen radical, ═O, an unbranched C1-C6-alkyl radical, or a branched C3-C6-alkyl radical; and
m independently represents an integer from 1 to 6;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 independently represents —H, -D, or halogen radical.

### Claim 3 (depends on 1)

The compound of claim 1, where R2 independently represents —H, -D, or halogen radical.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R3 independently represents —H, -D, —F, —Cl, —Br, —CN, an unbranched C1-C4-alkyl radical, a branched C3-C4-alkyl radical, a C3-C6-cycloalkyl radical, an unbranched —OC1-C4-alkyl, a branched or cyclic —OC3-C4-alkyl, —N(R5)(R6), —(CO)N(R5)(R6), —NR5(CO)(R6), —SO2C1-C4-alkyl, —SO2N(R5)(R6), —(CH2)mSO2C1-C4-alkyl, —(CH2)mSO2N(R5)(R6), —N(R5)SO2C1-C4-alkyl, an aryl radical, or a heteroaryl radical; wherein the alkyl portion of the unbranched C1-C4-alkyl radical, the branched C3-C4-alkyl radical, the C3-C6-cycloalkyl radical, the unbranched —OC1-C4-alkyl, the branched or cyclic —OC3-C4-alkyl, the —SO2C1-C4-alkyl, the —(CH2)mSO2C1-C4-alkyl, or the —N(R5)SO2C1-C4-alkyl, may be independently substituted with up to 5 radical substituents comprising: -D, —F, —Cl, —Br, ═O, —OR, —(CH2)mOR5, —N(R5)(R6), —NR5(CO)(R6), —(CH2)mN(R5)(R6), —SO2C1-C4-alkyl, —SO2N(R5)(R6), —(CH2)mSO2C1-C4-alkyl, —(CH2)mSO2N(R5)(R6), —N(R5)SO2C1-C4-alkyl, —(CO)(CH2)mR5, —(CO)N(R5)(R6), an unbranched C1-C6-alkyl radical, a branched C3-C6-alkyl radical, a C3-C6-cycloalkyl radical, a C1-C6-hydroxyalkyl radical, a C1-C2-haloalkyl radical, or —OC1-C2-haloalkyl radical; and wherein the aryl radical or the heteroaryl radical may be independently substituted with up to 5 radical substituents comprising: -D, —F, —Cl, —Br, —CN, —OR5, —(CH2)mOR5, —N(R5)(R6), —NR5(CO)(R6), —(CH2)mN(R5)(R6), —SO2C1-C4-alkyl, —SO2N(R5)(R6), —(CH2)mSO2C1-C4-alkyl, —(CH2)mSO2N(R5)(R6), —N(R5)SO2C1-C4-alkyl, —(CO)(CH2)mR5, —(CO)N(R5)(R6), an unbranched C1-C6-alkyl radical, a branched C3-C6-alkyl radical, a C3-C6-cycloalkyl radical, a C1-C6-hydroxyalkyl radical, a C1-C2-haloalkyl radical, or —OC1-C2-haloalkyl radical.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R3 independently represents —Cl, —CH3, or —OCH3.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R4 independently represents —H, -D, —F, —Cl, —Br, —CN, an unbranched C1-C4-alkyl radical, a branched C3-C4-alkyl radical, a C3-C6-cycloalkyl radical, an unbranched —OC1-C4-alkyl, a branched or cyclic —OC3-C4-alkyl, —N(R5)(R6), —(CO)N(R5)(R6), —NR5(CO)(R6), —SO2C1-C4-alkyl, —SO2N(R5)(R6), —(CH2)mSO2C1-C4-alkyl, —(CH2)mSO2N(R5)(R6), —N(R5)SO2C1-C4-alkyl, an aryl radical, or a heteroaryl radical; wherein the alkyl portion of the unbranched C1-C4-alkyl radical, the branched C3-C4-alkyl radical, the C3-C6-cycloalkyl radical, the unbranched —OC1-C4-alkyl, the branched or cyclic —OC3-C4-alkyl, the —SO2C1-C4-alkyl, the —(CH2)mSO2C1-C4-alkyl, or the —N(R5)SO2C1-C4-alkyl, may be independently substituted with up to 5 radical substituents comprising: -D, —F, —Cl, —Br, ═O, —OR5, —(CH2)mOR5, —N(R5)(R6), —NR5(CO)(R6), —(CH2)mN(R5)(R6), —SO2C1-C4-alkyl, —SO2N(R5)(R6), —(CH2)mSO2C1-C4-alkyl, —(CH2)mSO2N(R5)(R6), —N(R5)SO2C1-C4-alkyl, —(CO)(CH2)mR5, —(CO)N(R5)(R6), —OCF3, an unbranched C1-C6-alkyl radical, a branched C3-C6-alkyl radical, a C3-C6-cycloalkyl radical, a C1-C6-hydroxyalkyl radical, a C1-C2 haloalkyl radical, or —OC1-C2-haloalkyl radical; and wherein aryl radical or the heteroaryl radical may be independently substituted with up to 5 radical substituents comprising: -D, —F, —Cl, —Br, —CN, —OR5, —(CH2)mOR5, —N(R5)(R6), —NR5(CO)(R6), —(CH2)mN(R5)(R6), —SO2C1-C4-alkyl, —SO2N(R5)(R6), —(CH2)mSO2C1-C4-alkyl, —(CH2)mSO2N(R5)(R6), —N(R5)SO2C1-C4-alkyl, —(CO)(CH2)mR5, —(CO)N(R5)(R6), —OCF3, an unbranched C1-C6-alkyl radical, a branched C3-C6-alkyl radical, a C3-C6-cycloalkyl radical, a C1-C6-hydroxyalkyl radical, a C1-C2-haloalkyl radical, or —OC1-C2-haloalkyl radical.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R4 independently represents —H, -D, —F, —Cl, —CH3, —OCH3, —OCH2CH3, or —CF3.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound is a single enantiomer or a single diastereomer.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
7-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
5-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-cyclopropyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
N-(quinuclidin-3-yl)-6-(trifluoromethyl)benzo[d]isoxazol-3-amine;
6,7-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
4-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
3-(quinuclidin-3-ylamino)benzo[d]isoxazole-6-carbonitrile;
6-(methylsulfonyl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-(tert-butyl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
5,6-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
N-(quinuclidin-3-yl)-6-(trifluoromethoxy)benzo[d]isoxazol-3-amine;
7-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
5-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
4-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
7-fluoro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6,7-difluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
5-fluoro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-chloro-7-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-chloro-7-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-chloro-N-(quinuclidin-3-yl)-7-(trifluoromethyl)benzo[d]isoxazol-3-amine;
6-chloro-7-cyclopropyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
4-fluoro-6-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
4,6-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
7-fluoro-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
7-chloro-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
7-chloro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-isopropoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-ethoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-chloro-3-(quinuclidin-3-ylamino)benzo[d]isoxazole-7-carbonitrile;
7-chloro-6-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-(IH-pyrazol-I -yl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-(5-methyl-1,3,4-oxadiazol-2-yl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
7-methoxy-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-chloro-7-ethoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6,7-dimethyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-chloro-7-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
6-chloro-5-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine; and
6-bromo-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
and single enantiomers and pharmaceutically acceptable salts thereof.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
(R)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-7-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-7-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-5-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-5-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-cyclopropyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-cyclopropyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R) N-(quinuclidin-3-yl)-6-(trifluoromethyl)benzo[d]isoxazol-3-amine;
(S)-N-(quinuclidin-3-yl)-6-(trifluoromethyl)benzo[d]isoxazol-3-amine;
(R)-6,7-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6,7-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-4-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-4-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-3-(quinuclidin-3-ylamino)benzo[d]isoxazole-6-carbonitrile;
(S)-3-(quinuclidin-3-ylamino)benzo[d]isoxazole-6-carbonitrile;
(R)-6-(methylsulfonyl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-(methylsulfonyl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-(tert-butyl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-(tert-butyl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-5,6-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-5,6-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R) N-(quinuclidin-3-yl)-6-(trifluoromethoxy)benzo[d]isoxazol-3-amine;
(S)-N-(quinuclidin-3-yl)-6-(trifluoromethoxy)benzo[d]isoxazol-3-amine;
(R)-7-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-7-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-5-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-5-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-4-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-4-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-7-fluoro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-7-fluoro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6,7-difluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6,7-difluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-5-fluoro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-5-fluoro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-methy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-chloro-7-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-chloro-7-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-N-(quinuclidin-3-yl)-7-(trifluoromethyl)benzo[d]isoxazol-3-amine;
(S)-6-chloro-N-(quinuclidin-3-yl)-7-(trifluoromethyl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-cyclopropyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-chloro-7-cyclopropyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-4-fluoro-6-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-4-fluoro-6-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-4,6-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-4,6-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-7-fluoro-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-7-fluoro-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-7-chloro-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-7-chloro-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-7-chloro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-7-chloro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-isopropoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-isopropoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-ethoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-ethoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-3-(quinuclidin-3-ylamino)benzo[d]isoxazole-7-carbonitrile;
(S)-6-chloro-3-(quinuclidin-3-ylamino)benzo[d]isoxazole-7-carbonitrile;
(R)-7-chloro-6-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-7-chloro-6-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-(lH-pyrazol-l-yl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-(lH-pyrazol-1-yl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-(5-methyl-l,3,4-oxadiazol-2-yl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-(5-methyl-l,3,4-oxadiazol-2-yl)-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-7-methoxy-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-7-methoxy-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-ethoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-chloro-7-ethoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6,7-dimethyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6,7-dimethyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-chloro-7-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-5-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-chloro-5-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-bromo-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine; and
(S)-6-bromo-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
and pharmaceutically acceptable salts thereof.

### Claim 11 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
(R)-6-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(S)-6-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6,7-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-7-fluoro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-5-fluoro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-N-(quinuclidin-3-yl)-7-(trifluoromethyl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine; and
(R)-6-chloro-5-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
and pharmaceutically acceptable salts thereof.

### Claim 12 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
(R)-6-chloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6,7-dichloro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-7-fluoro-6-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-methyl-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-7-methoxy-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
(R)-6-chloro-N-(quinuclidin-3-yl)-7-(trifluoromethyl)benzo[d]isoxazol-3-amine; and
(R)-6-chloro-7-fluoro-N-(quinuclidin-3-yl)benzo[d]isoxazol-3-amine;
and pharmaceutically acceptable salts thereof.

### Claim 13 (depends on 1)

A pharmaceutical composition, comprising:
i) the compound, or pharmaceutically acceptable salt thereof, of claim 1; and
ii) at least one pharmaceutically acceptable carrier, excipient or diluent.