Haptens of olanzapine
The invention relates to compounds of Formula I, wherein R 1 , R 2 , and R 3 are defined in the specification, useful for the synthesis of novel conjugates and immunogens derived from olanzapine. The invention also relates to conjugates of an olanzapine hapten and a protein.
1. The compound of Formula I:
wherein:
R 1 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 3 is H; provided that either R 1 or R 2 must be H, and further provided that R 1 and R 2 may not all be H simultaneously;
m is 1, 2, 3, 4, or 5; and
n is 1, 2, 3, 4, or 5.
2. The compound of claim 1 :
wherein:
R 1 is
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H;
R 3 is H;
m is 1, 2, 3, 4, or 5; and
n is 1, 2, 3, 4, or 5.
3. The compound of claim 1
wherein:
R 1 is H,
R 2 is
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 3 is H;
m is 1, 2, 3, 4, or 5; and
n is 1, 2, 3, 4, or 5.
4. The compound of claim 1
wherein:
R 1 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H; provided that either R 1 or R 2 must be H, and further provided that both R 1 and R 2 may not be H simultaneously;
R 3 is H;
m is 1, 2, 3, 4, or 5; and
n is 1, 2, 3, 4, or 5.
5. The compound of claim 1
wherein:
R 1 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H; provided that either R 1 or R 2 must be H, and further provided that both R 1 and R 2 may not be H simultaneously;
R 3 is H;
m is 1, 2, 3, 4, or 5; and n is 1, 2, 3, 4, or 5.
6. The compounds of claim 1 , selected from the group consisting of:
7. The compound of claim 6 which is:
8. The compound of claim 6 which is:
9. A conjugate of the compound of claim 1 and an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
10. A conjugate of the compound of claim 2 and an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
11. A conjugate of the compound of claim 3 and an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
12. A conjugate of the compound of claim 4 and an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
13. A conjugate of the compound of claim 5 and an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
14. The conjugate of claim 9 wherein the compound is:
15. The conjugate of claim 9 wherein the compound is:
16. The conjugate of claim 9 wherein the compound is:
17. The conjugate of claim 9 wherein the compound is:
18. A product made by the process of contacting a compound of claim 1 with an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
19. A product made by the process of contacting a compound of claim 2 with an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
20. A product made by the process of contacting a compound of claim 3 with an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
21. A product made by the process of contacting a compound of claim 4 with an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
22. A product made by the process of contacting a compound of claim 5 with an immunogenic carrier, wherein the immunogenic carrier is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
23. The product of claim 18 wherein the compound is:
24. The product of claim 18 wherein the compound is:
25. The product of claim 18 wherein the compound is:
26. The product of claim 18 wherein the compound is:
27. The compound of claim 1
wherein:
R 1 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H; provided that either R 1 or R 2 must be H, and further provided that both R 1 and R 2 may not be H simultaneously;
R 3 is H;
m is 1, 2, 3, 4, or 5; and
n is 1, 2, 3, 4, or 5.
28. A conjugate of the compound of claim 27 and an immunogenic carrier, wherein the immunogenic carrier is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.
29. A product made by the process of contacting a compound of claim 27 with an immunogenic carrier, wherein the immunogenic carrier is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.