JP2015536325A5 - - Google Patents
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- JP2015536325A5 JP2015536325A5 JP2015537799A JP2015537799A JP2015536325A5 JP 2015536325 A5 JP2015536325 A5 JP 2015536325A5 JP 2015537799 A JP2015537799 A JP 2015537799A JP 2015537799 A JP2015537799 A JP 2015537799A JP 2015536325 A5 JP2015536325 A5 JP 2015536325A5
- Authority
- JP
- Japan
- Prior art keywords
- stereoisomer
- pharmaceutically acceptable
- prodrug
- tautomer
- compound
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 173
- 239000000651 prodrug Substances 0.000 claims description 95
- 229940002612 prodrug Drugs 0.000 claims description 95
- 150000003839 salts Chemical class 0.000 claims description 95
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- -1 amino acid ester Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 101001091538 Homo sapiens Pyruvate kinase PKM Proteins 0.000 claims description 5
- 102100034911 Pyruvate kinase PKM Human genes 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 0 C=*c1cccc(P)c1N Chemical compound C=*c1cccc(P)c1N 0.000 description 5
- CPCWRGPJUDZREC-UHFFFAOYSA-N Cc(cccc1N2)c1SC2=O Chemical compound Cc(cccc1N2)c1SC2=O CPCWRGPJUDZREC-UHFFFAOYSA-N 0.000 description 1
- ABLADXPKDITIOC-UHFFFAOYSA-N Cc1c(c(F)c[nH]2)c2ccc1 Chemical compound Cc1c(c(F)c[nH]2)c2ccc1 ABLADXPKDITIOC-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N Cc1cccc2c1cc[nH]2 Chemical compound Cc1cccc2c1cc[nH]2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- QCXGJTGMGJOYDP-UHFFFAOYSA-N Cc1cccc2c1nc[nH]2 Chemical compound Cc1cccc2c1nc[nH]2 QCXGJTGMGJOYDP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261714659P | 2012-10-16 | 2012-10-16 | |
| US61/714,659 | 2012-10-16 | ||
| US201361875855P | 2013-09-10 | 2013-09-10 | |
| US61/875,855 | 2013-09-10 | ||
| PCT/US2013/065296 WO2014062838A2 (en) | 2012-10-16 | 2013-10-16 | Pkm2 modulators and methods for their use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017203963A Division JP6526767B2 (ja) | 2012-10-16 | 2017-10-20 | Ｐｋｍ２調節因子およびそれらの使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015536325A JP2015536325A (ja) | 2015-12-21 |
| JP2015536325A5 true JP2015536325A5 (https=) | 2016-12-01 |
| JP6243918B2 JP6243918B2 (ja) | 2017-12-06 |
Family
ID=50488890
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015537799A Active JP6243918B2 (ja) | 2012-10-16 | 2013-10-16 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2017203963A Expired - Fee Related JP6526767B2 (ja) | 2012-10-16 | 2017-10-20 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2018186629A Withdrawn JP2019023209A (ja) | 2012-10-16 | 2018-10-01 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2020035656A Withdrawn JP2020105190A (ja) | 2012-10-16 | 2020-03-03 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2020035657A Withdrawn JP2020097631A (ja) | 2012-10-16 | 2020-03-03 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2021120679A Active JP7128331B2 (ja) | 2012-10-16 | 2021-07-21 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2021129580A Pending JP2021181467A (ja) | 2012-10-16 | 2021-08-06 | Ｐｋｍ２調節因子およびそれらの使用方法 |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017203963A Expired - Fee Related JP6526767B2 (ja) | 2012-10-16 | 2017-10-20 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2018186629A Withdrawn JP2019023209A (ja) | 2012-10-16 | 2018-10-01 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2020035656A Withdrawn JP2020105190A (ja) | 2012-10-16 | 2020-03-03 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2020035657A Withdrawn JP2020097631A (ja) | 2012-10-16 | 2020-03-03 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2021120679A Active JP7128331B2 (ja) | 2012-10-16 | 2021-07-21 | Ｐｋｍ２調節因子およびそれらの使用方法 |
