Haptens of risperidone and paliperidone
The invention relates to compounds of Formula I, wherein R 1 and R 2 are defined in the specification, useful for the synthesis of novel conjugates and immunogens derived from risperidone and paliperidone. The invention also relates to conjugates of a risperidone or paliperidone hapten and a protein.
1. The compound of Formula I
wherein:
R 1 is H, or OH;
R 2 is O(CH 2 ) r NH 2 ,
O(CH 2 ) r NHC(O)(CH 2 ) m CO 2 H, or Z—(Y) p -G;
wherein:
Z is selected from the group consisting of:
—N(R 4 )—, —O—, —S—, -heteroalkyl-;
R 4 is H, an alkyl group, cycloalkyl group, aralkyl group or substituted or unsubstituted aryl group;
Y is an organic spacer group;
G is a functional linking group capable of binding to a carrier;
p is 0, or 1;
r is 1, 2, 3, 4, or 5;
m is 1, 2, 3, 4, or 5;
n is 1, 2, 3, 4, or 5.
2. The compound of claim 1
wherein:
R 1 is H, or OH;
R 2 is O(CH 2 ) r NH 2 ,
O(CH 2 ) r NHC(O)(CH 2 ) m CO 2 H, or Z—(Y) p -G;
wherein:
Z is O;
Y is an organic spacer group;
G is a functional linking group capable of binding to a carrier;
p is 0, or 1;
r is 1, 2, 3, 4, or 5;
m is 1, 2, 3, 4, or 5;
n is 1, 2, 3, 4, or 5.
3. The compound of claim 1
wherein:
R 1 is H, or OH;
R 2 is O(CH 2 ) r NH 2 ,
O(CH 2 ) r NHC(O)(CH 2 ) m CO 2 H, or Z—(Y) p -G;
wherein:
Z is O(CH 2 ) r NH;
Y is an organic spacer group;
G is a functional linking group capable of binding to a carrier;
p is 0, or 1;
r is 1, 2, 3, 4, or 5;
m is 1, 2, 3, 4, or 5;
n is 1, 2, 3, 4, or 5.
4. The compound of claim 3
wherein:
p is 1;
r is 2,
m is 1, 2, 3, 4, or 5;
n is 1, 2, 3, 4, or 5.
5. The compound of claim 3
wherein
R 1 is H, or OH;
R 2 is O(CH 2 ) r NH 2 ,
or
O(CH 2 ) r NHC(O)(CH 2 ) m CO 2 H;
wherein:
r is 2;
m is 1, 2, 3, or 4; and
n is 1, or 2.
6. The compound of claim 5 , wherein
R 1 is H, or OH; and
R 2 is O(CH 2 ) r NH 2 , or
r is 2;
m is 1.
7. The compound of claim 1 , selected from the group consisting of
8. A conjugate of a compound of claim 1 and an immunogenic carrier.
9. The conjugate of claim 8 , where said immunogenic carrier is a protein.
10. The conjugate of claim 9 , where said protein is keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.
11. A conjugate of the compound of claim 2 and an immunogenic carrier.
12. A conjugate of the compound of claim 3 and an immunogenic carrier.
13. A conjugate of the compound of claim 4 and an immunogenic carrier.
14. A conjugate of the compound of claim 5 and an immunogenic carrier.
15. A conjugate of the compound of claim 6 and an immunogenic carrier.
16. The conjugate of claim 8 wherein the compound is
17. The conjugate of claim 16 , where said immunogenic carrier is a protein.
18. The conjugate of claim 17 , where said protein is keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.