Novel compounds having inhibitory activity against glucosylceramide synthase, or pharmaceutically acceptable salts thereof, methods for producing the same, and pharmaceutical compositions containing the same.

Abstract

The present invention provides a novel compound having inhibitory activity against glucosylceramide synthase (GCS), i.e., a compound having a 2,3-dihydro-1H-indene moiety, a 1,2,3,4-tetrahydronaphthalene moiety, or a chroman moiety, or a pharma- ceutically acceptable salt thereof, a method for producing the same, a pharmaceutical composition containing the same, and use thereof. The compound or a pharma- ceutically acceptable salt thereof has inhibitory activity against glucosylceramide synthase (GCS), and also has an effect of alleviating symptoms in not only the peripheral nervous system but also the central nervous system due to its excellent blood-brain barrier permeability. Therefore, the compound or a pharma- ceutically acceptable salt thereof can be usefully applied to the prevention or treatment of various diseases associated with GCS, such as Gaucher disease, Fabry disease, Tay-Sachs disease, and Parkinson's disease.

Claims

1. Compounds of chemical formula 1 or their pharmaceutically acceptable salts: 【Chemistry 1】 During the ceremony, W and Q are independent of each other, -CR １ R ２ -and, Y is a bond, -CR １ 'R ２ '-; or -O-, R １ and R ２ are each independently hydrogen; halogen; C １ -C ６ alkyl; C having a nitrogen atom, an oxygen atom, or a sulfur atom １ -C ６ alkyl; C ３ -C １０ cycloalkyl; a heterocyclic group having 3 to 12 members; or C １ -C ６ alkoxy, or R １ and R ２ together with the carbon atom to which they are attached form C ３ -C １０ cycloalkyl, R １ 'and R ２ ' are, independently of each other, hydrogen; halogen; C １ ~C ６ Alkyl; C having a nitrogen atom, oxygen atom, or sulfur atom. １ ~C ６ Alkyl; C ３ ~C １０ Cycloalkyl group; 3-12 membered heterocyclic group; or C １ ~C ６ It is either an alkoxy or R １ 'and R ２ ' is C along with the carbon atoms to which they are bonded. ３ ~C １０ Forming a cycloalkyl group, X is hydrogen; halogen; C １ ~C ６ Alkyl; C substituted with 1 to 3 halogens １ ~C ６ Alkyl; C having a nitrogen atom, oxygen atom, or sulfur atom. １ ~C ６ Alkyl; C １ ~C ６ Alkoxy; or C substituted with 1 to 3 halogens １ ~C ６ It is an alkoxy, Ring A consists of 6-12 membered aryls; 5-12 membered heteroaryls; C ３ ~C １０ Cycloalkyl group; or a 3- to 12-membered heterocyclic group, R ３ , R ４ , and R ５ These are, independently, hydrogen; cyano; halogen; and C. １ ~C ６ Alkyl; C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl; C substituted with 1 to 3 halogens １ ~C ６ Alkyl; C ３ ~C １０ Cycloalkyl; 3- to 12-membered heterocyclic group; C １ ~C ６ Alkoxy; C substituted with 1 to 3 halogens １ ~C ６ Alkoxy; C １ ~C ６ Alkoxy-C １ ~C ６ Alkoxy;morpholinyl-C １ ~C ６ Alkoxy; mono- or di-C １ ~C ６ Alkylamino-C １ ~C ６ Alkoxy; C ３ ~C １０ Cycloalkyl-C １ ~C ６ Alkoxy; C １ ~C ６ Alkylthio; amino; mono- or di-C １ ~C ６ Alkylamino; C １ ~C ６ It is alkylcarbonyl; hydroxy; or nitro.

2. W is -C(CH ３ ) ２ -The compound according to claim 1 or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 1, wherein Y is a bond, or a pharmaceutically acceptable salt thereof.

