US2001036947A1PendingUtilityA1

Pipecolic acid derivative hair growth compositions and uses

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Assignee: GUILFORD PHARM INCPriority: Jun 4, 1997Filed: Feb 13, 2001Published: Nov 1, 2001
Est. expiryJun 4, 2017(expired)· nominal 20-yr term from priority
Inventors:Joseph P. SteinerGregory S. Hamilton
A61K 8/4913A61K 2800/70A61K 31/426C07D 417/12A61K 31/401A61K 31/4545A61K 31/4025A61K 31/40A61K 31/445A61K 31/4439A61K 31/44A61K 31/00C07D 401/12A61Q 7/00C07D 401/06A61K 45/06
53
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Claims

Abstract

This invention relates to pharmaceutical compositions and methods for treating alopecia and promoting hair growth using pipecolic acid derivatives.

Claims

exact text as granted — not AI-modified
We claim:  
     
         1 . A method for treating alopecia or promoting hair growth in an animal, which comprises administering to said animal an effective amount of a pipecolic acid derivative.  
     
     
         2 . The method of    claim 1   , wherein the pipecolic acid derivative has an affinity for an FKBP-type immunophilin.  
     
     
         3 . The method of    claim 2   , wherein the FK EP-type immunophilin is FK BP-12.  
     
     
         4 . The method of    claim 1   , wherein the pipecolic acid derivative is immunosuppressive.  
     
     
         5 . The method of    claim 1   , wherein the pipecolic acid derivative is non-immunosuppressive.  
     
     
         6 . The method of    claim 1   , wherein the pipecolic acid derivative is Way-124, 666.  
     
     
         7 . The method of    claim 1   , wherein the pipecolic acid derivative is rapamycin.  
     
     
         8 . The method of    claim 1   , wherein the pipecolic acid derivative is Rap-Pa.  
     
     
         9 . The method of    claim 1   , wherein the pipecolic acid derivative is SLB-506.  
     
