ES2653421T3 - Compuestos de tetrahidropirrolotiazina - Google Patents
Compuestos de tetrahidropirrolotiazina Download PDFInfo
- Publication number
- ES2653421T3 ES2653421T3 ES14712875.5T ES14712875T ES2653421T3 ES 2653421 T3 ES2653421 T3 ES 2653421T3 ES 14712875 T ES14712875 T ES 14712875T ES 2653421 T3 ES2653421 T3 ES 2653421T3
- Authority
- ES
- Spain
- Prior art keywords
- dichloromethane
- thiazin
- tetrahydropyrrolo
- benzamido
- mmol
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Abstract
Un compuesto de fórmula:**Fórmula** en la que R es H o F; y A es: o una sal farmacéuticamente aceptable del mismo.
Description
N-[3-[(4aR,7aS)-2-benzamido-4a,5,6,7-tetrahidro-4H-pirrolo[3,4-d][1,3]tiazin-7a-il]fenil]-5-fluoro-piridin-2-arboxamida; ácido 2,2,2-trifluoroacético
10
Se disuelve (4aR,7aS)-2-benzamido-7a-[3-[(5-fluoropiridin-2-carbonil)amino]fenil]-4,4a,5,7-tetrahidropirrolo[3,4-d] [1,3]tiazin-6-carboxilato de tert-butilo (105 mg, 0,18 mmol) se disuelve en diclorometano (2 ml) y se trata con ácido trifluoroacético (500 µl, 6,6 mmol). La solución de color amarillo resultante se agita durante 4 horas a temperatura ambiente y el disolvente se elimina en vacío para dar el producto del título en bruto (190 mg, 100%). ES/MS (m/e):
Preparación 25
N-[(4aR,7aS)-7a-(3-aminofenil)-4a,5,6,7-tetrahidro-4H-pirrolo[3,4-d][1,3]tiazin-2-il]benzamida
Se añade ácido trifluoroacético (25 ml) a una solución de (4aR,7aS)-7a-(3-aminofenil)-2-benzamido-4,4a,5,7tetrahidropirrolo[3,4-d][1,3]tiazin-6-carboxilato de tert-butilo (4 g, 8,84 mmol) en diclorometano (100 ml) y la mezcla
25 se agita a temperatura ambiente bajo nitrógeno durante 4 horas. El disolvente se elimina en vacío y el producto bruto se purifica con una columna SCX usando 3:1 de diclorometano:metanol y a continuación 2:1 de diclorometano:amoniaco 7 N en metanol para dar el compuesto del título (2,49 g, 80%). ES/MS (m/e): 353 (M+H).
Preparación 26
N-[7a-(5-amino-2-fluoro-fenil)-4a,5,6,7-tetrahidro-4H-pirrolo[3,4-d][1,3]tiazin-2-il]benzamida
30
35 Se añade ácido trifluoroacético (10 ml) a una solución de 7a-(5-amino-2-fluoro-fenil)-2-benzamido-4,4a,5,7tetrahidropirrolo[3,4-d][1,3]tiazin-6-carboxilato de tert-butilo (2,013 g, 4,28 mmol) en diclorometano (30 ml) y la mezcla se agita a temperatura ambiente bajo nitrógeno durante 4 horas. El disolvente se elimina en vacío y el producto bruto se purifica con una columna SCX usando 3:1 de diclorometano:metanol y a continuación 2:1 de diclorometano:amoniaco 7 N en metanol para dar el compuesto del título (1,555 g, 98%). ES/MS (m/e): 371 (M+H).
