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Last Updated: April 19, 2024

Claims for Patent: 10,323,004


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Summary for Patent: 10,323,004
Title:Inhibitors of indoleamine 2,3-dioxygenase and methods of their use
Abstract: There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the invention.
Inventor(s): Shan; Weifang (Princeton, NJ), Balog; James Aaron (Princeton, NJ)
Assignee: Bristol-Myers Squibb Company (Princeton, NJ)
Application Number:16/098,257
Patent Claims:1. A compound of formula I or formula II: ##STR00022## wherein X is CH or N; T is CH or N; R.sup.1 is H, halo, or C.sub.1-C.sub.6haloalkyl; R.sup.1A is H, halo, or C.sub.1-C.sub.6haloalkyl; Y is CH or N; W is --CH--, --C(C.sub.1-C.sub.6alkyl)-, or N; n is 0, 1, 2, 3, or 4; Z is a bond or C.sub.1-C.sub.6alkylene optionally substituted with one, two, or three substituents independently selected from C.sub.1-C.sub.6alkyl, --OC.sub.1-C.sub.6alkyl, and C.sub.3-C.sub.6cycloalkyl; R.sup.3 is H, --OH, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, halo, --OC.sub.1-C.sub.6alkyl, --OC.sub.1-C.sub.6haloalkyl, --CN, aryl, or --Oaryl; R.sup.3A is H, --OH, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, halo, --OC.sub.1-C.sub.6alkyl, --OC.sub.1-C.sub.6haloalkyl, --CN, aryl, or --Oaryl; or a pharmaceutically acceptable salt thereof, a stereoisomer thereof, a tautomer thereof, or a solvate thereof.

2. The compound of claim 1 that is a compound of formula I.

3. The compound of claim 1 that is a compound of formula II.

4. The compound of claim 1, wherein X is N.

5. The compound of claim 1, wherein X is CH.

6. The compound of claim 1, wherein T is CH.

7. The compound of claim 1, wherein R.sup.1 is H, F, or --CF.sub.3.

8. The compound of claim 1, wherein R.sup.1 is F.

9. The compound of claim 1, wherein R.sup.1A is H.

10. The compound of claim 1, wherein Y is CH and W is CH.

11. The compound of claim 1, wherein Y is N and W is CH.

12. The compound of claim 1, wherein n is 2.

13. The compound of claim 1, wherein R.sup.3 is C.sub.1-C.sub.6alkyl, halo, or --CN.

14. The compound of claim 1, wherein R.sup.3A is H.

15. The compound of claim 1 that is N-benzyl-2-(4-chlorophenyl)-N-(trans-4-(6-fluoroquinolin-4-yl)cyclohexyl)- acetamide; N-benzyl-4-chloro-N-(trans-4-(6-fluoroquinolin-4-yl)cyclohexyl)- benzamide; N-benzyl-4-cyano-N-(trans-4-(6-fluoroquinolin-4-yl)cyclohexyl)b- enzamide; or N-benzyl-2-(4-chlorophenyl)-N-(cis-4-(6-fluoroquinolin-4-yl)cyclohexyl)ac- etamide, or a pharmaceutically acceptable salt thereof, a stereoisomer thereof, a tautomer thereof, or a solvate thereof.

16. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.

17. The pharmaceutical composition of claim 16, further comprising YERVOY, OPDIVO, or KEYTRUDA, or a combination thereof.

18. A method of treating cancer in a patient in need of such treatment comprising administering to the patient a therapeutically effective amount of a compound according to claim 1.

Details for Patent 10,323,004

Applicant Tradename Biologic Ingredient Dosage Form BLA Approval Date Patent No. Expiredate
Bristol-myers Squibb Company YERVOY ipilimumab Injection 125377 03/25/2011 ⤷  Try a Trial 2036-05-04
Merck Sharp & Dohme Corp. KEYTRUDA pembrolizumab For Injection 125514 09/04/2014 ⤷  Try a Trial 2036-05-04
Merck Sharp & Dohme Corp. KEYTRUDA pembrolizumab Injection 125514 01/15/2015 ⤷  Try a Trial 2036-05-04
Bristol-myers Squibb Company OPDIVO nivolumab Injection 125554 12/22/2014 ⤷  Try a Trial 2036-05-04
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Approval Date >Patent No. >Expiredate

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