WO2010002415A1 - Treatment of antibiotic-resistant bacteria infection - Google Patents
Treatment of antibiotic-resistant bacteria infection Download PDFInfo
- Publication number
- WO2010002415A1 WO2010002415A1 PCT/US2008/075549 US2008075549W WO2010002415A1 WO 2010002415 A1 WO2010002415 A1 WO 2010002415A1 US 2008075549 W US2008075549 W US 2008075549W WO 2010002415 A1 WO2010002415 A1 WO 2010002415A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- infection
- resistant
- compound
- staphylococcus aureus
- methicillin
- Prior art date
Links
- CKFRFTGDFFZNTM-CMDGGOBGSA-N CC(C)(C)OC(N(C(C/C1=C\N(C)C)C(OC)=O)C1=O)=O Chemical compound CC(C)(C)OC(N(C(C/C1=C\N(C)C)C(OC)=O)C1=O)=O CKFRFTGDFFZNTM-CMDGGOBGSA-N 0.000 description 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N OC(C(CC1)NC1=O)=O Chemical compound OC(C(CC1)NC1=O)=O ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
Definitions
- Antibiotic resistance in bacteria may be an inherent trait or may be acquired by mutation. Bacteria that are resistant to antibiotics become a serious public health threat.
- This invention relates to a method of treating infection caused by methicillin- nonsusceptibale bacteria, vancomycin-nonsusceptibale bacteria, penicillin- nonsusceptibale bacteria, clarithromycin-nonsusceptibale bacteria, or metronidazole- nonsusceptibale bacteria.
- the method includes administering to a subject an effective amount of one of the quinolone compounds of formula (I): formula (I)
- the compounds thus synthesized can be further purified by flash column chromatography, high performance liquid chromatography, crystallization, or any other suitable methods.
- nonsusceptible refers to resistance to a drug at the intermediate level through the full level.
- Methicillin-nonsusceptible bacteria include, but are not limited to, methicillin-resistant Staphylococcus aureus, efflux-related methicillin-resistant Staphylococcus aureus, community-associated methicillin- resistant Staphylococcus aureus, and methicillin-resistant Staphylococcus epidermidis.
- Vancomycin-nonsusceptible bacteria include, but are not limited to, hetero-vancomycin-intermediate Staphylococcus aureus, vancomycin-intermediate Staphylococcus aureus, and vancomycin-resistant Staphylococcus aureus.
- Penicillin- nonsusceptible bacteria include, but are not limited to, penicillin-resistant Streptococcus pneumoniae. Clarithromycin-nonsusceptible bacteria inlcude, but are not limited to, clarithromycin-resistant He/z ' c ⁇ & ⁇ ct ⁇ r pylori. Metronidazole- nonsusceptible bacteria inlcude, but are not limited to, metronidazole-resistant Helicobacter pylori.
- an effective amount refers to the amount of the active agent that is required to confer the intended therapeutic effect in the subject. Effective amounts may vary, as recognized by those skilled in the art, depending on route of administration, excipient usage, and the possibility of co-usage with other agents.
- treating refers to administering one of the above-described quinolone compounds to a subject that has the above-mentioned infection, or has a symptom of such infection, or has a predisposition toward such infection, with the purpose to cure, heal, alleviate, relieve, alter, remedy, ameliorate, improve, or affect the infection, the symptoms of the infection, or the predisposition toward the infection.
- the quinolone compounds can be administered orally, parenterally, by inhalation spray, or via an implanted reservoir.
- parenteral includes subcutaneous, intracutaneous, intravenous, intramuscular, intraarticular, intraarterial, intrasynovial, intrasternal, intrathecal, intralesional and intracranial injection or infusion techniques.
- a sterile injectable composition e.g., aqueous or oleaginous suspension
- suitable dispersing or wetting agents such as, for example, Tween 80
- the sterile injectable preparation can also be a sterile injectable solution or suspension in a nontoxic parenterally acceptable diluent or solvent, for example, as a solution in 1,3- butanediol.
