JP2019503337A5 - - Google Patents
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- Publication number
- JP2019503337A5 JP2019503337A5 JP2018522784A JP2018522784A JP2019503337A5 JP 2019503337 A5 JP2019503337 A5 JP 2019503337A5 JP 2018522784 A JP2018522784 A JP 2018522784A JP 2018522784 A JP2018522784 A JP 2018522784A JP 2019503337 A5 JP2019503337 A5 JP 2019503337A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- compound
- pharmaceutically acceptable
- difluoromethyl
- formula
- 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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- 150000001875 compounds Chemical class 0.000 claims 24
- 238000006467 substitution reaction Methods 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- -1 chloro, difluoromethyl Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 2
- HVIGNZUDBVLTLU-MRXNPFEDSA-N (6R)-7-[(3,4-difluorophenyl)methyl]-6-(methoxymethyl)-2-[5-methyl-2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-5,6-dihydroimidazo[1,2-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C[C@@H]2COC)C=C(N=3)C2=NC(=NC=C2C)NC2=CC=NN2C)=O)C=CC=1F HVIGNZUDBVLTLU-MRXNPFEDSA-N 0.000 claims 1
- SAVWHYNFWSMMCC-PKLMIRHRSA-N (6R)-7-[(3,4-difluorophenyl)methyl]-6-(methoxymethyl)-2-[5-methyl-2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-5,6-dihydroimidazo[1,2-a]pyrazin-8-one ethanesulfonic acid Chemical compound CCS(O)(=O)=O.COC[C@H]1Cn2cc(nc2C(=O)N1Cc1ccc(F)c(F)c1)-c1nc(Nc2ccnn2C)ncc1C SAVWHYNFWSMMCC-PKLMIRHRSA-N 0.000 claims 1
- MDDULEPFNKVNRJ-PKLMIRHRSA-N (6R)-7-[(3,4-difluorophenyl)methyl]-6-(methoxymethyl)-2-[5-methyl-2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-5,6-dihydroimidazo[1,2-a]pyrazin-8-one hexanedioic acid Chemical compound OC(=O)CCCCC(O)=O.COC[C@H]1Cn2cc(nc2C(=O)N1Cc1ccc(F)c(F)c1)-c1nc(Nc2ccnn2C)ncc1C MDDULEPFNKVNRJ-PKLMIRHRSA-N 0.000 claims 1
- FSSJOGPPVNJQGR-AWEZNQCLSA-N (6S)-7-[(3,5-difluorophenyl)methyl]-6-methyl-2-[5-methyl-2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-5,6-dihydroimidazo[1,2-a]pyrazin-8-one Chemical compound C[C@H]1CN2C=C(N=C2C(=O)N1CC1=CC(F)=CC(F)=C1)C1=C(C)C=NC(NC2=CC=NN2C)=N1 FSSJOGPPVNJQGR-AWEZNQCLSA-N 0.000 claims 1
- SGPPRSHLSJWWBC-AWEZNQCLSA-N (6S)-7-[(3-chlorophenyl)methyl]-6-methyl-2-[2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-5,6-dihydroimidazo[1,2-a]pyrazin-8-one Chemical compound ClC=1C=C(CN2C(C=3N(C[C@@H]2C)C=C(N=3)C2=NC(=NC=C2)NC2=CC=NN2C)=O)C=CC=1 SGPPRSHLSJWWBC-AWEZNQCLSA-N 0.000 claims 1
- NXDOCYPZIGXILP-AWEZNQCLSA-N (6S)-7-[[6-(difluoromethyl)pyridin-2-yl]methyl]-6-methyl-2-[5-methyl-2-[(2-methylpyrazol-3-yl)amino]pyrimidin-4-yl]-5,6-dihydroimidazo[1,2-a]pyrazin-8-one Chemical compound FC(C1=CC=CC(=N1)CN1C(C=2N(C[C@@H]1C)C=C(N=2)C1=NC(=NC=C1C)NC1=CC=NN1C)=O)F NXDOCYPZIGXILP-AWEZNQCLSA-N 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- SCABJAMCNOWWAP-QGZVFWFLSA-N FC=1C=C(CN2C=C3N(C[C@@H]2COC)CC(=N3)C3=NC(=NC=C3C)NC3=CC=NN3C)C=CC1F Chemical compound FC=1C=C(CN2C=C3N(C[C@@H]2COC)CC(=N3)C3=NC(=NC=C3C)NC3=CC=NN3C)C=CC1F SCABJAMCNOWWAP-QGZVFWFLSA-N 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562252726P | 2015-11-09 | 2015-11-09 | |
| US62/252,726 | 2015-11-09 | ||
| US201662401351P | 2016-09-29 | 2016-09-29 | |
| US62/401,351 | 2016-09-29 | ||
| PCT/EP2016/076932 WO2017080979A1 (en) | 2015-11-09 | 2016-11-08 | Dihydroimidazopyrazinone derivatives useful in the treatment of cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019503337A JP2019503337A (ja) | 2019-02-07 |
| JP2019503337A5 true JP2019503337A5 (enExample) | 2020-04-16 |
| JP6877423B2 JP6877423B2 (ja) | 2021-05-26 |
Family
ID=57241113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018522784A Active JP6877423B2 (ja) | 2015-11-09 | 2016-11-08 | がんの処置において有用なジヒドロイミダゾピラジノン誘導体 |
Country Status (35)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10457669B2 (en) | 2015-10-21 | 2019-10-29 | Otsuka Pharmaceutical Co., Ltd. | Benzolactam compounds as protein kinase inhibitors |
| WO2017080979A1 (en) * | 2015-11-09 | 2017-05-18 | Astrazeneca Ab | Dihydroimidazopyrazinone derivatives useful in the treatment of cancer |
| GB201706327D0 (en) | 2017-04-20 | 2017-06-07 | Otsuka Pharma Co Ltd | A pharmaceutical compound |
| EP3845538B1 (en) * | 2018-10-10 | 2023-11-08 | Shenzhen TargetRx, Inc. | Dihydroimidazopyrazinone compound, composition including same, and use thereof |
| JP2022527744A (ja) | 2019-03-28 | 2022-06-06 | ジエンス ヘンルイ メデイシンカンパニー リミテッド | チエノ複素環式誘導体、この誘導体のための調製方法及び医療に関するこの誘導体の使用 |
| JP2022534224A (ja) | 2019-05-24 | 2022-07-28 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 置換縮合二環式誘導体、その調製方法、および医薬におけるその適用 |
| CN117486890A (zh) * | 2019-06-06 | 2024-02-02 | 和记黄埔医药（上海）有限公司 | 三环类化合物及其用途 |
| AU2020397222B2 (en) * | 2019-12-05 | 2023-07-06 | Astrazeneca Ab | Process and intermediates for the production of formula (i) |
| CA3160903A1 (en) * | 2019-12-06 | 2021-06-10 | Medshine Discovery Inc. | Thiazololactam compound as erk inhibitor and use thereof |
| JP2023543080A (ja) | 2020-09-29 | 2023-10-12 | 江▲蘇▼恒瑞医▲薬▼股▲フン▼有限公司 | ピロロ複素環系誘導体の結晶及びその製造方法 |
| AR126166A1 (es) * | 2021-06-18 | 2023-09-27 | Antengene Discovery Ltd | Combinación de un inhibidor de erk y un inhibidor de kras y usos de estos |
| WO2022268065A1 (en) * | 2021-06-22 | 2022-12-29 | Fochon Biosciences, Ltd. | Compounds as erk inhibitors |
| AU2022320304A1 (en) | 2021-07-27 | 2024-02-29 | Toray Industries, Inc. | Medicament for treatment and/or prevention of cancer |
| WO2023081859A1 (en) | 2021-11-04 | 2023-05-11 | Skyhawk Therapeutics, Inc. | Triazine amino derivatives for treating sca3 |
| US20250340572A1 (en) | 2022-04-27 | 2025-11-06 | Skyhawk Therapeutics, Inc. | Compositions useful for modulating splicing |
| EP4522623A1 (en) | 2022-05-12 | 2025-03-19 | Skyhawk Therapeutics, Inc. | Compositions useful for modulating splicing |
| WO2024006971A2 (en) * | 2022-07-01 | 2024-01-04 | The Scripps Research Institute | Antimalarial compounds |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4683195A (en) | 1986-01-30 | 1987-07-28 | Cetus Corporation | Process for amplifying, detecting, and/or-cloning nucleic acid sequences |
| US4683202A (en) | 1985-03-28 | 1987-07-28 | Cetus Corporation | Process for amplifying nucleic acid sequences |
| AU2003278377A1 (en) * | 2002-11-06 | 2004-06-07 | Merck Sharp And Dohme Limited | Imidazopyrazinones and imidazotriazinones derivates as gaba-a receptor anxiolytic |
| GB0520958D0 (en) * | 2005-10-14 | 2005-11-23 | Cyclacel Ltd | Compound |
| JP5178738B2 (ja) * | 2006-12-20 | 2013-04-10 | メルク・シャープ・アンド・ドーム・コーポレーション | 新規なｊｎｋ阻害剤 |
| NZ610948A (en) * | 2010-12-22 | 2014-06-27 | Janssen Pharmaceutica Nv | 5,6-dihydro-imidazo[1,2-a]pyrazin-8-ylamine derivatives useful as inhibitors of beta-secretase (bace) |
| EP2906562B1 (en) * | 2011-10-10 | 2016-10-05 | H. Lundbeck A/S | Pde9i with imidazo pyrazinone backbone |
| JP2013166727A (ja) * | 2012-02-16 | 2013-08-29 | Dainippon Sumitomo Pharma Co Ltd | ジヒドロイミダゾピラジノン誘導体 |
| AR090220A1 (es) | 2012-03-01 | 2014-10-29 | Array Biopharma Inc | Inhibidores de serina/treonina cinasa |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| US9867833B2 (en) * | 2013-12-06 | 2018-01-16 | Genentech, Inc. | Serine/threonine kinase inhibitors |
| CA2934679C (en) | 2013-12-30 | 2023-02-28 | Genentech, Inc. | Serine/threonine kinase inhibitors |
| WO2015103137A1 (en) | 2013-12-30 | 2015-07-09 | Array Biopharma Inc. | Serine/threonine kinase inhibitors |
| JP6723926B2 (ja) | 2014-04-09 | 2020-07-15 | ジェネンテック， インコーポレイテッド | 医薬の製造方法 |
| US10412619B2 (en) * | 2014-11-14 | 2019-09-10 | Qualcomm Incorporated | Buffer status report for eDCS |
| WO2016162325A1 (en) | 2015-04-07 | 2016-10-13 | Astrazeneca Ab | Substituted 3,4-dihydropyrrolo[1,2-a]pyrazin-1 (2h)-one derivatives as kinase inhibitors |
| US10238657B2 (en) | 2015-06-03 | 2019-03-26 | Js Innopharm (Shanhai) Ltd. | Heterocyclic compounds for treating psoriasis |
| US10479791B2 (en) | 2015-06-03 | 2019-11-19 | Changzhou Jiekai Pharmatech Co. Ltd | Heterocyclic compounds as ERK inhibitors |
| WO2017080979A1 (en) * | 2015-11-09 | 2017-05-18 | Astrazeneca Ab | Dihydroimidazopyrazinone derivatives useful in the treatment of cancer |
-
2016
- 2016-11-08 WO PCT/EP2016/076932 patent/WO2017080979A1/en not_active Ceased
- 2016-11-08 JP JP2018522784A patent/JP6877423B2/ja active Active
- 2016-11-08 LT LTEP16791420.9T patent/LT3374359T/lt unknown
- 2016-11-08 TN TNP/2018/000119A patent/TN2018000119A1/en unknown
- 2016-11-08 AU AU2016351813A patent/AU2016351813B2/en active Active
- 2016-11-08 SG SG11201803066VA patent/SG11201803066VA/en unknown
- 2016-11-08 MY MYPI2018000675A patent/MY197626A/en unknown
- 2016-11-08 CR CR20180316A patent/CR20180316A/es unknown
- 2016-11-08 CA CA3003549A patent/CA3003549A1/en active Pending
- 2016-11-08 HR HRP20200342TT patent/HRP20200342T1/hr unknown
- 2016-11-08 BR BR112018008397-6A patent/BR112018008397B1/pt active IP Right Grant
- 2016-11-08 MX MX2018005725A patent/MX376639B/es active IP Right Grant
- 2016-11-08 DK DK16791420.9T patent/DK3374359T3/da active
- 2016-11-08 SM SM20200152T patent/SMT202000152T1/it unknown
- 2016-11-08 SI SI201630668T patent/SI3374359T1/sl unknown
- 2016-11-08 EP EP16791420.9A patent/EP3374359B1/en active Active
- 2016-11-08 ES ES16791420T patent/ES2780650T3/es active Active
- 2016-11-08 KR KR1020187016091A patent/KR20180074788A/ko not_active Withdrawn
- 2016-11-08 TW TW105136236A patent/TWI730012B/zh not_active IP Right Cessation
- 2016-11-08 CN CN201680064567.2A patent/CN108349983B/zh active Active
- 2016-11-08 PE PE2018000611A patent/PE20181288A1/es unknown
- 2016-11-08 PT PT167914209T patent/PT3374359T/pt unknown
- 2016-11-08 ME MEP-2020-72A patent/ME03770B/me unknown
- 2016-11-08 PL PL16791420T patent/PL3374359T3/pl unknown
- 2016-11-08 EA EA201891063A patent/EA038028B1/ru unknown
- 2016-11-08 RS RS20200392A patent/RS60155B1/sr unknown
- 2016-11-08 US US15/345,537 patent/US9902731B2/en active Active
-
2018
- 2018-01-18 US US15/873,965 patent/US10202391B2/en active Active
- 2018-04-26 IL IL258953A patent/IL258953A/en active IP Right Grant
- 2018-05-03 NI NI201800058A patent/NI201800058A/es unknown
- 2018-05-07 PH PH12018500987A patent/PH12018500987A1/en unknown
- 2018-05-07 CL CL2018001226A patent/CL2018001226A1/es unknown
- 2018-05-07 SV SV2018005687A patent/SV2018005687A/es unknown
- 2018-05-07 CO CONC2018/0004857A patent/CO2018004857A2/es unknown
- 2018-06-06 ZA ZA2018/03742A patent/ZA201803742B/en unknown
-
2020
- 2020-04-02 CY CY20201100314T patent/CY1123627T1/el unknown
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