     
         10 . The method of    claim 1   , wherein the pipecolic acid derivative is selected from the group consisting of: 
 4-(4-methoxyphenyl)butyl (2S)-1-[2-(3,4,5-trimethoxyphenyl)acetyl]hexahydro-2-pyridinecarboxylate;    4-(4-methoxyphenyl)butyl (2S)-1-[2-(3,4,5-trimethoxyphenyl)acryloyl]hexahydro-2-pyridinecarboxylate;    4-(4-methoxyphenyl)butyl (2S)-1-[2-(3,4,5-trimethoxyphenyl)propanoyl]hexahydro-2-pyridinecarboxylate;    4-(4-methoxyphenyl)butyl (2S)-1-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]hexahydro-2-pyridinecarboxylate;    3-cyclohexylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    3-phenylpropyl (2S)-1-(3,3-dimethyl -2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    3-(3,4,5-trimethoxyphenyl)propyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)hexahydro-2-pyridinecarboxylate;    (1R)-2,2-dimethyl-1-phenethyl-3-butenyl (2S)-1-(3, 3-dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    (1R)-1,3-diphenylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl) hexahydro -2-pyridinecarboxylate;    (1R)-1-cyclohexyl-3-phenylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)hexahydro-2-pyridinecarboxylate;    (1S)-1,3-diphenylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    (1S)-1-cyclohexyl-3-phenylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)hexahydro-2-pyridinecarboxylate;    (22aS)-15,15-dimethylperhydropyrido[2,1-c][1,9,4]dioxazacyclononadecine-1,12,16,17-tetraone;    (24aS)-17,17-dimethylperhydropyrido [2,1- c][1,9,4]dioxazacyclohenicosine-1,14,18, 19-tetraone;    ethyl 1-(2-oxo-3-phenylpropanoyl)-2-piperidinecarboxylate;    ethyl 1-pyruvoyl-2-piperidinecarboxylate;    ethyl 1-(2-oxobutanoyl)-2-piperidinecarboxylate;    ethyl 1-(3-methyl-2-oxobutanoyl)-2-piperidinecarboxylate;    ethyl 1-(4-methyl-2-oxoper -tanoyl)-2-piperidinecarboxylate;    ethyl 1-(3,3-dimethyl-2-oxobutanoyl)-2-piperidinecarboxylate;    ethyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    4-[2-(ethyloxycarbonyl) piperidino]-2, 2-dimethyl-3, 4-dioxobutyl acetate;    ethyl 1-[2-(2-hydroxytetrahydro-2H-2-pyranyl)-2-oxcacetyl]-2-piperidinecarboxylate;    ethyl 1-[2-(2-methoxytetrahydro-2H-2-pyranyl)-2-oxcacetyl]-2-piperidinecarboxylate;    ethyl 1-[2-(1-hydroxycyclohexyl)-2-oxoacetyl]-2-piperidinecarboxylate;    ethyl 1-[2-(1-methoxycycl ahexyl)-2-oxoacetyl]-2-piperidinecarboxylate;    ethyl 1-(2-cyclohexyl-2-oxoacetyl)-2-piperidinecarboxylate;    ethyl 1-(2-oxo-2-piperidinoacetyl)-2-piperidinecarboxylate;    ethyl 1-[2-(3,4-dihydro-2H-6-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    ethyl 1-(2-oxo-2-phenylacetyl)-2-piperidinecarboxylate;    ethyl 1-(4-methyl-2-oxo-1-thioxopentyl)-2-piperidinecarboxylate;    3-phenylpropyl 1-(2-hydroxy-3,3-dimethylpentanoyl)-2-piperidinecarboxylate;    (1R)-1-phenyl-3-(3,4,5-trimethoxyphenyl)propyl 1-(3,3-dimethylbutanoyl)-2-piperidinecarboxylate;    (1R)-1,3-diphenylpropyl 1-(benzylsulfonyl)-2-piperidinecarboxylate;    3-(3,4,5-trimethoxyphenyl)propyl 1-(benzylsulfonyl)-2-piperidinecarboxylate;    1-(2-[(2R, 3R, 6S)-6-[(2S, 3E,5E, 7E, 9S, 11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2- pyranyl)-2-oxoacetyl)-2-piperidinecarboxylic acid;    methyl 1-(2-[(2R, 3R, 6S)-6-[(2S, 3E, 5E, 7E, 9S, 11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7- tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    isopropyl 1-(2, 3,6S)-6-[(2S,3E,SE,7E,9S,11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    benzyl 1-(2-[(2R, 3R, 6S)-6-[(2S, 3E, SE, 7E, 9S, 11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    1-phenylethyl 1-(2-(2R, 3R, 6S)-6-(2S, 3E, SE, 7E, 9S, 11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    (Z)-3-phenyl-2-propenyl 1-(2-[2R,3R, 6c l -6-[(2S, 3E, SE, 7E, 9S, 11R)-2,13-dimethoxy-3,9 ,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    3-(3,4-dimethoxyphenyl)propyl 1-(2-[(2R,3R,6S)-6-[(2S,3E,5E,7E,9s,11R)-2,13-dimethoxy-3, .9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxcacetyl)-2-piperidinecarboxylate;    N2- benzyl-1-(2-(2R , 3R , 6S )-6-[(2S,3 9,SE,7E,9S,11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxcacetyl)-2-piperidinecarboxylate;    N2-(3-phenylpropyl)-1-(2-[(2R , 3R , 6S)-6-(2S, 3E, 5E, 7E, 9S, 1R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    (E)-3-(3,4-dichlorophenyl)-2-propenyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    (E)-3-(3,4,5-trimethoxyphenyl)-2-propenyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarbcxylate;    (E)-3-phenyl-2-propenyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    (E)-3-((3-(2,5-dimethoxy)-phenylpropyl)phenyl)-2-propenyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    (E)-3-(1,3-benzodioxol-5-yl)-2-propenyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    4-(4-methoxyphenyl)butyl 1-(2-oxo-2-phenylacetyl)-2-piperidinecarboxylate;    3-phenylpropyl 1-(2-oxo-2-phenylacetyl)-2-piperidinecarboxylate;    3-(3-pyridyl)propyl 1-(2-oxo-2-phenylacetyl)-2-piperidinecarboxylate;    3-(3-pyridyl)propyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    4-phenyl-1-(3-phenylpropyl)butyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    4-(4-methoxyphenyl)butyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    1-(4-methoxyphenethyl)-4-phenylbutyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    3-(2,5-dim eethoxyphenyl)propyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    3-(1,3-benzodioxol-5-yl)propyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    1-phenethyl-3-phenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    4-(4-methoxyphenyl)butyl 1-(2-cyclohexyl-2-oxoacetyl)-2-piperidinecarboxylate;    3-cyclohexylpropyl 1-(2-cyclohexyl-2-oxcacetyl)-2-piperidinecarboxylate;    3-phenylpropyl 1-(2-cyclohexyl-2-oxoacetyl)-2-piperidinecarboxylate;    3-cyclohexylpropyl 1-(3,3-dimethyl-2-oxobutanoyl)-2-piperidinecarboxylate;    3-phenylpropyl 1-(3,3-dimethyl-2-oxobutanoyl)-2-piperidinecarboxylate;    4-(4-methoxyphenyl)butyl 1-(3,3-dimethyl-2-oxobutanoyl)-2-piperidinecarboxylate;    4-phenyl-1-(3-phenylpropyl)butyl 1-(3,3-dimethyl-2-oxobutanoyl)-2-piperidinecarboxylate; and    pharmaceutically acceptable salts, esters, and solvates thereof.    
     
