JP2016525076A5 - - Google Patents
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- Publication number
- JP2016525076A5 JP2016525076A5 JP2016520444A JP2016520444A JP2016525076A5 JP 2016525076 A5 JP2016525076 A5 JP 2016525076A5 JP 2016520444 A JP2016520444 A JP 2016520444A JP 2016520444 A JP2016520444 A JP 2016520444A JP 2016525076 A5 JP2016525076 A5 JP 2016525076A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- alkyl
- ethoxy
- difluorobenzyl
- pyrazol
- 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.)
- Pending
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 38
- 239000001257 hydrogen Substances 0.000 claims 38
- 150000002431 hydrogen Chemical group 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 150000001204 N-oxides Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000011780 sodium chloride Substances 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 4
- -1 bromo, cyano, methyl Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 3
- 229940064982 ethylnicotinate Drugs 0.000 claims 3
- 230000003463 hyperproliferative Effects 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 210000004369 Blood Anatomy 0.000 claims 2
- 206010027476 Metastasis Diseases 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 239000008280 blood Substances 0.000 claims 2
- 230000030833 cell death Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 230000001939 inductive effect Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 235000005152 nicotinamide Nutrition 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- VNVLBWOVSDGPGB-UHFFFAOYSA-N 1-[(4-ethoxy-2,6-difluorophenyl)methyl]-3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]-5-methylpyrazole-4-carbonitrile Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(C)=C(C#N)C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 VNVLBWOVSDGPGB-UHFFFAOYSA-N 0.000 claims 1
- NVRIRSHAVAGFSB-UHFFFAOYSA-N 2-[(4-ethoxy-2,6-difluorophenyl)methyl]-5-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]-4-methylpyrazole-3-carbonitrile Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(C#N)=C(C)C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 NVRIRSHAVAGFSB-UHFFFAOYSA-N 0.000 claims 1
- RMGMAJVXTDNFKS-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-4-fluoro-5-methylpyrazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(C)=C(F)C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 RMGMAJVXTDNFKS-UHFFFAOYSA-N 0.000 claims 1
- QKYAVYXVDRYVBQ-UHFFFAOYSA-N 2-[4-bromo-1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5-methylpyrazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(C)=C(Br)C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 QKYAVYXVDRYVBQ-UHFFFAOYSA-N 0.000 claims 1
- QEUXFRNHMYQONM-UHFFFAOYSA-N 2-[4-chloro-1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5-methylpyrazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(C)=C(Cl)C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 QEUXFRNHMYQONM-UHFFFAOYSA-N 0.000 claims 1
- BWGWLWRYALPARD-UHFFFAOYSA-N 2-[4-chloro-1-[(4-ethoxy-2,6-difluorophenyl)methyl]pyrazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1N=C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)C(Cl)=C1 BWGWLWRYALPARD-UHFFFAOYSA-N 0.000 claims 1
- AUNYPPTVZNLDLA-UHFFFAOYSA-N 2-[5-bromo-1-[(4-ethoxy-2,6-difluorophenyl)methyl]-4-methylpyrazol-3-yl]-5-methoxy-N-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(Br)=C(C)C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 AUNYPPTVZNLDLA-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- DZASXIKIJHWUBO-UHFFFAOYSA-N 4-[[2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-4-fluoro-5-methylpyrazol-3-yl]-5-methoxypyrimidin-4-yl]amino]-N-methylpyridine-3-carboxamide Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(C)=C(F)C(C=2N=C(NC=3C(=CN=CC=3)C(=O)NC)C(OC)=CN=2)=N1 DZASXIKIJHWUBO-UHFFFAOYSA-N 0.000 claims 1
- IACLWSUNELJRCP-UHFFFAOYSA-N 4-[[2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-4-fluoro-5-methylpyrazol-3-yl]-5-methoxypyrimidin-4-yl]amino]pyridine-3-carboxylic acid Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(C)=C(F)C(C=2N=C(NC=3C(=CN=CC=3)C(O)=O)C(OC)=CN=2)=N1 IACLWSUNELJRCP-UHFFFAOYSA-N 0.000 claims 1
- QBKVTQFCORLPOG-UHFFFAOYSA-N 4-[[2-[4-chloro-1-[(4-ethoxy-2,6-difluorophenyl)methyl]pyrazol-3-yl]-5-methoxypyrimidin-4-yl]amino]pyridine-3-carboxylic acid Chemical compound FC1=CC(OCC)=CC(F)=C1CN1N=C(C=2N=C(NC=3C(=CN=CC=3)C(O)=O)C(OC)=CN=2)C(Cl)=C1 QBKVTQFCORLPOG-UHFFFAOYSA-N 0.000 claims 1
- IDPYNHYLBQNVSL-UHFFFAOYSA-N 4-[[2-[4-chloro-5-cyclopropyl-1-[(4-ethoxy-2,6-difluorophenyl)methyl]pyrazol-3-yl]pyrimidin-4-yl]amino]-N-methylpyridine-3-carboxamide Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(C2CC2)=C(Cl)C(C=2N=C(NC=3C(=CN=CC=3)C(=O)NC)C=CN=2)=N1 IDPYNHYLBQNVSL-UHFFFAOYSA-N 0.000 claims 1
- MKUKDICMGWXEMU-UHFFFAOYSA-N 4-[[2-[4-chloro-5-cyclopropyl-1-[(4-ethoxy-2,6-difluorophenyl)methyl]pyrazol-3-yl]pyrimidin-4-yl]amino]pyridine-3-carboxylic acid Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(C2CC2)=C(Cl)C(C=2N=C(NC=3C(=CN=CC=3)C(O)=O)C=CN=2)=N1 MKUKDICMGWXEMU-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- LVBXHVMDEIVANQ-UHFFFAOYSA-N ClC=1C(=NN(C=1C1CC1)CC1=C(C=C(C=C1F)OCC)F)C1=NC=CC(=N1)NC1=CC=NC=C1 Chemical compound ClC=1C(=NN(C=1C1CC1)CC1=C(C=C(C=C1F)OCC)F)C1=NC=CC(=N1)NC1=CC=NC=C1 LVBXHVMDEIVANQ-UHFFFAOYSA-N 0.000 claims 1
- 230000000240 adjuvant Effects 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 230000000973 chemotherapeutic Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- KFUSANSHCADHNJ-UHFFFAOYSA-N pyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CC=CN=C1 KFUSANSHCADHNJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- GYPBSIFOIFDXKX-UHFFFAOYSA-N C=COCC1(CN)COC1 Chemical compound C=COCC1(CN)COC1 GYPBSIFOIFDXKX-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13173276.0 | 2013-06-21 | ||
| EP13173276 | 2013-06-21 | ||
| PCT/EP2014/062696 WO2014202590A1 (en) | 2013-06-21 | 2014-06-17 | Substituted benzylpyrazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016525076A JP2016525076A (ja) | 2016-08-22 |
| JP2016525076A5 true JP2016525076A5 (pt-PT) | 2017-07-20 |
Family
ID=48651935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016520444A Pending JP2016525076A (ja) | 2013-06-21 | 2014-06-17 | 置換されたベンジルピラゾール類 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9765058B2 (pt-PT) |
| EP (1) | EP3010904A1 (pt-PT) |
| JP (1) | JP2016525076A (pt-PT) |
| CN (1) | CN105408324A (pt-PT) |
| CA (1) | CA2916116A1 (pt-PT) |
| HK (1) | HK1221717A1 (pt-PT) |
| WO (1) | WO2014202590A1 (pt-PT) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA111754C2 (uk) | 2011-10-06 | 2016-06-10 | Байєр Фарма Акцієнгезелльшафт | Заміщені бензиліндазоли для застосування як інгібіторів bub1-кінази для лікування гіперпроліферативних захворювань |
| ES2638144T3 (es) | 2011-12-21 | 2017-10-18 | Bayer Intellectual Property Gmbh | Bencilpirazoles sustituidos |
| US20160046604A1 (en) * | 2013-03-21 | 2016-02-18 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted indazoles |
| US9745285B2 (en) | 2013-06-21 | 2017-08-29 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| WO2015063003A1 (en) | 2013-10-30 | 2015-05-07 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| AR100886A1 (es) | 2014-06-17 | 2016-11-09 | Bayer Pharma AG | 3-amino-1,5,6,7-tetrahidro-4h-indol-4-onas |
| WO2016042084A1 (en) | 2014-09-19 | 2016-03-24 | Bayer Pharma Aktiengesellschaft | Benzyl substituted indazoles as bub1 inhibitors |
| MY182181A (en) | 2015-01-28 | 2021-01-18 | Bayer Pharma AG | 4h-pyrrolo[3,2-c]pyridin-4-one derivatives |
| WO2016202755A1 (en) | 2015-06-17 | 2016-12-22 | Bayer Pharma Aktiengesellschaft | 3-amino-1,5,6,7-tetrahydro-4h-indol-4-ones |
| JP2019504826A (ja) * | 2015-12-16 | 2019-02-21 | バイエル ファーマ アクチエンゲゼルシャフト | ヘテロ−１，５，６，７−テトラヒドロ−４ｈ−インドール−４−オン類 |
| WO2017148995A1 (en) | 2016-03-04 | 2017-09-08 | Bayer Pharma Aktiengesellschaft | 1-(pyrimidin-2-yl)-1h-indazoles having bub1 kinase inhibiting activity |
| WO2017157991A1 (en) | 2016-03-18 | 2017-09-21 | Bayer Pharma Aktiengesellschaft | 1-alkyl-pyrazoles and -indazoles as bub1 inhibitors for the treatment of hyperproliferative diseases |
| WO2017157992A1 (en) | 2016-03-18 | 2017-09-21 | Bayer Pharma Aktiengesellschaft | Annulated pyrazoles as bub1 kinase inhibitors for treating proliferative disorders |
| WO2018122168A1 (en) | 2016-12-29 | 2018-07-05 | Bayer Pharma Aktiengesellschaft | Combinations of bub1 kinase and parp inhibitors |
| WO2018158175A1 (en) | 2017-02-28 | 2018-09-07 | Bayer Pharma Aktiengesellschaft | Combination of bub1 inhibitors |
| WO2018206547A1 (en) | 2017-05-12 | 2018-11-15 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and atr inhibitors |
| WO2018215282A1 (en) | 2017-05-26 | 2018-11-29 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and pi3k inhibitors |
| CA3196712A1 (en) | 2020-09-23 | 2022-03-31 | Scorpion Therapeutics, Inc. | Pyrrolo[3,2-c]pyridin-4-one derivatives useful in the treatment of cancer |
| WO2022072645A2 (en) | 2020-09-30 | 2022-04-07 | Scorpion Therapeutics, Inc. | Methods for treating cancer |
| WO2022072634A1 (en) | 2020-09-30 | 2022-04-07 | Scorpion Therapeutics, Inc. | Bicyclic compounds for use in the treatment cancer |
| AU2021358596A1 (en) | 2020-10-09 | 2023-05-25 | Scorpion Therapeutics, Inc. | Heterocyclic inhibitors of egfr and/or her2, for use in the treatment of cancer |
| WO2022094271A1 (en) | 2020-10-30 | 2022-05-05 | Scorpion Therapeutics, Inc. | Methods for treating cancer |
| WO2022098992A1 (en) | 2020-11-05 | 2022-05-12 | Scorpion Therapeutics, Inc. | Use of macrocyclic compounds in methods of treating cancer |
| CN112843065B (zh) * | 2021-01-20 | 2022-03-01 | 黑龙江中医药大学 | 一种用于认知障碍的药物及其制备方法 |
| WO2022197913A1 (en) | 2021-03-18 | 2022-09-22 | Scorpion Therapeutics, Inc. | Bicyclic derivatives which can be used to treat cancer |
| WO2023173083A1 (en) | 2022-03-11 | 2023-09-14 | Scorpion Therapeutics, Inc. | Tetrahydroindole derivatives as egfr and/or her2 inhibtors useful for the treatment of cancer |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| US5470862A (en) | 1995-02-03 | 1995-11-28 | Ohmeda Pharmaceutical Products Division Inc. | Substituted pyrazolyl compounds and methods employing such compounds |
| EP1254105A1 (de) | 2000-02-10 | 2002-11-06 | Lonza AG | Verfahren zur herstellung von alkoxymalonsäuredinitrilen |
| US7863282B2 (en) * | 2003-03-14 | 2011-01-04 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| WO2011049987A2 (en) | 2009-10-20 | 2011-04-28 | Eiger Biopharmaceuticals, Inc. | Azaindazoles to treat flaviviridae virus infection |
| US20130178475A1 (en) | 2010-03-17 | 2013-07-11 | Ironwood Pharmaceuticals, Inc. | sGC STIMULATORS |
| KR101955691B1 (ko) | 2010-03-30 | 2019-03-07 | 베르선 코포레이션 | 트롬빈 억제제로서의 다중치환된 방향족 화합물 |
| JP5860459B2 (ja) * | 2010-06-30 | 2016-02-16 | アイアンウッド ファーマシューティカルズ インコーポレイテッド | ｓＧＣ刺激薬 |
| UA111754C2 (uk) | 2011-10-06 | 2016-06-10 | Байєр Фарма Акцієнгезелльшафт | Заміщені бензиліндазоли для застосування як інгібіторів bub1-кінази для лікування гіперпроліферативних захворювань |
| ES2638144T3 (es) * | 2011-12-21 | 2017-10-18 | Bayer Intellectual Property Gmbh | Bencilpirazoles sustituidos |
| WO2013101830A1 (en) | 2011-12-27 | 2013-07-04 | Ironwood Pharmaceuticals, Inc. | 2 - benzyl, 3 - (pyrimidin- 2 -yl) substituted pyrazoles useful as sgc stimulators |
| JP2015520143A (ja) | 2012-05-11 | 2015-07-16 | バイエル ファーマ アクチエンゲゼルシャフト | 癌を治療するためのｂｕｂ１阻害薬としての置換されているシクロアルケノピラゾール類 |
| WO2014047111A1 (en) | 2012-09-18 | 2014-03-27 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| EP2897953B8 (en) | 2012-09-19 | 2019-06-26 | Cyclerion Therapeutics, Inc. | Sgc stimulators |
| US20160046604A1 (en) | 2013-03-21 | 2016-02-18 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted indazoles |
| US20160052912A1 (en) | 2013-03-21 | 2016-02-25 | Bayer Pharma Akitiengesellschaft | Diaminoheteroaryl substituted indazoles |
| US20160046610A1 (en) | 2013-03-21 | 2016-02-18 | Bayer Pharma Aktiengesellschaft | 3-heteroaryl substituted indazoles |
| US9745285B2 (en) | 2013-06-21 | 2017-08-29 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| WO2014202583A1 (en) | 2013-06-21 | 2014-12-24 | Bayer Pharma Aktiengesellschaft | Substituted benzylpyrazoles |
| US20160145267A1 (en) | 2013-06-21 | 2016-05-26 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| CA2916109A1 (en) | 2013-06-21 | 2014-12-24 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| US20170275270A1 (en) | 2014-09-19 | 2017-09-28 | Bayer Pharma Aktiengesellschaft | Benzyl substituted indazoles |
| EP3194381A1 (en) | 2014-09-19 | 2017-07-26 | Bayer Pharma Aktiengesellschaft | Benzyl substituted indazoles as bub1 kinase inhibitors |
| JP2017535514A (ja) | 2014-09-19 | 2017-11-30 | バイエル ファーマ アクチエンゲゼルシャフト | Ｂｕｂ１キナーゼ阻害薬としてのベンジル置換インダゾール類 |
| WO2016042084A1 (en) | 2014-09-19 | 2016-03-24 | Bayer Pharma Aktiengesellschaft | Benzyl substituted indazoles as bub1 inhibitors |
-
2014
- 2014-06-17 US US14/900,599 patent/US9765058B2/en not_active Expired - Fee Related
- 2014-06-17 CN CN201480043464.9A patent/CN105408324A/zh active Pending
- 2014-06-17 WO PCT/EP2014/062696 patent/WO2014202590A1/en active Application Filing
- 2014-06-17 JP JP2016520444A patent/JP2016525076A/ja active Pending
- 2014-06-17 CA CA2916116A patent/CA2916116A1/en not_active Abandoned
- 2014-06-17 EP EP14731247.4A patent/EP3010904A1/en not_active Withdrawn
-
2016
- 2016-08-17 HK HK16109821.8A patent/HK1221717A1/zh unknown
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