JP2013500996A5 - - Google Patents
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- Publication number
- JP2013500996A5 JP2013500996A5 JP2012523087A JP2012523087A JP2013500996A5 JP 2013500996 A5 JP2013500996 A5 JP 2013500996A5 JP 2012523087 A JP2012523087 A JP 2012523087A JP 2012523087 A JP2012523087 A JP 2012523087A JP 2013500996 A5 JP2013500996 A5 JP 2013500996A5
- Authority
- JP
- Japan
- Prior art keywords
- oxazine
- imidazo
- dihydro
- nitro
- trifluoromethoxy
- 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
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 2
- 230000000813 microbial effect Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- DNQCENQMHBLTIQ-SNDJDQCESA-N (6s)-2-nitro-6-[(e)-3-[4-[4-(trifluoromethoxy)phenyl]phenyl]prop-2-enoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])C\C=C\C(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 DNQCENQMHBLTIQ-SNDJDQCESA-N 0.000 claims 1
- ADWWYRLDGKOSBI-IBGZPJMESA-N (6s)-2-nitro-6-[3-[4-[4-(trifluoromethoxy)phenyl]phenyl]prop-2-ynoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC#CC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 ADWWYRLDGKOSBI-IBGZPJMESA-N 0.000 claims 1
- NELHGNKIZTVOEP-INIZCTEOSA-N (6s)-2-nitro-6-[4-[4-(trifluoromethoxy)phenyl]phenoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])C(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 NELHGNKIZTVOEP-INIZCTEOSA-N 0.000 claims 1
- DXDURKGYSJINPQ-SNDJDQCESA-N (6s)-2-nitro-6-[[4-[(e)-2-[4-(trifluoromethoxy)phenyl]ethenyl]phenyl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1)=CC=C1\C=C\C1=CC=C(OC(F)(F)F)C=C1 DXDURKGYSJINPQ-SNDJDQCESA-N 0.000 claims 1
- POZDECFNMBVWHV-IBGZPJMESA-N (6s)-2-nitro-6-[[4-[2-[4-(trifluoromethoxy)phenyl]ethynyl]phenyl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1)=CC=C1C#CC1=CC=C(OC(F)(F)F)C=C1 POZDECFNMBVWHV-IBGZPJMESA-N 0.000 claims 1
- OTJRQXNIDYSJLS-KRWDZBQOSA-N (6s)-2-nitro-6-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 OTJRQXNIDYSJLS-KRWDZBQOSA-N 0.000 claims 1
- UQZUAALOBIRJTJ-HNNXBMFYSA-N (6s)-2-nitro-6-[[4-[5-(trifluoromethyl)pyridin-2-yl]phenyl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=N1 UQZUAALOBIRJTJ-HNNXBMFYSA-N 0.000 claims 1
- XNCQSDZPSYNLJS-HNNXBMFYSA-N (6s)-2-nitro-6-[[4-[6-(trifluoromethyl)pyridin-3-yl]phenyl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)N=C1 XNCQSDZPSYNLJS-HNNXBMFYSA-N 0.000 claims 1
- PBMCMZFEDXCLOG-SFHVURJKSA-N (6s)-2-nitro-6-[[4-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1)=CC=C1CC1=CC=C(OC(F)(F)F)C=C1 PBMCMZFEDXCLOG-SFHVURJKSA-N 0.000 claims 1
- IMAWBGLPMIBFHZ-SFHVURJKSA-N (6s)-2-nitro-6-[[5-[2-[4-(trifluoromethoxy)phenyl]ethynyl]pyridin-2-yl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(N=C1)=CC=C1C#CC1=CC=C(OC(F)(F)F)C=C1 IMAWBGLPMIBFHZ-SFHVURJKSA-N 0.000 claims 1
- CADGZOMZUKQNAZ-INIZCTEOSA-N (6s)-2-nitro-6-[[5-[2-[6-(trifluoromethyl)pyridin-3-yl]ethynyl]pyridin-2-yl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(N=C1)=CC=C1C#CC1=CC=C(C(F)(F)F)N=C1 CADGZOMZUKQNAZ-INIZCTEOSA-N 0.000 claims 1
- GSXVUXVAKTVPOV-INIZCTEOSA-N (6s)-2-nitro-6-[[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 GSXVUXVAKTVPOV-INIZCTEOSA-N 0.000 claims 1
- JRMJATJTHVCYRK-SFHVURJKSA-N (6s)-2-nitro-6-[[6-[2-[4-(trifluoromethoxy)phenyl]ethynyl]pyridin-3-yl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=N1)=CC=C1C#CC1=CC=C(OC(F)(F)F)C=C1 JRMJATJTHVCYRK-SFHVURJKSA-N 0.000 claims 1
- ZXSGSFMORAILEY-HNNXBMFYSA-N (6s)-2-nitro-6-[[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 ZXSGSFMORAILEY-HNNXBMFYSA-N 0.000 claims 1
