JP2020536046A5 - - Google Patents
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- JP2020536046A5 JP2020536046A5 JP2020500097A JP2020500097A JP2020536046A5 JP 2020536046 A5 JP2020536046 A5 JP 2020536046A5 JP 2020500097 A JP2020500097 A JP 2020500097A JP 2020500097 A JP2020500097 A JP 2020500097A JP 2020536046 A5 JP2020536046 A5 JP 2020536046A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- optionally
- hydrogen
- substituted alkyl
- salt
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims 166
- 239000001257 hydrogen Substances 0.000 claims 166
- 125000000547 substituted alkyl group Chemical group 0.000 claims 141
- 150000002431 hydrogen Chemical class 0.000 claims 134
- 150000001875 compounds Chemical class 0.000 claims 125
- 150000003839 salts Chemical class 0.000 claims 95
- 125000002252 acyl group Chemical group 0.000 claims 83
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 77
- 229910052736 halogen Inorganic materials 0.000 claims 73
- 150000002367 halogens Chemical class 0.000 claims 73
- 125000000623 heterocyclic group Chemical group 0.000 claims 59
- 238000000034 method Methods 0.000 claims 47
- 125000004429 atom Chemical group 0.000 claims 44
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 29
- 238000006243 chemical reaction Methods 0.000 claims 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 18
- 125000004452 carbocyclyl group Chemical group 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000003107 substituted aryl group Chemical group 0.000 claims 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 14
- 229910052759 nickel Inorganic materials 0.000 claims 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 11
- 239000003153 chemical reaction reagent Substances 0.000 claims 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 9
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 9
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 9
- 230000008878 coupling Effects 0.000 claims 8
- 238000010168 coupling process Methods 0.000 claims 8
- 238000005859 coupling reaction Methods 0.000 claims 8
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 7
- 239000003446 ligand Substances 0.000 claims 7
- 229910052726 zirconium Inorganic materials 0.000 claims 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 6
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 229910052748 manganese Inorganic materials 0.000 claims 6
- 239000011572 manganese Substances 0.000 claims 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 6
- 150000003573 thiols Chemical class 0.000 claims 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 4
- 229910007926 ZrCl Inorganic materials 0.000 claims 4
- 150000001540 azides Chemical class 0.000 claims 4
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 claims 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical group [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims 2
- TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical group CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- -1 tetraalkylammonium azide Chemical class 0.000 claims 2
- 238000006177 thiolation reaction Methods 0.000 claims 2
- 125000005270 trialkylamine group Chemical group 0.000 claims 2
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 230000000536 complexating effect Effects 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical group [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003461 sulfonyl halides Chemical class 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical group [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 0 *C[C@@]1O[C@@](CC[C@@]2(C(*)[C@@]3(*)OC45)OC4[C@]4O[C@@](CC(O[C@](C6*)[C@@](C[C@]7OCCC(*)C7(*)*)O[C@]7[C@]6O[C@](C*)[C@](*)C7)=O)CC[C@@]4O[C@@]5C3O2)CC1(*)* Chemical compound *C[C@@]1O[C@@](CC[C@@]2(C(*)[C@@]3(*)OC45)OC4[C@]4O[C@@](CC(O[C@](C6*)[C@@](C[C@]7OCCC(*)C7(*)*)O[C@]7[C@]6O[C@](C*)[C@](*)C7)=O)CC[C@@]4O[C@@]5C3O2)CC1(*)* 0.000 description 4
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023128422A JP7764432B2 (ja) | 2017-07-06 | 2023-08-07 | ハリコンドリンの合成 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762529333P | 2017-07-06 | 2017-07-06 | |
| US201762529310P | 2017-07-06 | 2017-07-06 | |
| US62/529,333 | 2017-07-06 | ||
| US62/529,310 | 2017-07-06 | ||
| PCT/US2018/041005 WO2019010363A1 (en) | 2017-07-06 | 2018-07-06 | HALICHONDRINES SYNTHESIS |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023128422A Division JP7764432B2 (ja) | 2017-07-06 | 2023-08-07 | ハリコンドリンの合成 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020536046A JP2020536046A (ja) | 2020-12-10 |
| JP2020536046A5 true JP2020536046A5 (https=) | 2021-08-12 |
| JP7370313B2 JP7370313B2 (ja) | 2023-10-27 |
Family
ID=63036376
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020500097A Active JP7370313B2 (ja) | 2017-07-06 | 2018-07-06 | ハリコンドリンの合成 |
| JP2023128422A Active JP7764432B2 (ja) | 2017-07-06 | 2023-08-07 | ハリコンドリンの合成 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023128422A Active JP7764432B2 (ja) | 2017-07-06 | 2023-08-07 | ハリコンドリンの合成 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US11548898B2 (https=) |
