Process for the manufacturing of (6AR,10AR)-7-propyl-6,6A,7,8,9,10,10A,11-octahydro-[1,3]dioxolo[4′,5′:5,6]benzo[1,2-G]quinoline and (4AR, 10AR)-1-propyl-1,2,3,4,4A,5,10,10A-octahydro-benzo[G]quinoline-6,7-diol
The present invention relates to a new process for manufacturing (6aR,10aR)-7-propyl-6,6 a,7,8,9,10,10a,11-octahydro-[1,3]dioxolo[4′,5′:5,6]benzo[1,2-g]quinoline with formula (Ib) below, (4aR,10aR)-1-Propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline-6,7-diol with formula (I) below and salts thereof. Both compounds are for use in the treatment of neurodegenerative diseases and disorders such as Parkinson's Disease. The invention also relates to new intermediate compounds of said process.
1. A compound selected from the compounds of formula (A2), formula (A3), formula (a2i), and formula (a2ii):
or a salt or solvate thereof.
2. A salt of the compound of claim 1 .
3. The salt of claim 2 , wherein the salt is a pharmaceutically acceptable salt.
4. The salt of claim 3 , wherein the pharmaceutically acceptable salt is a hydrochloric acid, hydrobromic acid, phosphoric acid, nitrous acid, sulphuric acid, benzoic acid, citric acid, gluconic acid, lactic acid, maleic acid, succinic acid, tartaric acid, acetic acid, propionic acid, oxalic acid, malonic acid, fumaric acid, glutamic acid, pyroglutamic acid, salicylic acid, gentisic acid, saccharin, or sulfonic acid.
5. A solvate of the compound of claim 1 .
6. The solvate of claim 5 , wherein the solvent is ethanol or water.
7. The compound of claim 1 , wherein the compound is of formula (A2):
or a salt or solvate thereof.
8. A salt of the compound of claim 7 .
9. A hemi-L-tartrate salt of the compound of claim 7 .
10. The freebase of the compound of claim 7 .
11. The compound of claim 1 , wherein the compound is of formula (A3):
or a salt or solvate thereof.
12. A salt of the compound of claim 11 .
13. The freebase of the compound of claim 11 .
14. The compound of claim 1 , wherein the compound is of formula (a2i):
or a salt or solvate thereof.
15. A salt of the compound of claim 14 .
16. The compound of claim 1 , wherein the compound is of formula (a2ii):
or a salt or solvate thereof.
17. A salt of the compound of claim 16 .
18. The salt of claim 4 , wherein the sulfonic acid is methanesulfonic acid, ethanesulfonic acid, toluenesulfonic acid, naphthalene-2-sulphonic acid, 2-hydroxy ethanesulphonic acid, or benzenesulfonic acid.