JP-2022533913-A5 -

Dates

Publication Date

20230518

Application Date

20200519

Description

The present invention encompasses all modifications and equivalents of the subject matter described in the claims appended herein, as permitted by applicable law. The present invention may include the following embodiments. [1] Equation (Id) (In the formula, a) R1 is selected from the group consisting of H, C1 - C6 alkyl , C3 - C6 cycloalkyl substituted methyl, benzyl, and -C(O)C1 - C6 alkyl , and R2 is selected from one of the following substituents (i) and (ii); or b) R1 is selected from one of the following substituents (i) and (ii), and R2 is selected from the group consisting of H, C1 - C6 alkyl , C3 -C6 cycloalkyl substituted methyl, benzyl and -C(O)C1 - C6 alkyl ; or c) R1 and R2 are independently selected from the following substituents (i) and (ii); or d) Both R1 and R2 are represented by the following substituents (i); or e) Both R1 and R2 are represented by the following substituent (ii): Here, * indicates a connection point; The carbon atom at the bond site on substituent (i) is in an S configuration; R3 is selected from H, C1 - C6 alkyl and benzyl; R4 is selected from H, -C(O)C1 - C6 alkyl and -C(O)phenyl; However, provided that if both R3 and R4 in substituent (i) are H, then R1 and R2 cannot both be substituent (i); and (If one of R1 and R2 is substituent (i), and both R3 and R4 in that substituent are H, then the other of R1 and R2 cannot be H.) The compounds described or their pharmaceutically acceptable salts. [2] Equation (Id) (In the formula, a) R1 is selected from the group consisting of H, C1 - C6 alkyl , C3 - C6 cycloalkyl substituted methyl, benzyl, and -C(O)C1 - C6 alkyl , and R2 is selected from one of the following substituents (i) and (ii); or b) R1 is selected from one of the following substituents (i) and (ii), and R2 is selected from the group consisting of H, C1 - C6 alkyl , C3 -C6 cycloalkyl substituted methyl, benzyl and -C(O)C1 - C6 alkyl ; or c) R1 and R2 are independently selected from the following substituents (i) and (ii); or d) Both R1 and R2 are represented by the following substituents (i); or e) Both R1 and R2 are represented by the following substituent (ii): Here, * indicates a connection point; The carbon atom at the bond site on substituent (i) is in an S configuration; R3 is selected from H, C1 - C6 alkyl and benzyl; R4 is selected from H, -C(O)C1 - C6 alkyl and -C(O)phenyl; However, provided that if both R3 and R4 in substituent (i) are H, then R1 and R2 cannot both be substituent (i); and (If one of R1 and R2 is substituent (i), and both R3 and R4 in that substituent are H, then the other of R1 and R2 cannot be H.) The compounds described in or their pharmaceutically acceptable salts, However, the compound of formula (Id) above is the following compound (2S,3R,4S,5S,6S)-2-(((4aR,10aR)-7-acetoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate, (2S,3R,4S,5S,6S)-2-(((4aR,10aR)-6-acetoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-7-yl)oxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate, and Methyl(2S,3S,4S,5R,6S)-6-[[(4aR,10aR)-1-propyl-6-[(2S,3R,4S,5S,6S)-3,4,5-triacetoxy-6-methoxycarbonyl-tetrahydropyran-2-yl]oxy-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinoline-7-yl]oxy]-3,4,5-triacetoxy-tetrahydropyran-2-carboxylate A compound or a pharmaceutically acceptable salt thereof, provided that it is not one of the following. [3] R1 is H and R2 is substituent (i); or R1 is substituent (i) and R2 is H; or Both R1 and R2 are represented by substituent (i); Here, R3 is selected from H, C1 -C6 alkyl and benzyl; and R4 is selected from H, -C(O)C1 - C6 alkyl and -C(O)phenyl; The compound according to claim 1 or 2, or a pharmaceutically acceptable salt thereof, provided that R3 and R4 are not both H. [4] R1 is H and R2 is substituent (ii); or R1 is substituent (ii) and R2 is H; or Both R1 and R2 are represented by substituents (ii); Here, R3 is selected from H, C1 -C6 alkyl and benzyl; and R4 is selected from H, -C(O)C1 - C6 alkyl and -C(O)phenyl, the compound according to claim 1 or 2 or a pharmaceutically acceptable salt thereof. [5] R1 is selected from the group consisting of H, C1 - C4 alkyl , C3 - C6 cycloalkyl substituted methyl, benzyl, and -C(O)C1 - C4 alkyl , or a pharmaceutically acceptable salt thereof, according to any one of claims 1 to 4. [6] R1 is selected from the group consisting of H, C1 - C3 alkyl , and benzyl, and is a compound according to any one of claims 1 to 5 or a pharmaceutically acceptable salt thereof. [7] R2 is selected from the group consisting of H, C1 - C4 alkyl , C3 - C6 cycloalkyl substituted methyl, benzyl, and -C(O)C1 - C4 alkyl , or a pharmaceutically acceptable salt thereof, according to any one of claims 1 to 6. [8] R2 is selected from the group consisting of H, C1 - C3 alkyl , and benzyl, and is a compound according to any one of claims 1 to 6 or a pharmaceutically acceptable salt thereof. [9] R3 is selected from H, C1 - C4 al