IP Library › Granted Patent US 9,550,734
Granted Patent B2
US 9,550,734 · App. 14/746,075 · Granted Jan 24, 2017

Bivalent linkers and conjugates thereof

Inventors: Iontcho R. Vlahov (West Lafayette, IN); Christopher P. Leamon (West Lafayette, IN); Apparao Satyam (Mumbai, IN); Stephen J. Howard (Sherman, IL)
Assignee: Endocyte, Inc.
C07D213/71A61K47/48107A61K49/0002C07D401/12C07D475/04
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Quick Facts
Patent No.
US 9,550,734
App. No.
14/746,075
Granted
Jan 24, 2017
Kind
B2
Abstract

Bivalent linkers to be included in or for preparing vitamin, drug, diagnostic agent, and/or imaging agent conjugates are described.

Claims (30)

1. A compound of the formula

wherein

X 1 is heteroarylthio;

Q is selected from the group consisting of

where R a and R b are each independently hydrogen or alkyl; or R a and R b are taken together with the attached carbon atom to form a carbocyclic ring; m and n are each independently an integer from 1 to about 4; and * represents the point of attachment; and

X 2 is aryloxy.

2. The compound of claim 1 , wherein X 1 is optionally substituted 2-pyridinylthio or optionally substituted 4-pyridinylthio.

3. The compound of claim 1 , wherein X 1 is substituted by at least one electron withdrawing substituent selected from the group consisting of cyano, nitro, alkylsulfonyl, arylsulfonyl, halo, haloalkyl, acyl, and carboxyl.

4. The compound of claim 1 , wherein X 1 is substituted by a nitro group.

5. The compound of claim 1 , wherein X 1 is selected from the group consisting of

where * represents the point of attachment.

6. The compound of claim 1 , wherein X 1 is

where * represents the point of attachment.

7. The compound of claim 1 , wherein X 2 is optionally substituted phenyl.

8. The compound of claim 1 , wherein X 2 is substituted by at least one electron withdrawing substituent selected from the group consisting of cyano, nitro, alkylsulfonyl, arylsulfonyl, halo, haloalkyl, acyl, and carboxyl.

9. The compound of claim 1 , wherein X 2 is substituted by a nitro group.

10. The compound of claim 1 , wherein X 2 is selected from the group consisting of

where * represents the point of attachment.

11. The compound of claim 1 , wherein X 2 is

where * represents the point of attachment.

12. The compound of claim 1 , wherein n is 1.

13. The compound of claim 1 , wherein R a and R b are each independently hydrogen or lower alkyl.

14. The compound of claim 1 , wherein R a and R b are each hydrogen.

15. The compound of claim 1 , wherein R a and R b are taken together with the attached carbon atom to form a carbocyclic ring.

16. The compound of claim 1 , wherein R a and R b are taken together with the attached carbon atom to form cyclopropyl.

17. The compound of claim 1 , wherein Q is

where R a and R b are each independently hydrogen or alkyl; or R a and R b are taken together with the attached carbon atom to form a carbocyclic ring; n is an integer from 1 to about 4; and * represents the point of attachment.

18. The compound of claim 1 , wherein Q is

where m is an integer from 1 to about 4 and * represents the point of attachment.

19. The compound of claim 1 , wherein the compound is of the formula

Continuity (4)
Continuation 13609995 · Sep 11, 2012
Continuation 11632895
Provisional Application 60590580 · Jul 23, 2004
Related Publication 20160002167A1 · Jan 7, 2016