4. Y is -CH ２ -The compound according to claim 1 or a pharmaceutically acceptable salt thereof.

5. The compound according to claim 1, wherein Y is -O-, or a pharmaceutically acceptable salt thereof.

6. X is hydrogen, halogen, C １ ~C ６ Alkyl, or C １ ~C ６ A compound according to claim 1, wherein the compound is an alkoxy, or a pharmaceutically acceptable salt thereof.

7. The compound according to claim 1, wherein the A ring is phenyl or pyridinyl, or a pharmaceutically acceptable salt thereof.

8. R ３ 、 R ４ 、 and R ５ are each independently hydrogen, halogen, C １ - C ６ alkyl, C １ - C ６ alkoxy, C １ - C ６ alkoxy substituted with 1 to 3 halogens, or C ３ - C １０ cycloalkyl-C １ - C ６ alkoxy, or a compound according to claim 1 or a pharmaceutically acceptable salt thereof.

9. W is -C(CH ３ ) ２ -and, Q is -CH ２ -and, Y is a combination, X is hydrogen, halogen, C １ ~C ６ Alkyl, or C １ ~C ６ It is an alkoxy, The A ring is phenyl or pyridinyl. R ３ , R ４ , and R ５ However, each is independent of hydrogen, halogen, and C. １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C substituted with 1 to 3 halogens １ ~C ６ Alkoxy, or C ３ ~C １０ Cycloalkyl-C １ ~C ６ A compound according to claim 1, wherein the compound is an alkoxy, or a pharmaceutically acceptable salt thereof.

10. W is -C(CH ３ ) ２ -and, Q is -CH ２ -and, Y is -CH ２ -and, X is hydrogen, halogen, C １ ~C ６ Alkyl, or C １ ~C ６ It is an alkoxy, The A ring is phenyl or pyridinyl. R ３ , R ４ , and R ５ However, each is independent of hydrogen, halogen, and C. １ ~C ６ Alkyl, or C １ ~C ６ A compound according to claim 1, wherein the compound is an alkoxy, or a pharmaceutically acceptable salt thereof.

11. W is -C(CH ３ ) ２ -and, Q is -CH ２ -and, Y is -O-, X is hydrogen, halogen, C １ ~C ６ Alkyl, or C １ ~C ６ It is an alkoxy, The A ring is phenyl or pyridinyl. R ３ , R ４ , and R ５ However, each is independent of hydrogen, halogen, and C. １ ~C ６ Alkyl, or C １ ~C ６ A compound according to claim 1, wherein the compound is an alkoxy, or a pharmaceutically acceptable salt thereof.

