US20070155714A1 - Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections - Google Patents
Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections Download PDFInfo
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- US20070155714A1 US20070155714A1 US10/554,732 US55473204A US2007155714A1 US 20070155714 A1 US20070155714 A1 US 20070155714A1 US 55473204 A US55473204 A US 55473204A US 2007155714 A1 US2007155714 A1 US 2007155714A1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- alkenyl and alkinyl refer to an unsaturated straight or branched chain alkyl group (having one, two or more double and/or triple bonds, an alkenyl preferably having one or two double bonds and an alkinyl preferably having one or two triple bonds), containing from two to ten, preferably two to six carbon atoms for example: ethenyl (vinyl), propenyl (allyl), iso-propenyl, n-pentenyl, butenyl, isoprenyl or hexa-2-enyl; ethinyl, propinyl or butinyl groups.
- Any alkenyl or alkinyl group as defined herein may be substituted with one, two or more substituents, for example F, Cl, Br, I, NH 2 , OH, SH or NO 2 .
- compositions according to the present invention contain at least one compound of Formula (I), (II) or (III) as the active agent and optionally carriers and/or diluents and/or adjuvants.
- the pharmaceutical compositions according to the present invention may also contain additional known antibiotics.
- infection(s) As used herein, unless otherwise indicated, the terms or phrases “infection(s)”, “bacterial infection(s)”, “protozoal infection(s)”, and “disorders related to bacterial infections or protozoal infections” include the following: pneumonia, otitis media, sinusitus, bronchitis, tonsillitis, and mastoiditis related to infection by Streptococcus pneumoniae, Haemophilus influenzae, Moraxella catarrhalis, Staphylococcus aureus, Enterococcus faecalis, E. faecium, E. casselflavus, S. epidermidis, S.
- aureus food poisoning and toxic shock syndrome
- Groups A, B, and C streptococci ulcers related to infection by Helicobacter pylori ; systemic febrile syndromes related to infection by Borrelia recurrentis ; Lyme disease related to infection by Borrelia burgdorferi ; conjunctivitis, keratitis, and dacrocystitis related to infection by Chlamydia trachomatis, Neisseria gonorrhoeae, S. aureus, S. pneumoniae, S. pyogenes, H.
- Step 4 N-[(5S)- ⁇ 3-(3-fluoro-4-hydroxy-phenyl) ⁇ -2-oxo-oxazolidin-5-ylmethyl]-acetamide
- the dimethylformamide was evaporated under reduced pressure and the residue was dissolved in 600 ml of a 9:1 dichloromethane/methanol mixture.
- the organic layer was washed with 400 ml water and 400 ml brine.
- the organic layer was dried over magnesium sulfate, filtered, and the filtrate diluted with 250 ml ethyl acetate.
- the mixture was concentrated under reduced pressure to a final volume of 400 ml.
- the slurry was stirred at room temperature over night.
- the crystals were filtered and washed successively with 150 ml ethyl acetate and 100 ml pentane. Yield: 31.65 g, 76.7%.
- Step 2 7-(4- ⁇ 4-[(5S)-(5-Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl ⁇ -4-phosphonooxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
- the catalyst was filtered off using a glass fibre filter paper. The solvents were evaporated under reduced pressure and the residue dissolved in 10 ml methanol. The solution was diluted with 20 ml water while a white solid precipitated. The solid was collected and dried. Yield: 85 mg, 68%. MS: 709.0 (M+H) + , 706.5 (M ⁇ H) ⁇ Method ESI + , ESI ⁇ .
- Step 2 Succinic acid 4- ⁇ 4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl ⁇ -piperidin-4-yl ester benzyl ester
- Step 4 Succinic acid mono-[4- ⁇ 4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl ⁇ -1-(6-carboxy-8-cyclopropyl-3-fluoro-5-oxo-5,8-dihydro-[1,8]naphthyridin-2-yl)-piperidin-4-yl]ester
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/554,732 US20070155714A1 (en) | 2003-04-30 | 2004-04-06 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46694503P | 2003-04-30 | 2003-04-30 | |
| US53082203P | 2003-12-18 | 2003-12-18 | |
| PCT/EP2004/003650 WO2004096221A1 (en) | 2003-04-30 | 2004-04-06 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
| US10/554,732 US20070155714A1 (en) | 2003-04-30 | 2004-04-06 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2004/003650 A-371-Of-International WO2004096221A1 (en) | 2003-04-30 | 2004-04-06 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/987,611 Division US8268812B2 (en) | 2003-04-30 | 2011-01-10 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20070155714A1 true US20070155714A1 (en) | 2007-07-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/554,732 Abandoned US20070155714A1 (en) | 2003-04-30 | 2004-04-06 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
| US12/987,611 Expired - Lifetime US8268812B2 (en) | 2003-04-30 | 2011-01-10 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
| US13/596,700 Expired - Lifetime US8513231B2 (en) | 2003-04-30 | 2012-08-28 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/987,611 Expired - Lifetime US8268812B2 (en) | 2003-04-30 | 2011-01-10 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
| US13/596,700 Expired - Lifetime US8513231B2 (en) | 2003-04-30 | 2012-08-28 | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US20070155714A1 (ko) |
| EP (1) | EP1620098B1 (ko) |
| JP (2) | JP4805139B2 (ko) |
| KR (1) | KR101101982B1 (ko) |
| AT (1) | ATE397930T1 (ko) |
| AU (2) | AU2004233557B2 (ko) |
| BR (1) | BRPI0409955A (ko) |
| CA (1) | CA2529347C (ko) |
| DE (1) | DE602004014361D1 (ko) |
| ES (1) | ES2308171T3 (ko) |
| HK (1) | HK1078806A1 (ko) |
| IL (1) | IL171546A (ko) |
| MX (1) | MXPA05011654A (ko) |
| NZ (1) | NZ543757A (ko) |
| RU (1) | RU2351335C2 (ko) |
| WO (1) | WO2004096221A1 (ko) |
Cited By (4)
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| US20040132764A1 (en) * | 2002-10-23 | 2004-07-08 | Morphochem Aktiengesellschaft Fuer Kombinatorische Chemie | Antibiotics for the treatment of infections in acidic environments |
| US20050096343A1 (en) * | 2001-10-04 | 2005-05-05 | Christian Hubschwerlen | Dual action antibiotics |
| US20090281088A1 (en) * | 2008-03-26 | 2009-11-12 | Global Alliance For Tb Drug Development | Bicyclic nitroimidazole-substituted phenyl oxazolidinones |
| US20110263571A1 (en) * | 2008-10-27 | 2011-10-27 | Mitsubishi Tanabe Pharma Corporation | Novel amide derivative and use thereof as medicine |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2529347C (en) * | 2003-04-30 | 2011-09-06 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Use of oxazolidinone-quinoline hybrid antibiotics for the treatment of anthrax and other infections |
| DE10340485B4 (de) * | 2003-09-03 | 2015-05-13 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Verfahren zur Herstellung von Oxazolidinon-Chinolon Hybriden |
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| US8158797B2 (en) | 2003-12-18 | 2012-04-17 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Oxazolidinone-quinolone hybrid antibiotics |
| CN102816194A (zh) | 2004-02-27 | 2012-12-12 | 瑞伯-X医药品有限公司 | 大环化合物以及其制作和使用方法 |
| AR054608A1 (es) * | 2005-08-08 | 2007-06-27 | Actelion Pharmaceuticals Ltd | Derivados de oxazolidinona enlazados a quinolonas como antibacterianos |
| AU2007225088B2 (en) | 2006-03-13 | 2012-09-13 | Kyorin Pharmaceutical Co., Ltd | Aminoquinolones as GSK-3 inhibitors |
| JP5161070B2 (ja) | 2006-03-31 | 2013-03-13 | 財団法人乙卯研究所 | ヘテロ環を有する新規化合物 |
| US8124623B2 (en) | 2006-11-10 | 2012-02-28 | Actelion Pharmaceuticals Ltd. | 5-hydroxymethyl-oxazolidin-2-one-derivatives and their uses as antibacterials |
| PT2086968E (pt) * | 2006-11-10 | 2012-04-13 | Actelion Pharmaceuticals Ltd | Derivados de 5-hidroximetil-oxazolidin-2-ona |
| CL2007003332A1 (es) | 2006-11-24 | 2008-06-20 | Actelion Pharmaceuticals Ltd | Compuestos derivados de heterociclos condensados; compuestos intermediarios; composicion farmaceutica; y uso en la prevencion o tratamiento de infecciones bacterianas. |
| CA2699151A1 (en) | 2007-09-11 | 2009-03-19 | Activx Biosciences, Inc. | Cyanoaminoquinolones and tetrazoloaminoquinolones as gsk-3 inhibitors |
| CA2699152C (en) | 2007-09-12 | 2015-11-24 | Activx Biosciences, Inc. | Spirocyclic aminoquinolones as gsk-3 inhibitors |
| EP2669283A1 (en) | 2007-10-02 | 2013-12-04 | Shionogi&Co., Ltd. | Oxazolidinone derivative having 7-membered hetero ring |
| FR2928150A1 (fr) | 2008-02-29 | 2009-09-04 | Vetoquinol Sa Sa | Nouveaux derives 7-substitues de 3-carboxy-oxadiazino-quinolones, leur preparation et leur application comme anti-bacteriens |
| TWI447115B (zh) * | 2008-05-09 | 2014-08-01 | Actelion Pharmaceuticals Ltd | 用於治療細菌性腸疾病之５－羥基甲基－唑啶－２－酮衍生物 |
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| MX2011009414A (es) | 2009-03-11 | 2011-10-19 | Kyorin Seiyaku Kk | 7-cicloalquiloaminoquinolonas como inhibidores de gsk-3. |
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- 2004-04-06 CA CA2529347A patent/CA2529347C/en not_active Expired - Lifetime
- 2004-04-06 US US10/554,732 patent/US20070155714A1/en not_active Abandoned
- 2004-04-06 RU RU2005137032/15A patent/RU2351335C2/ru active
- 2004-04-06 DE DE602004014361T patent/DE602004014361D1/de not_active Expired - Lifetime
- 2004-04-06 MX MXPA05011654A patent/MXPA05011654A/es active IP Right Grant
- 2004-04-06 BR BRPI0409955-9A patent/BRPI0409955A/pt not_active Application Discontinuation
- 2004-04-06 ES ES04725909T patent/ES2308171T3/es not_active Expired - Lifetime
- 2004-04-06 KR KR1020057020656A patent/KR101101982B1/ko active IP Right Grant
- 2004-04-06 AU AU2004233557A patent/AU2004233557B2/en not_active Ceased
- 2004-04-06 EP EP04725909A patent/EP1620098B1/en not_active Expired - Lifetime
- 2004-04-06 NZ NZ543757A patent/NZ543757A/en not_active IP Right Cessation
- 2004-04-06 AT AT04725909T patent/ATE397930T1/de not_active IP Right Cessation
- 2004-04-06 JP JP2006505018A patent/JP4805139B2/ja not_active Expired - Lifetime
- 2004-04-06 WO PCT/EP2004/003650 patent/WO2004096221A1/en active IP Right Grant
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2005
- 2005-10-23 IL IL171546A patent/IL171546A/en not_active IP Right Cessation
-
2006
- 2006-02-08 HK HK06101647A patent/HK1078806A1/xx not_active IP Right Cessation
-
2010
- 2010-04-27 AU AU2010201659A patent/AU2010201659A1/en not_active Abandoned
-
2011
- 2011-01-10 US US12/987,611 patent/US8268812B2/en not_active Expired - Lifetime
- 2011-04-04 JP JP2011082360A patent/JP5536706B2/ja not_active Expired - Fee Related
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2012
- 2012-08-28 US US13/596,700 patent/US8513231B2/en not_active Expired - Lifetime
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050096343A1 (en) * | 2001-10-04 | 2005-05-05 | Christian Hubschwerlen | Dual action antibiotics |
| US7820823B2 (en) | 2001-10-04 | 2010-10-26 | Morphochem Aktiengesellschaft Fur Kominatorische Chemi | Dual action antibiotics |
| US8329908B2 (en) | 2001-10-04 | 2012-12-11 | Morphochem Aktiengesellschaft Fur Kombinatorische Chemie | Dual action antibiotics |
| US20040132764A1 (en) * | 2002-10-23 | 2004-07-08 | Morphochem Aktiengesellschaft Fuer Kombinatorische Chemie | Antibiotics for the treatment of infections in acidic environments |
| US20090281088A1 (en) * | 2008-03-26 | 2009-11-12 | Global Alliance For Tb Drug Development | Bicyclic nitroimidazole-substituted phenyl oxazolidinones |
| US7666864B2 (en) | 2008-03-26 | 2010-02-23 | Global Alliance For Tb Drug Development | Bicyclic nitroimidazole-substituted phenyl oxazolidinones |
| US20110263571A1 (en) * | 2008-10-27 | 2011-10-27 | Mitsubishi Tanabe Pharma Corporation | Novel amide derivative and use thereof as medicine |
| US8354401B2 (en) * | 2008-10-27 | 2013-01-15 | Mitsubishi Tanabe Pharma Corporation | Oxazolidinone amide aromatic compounds for supressing MMP-9 production |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE397930T1 (de) | 2008-07-15 |
| US20120322766A1 (en) | 2012-12-20 |
| WO2004096221A1 (en) | 2004-11-11 |
| KR20060025525A (ko) | 2006-03-21 |
| EP1620098B1 (en) | 2008-06-11 |
| HK1078806A1 (en) | 2006-03-24 |
| US20120135961A1 (en) | 2012-05-31 |
| CA2529347A1 (en) | 2004-11-11 |
| AU2004233557B2 (en) | 2010-02-18 |
| AU2010201659A1 (en) | 2010-05-20 |
| RU2005137032A (ru) | 2007-06-10 |
| JP2011184441A (ja) | 2011-09-22 |
| NZ543757A (en) | 2009-02-28 |
| DE602004014361D1 (de) | 2008-07-24 |
| JP2006526577A (ja) | 2006-11-24 |
| BRPI0409955A (pt) | 2006-04-25 |
| US8268812B2 (en) | 2012-09-18 |
| RU2351335C2 (ru) | 2009-04-10 |
| AU2004233557A1 (en) | 2004-11-11 |
| EP1620098A1 (en) | 2006-02-01 |
| KR101101982B1 (ko) | 2012-01-02 |
| ES2308171T3 (es) | 2008-12-01 |
| JP5536706B2 (ja) | 2014-07-02 |
| US8513231B2 (en) | 2013-08-20 |
| JP4805139B2 (ja) | 2011-11-02 |
| MXPA05011654A (es) | 2005-12-15 |
| IL171546A (en) | 2014-06-30 |
| CA2529347C (en) | 2011-09-06 |
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