40 Preparación 27
N-[(4aR,7aS)-7a-(3-aminofenil)-6-(5-fluoropirimidin-2-il)-4,4a,5,7-tetrahidropirrolo[3,4-d][1,3]tiazin-2-il]benzamida
16
Claims (1)
-
imagen1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361776819P | 2013-03-12 | 2013-03-12 | |
| US201361776819P | 2013-03-12 | ||
| PCT/US2014/020070 WO2014143579A1 (en) | 2013-03-12 | 2014-03-04 | Tetrahydropyrrolothiazine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2653421T3 true ES2653421T3 (es) | 2018-02-07 |
Family
ID=50382615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14712875.5T Active ES2653421T3 (es) | 2013-03-12 | 2014-03-04 | Compuestos de tetrahidropirrolotiazina |
Country Status (38)
| Country | Link |
|---|---|
| US (3) | US8841293B1 (es) |
| EP (1) | EP2970336B1 (es) |
| JP (1) | JP6095844B2 (es) |
| KR (1) | KR101688761B1 (es) |
| CN (1) | CN105026404B (es) |
| AP (1) | AP2015008713A0 (es) |
| AR (1) | AR094918A1 (es) |
| BR (1) | BR112015018738A8 (es) |
| CA (1) | CA2898500C (es) |
| CL (1) | CL2015002529A1 (es) |
| CR (1) | CR20150418A (es) |
| CY (1) | CY1119585T1 (es) |
| DK (1) | DK2970336T3 (es) |
| EA (1) | EA026006B1 (es) |
| ES (1) | ES2653421T3 (es) |
| HK (1) | HK1212694A1 (es) |
| HR (1) | HRP20171851T1 (es) |
| HU (1) | HUE037487T2 (es) |
| IL (1) | IL240903B (es) |
| JO (1) | JO3317B1 (es) |
| LT (1) | LT2970336T (es) |
| MA (1) | MA38390B1 (es) |
| ME (1) | ME02910B (es) |
| MX (1) | MX2015012628A (es) |
| MY (1) | MY180083A (es) |
| NO (1) | NO3039297T3 (es) |
| NZ (1) | NZ712207A (es) |
| PE (1) | PE20151542A1 (es) |
| PH (1) | PH12015502031A1 (es) |
| PL (1) | PL2970336T3 (es) |
| PT (1) | PT2970336T (es) |
| RS (1) | RS56645B1 (es) |
| SG (1) | SG11201507499XA (es) |
| SI (1) | SI2970336T1 (es) |
| TN (1) | TN2015000340A1 (es) |
| TW (1) | TWI593692B (es) |
| UA (1) | UA112941C2 (es) |
| WO (1) | WO2014143579A1 (es) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA37756B1 (fr) | 2012-06-13 | 2018-09-28 | Hoffmann La Roche | Nouveaux composés diazaspirocycloalcane et azaspirocycloalcane |
| EP3590940B1 (en) | 2012-09-25 | 2021-06-09 | F. Hoffmann-La Roche AG | Hexahydropyrrolo[3,4-c]pyrrole derivatives and related compounds as autotaxin (atx) inhibitors and as inhibitors of the lysophosphatidic acid (lpa) production for treating e.g. renal diseases |
| EP2912041B1 (en) | 2012-10-26 | 2016-12-14 | Eli Lilly and Company | Tetrahydropyrrolothiazine derivatives as bace inhibitors |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
| MA38982A1 (fr) | 2013-11-26 | 2017-09-29 | Hoffmann La Roche | Nouvel octahydro-cyclobuta [1,2-c; 3,4-c'] dipyrrol-2-yl |
| TWI684452B (zh) | 2014-03-14 | 2020-02-11 | 美國禮來大藥廠 | 胺基噻嗪化合物 |
| MX2016010675A (es) | 2014-03-26 | 2016-11-10 | Hoffmann La Roche | Compuestos condensados de [1,4]diazepina como inhibidores de produccion de la autotaxina (atx) y acido lisofosfatidico (lpa). |
| CN106103446B (zh) | 2014-03-26 | 2019-07-30 | 豪夫迈·罗氏有限公司 | 作为自分泌运动因子(atx)和溶血磷脂酸(lpa)生产抑制剂的二环化合物 |
| TWI570127B (zh) * | 2014-09-15 | 2017-02-11 | 美國禮來大藥廠 | 結晶型N-[3-[(4aR,7aS)-2-胺基-6-(5-氟嘧啶-2-基)-4,4a,5,7-四氫吡咯并[3,4-d][1,3]噻嗪-7a-基]-4-氟-苯基]-5-甲氧基-吡嗪-2-甲醯胺、其用途及醫藥組合物 |
| TWI599358B (zh) * | 2014-09-16 | 2017-09-21 | 美國禮來大藥廠 | 組合療法 |
| TWI574969B (zh) * | 2015-01-30 | 2017-03-21 | 美國禮來大藥廠 | 甲苯磺酸鹽 |
