IP Library › Granted Patent US 12673944

Granted Patent B2

US 12673944 · App. 17/755,858 · Granted Jul 7, 2026

Compounds having inhibitory activity against glucosylceramide synthase or pharmaceutically acceptable salt thereof, processes for preparing the same, and pharmaceutical compositions comprising the same

Inventors: Dong-Hoon Kim (Suwon-si, KR); Jae-Eun Joo (Yongin-si, KR); Eui-Chul Lee (Yongin-si, KR); Tae-Dong Han (Yongin-si, KR); Seung-Yub Shin (Osan-si, KR); Sool-Ki Kwon (Yongin-si, KR)

Assignees: YUHAN CORPORATION; GREEN CROSS CORPORATION

C07D453/02 A61P3/00 C07D471/08 C07D519/00

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 12673944
App. No.: 17/755,858
Granted: Jul 7, 2026
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

Provided are a compound of Formula 1 having a chromane, isochromane, thiochromane, or tetrahydroquinoline moiety or pharmaceutically acceptable salt thereof, a process for the preparation thereof, a pharmaceutical composition comprising the same and a use thereof, wherein the compound having a chromane, isochromane, thiochromane, or tetrahydroquinoline moiety or pharmaceutically acceptable salt thereof has an inhibitory activity against glucosylceramide synthase (GCS), and therefore can be usefully applied for preventing or treating various diseases associated with GCS, such as Gaucher disease, Fabry disease, Tay-Sachs disease, Parkinson's disease, etc.:

Claims (423)

1 . A compound of Formula 1 or pharmaceutically acceptable salt thereof:

wherein,

L is —O—, —CO—, —CR 1 R 2 —, or —NR 3 —,

X is hydrogen; halogen; C 1 -C 6 alkyl; C 1 -C 6 alkyl substituted with 1 to 3 halogens; C 1 -C 6 alkoxy; or C 1 -C 6 alkoxy substituted with 1 to 3 halogens,

Y is —NR 3 —; —O—; or —S—,

P is —CR 4 R 5 —,

Q is —O— or —CR 4 R 5 —,

Z is —CR 6 —,

R 1 and R 2 are, independently of each other, hydrogen; halogen; C 1 -C 6 alkyl; C 3 -C 10 cycloalkyl; 3- to 12-membered heterocyclic; or C 1 -C 6 alkoxy; or R 1 and R 2 form C 3 -C 10 cycloalkyl together with the carbon atom to which they are attached,

R 3 is C 1 -C 6 alkyl,

R 4 and R 5 are, independently of each other, hydrogen; halogen; C 1 -C 6 alkyl; C 3 -C 10 cycloalkyl; 3- to 12-membered heterocyclic; or C 1 -C 6 alkoxy; or R 4 and R 5 form C 3 -C 10 cycloalkyl together with the carbon atom of P or Q to which they are attached,

R 6 is hydrogen; or C 1 -C 6 alkyl;

W is a bond, —CH 2 —, —O—, —NH—, —CH 2 CH 2 —, —CH═CH—, or —C≡C—,

A ring is phenyl, biphenyl, thiophenyl, pyrazolyl, thiazolyl, naphthalenyl, benzothiadiazolyl, benzodioxolyl, 2,3-dihydrobenzodioxinyl, benzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, 3,4-dihydro-1,4-benzoxazinyl, 3-oxo-3,4-dihydro-1,4-benzoxazinyl, benzothiophenyl, indolyl, indazolyl, isoquinolinyl, quinolinyl, 3,4-dihydro-benzodioxepinyl, benzo[c][1,2-5]oxadiazolyl, pyridinyl, 6-oxo-1,6-dihydropyridinyl, chromanyl, dibenzofuranyl, or pyrimidinyl, and

X 1 , X 2 , X 3 , and X 4 are, independently of each other, hydrogen; cyano; halogen; C 1 -C 6 alkyl; C 1 -C 6 alkyl substituted with 1 to 3 halogens; C 1 -C 6 alkyl substituted with cyano or C 1 -C 6 alkoxy; C 3 -C 10 cycloalkyl; C 1 -C 6 alkenyl; C 1 -C 6 alkoxy; C 1 -C 6 alkoxy-C 1 -C 6 alkoxy; C 1 -C 6 alkoxy substituted with 1 to 3 halogens; C 1 -C 6 alkoxy substituted with C 3 -C 10 cycloalkyl or benzyl; morpholinyl; mono- or di-C 1 -C 6 alkylamino; pyrrolidinyl-sulfonyl; benzyl; tetrahydropyranyl; C 1 -C 6 alkylthio; or isoxazolyl.

