Aminocyclohexyl ether compounds and uses thereof
Aminocyclohexyl ether compounds are disclosed. The compounds of the present invention may be incorporated in compositions and kits. The present invention also discloses uses for the compounds and compositions, including the treatment of arrhythmia.
1. A method of making compound (5RRR) or compound (5SSR):
wherein the method comprises the steps of:
a) reacting
with (Boc) 2 O under suitable conditions to form compound (1R):
b) reacting compound (1R) with benzyl bromide under suitable conditions to form compound (2R):
c) hydrolyzing compound (2R) under suitable conditions to form compound (3R):
d) reacting compound (3R) with
under suitable conditions to form compound (4R):
e) reacting compound (4R) with
under suitable conditions to form compound (5R);
f) resolving compound (5R) under suitable conditions to form compound (5RRR) and compound (5SSR).
2. The method of claim 1 further comprising the step of:
reacting compound (5RRR) with acetyl chloride under suitable conditions to form compound (17):
3. A method of making compound (5R):
wherein the method comprises the steps of:
a) reacting
with (Boc) 2 O under suitable conditions to form compound (1R):
b) reacting compound (1R) with benzyl bromide under suitable conditions to form compound (2R):
c) hydrolyzing compound (2R) under suitable conditions to form compound (3R):
d) reacting compound (3R) with
under suitable conditions to form compound (4R):
and
e) reacting compound (4R) with
under suitable conditions to form compound (5R).
4. The method of claim 3 further comprising the step of:
hydrolyzing compound (5R) under suitable conditions to form compound (4):
5. The method of claim 3 further comprising the step of:
reacting compound (5R) with hydrogen chloride under suitable conditions to form compound (12):
6. A method of making compound (1):
wherein the method comprises the step of hydrogenolyzing compound (5RRR):
under suitable conditions to form compound (1).
7. The method of claim 6 further comprising, prior to the hydrogenolyzing step, the step of:
resolving compound (5R):
under suitable conditions to form compound (5RRR).
8. The method of claim 7 further comprising, prior to the resolving step, the step of:
reacting compound (4R):
with
under suitable conditions to form compound (5R).
9. The method of claim 8 further comprising, prior to the reacting step, the step of:
reacting compound (3R):
with
under suitable conditions to form compound (4R).
10. The method of claim 9 further comprising, prior to the reaction of compound (3R) with
the step of hydrolyzing compound (2R):
under suitable conditions to form compound (3R).
11. A method of making compound (2):
wherein the method comprises the step of hydrogenolyzing compound (5SSR):
under suitable conditions to form compound (2).
12. The method of claim 11 further comprising, prior to the hydrogenolyzing step, the step of:
resolving compound (5R):
under suitable conditions to form compound (5SSR).
13. The method of claim 12 further comprising, prior to the resolving step, the step of:
reacting compound (4R):
with
under suitable conditions to form compound (5R).
14. The method of claim 13 further comprising, prior to the reacting step, the step of:
reacting compound (3R):
with
under suitable conditions to form compound (4R).
15. The method of claim 14 further comprising, prior to the reaction of compound (3R) with
the step of hydrolyzing compound (2R):
under suitable conditions to form compound (3R).
16. The compound (5RRR):
17. The compound (5SSR):
18. The compound (5R):