- XRFJSLRWSQZSIS-INIZCTEOSA-N (6s)-6-[[2-fluoro-4-[4-(trifluoromethoxy)phenyl]phenyl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C(=C1)F)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 XRFJSLRWSQZSIS-INIZCTEOSA-N 0.000 claims 1
- XQXUVNHTKBBBAL-AWEZNQCLSA-N (6s)-6-[[2-fluoro-4-[5-(trifluoromethyl)pyridin-2-yl]phenyl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C(=C1)F)=CC=C1C1=CC=C(C(F)(F)F)C=N1 XQXUVNHTKBBBAL-AWEZNQCLSA-N 0.000 claims 1
- SSMOYRIVMMBRLN-AWEZNQCLSA-N (6s)-6-[[2-fluoro-4-[6-(trifluoromethyl)pyridin-3-yl]phenyl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C(=C1)F)=CC=C1C1=CC=C(C(F)(F)F)N=C1 SSMOYRIVMMBRLN-AWEZNQCLSA-N 0.000 claims 1
- OAMFSVZGPGCNNM-HNNXBMFYSA-N (6s)-6-[[3-fluoro-4-[4-(trifluoromethoxy)phenyl]phenyl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1F)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 OAMFSVZGPGCNNM-HNNXBMFYSA-N 0.000 claims 1
- BFENJCKAYWGGGH-HNNXBMFYSA-N (6s)-6-[[4-(5-fluoropyridin-2-yl)phenyl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1)=CC=C1C1=CC=C(F)C=N1 BFENJCKAYWGGGH-HNNXBMFYSA-N 0.000 claims 1
- AFVACAZNAUREGB-HNNXBMFYSA-N (6s)-6-[[4-[2-chloro-4-(trifluoromethoxy)phenyl]phenyl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1Cl AFVACAZNAUREGB-HNNXBMFYSA-N 0.000 claims 1
- DYXLDHDTFUSQMO-HNNXBMFYSA-N (6s)-6-[[4-[3-fluoro-4-(trifluoromethoxy)phenyl]phenyl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C(F)=C1 DYXLDHDTFUSQMO-HNNXBMFYSA-N 0.000 claims 1
- KERVIECOCWUCGM-AWEZNQCLSA-N (6s)-6-[[5-[3-fluoro-4-(trifluoromethoxy)phenyl]pyridin-2-yl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C(F)=C1 KERVIECOCWUCGM-AWEZNQCLSA-N 0.000 claims 1
- IVKZYCCYHBNVHH-HNNXBMFYSA-N (6s)-6-[[6-(4-fluorophenyl)pyridin-3-yl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=N1)=CC=C1C1=CC=C(F)C=C1 IVKZYCCYHBNVHH-HNNXBMFYSA-N 0.000 claims 1
- BBDYLXMLKRJEST-ZDUSSCGKSA-N (6s)-6-[[6-[3-chloro-4-(trifluoromethoxy)phenyl]pyridin-3-yl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C(Cl)=C1 BBDYLXMLKRJEST-ZDUSSCGKSA-N 0.000 claims 1
- UZCUJRHCBANHCD-ZDUSSCGKSA-N (6s)-6-[[6-[3-fluoro-4-(trifluoromethoxy)phenyl]pyridin-3-yl]methoxy]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])CC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C(F)=C1 UZCUJRHCBANHCD-ZDUSSCGKSA-N 0.000 claims 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000002924 anti-infective effect Effects 0.000 claims 1
- 239000000872 buffer Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- -1 inert ingredients Substances 0.000 claims 1
- 229940060367 inert ingredients Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23039609P | 2009-07-31 | 2009-07-31 | |
| US61/230,396 | 2009-07-31 | ||
| PCT/US2010/043906 WO2011014774A1 (en) | 2009-07-31 | 2010-07-30 | Nitroimidazooxazines and their uses in anti-tubercular therapy |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013500996A JP2013500996A (ja) | 2013-01-10 |
| JP2013500996A5 true JP2013500996A5 (https=) | 2013-09-12 |
| JP5781072B2 JP5781072B2 (ja) | 2015-09-16 |
Family
ID=42937154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012523087A Expired - Fee Related JP5781072B2 (ja) | 2009-07-31 | 2010-07-30 | ニトロイミダゾオキサジンおよび抗−結核療法におけるその使用 |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP2459571B1 (https=) |
| JP (1) | JP5781072B2 (https=) |
| KR (1) | KR101746482B1 (https=) |
| CN (1) | CN102753558B (https=) |
