Trehalose compound, method for producing same, and pharmaceutical product containing the compound
A trehalose compound having high immunopotentiating activity and low toxicity is represented by formula (1). (In the formula, X and X′ each represents a phenyl, a naphthyl, R 1 —CHR 1 — (wherein R 1 and R 2 each represents a C 7 -C 21 alkyl group or the like) or the like; and n and n′ each independently represents an integer of 0-3). The compound exhibits a high activating effect on macrophages and neutrophils.
1. A compound represented by the following formula (1):
wherein X represents phenyl, naphthyl, or a group represented by R 1 —CHR 2 —, and X′ represents phenyl, naphthyl, or a group represented by R 1 ′—CHR 2 ′—,
wherein R 1 , R 1 ′, R 2 and R 2 ′ independently represent a hydrogen atom or a C 1 -C 21 alkyl group, and with regard to R 1 , R 1 ′, R 2 and R 2 ′, a hydrogen atom in each alkyl group may be replaced by an alkoxy group, all or some of alkyl groups may form a 4- to 8-membered ring, and R 1 and R 2 , and R 1 ′ and R 2 ′ may bind to each other to form a 4- to 8-membered ring, and
wherein n and n′ independently represent an integer of 0 to 3,
with the proviso that the compound is not the following compounds:
(1) a compound, in which X represents R 1 —CHR 2 —, X′ represents R 1 ′—CHR 2 ′—, R 1 , R 1 ′, R 2 and R 2 ′ independently represent a hydrogen atom or an unsubstituted linear C 1 -C 6 alkyl group, and n and n′ represent 0;
(2) a compound, in which X represents R 1 —CHR 2 —, X′ represents and any one of R 1 ′—CHR 2 ′—, R 1 , R 1 ′, R 2 and R 2 ′ represent a C 14 linear alkyl group, and n and n′ represent 0;
(3) a compound, in which X represents R 1 —CHR 2 —, X′ represents R 1 ′—CHR 2 ′—, all of R 1 , R 1 ′, R 2 and R 2 ′ represent a hydrogen atom, and n and n′ independently represent 0 to 3;
(4) a compound, in which X represents R 1 —CHR 2 —, X′ represents R 1 ′—CHR 2 ′—, any three of R 1 , R 1 ′ R 2 and represent a hydrogen atom, the remaining one of R 1 , R 1 ′, R 2 and R 2 ′ represents a C 1 -C 21 linear alkyl group, and n and n′ independently represent 0 to 3.
(5) a compound, in which X represents R 1 —CHR 2 —, X′ represents R 1 ′—CHR 2 ′—, any one of R 1 and R 2 represents a hydrogen any one of R 1 ′ and R 2 ′ represents a hydrogen atom, and both the remaining one of R 1 and R 2 and the remaining one of R 1 ′ and R 2 ′ independently represent a C 1 -C 21 linear alkyl group, and n and n′ independently represent 0 to 3; and
(6) a compound, in which X represents phenyl, X′ represents phenyl, and n and n′ represent 0.
2. The compound according to claim 1 , wherein X represents R 1 —CHR 2 — and X′ represents R 1 ′—CHR 2 ′—.
3. The compound according to claim 2 , wherein R 1 , R 1 ′, R 2 and R 2 ′ independently represent a linear C7-C12 and C16-C21 alkyl group, and n and n′ independently represent 0 or 1.
4. The compound according to claim 2 , wherein R 1 , R 1 ′, R 2 and R 2 ′ independently represent a linear C7-C12′ and C16 alkyl group, and n and n′ independently represent 0.
5. The compound according to claim 2 , wherein R 1 , R 1 ′, R 2 and R 2 ′ independently represent a linear C 9 -C 14 alkyl group, and n and n′ independently represent 1.
6. The compound according to claim 1 , wherein R 1 is identical to R 1 ′, R 2 is identical to R 2 ′, and n is identical to n′.
7. The compound according to claim 1 , which is any of the following compounds:
6,6′-bis-O-(2-octyldecanoyl)-α,α′-trehalose,
6,6′-bis-O-(2-nonylundecanoyl)-α,α′-trehalose,
6,6′-bis-O-(2-decyldodecanoyl)-α,α′-trehalose,
6,6′-bis-O-(2-undecyltridecanoyl)-α,α′-trehalose,
6,6′-bis-O-(2-dodecyltetradecanoyl)-α,α′-trehalose,
6,6′-bis-O-(2-tridecylpentadecanoyl)-α,α′-trehalose,
6,6′-bis-O-(2-pentadecylheptadecanoyl)-α,α′-trehalose, and
6,6′-bis-O-(2-hexadecyloctadecanoyl)-α,α′-trehalose.
8. The compound according to claim 1 , which is any of the following compounds:
6,6′-bis-O-(3-nonyldodecanoyl)-α,α′-trehalose,
6,6′-bis-O-(3-decyltridecanoyl)- α,α′-trehalose,
6,6′-bis-O-(3-undecyltetradecanoyl)-α,α′-trehalose,
6,6′-bis-O-(3-dodecylpentadecanoyl)-α,α′-trehalose,
6,6′-bis-O-(3-tridecylhexadecanoyl)-α,α′-trehalose, and
6,6′-bis-O-(3-tetradecylheptadecanoyl)-α,α′-trehalose.
9. The compound according to claim 1 , which is any of the following compounds:
6,6′-bis-O-(2-decyldodecanoyl)-α,α′-trehalose,
6,6′-bis-O-(3-nonyldodecanoyl)-α,α′-trehalose,
6,6′-bis-O-(3-tridecylhexadecanoyl)-α,α′-trehalose, and
6,6′-bis-O-(3-tetradecylheptadecanoyl)-α,α′-trehalose.
10. A pharmaceutical composition comprising the compound according to claim 1 and a pharmaceutically acceptable carrier.
11. A pharmaceutical composition comprising the compound according to claim 2 and a pharmaceutically acceptable carrier.
12. A pharmaceutical composition comprising the compound according to claim 3 and a pharmaceutically acceptable carrier.
13. A pharmaceutical composition comprising the compound according to claim 4 and a pharmaceutically acceptable carrier.