AU2013365769B2 - Antimicrobial compounds, their synthesis and applications thereof - Google Patents
Antimicrobial compounds, their synthesis and applications thereof Download PDFInfo
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- AU2013365769B2 AU2013365769B2 AU2013365769A AU2013365769A AU2013365769B2 AU 2013365769 B2 AU2013365769 B2 AU 2013365769B2 AU 2013365769 A AU2013365769 A AU 2013365769A AU 2013365769 A AU2013365769 A AU 2013365769A AU 2013365769 B2 AU2013365769 B2 AU 2013365769B2
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- 238000007911 parenteral administration Methods 0.000 description 1
- 150000002959 penams Chemical class 0.000 description 1
- 150000002961 penems Chemical class 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000003156 secondary amide group Chemical group 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000006283 soil fumigant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003588 threonines Chemical class 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229930003802 tocotrienol Natural products 0.000 description 1
- 239000011731 tocotrienol Substances 0.000 description 1
- 235000019148 tocotrienols Nutrition 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/05—Dipeptides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN5299/CHE/2012 | 2012-12-18 | ||
| IN5299CH2012 | 2012-12-18 | ||
| PCT/IB2013/061090 WO2014097178A1 (en) | 2012-12-18 | 2013-12-18 | Antimicrobial compounds, their synthesis and applications thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2013365769A1 AU2013365769A1 (en) | 2015-07-02 |
| AU2013365769B2 true AU2013365769B2 (en) | 2018-03-15 |
Family
ID=54148251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013365769A Ceased AU2013365769B2 (en) | 2012-12-18 | 2013-12-18 | Antimicrobial compounds, their synthesis and applications thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9783490B2 (https=) |
| EP (1) | EP2934563B1 (https=) |
| JP (1) | JP6533466B2 (https=) |
| CN (1) | CN104981249B (https=) |
| AU (1) | AU2013365769B2 (https=) |
| BR (1) | BR112015014391B1 (https=) |
| CA (1) | CA2894202A1 (https=) |
| HK (1) | HK1210437A1 (https=) |
| WO (1) | WO2014097178A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566149B (zh) * | 2016-03-02 | 2017-05-24 | 郑州大学 | 具有抗菌活性的查尔酮阳离子抗菌肽模拟物及其制备方法 |
| CN106995384B (zh) * | 2017-04-21 | 2018-12-11 | 郑州大学 | 具有抗菌活性的二烷基阳离子两亲性抗菌肽模拟物及其制备方法 |
| US20200354413A1 (en) | 2017-12-15 | 2020-11-12 | Dana-Farber Cancer Institute, Inc. | Stabilized peptide-mediated targeted protein degradation |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995017888A1 (en) * | 1993-12-30 | 1995-07-06 | Smithkline Beecham Corporation | Phenylmethyl hexanamides, and the use thereof |
| WO2007129952A1 (en) * | 2006-05-09 | 2007-11-15 | Neobiotics Ab | Novel peptide derivatives useful as antimicrobial agents for treating wounds |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59309867D1 (de) | 1992-09-03 | 1999-12-16 | Boehringer Ingelheim Pharma | Neue aminosäurederivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen |
| US5654451B1 (en) * | 1993-01-14 | 2000-02-22 | Magainin Pharma | Amino acids and peptides having modified c-terminals and modified n-terminals |
| US5663148A (en) | 1994-07-12 | 1997-09-02 | Abbott Laboratories | Anaphylatoxin receptor ligands containing lipophilic residues |
| US6071890A (en) * | 1994-12-09 | 2000-06-06 | Genzyme Corporation | Organ-specific targeting of cationic amphiphile/DNA complexes for gene therapy |
