JP2017503867A5 - - Google Patents
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- JP2017503867A5 JP2017503867A5 JP2016566857A JP2016566857A JP2017503867A5 JP 2017503867 A5 JP2017503867 A5 JP 2017503867A5 JP 2016566857 A JP2016566857 A JP 2016566857A JP 2016566857 A JP2016566857 A JP 2016566857A JP 2017503867 A5 JP2017503867 A5 JP 2017503867A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- ethenopyrazolo
- methyl
- tetrahydro
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 67
- 150000003839 salts Chemical class 0.000 claims 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 18
- 229910052805 deuterium Inorganic materials 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- -1 chloro, bromo, methyl Chemical group 0.000 claims 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000002950 monocyclic group Chemical group 0.000 claims 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- JEGVYOJIPWPTPT-UHFFFAOYSA-N O1C=CC(N=CC=CN=CN=CC2=C1C=CC=C2)=O Chemical compound O1C=CC(N=CC=CN=CN=CC2=C1C=CC=C2)=O JEGVYOJIPWPTPT-UHFFFAOYSA-N 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 125000005605 benzo group Chemical group 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- HLCYYNKUQRMGOV-UHFFFAOYSA-N 2-oxa-5,9,11-triazabicyclo[11.4.0]heptadeca-1(17),3,5,7,9,11,13,15-octaene Chemical compound O1C=CN=CC=CN=CN=CC2=C1C=CC=C2 HLCYYNKUQRMGOV-UHFFFAOYSA-N 0.000 claims 3
- YDDNSSFZMUJHDB-UHFFFAOYSA-N O=C1N=NOC(C=CC=C2)=C2C=CC=CC=CC1 Chemical compound O=C1N=NOC(C=CC=C2)=C2C=CC=CC=CC1 YDDNSSFZMUJHDB-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- MCUJKSDQBZINCK-UHFFFAOYSA-N 1,10-dioxa-3,7-diazacyclotrideca-2,4,6,8-tetraen-12-one Chemical compound O1C=NC=CC=NC=COCC(C1)=O MCUJKSDQBZINCK-UHFFFAOYSA-N 0.000 claims 2
- WXRKLKAKHUURNP-UHFFFAOYSA-N 2,3-dioxa-4-azabicyclo[11.4.0]heptadeca-1(17),7,9,11,13,15-hexaen-5-one Chemical compound O1ONC(CC=CC=CC=CC2=C1C=CC=C2)=O WXRKLKAKHUURNP-UHFFFAOYSA-N 0.000 claims 2
- KFFSUSNOAAZLAY-UHFFFAOYSA-N 3,5,8,11-tetrazabicyclo[11.4.0]heptadeca-1,3,5,7,10,12,14,16-octaen-9-one Chemical compound C=1N=CN=CC=NC(C=NC=C2C=1C=CC=C2)=O KFFSUSNOAAZLAY-UHFFFAOYSA-N 0.000 claims 2
- DYGUMGGMDSQHRH-UHFFFAOYSA-N 8-thia-3,5,11-triazabicyclo[11.4.0]heptadeca-1,4,10,12,14,16-hexaen-9-one Chemical compound C=1N=CNCCSC(C=NC=C2C=1C=CC=C2)=O DYGUMGGMDSQHRH-UHFFFAOYSA-N 0.000 claims 2
- OENZWHFLHZUZIW-UHFFFAOYSA-N O1C=CN=CC=C(N=CN=CC2=C1C=CC=C2)C(=O)N Chemical compound O1C=CN=CC=C(N=CN=CC2=C1C=CC=C2)C(=O)N OENZWHFLHZUZIW-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- MMOCVTLXQMGDDJ-SECBINFHSA-N (3R)-5-chloro-6-fluoro-3-methyl-2,10-dioxa-13,17,21,22-tetrazatetracyclo[13.5.2.04,9.018,22]docosa-1(21),4(9),5,7,15,17,19-heptaen-14-one Chemical compound C[C@H]1OC2=NN3C(C=C2)=NC=C3C(=O)NCCOC2=C1C(Cl)=C(F)C=C2 MMOCVTLXQMGDDJ-SECBINFHSA-N 0.000 claims 1
- LZGKINUMUZXIKL-UHFFFAOYSA-N 1-oxa-2,3,4-triazacyclotrideca-2,4,6,8-tetraen-12-one Chemical compound O1N=NN=CC=CC=CCCC(C1)=O LZGKINUMUZXIKL-UHFFFAOYSA-N 0.000 claims 1
- RWYICWZFGZBMFK-UHFFFAOYSA-N 2-oxa-5,9,11-triazabicyclo[11.4.0]heptadeca-1(13),3,5,7,9,11,14,16-octaene-15-carboxamide Chemical compound O1C=CN=CC=CN=CN=CC2=C1C=CC(=C2)C(=O)N RWYICWZFGZBMFK-UHFFFAOYSA-N 0.000 claims 1
