US 12,673,944 B2Granted

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

AssigneesYuhan Corporation, The Green Cross Corporation

InventorsDong-Hoon Kim, Jae-Eun Joo, Eui-Chul Lee, Tae-Dong Han, Seung-Yub Shin, Sool-Ki Kwon

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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.:

Claims20

Dependent claims

A compound of Formula 1 or pharmaceutically acceptable salt thereof:

wherein,
L is —O—, —CO—, —CR1R2—, or —NR3—,
X is hydrogen;
halogen;
C1-C6 alkyl;
C1-C6 alkyl substituted with 1 to 3 halogens;
C1-C6 alkoxy;
or C1-C6 alkoxy substituted with 1 to 3 halogens,
Y is —NR3—;
—O—;
or —S—,
P is —CR4R5—,
Q is —O— or —CR4R5—,
Z is —CR6—,
R1 and R2 are, independently of each other, hydrogen;
halogen;
C1-C6 alkyl;
C3-C10 cycloalkyl;
3- to 12-membered heterocyclic;
or C1-C6 alkoxy;
or R1 and R2 form C3-C10 cycloalkyl together with the carbon atom to which they are attached,
R3 is C1-C6 alkyl,
R4 and R5 are, independently of each other, hydrogen;
halogen;
C1-C6 alkyl;
C3-C10 cycloalkyl;
3- to 12-membered heterocyclic;
or C1-C6 alkoxy;
or R4 and R5 form C3-C10 cycloalkyl together with the carbon atom of P or Q to which they are attached,
R6 is hydrogen;
or C1-C6 alkyl;
W is a bond, —CH2—, —O—, —NH—, —CH2CH2—, —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
X1, X2, X3, and X4 are, independently of each other, hydrogen;
cyano;
halogen;
C1-C6 alkyl;
C1-C6 alkyl substituted with 1 to 3 halogens;
C1-C6 alkyl substituted with cyano or C1-C6 alkoxy;
C3-C10 cycloalkyl;
C1-C6 alkenyl;
C1-C6 alkoxy;
C1-C6 alkoxy-C1-C6 alkoxy;
C1-C6 alkoxy substituted with 1 to 3 halogens;
C1-C6 alkoxy substituted with C3-C10 cycloalkyl or benzyl;
morpholinyl;
mono- or di-C1-C6 alkylamino;
pyrrolidinyl-sulfonyl;
benzyl;
tetrahydropyranyl;
C1-C6 alkylthio;
or isoxazolyl.

49 more elements

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.

365 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/755,858Filed 12 Nov 2020
Priority: KR 10-2019-014668415 Nov 2019
Published: US 2023/0002380 A15 Jan 2023
Granted: 7 Jul 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 453/02
Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids: containing not further condensed…
A61P 3/00
Drugs for disorders of the metabolism
C07D 471/08
In which the condensed system contains two hetero rings: bridged systems
C07D 519/00
Heterocyclic compounds containing more than one system of two or more relevant