| DE69612962T2 (de) * | 1995-12-12 | 2001-11-15 | Taiho Pharmaceutical Co. Ltd., Tokio/Tokyo | Epoxysuccinamid-derivate oder deren salze und medikamente die diese enthalten |
| CA2217550A1 (en) * | 1996-10-22 | 1998-04-22 | F. Hoffmann-La Roche Ag | Cationic lipids for gene therapy |
| BR9813554A (pt) * | 1997-12-12 | 2001-07-24 | Fuji Yakuhin Kogyo Kk | Composto, uso do mesmo, processo para produzi-lo, composição farmacêutica ou veterinária, e, inibidor de metaloproteinase |
| WO2001040198A2 (fr) * | 1999-11-30 | 2001-06-07 | Aventis Pharma S.A. | Derives macrocycliques de l'acide hydroxamique et leur utilisation en tant qu'antimicrobiens |
| JP2002161084A (ja) * | 2000-11-28 | 2002-06-04 | Sumitomo Pharmaceut Co Ltd | 複素環誘導体 |
| US7393836B2 (en) | 2004-07-06 | 2008-07-01 | Boehringer Ingelheim International Gmbh | D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture |
| GB0512751D0 (en) * | 2005-06-22 | 2005-07-27 | Glaxo Group Ltd | New adjuvant |
| AU2007304847A1 (en) * | 2006-10-04 | 2008-04-10 | Inimex Pharmaceuticals, Inc. | Novel peptides for treating and preventing immune-related disorders, including treating and preventing infection by modulating innate immunity |
| EP2091917A1 (en) * | 2006-12-11 | 2009-08-26 | Wyeth a Corporation of the State of Delaware | Ion channel modulators |
| CN102757477B (zh) * | 2011-04-27 | 2014-09-03 | 首都医科大学 | 烯丙基半胱氨酰氨基酸甲酯衍生物及其合成方法和应用 |
| EP2709619B1 (en) * | 2011-05-16 | 2017-10-11 | Cellceutix Corporation | Compounds for use in treatment of mucositis |
-
2013
- 2013-12-18 CN CN201380070984.4A patent/CN104981249B/zh not_active Expired - Fee Related
- 2013-12-18 AU AU2013365769A patent/AU2013365769B2/en not_active Ceased
- 2013-12-18 WO PCT/IB2013/061090 patent/WO2014097178A1/en not_active Ceased
- 2013-12-18 HK HK15111327.4A patent/HK1210437A1/xx unknown
- 2013-12-18 CA CA2894202A patent/CA2894202A1/en not_active Abandoned
- 2013-12-18 BR BR112015014391-1A patent/BR112015014391B1/pt not_active IP Right Cessation
- 2013-12-18 EP EP13865950.3A patent/EP2934563B1/en active Active
- 2013-12-18 JP JP2015548841A patent/JP6533466B2/ja not_active Expired - Fee Related
- 2013-12-18 US US14/652,714 patent/US9783490B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995017888A1 (en) * | 1993-12-30 | 1995-07-06 | Smithkline Beecham Corporation | Phenylmethyl hexanamides, and the use thereof |
| WO2007129952A1 (en) * | 2006-05-09 | 2007-11-15 | Neobiotics Ab | Novel peptide derivatives useful as antimicrobial agents for treating wounds |
Non-Patent Citations (1)
| Title |
|---|
| SVENSON JOHAN ET AL, JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 50, no. 14, doi:10.1021/JM0703542, ISSN 0022-2623, (2007-07-12), pages 3334 - 3339, (2007-06-15) * |
Also Published As
| Publication number | Publication date |
|---|---|
| US9783490B2 (en) | 2017-10-10 |
| CA2894202A1 (en) | 2014-06-26 |
| CN104981249B (zh) | 2018-06-19 |
| JP6533466B2 (ja) | 2019-06-19 |
| US20150329478A1 (en) | 2015-11-19 |
| EP2934563A1 (en) | 2015-10-28 |
| EP2934563B1 (en) | 2020-07-08 |
| BR112015014391A2 (pt) | 2017-07-11 |
| WO2014097178A1 (en) | 2014-06-26 |
| CN104981249A (zh) | 2015-10-14 |
| AU2013365769A1 (en) | 2015-07-02 |
| JP2016504330A (ja) | 2016-02-12 |
| BR112015014391B1 (pt) | 2020-11-03 |
| HK1210437A1 (en) | 2016-04-22 |
| EP2934563A4 (en) | 2016-08-17 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |