JP2018108937A5 - - Google Patents
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- Publication number
- JP2018108937A5 JP2018108937A5 JP2016221064A JP2016221064A JP2018108937A5 JP 2018108937 A5 JP2018108937 A5 JP 2018108937A5 JP 2016221064 A JP2016221064 A JP 2016221064A JP 2016221064 A JP2016221064 A JP 2016221064A JP 2018108937 A5 JP2018108937 A5 JP 2018108937A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- hydrogen
- substituted alkyl
- optionally
- halogen
- 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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- 239000001257 hydrogen Substances 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- -1 methyl compound Chemical class 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims 46
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005647 linker group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004419 alkynylene group Chemical group 0.000 claims 3
- 125000000732 arylene group Chemical group 0.000 claims 3
- 125000004452 carbocyclyl group Chemical group 0.000 claims 3
- 125000004474 heteroalkylene group Chemical group 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 239000003999 initiator Substances 0.000 claims 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 239000011701 zinc Substances 0.000 claims 3
- 229910052725 zinc Inorganic materials 0.000 claims 3
- 102000029749 Microtubule Human genes 0.000 claims 2
- 108091022875 Microtubule Proteins 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 210000004688 microtubule Anatomy 0.000 claims 2
- 206010055113 Breast cancer metastatic Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 230000008880 microtubule cytoskeleton organization Effects 0.000 claims 1
- 230000011278 mitosis Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000002025 prostate sarcoma Diseases 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 229930195695 Halichondrin Natural products 0.000 description 6
- 125000000468 ketone group Chemical group 0.000 description 4
- 229930194670 homohalichondrin Natural products 0.000 description 2
- 0 CCC*(OC[C@@](*C(C1O)OC*)O[C@@](CCCCC(*)(*)CCC[C@@]2O[C@](C[C@@]([C@](C*)C3*)OC4C3O[C@](CC)[C@]([*+2])C4)C(*)(*)C(*)C2)C(*)C1(*)O)=CC(S)=O Chemical compound CCC*(OC[C@@](*C(C1O)OC*)O[C@@](CCCCC(*)(*)CCC[C@@]2O[C@](C[C@@]([C@](C*)C3*)OC4C3O[C@](CC)[C@]([*+2])C4)C(*)(*)C(*)C2)C(*)C1(*)O)=CC(S)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- UFNVPOGXISZXJD-XJPMSQCNSA-N eribulin Chemical compound C([C@H]1CC[C@@H]2O[C@@H]3[C@H]4O[C@H]5C[C@](O[C@H]4[C@H]2O1)(O[C@@H]53)CC[C@@H]1O[C@H](C(C1)=C)CC1)C(=O)C[C@@H]2[C@@H](OC)[C@@H](C[C@H](O)CN)O[C@H]2C[C@@H]2C(=C)[C@H](C)C[C@H]1O2 UFNVPOGXISZXJD-XJPMSQCNSA-N 0.000 description 1
- 229960003649 eribulin Drugs 0.000 description 1
- GIEQUQHFFCIXFP-GVEGDGMYSA-N halichondrin a Chemical compound O([C@@H]1[C@@H](C)[C@@H]2O[C@@H]3C[C@@]4(O[C@H]5[C@@H](C)C[C@@]6(C[C@@H]([C@@H]7O[C@@H](C[C@@H]7O6)[C@@H](O)C[C@@H](O)CO)C)O[C@H]5C4)O[C@@H]3C[C@@H]2O[C@H]1C[C@@H]1C(=C)[C@H](C)C[C@@H](O1)CC[C@H]1C(=C)C[C@@H](O1)CC1)C(=O)C[C@H](O2)CC[C@H](O[C@@H]34)[C@H]2[C@H](O2)[C@@H]4O[C@@]4(O)[C@@H]3O[C@@]12[C@@H]4O GIEQUQHFFCIXFP-GVEGDGMYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229930190448 norhalichondrin Natural products 0.000 description 1
- NMWGUXUJLUPRSU-UHFFFAOYSA-N norhalichondrin A Natural products O1C2C(C)CC3(OC4CC(O)C(CC(O)=O)OC4C(C)C3)OC2CC1(OC1CC2OC3CC4C(=C)C(C)CC(O4)CCC4C(=C)CC(O4)CC4)CC1OC2C(C)C3OC(=O)CC(O1)CCC(OC23)C1C(O1)C3OC3(O)C2OC41C3O NMWGUXUJLUPRSU-UHFFFAOYSA-N 0.000 description 1