     
         11 . A pharmaceutical composition which comprises: 
 (i) an effective amount of a pipecolic acid derivative for treating alopecia or promoting hair growth in an animal; and    (ii) a pharmaceutically acceptable carrier.    
     
     
         12 . The pharmaceutical composition of    claim 11   , wherein the pipecolic acid derivative has an affinity for an FKBP-type immunophilin.  
     
     
         13 . The pharmaceutical composition of    claim 12   , wherein the FKBP-type immunophilin is FKBP-12.  
     
     
         14 . The pharmaceutical composition of    claim 11   , wherein the pipecolic acid derivative is immunosuppressive.  
     
     
         15 . The pharmaceutical composition of    claim 11   , wherein the pipecolic acid derivative is non-immunosuppressive.  
     
     
         16 . The pharmaceutical composition of    claim 11   , wherein the pipecolic acid derivative is Way-124,666.  
     
     
         17 . The pharmaceutical composition of    claim 11   , wherein the pipecolic acid derivative is rapamycin.  
     
     
         18 . The pharmaceutical composition of    claim 11   , wherein the pipecolic acid derivative is Rap-Pa.  
     
     
         19 . The pharmaceutical composition of    claim 11   , wherein the pipecolic acid derivative is SLB-506.  
     
     
         20 . The pharmaceutical composition of    claim 11   , wherein the pipecolic acid derivative is selected from the group consisting of: 
 4-(4-methoxyphenyl)butyl (2S)-1-[2-(3,4,5-trimethoxyphenyl)acetyl]hexahydro-2-pyridinecarboxylate;    4-(4-methoxyphenyl)butyl (2S)-1-[2-(3,4,5-trimethoxyphenyl)acryloyl ]hexahydro-2-pyridinecarboxylate;    4-(4-methoxyphenyl)butyl (2S)-1-[2-(3, 4,5-trimethoxyphenyl) propanoyl]hexahydro-2-pyridinecarboxylate;    4-(4-methoxyphenyl)butyl (2S)-1-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]hexahydro-2-pyridinecarboxylate;    3-cyclohexylpropyl (2S) l-(3,3-dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    3-phenylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    3-(3,4,5-trimethoxyphenyl)propyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)hexahydro-2-pyridinecarboxylate;    (1R)-2,2-dimethyl-1-phenethyl-3-butenyl (2S)-1-(3, 3-dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    (1R)-1,3-diphenylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    (1R)-1-cyclohexyl-3-phenylpropyl (2S)-1-(3,3- dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    (1S)-1,3-diphenylpropyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    (1S)-1-cyclohexyl-3-phenylpropyl (2S)-1-(3, 3-dimethyl-2-oxopentanoyl) hexahydro-2-pyridinecarboxylate;    (22aS)-15,15-dimethylperhydropyrido[2,1-c][1,9,4]dioxazacyclononadecine-1,12,16,17-tetraone;    (24aS)-17,17-dimethylperhydropyrido [2,1-c][1,9,4]dioxazacyclohenicosine-1,14,18, 19-tetraone;    ethyl 1-(2-oxo-3-phenylpropanoyl)-2-piperidinecarboxylate;    ethyl 1-pyruvoyl -2-piperidinecarboxylate;    ethyl 1-(2-oxobutanoyl)-2-piperidinecarboxylate;    ethyl 1-(3-methyl-2-oxobutanoyl)-2-piperidinecarboxylate;    ethyl 1-(4-methyl-2-oxopentanoyl)-2-piperidinecarboxylate;    ethyl 1-(3,3-dimethyl-2-oxobutanoyl)-2-piperidinecarboxylate;    ethyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    4-[2-(ethyloxycarbonyl)piperidino]-2,2-dimethyl-3,4-dioxobutyl acetate;    ethyl 1-[2-(2-hydroxytetrahydro-2H-2-pyranyl)-2-oxoacetyl]-2-piperidinecarboxylate;    ethyl 1-[2-(2-methoxytetrahydro-2H-2-pyranyl)-2-oxoacetyl]-2-piperidinecarboxylate;    ethyl 1-[2-(1-hydroxycyclohexyl)-2-oxoacetyl]-2-piperidinecarboxylate;    ethyl 1-[2-(1-methoxycyclohexyl)-2-oxoacetyl]-2-piperidinecarboxylate;    ethyl 1-(2-cyclohexyl-2-oxoacetyl)-2-piperidinecarboxylate;    