| AR103680A1 (es) | 2015-02-23 | 2017-05-24 | Lilly Co Eli | Inhibidores selectivos de bace1 |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| AR104241A1 (es) | 2015-04-29 | 2017-07-05 | Lilly Co Eli | Derivados de tetrahidrofuro tiazina como inhibidores de bace1 selectivos |
| CN108026077B (zh) | 2015-09-04 | 2021-11-05 | 豪夫迈·罗氏有限公司 | 苯氧基甲基衍生物 |
| MA42923A (fr) | 2015-09-24 | 2021-04-28 | Hoffmann La Roche | Composés bicycliques comme inhibiteurs mixtes de atx/ca |
| MA42918A (fr) | 2015-09-24 | 2018-08-01 | Hoffmann La Roche | Composés bicycliques utilisés en tant qu'inhibiteurs d'atx |
| WO2017050792A1 (en) | 2015-09-24 | 2017-03-30 | F. Hoffmann-La Roche Ag | Bicyclic compounds as atx inhibitors |
| JP6845230B2 (ja) | 2015-09-24 | 2021-03-17 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | デュアルａｔｘ／ｃａ阻害剤としての新規な二環式化合物 |
| TW201740954A (zh) | 2016-03-16 | 2017-12-01 | 美國禮來大藥廠 | 組合療法 |
| TWI735600B (zh) | 2016-07-01 | 2021-08-11 | 美商美國禮來大藥廠 | 抗－N3pGlu類澱粉β肽抗體及其用途 |
| EP3555086B1 (en) | 2016-12-15 | 2021-09-01 | Amgen Inc. | 1,4-thiazine dioxide and 1,2,4-thiadiazine dioxide derivatives as beta-secretase inhibitors and methods of use |
| JP7149272B2 (ja) | 2016-12-15 | 2022-10-06 | アムジエン・インコーポレーテツド | β－セクレターゼ阻害剤としてのチアジン誘導体および使用方法 |
| CA3047287A1 (en) | 2016-12-15 | 2018-06-21 | Amgen Inc. | Cyclopropyl fused thiazine derivatives as beta-secretase inhibitors and methods of use |
| ES2910367T3 (es) * | 2016-12-15 | 2022-05-12 | Amgen Inc | Derivados de tiazina y oxazina bicíclicos como inhibidores de beta-secretasa y métodos de uso |
| MX2019007101A (es) | 2016-12-15 | 2019-12-16 | Amgen Inc | Derivados de oxazina como inhibidores de beta secretasa y metodos de uso. |
| MA49879A (fr) | 2017-03-16 | 2020-06-24 | Hoffmann La Roche | Composés hétérocycliques utiles en tant qu'inhibiteurs doubles d'atx/ca |
| CN110382484B (zh) | 2017-03-16 | 2022-12-06 | 豪夫迈·罗氏有限公司 | 新的作为atx抑制剂的二环化合物 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5284957A (en) * | 1992-09-03 | 1994-02-08 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
| WO2003082856A1 (en) * | 2002-03-22 | 2003-10-09 | Eli Lilly And Company | Isoquinoline-3-carboxylic acid derivatives as excitatory amino acid receptor antagonists |
| TWI332005B (en) | 2005-06-14 | 2010-10-21 | Schering Corp | Aspartyl protease inhibitors |
| ES2537898T3 (es) | 2005-10-25 | 2015-06-15 | Shionogi & Co., Ltd. | Derivados de aminotiazolidina y aminotetrahidrotiazepina como inhibidores de BACE 1 |
| JP5383483B2 (ja) | 2007-04-24 | 2014-01-08 | 塩野義製薬株式会社 | アルツハイマー症治療用医薬組成物 |
| CA2711655C (en) | 2008-01-18 | 2013-03-05 | Eisai R&D Management Co., Ltd. | Condensed aminodihydrothiazine derivative |
| AU2009239535A1 (en) * | 2008-04-22 | 2009-10-29 | Schering Corporation | Thiophenyl-substituted 2-imino-3-methyl pyrrolo pyrimidinone compounds as BACE-1 inhibitors, compositions, and their use |
| TWI431004B (zh) * | 2008-05-02 | 2014-03-21 | Lilly Co Eli | Ｂａｃｅ抑制劑 |
| US8637504B2 (en) | 2008-06-13 | 2014-01-28 | Shionogi & Co., Ltd. | Sulfur-containing heterocyclic derivative having beta secretase inhibitory activity |
| 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 |
| US20120245155A1 (en) | 2009-12-11 | 2012-09-27 | Shionogi & Co., Ltd. | Fused heterocyclic compound having amino group |
