Menaquinol compositions and methods of treatment
The present application discloses methods for the efficient preparation of high purity compounds of the Formula I, and their methods of use. Also disclosed herein are pharmaceutical compositions comprising a therapeutically effective amount of a menaquinol compound as disclosed above, or a mixture thereof, and a pharmaceutically acceptable excipient, wherein the composition is effective for the treatment of a condition associated with vitamin K selected from for the treatment of osteoporosis and arteriosclerosis.
1. A menaquinol compound of the Formula I:
wherein:
m is 7, 8, 9 or 10;
R 1 and R 2 are both the residue 15;
R 1 and R 2 are both the residue 16;
R 1 and R 2 are both the residue 17;
R 1 and R 2 are both the residue 18;
R 1 and R 2 are both the residue 20;
R 1 and R 2 are both the residue 21;
R 1 and R 2 are both the residue 22;
R 1 and R 2 are both the residue 23;
R 1 and R 2 are both the residue 24;
R 1 and R 2 are both the residue 25;
R 1 and R 2 are both the residue 26;
R 1 and R 2 are both the residue 27;
R 1 and R 2 are both the residue 28;
R 1 is H and R 2 is the residue 15; R 2 is H and R 1 is the residue 15;
R 1 is H and R 2 is the residue 16; R 2 is H and R 1 is the residue 16;
R 1 is H and R 2 is the residue 17; R 2 is H and R 1 is the residue 17;
R 1 is H and R 2 is the residue 18; R 2 is H and R 1 is the residue 18;
R 1 is H and R 2 is the residue 20; R 2 is H and R 1 is the residue 20;
R 1 is H and R 2 is the residue 21; R 2 is H and R 1 is the residue 21;
R 1 is H and R 2 is the residue 22; R 2 is H and R 1 is the residue 22;
R 1 is H and R 2 is the residue 23; R 2 is H and R 1 is the residue 23;
R 1 is H and R 2 is the residue 24; R 2 is H and R 1 is the residue 24;
R 1 is H and R 2 is the residue 25; R 2 is H and R 1 is the residue 25;
R 1 is H and R 2 is the residue 26; R 2 is H and R 1 is the residue 26;
R 1 is H and R 2 is the residue 27; R 2 is H and R 1 is the residue 27; and
R 1 is H and R 2 is the residue 28; R 2 is H and R 1 is the residue 28;
2. The compound of claim 1 of the Formula I, wherein:
R 1 and R 2 are both the residue 15;
R 1 and R 2 are both the residue 16;
R 1 and R 2 are both the residue 17;
R 1 and R 2 are both the residue 18;
R 1 and R 2 are both the residue 20;
R 1 and R 2 are both the residue 21;
R 1 and R 2 are both the residue 22;
R 1 and R 2 are both the residue 23;
R 1 and R 2 are both the residue 24;
R 1 and R 2 are both the residue 25;
R 1 and R 2 are both the residue 26;
R 1 and R 2 are both the residue 27; and
R 1 and R 2 are both the residue 28.
3. The compound of claim 1 of the Formula I, wherein:
R 1 is H and R 2 is the residue 15; R 2 is H and R 1 is the residue 15;
R 1 is H and R 2 is the residue 16; R 2 is H and R 1 is the residue 16;
R 1 is H and R 2 is the residue 17; R 2 is H and R 1 is the residue 17;
R 1 is H and R 2 is the residue 18; R 2 is H and R 1 is the residue 18;
R 1 is H and R 2 is the residue 20; R 2 is H and R 1 is the residue 20;
R 1 is H and R 2 is the residue 21; R 2 is H and R 1 is the residue 21;
R 1 is H and R 2 is the residue 22; R 2 is H and R 1 is the residue 22;
R 1 is H and R 2 is the residue 23; R 2 is H and R 1 is the residue 23;
R 1 is H and R 2 is the residue 24; R 2 is H and R 1 is the residue 24;
R 1 is H and R 2 is the residue 25; R 2 is H and R 1 is the residue 25;
R 1 is H and R 2 is the residue 26; R 2 is H and R 1 is the residue 26;
R 1 is H and R 2 is the residue 27; R 2 is H and R 1 is the residue 27; and
R 1 is H and R 2 is the residue 28; R 2 is H and R 1 is the residue 28.
4. The menaquinol compound of the Formula I of claim 1 , wherein
m is 7, 8, 9 or 10;
R 1 is H and R 2 is the acyl residue of caffeic acid 20: or
R 2 is H and R 1 is the acyl residue of caffeic acid 20;
5. The menaquinol compound of the Formula I of claim 1 , wherein
m is 7, 8, 9 or 10;
R 1 is H and R 2 is or the acyl residue of ferulic acid 21; or
R 2 is H and R 1 is the acyl residue of ferulic acid 21;
6. The menaquinol compound of the Formula I of claim 1 , wherein
m is 7, 8, 9 or 10;
R 1 is H and R 2 is the acyl residue of chlorogenic acid 22; or
R 2 is H and R 1 is the acyl residue of chlorogenic acid 22;
7. The menaquinol compound of the Formula I of claim 1 , wherein
m is 7, 8, 9 or 10;
R 1 is H and R 2 is the acyl residue of quinic acid 23; or
R 2 is H and R 1 is the acyl residue of quinic acid 23;