AMINOMETHYL CARBAMATE COMPOUNDS AND DERIVATIVES AND METHODS OF THEIR MAKING

1 . A process for preparation of a compound of Formula (I):

wherein

R 1 is C 1 -C 6 alkyl;

R 2 is independently selected from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl, wherein C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl can be optionally substituted from 1 to 3 times with a substituent selected independently at each occurrence from the group consisting of C 1 -C 6 alkyl, OH, halogen, and C 1 -C 6 alkoxy;

R 3 is independently selected at each occurrence thereof from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl;

R 4 is independently selected at each occurrence thereof from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl;

R 5 is selected from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl, wherein C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl can be optionally substituted from 1 to 3 times with a substituent selected independently at each occurrence from the group consisting of —OC 1 -C 6 alkyl, —C(O)OH, and —C(O)OC 1 -C 6 alkyl;

R 6 is selected from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl, wherein C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl can be optionally substituted from 1 to 3 times with a substituent selected independently at each occurrence from the group consisting of —OC 1 -C 6 alkyl, —C(O)OH, and —C(O)OC 1 -C 6 alkyl;

X is halogen, mesylate, tosylate, or triflate;

n is 0, 1, 2, 3, 4, 5, or 6;

m is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; and

p is 0, 1, 2, 3, or 4;

or a solvate thereof,

said process comprising:

providing an intermediate compound of Formula (IVa) and/or Formula (IVb):

wherein Hal is halogen;

reacting the intermediate compound of Formula (IVa) and/or Formula (IVb) with an alkylating agent to produce an intermediate compound of Formula (II) having the structure:

and

reacting the intermediate compound of Formula (II) with a compound of Formula (III):

to produce the compound of Formula (I).

2 . The process according to claim 1 , wherein n is 0 or 1.

3 . (canceled)

4 . The process according to claim 1 , wherein R 1 is methyl.

5 . The process according to claim 1 , wherein R 5 is H.

6 . The process according to claim 1 , wherein the compound of Formula I has the structure selected from the group consisting of

7 .- 8 . (canceled)

9 . The process according to claim 1 , wherein the compound of Formula (II) has the structure selected from the group consisting of:

10 . (canceled)

11 . The process according to claim 1 , wherein the compound of Formula (III) has the structure selected from the group consisting of:

12 . (canceled)

13 . The process according to claim 1 , wherein said reacting the intermediate compound of Formula (II) with the compound of Formula (III) is carried out at a temperature of from about 25° C. to about 80° C.

14 . (canceled)

15 . The process according to claim 1 , wherein said forming the intermediate compound of Formula (II) comprises:

(i) reacting the intermediate compound of Formula (IVa) with an alkylating agent to produce the intermediate compound of Formula (II); or

(ii) reacting the intermediate compound of Formula (IVb) with an alkylating agent to produce the intermediate compound of Formula (II); or

(iii) reacting a mixture of the intermediate compounds of Formula (IVa) and Formula (IVb) with an alkylating agent to produce the intermediate compound of Formula (II).

16 .- 17 . (canceled)

18 . The process according to claim 1 , wherein the alkylating agent is SOCl 2 /C 1-6 alkyl-OH.

19 . The process according to claim 1 , wherein the intermediate compound of Formula (IVa) has the structure selected from the group consisting of:

20 . (canceled)

21 . The process according to claim 1 , wherein the intermediate compound of Formula (IVb) is

22 . (canceled)

23 . The process according to claim 1 further comprising:

providing a compound of Formula (V):

and

forming the intermediate compound of Formula (IVa) and/or (IVb) from the compound of Formula (V).

24 . The process according to claim 23 , wherein said forming the intermediate compound of Formula (IVa) and/or (IVb) comprises:

reacting the compound of Formula (V) with a compound of Formula (VI):

wherein LG is a suitable leaving group.

25 . The process according to claim 24 , wherein the compound of Formula (VI) is chloromethyl chloroformate.

26 . The process according to claim 24 , wherein said reacting the compound of Formula (V) with the compound of Formula (VI) is carried out in the presence of a base.

27 . (canceled)

28 . The process according to claim 24 , wherein said reacting the compound of Formula (V) with the compound of Formula (VI) is carried out at a temperature of from about 5° C. to about 25° C.

29 .- 30 . (canceled)

31 . The process according to claim 23 , wherein the compound of Formula (V) is selected from the group consisting of:

or a salt thereof.

32 . (canceled)

33 . A compound of Formula (I):

wherein

R 1 is C 1 -C 6 alkyl;

R 2 is independently selected from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl, wherein C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl can be optionally substituted from 1 to 3 times with a substituent selected independently at each occurrence from the group consisting of C 1 -C 6 alkyl, OH, halogen, and C 1 -C 6 alkoxy;

R 3 is independently selected at each occurrence thereof from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl;

R 4 is independently selected at each occurrence thereof from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl;

R 5 is selected from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl, wherein C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl can be optionally substituted from 1 to 3 times with a substituent selected independently at each occurrence from the group consisting of —OC 1 -C 6 alkyl, —C(O)OH, and —C(O)OC 1 -C 6 alkyl;

R 6 is selected from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl, wherein C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl can be optionally substituted from 1 to 3 times with a substituent selected independently at each occurrence from the group consisting of —OC 1 -C 6 alkyl, —C(O)OH, and —C(O)OC 1 -C 6 alkyl;

X is halogen, mesylate, tosylate, or triflate;

n is 0, 1, 2, 3, 4, 5, or 6;

m is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; and

p is 0, 1, 2, 3, or 4;

or a solvate thereof,

with the proviso that when n is 1; R 1 is Me; m is 0; and p is 0, R 2 is not Ph.

34 . A compound of Formula (II):

and

wherein

Hal is halogen;

R 1 is H or C 1 -C 6 alkyl;

R 2 is independently selected from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl, wherein C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl can be optionally substituted from 1 to 3 times with a substituent selected independently at each occurrence from the group consisting of C 1 -C 6 alkyl, OH, halogen, and C 1 -C 6 alkoxy;

R 3 is independently selected at each occurrence thereof from the group consisting of H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 13 cycloalkylalkyl, heterocyclyl, aryl, and heteroaryl;

n is 0, 1, 2, 3, 4, 5, or 6; and

m is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9;

or a pharmaceutically acceptable salt thereof or a solvate thereof,

with the proviso that when n is 1; R 1 is Me; m is 0; and p is 0, R 2 is not Ph.

35 .- 36 . (canceled)