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016221064A JP6978758B2 (ja) | 2016-11-11 | 2016-11-11 | パラジウム媒介ケトール化 |
| US15/809,845 US10392400B2 (en) | 2016-11-11 | 2017-11-10 | Palladium-mediated ketolization |
| US16/459,120 US10844073B2 (en) | 2016-11-11 | 2019-07-01 | Palladium-mediated ketolization |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016221064A JP6978758B2 (ja) | 2016-11-11 | 2016-11-11 | パラジウム媒介ケトール化 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018108937A JP2018108937A (ja) | 2018-07-12 |
| JP2018108937A5 true JP2018108937A5 (enExample) | 2019-12-26 |
| JP6978758B2 JP6978758B2 (ja) | 2021-12-08 |
Family
ID=62240368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016221064A Active JP6978758B2 (ja) | 2016-11-11 | 2016-11-11 | パラジウム媒介ケトール化 |
Country Status (2)
| Country | Link |
|---|---|
| US (2) | US10392400B2 (enExample) |
| JP (1) | JP6978758B2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017520586A (ja) | 2014-06-30 | 2017-07-27 | プレジデント アンド フェローズ オブ ハーバード カレッジ | ハリコンドリン類似体の合成およびその使用 |
| WO2016176560A1 (en) | 2015-04-30 | 2016-11-03 | President And Fellows Of Harvard College | Chromium-mediated coupling and application to the synthesis of halichondrins |
| JP6978758B2 (ja) | 2016-11-11 | 2021-12-08 | プレジデント アンド フェローズ オブ ハーバード カレッジ | パラジウム媒介ケトール化 |
| HRP20221385T1 (hr) | 2017-04-05 | 2023-01-06 | President And Fellows Of Harvard College | Makrociklički spoj i njegova uporaba |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| US11548898B2 (en) | 2017-07-06 | 2023-01-10 | President And Fellows Of Harvard College | Synthesis of halichondrins |
| US11498892B2 (en) | 2017-07-06 | 2022-11-15 | President And Fellows Of Harvard College | Fe/Cu-mediated ketone synthesis |
| EP3710454B1 (en) | 2017-11-15 | 2024-01-03 | President And Fellows Of Harvard College | Macrocyclic compounds and uses thereof |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5338865A (en) | 1992-03-12 | 1994-08-16 | President And Fellows Of Harvard College | Synthesis of halichondrin B and norhalichondrin B |
| US5436238A (en) | 1992-03-12 | 1995-07-25 | President And Fellows Of Harvard College | Halichondrins and related compounds |
| GB9206244D0 (en) | 1992-03-23 | 1992-05-06 | Pharma Mar Sa | Cytotoxic compound from a marine sponge |
| US5426194A (en) | 1993-01-19 | 1995-06-20 | Arizona Board Of Regents, A Body Corporate Acting On Behalf Of Arizona State University | Isolation and structure of Halistatin 1 |
| US5352804A (en) | 1993-01-19 | 1994-10-04 | Arizona Board Of Regents, A Body Corporate, Acting On Behalf Of Arizona State University | Isolation and structure of Halistatin 2 |
| IL139960A0 (en) | 1998-06-17 | 2002-02-10 | Eisai Co Ltd | Macrocylic analogs and methods of their use and preparation |
| US8097648B2 (en) | 1998-06-17 | 2012-01-17 | Eisai R&D Management Co., Ltd. | Methods and compositions for use in treating cancer |
| US6653341B1 (en) | 1998-06-17 | 2003-11-25 | Eisai Co., Ltd. | Methods and compositions for use in treating cancer |
| JP2001305734A (ja) * | 2000-04-20 | 2001-11-02 | Fuji Photo Film Co Ltd | 光重合性組成物 |
| JP2003261447A (ja) | 2002-03-07 | 2003-09-16 | Kyosei Seiyaku Kk | 抗腫瘍剤 |
| PL2522663T3 (pl) | 2004-06-03 | 2015-08-31 | Eisai R&D Man Co Ltd | Produkty pośrednie do otrzymywania halichondryny B |
