Non-mucin type synthetic compounds or its carrier conjugated compounds
The purposes of this invention are preparation of the non-mucin type synthetic compounds-carrier conjugated compounds which are stable against enzymes, and which have the ability of specific reactivity to induce immune response for cancer and HIV. A compound of the general formula (1), wherein A represents OH or sialic acid and/or it's derivatives, and B represents OH or galactose and/or it's derivatives; T represents H or protecting groups of amine; M represents H or OH; X represents oxygen atom, —NH— or S(O)z (where z is 0, 1 or 2); Q is H or oxygen atom; V represents lower alkyl or H; W is straight or branched alkylene groups from 0 to 5; Z is straight or branched alkylene groups from 1 to 5; i, m, and t is 0 or 1; non-mucin type synthetic compounds or it's carrier conjugated compounds, which have above mentioned compounds as a core structure of antigen.
1. A compound of the general formula (1),
wherein
A represents OH or sialic acid;
B represents OH or galactose;
T represents H or protecting groups of amine;
M represents H or OH;
X represents oxygen atom, —NH— or S(O) z where z is 0, 1 or 2;
Q is oxygen atom and can be present or not present;
V represents lower alkyl or H;
W is straight or branched alkylene groups from 0 to 5;
Z is straight or branched alkylene groups from 1 to 5; and
i, m, and t is 0 or 1 with the proviso that i and t cannot be both 0.
2. A compound of the general formula (2),
wherein
A represents OH or sialic acid, and
B represents OH or galactose;
T represents H or protecting groups of amine;
X represents oxygen atom, —NH— or S(O) z where z is 0, 1 or 2;
Q is oxygen atom and can be present or not present;
V represents lower alkyl or H;
W is straight or branched alkylene groups from 0 to 5;
Z is straight or branched alkylene groups from 1 to 5;
i, m, and t is 0 or 1 with the proviso that i and t cannot be both 0;
E represents pharmaceutically acceptable carrier compounds;
l is 0 or 1;
F is showed followings,
wherein
J is —CH 2 CH 2 X— or —N(L)-CH 2 CO— where X represents oxygen atom, —NH— or S(O) z where z is 0, 1 or 2;
L is H or lower alkyl;
G is H or lower alkyl;
p is 0 to 3; and
y is 0 or 1.
3. A compound of the general formula (3),
wherein
A represents OH or sialic acid, and
B represents OH or galactose;
T represents H or protecting groups of amine;
X represents oxygen atom, —NH— or S(O) z where z is 0, 1 or 2;
Q is oxygen atom and can be present or not present;
V represents lower alkyl or H;
W is straight or branched alkylene groups from 0 to 5;
Z is straight or branched alkylene groups from 1 to 5;
i, m, and t is 0 or 1;
E represents pharmaceutically acceptable carrier compounds;
l is 0 or 1; and
r is from 1 to 4.
4. A compound of the general formula (4),
wherein
A represents OH or sialic acid, and
B represents OH or galactose;
T represents H or protecting groups of amine;
X represents oxygen atom, —NH— or S(O) z where z is 0, 1 or 2;
Q is oxygen atom and can be present or not present;
V represents lower alkyl or H;
W is straight or branched alkylene groups from 0 to 5;
Z is straight or branched alkylene groups from 1 to 5;
J is —CH 2 CH 2 X— or —N(L)-CH 2 CO— where X represents oxygen atom, —NH— or S(O) z where z is 0, 1 or 2;
i, m, and t is 0 or 1;
p is 0 to 3;
r is from 1 to 4;
U represents H or lower alkyl;
w is 0 to 50; and
y is 1 or 50.
5. The compound thereof of claim 1 , wherein A is sialic acid and B is OH.
6. The compound thereof of claim 2 , wherein A is sialic acid and B is OH.
7. The compound thereof of claim 3 , wherein A is sialic acid and B is OH.
8. The compound thereof of claim 4 , wherein A is sialic acid and B is OH.
9. The compound thereof of claim 1 , wherein A is OH and B is galactose.
10. The compound thereof of claim 2 , wherein A is OH and B is galactose.
11. The compound thereof of claim 3 , wherein A is OH and B is galactose.
12. The compound thereof of claim 4 , wherein A is OH and B is galactose.
13. The compound thereof of claim 1 , wherein both A and B are OH.
14. The compound thereof of claim 2 , wherein both A and B are OH.
15. The compound thereof of claim 3 , wherein both A and B are OH.
16. The compound thereof of claim 4 , wherein both A and B are OH.