| AU (1) | AU2010278777B2 (https=) |
| BR (1) | BR112012002278A2 (https=) |
| CA (1) | CA2769359C (https=) |
| ES (1) | ES2536997T3 (https=) |
| IN (1) | IN2012DN01414A (https=) |
| NZ (1) | NZ598121A (https=) |
| RU (1) | RU2542988C2 (https=) |
| WO (1) | WO2011014774A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5916739B2 (ja) * | 2011-04-15 | 2016-05-11 | 大塚製薬株式会社 | ６，７−ジヒドロイミダゾ［２，１−ｂ］［１，３］オキサジン化合物 |
| CN104059082B (zh) * | 2013-03-21 | 2016-08-03 | 苏州迈泰生物技术有限公司 | 硝基咪唑杂环类化合物及其在制备治疗结核病药物中的应用 |
| KR101682356B1 (ko) | 2014-11-04 | 2016-12-06 | 한국화학연구원 | 이미다조 옥사진 유도체, 이의 약학적으로 허용 가능한 염 또는 이의 광학이성질체 및 이를 유효성분으로 함유하는 약제학적 조성물 |
| CN107207532B (zh) | 2015-01-29 | 2019-07-30 | 南京明德新药研发股份有限公司 | 抗肺结核病的硝基咪唑衍生物 |
| CN108047248A (zh) * | 2018-02-12 | 2018-05-18 | 丹诺医药(苏州）有限公司 | 噁唑烷酮-硝基咪唑类偶联分子的应用 |
| CN113527331B (zh) * | 2020-04-17 | 2024-05-28 | 南京长澳医药科技有限公司 | 硝基咪唑类衍生物及其制备方法和用途 |
| CN113355439A (zh) * | 2021-06-07 | 2021-09-07 | 深圳市普瑞康生物技术有限公司 | 一种结核分枝杆菌潜伏感染及发病的新型组合检测方法 |
| CN114469946B (zh) * | 2022-02-24 | 2023-10-24 | 首都医科大学附属北京胸科医院 | 德拉马尼作为cxcl10抑制剂的用途 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100342761B1 (ko) | 1994-03-08 | 2002-12-06 | 와이어쓰 | 항과혈당제로서의 티아졸리딘디온 유도체 |
| US5668127A (en) * | 1995-06-26 | 1997-09-16 | Pathogenesis Corporation | Nitroimidazole antibacterial compounds and methods of use thereof |
| US6087358A (en) * | 1995-06-26 | 2000-07-11 | Pathogenesis Corporation | Nitro-[2,1-b]imidazopyran compounds and antibacterial uses thereof |
| TWI347946B (en) * | 2002-10-11 | 2011-09-01 | Otsuka Pharma Co Ltd | 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound |
| UA91822C2 (ru) * | 2003-10-31 | 2010-09-10 | Оцука Фармасьютикел Ко., Лтд. | СОЕДИНЕНИЕ 2,3-ДИГИДРО-6-НИТРОИМИДАЗО[2,1-b]ОКСАЗОЛА ДЛЯ ЛЕЧЕНИЯ ТУБЕРКУЛЕЗА |
| ATE382609T1 (de) | 2004-01-16 | 2008-01-15 | Sumitomo Chemical Co | Malononitrilverbindungen als pestizide |
| TWI300409B (en) * | 2004-02-18 | 2008-09-01 | Otsuka Pharma Co Ltd | Method for producing 4-nitroimidazole compound |
| WO2006043121A1 (en) * | 2004-10-20 | 2006-04-27 | Ranbaxy Laboratories Limited | Oxazolidinone derivatives as antimicrobials |
| KR20080038369A (ko) * | 2005-07-28 | 2008-05-06 | 버텍스 파마슈티칼스 인코포레이티드 | 카스파제 억제제 프로드럭 |
| US20080275035A1 (en) | 2005-12-23 | 2008-11-06 | Jan Jiricek | Nitroimidazole Compounds |
| CA2712613C (en) * | 2008-03-26 | 2017-02-28 | Global Alliance For Tb Drug Development | Bicyclic nitroimidazoles covalently linked to substituted phenyl oxazolidinones |
-
2010
- 2010-07-30 WO PCT/US2010/043906 patent/WO2011014774A1/en not_active Ceased
- 2010-07-30 ES ES10742955.7T patent/ES2536997T3/es active Active
- 2010-07-30 BR BR112012002278-4A patent/BR112012002278A2/pt not_active IP Right Cessation
- 2010-07-30 CA CA2769359A patent/CA2769359C/en not_active Expired - Fee Related
- 2010-07-30 CN CN201080041453.9A patent/CN102753558B/zh not_active Expired - Fee Related
- 2010-07-30 EP EP10742955.7A patent/EP2459571B1/en not_active Not-in-force
- 2010-07-30 JP JP2012523087A patent/JP5781072B2/ja not_active Expired - Fee Related
- 2010-07-30 IN IN1414DEN2012 patent/IN2012DN01414A/en unknown
- 2010-07-30 AU AU2010278777A patent/AU2010278777B2/en not_active Ceased
- 2010-07-30 KR KR1020127005320A patent/KR101746482B1/ko not_active Expired - Fee Related
- 2010-07-30 RU RU2012107176/04A patent/RU2542988C2/ru not_active IP Right Cessation
- 2010-07-30 NZ NZ598121A patent/NZ598121A/xx not_active IP Right Cessation
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