2 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein L is —O—.

3 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein X is hydrogen; halogen; or C 1 -C 6 alkoxy.

4 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein R 4 , R 5 , and R 6 are, independently of each other, hydrogen or C 1 -C 6 alkyl.

5 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein Y is —O—.

6 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein Q is —O—.

7 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein Y is —S—.

8 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein Y is —NR 3 —.

9 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein W is a bond, —CH 2 —, or —CH═CH—.

10 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , wherein

L is —O—,

X is hydrogen; halogen; or C 1 -C 6 alkoxy,

Y is —NR 3 —; —O—; or —S—,

P is —CR 4 R 5 —,

Q is —O— or —CR 4 R 5 —,

Z is —CR 6 —,

R 3 is C 1 -C 6 alkyl,

R 4 , R 5 , and R 6 are, independently of each other, hydrogen or C 1 -C 6 alkyl,

W is a bond, —CH 2 —, -or —CH═CH—,

X 1 , X 2 , X 3 , and X 4 is, independently of each other, hydrogen; cyano; halogen; C 1 -C 6 alkyl; C 1 -C 6 alkyl substituted with 1 to 3 halogens; C 1 -C 6 alkyl substituted with cyano or C 1 -C 6 alkoxy; C 3 -C 10 cycloalkyl; C 1 -C 6 alkenyl; C 1 -C 6 alkoxy; C 1 -C 6 alkoxy-C 1 -C 6 alkoxy; C 1 -C 6 alkoxy substituted with 1 to 3 halogens; C 1 -C 6 alkoxy substituted with C 3 -C 10 cycloalkyl or benzyl; morpholinyl; mono- or di-C 1 -C 6 alkylamino; pyrrolidinyl-sulfonyl; benzyl; tetrahydropyranyl; C 1 -C 6 alkylthio; or isoxazolyl.

11 . A compound or pharmaceutically acceptable salt thereof, which is selected from the group consisting of:

(S)-quinuclidin-3-yl (7-(3-fluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chlorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-(methoxymethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(methoxymethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-(2-methoxyethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(2-methoxyethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-fluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chlorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-fluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-chlorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-methoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-methoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-ethoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-ethoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-isopropylphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-isopropylphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(tert-butyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(tert-butyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,5-dichlorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,4-dichlorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,5-dichlorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,3,4-trifluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,4,5-trifluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(difluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-fluoro-3-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-5-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-cyclopropylphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,3-dihydrofuran-5-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-cyanophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-cyanophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(dimethylamino)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzo[b]thiophen-2-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzofuran-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzofuran-2-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1H-indol-6-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1H-indol-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1H-indol-7-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1H-indazol-4-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1H-indazol-7-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1-methyl-1H-indazol-6-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1-methyl-1H-indazol-4-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1-methyl-1H-indol-2-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(isoquinolin-4-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(isoquinolin-5-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(quinolin-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(quinolin-8-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(isoquinolin-7-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-([1,1′-biphenyl]-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(pyrrolidin-1-ylsulfonyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1,3-dihydroisobenzofuran-5-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzo[c][1,2,5]thiadiazol-5-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(thiophen-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-5-methoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-chloro-3-methoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-3-methoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-methoxypyridin-4-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(dimethylamino)-4-fluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl [6,7′-bichroman]-4′-ylcarbamate;