| EP (2) | EP3649135B1 (https=) |
| JP (2) | JP7370313B2 (https=) |
| KR (2) | KR102438417B1 (https=) |
| CN (2) | CN118515685A (https=) |
| AU (2) | AU2018297305B2 (https=) |
| BR (1) | BR112020000141A2 (https=) |
| CA (2) | CA3211559A1 (https=) |
| ES (1) | ES2940688T3 (https=) |
| HU (1) | HUE061306T2 (https=) |
| IL (3) | IL295588B2 (https=) |
| MX (1) | MX2020000142A (https=) |
| SG (1) | SG11201912342QA (https=) |
| WO (1) | WO2019010363A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10556910B2 (en) | 2014-06-30 | 2020-02-11 | President And Fellows Of Harvard College | Synthesis of halichondrin analogs and uses thereof |
| US10344038B2 (en) | 2015-04-30 | 2019-07-09 | 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 |
| ES2931533T3 (es) | 2017-04-05 | 2022-12-30 | Harvard College | Compuesto macrocíclico y usos del mismo |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| HUE061306T2 (hu) | 2017-07-06 | 2023-06-28 | Harvard College | Halikondrinok szintézise |
| US11498892B2 (en) | 2017-07-06 | 2022-11-15 | President And Fellows Of Harvard College | Fe/Cu-mediated ketone synthesis |
| CN111566113B (zh) * | 2017-11-15 | 2024-01-09 | 哈佛大学的校长及成员们 | 大环化合物及其用途 |
| CN111484393A (zh) * | 2019-01-28 | 2020-08-04 | 上海茂晟康慧科技有限公司 | 一种顺,顺-3,5-二甲基-1-环己醇的制备方法 |
| CN117820275A (zh) * | 2023-12-29 | 2024-04-05 | 上海科技大学 | 一种列净类药物及其中间体的催化合成方法 |
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| WO2012096926A2 (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 |
| CN104024237B (zh) | 2011-12-16 | 2016-02-24 | 阿方拉研究股份有限公司 | 用于制备3-((2s,5s)-4-亚甲基-5-(3-氧代丙基)四氢呋喃-2-基)丙醇衍生物的方法及其有用的中间体 |
| CN104080793B (zh) | 2011-12-29 | 2017-09-19 | 阿方拉研究股份有限公司 | 2‑((2s,3s,4r,5r)‑5‑((s)‑3‑氨基‑2‑羟基丙‑1‑基)‑4‑甲氧基‑3‑(苯磺酰甲基)四氢呋喃‑2‑基)乙醛衍生物以及它们的制备方法 |
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| CA2916537C (en) | 2013-07-03 | 2021-07-27 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein including intermediates containing -so2-(p-tolyl) groups |
| EP3689881B1 (en) | 2013-11-04 | 2022-01-12 | Eisai R&D Management Co., Ltd. | Macrocyclization reactions and intermediates useful in the synthesis of analogs of halichondrin b |
| MX384292B (es) | 2013-12-06 | 2025-03-14 | Eisai R&D Man Co Ltd | Metodos utiles en la sintesis de analogos de halicondrina b. |
| US10556910B2 (en) | 2014-06-30 | 2020-02-11 | President And Fellows Of Harvard College | Synthesis of halichondrin analogs and uses thereof |
| 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" |
| US10344038B2 (en) | 2015-04-30 | 2019-07-09 | 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 |
| EP3423105B1 (en) | 2016-03-02 | 2021-05-05 | Eisai R&D Management Co., Ltd. | Eribulin-based antibody-drug conjugates and methods of use |
| 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 |
| JP2020508315A (ja) | 2017-02-20 | 2020-03-19 | ポリフォー・アクチェンゲゼルシャフトＰｏｌｙｐｈｏｒ Ａｇ | がんを治療するための薬剤組合せ |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| ES2931533T3 (es) | 2017-04-05 | 2022-12-30 | Harvard College | Compuesto macrocíclico y usos del mismo |
| WO2019009956A1 (en) | 2017-07-06 | 2019-01-10 | President And Fellows Of Harvard College | SUMMARY OF MEDIUM MEDIATED KETONE |
| US11498892B2 (en) | 2017-07-06 | 2022-11-15 | President And Fellows Of Harvard College | Fe/Cu-mediated ketone synthesis |
| HUE061306T2 (hu) | 2017-07-06 | 2023-06-28 | Harvard College | Halikondrinok szintézise |
| CN111566113B (zh) | 2017-11-15 | 2024-01-09 | 哈佛大学的校长及成员们 | 大环化合物及其用途 |
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2018
- 2018-07-06 HU HUE18746401A patent/HUE061306T2/hu unknown
- 2018-07-06 EP EP18746401.1A patent/EP3649135B1/en active Active
- 2018-07-06 IL IL295588A patent/IL295588B2/en unknown
- 2018-07-06 KR KR1020207003432A patent/KR102438417B1/ko active Active
- 2018-07-06 IL IL307273A patent/IL307273B2/en unknown
- 2018-07-06 EP EP22214189.7A patent/EP4169924A3/en active Pending
- 2018-07-06 MX MX2020000142A patent/MX2020000142A/es unknown
- 2018-07-06 WO PCT/US2018/041005 patent/WO2019010363A1/en not_active Ceased
- 2018-07-06 KR KR1020227029591A patent/KR20220124279A/ko not_active Ceased
- 2018-07-06 JP JP2020500097A patent/JP7370313B2/ja active Active
- 2018-07-06 ES ES18746401T patent/ES2940688T3/es active Active
- 2018-07-06 CA CA3211559A patent/CA3211559A1/en active Pending
- 2018-07-06 IL IL271660A patent/IL271660B/en unknown
- 2018-07-06 CA CA3069160A patent/CA3069160C/en active Active
- 2018-07-06 BR BR112020000141-4A patent/BR112020000141A2/pt active Search and Examination
- 2018-07-06 SG SG11201912342QA patent/SG11201912342QA/en unknown
- 2018-07-06 US US16/628,504 patent/US11548898B2/en active Active
- 2018-07-06 CN CN202410481438.XA patent/CN118515685A/zh active Pending
- 2018-07-06 CN CN201880058283.1A patent/CN111433211B/zh active Active
- 2018-07-06 AU AU2018297305A patent/AU2018297305B2/en active Active
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2022
- 2022-11-23 US US18/058,441 patent/US20230128195A1/en active Pending
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2023
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