JP2014507414A5 - - Google Patents
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- Publication number
- JP2014507414A5 JP2014507414A5 JP2013549769A JP2013549769A JP2014507414A5 JP 2014507414 A5 JP2014507414 A5 JP 2014507414A5 JP 2013549769 A JP2013549769 A JP 2013549769A JP 2013549769 A JP2013549769 A JP 2013549769A JP 2014507414 A5 JP2014507414 A5 JP 2014507414A5
- Authority
- JP
- Japan
- Prior art keywords
- thiobutoxy
- thiophen
- benzo
- under reduced
- carbon atoms
- 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.)
- Pending
Links
- 125000005309 thioalkoxy group Chemical group 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- -1 1,2-dimethylthiobutoxy Chemical group 0.000 description 2
- SAAWNQLNUJBOLW-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)acetic acid Chemical compound C1=CC=C2SC(CC(=O)O)=CC2=C1 SAAWNQLNUJBOLW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SPJJYCYYBXUZCP-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)acetonitrile Chemical compound C1=CC=C2SC(CC#N)=CC2=C1 SPJJYCYYBXUZCP-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- DEAIGIYAVHOUEQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2-methylazetidine-2-carboxamide Chemical compound C=1C=C(Cl)C=CC=1CNC(=O)C1(C)CCN1 DEAIGIYAVHOUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- VKZSTQSXCSNCDH-UHFFFAOYSA-N tert-butyl 2-[(4-chlorophenyl)methylcarbamoyl]-2-methylazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC1(C)C(=O)NCC1=CC=C(Cl)C=C1 VKZSTQSXCSNCDH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161434077P | 2011-01-19 | 2011-01-19 | |
| US61/434,077 | 2011-01-19 | ||
| PCT/EP2012/050297 WO2012098033A1 (en) | 2011-01-19 | 2012-01-10 | Azetidine derivatives useful for the treatment of metabolic and inflammatory diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014507414A JP2014507414A (ja) | 2014-03-27 |
| JP2014507414A5 true JP2014507414A5 (https=) | 2015-03-12 |
Family
ID=45507689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013549769A Pending JP2014507414A (ja) | 2011-01-19 | 2012-01-10 | 代謝疾患及び炎症疾患の治療に有用なアゼチジン誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US8759334B2 (https=) |
| EP (1) | EP2665704A1 (https=) |
| JP (1) | JP2014507414A (https=) |
| KR (1) | KR20140040104A (https=) |
| CN (1) | CN103328442A (https=) |
| AR (1) | AR084857A1 (https=) |
| AU (1) | AU2012208693B2 (https=) |
| BR (1) | BR112013018286A2 (https=) |
| CA (1) | CA2824460A1 (https=) |
| CO (1) | CO6741223A2 (https=) |
| GB (1) | GB2489382A (https=) |
| MX (1) | MX2013008257A (https=) |
| PH (1) | PH12013501437A1 (https=) |
| RU (1) | RU2013138372A (https=) |
| SG (1) | SG191291A1 (https=) |
| TW (1) | TW201245144A (https=) |
| WO (1) | WO2012098033A1 (https=) |
| ZA (1) | ZA201304822B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2012208693B2 (en) * | 2011-01-19 | 2015-02-26 | Galapagos Nv | Azetidine derivatives useful for the treatment of metabolic and inflammatory diseases |
| CN105916500A (zh) | 2013-11-27 | 2016-08-31 | 欧洲筛选有限公司 | 用于治疗炎性疾病的化合物、药物组合物和方法 |
| US9839644B2 (en) | 2014-09-09 | 2017-12-12 | ARKAY Therapeutics, LLC | Formulations and methods for treatment of metabolic syndrome |
| KR101656662B1 (ko) * | 2014-11-18 | 2016-09-12 | 한국생명공학연구원 | 2-옥소-1,2,3,4-테트라하이드로피리미딘-5-카르복사미드 유도체를 유효성분으로 함유하는 대사성 질환 예방 또는 치료용 약학적 조성물 |
| HK1251223A1 (en) * | 2015-07-07 | 2019-01-25 | Japan Tobacco, Inc. | Method for producing 7h-pyrrolo[2, 3-d]pyrimidine derivative and intermediate thereof |
| AU2017384317C1 (en) | 2016-12-21 | 2022-06-30 | Japan Tobacco Inc. | PROCESS FOR PREPARING 7H-PYRROLO[2,3-d]PYRIMIDINE DERIVATIVES AND SYNTHETIC INTERMEDIATES THEREOF |