(S)-quinuclidin-3-yl (7-(6-methoxy-5-(trifluoromethyl)pyridin-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1-benzyl-1H-pyrazol-4-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(tetrahydro-2H-pyran-4-yl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-methyl-4-morpholinophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-4-morpholinophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluoro-4-morpholinophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-cyano-4-methylphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(5-methoxypyridin-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(5-chloro-6-methoxypyridin-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-(cyclopropylmethoxy)pyridin-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-4-isopropoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methoxy-3-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,6-dimethoxyphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(4-fluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(3-fluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(2-fluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(4-chlorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(3-chlorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(2-chlorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(4-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(3-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(2-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(4-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(3-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(2-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(4-(methylthio)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(3-(methylthio)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(p-tolyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(4-cyanophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(3-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chlorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(3-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(3-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-(methoxymethoxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(methoxymethoxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(methoxymethoxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-(2-methoxyethoxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(2-methoxyethoxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(2-methoxyethoxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(difluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(8-methylquinolin-5-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,5-dimethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methoxy-3-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methoxy-2-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-4-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluoro-4-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-4-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-fluoro-2-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-6-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-fluoro-6-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,5-difluoro-4-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxy-3-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,4-dimethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,5-dimethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,3-dimethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,4-dimethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,6-dimethoxypyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(naphthalen-2-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(naphthalen-1-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(quinolin-6-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxy-3,5-dimethylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,4-dichloro-5-ethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-fluoro-5-isopropoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluoro-5-isopropoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-4-(trifluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-3-(trifluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-5-(trifluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,5-dimethyl-4-propoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(tert-butoxymethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-5-(trifluoromethoxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-butoxy-6-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-methoxynaphthalen-2-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxy-3-(trifluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzofuran-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(dimethylamino)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,5-dichlorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-isopropylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(tert-butyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-5-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-([1,1′-biphenyl]-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(isoquinolin-4-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(2-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-ethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(1-methyl-1H-indazol-4-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(isoquinolin-8-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-cyclopropylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3′,3′-dimethyl-[6,7′-bichroman]-4′-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-5-(trifluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(quinolin-8-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-4-isopropoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,6-dimethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chlorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-cyanophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(dimethylamino)-4-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1H-indol-7-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-isopropylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-fluoro-3-(trifluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-3-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-chloro-3-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1H-indazol-7-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,5-dichlorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1-benzyl-1H-pyrazol-4-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,3-dihydrobenzofuran-5-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-(cyclopropylmethoxy)pyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzofuran-2-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(3-(pyrrolidin-1-ylsulfonyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(2-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-ethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(thiophen-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methoxy-3-(trifluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-cyanophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzo[c][1,2,5]thiadiazol-5-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(isoquinolin-4-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(tert-butyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(3-methyl-4-morpholinophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,4-dichlorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(1-methyl-1H-indazol-6-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1H-indol-6-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-cyano-4-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(2,4,5-trifluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(4-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(4-(tetrahydro-2H-pyran-4-yl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-methoxypyridin-4-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluoro-4-morpholinophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-4-morpholinophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(5-methoxypyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzo[b]thiophen-2-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methoxy-3-(trifluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(4-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1H-indazol-4-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-chlorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(5-chloro-6-methoxypyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(2,3,4-trifluorophenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(difluoromethoxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(quinolin-5-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzo[c][1,2,5]oxadiazol-5-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(5-methylpyridin-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-fluoropyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-4-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-5-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-fluoro-4-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-4-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-fluoro-2-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluoro-4-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-fluoro-3-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,4-dichlorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-4-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-5-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,4-difluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,5-difluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,3-dichlorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-4-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-3-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,4-difluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,3-difluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3,5-difluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-methoxypyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-([1,1′-biphenyl]-4-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(thiazol-5-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(3-vinylphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-methoxypyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-methoxypyridin-2-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-cyanophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-fluoro-6-methylpyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzo[d][1,3]dioxol-5-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-cyclopropylpyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-(dimethylamino)pyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(5-fluoro-2-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-ethoxypyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-methoxy-5-methylpyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-methoxy-3,5-dimethylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-butylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-isobutylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-isopropoxypyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(isoxazol-3-yl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-isobutoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluoro-4-isopropoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-fluoro-4-(trifluoromethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-isopropoxy-3,5-dimethylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-phenylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(pyridin-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(pyridin-2-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-benzyl-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(m-tolyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(p-tolyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(o-tolyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-((E)-2-(thiophen-3-yl)vinyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(4-vinylphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-(2-vinylphenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxy-2-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(benzyloxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(benzyloxy)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,6-difluoropyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-allylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(cyanomethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(cyanomethyl)phenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-((E)-2-([1,1′-diphenyl]-4-yl)vinyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-cyclopropylpyrimidin-5-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-7-((E)-4-(trifluoromethyl)styryl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-3,5-dimethylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-((E)-2,4-difluorostyryl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-((E)-4-ethylstyryl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(6-ethoxynaphthalen-2-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-((E)-3-fluorostyryl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(dibenzo[b,d]furan-4-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-cyano-3-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(1-benzyl-6-oxo-1,6-dihydropyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-((E)-4-fluorostyryl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(3-fluorophenyl)-2,2-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (2,2-dimethyl-7-(3-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (2,2-dimethyl-7-(3-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chlorophenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluorophenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-methoxyphenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-isopropylphenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-5-methoxyphenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxyphenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(dimethylamino)phenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzofuran-3-yl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (4-methyl-7-(3-(trifluoromethyl)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (4-methyl-7-(3-(trifluoromethoxy)phenyl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxy-3,5-dimethylphenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-cyanophenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(tert-butyl)phenyl)-4-methylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (4-methyl-7-(4-methylthiophen-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(tert-butyl)phenyl)isochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-isopropylphenyl)isochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(tert-butyl)phenyl)-1-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzofuran-3-yl)-1-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-(4-chlorophenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluorophenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chlorophenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(trifluoromethyl)phenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(trifluoromethoxy)phenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(methoxymethoxy)phenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(tert-butyl)phenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,5-dichlorophenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-ethoxyphenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(methylthio)phenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-(dimethylamino)phenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(benzofuran-3-yl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (3,3-dimethyl-6-(4-(trifluoromethyl)phenyl)thiochroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(3-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(4-fluorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(3-chlorophenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-ethylphenyl)-6-fluoro-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethylphenyl)-6-fluoro-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(3-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(4-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxyphenyl)-6-fluoro-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-3,3-dimethyl-7-(thiophen-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(3-isopropylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-5-methoxyphenyl)-6-fluoro-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(2-fluoro-4-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(4-methoxy-2-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-butylphenyl)-6-fluoro-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-4-isopropoxyphenyl)-6-fluoro-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(tert-butyl)phenyl)-6-fluoro-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(4-methoxy-3,5-dimethylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(4-isobutoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-fluoro-7-(6-isopropoxypyridin-3-yl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-fluorophenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-fluorophenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chlorophenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-ethylphenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethylphenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-methoxy-7-(3-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-methoxy-7-(4-methoxyphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-ethoxyphenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-methoxy-3,3-dimethyl-7-(thiophen-3-yl)chroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-isopropylphenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-chloro-5-methoxyphenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(2-fluoro-4-methoxyphenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-methoxy-7-(4-methoxy-2-methylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-butylphenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(3-chloro-4-isopropoxyphenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-(tert-butyl)phenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (6-methoxy-7-(4-methoxy-3,5-dimethylphenyl)-3,3-dimethylchroman-4-yl)carbamate;

(S)-quinuclidin-3-yl (7-(4-isobutoxyphenyl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate; and

(S)-quinuclidin-3-yl (7-(6-isopropoxypyridin-3-yl)-6-methoxy-3,3-dimethylchroman-4-yl)carbamate.

12 . A pharmaceutical composition for inhibiting glucosylceramide synthase comprising the compound or pharmaceutically acceptable salt thereof as claimed in claim 1 as an active ingredient.

13 . A pharmaceutical composition as claimed in claim 12 , for treating Gaucher disease, Fabry disease, Tay-Sachs disease, or Parkinson's disease.

14 . A method for inhibiting glucosylceramide synthase in a mammal in need thereof, which comprises administering a therapeutically effective amount of the compound or pharmaceutically acceptable salt thereof as claimed in claim 1 to the mammal.

15 . The compound or pharmaceutically acceptable salt thereof as claimed in claim 1 , which is selected from the group consisting of: