JP2014503001A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014503001A5 JP2014503001A5 JP2013550622A JP2013550622A JP2014503001A5 JP 2014503001 A5 JP2014503001 A5 JP 2014503001A5 JP 2013550622 A JP2013550622 A JP 2013550622A JP 2013550622 A JP2013550622 A JP 2013550622A JP 2014503001 A5 JP2014503001 A5 JP 2014503001A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- mixture
- salt
- alkyl
- 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 38
- 238000000034 method Methods 0.000 claims 24
- 239000000203 mixture Substances 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000001475 halogen functional group Chemical group 0.000 claims 12
- 239000002904 solvent Substances 0.000 claims 11
- 238000010438 heat treatment Methods 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 5
- 239000011874 heated mixture Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000011701 zinc Substances 0.000 claims 4
- 229910052725 zinc Inorganic materials 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- -1 carboxylic acid compound Chemical class 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 235000019439 ethyl acetate Nutrition 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 claims 1
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims 1
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 claims 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 claims 1
- 239000012256 powdered iron Substances 0.000 claims 1
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 claims 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161434849P | 2011-01-21 | 2011-01-21 | |
| US61/434,849 | 2011-01-21 | ||
| PCT/US2012/022053 WO2012100179A1 (en) | 2011-01-21 | 2012-01-20 | Methods and compounds useful in the synthesis of fused aminodihydrothiazine derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016041508A Division JP6087005B2 (ja) | 2011-01-21 | 2016-03-03 | 縮合アミノジヒドロチアジン誘導体の合成に有用な方法および化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014503001A JP2014503001A (ja) | 2014-02-06 |
| JP2014503001A5 true JP2014503001A5 (enExample) | 2016-01-28 |
| JP5993875B2 JP5993875B2 (ja) | 2016-09-14 |
Family
ID=45563570
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013550622A Expired - Fee Related JP5993875B2 (ja) | 2011-01-21 | 2012-01-20 | 縮合アミノジヒドロチアジン誘導体の合成に有用な方法および化合物 |
| JP2016041508A Expired - Fee Related JP6087005B2 (ja) | 2011-01-21 | 2016-03-03 | 縮合アミノジヒドロチアジン誘導体の合成に有用な方法および化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016041508A Expired - Fee Related JP6087005B2 (ja) | 2011-01-21 | 2016-03-03 | 縮合アミノジヒドロチアジン誘導体の合成に有用な方法および化合物 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US8426584B2 (enExample) |
| EP (1) | EP2665716B1 (enExample) |
| JP (2) | JP5993875B2 (enExample) |
| CN (2) | CN106632401B (enExample) |
| BR (1) | BR112013016241A2 (enExample) |
| CA (1) | CA2814014A1 (enExample) |
| ES (1) | ES2624288T3 (enExample) |
| IL (1) | IL226405A0 (enExample) |
| MX (1) | MX2013005115A (enExample) |
| RU (1) | RU2013138226A (enExample) |
| SG (2) | SG191710A1 (enExample) |
| WO (1) | WO2012100179A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100317850A1 (en) | 2008-01-18 | 2010-12-16 | Yuichi Suzuki | Condensed aminodihydrothiazine derivative |
| GB0912777D0 (en) | 2009-07-22 | 2009-08-26 | Eisai London Res Lab Ltd | Fused aminodihydropyrimidone derivatives |
| GB0912778D0 (en) | 2009-07-22 | 2009-08-26 | Eisai London Res Lab Ltd | Fused aminodihydro-oxazine derivatives |
| GB201100181D0 (en) | 2011-01-06 | 2011-02-23 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101140D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101139D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| UY34278A (es) | 2011-08-25 | 2013-04-05 | Novartis Ag | Derivados novedosos de oxazina y su uso en el tratamiento de enfermedades |
