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Last Updated: October 16, 2019

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Claims for Patent: 8,344,153

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Summary for Patent: 8,344,153
Title:Inhibitors of phosphatidylinositol 3-kinase
Abstract: The present invention relates to compounds useful as inhibitors of PI3K, particularly of PI3K.gamma.. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various disease, conditions, or disorders.
Inventor(s): Cottrell; Kevin Michael (Cambridge, MA), Aronov; Alex (Newton, MA), Davies; Robert J. (Watertown, MA), Come; Jon H. (Cambridge, MA), Messersmith; David (Somerville, MA), Xu; Jinwang (Framingham, MA), Bandarage; Upul Keerthi (Lexington, MA), Cao; Jingrong (Newton, MA)
Assignee: Vertex Pharmaceuticals Incorporated (Cambridge, MA)
Application Number:12/796,825
Patent Claims:1. A compound having the formula: ##STR00181## or a pharmaceutically acceptable salt thereof, wherein: Ar is a phenyl ring or a 5-10 membered monocyclic or fused bicyclic heteroaryl ring having up to 2 atoms selected from nitrogen, wherein each ring is optionally substituted with up to 3 substituents independently selected from fluoro, chloro, C.sub.1-4aliphatic, C.sub.3-4cycloaliphatic, --OC.sub.1-4aliphatic, --OC.sub.3-4cycloaliphatic, --N(J.sup.R1)C(O)C.sub.1-4aliphatic, or N(J.sup.R1).sub.2, wherein each of said aliphatic or cycloaliphatic is optionally substituted with up to 3 occurrences of fluoro; R.sup.1 is selected from --C(O)R.sup.1a, --C(O)OR.sup.1a, or --C(O)N(R.sup.1a)(R.sup.1b) wherein R.sup.1a is C.sub.1-4 aliphatic, C.sub.3-6 cycloaliphatic, or C.sub.5-10 heterocyclic having up to 2 atoms selected from oxygen, sulfur, or nitrogen, wherein R.sup.1a is optionally substituted with 1, 2, 3, or 4, occurrences of J.sup.R; each J.sup.R is independently fluoro, oxo, --C(O)J.sup.R1, --C(O)N(J.sup.R1).sub.2, --C(O)O(J.sup.R1), --N(J.sup.R1)C(O)J.sup.R1, --OJ.sup.R1, --SJ.sup.R1, --S(O)J.sup.R1, phenyl or a 5-10 membered heteroaryl or heterocyclyl ring having up to 2 atoms selected from nitrogen, oxygen, or sulfur, wherein said phenyl, heteroaryl, or heterocyclyl is optionally substituted with 1 or 2 J.sup.R2 groups; R.sup.1b is, independently, hydrogen, C.sub.1-4aliphatic, C.sub.3-6cycloaliphatic; or R.sup.1a and R.sup.1b, together with the nitrogen to which they are attached, form a 4-6 membered heterocyclic ring, wherein said heterocyclic ring optionally comprises one additional heteroatom selected from nitrogen and oxygen, and wherein said heterocyclic ring is optionally substituted with 1 or 2 J.sup.R2 groups; R.sup.2 is C.sub.1-4aliphatic optionally substituted with 1, 2, or 3 J.sup.R2 groups; each J.sup.R1 is independently selected from hydrogen, C.sub.1-4aliphatic, C.sub.3-6cycloaliphatic, phenyl, benzyl, or 5-6 membered heteroaryl ring having up to two atom selected from nitrogen, oxygen, or sulfur, wherein each of said C.sub.1-4aliphatic, phenyl, benzyl, or heteroaryl is optionally substituted with up to three J.sup.R2 groups; and each J.sup.R2 is, independently, selected from chloro, fluoro, --CN, --NO.sub.2, oxo, C.sub.1-4alkyl, C.sub.3-6cycloalkyl, --OH, --OC.sub.1-4alkyl, --OPhenyl, or --OCH.sub.2Phenyl, wherein each of said alkyl, cycloalkyl or phenyl is optionally substituted with up to 3 fluoro groups.

2. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein Ar is an optionally substituted 5-10 membered heteroaryl ring.

3. The compound according to claim 2, or a pharmaceutically acceptable salt thereof, wherein Ar is an optionally substituted group selected from: ##STR00182##

4. The compound according to claim 3, wherein Ar is substituted with 1 to 2 groups independently selected from --OCH.sub.3, --OCF.sub.3, --OCHF.sub.2, Cl, F, or CF.sub.3.

5. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R.sup.2 is CH.sub.3.

6. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R.sup.1 is --C(O)N(R.sup.1a)(R.sup.1b).

7. The compound according to claim 6, or a pharmaceutically acceptable salt thereof, wherein R.sup.1b is hydrogen.

8. The compound according to claim 7, or a pharmaceutically acceptable salt thereof, wherein R.sup.1a is --CH.sub.2CH(R)-J.sup.R, wherein R is hydrogen or methyl and J.sup.R is --OJ.sup.R1 or a 5-membered heteroaryl having 2 nitrogen atoms and substituted with C.sub.1-3alkyl or cyclopropyl, each optionally substituted with up to 3 fluoro groups.

9. The compound according to claim 8, or a pharmaceutically acceptable salt thereof, wherein J.sup.R is ##STR00183##

10. The compound according to claim 8, or a pharmaceutically acceptable salt thereof, wherein J.sup.R is --OJ.sup.R1 and J.sup.R1 is C.sub.1-4alkyl, optionally substituted with cyclopropyl or up to three fluoro or methyl groups.

11. The compound according to claim 10, or a pharmaceutically acceptable salt thereof, wherein J.sup.R1 is --CH.sub.2-cyclopropyl.

12. The compound according to claim 8, or a pharmaceutically acceptable salt thereof, wherein J.sup.R is --OJ.sup.R1 and J.sup.R1 is phenyl or pyridyl, optionally substituted with up to three fluoro groups.

13. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein said compound is selected from ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211##

14. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier, adjuvant, or vehicle.

15. The composition according to claim 14, additionally comprising a therapeutic agent selected from an agent for treating multiple sclerosis, an anti-inflammatory agent, an immunomodulatory agent, or an immunosuppressive agent.

16. The composition according to claim 15, wherein said therapeutic agent is beta interferon, glatiramir, natalizumab, or mitoxantrone.

Details for Patent 8,344,153

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Biogen Idec TYSABRI natalizumab VIAL; SINGLE-USE 125104 001 2004-11-23   Request a Trial Vertex Pharmaceuticals Incorporated (Cambridge, MA) 2029-06-10 RX search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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