You’re using a public version of DrugPatentWatch with 5 free searches available | Register to unlock more free searches. CREATE FREE ACCOUNT

Last Updated: March 29, 2024

Details for Patent: 9,162,989


✉ Email this page to a colleague

« Back to Dashboard


Title:2,4-Pyrimidinediamine compounds and their uses
Abstract: The present invention provides 2,4-pyrimidinediamine compounds that inhibit the IgE and/or IgG receptor signaling cascades that lead to the release of chemical mediators, intermediates and methods of synthesizing the compounds and methods of using the compounds in a variety of contexts, including in the treatment and prevention of diseases characterized by, caused by or associated with the release of chemical mediators via degranulation and other processes effected by activation of the IgE and/or IgG receptor signaling cascades.
Inventor(s): Singh; Rajinder (Belmont, CA), Argade; Ankush (Foster City, CT), Payan; Donald G. (Hillsborough, CA), Molineaux; Susan (San Mateo, CA), Holland; Sacha J. (San Francisco, CA), Clough; Jeffrey (Redwood City, CA), Keim; Holger (Irvine, CA), Bhamidipati; Somasekhar (Foster City, CA), Sylvain; Catherine (San Mateo, CA), Li; Hui (Santa Clara, CA), Rossi; Alexander B. (Reedsport, OR)
Assignee: Rigel Pharmaceuticals, Inc. (South San Francisco, CA)
Filing Date:Feb 19, 2015
Application Number:14/626,471
Claims:1. A compound according to Formula (I): ##STR00048## or a salt thereof, wherein: R.sup.2 and R.sup.4 are different and independently are each phenyl substituted with one or more of the same or different R.sup.8 groups; R.sup.5 is fluoro; R.sup.8 is selected from R.sup.a, R.sup.b, R.sup.a substituted with one or more of the same or different R.sup.a or R.sup.b, OR.sup.a substituted with one or more of the same or different R.sup.a, --(CH.sub.2).sub.m--R.sup.b, --(CHR.sup.a).sub.m--R.sup.b, --O--(CH.sub.2).sub.m--R.sup.b, --O--(CHR.sup.a).sub.m--R.sup.b, --C(O)NH--(CH.sub.2).sub.m--R.sup.b, --C(O)NH--(CHR.sup.a).sub.m--R.sup.b, --O--(CH.sub.2).sub.m--C(O)NH--(CH.sub.2).sub.m--R.sup.b, --O--(CHR.sup.a).sub.m--C(O)NH--(CHR.sup.a).sub.m--R.sup.b, --NH--(CH.sub.2).sub.m--R.sup.b or --NH--(CHR.sup.a).sub.m--R.sup.b; each R.sup.a is independently selected from hydrogen, (C1-C6)alkyl, (C3-C8)cycloalkyl, cyclohexyl, (C4-C11)cycloalkylalkyl, (C5-C10)aryl, phenyl, (C6-C16) arylalkyl, benzyl, 3-8 membered cycloheteroalkyl, morpholinyl, piperazinyl, homopiperazinyl, piperidinyl, 4-11 membered cycloheteroalkylalkyl, 5-10 membered heteroaryl, or 6-16 membered heteroarylalkyl; each R.sup.b is independently selected from .dbd.O, OR.sup.a, (C1-C3) haloalkyloxy, .dbd.S, .dbd.SR.sup.a, .dbd.NR.sup.a, .dbd.NONR.sup.a, --NR.sup.cR.sup.c, halogen, --CF.sub.3, --CN, --OCN, --SCN, --NO, NO.sub.2, .dbd.N.sub.2, --N.sub.3, --S(O)R.sup.a, --S(O).sub.2R.sup.a, --S(O).sub.2OR.sup.a, --S(O).sub.2NR.sup.cR.sup.c, --OS(O)R.sup.a, --OS(O).sub.2R.sup.a, --OS(O).sub.2OR.sup.a, --OS(O).sub.2NR.sup.cR.sup.c, --C(O)R.sup.a, --C(O)OR.sup.a, --C(O)NR.sup.cR.sup.c, --C(NH)NR.sup.cR.sup.c, OC(O)R.sup.a, --OC(O)OR.sup.a, --OC(O)NR.sup.cR.sup.c, --OC(NH)NR.sup.cR.sup.c, [NHC(O)]R.sup.a, --[NHC(O)]OR.sup.a, [NHC(O)]NR.sup.cR.sup.c or --[NHC(NH)]NR.sup.cR.sup.c; each R.sup.c is independently R.sup.a, or, alternatively, each R.sup.c is taken together with the nitrogen atom to which it is bonded to form a 5 to 8-membered cycloheteroalkyl or heteroaryl which may optionally include one or more of the same or different additional heteroatoms and which is optionally substituted with one or more of the same or different R.sup.a or suitable R.sup.b groups; at least one R.sup.8 is R.sup.b; and each m is independently an integer from 1 to 3.

2. The compound of claim 1, wherein R.sup.2 is monosubstituted with an R.sup.8 group.

3. The compound of claim 2, wherein the R.sup.8 group is at the para position of R.sup.2.

4. The compound of claim 2, wherein the R.sup.8 group on R.sup.2 is selected from (C1-C6) alkyl, (C1-C6) branched alkyl, --O--C(O)OR.sup.a, --O--(CH.sub.2).sub.m--C(O)OR.sup.a, --C(O)OR.sup.a, --O--(CH.sub.2).sub.m--NR.sup.cR.sup.c, --O--C(O)NR.sup.cR.sup.c, --O--(CH.sub.2).sub.m--C(O)NR.sup.cR.sup.c, --O--C(NH)NR.sup.cR.sup.c, --O--(CH.sub.2).sub.m--C(NH)NR.sup.cR.sup.c, or --NH--(CH.sub.2).sub.m--NR.sup.cR.sup.c.

5. The compound of claim 4, wherein the R.sup.8 group on R.sup.2 is O--(CH.sub.2).sub.m--R.sup.b.

6. The compound of claim 1, wherein R.sup.4 is substituted with at least one R.sup.b group.

7. The compound of claim 6, wherein the at least one R.sup.b group is selected from --OC(O)R.sup.a, --OC(O)OR.sup.a, --OC(O)NR.sup.cR.sup.c, --OC(NH)NR.sup.cR.sup.c, --[NHC(O)]R.sup.a, --[NHC(O)]NR.sup.cR.sup.c, or --[NHC(NH)].sub.nNR.sup.cR.sup.c.

8. The compound of claim 1, wherein the R.sup.4 phenyl is monosubstituted.

9. The compound of claim 8, wherein the R.sup.4 phenyl is monosubstituted with an R.sup.b group at the meta or para position.

Make Better Decisions: Try a trial or see plans & pricing

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.