TWI510487B - 用於激酶調節的化合物和方法及其適應症 - Google Patents
用於激酶調節的化合物和方法及其適應症 Download PDFInfo
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- TWI510487B TWI510487B TW100113512A TW100113512A TWI510487B TW I510487 B TWI510487 B TW I510487B TW 100113512 A TW100113512 A TW 100113512A TW 100113512 A TW100113512 A TW 100113512A TW I510487 B TWI510487 B TW I510487B
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- Prior art keywords
- fluoro
- pyridyl
- pyrrolo
- amino
- pyrimidin
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- ZSRQKNXWSKESRS-UHFFFAOYSA-N [4-(cyclopropylmethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC3CC3)=C12 ZSRQKNXWSKESRS-UHFFFAOYSA-N 0.000 claims 1
- RECGXXWAANSOAE-UHFFFAOYSA-N [4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 RECGXXWAANSOAE-UHFFFAOYSA-N 0.000 claims 1
- JYYOWPLYDVTMEM-UHFFFAOYSA-N [4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(CC)N=C1 JYYOWPLYDVTMEM-UHFFFAOYSA-N 0.000 claims 1
- QKRHXRNNIDKEBP-UHFFFAOYSA-N [4-[(1-ethylpiperidin-4-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1CN(CC)CCC1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC=3C=NC(OC)=CC=3)=CC=1)F)=CN2 QKRHXRNNIDKEBP-UHFFFAOYSA-N 0.000 claims 1
- NICCYTIXGQSYBK-UHFFFAOYSA-N [4-[(4,4-difluorocyclohexyl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCC(F)(F)CC3)=C12 NICCYTIXGQSYBK-UHFFFAOYSA-N 0.000 claims 1
- HTNOMZMPUYZIGE-LRVUVFPRSA-N [4-[[(1r)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound N([C@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 HTNOMZMPUYZIGE-LRVUVFPRSA-N 0.000 claims 1
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- LICZZOHNIURVBP-GFCCVEGCSA-N [4-[[(1r)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]methanone Chemical compound N([C@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C=C1F)=CN=C1NC1CCC(F)(F)CC1 LICZZOHNIURVBP-GFCCVEGCSA-N 0.000 claims 1
- GQGXOAFWKBFUPX-LBPRGKRZSA-N [4-[[(2s)-butan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(N[C@@H](C)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 GQGXOAFWKBFUPX-LBPRGKRZSA-N 0.000 claims 1
- HBRLFMUTJKOUOY-ZDUSSCGKSA-N [4-[[(2s)-butan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(N[C@@H](C)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 HBRLFMUTJKOUOY-ZDUSSCGKSA-N 0.000 claims 1
- MLZJHYYTGXCFDI-UHFFFAOYSA-N [6-(cyclohexylamino)-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCCCC1 MLZJHYYTGXCFDI-UHFFFAOYSA-N 0.000 claims 1
- IUWDOUDLGKJYOM-UHFFFAOYSA-N [6-(cyclohexylamino)-2-fluoropyridin-3-yl]-[4-(propan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(C)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCCCC1 IUWDOUDLGKJYOM-UHFFFAOYSA-N 0.000 claims 1
- KMUJEQBTZNFUTI-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC1CC(F)(F)C1 KMUJEQBTZNFUTI-UHFFFAOYSA-N 0.000 claims 1
- OKZIXHATEKJFCV-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 OKZIXHATEKJFCV-UHFFFAOYSA-N 0.000 claims 1
- FBQYBWMASKYPQH-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 FBQYBWMASKYPQH-UHFFFAOYSA-N 0.000 claims 1
- AIWOCBWNWVBKCK-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 AIWOCBWNWVBKCK-UHFFFAOYSA-N 0.000 claims 1
- AYVPLGIMBXBDSH-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(propylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 AYVPLGIMBXBDSH-UHFFFAOYSA-N 0.000 claims 1
- UFJCQWQNZVJFEU-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 UFJCQWQNZVJFEU-UHFFFAOYSA-N 0.000 claims 1
- LLQDTYOHPTWZIA-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 LLQDTYOHPTWZIA-UHFFFAOYSA-N 0.000 claims 1
- CDARGWIZUNGPBX-HZPDHXFCSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(1r,2r)-2-hydroxycyclopentyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound O[C@@H]1CCC[C@H]1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC3CCC(F)(F)CC3)=CC=1)F)=CN2 CDARGWIZUNGPBX-HZPDHXFCSA-N 0.000 claims 1
- UURRFCIRZCTHIV-SNVBAGLBSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1,1,1-trifluoropropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@H](C)C(F)(F)F)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 UURRFCIRZCTHIV-SNVBAGLBSA-N 0.000 claims 1
- LRNOPCNTRVGVIB-LLVKDONJSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-hydroxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@@H](CO)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 LRNOPCNTRVGVIB-LLVKDONJSA-N 0.000 claims 1
