JP2006524706A5 - - Google Patents
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- Publication number
- JP2006524706A5 JP2006524706A5 JP2006513319A JP2006513319A JP2006524706A5 JP 2006524706 A5 JP2006524706 A5 JP 2006524706A5 JP 2006513319 A JP2006513319 A JP 2006513319A JP 2006513319 A JP2006513319 A JP 2006513319A JP 2006524706 A5 JP2006524706 A5 JP 2006524706A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- hydrogen
- heteroaryl
- aryl
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims 42
- 239000001257 hydrogen Substances 0.000 claims 42
- 150000002431 hydrogen Chemical group 0.000 claims 34
- 125000001072 heteroaryl group Chemical group 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000002148 esters Chemical class 0.000 claims 17
- 239000000651 prodrug Substances 0.000 claims 17
- 229940002612 prodrug Drugs 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- -1 wherein Chemical compound 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000003107 substituted aryl group Chemical group 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 3
- 208000035143 Bacterial infection Diseases 0.000 claims 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 2
- 125000001843 C4-C10 alkenyl group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 1
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- XBPASXLWMTZZFC-UHFFFAOYSA-N 4-[4-(6-chloropyridin-3-yl)-2-methyl-1h-imidazol-5-yl]butan-1-amine Chemical compound N1C(C)=NC(C=2C=NC(Cl)=CC=2)=C1CCCCN XBPASXLWMTZZFC-UHFFFAOYSA-N 0.000 claims 1
- OIKYGVHOAKNOIT-UHFFFAOYSA-N 4-[4-(6-chloropyridin-3-yl)-5-methyl-1h-imidazol-2-yl]butan-1-amine Chemical compound N1C(CCCCN)=NC(C=2C=NC(Cl)=CC=2)=C1C OIKYGVHOAKNOIT-UHFFFAOYSA-N 0.000 claims 1
- SKSZYTFXIDNVRR-UHFFFAOYSA-N 4-[4-(6-chloropyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound NCCCCN1C=NC(C=2C=NC(Cl)=CC=2)=C1 SKSZYTFXIDNVRR-UHFFFAOYSA-N 0.000 claims 1
- KQPJSTREOMVENQ-UHFFFAOYSA-N 4-[4-(6-ethoxypyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound C1=NC(OCC)=CC=C1C1=CN(CCCCN)C=N1 KQPJSTREOMVENQ-UHFFFAOYSA-N 0.000 claims 1
- VYBHXZVSJYBFMA-UHFFFAOYSA-N 4-[4-(6-fluoropyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound NCCCCN1C=NC(C=2C=NC(F)=CC=2)=C1 VYBHXZVSJYBFMA-UHFFFAOYSA-N 0.000 claims 1
- IYWJLGFXMICCGN-UHFFFAOYSA-N 4-[4-(6-methoxypyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound C1=NC(OC)=CC=C1C1=CN(CCCCN)C=N1 IYWJLGFXMICCGN-UHFFFAOYSA-N 0.000 claims 1
- FMZZOIPURNVGLD-UHFFFAOYSA-N 4-[4-(6-methylpyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound C1=NC(C)=CC=C1C1=CN(CCCCN)C=N1 FMZZOIPURNVGLD-UHFFFAOYSA-N 0.000 claims 1
- LZPSNHQTMJQMHZ-UHFFFAOYSA-N 4-[5-(4-chloropyridin-3-yl)-1h-imidazol-2-yl]butan-1-amine Chemical compound N1C(CCCCN)=NC=C1C1=CN=CC=C1Cl LZPSNHQTMJQMHZ-UHFFFAOYSA-N 0.000 claims 1
- DFAGLOLGEMMVPT-UHFFFAOYSA-N 4-[5-(4-methoxypyridin-3-yl)-1h-imidazol-2-yl]butan-1-amine Chemical compound COC1=CC=NC=C1C1=CN=C(CCCCN)N1 DFAGLOLGEMMVPT-UHFFFAOYSA-N 0.000 claims 1
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims 1