- HTFZDNFCQIFLAA-UHFFFAOYSA-N 3,5,11-triazabicyclo[11.4.0]heptadeca-1,3,5,7,10,12,14,16-octaen-9-one Chemical compound C=1N=CN=CC=CC(C=NC=C2C=1C=CC=C2)=O HTFZDNFCQIFLAA-UHFFFAOYSA-N 0.000 claims 1
- YMRTYJKGNCAGKP-UHFFFAOYSA-N 5-chloro-6-fluoro-3-methyl-2,10-dioxa-13,17,18,21-tetrazatetracyclo[13.5.2.04,9.018,22]docosa-1(21),4(9),5,7,15(22),16,19-heptaen-14-one Chemical compound CC1OC2=NC3=C(C=NN3C=C2)C(=O)NCCOC2=C1C(Cl)=C(F)C=C2 YMRTYJKGNCAGKP-UHFFFAOYSA-N 0.000 claims 1
- MAQISEFFLMTIKQ-UHFFFAOYSA-N 6-fluoro-3,13-dimethyl-2,10-dioxa-13,17,21,22-tetrazatetracyclo[13.5.2.04,9.018,22]docosa-1(21),4(9),5,7,15,17,19-heptaen-14-one Chemical compound CC1OC2=NN3C(C=C2)=NC=C3C(=O)N(C)CCOC2=C1C=C(F)C=C2 MAQISEFFLMTIKQ-UHFFFAOYSA-N 0.000 claims 1
- XYLJTJTWOPEYJR-UHFFFAOYSA-N 6-fluoro-3-methyl-2,10-dioxa-13,17,21,22-tetrazatetracyclo[13.5.2.04,9.018,22]docosa-1(21),4(9),5,7,15,17,19-heptaen-14-one Chemical compound CC1OC2=NN3C(C=C2)=NC=C3C(=O)NCCOC2=C1C=C(F)C=C2 XYLJTJTWOPEYJR-UHFFFAOYSA-N 0.000 claims 1
- BJFRNNPXYZRHMI-UHFFFAOYSA-N 8-oxa-3,5,11-triazabicyclo[11.4.0]heptadeca-1,4,10,12,14,16-hexaen-9-one Chemical compound C=1N=CNCCOC(C=NC=C2C=1C=CC=C2)=O BJFRNNPXYZRHMI-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- OXLZYPKVAWVKAD-UHFFFAOYSA-N C=1N=CN2C1C(N=CCOC1=C(C=NC=N2)C=CC=C1)=O Chemical compound C=1N=CN2C1C(N=CCOC1=C(C=NC=N2)C=CC=C1)=O OXLZYPKVAWVKAD-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- KPLSLSIGAXKAQN-UHFFFAOYSA-N N1=NCC(CC=CC=CC=CC=C1)=O Chemical compound N1=NCC(CC=CC=CC=CC=C1)=O KPLSLSIGAXKAQN-UHFFFAOYSA-N 0.000 claims 1
- LIOYFHQFNHHGLD-UHFFFAOYSA-N N=1C=CN2C1C(N=CCOC1=C(C=NC=C2)C=CC=C1)=O Chemical compound N=1C=CN2C1C(N=CCOC1=C(C=NC=C2)C=CC=C1)=O LIOYFHQFNHHGLD-UHFFFAOYSA-N 0.000 claims 1
- FDHRRCGVYFZARW-UHFFFAOYSA-N N=1N=CN2C1C(N=CCOC1=C(C=NC=N2)C=CC=C1)=O Chemical compound N=1N=CN2C1C(N=CCOC1=C(C=NC=N2)C=CC=C1)=O FDHRRCGVYFZARW-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- SUEAKNISOMJCOJ-UHFFFAOYSA-N O1ONN=CC=CC=CC=CC2=C1C=CC=C2 Chemical compound O1ONN=CC=CC=CC=CC2=C1C=CC=C2 SUEAKNISOMJCOJ-UHFFFAOYSA-N 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461931506P | 2014-01-24 | 2014-01-24 | |
| US61/931,506 | 2014-01-24 | ||
| US201462049326P | 2014-09-11 | 2014-09-11 | |
| US62/049,326 | 2014-09-11 | ||
| US201562106301P | 2015-01-22 | 2015-01-22 | |
| US62/106,301 | 2015-01-22 | ||
| PCT/US2015/012597 WO2015112806A2 (en) | 2014-01-24 | 2015-01-23 | Diaryl macrocycles as modulators of protein kinases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019034652A Division JP2019104748A (ja) | 2014-01-24 | 2019-02-27 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017503867A JP2017503867A (ja) | 2017-02-02 |
| JP2017503867A5 true JP2017503867A5 (enExample) | 2018-03-08 |
| JP6490713B2 JP6490713B2 (ja) | 2019-03-27 |
Family
ID=53682127
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016566857A Active JP6490713B2 (ja) | 2014-01-24 | 2015-01-23 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
| JP2019034652A Withdrawn JP2019104748A (ja) | 2014-01-24 | 2019-02-27 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
| JP2021001588A Pending JP2021063121A (ja) | 2014-01-24 | 2021-01-07 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