- UOHFJNMMFPVFEW-GFCCVEGCSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-methoxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@H](C)COC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 UOHFJNMMFPVFEW-GFCCVEGCSA-N 0.000 claims 1
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- ICSCRMQMPQFSAP-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C=N1)=CC=C1NC1CCC(F)(F)CC1 ICSCRMQMPQFSAP-UHFFFAOYSA-N 0.000 claims 1
- ABHMVYRSYBXULP-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-(4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methanone Chemical compound C=1C=C(C(=O)C=2C3=C(C4CC4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 ABHMVYRSYBXULP-UHFFFAOYSA-N 0.000 claims 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 33
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- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 3
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- SUTAZURMHGAKLC-UHFFFAOYSA-N 3-iodo-5-methyl-1h-pyrrolo[2,3-b]pyridine Chemical compound CC1=CN=C2NC=C(I)C2=C1 SUTAZURMHGAKLC-UHFFFAOYSA-N 0.000 description 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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| SG183036A1 (en) | 2007-07-17 | 2012-08-30 | Plexxikon Inc | Compounds and methods for kinase modulation, and indications therefor |
| WO2009143018A2 (en) | 2008-05-19 | 2009-11-26 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| US8450322B2 (en) | 2008-09-22 | 2013-05-28 | Array Biopharma Inc. | Substituted imidazo[1,2b]pyridazine compounds as Trk kinase inhibitors |
| TR201807039T4 (tr) | 2008-10-22 | 2018-06-21 | Array Biopharma Inc | Trk kinaz inhibitörleri olarak sübstitüe edilmiş pirazolo[1,5-]pirimidin bileşikleri. |
| AU2010232670B2 (en) | 2009-04-03 | 2015-07-09 | F. Hoffmann-La Roche Ag | Propane- I-sulfonic acid {3- [5- (4 -chloro-phenyl) -1H-pyrrolo [2, 3-b] pyridine-3-carbonyl] -2, 4-difluoro-pheny l } -amide compositions and uses thereof |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| MX2012005284A (es) | 2009-11-06 | 2012-06-28 | Plexxikon Inc | Compuestos y metodos para la modulacion de cinasas. e indicaciones para ello. |
| CN102740698A (zh) | 2009-11-18 | 2012-10-17 | 普莱希科公司 | 用于激酶调节的化合物和方法及其适应症 |
| BR112012015745A2 (pt) | 2009-12-23 | 2016-05-17 | Plexxikon Inc | compostos e métodos para a modulação de quinase, e indicações dos mesmos |
| TWI619713B (zh) | 2010-04-21 | 2018-04-01 | 普雷辛肯公司 | 用於激酶調節的化合物和方法及其適應症 |
| ES2628418T3 (es) | 2010-05-20 | 2017-08-02 | Array Biopharma, Inc. | Compuestos macrocíclicos como inhibidores de la TRK cinasa |
| KR101911972B1 (ko) | 2011-02-07 | 2018-10-25 | 플렉시콘 인코퍼레이티드 | 키나제 조절을 위한 화합물 및 방법, 및 그에 대한 적응증 |
| AP2013007159A0 (en) | 2011-04-05 | 2013-10-31 | Pfizer Ltd | Pyrrolo [2,3-D] pyrimidine derivatives as inhibitors of tropomyosin-related kinase |
| SG194847A1 (en) | 2011-05-17 | 2013-12-30 | Plexxikon Inc | Kinase modulation and indications therefor |
| US9358235B2 (en) | 2012-03-19 | 2016-06-07 | Plexxikon Inc. | Kinase modulation, and indications therefor |
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| WO2014018888A1 (en) | 2012-07-26 | 2014-01-30 | Confluence Life Sciences Inc. | 4-alkoxy/aralkoxy-5-substituted-pyrrolopyrimidine compounds as tak1 inhibitors in disease treatment |
| WO2014039714A2 (en) | 2012-09-06 | 2014-03-13 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2014053968A1 (en) | 2012-10-04 | 2014-04-10 | Pfizer Limited | Pyrrolo[3,2-c]pyridine tropomyosin-related kinase inhibitors |
| JP2015531393A (ja) | 2012-10-04 | 2015-11-02 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | トロポミオシン関連キナーゼ阻害剤 |
| CA2885253A1 (en) | 2012-10-04 | 2014-04-10 | Pfizer Limited | Pyrrolo[2,3-d]pyrimidine tropomyosin-related kinase inhibitors |
| CA2895239C (en) | 2012-12-21 | 2020-10-27 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
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| WO2014145051A1 (en) | 2013-03-15 | 2014-09-18 | Jiazhong Zhang | Heterocyclic compounds and uses thereof |
| BR112015028845A2 (pt) | 2013-05-30 | 2017-07-25 | Plexxikon Inc | compostos para a modulação da quinase e indicações da mesma |
| EP3628749A1 (en) | 2013-07-30 | 2020-04-01 | Blueprint Medicines Corporation | Ntrk2 fusions |
| JP2016540811A (ja) | 2013-12-20 | 2016-12-28 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | Ｎ−アシルピペリジンエーテルトロポミオシン関連キナーゼ阻害剤 |
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