- FWMIGRYEXUCAOR-UHFFFAOYSA-N 5-[1-(4-aminobutyl)imidazol-4-yl]-n-methylpyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=CN(CCCCN)C=N1 FWMIGRYEXUCAOR-UHFFFAOYSA-N 0.000 claims 1
- UGBFATORHKYKHA-UHFFFAOYSA-N 5-[1-(4-aminobutyl)imidazol-4-yl]pyridin-2-amine Chemical compound NCCCCN1C=NC(C=2C=NC(N)=CC=2)=C1 UGBFATORHKYKHA-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 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
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 0 CCC([C@](C)([C@@]([C@@](C)C([C@](C)C[C@](C)(*C)[C@](*C([C@@]1O)O[C@](C)C[C@@]1N(C)C)[C@@](C)C([C@]1C)=O)=O)N2CCCCC(C3)C=NC3C(CC3)=CN=C3Cl)OC2=O)OC1=O Chemical compound CCC([C@](C)([C@@]([C@@](C)C([C@](C)C[C@](C)(*C)[C@](*C([C@@]1O)O[C@](C)C[C@@]1N(C)C)[C@@](C)C([C@]1C)=O)=O)N2CCCCC(C3)C=NC3C(CC3)=CN=C3Cl)OC2=O)OC1=O 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46533703P | 2003-04-25 | 2003-04-25 | |
| PCT/US2004/012778 WO2004096823A2 (en) | 2003-04-25 | 2004-04-23 | Novel ketolide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006524706A JP2006524706A (ja) | 2006-11-02 |
| JP2006524706A5 true JP2006524706A5 (enExample) | 2007-05-10 |
Family
ID=33418228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006513319A Pending JP2006524706A (ja) | 2003-04-25 | 2004-04-23 | 新規なケトライド誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7163924B2 (enExample) |
| EP (1) | EP1618120A2 (enExample) |
| JP (1) | JP2006524706A (enExample) |
| CA (1) | CA2523541A1 (enExample) |
| WO (1) | WO2004096823A2 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7601695B2 (en) | 2003-03-10 | 2009-10-13 | Optimer Pharmaceuticals, Inc. | Antibacterial agents |
| US7332476B2 (en) * | 2003-04-25 | 2008-02-19 | Novartis Ag | Pyridyl substituted ketolide antibiotics |
| EP1928893A2 (en) | 2005-08-24 | 2008-06-11 | Rib-X Pharmaceuticals, Inc. | Triazole compounds and methods of making and using the same |
| EP1960413A2 (en) * | 2005-11-23 | 2008-08-27 | Ranbaxy Laboratories Limited | Macrolides derivatives as antibacterial agents |
| CN100494191C (zh) * | 2007-02-02 | 2009-06-03 | 广东东阳光药业有限公司 | 一种制备3-(咪唑-4-基)吡啶的方法 |
| AU2008316830B2 (en) | 2007-10-25 | 2016-03-17 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| 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 |
| EP2435460B1 (en) * | 2009-05-27 | 2015-01-07 | Wockhardt Limited | Ketolide compounds having antimicrobial activity |
| 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 |
| HRP20160168T1 (hr) | 2010-03-22 | 2016-03-25 | Cempra Pharmaceuticals Inc | Kristalne forme makrolida i njihova uporaba |
| BR112012029586A2 (pt) | 2010-05-20 | 2016-08-02 | Cempra Pharmaceuticals Inc | processos para preparar macrolídeos e cetolídeos e intermediários dos mesmos |
| US8796474B1 (en) | 2010-08-23 | 2014-08-05 | Rutgers, The State University Of New Jersey | Macrolide compounds and methods and intermediates useful for their preparation |
| KR20130120458A (ko) * | 2010-09-10 | 2013-11-04 | 셈프라 파마슈티컬스, 인크. | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
| EP2688900B1 (en) * | 2011-03-22 | 2016-09-28 | Wockhardt Limited | Process for preparation of ketolide compounds |
| 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 |
| CN103664788B (zh) * | 2013-12-04 | 2015-11-25 | 湖北生物医药产业技术研究院有限公司 | 制备美托咪啶的方法 |
| CN104650166B (zh) * | 2014-11-17 | 2017-12-05 | 广东东阳光药业有限公司 | 一种大环内酯的制备方法 |
| MX2019002444A (es) * | 2016-08-29 | 2019-09-02 | Univ Texas | Inhibidores de cinasa de cremallera de leucina dual (dlk) para el tratamiento de enfermedades. |
| WO2018067663A2 (en) * | 2016-10-04 | 2018-04-12 | Biopharmati Sa | Ketolides having antibacterial activity |
| US11560366B2 (en) | 2019-10-21 | 2023-01-24 | Board Of Regents, The University Of Texas System | Bicyclo[1.1.1]pentane inhibitors of dual leucine zipper (DLK) kinase for the treatment of disease |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4857641A (en) | 1987-08-14 | 1989-08-15 | Pfizer Inc. | C.12 modified erythromycin A derivatives |
| US6063561A (en) | 1991-01-17 | 2000-05-16 | Abbott Laboratories | Polyketide derivatives and recombinant methods for making same |
| FR2718450B1 (fr) | 1994-04-08 | 1997-01-10 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| FR2719587B1 (fr) | 1994-05-03 | 1996-07-12 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| US5750510A (en) | 1997-04-04 | 1998-05-12 | Abbott Laboratories | 3-descladinose-2,3-anhydroerythromycin derivatives |
| EP0918783A1 (en) | 1996-05-07 | 1999-06-02 | Abbott Laboratories | 6-o-substituted erythromycins and method for making them |
| UA51730C2 (uk) | 1996-09-04 | 2002-12-16 | Ебботт Лабораторіз | 6-o-заміщені кетоліди з антибактеріальною активністю, спосіб їх одержання (варіанти), фармацевтична композиція та спосіб регулювання бактеріальної інфекції у ссавців |
| DE69733439T2 (de) | 1996-09-04 | 2006-05-04 | Abbott Laboratories, Abbott Park | 6-o-Substituierte Ketoliden mit antibakteriellen Wirkung |
| US6191118B1 (en) | 1996-11-27 | 2001-02-20 | Taisho Pharmaceutical Co., Ltd. | Erythromycin A derivatives |
| AU6421398A (en) | 1997-03-24 | 1998-10-20 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a derivatives |
| US6124269A (en) | 1997-10-29 | 2000-09-26 | Abbott Laboratories | 2-Halo-6-O-substituted ketolide derivatives |
| AP1060A (en) | 1998-01-02 | 2002-04-23 | Pfizer Prod Inc | Novel erythromycin derivatives. |
| US6355620B1 (en) | 1999-05-14 | 2002-03-12 | Abbott Laboratories | C-2 modified erythromycin derivatives |
| WO2003004509A2 (en) | 2001-07-03 | 2003-01-16 | Chiron Corporation | C12 modified erythromycin macrolides and ketolides having antibacterial activity |
| US7332476B2 (en) * | 2003-04-25 | 2008-02-19 | Novartis Ag | Pyridyl substituted ketolide antibiotics |
-
2004
- 2004-04-23 EP EP04760380A patent/EP1618120A2/en not_active Withdrawn
- 2004-04-23 WO PCT/US2004/012778 patent/WO2004096823A2/en not_active Ceased
- 2004-04-23 CA CA002523541A patent/CA2523541A1/en not_active Abandoned
- 2004-04-23 US US10/831,522 patent/US7163924B2/en not_active Expired - Fee Related
- 2004-04-23 JP JP2006513319A patent/JP2006524706A/ja active Pending