Salts of cycloserine compounds and applications thereof
The present invention relates to salts of formula [A][B], wherein [A] is a cation form of a cycloserine compound and [B] is an anion form of a compound of Formula (I): wherein the ratio between the cycloserine compound and the compound of formula (I) ranges from 10:1 to 1:10. The salts described herein have improved properties, including greatly increased stability and decreased hygroscopicity. Also provided in the present invention are methods for treating and/or reducing the risk of a neuropsychiatric disorder and/or a bacterial infectious disease (e.g., tuberculosis), comprising administering a subject in need a composition comprising salts of formula [A][B] described herein.
1. A salt of formula [A][B],
wherein [A] is a cation form of a cycloserine compound; and
[B] is an anion form of a compound of formula (I):
in which
X is —NH 2 or —OH;
each of L 1 and L 2 , independently, is C 1-6 alkylene, C 2-6 alkenylene, or C 2-6 alkynylene, or one of L 1 and L 2 is N, O, or S, and the other one is C 1-6 alkylene, C 2-6 alkenylene, or C 2-6 alkynylene, as valency permits;
is either a single or double bond; and
wherein the ratio of [A] and [B] in the salt ranges from 5:1 to 1:5.
2. The salt of claim 1 , wherein the cycloserine compound is of formula:
3. The salt of claim 2 , wherein the compound of formula (I) is of formula:
wherein:
each instance of A and B, independently, is —NH 2 , —OH, or —H;
and C 1 C 2 is —C 1 -C 2 - or —C 2 ═C 1 -.
4. The salt of claim 3 , wherein the compound of formula (Ia) is of formula:
wherein
each instance of A and B, independently, is —OH or —H.
5. A salt of formula [A][B],
wherein:
[A] is a cation form of a cycloserine compound; and
[B] is an anion form of a compound selected from the group consisting of:
and
wherein the ratio between [A] and [B] ranges from 5:1 to 1:1.
6. The salt of claim 5 , wherein [B] is an anion form of a compound of formula
and the ratio between [A] and [B] is 4:1.
7. The salt of claim 5 , wherein [B] is an anion form of a compound of formula
and the ratio between [A] and [B] is 2:1.
8. The salt of claim 5 , wherein [B] is an anion form of a compound of formula
and the ratio between [A] and [B] is 1:1.
9. A salt of formula [A][B],
wherein [A] is a cation form of a cycloserine compound; and
[B] is an anion form of a compound of formula (Ic):
wherein A and B, independently, is —OH or —H; and wherein the ratio between [A] and [B] ranges from 5:1 to 1:1.
10. The salt of claim 9 , wherein the compound of formula (Ic) is selected from the group consisting of
11. The salt of claim 10 , wherein the compound of formula (Ic) is
and the ratio between [A] and [B] is 1:1.
12. A composition comprising the salt of claim 5 and a carrier.
13. A composition comprising the salt of claim 9 and a carrier.
14. The composition of claim 12 , wherein the composition is a pharmaceutical composition, a nutraceutical composition, a health food, or a medical food.
15. The composition of claim 13 , wherein the composition is a pharmaceutical composition, a nutraceutical composition, a health food, or a medical food.