Haptens of quetiapine

Patent metadata

Field	Value
Publication number	US-9304126-B2
Application number	US-201313970667-A
Country	US
Kind code	B2
Filing date	Aug 20, 2013
Priority date	Aug 21, 2012
Publication date	Apr 5, 2016
Grant date	Apr 5, 2016

Abstract

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 quetiapine. The invention also relates to conjugates of a quetiapine hapten and a protein.

First claim

We claim:

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 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.

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,

or CH 2 NH 2 ;
R 2 is H,

or CH 2 NH 2 ; 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 compound of claim 1 , selected from the group consisting of:

7. A conjugate of a compound of claim 1 and a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

8. A conjugate of the compound of claim 2 and a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

9. A conjugate of the compound of claim 3 and a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

10. A conjugate of the compound of claim 4 and a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

11. A conjugate of the compound of claim 5 and a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

12. The conjugate of claim 7 wherein the compound is

13. A product made by the process of contacting a compound of claim 1 with a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

14. A product made by the process of contacting a compound of claim 2 with a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

15. A product made by the process of contacting a compound of claim 3 with a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

16. A product made by the process of contacting a compound of claim 4 with a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

17. A product made by the process of contacting a compound of claim 5 with a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

18. A product made by the process of contacting a compound which is

with a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

19. 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;
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.

20. A conjugate of a compound of claim 19 and a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

21. A product made by the process of contacting a compound of claim 19 with a protein, wherein said protein is selected from keyhole limpet hemocyanin, ovalbumin or bovine thyroglobulin.

Assignees

• Janssen Pharmaceutica Nv
• Ortho Clinical Diagnostics Inc

Inventors

• Donahue Matthew Garrett
• Gong Yong
• Salter Rhys
• Hryhorenko Eric
• Decory Thomas R
• Remmerie Bart
• Sankaran Banumathi

Classifications

• A61P25/00

  Drugs for disorders of the nervous system · CPC title

• C07D417/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D281/16

  [b, f]-condensed · CPC title

• G01N33/5308 Primary

  for analytes not provided for elsewhere, e.g. nucleic acids, uric acid, worms, mites · CPC title

• C07K14/795

  Porphyrin- or corrin-ring-containing peptides · CPC title