| WO2006076100A2 (en) | 2004-12-09 | 2006-07-20 | Eisai Co. Ltd. | Tubulin isotype screening in cancer therapy using halichondrin b analogs |
| JP2009184924A (ja) | 2006-05-31 | 2009-08-20 | Eisai R & D Management Co Ltd | 生物学的試薬用化合物 |
| WO2008112137A1 (en) | 2007-03-07 | 2008-09-18 | Interdigital Technology Corporation | Method and apparatus for generating and processing a mac-ehs protocol data unit |
| JP2010530437A (ja) | 2007-06-18 | 2010-09-09 | メディミューン，エルエルシー | ＥｐｈＡ２およびＥｒｂＢ２を発現する細胞の相乗的治療 |
| EP2578576B9 (en) | 2007-10-03 | 2016-09-14 | Eisai R&D Management Co., Ltd. | Intermediates for the synthesis of halichondrin B analogs |
| CA2705383A1 (en) | 2007-11-16 | 2009-05-22 | Eisai R&D Management Co., Ltd. | Novel intermediate for halichondrin b analog synthesis and novel desulfonylation reaction used for the intermediate |
| US8598373B2 (en) | 2008-04-04 | 2013-12-03 | Eisai R&D Management Co., Ltd. | Halichondrin B analogs |
| SG182612A1 (en) | 2010-01-26 | 2012-08-30 | Eisai R&D Man Co Ltd | Furo [3, 2 -b] pyrane derivatives useful in the synthesis of halichondrin b analogs |
| CA2824154A1 (en) | 2011-01-10 | 2012-07-19 | President And Fellows Of Harvard College | Method for delivering agents into cells using bacterial toxins |
| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| JP2015501818A (ja) | 2011-12-16 | 2015-01-19 | アルフォラ リサーチ インコーポレイテッドＡｌｐｈｏｒａ Ｒｅｓｅａｒｃｈ Ｉｎｃ． | ３−（（２ｓ，５ｓ）−４−メチレン−５−（３−オキソプロピル）テトラヒドロフラン−２−イル）プロパノール誘導体およびそれらの有用な中間体を調製する方法 |
| IN2014MN01521A (enExample) | 2011-12-29 | 2015-05-01 | Alphora Res Inc | |
| WO2013142999A1 (en) | 2012-03-30 | 2013-10-03 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein |
| JP6511613B2 (ja) | 2013-07-03 | 2019-05-15 | サンド・アクチエンゲゼルシヤフト | ハリコンドリンＢの大環状Ｃ１−ケト類似体の製造のための合成方法及び該方法に有用な中間体、例えば−ＳＯ２−（ｐ−トリル）基を含有する中間体 |
| HUE049387T2 (hu) | 2013-11-04 | 2020-09-28 | Eisai R&D Man Co Ltd | A halichondrin B analógjainak szintézisében hasznos makrociklizációs reakciók és köztitermékek |
| SG11201604545XA (en) | 2013-12-06 | 2016-07-28 | Eisai R&D Man Co Ltd | Methods useful in the synthesis of halichondrin b analogs |
| JP2017520586A (ja) | 2014-06-30 | 2017-07-27 | プレジデント アンド フェローズ オブ ハーバード カレッジ | ハリコンドリン類似体の合成およびその使用 |
| WO2016038624A1 (en) | 2014-09-09 | 2016-03-17 | Cipla Limited | "process for the preparation of macrocyclic ketone analogs of halichondrin b or pharmaceutically acceptable salts and intermediates thereof" |
| WO2016176560A1 (en) * | 2015-04-30 | 2016-11-03 | President And Fellows Of Harvard College | Chromium-mediated coupling and application to the synthesis of halichondrins |
| KR102743950B1 (ko) | 2015-05-07 | 2024-12-18 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 할리콘드린 마크롤라이드의 합성에 유용한 마크로고리화 반응 및 중간체 및 기타 단편 |
| JP6978758B2 (ja) | 2016-11-11 | 2021-12-08 | プレジデント アンド フェローズ オブ ハーバード カレッジ | パラジウム媒介ケトール化 |
| HRP20221385T1 (hr) | 2017-04-05 | 2023-01-06 | President And Fellows Of Harvard College | Makrociklički spoj i njegova uporaba |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| US11548898B2 (en) | 2017-07-06 | 2023-01-10 | President And Fellows Of Harvard College | Synthesis of halichondrins |
| US11498892B2 (en) | 2017-07-06 | 2022-11-15 | President And Fellows Of Harvard College | Fe/Cu-mediated ketone synthesis |
-
2016
- 2016-11-11 JP JP2016221064A patent/JP6978758B2/ja active Active
-
2017
- 2017-11-10 US US15/809,845 patent/US10392400B2/en active Active
-
2019
- 2019-07-01 US US16/459,120 patent/US10844073B2/en active Active
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