- acceptable vehicles and solvents that can be employed are mannitol, water, Ringer's solution and isotonic sodium chloride solution.
- sterile, fixed oils are conventionally employed as a solvent or suspending medium (e g-, synthetic mono- or di-glycerides).
- Fatty acids such as oleic acid and its glyceride derivatives are useful in the preparation of injectables, as are natural pharmaceutically-acceptable oils, such as olive oil or castor oil, especially in their polyoxyethylated versions.
- oils such as olive oil or castor oil, especially in their polyoxyethylated versions.
- These oil solutions or suspensions can also contain a long-chain alcohol diluent or dispersant, or carboxymethyl cellulose or similar dispersing agents.
- a topical composition can be formulated in form of oil, cream, lotion, ointment and the like.
- suitable carriers for the composition include vegetable or mineral oils, white petrolatum (white soft paraffin), branched chain fats or oils, animal fats and high molecular weight alcohols (greater than C 12).
- the preferred carriers are those in which the active ingredient is soluble.
- Emulsif ⁇ ers, stabilizers, humectants and antioxidants may also be included as well as agents imparting color or fragrance, if desired.
- transdermal penetration enhancers may be employed in these topical formulations. Examples of such enhancers can be found in U.S. Patents 3,989,816 and 4,444,762.
- Creams are preferably formulated from a mixture of mineral oil, self-emulsifying beeswax and water in which mixture the active ingredient, dissolved in a small amount of oil, such as almond oil, is admixed.
- An example of such a cream is one which includes about 40 parts water, about 20 parts beeswax, about 40 parts mineral oil and about 1 part almond oil.
- Mixing a solution of the active ingredient in vegetable oil, such as almond oil, with warm soft paraffin and allowing the mixture to cool may formulate ointments.
- An example of such an ointment is one, which includes about 30% almond and about 70% white soft paraffin by weight.
- a carrier in a pharmaceutical composition must be "acceptable” in the sense that it is compatible with active ingredients of the formulation (and preferably, capable of stabilizing it) and not deleterious to the subject to be treated.
- solubilizing agents such as cyclodextrins (which form specific, more soluble complexes with one or more of active compounds of the extract), can be utilized as pharmaceutical excipients for delivery of the active ingredients.
- examples of other carriers include colloidal silicon dioxide, magnesium stearate, cellulose, sodium lauryl sulfate, and D&C Yellow # 10.
- a reactor was charged with 3.2 kg of Compound 12 and 25.6 kg of 95% ethanol. To the reactor was added 1.1 kg of solid D,L-malic acid. The mixture was refluxed temperature ( ⁇ 80°C). Distilled water (-5.7 L) was added to dissolve the precipice and 0.2 kg of activated charcoal was added. The reaction mixture was passed through a filter. The clear filtrate was cooled to 45°C and allowed to sit for at least 2 hours to allow crystallization. After the reaction mixture was further cooled to 5°C, the precipitate was isolated by suction filtration, washed with 6.6 kg of 95% ethanol, and dried with suction for at least 4 hours. The solid was further dried in a convection oven at 45 0 C for at least 12 hours to afford 3.1 kg of Compound 1 (yield: 70%).
- the table below shows MICs of Compound 1 and fluoroquinone antibiotics for inhibiting community-associated MRSA (CA-MRSA) strains-USA 300 and USA 400- and healthcare-associated MRSA strains-USA 200, USA 600, and USA 100/800.
- CA-MRSA community-associated MRSA
- Compound 1 effectively inhibited MRSA. It was also found that this compound was more active against community-associated-MRSA strains than healthcare-associated-MRSA strains.
- Compound 1 was tested for its inhibitory effect against 26 Methicillin-resistant Staphylococcus aureus (MRSA) strains, 2 hetero-Vancomycin intermediate Staphylococcus aureus (hVISA) strains, 24 Vancomycm-intermediate Staphylococcus aureus (VISA) strains, 5 Vancomycin-resistant Staphylococcus aureus (VRSA) strains, and 31 quinolone-resistant Vancomycin-susceptibale MRSA strains with defined mutations in QRDR. These mutations were determined by sequencing analysis of the QRDR (gyrA, gyrB, grlA, and grlB).
- Efflux testing was performed by the reserpine method (Brenwald, et al., Antimicrob. Agents Chemother. 1998, 42: 2032-2035). MICs were determined using the agar dilution methods recommended by the Clinical and Laboratory Standards Institute (CLSI-M100-S18) and are shown in the table below:
- NARSA Antimicrobial Resistance m Staphylococcus aureus
- clarithormycin MICs >1 ⁇ g/mL
- metronidazole MICs >8 ⁇ g/mL
- ciprofloxacin MICs >1 ⁇ g/mL
- levofloxan MICs >1 ⁇ g/mL
- the MIC range, MIC50, and MICgo of the five quinolone drugs tested are as follows: MIC (mg/niL)
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011516261A JP2011526887A (en) | 2008-07-01 | 2008-09-08 | Treatment of antibiotic-resistant bacterial infections |
KR1020147036073A KR20150006080A (en) | 2008-07-01 | 2008-09-08 | Treatment of antibiotic-resistant bacteria infection |
EA201170121A EA018653B1 (en) | 2008-07-01 | 2008-09-08 | Treatment of antibiotic-resistant bacteria infection |
NZ588898A NZ588898A (en) | 2008-07-01 | 2008-09-08 | Use of nemonoxacin for treating antibiotic-resistant staphylococcus aureus infection |
CA2728328A CA2728328C (en) | 2008-07-01 | 2008-09-08 | Treatment of antibiotic-resistant bacteria infection |
EP08821583.5A EP2303271B1 (en) | 2008-07-01 | 2008-09-08 | Treatment of antibiotic-resistant bacteria infection |
AU2008358909A AU2008358909B2 (en) | 2008-07-01 | 2008-09-08 | Treatment of antibiotic-resistant bacteria infection |
ZA2011/00616A ZA201100616B (en) | 2008-07-01 | 2011-01-25 | Treatment of antibiotic-resistant bacteria infection |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7729308P | 2008-07-01 | 2008-07-01 | |
US61/077,293 | 2008-07-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010002415A1 true WO2010002415A1 (en) | 2010-01-07 |
Family
ID=41464848
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2008/075549 WO2010002415A1 (en) | 2008-07-01 | 2008-09-08 | Treatment of antibiotic-resistant bacteria infection |
Country Status (14)
Country | Link |
---|---|
US (1) | US8211909B2 (en) |
EP (1) | EP2303271B1 (en) |
JP (1) | JP2011526887A (en) |
KR (2) | KR20150006080A (en) |
CN (1) | CN101618038B (en) |
AU (1) | AU2008358909B2 (en) |
CA (1) | CA2728328C (en) |
EA (1) | EA018653B1 (en) |
HK (1) | HK1139049A1 (en) |
NZ (1) | NZ588898A (en) |
TR (1) | TR201820964T4 (en) |
TW (1) | TWI375558B (en) |
WO (1) | WO2010002415A1 (en) |
ZA (1) | ZA201100616B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111979292A (en) * | 2020-07-27 | 2020-11-24 | 广东省微生物研究所(广东省微生物分析检测中心) | Application of MRSA (methicillin resistant staphylococcus aureus) simultaneously carrying multiple drug resistance genes cfr and lsa (E) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101392808B1 (en) * | 2011-12-30 | 2014-05-12 | 순천대학교 산학협력단 | Antibacterial compositions containing plant extracts or fractions |
CN103145615B (en) * | 2013-03-20 | 2015-07-29 | 浙江医药股份有限公司 | A kind of post-treating method of Nai Nuosha star inner complex |
KR101392810B1 (en) * | 2013-09-25 | 2014-05-12 | 순천대학교 산학협력단 | Antibacterial compositions containing plant extracts or fractions |
US9492374B2 (en) | 2015-03-25 | 2016-11-15 | Jose Rafael Salinas Andrade | Composition and method for treatment of ulcers |
CN105368825B (en) * | 2015-10-14 | 2019-09-10 | 华东医院 | Helicobacter pylori antibiotic resistance assay kit and Resistance detection method |
AU2018385789B2 (en) * | 2017-12-11 | 2024-02-15 | Denovamed Inc. | 5-(2,5-bis(4-chloro-2-isopropylphenyl)thiophen-3-yl)-1H-tetrazole for the topical treatment of bacterial infections |
Citations (4)
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---|---|---|---|---|
US100800A (en) | 1870-03-15 | Improvement in riding attachments for plows | ||
US3989816A (en) | 1975-06-19 | 1976-11-02 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacycloheptan-2-ones |
US4444762A (en) | 1980-04-04 | 1984-04-24 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacyclopentan-2-ones |
WO1999014214A1 (en) * | 1997-09-15 | 1999-03-25 | The Procter & Gamble Company | Antimicrobial quinolones, their compositions and uses |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6387928B1 (en) * | 1997-09-15 | 2002-05-14 | The Procter & Gamble Co. | Antimicrobial quinolones, their compositions and uses |
US6348624B1 (en) | 1998-01-09 | 2002-02-19 | The Procter & Gamble Co. | Process for making certain benzoic acid compounds |
HUP0303991A3 (en) | 2000-12-14 | 2012-09-28 | Warner Chilcott Company | Cyclization process step in the making of quinolones and naphthyridines |
US6900224B2 (en) * | 2002-07-31 | 2005-05-31 | The Procter & Gamble Company | Antimicrobial quinolones, their compositions and uses |
US6803469B2 (en) | 2002-08-05 | 2004-10-12 | The Procter & Gamble Company | Process for preparing quinolone antibiotic intermediates |
WO2005026145A2 (en) * | 2003-09-12 | 2005-03-24 | Warner-Lambert Company Llc | Quinolone antibacterial agents |
BRPI0709772B8 (en) * | 2006-03-28 | 2021-05-25 | The Protecter & Gamble Company | malate salts and polymorphs of (3s,5s)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid |
CA2647454A1 (en) | 2006-03-28 | 2007-10-04 | The Procter & Gamble Company | A coupling process for preparing quinolone intermediates |
US7528264B2 (en) | 2006-03-28 | 2009-05-05 | The Procter & Gamble Company | Hydride reduction process for preparing quinolone intermediates |
US8658183B2 (en) * | 2007-08-09 | 2014-02-25 | Taigen Biotechnology Company, Ltd. | Antimicrobial parenteral formulation |
JP2011528354A (en) * | 2008-07-15 | 2011-11-17 | タイゲン バイオテクノロジー カンパニー,リミテッド | Antibiotics |
-
2008
- 2008-09-08 US US12/206,060 patent/US8211909B2/en active Active
- 2008-09-08 TR TR2018/20964T patent/TR201820964T4/en unknown
- 2008-09-08 KR KR1020147036073A patent/KR20150006080A/en not_active Application Discontinuation
- 2008-09-08 NZ NZ588898A patent/NZ588898A/en unknown
- 2008-09-08 CA CA2728328A patent/CA2728328C/en active Active
- 2008-09-08 WO PCT/US2008/075549 patent/WO2010002415A1/en active Application Filing
- 2008-09-08 JP JP2011516261A patent/JP2011526887A/en active Pending
- 2008-09-08 EA EA201170121A patent/EA018653B1/en unknown
- 2008-09-08 KR KR1020107025547A patent/KR20110044168A/en not_active Application Discontinuation
- 2008-09-08 AU AU2008358909A patent/AU2008358909B2/en active Active
- 2008-09-08 EP EP08821583.5A patent/EP2303271B1/en active Active
- 2008-09-09 TW TW097134583A patent/TWI375558B/en active
- 2008-09-26 CN CN2008101700068A patent/CN101618038B/en active Active
-
2010
- 2010-05-17 HK HK10104822.4A patent/HK1139049A1/en unknown
-
2011
- 2011-01-25 ZA ZA2011/00616A patent/ZA201100616B/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US100800A (en) | 1870-03-15 | Improvement in riding attachments for plows | ||
US3989816A (en) | 1975-06-19 | 1976-11-02 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacycloheptan-2-ones |
US4444762A (en) | 1980-04-04 | 1984-04-24 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacyclopentan-2-ones |
WO1999014214A1 (en) * | 1997-09-15 | 1999-03-25 | The Procter & Gamble Company | Antimicrobial quinolones, their compositions and uses |
US6329391B1 (en) | 1997-09-15 | 2001-12-11 | The Procter & Gamble Co. | Antimicrobial quinolones, their compositions and uses |
Non-Patent Citations (14)
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"Encyclopedia of Reagents for Organic Synthesis", 1995, JOHN WILEY AND SONS |
BARRY, A.L. ET AL.: "In Vitro Activities of Three Nonfluorinated Quinolones against Representative Bacterial Isolates.", ANTIMICROBIAL AGENTS AND CHEMOTHERAPY., vol. 45, no. 6, 2001, pages 1923 - 1927, XP008140806 * |
BRENWALD ET AL., ANTIMICROB. AGENTS CHEMOTHER., vol. 42, 1998, pages 2032 - 2035 |
CHRISTIANSON ET AL., J CLIN MICROBIOL., vol. 45, no. 6, 2007, pages 1904 - 11 |
HU, X.E. ET AL.: "Discovery of(3S)-Amino-(4R)-ethylpiperodinyl Quinolones as Potent Antibacterial Agents with a Broad Spectrum ofActivity and Activity against Resistant Pathogens.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 46, no. 17, 2003, pages 3655 - 3661, XP008140805 * |
L. FIESER; M. FIESER: "Fieser and Fieser's Reagentsfor Organic Synthesis", 1994, JOHN WILEY AND SONS |
MULVEY ET AL., EMERG INFECT DIS., vol. 11, no. 6, 2005, pages 844 - 50 |
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R. LAROCK: "Comprehensive Organic Transformations", 1989, VCH PUBLISHERS |
ROYCHOUDHURY, S. ET AL.: "Activity of non-fluorinated quinolones (NFQs) against quinolone resistant Escherichia coli and Streptococcus pneumoniae.", JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY., vol. 48, no. 1, 2001, pages 29 - 36, XP008140804 * |
See also references of EP2303271A4 * |
T.W. GREENE; P.G.M. WUTS: "Protective Groups in Organic Synthesis", 1999, JOHN WILEY AND SONS |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111979292A (en) * | 2020-07-27 | 2020-11-24 | 广东省微生物研究所(广东省微生物分析检测中心) | Application of MRSA (methicillin resistant staphylococcus aureus) simultaneously carrying multiple drug resistance genes cfr and lsa (E) |
Also Published As
Publication number | Publication date |
---|---|
KR20150006080A (en) | 2015-01-15 |
EA201170121A1 (en) | 2011-06-30 |
CN101618038A (en) | 2010-01-06 |
EA018653B1 (en) | 2013-09-30 |
CA2728328A1 (en) | 2010-01-07 |
TW201002322A (en) | 2010-01-16 |
JP2011526887A (en) | 2011-10-20 |
ZA201100616B (en) | 2011-10-26 |
EP2303271A1 (en) | 2011-04-06 |
EP2303271A4 (en) | 2012-01-25 |
TR201820964T4 (en) | 2019-01-21 |
CA2728328C (en) | 2015-02-24 |
KR20110044168A (en) | 2011-04-28 |
NZ588898A (en) | 2012-09-28 |
TWI375558B (en) | 2012-11-01 |
AU2008358909B2 (en) | 2012-12-13 |
AU2008358909A1 (en) | 2010-01-07 |
HK1139049A1 (en) | 2010-09-10 |
US8211909B2 (en) | 2012-07-03 |
CN101618038B (en) | 2011-12-07 |
EP2303271B1 (en) | 2018-11-07 |
US20100004282A1 (en) | 2010-01-07 |
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