JP2008519788A5 - - Google Patents
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- Publication number
- JP2008519788A5 JP2008519788A5 JP2007540573A JP2007540573A JP2008519788A5 JP 2008519788 A5 JP2008519788 A5 JP 2008519788A5 JP 2007540573 A JP2007540573 A JP 2007540573A JP 2007540573 A JP2007540573 A JP 2007540573A JP 2008519788 A5 JP2008519788 A5 JP 2008519788A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- oxo
- carboxy
- dimethylamino
- erythromycin
- 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.)
- Withdrawn
Links
- -1 3-carboxy-1,4-dihydro-1-dimethylamino-4-oxo-6-quinolinyl Chemical group 0.000 claims 51
- 125000000217 alkyl group Chemical group 0.000 claims 35
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 28
- 229960002626 clarithromycin Drugs 0.000 claims 24
- 229960003276 erythromycin Drugs 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000006308 propyl amino group Chemical group 0.000 claims 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 229960004099 azithromycin Drugs 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 3
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical group NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 229950010035 davercin Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- TYQXKHPOXXXCTP-CSLYCKPJSA-N erythromycin A 2'-propanoate Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(=O)CC)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 TYQXKHPOXXXCTP-CSLYCKPJSA-N 0.000 claims 1
- 229950001028 erythromycin propionate Drugs 0.000 claims 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0424959A GB0424959D0 (en) | 2004-11-11 | 2004-11-11 | Novel compounds |
| PCT/EP2005/012038 WO2006050942A1 (en) | 2004-11-11 | 2005-11-09 | Macrolones - amino substituted quinolones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008519788A JP2008519788A (ja) | 2008-06-12 |
| JP2008519788A5 true JP2008519788A5 (enExample) | 2008-12-25 |
Family
ID=33523587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007540573A Withdrawn JP2008519788A (ja) | 2004-11-11 | 2005-11-09 | マクロロン−アミノ置換キノロン |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7718621B2 (enExample) |
| EP (1) | EP1824870A1 (enExample) |
| JP (1) | JP2008519788A (enExample) |
| KR (1) | KR20070085919A (enExample) |
| CN (1) | CN101098881A (enExample) |
| AR (1) | AR053311A1 (enExample) |
| AU (1) | AU2005303961A1 (enExample) |
| BR (1) | BRPI0517792A (enExample) |
| CA (1) | CA2587413A1 (enExample) |
| GB (1) | GB0424959D0 (enExample) |
| IL (1) | IL182978A0 (enExample) |
| MA (1) | MA29213B1 (enExample) |
| MX (1) | MX2007005776A (enExample) |
| NO (1) | NO20072939L (enExample) |
| PE (1) | PE20061137A1 (enExample) |
| RU (1) | RU2007121581A (enExample) |
| TW (1) | TW200630378A (enExample) |
| WO (1) | WO2006050942A1 (enExample) |
| ZA (1) | ZA200703603B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7601695B2 (en) | 2003-03-10 | 2009-10-13 | Optimer Pharmaceuticals, Inc. | Antibacterial agents |
| WO2007054295A1 (en) * | 2005-11-09 | 2007-05-18 | Glaxo Group Limited | New 4*-substituted erythromycin derivative |
| EP1879904A1 (en) * | 2005-05-10 | 2008-01-23 | GlaxoSmithKline istrazivacki centar Zagreb d.o.o. | 4" amino linked macrolides useful for the treatment of microbial infections |
| WO2007054296A1 (en) * | 2005-11-09 | 2007-05-18 | Glaxo Group Limited | Macrolones |
| NZ583878A (en) | 2007-09-14 | 2012-10-26 | Vertex Pharma | Modulators of ABC transporter and cystic fibrosis transmembrane conductance regulator (CFTR) |
| AU2008316830B2 (en) | 2007-10-25 | 2016-03-17 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| TW200946109A (en) * | 2008-05-09 | 2009-11-16 | Enanta Pharm Inc | Anti-bacterial activity of 9-hydroxy derivatives 6, 11-bicyclolides |
| CN107854477A (zh) | 2008-10-24 | 2018-03-30 | 森普拉制药公司 | 使用含三唑的大环内酯治疗抗性疾病的方法 |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| US9480679B2 (en) | 2009-09-10 | 2016-11-01 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and MAC diseases |
| BR112012029586A2 (pt) * | 2010-05-20 | 2016-08-02 | Cempra Pharmaceuticals Inc | processos para preparar macrolídeos e cetolídeos e intermediários dos mesmos |
| KR20130120458A (ko) | 2010-09-10 | 2013-11-04 | 셈프라 파마슈티컬스, 인크. | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
| WO2013148891A1 (en) | 2012-03-27 | 2013-10-03 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| WO2014152326A1 (en) | 2013-03-14 | 2014-09-25 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| AU2014233240B2 (en) | 2013-03-15 | 2018-08-09 | Cempra Pharmaceuticals, Inc. | Convergent processes for preparing macrolide antibacterial agents |
| CN106589023A (zh) * | 2016-11-22 | 2017-04-26 | 宜昌东阳光药业股份有限公司 | 一种罗红霉素杂质及其合成方法 |
| CN110475777B (zh) | 2017-03-30 | 2022-04-15 | 豪夫迈·罗氏有限公司 | 用于治疗和预防细菌感染的新吡啶并[2,3-b]吲哚化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2808070A1 (de) * | 1978-02-24 | 1979-08-30 | Bayer Ag | Verfahren zur herstellung von 4-pyridon-3-carbonsaeuren und/oder deren derivaten |
| GB0127349D0 (en) | 2001-11-14 | 2002-01-02 | Glaxo Group Ltd | Macrolides |
| GB0225384D0 (en) | 2002-10-31 | 2002-12-11 | Glaxo Group Ltd | Novel compounds |
-
2004
- 2004-11-11 GB GB0424959A patent/GB0424959D0/en not_active Ceased
-
2005
- 2005-11-09 AU AU2005303961A patent/AU2005303961A1/en not_active Abandoned
- 2005-11-09 CA CA002587413A patent/CA2587413A1/en not_active Abandoned
- 2005-11-09 JP JP2007540573A patent/JP2008519788A/ja not_active Withdrawn
- 2005-11-09 RU RU2007121581/04A patent/RU2007121581A/ru not_active Application Discontinuation
- 2005-11-09 BR BRPI0517792-8A patent/BRPI0517792A/pt not_active IP Right Cessation
- 2005-11-09 MX MX2007005776A patent/MX2007005776A/es unknown
- 2005-11-09 WO PCT/EP2005/012038 patent/WO2006050942A1/en not_active Ceased
- 2005-11-09 CN CNA2005800463765A patent/CN101098881A/zh active Pending
- 2005-11-09 US US11/719,004 patent/US7718621B2/en not_active Expired - Fee Related
- 2005-11-09 KR KR1020077012942A patent/KR20070085919A/ko not_active Withdrawn
- 2005-11-09 EP EP05801894A patent/EP1824870A1/en not_active Withdrawn
- 2005-11-09 TW TW094139277A patent/TW200630378A/zh unknown
- 2005-11-09 AR ARP050104704A patent/AR053311A1/es not_active Application Discontinuation
- 2005-11-09 PE PE2005001311A patent/PE20061137A1/es not_active Application Discontinuation
-
2006
- 2006-11-07 US US12/093,145 patent/US20080269146A1/en not_active Abandoned
-
2007
- 2007-05-03 IL IL182978A patent/IL182978A0/en unknown
- 2007-05-04 ZA ZA200703603A patent/ZA200703603B/en unknown
- 2007-05-22 MA MA29930A patent/MA29213B1/fr unknown
- 2007-06-08 NO NO20072939A patent/NO20072939L/no not_active Application Discontinuation
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