Haptens of aripiprazole
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 aripiprazole. The invention also relates to conjugates of an aripiprazole hapten and a protein.
1. A conjugate of the compound of Formula I and an immunogenic carrier:
wherein:
R 1 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
NH 2 , or 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 be H simultaneously;
m is 1, 2, 3, 4, or 5; and
n is 1, 2, 3, 4, or 5.
2. The conjugate 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,
NH 2 , or 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 or 4; and
n is 1, 2, 3, 4, or 5.
3. The conjugate 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,
NH 2 , or 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 both R 1 and R 2 may not be H simultaneously;
m is 1, 2, 3, 4, or 5; and
n is 1, 2, 3, 4, or 5.
4. The conjugate of claim 1 wherein:
R 1 is H,
CH 2 NH 2 , CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
NH 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, or 3; and
n is 1, 2, or 3.
5. The conjugate of claim 1 , wherein the compound is
6. The conjugate of claim 5 , wherein the immunogenic carrier is a protein.
7. The conjugate of claim 6 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
8. The conjugate of claim 1 , wherein the compound is
9. The conjugate of claim 8 , wherein the immunogenic carrier is a protein.
10. The conjugate of claim 9 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
11. The conjugate of claim 1 , wherein the compound is
12. The conjugate of claim 11 , wherein the immunogenic carrier is a protein.
13. The conjugate of claim 12 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
14. The conjugate of claim 1 , wherein the compound is
wherein m is 2 or 3.
15. The conjugate of claim 14 , wherein the immunogenic carrier is a protein.
16. The conjugate of claim 15 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
17. The conjugate of claim 1 , wherein the compound is
18. The conjugate of claim 17 , wherein the immunogenic carrier is a protein.
19. The conjugate of claim 18 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
20. The conjugate of claim 1 , wherein the compound is
21. The conjugate of claim 20 , wherein the immunogenic carrier is a protein.
22. The conjugate of claim 21 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
23. A product made by the process of contacting a compound of Formula I with an immunogenic carrier:
wherein:
R 1 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
NH 2 , or 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 be H simultaneously;
m is 1, 2, 3, 4, or 5; and
n is 1, 2, 3, 4, or 5.
24. The product of claim 23 , wherein:
R 1 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
NH 2 , or 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 or 4; and
n is 1, 2, 3, 4, or 5.
25. The product of claim 23 , wherein:
R 1 is H,
CH 2 NH 2 , or CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
NH 2 , or 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 both R 1 and R 2 may not be H simultaneously;
m is 1, 2, 3, 4, or 5; and
n is 1, 2, 3, 4, or 5.
26. The product of claim 23 , wherein:
R 1 is H,
CH 2 NH 2 , CH 2 NHC(O)(CH 2 ) m CO 2 H;
R 2 is H,
NH 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, or 3; and
n is 1, 2, or 3.
27. The product of claim 23 , wherein the compound is
28. The product of claim 27 , wherein the immunogenic carrier is a protein.
29. The product of claim 28 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
30. The product of claim 23 , wherein the compound is
31. The product of claim 30 , wherein the immunogenic carrier is a protein.
32. The product of claim 31 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
33. The product of claim 23 , wherein the compound is
34. The product of claim 33 , wherein the immunogenic carrier is a protein.
35. The product of claim 34 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
36. The product of claim 23 , wherein the compound is
wherein m is 2 or 3.
37. The product of claim 36 , wherein the immunogenic carrier is a protein.
38. The product of claim 37 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
39. The product of claim 23 , wherein the compound is
40. The product of claim 39 , wherein the immunogenic carrier is a protein.
41. The product of claim 40 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.
42. The product of claim 23 , wherein the compound is
43. The product of claim 42 , wherein the immunogenic carrier is a protein.
44. The product of claim 43 , wherein the protein is keyhole limpet hemocyanin, bovine thyroglobulin, or ovalbumin.