12. (S)-Quinuclidin-3-yl ((R)-5-(3-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-(tert-butyl)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3,5-dimethyl-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(6-(cyclopropylmethoxy)pyridine-3-yl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butoxy-3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxy-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-fluoro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-fluoro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butoxy-3-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxy-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-fluoro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-fluoro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethyl-3-fluorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-Isopropoxy-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-Isopropoxy-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-isopropoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3,5-difluoro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-(cyclopropylmethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-(cyclopropylmethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3,5-dichloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-(tert-butoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-(tert-butoxy)-2-chlorophenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxy-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-2,2-dimethyl-5-(3-methyl-4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-(difluoromethoxy)-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-fluoro-5-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-fluoro-5-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-fluoro-5-(2,2,2-trifluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-chloro-3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-5-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-5-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-(2,2,2-trifluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3,5-dimethyl-4-propoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-ethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-2,2-dimethyl-5-(3-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-2,2-dimethyl-5-(3-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-butoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxy-3,5-dimethylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-fluoro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-methylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-propoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butoxy-3-chlorophenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxy-3-fluorophenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-fluoro-4-propoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethyl-3-fluorophenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-isopropoxy-3-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-isopropoxy-3-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(4-isopropoxy-2-methylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3,5-difluoro-4-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-(cyclopropylmethoxy)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-(cyclopropylmethoxy)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3,5-dichloro-4-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-(tert-butoxy)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-(tert-butoxy)-2-chlorophenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-methoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-ethoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxy-3-methylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-2,2-dimethyl-5-(3-methyl-4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-(difluoromethoxy)-3-methylphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-fluoro-5-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-fluoro-5-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-fluoro-5-(3-fluoro-5-(2,2,2-trifluoroethoxy)phenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-chloro-3-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-5-isobutoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-5-isopropoxyphenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(2-chloro-4-(2,2,2-trifluoroethoxy)phenyl)-6-fluoro-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethylphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-2,2,6-trimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-isopropylphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butylphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-isobutylphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-ethoxyphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-2,2,6-trimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-isopropoxyphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butoxyphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl ((R)-5-(4-isobutoxyphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidine-3-yl ((R)-5-(2-fluoro-4-methoxyphenyl)-2,2,6-trimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-ethoxy-5-(4-ethylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-ethoxy-2,2-dimethyl-5-(4-propylphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-ethoxy-5-(4-isopropylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butylphenyl)-6-ethoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-ethoxy-5-(4-isobutylphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-ethoxy-5-(4-ethoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-ethoxy-2,2-dimethyl-5-(4-propoxyphenyl)-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-ethoxy-5-(4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(4-butoxyphenyl)-6-ethoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-ethoxy-5-(4-isobutoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-6-ethoxy-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-ethoxy-5-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-ethylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-2,2-dimethyl-6-(4-propylphenyl)-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-isopropylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-butylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-ethoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-2,2-dimethyl-6-(4-propoxyphenyl)-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-butoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-isobutoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3,5-dimethyl-4-propoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(2-fluoro-4-methoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-butoxy-3,5-dimethylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-methoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-ethoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-butoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-2,2-dimethyl-6-(3-propylphenyl)-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-isobutylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-ethylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-2,2-dimethyl-6-(3-propoxyphenyl)-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-isobutylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-fluoro-4-isopropoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-isopropylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-isobutoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-ethoxy-3,5-dimethylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-isopropoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-methoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-isopropoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(2-chloro-4-isopropoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-ethyl-3-fluorophenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-ethylphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-2,2-dimethyl-6-(4-propylphenyl)-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(4-isopropylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-butylphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(4-isobutylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(4-methoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-ethoxyphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-2,2-dimethyl-6-(4-propoxyphenyl)-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-butoxyphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(4-isobutoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(4-methoxy-3,5-dimethylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3,5-dimethyl-4-propoxyphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(4-isopropoxy-3,5-dimethylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-butoxy-3,5-dimethylphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(3-methoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-ethoxyphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-butoxyphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-ethylphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-2,2-dimethyl-6-(3-propylphenyl)-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(3-isobutylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(3-isopropylphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(3-isobutoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-2,2-dimethyl-6-(3-propoxyphenyl)-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(3-chloro-4-isopropoxyphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-Fluoro-6-(2-Fluoro-4-methoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-6-(4-ethoxy-3,5-dimethylphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(3-isopropoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-fluoro-6-(4-isopropoxyphenyl)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate; (S)-Quinuclidin-3-yl ((R)-7-Fluoro-6-(3-Fluoro-4-Isopropoxyphenyl)-2,2-Dimethyl-1,2,3,4-Tetrahydronaphthalene-1-yl)carbamate; and (S)-Quinuclidin-3-yl ((R)-6-(2-chloro-4-isopropoxyphenyl)-7-fluoro-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-yl)carbamate A compound according to claim 1, selected from the group consisting of the following, or a pharmaceutically acceptable salt thereof.

13. The compound according to claim 1, which is (S)-quinuclidin-3-yl ((R)-5-(3-chloro-4-isopropoxyphenyl)-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)carbamate, or a pharmaceutically acceptable salt thereof.

14. A pharmaceutical composition for inhibiting glucosylceramide synthase, comprising a compound according to any one of claims 1 to 13 or a pharmaceutically acceptable salt thereof as an active ingredient.

15. The pharmaceutical composition according to claim 14 for preventing or treating Gaucher disease, Fabry disease, Taysachs disease, or Parkinson's disease.

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