JP2009536939A5 - - Google Patents
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- Publication number
- JP2009536939A5 JP2009536939A5 JP2009508535A JP2009508535A JP2009536939A5 JP 2009536939 A5 JP2009536939 A5 JP 2009536939A5 JP 2009508535 A JP2009508535 A JP 2009508535A JP 2009508535 A JP2009508535 A JP 2009508535A JP 2009536939 A5 JP2009536939 A5 JP 2009536939A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- pharmaceutically acceptable
- epoxide
- acetamide
- 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 15
- 238000000034 method Methods 0.000 claims 12
- 241000894006 Bacteria Species 0.000 claims 4
- 150000002118 epoxides Chemical class 0.000 claims 4
- 208000015181 infectious disease Diseases 0.000 claims 4
- 230000000813 microbial effect Effects 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 150000004703 alkoxides Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical group CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000012025 fluorinating agent Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 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 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims 2
- 241001148471 unidentified anaerobic bacterium Species 0.000 claims 2
- VUYQBMXVCZBVHP-UHFFFAOYSA-N 1,1-difluoroethanol Chemical compound CC(O)(F)F VUYQBMXVCZBVHP-UHFFFAOYSA-N 0.000 claims 1
- RHZFDRSWJULINI-UHFFFAOYSA-N 1,1-difluoropropan-1-ol Chemical compound CCC(O)(F)F RHZFDRSWJULINI-UHFFFAOYSA-N 0.000 claims 1
- HDBGBTNNPRCVND-UHFFFAOYSA-N 3,3,3-trifluoropropan-1-ol Chemical compound OCCC(F)(F)F HDBGBTNNPRCVND-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- KKXVKWCCFKHMMV-NRXISQOPSA-N FC=1C=C(C=C(C1N1C(CC(CC1)O)COCC(F)(F)F)F)N1C(O[C@H](C1)CNC(C)=O)=O Chemical compound FC=1C=C(C=C(C1N1C(CC(CC1)O)COCC(F)(F)F)F)N1C(O[C@H](C1)CNC(C)=O)=O KKXVKWCCFKHMMV-NRXISQOPSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims 1
- 230000000397 acetylating effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- BNTFCVMJHBNJAR-UHFFFAOYSA-N n,n-diethyl-1,1,2,3,3,3-hexafluoropropan-1-amine Chemical compound CCN(CC)C(F)(F)C(F)C(F)(F)F BNTFCVMJHBNJAR-UHFFFAOYSA-N 0.000 claims 1
- SAVQQRYWWAGSQW-UHFFFAOYSA-N n-methyl-n-(trifluoro-$l^{4}-sulfanyl)methanamine Chemical compound CN(C)S(F)(F)F SAVQQRYWWAGSQW-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- CCKAYTBOIIPZGA-UHFFFAOYSA-N trifluoro(pyrrolidin-1-yl)-$l^{4}-sulfane Chemical compound FS(F)(F)N1CCCC1 CCKAYTBOIIPZGA-UHFFFAOYSA-N 0.000 claims 1
- WZCZNEGTXVXAAS-UHFFFAOYSA-N trifluoromethanol Chemical compound OC(F)(F)F WZCZNEGTXVXAAS-UHFFFAOYSA-N 0.000 claims 1
- KQYWHJICYXXDSQ-UHFFFAOYSA-M trimethylsulfoxonium chloride Chemical compound [Cl-].C[S+](C)(C)=O KQYWHJICYXXDSQ-UHFFFAOYSA-M 0.000 claims 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical group [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 claims 1
- 0 CC(NCC(CN1c(cc2F)cc(F)c2N2CCC(*)(CO*)CC2)OC1=O)=O Chemical compound CC(NCC(CN1c(cc2F)cc(F)c2N2CCC(*)(CO*)CC2)OC1=O)=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN719/MUM/2006 | 2006-05-09 | ||
| IN719MU2006 | 2006-05-09 | ||
| PCT/IB2007/001179 WO2007132314A2 (en) | 2006-05-09 | 2007-05-08 | Substituted piperidino phenyloxazolidinones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009536939A JP2009536939A (ja) | 2009-10-22 |
| JP2009536939A5 true JP2009536939A5 (enExample) | 2010-06-24 |
| JP5313126B2 JP5313126B2 (ja) | 2013-10-09 |
Family
ID=38694273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009508535A Expired - Fee Related JP5313126B2 (ja) | 2006-05-09 | 2007-05-08 | 置換ピペリジノフェニルオキサゾリジノン |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8217058B2 (enExample) |
| EP (1) | EP2018792B1 (enExample) |
| JP (1) | JP5313126B2 (enExample) |
| KR (1) | KR101345445B1 (enExample) |
| CN (1) | CN102106184B (enExample) |
| AU (1) | AU2007251289A1 (enExample) |
| BR (1) | BRPI0712535A2 (enExample) |
| CA (1) | CA2651634C (enExample) |
| ES (1) | ES2556183T3 (enExample) |
| MX (1) | MX2008013371A (enExample) |
| RU (1) | RU2008148319A (enExample) |
| WO (1) | WO2007132314A2 (enExample) |
| ZA (1) | ZA200809724B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7687627B2 (en) * | 2003-09-08 | 2010-03-30 | Wockhardt Limited | Substituted piperidino phenyloxazolidinones having antimicrobial activity with improved in vivo efficacy |
| US8217058B2 (en) * | 2006-05-09 | 2012-07-10 | Wockhardt Ltd. | Substituted piperidino phenyloxazolidinones |
| CN101616588B (zh) | 2006-09-25 | 2013-09-25 | 沃克哈特研究中心 | 取代的哌啶子基苯基噁唑烷酮 |
| CN103391943A (zh) * | 2010-11-03 | 2013-11-13 | 沃克哈特有限公司 | 磷酸单-(1-{4-[(s)-5-(乙酰基氨基-甲基)-2-氧代-噁唑烷-3-基]-2,6-二氟苯基}-4-甲氧基甲基-哌啶-4-基)酯的制备方法 |
| WO2015173664A1 (en) | 2014-05-14 | 2015-11-19 | Wockhardt Limited | Process for the preparation of (5s)-n-{3-[3,5-difluoro-4-(4-hydroxy-4-methoxymethyl-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide |
| WO2018048882A1 (en) | 2016-09-06 | 2018-03-15 | The Research Foundation For The State University Of New York | Positron imaging tomography imaging agent composition and method for bacterial infection |
| WO2023209678A1 (en) * | 2022-04-29 | 2023-11-02 | Zenal Pharmachem Llc | Aryl azo pyrazole derivatives as antimicrobial agent |
| WO2023209677A2 (en) * | 2022-04-29 | 2023-11-02 | Zenal Pharmachem Llc | A novel aryl azo pyrazole compound and its synthesis |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5668285A (en) | 1986-10-31 | 1997-09-16 | The United States Of America As Represented By The Department Of Health And Human Services | Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates |
| US5668286A (en) * | 1994-03-15 | 1997-09-16 | Pharmacia & Upjohn Company | Oxazolidinone derivatives and pharmaceutical compositions containing them |
| JPH0873455A (ja) * | 1994-03-15 | 1996-03-19 | Upjohn Co:The | オキサゾリジノン誘導体及びこれを有効成分とする医薬組成物 |
| CA2492194A1 (en) * | 2002-07-11 | 2004-01-22 | Wockhardt Limited | Antibacterial cyano-(substituted)-methylenepiperidinophenyl oxazolidinones targeting multiple ribonucleoproteins sites |
| US7687627B2 (en) * | 2003-09-08 | 2010-03-30 | Wockhardt Limited | Substituted piperidino phenyloxazolidinones having antimicrobial activity with improved in vivo efficacy |
| WO2007023507A2 (en) * | 2005-06-20 | 2007-03-01 | Wockhardt Limited | Oxazolidinones bearing antimicrobial activity composition and methods of preparation |
| US8217058B2 (en) * | 2006-05-09 | 2012-07-10 | Wockhardt Ltd. | Substituted piperidino phenyloxazolidinones |
-
2007
- 2007-05-08 US US12/225,744 patent/US8217058B2/en not_active Expired - Fee Related
- 2007-05-08 JP JP2009508535A patent/JP5313126B2/ja not_active Expired - Fee Related
- 2007-05-08 CN CN200780016549.8A patent/CN102106184B/zh not_active Expired - Fee Related
- 2007-05-08 WO PCT/IB2007/001179 patent/WO2007132314A2/en not_active Ceased
- 2007-05-08 ES ES07734494.3T patent/ES2556183T3/es active Active
- 2007-05-08 RU RU2008148319/04A patent/RU2008148319A/ru not_active Application Discontinuation
- 2007-05-08 CA CA2651634A patent/CA2651634C/en not_active Expired - Fee Related
- 2007-05-08 BR BRPI0712535-6A patent/BRPI0712535A2/pt not_active Application Discontinuation
- 2007-05-08 MX MX2008013371A patent/MX2008013371A/es active IP Right Grant
- 2007-05-08 EP EP07734494.3A patent/EP2018792B1/en not_active Not-in-force
- 2007-05-08 AU AU2007251289A patent/AU2007251289A1/en not_active Abandoned
-
2008
- 2008-11-14 ZA ZA2008/09724A patent/ZA200809724B/en unknown
- 2008-12-02 KR KR1020087029525A patent/KR101345445B1/ko not_active Expired - Fee Related
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