JP-2022533912-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] Formula (Id) (In the formula, R1, R2, and R3 are determined according to a) or b) below: a) R1 and R2 are independently H, C1 - C6 alkyl , benzyl and the following substituents (i) (In the formula, * indicates a bonding point.) Selected from, and R3 does not exist. However, this is subject to the condition that neither R1 nor R2 can be H; or b) Both R1 and R2 are H, and R3 is one of the following substituents (ii) (In the formula, * indicates a bonding point); Therefore, N is positively charged. Here, R4 and R5 are independently selected from H, C1 - C6 alkyl , phenyl, benzyl, C3 - C6 cycloalkyl , and methyl substituted with C3 -C6 cycloalkyl . The compounds described or their pharmaceutically acceptable salts. [2] The compound is given by formula (Ie) (wherein R1 and R2 are independently H, C1 - C6 alkyl , benzyl and substituent (i) (In the formula, * indicates a bonding point; R4 and R5 are each independently selected from H, C1 - C6 alkyl , phenyl, benzyl, C3 - C6 cycloalkyl , and methyl substituted with C3 -C6 cycloalkyl . Selected from; (However, this is subject to the condition that neither R1 nor R2 can be H.) A compound of the compound described in claim 1 or a pharmaceutically acceptable salt thereof. [3] The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R1 is H, R2 is substituent (i), and R3 is absent. [4] The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R1 is substituent (i), R2 is H, and R3 is absent. [5] The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are both represented by substituent (i), and R3 is absent. [6] R1 and R2 are both H; and R3 is substituent (ii), the compound according to claim 1 or a pharmaceutically acceptable salt thereof. [7] A compound according to any one of claims 1 to 6 or a pharmaceutically acceptable salt thereof, wherein R4 and R5 are both H. [8] A compound according to any one of claims 1 to 6 or a pharmaceutically acceptable salt thereof, wherein at least one of R4 and R5 is benzyl. [9] The compound, (4aR,10aR)-6,7-bis(benzyloxy)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline; (4aR,10aR)-7-(benzyloxy)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-ol; (4aR,10aR)-7-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-ol; Benzyl((4aR,10aR)-6-((bis(benzyloxy)phosphoryl)oxy)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-7-yl)hydrogen phosphate; Benzyl((4aR,10aR)-7-((bis(benzyloxy)phosphoryl)oxy)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yl)hydrogen phosphate; (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6,7-diirbis(dihydrogen phosphate); Benzyl((4aR,10aR)-7-(benzyloxy)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yl)hydrogen phosphate; (4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yldihydrogen phosphate; and ((1S,4aR,10aR)-6,7-dihydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-1-ium-1-yl)methylhydrogen phosphate A pharmaceutically acceptable salt of the compound described in claim 1 or any of the said compounds, selected from the group consisting of the following. [10] The compound, Compound (2): (4aR,10aR)-7-(benzyloxy)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-ol; Compound (3): (4aR,10aR)-7-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-ol; Compound (6): (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6,7-diirbis(dihydrogen phosphate); Compound (8): (4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yldihydrogen phosphate; and Compound (9): ((1S,4aR,10aR)-6,7-dihydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-1-ium-1-yl)methylhydrogen phosphate A pharmaceutically acceptable salt of the compound described in claim 1 or any of the said compounds, selected from the group consisting of the following. [11] Compound (2): (4aR,10aR)-7-(benzyloxy)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-ol; Compound (3): (4aR,10aR)-7-methoxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-ol A pharmaceutically acceptable salt of the compound described in claim 1 or any of the said compounds, selected from the group consisting of the following. [12] Compound (6): (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6,7-diirbis(dihydrogen phosphate); Compound (8): (4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-6-yldihydrogen phosphate; and Compound (9): ((1S,4aR,10aR)-6,7-dihydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-1-ium-1-yl)methylhydrogen phosphate A pharmaceutically acceptable salt of the compound described i