JP2010540658A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010540658A5 JP2010540658A5 JP2010528165A JP2010528165A JP2010540658A5 JP 2010540658 A5 JP2010540658 A5 JP 2010540658A5 JP 2010528165 A JP2010528165 A JP 2010528165A JP 2010528165 A JP2010528165 A JP 2010528165A JP 2010540658 A5 JP2010540658 A5 JP 2010540658A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- alkyl
- formula
- protecting group
- group
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 67
- 238000000034 method Methods 0.000 claims 49
- 125000006239 protecting group Chemical group 0.000 claims 39
- 125000000217 alkyl group Chemical group 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- -1 triethylsilyl Chemical group 0.000 claims 13
- 239000000203 mixture Substances 0.000 claims 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 9
- 150000001241 acetals Chemical class 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 8
- 150000005676 cyclic carbonates Chemical class 0.000 claims 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims 6
- 150000004820 halides Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000005907 alkyl ester group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 4
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 4
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- DBASDGQROJIJMT-UHFFFAOYSA-N 2-benzylidenepyran Chemical compound O1C=CC=CC1=CC1=CC=CC=C1 DBASDGQROJIJMT-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 239000012296 anti-solvent Substances 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims 2
- PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 claims 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical group [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical compound [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99762507P | 2007-10-03 | 2007-10-03 | |
| US60/997,625 | 2007-10-03 | ||
| PCT/US2008/078762 WO2009046308A1 (en) | 2007-10-03 | 2008-10-03 | Intermediates and methods for the synthesis of halichondrin b analogs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010540658A JP2010540658A (ja) | 2010-12-24 |
| JP2010540658A5 true JP2010540658A5 (OSRAM) | 2011-12-15 |
| JP5735277B2 JP5735277B2 (ja) | 2015-06-17 |
Family
ID=40019255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010528165A Active JP5735277B2 (ja) | 2007-10-03 | 2008-10-03 | ハリコンドリンｂ類似体の合成のための中間体および方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (6) | US8093410B2 (OSRAM) |
| EP (2) | EP2578576B9 (OSRAM) |
| JP (1) | JP5735277B2 (OSRAM) |
| CN (3) | CN108948039B (OSRAM) |
| BR (1) | BRPI0817909B1 (OSRAM) |
| CA (1) | CA2701534C (OSRAM) |
| IL (1) | IL204791A (OSRAM) |
| MX (1) | MX2010003599A (OSRAM) |
| RU (1) | RU2489437C2 (OSRAM) |
| SG (1) | SG10201811715YA (OSRAM) |
| WO (1) | WO2009046308A1 (OSRAM) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2682878B2 (ja) | 1989-11-27 | 1997-11-26 | 上村工業株式会社 | シールド付き電気めっき装置 |
| DK1087960T3 (da) | 1998-06-17 | 2011-06-14 | Eisai R&D Man Co Ltd | Makrocykliske analoger og fremgangsmåder til deres anvendelse og fremstilling |
