JP2014503001A5 - - Google Patents
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- 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
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- 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 (https=) | 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 (https=) |
| EP (1) | EP2665716B1 (https=) |
| JP (2) | JP5993875B2 (https=) |
| CN (2) | CN106632401B (https=) |
| BR (1) | BR112013016241A2 (https=) |
| CA (1) | CA2814014A1 (https=) |
| ES (1) | ES2624288T3 (https=) |
| IL (1) | IL226405A0 (https=) |
| MX (1) | MX2013005115A (https=) |
| RU (1) | RU2013138226A (https=) |
| SG (2) | SG10201601516QA (https=) |
| WO (1) | WO2012100179A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2476431C2 (ru) | 2008-01-18 | 2013-02-27 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Конденсированное производное аминодигидротиазина |
| 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 |
| SG11201702632QA (en) * | 2014-10-10 | 2017-05-30 | Eisai R&D Man Co Ltd | Pharmaceutical composition of fused aminodihydrothiazine derivative |
| CN117244056A (zh) | 2016-10-27 | 2023-12-19 | 卫材研究发展管理有限公司 | 用于治疗阿尔茨海默病的含有抗Aβ初原纤维抗体和β-分泌酶BACE1抑制剂的组合物 |
| MX2021000778A (es) | 2018-07-24 | 2021-03-31 | Eisai R&D Man Co Ltd | Metodos de tratamiento y prevencion de la enfermedad de alzheimer. |
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 |
| CN1251671C (zh) | 2000-05-19 | 2006-04-19 | 武田药品工业株式会社 | β分泌酶抑制剂 |
| 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 |
| CA2505098A1 (en) | 2002-11-12 | 2004-05-27 | Merck & Co., Inc. | Phenylcarboxamide beta-secretase inhibitors for the treatment of alzheimer's disease |
| PT1699455E (pt) | 2003-12-15 | 2013-08-27 | Merck Sharp & Dohme | Inibidores de protease de aspartilo heterocíclicos |
| JP2007530696A (ja) | 2004-03-30 | 2007-11-01 | メルク エンド カムパニー インコーポレーテッド | アスパラギン酸プロテアーゼ阻害剤として有用な２−アミノチアゾール化合物 |
| PE20060664A1 (es) | 2004-09-15 | 2006-08-04 | Novartis Ag | Amidas biciclicas como inhibidores de cinasa |
| EP1802587A4 (en) | 2004-10-15 | 2010-02-17 | Astrazeneca Ab | SUBSTITUTED AMINO BINDINGS AND THEIR APPLICATIONS |
| WO2006041405A1 (en) | 2004-10-15 | 2006-04-20 | Astrazeneca Ab | Substituted amino-pyrimidones and uses thereof |
| CA2594946A1 (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 |
| MX2007016180A (es) | 2005-06-14 | 2008-03-07 | Schering Corp | Inhibidores de aspartil proteasas. |
| US8211904B2 (en) | 2005-07-18 | 2012-07-03 | Merck, Sharp & Dohme Corp. | Spiropiperidine beta-secretase inhibitors for the treatment of alzheimer's disease |
| RU2416603C9 (ru) | 2005-10-25 | 2012-06-20 | Сионоги Энд Ко., Лтд. | Производные аминодигидротиазина |
| 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 |
| JP5117382B2 (ja) | 2006-05-31 | 2013-01-16 | 第一三共株式会社 | ７員環化合物の製造方法 |
| 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 |
| ES2419239T3 (es) | 2007-05-29 | 2013-08-20 | Santen Pharmaceutical Co., Ltd | Nuevo derivado de 1,2,3,4-tetrahidroquinoxalina que tiene como sustituyente un grupo fenilo con una estructura de éster de ácido sulfónico o una estructura de amida de ácido sulfónico introducida en el mismo y que tienen una actividad de unión al receptor de glucocorticoides |
| PE20091236A1 (es) | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| RU2476431C2 (ru) | 2008-01-18 | 2013-02-27 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Конденсированное производное аминодигидротиазина |
| 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 |
| EP2318416B1 (en) | 2008-07-28 | 2013-09-04 | Eisai R&D Management Co., Ltd. | Spiroaminodihydrothiazine derivatives |
| KR20110076965A (ko) | 2008-09-30 | 2011-07-06 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 신규한 축합 아미노 디하이드로티아진 유도체 |
| 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 |
| JP2013530238A (ja) | 2010-07-01 | 2013-07-25 | アムジエン・インコーポレーテツド | Ｐｉ３ｋ活性の阻害剤としての複素環化合物及びその使用 |
| GB201101140D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
-
2012
- 2012-01-20 US US13/355,030 patent/US8426584B2/en not_active Expired - Fee Related
- 2012-01-20 SG SG10201601516QA patent/SG10201601516QA/en unknown
- 2012-01-20 BR BR112013016241A patent/BR112013016241A2/pt not_active IP Right Cessation
- 2012-01-20 ES ES12702690.4T patent/ES2624288T3/es active Active
- 2012-01-20 JP JP2013550622A patent/JP5993875B2/ja not_active Expired - Fee Related
- 2012-01-20 WO PCT/US2012/022053 patent/WO2012100179A1/en not_active Ceased
- 2012-01-20 EP EP12702690.4A patent/EP2665716B1/en active Active
- 2012-01-20 RU RU2013138226/04A patent/RU2013138226A/ru not_active Application Discontinuation
- 2012-01-20 CN CN201610875412.9A patent/CN106632401B/zh not_active Expired - Fee Related
- 2012-01-20 CN CN201280004193.7A patent/CN103502231A/zh active Pending
- 2012-01-20 MX MX2013005115A patent/MX2013005115A/es active IP Right Grant
- 2012-01-20 CA CA2814014A patent/CA2814014A1/en not_active Abandoned
- 2012-01-20 SG SG2013027461A patent/SG191710A1/en unknown
-
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
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