http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-101528-A1

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publicationDate 2016-12-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber AR-101528-A1
titleOfInvention CDK9 QUINASE INHIBITORS OF PIRROLO [2,3-B] PIRIDINA
abstract The compounds can be used as agents in the treatment of diseases, including cancer. Pharmaceutical compositions comprising one or more compounds of formula (1) are also provided. Claim 1: A compound of formula (1), or a pharmaceutically acceptable salt thereof, wherein R¹ is selected from the group consisting of cycloalkyl, cycloalkenyl, heterocycloalkyl, and heterocycloalkenyl; wherein R¹ cycloalkyl, cycloalkenyl, heterocycloalkyl and heterocycloalkenyl are optionally substituted with one or more substituents independently selected from the group consisting of R⁵, OR⁵, SR⁵, S (O) R⁵, SO₂R⁵, C (O) R⁵, CO ( O) R⁵, OC (O) R⁵, OC (O) OR⁵, NH₂, NHR⁵, N (R⁵) ₂, NHC (O) R⁵, NR⁵C (O) R⁵, SO₂NHC (O) R⁵, SO₂NR⁵C (O) R⁵, NHS (O) ₂R⁵, NR⁵S (O) ₂R⁵, NHC (O) OR⁵, NR⁵C (O) OR⁵, SO₂NHC (O) OR⁵, SO₂NR⁵C (O) OR⁵, NHSO₂NHC (O) OR⁵, NHSO₂NR⁵C (O) OR⁵, NR⁵SO₂NR⁵C ( O) OR⁵, NR⁵SO₂NHC (O) OR⁵, NHC (O) NH₂, NHC (O) NHR⁵, NHC (O) N (R⁵) ₂, NR⁵C (O) NHR⁵, NR⁵C (O) N (R⁵) ₂, OC ( O) NH₂, OC (O) NHR⁵, OC (O) N (R⁵) ₂, OC (O) NHSO₂R⁵, OC (O) NR⁵SO₂R⁵, C (O) NH₂, C (O) NHR⁵, C (O) N ( R⁵) ₂, C (O) NHOH, C (O) NHOR⁵, C (O) NHSO₂R⁵, C (O) NR⁵SO₂R⁵, SO₂NH₂, SO₂NHR⁵, SO₂N (R⁵) ₂, OSO₂NH₂, OSO₂NHR⁵, OSO₂N (R⁵) ₂, C ( O) NHCN, C (O) NR⁵CN, S (O) (N) R⁵, C (O) H, C (O) OH, (O), OH, CN, NO ₂, F, Cl, Br and I; R² is selected from the group consisting of hydrogen, C₁₋₄ alkyl, NO₂, CN, C (O) NH₂, and C (O) OR²A; R²A is selected from the group consisting of alkyl, alkenyl, and alkynyl; R³ is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, and pyridazinyl; wherein R³ phenyl, pyridinyl, pyrazinyl, pyrimidinyl, and pyridazinyl are optionally substituted with one or more substituents independently selected from the group consisting of R⁶, OR⁶, SR⁶, S (O) R⁶, C (O) R⁶, CO (O) R⁶, OC (O) R⁶, OC (O) OR⁶, NH₂, NHR⁶, N (R⁶) ₂, NHC (O) R⁶, NR⁶C (O) R⁶, NHS (O) ₂R⁶, NR⁶S (O) ₂R⁶ , NHC (O) OR⁶, NR⁶C (O) OR⁶, NHC (O) NH₂, NHC (O) NHR⁶, NHC (O) N (R⁶) ₂, NR⁶C (O) NHR⁶, NR⁶C (O) N (R⁶) ₂ , C (O) NH₂, C (O) NHR⁶, C (O) N (R⁶) ₂, C (O) NHOH, C (O) NHOR⁶, C (O) NHSO₂R⁶, C (O) NR⁶SO₂R⁶, C (O ) H, C (O) OH, (O), OH, CN, NO₂, F, Cl, Br and I; R⁴ is selected from the group consisting of hydrogen, R⁴A, OR⁴A, C (O) NH₂, CN, F, Cl, Br, and I; R⁴A is selected from the group consisting of haloalkyl, alkyl, alkenyl, and alkynyl; R⁵, in each case, is independently selected from the group consisting of C₁₋₈ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, aryl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, cycloalkyl, and cycloalkenyl; where each R⁵ C₁₋₈ alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of R⁷, OR⁷, SR⁷, S (O) R⁷, SO₂R⁷, C (O) R⁷, CO (O) R⁷, OC (O) R⁷, OC (O) OR⁷, NH₂, NHR⁷, N (R⁷) ₂, NHC (O) R⁷, NR⁷C (O) R⁷, NHS (O) ₂R⁷, NR⁷S (O) ₂R⁷, NHC (O) OR⁷, NR⁷C (O) OR⁷, NHC (O) NH₂, NHC (O) NHR⁷, NHC (O) N (R⁷) ₂, NR⁷C (O) NHR⁷, NR⁷C ( O) N (R⁷) ₂, C (O) NH₂, C (O) NHR⁷, C (O) N (R⁷) ₂, C (O) NHOH, C (O) NHOR⁷, C (O) NHSO₂R⁷, C ( O) NR⁷SO₂R⁷, SO₂NH₂, SO₂NHR⁷, SO₂N (R⁷) ₂, C (O) H, C (O) OH, OH, CN, NO₂, F, Cl, Br and I; wherein each R⁵ aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocycloalkyl, and heterocycloalkenyl is optionally substituted with one or more substituents independently selected from the group consisting of R⁸, OR⁸, SR⁸, S (O) R⁸, SO₂R⁸, C (O ) R⁸, CO (O) R⁸, OC (O) R⁸, OC (O) OR⁸, NH₂, NHR⁸, N (R⁸) ₂, NHC (O) R⁸, NR⁸C (O) R⁸, NHS (O) ₂R⁸, NR⁸S (O) ₂R⁸, NHC (O) OR⁸, NR⁸C (O) OR⁸, NHC (O) NH₂, NHC (O) NHR⁸, NHC (O) N (R⁸) ₂, NR⁸C (O) NHR⁸, NR⁸C (O) N (R⁸) ₂, C (O) NH₂, C (O) NHR⁸, C (O) N (R⁸) ₂, C (O) NHOH, C (O) NHOR⁸, C (O) NHSO₂R⁸, C (O) NR⁸SO₂R⁸ , SO₂NH₂, SO₂NHR⁸, SO₂N (R⁸) ₂, C (O) H, C (O) OH, (O), OH, CN, NO₂, F, Cl, Br and I; R⁶, in each case, is independently selected from the group consisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, aryl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, cycloalkyl, and cycloalkenyl; where each R⁶ C₁₋₆ alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of R⁹, OR⁹, SR⁹, S (O) R⁹, SO₂R⁹, C (O) R⁹, CO (O) R⁹, OC (O) R⁹, OC (O) OR⁹, NH₂, NHR⁹, N (R⁹) ₂, NHC (O) R⁹, NR⁹C (O) R⁹, NHS (O) ₂R⁹, NR⁹S (O) ₂R⁹, NHC (O) OR⁹, NR⁹C (O) OR⁹, NHC (O) NH₂, NHC (O) NHR⁹, NHC (O) N (R⁹) ₂, NR⁹C (O) NHR⁹, NR⁹C ( O) N (R⁹) ₂, C (O) NH₂, C (O) NHR⁹, C (O) N (R⁹) ₂, C (O) NHOH, C (O) NHOR⁹, C (O) NHSO₂R⁹, C ( O) NR⁹SO₂R⁹, SO₂NH₂, SO₂NHR⁹, SO₂N (R⁹) ₂, C (O) H, C (O) OH, OH, CN, NO₂, F, Cl, Br and I; wherein each R⁶ aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocycloalkyl, and heterocycloalkenyl is optionally substituted with one or more substituents independently selected from the group consisting of R¹⁰, OR¹⁰, SR¹⁰, S (O) R¹⁰, SO₂R¹⁰, C (O ) R¹⁰, CO (O) R¹⁰, OC (O) R¹⁰, OC (O) OR¹⁰, NH₂, NHR¹⁰, N (R¹⁰) ₂, NHC (O) R¹⁰, NR¹⁰C (O) R¹⁰, NHS (O) ₂R¹⁰, NR¹⁰S (O) ₂R¹⁰, NHC (O) OR¹⁰, NR¹⁰C (O) OR¹⁰, NHC (O) NH₂, NHC (O) NHR¹⁰, NHC (O) N (R¹⁰) ₂, NR¹⁰C (O) NHR¹⁰, NR¹⁰C (O) N (R¹⁰) ₂, C (O) NH₂, C (O) NHR¹⁰, C (O) N (R¹⁰) ₂, C (O) NHOH, C (O) NHOR¹⁰, C (O) NHSO₂R¹⁰, C (O) NR¹⁰SO₂R¹⁰ , SO₂NH₂, SO₂NHR¹⁰, SO₂N (R¹⁰) ₂, C (O) H, C (O) OH, (O), OH, CN, NO₂, F, Cl, Br and I; R⁷, in each case, is independently selected from the group consisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, aryl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, cycloalkyl, and cycloalkenyl; wherein each R⁷ C₁₋₆ alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of aryl, heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkyl, heterocycloalkenyl, NH₂, NHR¹³, N (R¹³) ₂, C (O) H, C (O) OH, OH, CN, NO₂, F, Cl, Br and I; wherein each R⁷ aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocycloalkyl, and