| US7982060B2 (en) | 2004-06-03 | 2011-07-19 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of analogs of Halichondrin B |
| WO2009046308A1 (en) | 2007-10-03 | 2009-04-09 | Eisai R & D Management Co., Ltd. | Intermediates and methods for the synthesis of halichondrin b analogs |
| SG189739A1 (en) | 2008-04-04 | 2013-05-31 | Eisai R&D Man Co Ltd | Halichondrin b analogs |
| DE102009012660A1 (de) * | 2009-03-13 | 2010-09-16 | H.C. Starck Clevios Gmbh | Polymerbeschichtungen mit verbesserter Temperaturstabilität |
| MY160203A (en) | 2009-03-30 | 2017-02-28 | Eisai R&D Man Co Ltd | Liposome composition |
| EP2528914B1 (en) | 2010-01-26 | 2014-06-11 | Eisai R&D Management Co., Ltd. | Furo[3,2-b]pyrane derivatives useful in the synthesis of halichondrin b analogs |
| CN102225921B (zh) * | 2011-04-26 | 2013-04-24 | 中国人民解放军第二军医大学 | 一种环戊烷聚酮类化合物simplextone A及其用途 |
| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| EP2928464A1 (en) | 2012-12-04 | 2015-10-14 | Eisai R&D Management Co., Ltd. | Use of eribulin in the treatment of breast cancer |
| KR102265952B1 (ko) | 2013-06-26 | 2021-06-16 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 암 치료 병용요법으로서 에리불린 및 렌바티닙의 용도 |
| JP6625533B2 (ja) | 2013-11-04 | 2019-12-25 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ハリコンドリンｂの類縁体の合成において有用な大環化反応および中間体 |
| CN105916861B (zh) | 2013-12-06 | 2018-12-14 | 卫材R&D管理有限公司 | 可用于合成软海绵素b类似物的方法 |
| SG11201609777SA (en) | 2014-05-28 | 2016-12-29 | Eisai R&D Man Co Ltd | Use of eribulin in the treatment of cancer |
| EP3160970A4 (en) | 2014-06-30 | 2017-12-27 | President and Fellows of Harvard College | Synthesis of halichondrin analogs and uses thereof |
| US10208058B2 (en) | 2014-09-09 | 2019-02-19 | Cipla Limited | Process for the preparation of macrocyclic ketone analogs of halichondrin B or pharmaceutically acceptable salts and intermediates thereof |
| CA2978226C (en) | 2015-03-04 | 2025-02-18 | Eisai R&D Management Co., Ltd. | COMBINATION OF A PD-1 ANTAGONIST AND A VEGFR/FGFR/RET TYROSINE KINASE INHIBITOR TO TREAT CANCER |
| EP3265122B1 (en) | 2015-03-04 | 2022-05-04 | Merck Sharp & Dohme Corp. | Combination of pembrolizumab and eribulin for treating triple-negative breast cancer |
| US10344038B2 (en) | 2015-04-30 | 2019-07-09 | President And Fellows Of Harvard College | Chromium-mediated coupling and application to the synthesis of halichondrins |
| RU2739034C2 (ru) | 2015-05-07 | 2020-12-21 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Реакции макроциклизации и промежуточное соединение и другие фрагменты, полезные в синтезе макролидов галихондринов |
| CN108601760A (zh) | 2016-02-12 | 2018-09-28 | 卫材R&D管理有限公司 | 艾日布林的合成中的中间体及相关的合成方法 |
| SMT202100416T1 (it) | 2016-03-02 | 2021-09-14 | Eisai R&D Man Co Ltd | Coniugati anticorpo-farmaco a base di eribulina e metodi di uso |
| JP7015237B2 (ja) | 2016-04-28 | 2022-02-02 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 腫瘍の成長を抑制する方法 |
| CN114805322B (zh) * | 2016-06-30 | 2025-05-30 | 卫材R&D管理有限公司 | 可用于合成软海绵素大环内酯类及其类似物的普林斯反应和中间体 |
| KR20190082782A (ko) | 2016-10-14 | 2019-07-10 | 머크 샤프 앤드 돔 코포레이션 | 요로상피암을 치료하기 위한 pd-1 길항제 및 에리불린의 조합 |
| 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 |
| KR102634732B1 (ko) | 2017-04-05 | 2024-02-13 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 마크로시클릭 화합물 및 그의 용도 |
| US9938288B1 (en) | 2017-04-05 | 2018-04-10 | President And Fellows Of Harvard College | Macrocyclic compound and uses thereof |
| EP4169924A3 (en) * | 2017-07-06 | 2023-07-05 | 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 |
| US20190046513A1 (en) | 2017-08-10 | 2019-02-14 | Huya Bioscience International, Llc | Combination therapies of hdac inhibitors and tubulin inhibitors |
| CN117924310A (zh) | 2017-11-15 | 2024-04-26 | 哈佛大学的校长及成员们 | 大环化合物及其用途 |
| US11419856B2 (en) | 2017-11-20 | 2022-08-23 | Basilea Pharmaceutica International AG | Pharmaceutical combinations for use in the treatment of neoplastic diseases |
| CN118894868A (zh) | 2018-01-03 | 2024-11-05 | 卫材R&D管理有限公司 | 可用于合成软海绵素大环内酯及其类似物的普林斯反应和化合物 |
| US11447499B2 (en) | 2019-06-14 | 2022-09-20 | Rk Pharma Inc. | Process for the preparation of eribulin mesylate intermediate |
| JP7574232B2 (ja) | 2019-06-21 | 2024-10-28 | カウンスィル オブ サイエンティフィック アンド インダストリアル リサーチ | ホモプロパルギルアルコールを調製するための化学酵素的プロセス |
| US12036204B2 (en) | 2019-07-26 | 2024-07-16 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition for treating tumor |
| US11083705B2 (en) | 2019-07-26 | 2021-08-10 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition for treating tumor |
| CN110981903A (zh) * | 2019-11-28 | 2020-04-10 | 南京正济医药研究有限公司 | 一种艾日布林中间体化合物提高光学纯度的精制方法 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2027890C3 (de) * | 1970-06-06 | 1979-02-01 | Kali Chemie Ag | 8-AIkoxy oder -Benzyloxy-3-methyl-lO- methylen-2,9-dioxatricyclo-(43,l,03,7 )-decan-4-one und 8-AIkoxy oder 8-Benzyloxy-3,10-dimethyl-2,9dioxatricyclo- (43,1,O" )-decan-4-one |
| SU652180A1 (ru) | 1975-12-16 | 1979-03-15 | Краснодарский политехнический институт | 1(Фурил-2,)-2-(2-,, формилфурил-5,, ) этилен или его метильное производное как промежуточный продукт дл синтеза фуран-2,5-дикарбоновой кислоты и способ его получени |
| US4086245A (en) * | 1976-12-09 | 1978-04-25 | The Upjohn Company | Antibiotics 7-O-alkylnogarols |
| SU722912A1 (ru) * | 1978-03-06 | 1980-03-25 | Уфимский Нефтяной Институт | Способ получени 5-метил/-4оксо3,6,8-триоксабицикло/ (3,2,1)-октана |
| 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 |
| TW255880B (OSRAM) | 1992-09-09 | 1995-09-01 | Hoechst Ag | |
| AU4255697A (en) | 1996-09-06 | 1998-03-26 | Eli Lilly And Company | Catalytic selective sulfonylation process |
| US6870058B2 (en) | 1996-12-03 | 2005-03-22 | The Trustees Of The University Of Pennsylvania | Compounds which mimic the chemical and biological properties of discodermolide |
| DK1087960T3 (da) * | 1998-06-17 | 2011-06-14 | Eisai R&D Man Co Ltd | Makrocykliske analoger og fremgangsmåder til deres anvendelse og fremstilling |
| US6653341B1 (en) * | 1998-06-17 | 2003-11-25 | Eisai Co., Ltd. | Methods and compositions for use in treating cancer |
| US8097648B2 (en) | 1998-06-17 | 2012-01-17 | Eisai R&D Management Co., Ltd. | Methods and compositions for use in treating cancer |