| JP2021129580A Pending JP2021181467A (ja) | 2012-10-16 | 2021-08-06 | Ｐｋｍ２調節因子およびそれらの使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (5) | US9394257B2 (https=) |
| EP (1) | EP2909181B1 (https=) |
| JP (7) | JP6243918B2 (https=) |
| DK (1) | DK2909181T3 (https=) |
| ES (1) | ES2644758T3 (https=) |
| WO (1) | WO2014062838A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2909181T3 (da) * | 2012-10-16 | 2017-11-20 | Tolero Pharmaceuticals Inc | PKM2-modulatorer og fremgangsmåder til anvendelse deraf |
| ES2747768T3 (es) | 2017-03-20 | 2020-03-11 | Forma Therapeutics Inc | Composiciones de pirrolopirrol como activadores de quinasa de piruvato (PKR) |
| US20200237766A1 (en) | 2017-10-13 | 2020-07-30 | Tolero Pharmaceuticals, Inc. | Pkm2 activators in combination with reactive oxygen species for treatment of cancer |
| ES2989438T3 (es) | 2018-09-19 | 2024-11-26 | Novo Nordisk Healthcare Ag | Activación de la piruvato cinasa R |
| US12053458B2 (en) | 2018-09-19 | 2024-08-06 | Novo Nordisk Health Care Ag | Treating sickle cell disease with a pyruvate kinase R activating compound |
| JP2022527451A (ja) * | 2019-03-22 | 2022-06-02 | スミトモ ダイニッポン ファーマ オンコロジー， インコーポレイテッド | Ｐｋｍ２モジュレーターおよびその使用方法 |
| CA3133460A1 (en) | 2019-03-22 | 2020-10-01 | Sumitomo Dainippon Pharma Oncology, Inc. | Compositions comprising pkm2 modulators and methods of treatment using the same |
| TN2022000028A1 (en) | 2019-08-06 | 2023-10-09 | Biocryst Pharm Inc | Process-scale synthesis of a plasma kallikrein inhibitor |
| US20220378756A1 (en) | 2019-09-19 | 2022-12-01 | Forma Therapeutics, Inc. | Activating pyruvate kinase r |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
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-
2013
- 2013-10-16 DK DK13847643.7T patent/DK2909181T3/da active
- 2013-10-16 US US14/435,976 patent/US9394257B2/en active Active
- 2013-10-16 JP JP2015537799A patent/JP6243918B2/ja active Active
- 2013-10-16 ES ES13847643.7T patent/ES2644758T3/es active Active
- 2013-10-16 WO PCT/US2013/065296 patent/WO2014062838A2/en not_active Ceased
- 2013-10-16 EP EP13847643.7A patent/EP2909181B1/en active Active
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2016
- 2016-06-15 US US15/183,581 patent/US10207996B2/en active Active
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2017
- 2017-10-20 JP JP2017203963A patent/JP6526767B2/ja not_active Expired - Fee Related
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2018
- 2018-10-01 JP JP2018186629A patent/JP2019023209A/ja not_active Withdrawn
- 2018-12-19 US US16/226,599 patent/US10472328B2/en active Active
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2019
- 2019-09-26 US US16/584,912 patent/US10766865B2/en active Active
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2020
- 2020-03-03 JP JP2020035656A patent/JP2020105190A/ja not_active Withdrawn
- 2020-03-03 JP JP2020035657A patent/JP2020097631A/ja not_active Withdrawn
- 2020-07-15 US US16/930,254 patent/US20210002233A1/en not_active Abandoned
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2021
- 2021-07-21 JP JP2021120679A patent/JP7128331B2/ja active Active
- 2021-08-06 JP JP2021129580A patent/JP2021181467A/ja active Pending
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