ethyl 1-(2-oxo-2-piperidinoacetyl)-2-piperidinecarboxylate;    ethyl 1-[2-(3,4-dihydro-2H-6-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    ethyl I-(2-oxo-2-phenylacecyl)-2-piperidinecarboxylate;    ethyl 1-(4-methyl-2-oxo-1-thioxopentyl)-2-piperidinecarboxylate;    3-phenylpropyl 1-(2-hydroxy-3,3-dimethylpentanoyl)-2-piperidinecarboxylate;    (1R)-1-phenyl-3-(3,4,5-trimethoxyphenyl)propyl 1-(3,3-dimethylbutanoyl)-2-piperidinecarboxylate;    (1R)-1,3-diphenylpropyl 1-(benzylsulfonyl)-2-piperidinecarboxylate;    3-(3,4,5-trimethoxyphenyl)propyl 1-(benzylsulfonyl)-2-piperidinecarboxylate;    1-(2-[(2R,3R, ,6S)-6-[(2S,3E, 5E,7E,9S,11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylic acid;    methyl 1-(2-(2R,3R, 6S)-6-[(2S, 3E, 5E, 7E, 9S, 11R);    2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    isopropyl 1-(2-[(2R, 3 1R, 6S)-6-[(2S,3E,5E ,7E ,9S,11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    benzyl 1-(2-[(2R, 3R, 6S)-6-[(2S, 3E, SE, 7E, 9S, 11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarbcxylate;    1-phenylethyl 1-(2-[(2R, 3 R,6S)-6-[(2S,3E,5E,7E,9S,11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    (Z)-3-phenyl-2-propenyl 1-(2-[(2R,3R,6S)-6-[(2S, 3E, 5E, 7E, 9S, 11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    3-(3,4-dimethoxyphenyl)propyl 1-(2-[(2R,3R,6S)-6-[(2S,3E,5E,7E,9S,11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    N 2- benzyl-1-(2-[(2R , 3R, 6S)-6-[(2S, 3E,5E,7E,9S,11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    N2-(3-phenylpropyl)-1-(2-[(2R, 3R, 6S)-6-[(2S,3E, SE, 7E, 9S, 11R)-2,13-dimethoxy-3,9,11-trimethyl-12-oxo-3,5,7-tridecatrienyl]-2-hydroxy-3-methyltetrahydro-2 H-2-pyranyl)-2-oxoacetyl)-2-piperidinecarboxylate;    (E)-3-(3,4-dichlorophenyl)-2-propenyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    (E)-3-(3,4,-5-trimethoxyphenyl)-2-propenyl-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    (E)-3-phenyl-2-propenyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    (E)-3-((3-(2,5-dimethoxy)-phenylpropyl)phenyl)-2-propenyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    (E)-3-(1,3-benzodioxol-5-yl)-2-propenyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    4-(4-methoxyphenyl)butyl 1-(2-oxo-2-phenylacetyl)-2-piperidinecarboxylate;    3-phenylpropyl 1-(2-oxo-2-phenylacetyl)-2-piperidinecarboxylate;    3-(3-pyridyl)propyl 1-(2-oxo-2-phenylacetyl)-2-piperidinecarboxylate;    3-(3-pyridyl)propyl 1-(3,3-dimethyl-2-oxopentancyl)-2-piperidinecarboxylate;    4-phenyl-1-(3-phenylpropyl)butyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    4-(4-methoxyphenyl)butyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    1-(4-methoxyphenethyl)-4-phenylbutyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    3-(2,5-dimethoxyphenyl)propyl 1-(3,3-dimethyl-2-oxopentancyl)-2-piperidinecarboxylate;    3-(1,3-benzodioxol-5-yl)propyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    1-phenethyl-3-phenylpropyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate;    4-(4-methoxyphenyl)butyl 1-(2-cyclohexyl-2-oxcacetyl)-2-piperidinecarboxylate;    3-cyclohexylpropyl 1-(2-cyclohexyl-2-oxoacetyl)-2-piperidinecarboxylate;    3-phenylpropyl 1-(2-cyclohexyl-2-oxcacetyl)-2-piperidinecarboxylate;    3-cyclohexylpropyl 1-(3,3-dimethyl-2oxobutanoyl)-2-piperidinecarboxylate;    3-phenylpropyl 1-(3,3-dimethyl-2-oxobutanoyl)-2-piperidinecarboxylate;    4-(4-methoxyphenyl)butyl 1-(3,3-dimethyl-2-oxobutanoyl)-2-piperidinecarboxylate;    4-phenyl-1-(3-phenylpropyl)butyl 1-(3,3-dimethyl-2-oxobutanoyl)-2-piperidinecarboxylate; and    pharmaceutically acceptable salts, esters, and solvates thereof.

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