JP-2022533311-A5 -

Dates

Publication Date

20230525

Application Date

20200519

Description

The present invention may include the following embodiments.[1]Formula (Id)(In the formula, R1 and R2 are a) to c) below):a) R1 is selected from H, C1-C6 alkyl, benzyl and linear-C(O)C1-C6 alkyl, and R2 is the following substituent (i), orb) R1 is one of the following substituents (i), and R2 is selected from H, C1-C6 alkyl, benzyl, and linear-C(O)C1-C6 alkyl, orc) Both R1 and R2 have the following substituents (i)It is represented byin accordance withR3 is selected from H and -C(O)C1-C6 alkyl groups.* indicates a connection point.The carbon atom at the bonding site on substituent (i) has an S configuration.However, if either R1 or R2 is substituent (i) and R3 is H, the other R1 or R2 cannot be a linear-C(O)C1-C6 alkyl group.Compounds or pharmaceutically acceptable salts thereof.[2]The compound described in [2] or an agent-acceptable salt thereof, wherein R1 is selected from H, C1-C6 alkyl, benzyl, and linear-C(O)C1-C6 alkyl, and R2 is substituent (i).[3]R1 is substituent (i), and R2 is selected from H, C1-C6 alkyl, benzyl, and linear-C(O)C1-C6 alkyl, the compound described in [2] or an agent-acceptable salt thereof.[4]R1 and R2 are both represented by substituent (i), the compounds described in [2] or pharmaceutically acceptable salts thereof.[5]R1 or R2 is -C(O)methyl, a compound or pharmaceutically acceptable salt thereof as described in any one of [2] to [4].[6]R3 is -C(O)methyl, a compound or an pharmaceutically acceptable salt thereof as described in any one of [1] to [5].[7]R3 is H, a compound or an pharmaceutically acceptable salt thereof as described in any one of items [1] to [5].[8]A compound or a pharmaceutically acceptable salt thereof as described in [1] or [5], wherein one of R1 and R2 is H, one of R1 and R2 is substituent (i), and R3 is H.[9](2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((4aR,10aR)-7-(benzyloxy)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate;(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate;(2S,3R,4S,5R,6R)-2-(((4aR,10aR)-7-acetoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate;(2S,3R,4S,5S,6R)-2-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((4aR,10aR)-6-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-7-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyltriacetate;(2S,3R,4S,5R,6R)-2-(((4aR,10aR)-6-acetoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-7-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate;(2S,3R,4S,5S,6R)-2-(((4aR,10aR)-6-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-7-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;[(2R,3R,4S,5R,6S)-6-[[(4aR,10aR)-1-propyl-6-[(2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinoline-7-yl]oxy]-3,4,5-triacetoxy-tetrahydropyran-2-yl]methylacetate; and(2R, 2'R, 3S, 3'S, 4S, 4'S, 5R, 5'R, 6S, 6'S)-6,6'-(((4aR, 10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6,7-diyl)bis(oxy))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol)A compound selected from the group consisting of [1] or a salt of either of the compounds described above that is acceptable as a drug.[10]A compound described in any one of items [1] to [9], or a pharmacopoeial salt thereof, for use as a drug.[11]A pharmaceutical composition comprising a therapeutically effective amount of a compound described in any one of items [1] to [9] or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients.[12]The pharmaceutical composition according to [11], which is an oral pharmaceutical composition such as a tablet or capsule for oral administration.[13]A compound described in any one of items [1] to [9] or an acceptable pharmacokinetic salt thereof, for use in the treatment of neurodegenerative diseases or disorders such as Parkinson's disease, Huntington's disease, restless limb syndrome, or Alzheimer's disease, or neuropsychiatric disorders or disorders such as schizophrenia, attention deficit hyperactivity disorder, or drug addiction.[14]A method for treating neurodegenerative diseases or disorders such as Parkinson's disease, Huntington's disease, restless limb syndrome, or Alzheimer's disease, or neuropsychiatric disorders or disorders such as schizophrenia, attention deficit hyperactivity disorder, or drug addiction, comprising administering a therapeutically effective amount of any one of the compounds described in [1] to [9] or an acceptable pharmacopoeia thereof to a patient in need.[15]The use of any one of the compounds described in [1] to [9] or a pharmacopoeia permissible salt thereof in the manufacture of drugs for the