| JP2022110613A Active JP7356546B2 (ja) | 2014-01-24 | 2022-07-08 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
| JP2023158350A Ceased JP2023179539A (ja) | 2014-01-24 | 2023-09-22 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019034652A Withdrawn JP2019104748A (ja) | 2014-01-24 | 2019-02-27 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
| JP2021001588A Pending JP2021063121A (ja) | 2014-01-24 | 2021-01-07 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
| JP2022110613A Active JP7356546B2 (ja) | 2014-01-24 | 2022-07-08 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
| JP2023158350A Ceased JP2023179539A (ja) | 2014-01-24 | 2023-09-22 | タンパク質キナーゼのモジュレータとしてのジアリール大環状化合物 |
Country Status (35)
Families Citing this family (93)
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| ES2464461T3 (es) | 2008-09-22 | 2014-06-02 | Array Biopharma, Inc. | Compuestos de imidazo[1,2B]piridazina sustituidos como inhibidores de la TRK cinasa |
| SG196855A1 (en) | 2008-10-22 | 2014-02-13 | Array Biopharma Inc | Substituted pyrazolo[1,5-a]pyrimidine compounds as trk kinase inhibitors |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| AU2011256380C1 (en) | 2010-05-20 | 2016-09-08 | Array Biopharma Inc. | Macrocyclic compounds as Trk kinase inhibitors |
| PL3097107T3 (pl) | 2014-01-24 | 2020-01-31 | Turning Point Therapeutics, Inc. | Diarylowe związki makrocykliczne jako modulatory kinaz białkowych |
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| AU2016270803A1 (en) | 2015-06-01 | 2018-01-04 | Loxo Oncology, Inc. | Methods of diagnosing and treating cancer |
| AU2016287568B2 (en) | 2015-07-02 | 2020-08-20 | Turning Point Therapeutics, Inc. | Chiral diaryl macrocycles as modulators of protein kinases |
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| KR102772574B1 (ko) * | 2015-07-21 | 2025-02-24 | 터닝 포인트 테라퓨틱스, 인크. | 키랄 디아릴 매크로사이클 및 이것의 용도 |
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| US11278521B2 (en) | 2015-12-15 | 2022-03-22 | University Of South Florida | GAS5 binding compounds, formulations, and uses thereof |
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| US10045991B2 (en) | 2016-04-04 | 2018-08-14 | Loxo Oncology, Inc. | Methods of treating pediatric cancers |
| PL3439663T3 (pl) | 2016-04-04 | 2024-11-18 | Loxo Oncology, Inc. | Sposoby leczenia nowotworów wieku dziecięcego |
| FI3800189T3 (fi) | 2016-05-18 | 2023-07-31 | Loxo Oncology Inc | (s)-n-(5-((r)-2-(2,5-difluorifenyyli)pyrrolidin-1-yyli)pyratsolo[1,5-a]pyrimidin-3-yyli)-3-hydroksipyrrolidiini-1-karboksamidin valmistaminen |
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| TWI704148B (zh) | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ｒｅｔ激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
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| CN107586796B (zh) * | 2017-07-20 | 2021-08-06 | 暨明医药科技（苏州）有限公司 | (r)-2-(1-氨基乙基)-4-氟苯酚的合成方法 |
| JP7224334B2 (ja) | 2017-07-28 | 2023-02-17 | ターニング・ポイント・セラピューティクス・インコーポレイテッド | 大環式化合物およびその使用 |
| TWI791053B (zh) | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
| TWI812649B (zh) | 2017-10-10 | 2023-08-21 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
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