| GB201100181D0 (en) | 2011-01-06 | 2011-02-23 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101139D0 (en) | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| GB201101140D0 (en) * | 2011-01-21 | 2011-03-09 | Eisai Ltd | Fused aminodihydrothiazine derivatives |
| WO2012138590A1 (en) | 2011-04-07 | 2012-10-11 | Merck Sharp & Dohme Corp. | Pyrrolidine-fused thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| US8598161B2 (en) | 2011-05-24 | 2013-12-03 | Bristol-Myers Squibb Company | Compounds for the reduction of beta-amyloid production |
| JO3143B1 (ar) * | 2012-04-03 | 2017-09-20 | Lilly Co Eli | مركبات تتراهيدرو بيرولو ثيازين |
-
2014
- 2014-02-26 TW TW103106569A patent/TWI593692B/zh not_active IP Right Cessation
- 2014-02-27 AR ARP140100629A patent/AR094918A1/es unknown
- 2014-02-27 JO JOP/2014/0061A patent/JO3317B1/ar active
- 2014-03-04 RS RS20171243A patent/RS56645B1/sr unknown
- 2014-03-04 ME MEP-2017-252A patent/ME02910B/me unknown
- 2014-03-04 MY MYPI2015703056A patent/MY180083A/en unknown
- 2014-03-04 MA MA38390A patent/MA38390B1/fr unknown
- 2014-03-04 US US14/195,897 patent/US8841293B1/en active Active
- 2014-03-04 MX MX2015012628A patent/MX2015012628A/es unknown
- 2014-03-04 AP AP2015008713A patent/AP2015008713A0/xx unknown
- 2014-03-04 PL PL14712875T patent/PL2970336T3/pl unknown
- 2014-03-04 LT LTEP14712875.5T patent/LT2970336T/lt unknown
- 2014-03-04 BR BR112015018738A patent/BR112015018738A8/pt not_active Application Discontinuation
- 2014-03-04 JP JP2016500566A patent/JP6095844B2/ja active Active
- 2014-03-04 NZ NZ71220714A patent/NZ712207A/en not_active IP Right Cessation
- 2014-03-04 CA CA2898500A patent/CA2898500C/en not_active Expired - Fee Related
- 2014-03-04 KR KR1020157024588A patent/KR101688761B1/ko active IP Right Grant
- 2014-03-04 EA EA201591491A patent/EA026006B1/ru not_active IP Right Cessation
- 2014-03-04 HU HUE14712875A patent/HUE037487T2/hu unknown
- 2014-03-04 PE PE2015001901A patent/PE20151542A1/es active IP Right Grant
- 2014-03-04 PT PT147128755T patent/PT2970336T/pt unknown
- 2014-03-04 EP EP14712875.5A patent/EP2970336B1/en active Active
- 2014-03-04 DK DK14712875.5T patent/DK2970336T3/da active
- 2014-03-04 ES ES14712875.5T patent/ES2653421T3/es active Active
- 2014-03-04 CN CN201480014295.6A patent/CN105026404B/zh active Active
- 2014-03-04 SI SI201430430T patent/SI2970336T1/sl unknown
- 2014-03-04 WO PCT/US2014/020070 patent/WO2014143579A1/en active Application Filing
- 2014-03-04 SG SG11201507499XA patent/SG11201507499XA/en unknown
- 2014-04-03 UA UAA201508698A patent/UA112941C2/uk unknown
- 2014-08-07 US US14/453,855 patent/US8987254B2/en active Active
- 2014-08-12 NO NO14799063A patent/NO3039297T3/no unknown
-
2015
- 2015-02-19 US US14/626,320 patent/US20150157641A1/en not_active Abandoned
- 2015-08-10 TN TN2015000340A patent/TN2015000340A1/en unknown
- 2015-08-14 CR CR20150418A patent/CR20150418A/es unknown
- 2015-08-27 IL IL240903A patent/IL240903B/en not_active IP Right Cessation
- 2015-09-09 CL CL2015002529A patent/CL2015002529A1/es unknown
- 2015-09-10 PH PH12015502031A patent/PH12015502031A1/en unknown
-
2016
- 2016-01-21 HK HK16100629.1A patent/HK1212694A1/zh not_active IP Right Cessation
-
2017
- 2017-11-09 CY CY20171101177T patent/CY1119585T1/el unknown
- 2017-11-28 HR HRP20171851TT patent/HRP20171851T1/hr unknown
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