| DE10106647A1 (de) | 2001-02-12 | 2002-08-22 | Univ Hannover | Ratjadon-Derivate zum Hemmen des Zellwachstums |
| CA2822994C (en) * | 2004-06-03 | 2016-09-27 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of analogs of halichondrin b |
| US7982060B2 (en) | 2004-06-03 | 2011-07-19 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of analogs of Halichondrin B |
| US20060045846A1 (en) | 2004-08-30 | 2006-03-02 | Horstmann Thomas E | Reagents and methods for labeling terminal olefins |
| US20060154312A1 (en) | 2004-12-09 | 2006-07-13 | Sergei Agoulnik | Tubulin isotype screening in cancer therapy using halichondrin B analogs |
| US7915457B2 (en) | 2005-09-26 | 2011-03-29 | Symrise Gmbh & Co. Kg | Intramolecular Prins reaction and catalysts suitable therefor |
| WO2008010776A1 (en) | 2006-07-21 | 2008-01-24 | Agency For Science, Technology And Research | Aigialomycin d and derivatives thereof and their use in treating cancer or malaria or a microbial infection |
| US8119839B2 (en) | 2007-07-20 | 2012-02-21 | Yamada Apiculture Center, Inc. | Carboxylic acid and antidepressant composition containing the same as active ingredient |
| WO2009046308A1 (en) * | 2007-10-03 | 2009-04-09 | Eisai R & D Management Co., Ltd. | Intermediates and methods for the synthesis of halichondrin b analogs |
| BRPI0820519A2 (pt) * | 2007-11-16 | 2017-05-23 | Eisai R&D Man Co Ltd | intermediário para a síntese do análogo de halicondrina b e reação de dessulfonilação usada para o intermediário |
| SG189739A1 (en) | 2008-04-04 | 2013-05-31 | Eisai R&D Man Co Ltd | Halichondrin b analogs |
| JP5371091B2 (ja) | 2009-01-23 | 2013-12-18 | 三菱レイヨン株式会社 | モノスルホン酸エステルの製造方法 |
| EP2528914B1 (en) * | 2010-01-26 | 2014-06-11 | Eisai R&D Management Co., Ltd. | Furo[3,2-b]pyrane derivatives useful in the synthesis of halichondrin b analogs |
| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| US9181152B2 (en) | 2011-11-30 | 2015-11-10 | Alphora Research Inc. | Process for preparation of (3R)-2,4-di-leaving group-3-methylbut-1-ene |
| IN2014MN02106A (OSRAM) | 2012-03-30 | 2015-09-11 | Alphora Res Inc | |
| US9850254B2 (en) | 2013-07-03 | 2017-12-26 | Sandoz Ag | Synthetic process for preparation of macrocyclic C1-keto analogs of Halichondrin B and intermediates useful therein including intermediates containing-SO2-(p-tolyl) groups |
| JP6625533B2 (ja) | 2013-11-04 | 2019-12-25 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ハリコンドリンｂの類縁体の合成において有用な大環化反応および中間体 |
| CN105916861B (zh) | 2013-12-06 | 2018-12-14 | 卫材R&D管理有限公司 | 可用于合成软海绵素b类似物的方法 |
| US10208058B2 (en) | 2014-09-09 | 2019-02-19 | Cipla Limited | Process for the preparation of macrocyclic ketone analogs of halichondrin B or pharmaceutically acceptable salts and intermediates thereof |
| RU2739034C2 (ru) | 2015-05-07 | 2020-12-21 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Реакции макроциклизации и промежуточное соединение и другие фрагменты, полезные в синтезе макролидов галихондринов |
| CN108601760A (zh) | 2016-02-12 | 2018-09-28 | 卫材R&D管理有限公司 | 艾日布林的合成中的中间体及相关的合成方法 |
| CN114805322B (zh) | 2016-06-30 | 2025-05-30 | 卫材R&D管理有限公司 | 可用于合成软海绵素大环内酯类及其类似物的普林斯反应和中间体 |
| WO2018217894A1 (en) | 2017-05-24 | 2018-11-29 | Eisai R&D Management Co., Ltd. | Fluorine-labelled halichondrin derivatives and related methods of synthesis |
| CN118894868A (zh) | 2018-01-03 | 2024-11-05 | 卫材R&D管理有限公司 | 可用于合成软海绵素大环内酯及其类似物的普林斯反应和化合物 |
-
2008
- 2008-10-03 WO PCT/US2008/078762 patent/WO2009046308A1/en not_active Ceased
- 2008-10-03 CN CN201810736587.0A patent/CN108948039B/zh active Active
- 2008-10-03 CN CN201410421907.5A patent/CN104311571B/zh active Active
- 2008-10-03 US US12/245,149 patent/US8093410B2/en active Active
- 2008-10-03 SG SG10201811715YA patent/SG10201811715YA/en unknown
- 2008-10-03 BR BRPI0817909-3A patent/BRPI0817909B1/pt active IP Right Grant
- 2008-10-03 RU RU2010117520/04A patent/RU2489437C2/ru active
- 2008-10-03 JP JP2010528165A patent/JP5735277B2/ja active Active
- 2008-10-03 EP EP12191294.3A patent/EP2578576B9/en active Active
- 2008-10-03 EP EP08836425.2A patent/EP2200992B1/en active Active
- 2008-10-03 CA CA2701534A patent/CA2701534C/en active Active
- 2008-10-03 CN CN200880119686.9A patent/CN101883763B/zh active Active
- 2008-10-03 MX MX2010003599A patent/MX2010003599A/es unknown
-
2010
- 2010-03-28 IL IL204791A patent/IL204791A/en active IP Right Grant
-
2011
- 2011-12-22 US US13/334,516 patent/US8987479B2/en active Active
-
2015
- 2015-02-17 US US14/624,033 patent/US9604993B2/en active Active
-
2016
- 2016-04-07 US US15/092,850 patent/US9802953B2/en active Active
-
2017
- 2017-10-18 US US15/787,268 patent/US10214539B2/en active Active
-
2019
- 2019-02-25 US US16/284,405 patent/US10717743B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010540658A5 (OSRAM) | ||
| RU2489437C2 (ru) | Промежуточные соединения и способы синтеза аналогов галихондрина в | |
| JP2018172424A5 (OSRAM) | ||
| TWI640500B (zh) | 製備曲伏前列腺素之新穎方法 | |
| EP2521717A1 (en) | Method for the preparation of rivaroxaban | |
| CN1069028A (zh) | 红豆杉醇侧链的不对称合成 | |
| JP2011526896A5 (OSRAM) | ||
| JP2021503522A5 (OSRAM) | ||
| CN1589263A (zh) | 光学活性氧代庚烯酸酯的制备方法 | |
| JP6121492B2 (ja) | （１ｓ，４ｒ）−２−オキサ−３−アザビシクロ［２．２．１］ヘプト−５−エンの製造方法 | |
| AU2010275780A1 (en) | Preparation of (R)- and (S)-N-(3, 4-difluoro-2-(2-fluoro-4-iodophenylamino)--6-methoxyphenyl) -1- (2, 3-dihydroxypropyl)cyclopropane-1-sulfonamide and protected derivatives thereof | |
| JPH09263583A (ja) | Ｎ−ベンジルインドールの調製法 | |
| KR20220011502A (ko) | 신규한 이노토디올의 제조방법 | |
| JP2008508231A5 (OSRAM) | ||
| KR20070100717A (ko) | 앤지오텐신 ⅱ 수용기 길항제의 제조를 위한 중간화합물 | |
| KR101821685B1 (ko) | 베라프로스트 제조 중간체의 제조방법 | |
| JPWO2006088071A1 (ja) | 抗ｈｃｖ作用を有する化合物の製造方法およびその中間体 | |
| US7297807B1 (en) | Intermediates for the synthesis of polypropionate antibiotics | |
| CN101842363A (zh) | 制备(6r)-3-己基-4-羟基-6-十一烷基-5,6-二氢吡喃-2-酮的方法及该方法中所用的中间体 | |
| CN101842370B (zh) | 手性拆分2-取代的4-取代的1,3-氧硫杂环戊烷的方法 | |
| CN1436761A (zh) | 一种烷基环己基炔类液晶及其生产方法 | |
| JP3403761B2 (ja) | ３，５―ジヒドロキシ―１―オクテン―７―イン類及びその製造方法 | |
| JP2020503386A (ja) | エリブリンメシル酸塩の製造中間体及びその製造方法 | |
| EP2822927A1 (en) | PROCESS FOR PREPARATION OF PROSTAGLANDIN F2alpha ANALOGUES | |
| JP5300713B2 (ja) | ６−ヒドロキシエチルペナム化合物の製造方法 |