| BR102018007822A2 (pt) | 2017-04-20 | 2018-11-06 | Gilead Sciences, Inc. | composto, métodos para inibir pd-1, pd-l1 e/ou interação de pd-1/pd-l1 e para tratamento de câncer, composição farmacêutica, e, kit para tratamento de ou prevenção de câncer ou uma doença ou condição |
| TWI707849B (zh) | 2018-02-13 | 2020-10-21 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| KR102591947B1 (ko) | 2018-04-19 | 2023-10-25 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
| CN108863980A (zh) * | 2018-07-05 | 2018-11-23 | 浙江工业大学 | 一种合成1-(5-苯并噻唑基)乙酮的方法 |
| EP3820572B1 (en) | 2018-07-13 | 2023-08-16 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| US11236085B2 (en) | 2018-10-24 | 2022-02-01 | Gilead Sciences, Inc. | PD-1/PD-L1 inhibitors |
| CN110684000B (zh) * | 2019-10-18 | 2021-08-31 | 上海皓元医药股份有限公司 | 苯并呋喃衍生物的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5927869A (ja) | 1982-08-06 | 1984-02-14 | Sagami Chem Res Center | ４−オキソ−４，５，６，７−テトラヒドロインド−ルの製造方法 |
| US9017949B2 (en) * | 2004-09-22 | 2015-04-28 | Arena Pharmacueticals, Inc. | Method of screening for compounds useful in the treatment of insulin resistance, impaired glucose tolerance or diabetes |
| EP1888618A4 (en) * | 2005-05-23 | 2009-07-15 | Neuren Pharmaceuticals Ltd | Analogs of glycyl-prolyl-glutamate |
| US20070202515A1 (en) * | 2005-10-12 | 2007-08-30 | Pathologica, Llc. | Promac signature application |
| WO2007052466A1 (ja) * | 2005-11-04 | 2007-05-10 | Eisai R & D Management Co., Ltd. | Ｇｐｒ４０とホスホリパーゼとを用いる疾患に有用な物質のスクリーニング方法 |
| PE20070978A1 (es) * | 2006-02-14 | 2007-11-15 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE FOSFATIDILINOSITOL 3-QUINASAS (PI3Ks) |
| WO2008135525A2 (en) * | 2007-05-02 | 2008-11-13 | Boehringer Ingelheim International Gmbh | Substituted azetidines, manufacturing and use thereof as medicaments |
| MX2010008993A (es) | 2008-02-21 | 2010-09-07 | Actelion Pharmaceuticals Ltd | Derivados de 2-aza-biciclo-[2.2.1]heptano. |
| JP2010051307A (ja) * | 2008-07-28 | 2010-03-11 | Eisai R & D Management Co Ltd | Ｔｈ１７細胞およびＴｒｅｇ細胞の分化誘導を調節する物質のスクリーニング方法 |
| AU2012208693B2 (en) * | 2011-01-19 | 2015-02-26 | Galapagos Nv | Azetidine derivatives useful for the treatment of metabolic and inflammatory diseases |
-
2012
- 2012-01-10 AU AU2012208693A patent/AU2012208693B2/en not_active Expired - Fee Related
- 2012-01-10 US US13/980,798 patent/US8759334B2/en not_active Expired - Fee Related
- 2012-01-10 CN CN2012800059625A patent/CN103328442A/zh active Pending
- 2012-01-10 RU RU2013138372/04A patent/RU2013138372A/ru not_active Application Discontinuation
- 2012-01-10 PH PH1/2013/501437A patent/PH12013501437A1/en unknown
- 2012-01-10 WO PCT/EP2012/050297 patent/WO2012098033A1/en not_active Ceased
- 2012-01-10 JP JP2013549769A patent/JP2014507414A/ja active Pending
- 2012-01-10 CA CA2824460A patent/CA2824460A1/en not_active Abandoned
- 2012-01-10 BR BR112013018286A patent/BR112013018286A2/pt not_active IP Right Cessation
- 2012-01-10 GB GB1213267.6A patent/GB2489382A/en not_active Withdrawn
- 2012-01-10 KR KR1020137020884A patent/KR20140040104A/ko not_active Withdrawn
- 2012-01-10 SG SG2013048038A patent/SG191291A1/en unknown
- 2012-01-10 EP EP12700552.8A patent/EP2665704A1/en not_active Withdrawn
- 2012-01-10 MX MX2013008257A patent/MX2013008257A/es not_active Application Discontinuation
- 2012-01-13 AR ARP120100129A patent/AR084857A1/es unknown
- 2012-01-18 TW TW101102008A patent/TW201245144A/zh unknown
-
2013
- 2013-06-27 ZA ZA2013/04822A patent/ZA201304822B/en unknown
- 2013-08-15 CO CO13194671A patent/CO6741223A2/es unknown
-
2014
- 2014-06-23 US US14/311,574 patent/US20140371198A1/en not_active Abandoned
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