heterocycloalkenyl is optionally substituted with one or more substituents independently selected from the group consisting of R¹¹, OR¹¹, SR¹¹, S (O) R¹¹, SO₂R¹¹, C (O ) R¹¹, CO (O) R¹¹, OC (O) R¹¹, OC (O) OR¹¹, NH₂, NHR¹¹, N (R¹¹) ₂, NHC (O) R¹¹, NR¹¹C (O) R¹¹, NHS (O) ₂R¹¹, NR¹¹S (O) ₂R¹¹, NHC (O) OR¹¹, NR¹¹C (O) OR¹¹, NHC (O) NH₂, NHC (O) NHR¹¹, NHC (O) N (R¹¹) ₂, NR¹¹C (O) NHR¹¹, NR¹¹C (O) N (R¹¹) ₂, C (O) NH₂, C (O) NHR¹¹, C (O) N (R¹¹) ₂, C (O) NHOH, C (O) NHOR¹¹, C (O) NHSO₂R¹¹, C (O) NR¹¹SO₂R¹¹ , SO₂NH₂, SO₂NHR¹¹ SO₂N (R¹¹) ₂, C (O) H, C (O) OH, (O), OH, CN, NO₂, F, Cl, Br and I; R⁸, in each case, is independently selected from the group consisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, and C₂₋₆, alkynyl; where each R⁸ C₁₋₆ alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of NH₂, C (O) H, C (O) OH, OH, CN, NO₂, F, Cl, Br and I; R⁹, in each case, is independently selected from the group consisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, aryl, heteroaryl, heterocycloalkyl, heterocycloalkenyl, cycloalkyl, and cycloalkenyl; where each R⁹ aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocycloalkyl, and heterocycloalkenyl is optionally substituted with one or more substituents independently selected from the group consisting of R¹², OR¹², SR¹², S (O) R¹², SO₂R¹², C (O ) R¹², CO (O) R¹², OC (O) R¹², OC (O) OR¹², NH₂, NHR¹², N (R¹²) ₂, NHC (O) R¹², NR¹²C (O) R¹², NHS (O) ₂R¹², NR¹²S (O) ₂R¹², NHC (O) OR¹², NR¹²C (O) OR¹², NHC (O) NH₂, NHC (O) NHR¹², NHC (O) N (R¹²) ₂, NR¹²C (O) NHR¹², NR¹²C (O) N (R¹²) ₂, C (O) NH₂, C (O) NHR¹², C (O) N (R¹²) ₂, C (O) NHOH, C (O) NHOR¹², C (O) NHSO₂R¹², C (O) NR¹²SO₂R¹² , SO₂NH₂, SO₂NHR¹², SO₂N (R¹²) ₂, C (O) H, C (O) OH, (O), OH, CN, NO₂, F, Cl, Br and I; R¹⁰, in each case, is independently selected from the group consisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl; where each R¹⁰ C₁₋₆ alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of NH₂, C (O) H, C (O) OH, OH, CN, NO₂, F, Cl, Br and I; R¹¹, in each case, is independently selected from the group consisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl; where each R¹¹ C₁₋₆ alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of NH₂, C (O) H, C (O) OH, OH, CN, NO₂, F, Cl, Br and I; R¹², in each case, is independently selected from the group consisting of C₁₋₆, alkyl, C₂₋₆, alkenyl, and C₂₋₆ alkynyl; where each R¹² C₁₋₆, alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl is optionally substituted with one or more, substituents independently selected from the group consisting of NH₂, NHR¹³, N (R¹³) ₂, C ( O) H, C (O) OH, OH, CN, NO₂, F, Cl, Br and I; and R¹³, in each case, is independently selected from the group consisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, and C₂₋₆ alkynyl.
priorityDate 2013-03-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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Total number of triples: 48.