| GB201212816D0 (en) * | 2012-07-19 | 2012-09-05 | Eisai Ltd | Novel compounds |
| JO3318B1 (ar) | 2013-06-18 | 2019-03-13 | Lilly Co Eli | مثبطات bace |
| CN107106568B (zh) * | 2014-10-10 | 2023-09-26 | 卫材R&D管理有限公司 | 稠合氨基二氢噻嗪衍生物的药物组合物 |
| AU2017347838B2 (en) | 2016-10-27 | 2023-04-27 | Eisai R&D Management Co., Ltd. | Composition comprising an anti-Αβ protofibril antibody and a beta-secretase BACE1 inhibitor for the treatment of Alzheimer's disease |
| IL280315B2 (en) | 2018-07-24 | 2024-06-01 | Eisai R&D Man Co Ltd | Methods for treating and preventing Alzheimer's disease |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3227713A (en) | 1966-01-04 | Azine derivatives | ||
| US3235551A (en) | 1966-02-15 | Novel derivatives of | ||
| JPH0967355A (ja) | 1995-08-31 | 1997-03-11 | Tokyo Tanabe Co Ltd | チアジン誘導体、チアゾール誘導体及びそれらの製造方法 |
| AU2001258771A1 (en) | 2000-05-19 | 2001-11-26 | Takeda Chemical Industries Ltd. | -secretase inhibitors |
| US6562783B2 (en) | 2001-05-30 | 2003-05-13 | Neurologic, Inc. | Phosphinylmethyl and phosphorylmethyl succinic and glutauric acid analogs as β-secretase inhibitors |
| WO2004014843A1 (ja) | 2002-08-09 | 2004-02-19 | Takeda Chemical Industries, Ltd. | 置換アミノ化合物およびその用途 |
| WO2004037212A2 (en) | 2002-10-24 | 2004-05-06 | Sepracor, Inc. | Compositions comprising zopiclone derivatives and methods of making and using the same |
| JP2004149429A (ja) | 2002-10-29 | 2004-05-27 | Takeda Chem Ind Ltd | インドール化合物およびその用途 |
| ATE443043T1 (de) | 2002-11-12 | 2009-10-15 | Merck & Co Inc | Phenylcarboxamide als beta-sekretase-hemmer zur behandlung von alzheimer |
| EP2153832B1 (en) | 2003-12-15 | 2016-03-09 | Merck Sharp & Dohme Corp. | Heterocyclic aspartyl protease inhibitors |
| WO2005097767A1 (en) | 2004-03-30 | 2005-10-20 | Merck & Co., Inc. | 2-aminothiazole compounds useful as aspartyl protease inhibitors |
| PE20060664A1 (es) | 2004-09-15 | 2006-08-04 | Novartis Ag | Amidas biciclicas como inhibidores de cinasa |
| WO2006041405A1 (en) | 2004-10-15 | 2006-04-20 | Astrazeneca Ab | Substituted amino-pyrimidones and uses thereof |
| CN101084199A (zh) | 2004-10-15 | 2007-12-05 | 阿斯利康(瑞典)有限公司 | 取代的氨基化合物及其用途 |
| WO2006078577A1 (en) | 2005-01-19 | 2006-07-27 | Merck & Co., Inc. | Tertiary carbinamines having substituted heterocycles, which are active as inhibitors of beta-secretase, for the treatment of alzheimer's disease |
| PE20070135A1 (es) | 2005-06-14 | 2007-03-09 | Schering Corp | Compuestos heterociclicos como inhibidores de aspartil proteasas |
| ATE550338T1 (de) | 2005-07-18 | 2012-04-15 | Merck Sharp & Dohme | Spiropiperidininhibitoren von beta-secretase zur behandlung von alzheimer-krankheit |
| KR101052122B1 (ko) | 2005-10-25 | 2011-07-26 | 시오노기세야쿠 가부시키가이샤 | 아미노디히드로티아진 유도체 |
| US20090099217A1 (en) | 2006-04-05 | 2009-04-16 | Astex Therapeutics Ltd. | 2-Aminopyrimidin-4-Ones And Their Use For Treating Or Preventing Alpha Beta-Related Pathologies |
| MX2008015196A (es) | 2006-05-31 | 2008-12-15 | Asubio Pharma Co Ltd | Compuesto de anillo de 7 miembros, proceso para producir el mismo, y su uso medico. |
| AU2007332754A1 (en) | 2006-12-12 | 2008-06-19 | Schering Corporation | Aspartyl protease inhibitors |
| EP2147914B1 (en) | 2007-04-24 | 2014-06-04 | Shionogi&Co., Ltd. | Aminodihydrothiazine derivatives substituted with cyclic groups |
| EP2151435A4 (en) | 2007-04-24 | 2011-09-14 | Shionogi & Co | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| WO2008146871A1 (ja) | 2007-05-29 | 2008-12-04 | Santen Pharmaceutical Co., Ltd. | グルココルチコイド受容体結合活性を有する、スルホン酸エステル又はスルホン酸アミド構造を導入したフェニル基を置換基として有する新規１，２，３，４－テトラヒドロキノキサリン誘導体 |
| PE20091236A1 (es) | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| US20100317850A1 (en) * | 2008-01-18 | 2010-12-16 | Yuichi Suzuki | Condensed aminodihydrothiazine derivative |
| TWI431004B (zh) | 2008-05-02 | 2014-03-21 | Lilly Co Eli | Ｂａｃｅ抑制劑 |
| WO2010013302A1 (ja) | 2008-07-28 | 2010-02-04 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | スピロアミノジヒドロチアジン誘導体 |
| AU2009277485B2 (en) | 2008-07-28 | 2013-05-02 | Eisai R&D Management Co., Ltd. | Spiroaminodihydrothiazine derivatives |
| JP5666304B2 (ja) | 2008-09-30 | 2015-02-12 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 新規な縮合アミノジヒドロチアジン誘導体 |
| AR077277A1 (es) * | 2009-07-09 | 2011-08-17 | Lilly Co Eli | Compuestos de biciclo (1,3)tiazin-2-amina formulacion farmaceutica que lo comprende y su uso para la manufactura de un medicamento util para el tratamiento de la enfermedad de alzheimer |
| GB0912778D0 (en) | 2009-07-22 | 2009-08-26 | Eisai London Res Lab Ltd | Fused aminodihydro-oxazine derivatives |
| GB0912777D0 (en) | 2009-07-22 | 2009-08-26 | Eisai London Res Lab Ltd | Fused aminodihydropyrimidone derivatives |
| WO2012003274A1 (en) | 2010-07-01 | 2012-01-05 | Amgen Inc. | Heterocyclic compounds and their use as inhibitors of pi3k activity |
| GB201101140D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
-
2012
- 2012-01-20 SG SG2013027461A patent/SG191710A1/en unknown
- 2012-01-20 EP EP12702690.4A patent/EP2665716B1/en active Active
- 2012-01-20 MX MX2013005115A patent/MX2013005115A/es active IP Right Grant
- 2012-01-20 BR BR112013016241A patent/BR112013016241A2/pt not_active IP Right Cessation
- 2012-01-20 JP JP2013550622A patent/JP5993875B2/ja not_active Expired - Fee Related
- 2012-01-20 CA CA2814014A patent/CA2814014A1/en not_active Abandoned
- 2012-01-20 RU RU2013138226/04A patent/RU2013138226A/ru not_active Application Discontinuation
- 2012-01-20 ES ES12702690.4T patent/ES2624288T3/es active Active
- 2012-01-20 SG SG10201601516QA patent/SG10201601516QA/en unknown
- 2012-01-20 CN CN201610875412.9A patent/CN106632401B/zh active Active
- 2012-01-20 WO PCT/US2012/022053 patent/WO2012100179A1/en not_active Ceased
- 2012-01-20 US US13/355,030 patent/US8426584B2/en not_active Expired - Fee Related
- 2012-01-20 CN CN201280004193.7A patent/CN103502231A/zh active Pending
-
2013
- 2013-03-12 US US13/795,308 patent/US8802871B2/en active Active
- 2013-05-16 IL IL226405A patent/IL226405A0/en unknown
-
2014
- 2014-06-26 US US14/316,321 patent/US8962858B2/en not_active Expired - Fee Related
-
2016
- 2016-03-03 JP JP2016041508A patent/JP6087005B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014503001A5 (enExample) | ||
| JP2016121177A5 (enExample) | ||
| RU2013138226A (ru) | Способы и соединения, пригодные для получения конденсированных аминодигидротиазиновых производных | |
| JP6050358B2 (ja) | ベンゾオキサジノンをアミンと反応させることによるテトラゾール置換アントラニル酸ジアミド誘導体の製造方法 | |
| JP2017522357A5 (enExample) | ||
| JP2016507504A5 (enExample) | ||
| JP2013508368A5 (enExample) | ||
| CN103214455B (zh) | 一种比拉斯汀的制备方法 | |
| JP2014511387A5 (enExample) | ||
| WO2018032586A1 (zh) | 一种3-(二氟甲基)-1-甲基-1h-吡唑-4-羧酸的合成方法及其中间体 | |
| CN105418502B (zh) | 一种用于合成帕罗西汀的中间体及其制备方法和用途 | |
| JP2014031512A5 (enExample) | ||
| JP6251197B2 (ja) | 置換フェニルプロパノンを調製するためのプロセス | |
| JP7027541B2 (ja) | ジシクロヘキサンジカルボン酸ジエステルの製造方法およびジシクロヘキサンジカルボン酸の製造方法 | |
| CN108689874B (zh) | 一种制备2-芳基丙二酰胺的方法及其应用 | |
| JP2011513358A5 (enExample) | ||
| JPWO2017056501A1 (ja) | 酸ハライド溶液の製造方法、混合溶液、及びモノエステル化合物の製造方法 | |
| CN109422675B (zh) | 一种新型单胺氧化酶抑制剂吗拉贝胺的合成方法 | |
| WO2014103812A1 (ja) | ピラゾール化合物の結晶の製造方法 | |
| CN103421037B (zh) | 1-乙氧羰基-5-甲基-(3r)-叔丁基二甲硅氧基戊二酸酯的合成工艺 | |
| JP2013136561A (ja) | ２，６−ジエチル−４−メチルフェニル酢酸の製造方法 | |
| CN1330636C (zh) | 盐酸替罗非班中间体的合成方法 | |
| WO2003014067A1 (fr) | Methode de production d'un compose beta-oxonitrile ou d'un sel de metal alcalin dudit compose | |
| CN102643273B (zh) | 一种伊潘立酮的制备方法 | |
| CN110437093A (zh) | 一种(s)-5-氟-3-甲基异苯并呋喃-3-酮的乙酰化中间体的制备方法 |