TWI629277B - 抗微生物性化合物,及製法及其用途 - Google Patents
抗微生物性化合物,及製法及其用途 Download PDFInfo
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- TWI629277B TWI629277B TW106102658A TW106102658A TWI629277B TW I629277 B TWI629277 B TW I629277B TW 106102658 A TW106102658 A TW 106102658A TW 106102658 A TW106102658 A TW 106102658A TW I629277 B TWI629277 B TW I629277B
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- unsaturated
- alkyl
- membered saturated
- compound
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Classifications
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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CN104628729B (zh) * | 2009-10-16 | 2018-11-06 | 梅琳塔治疗公司 | 抗微生物化合物和其制备和使用方法 |
BR112012008759A2 (pt) | 2009-10-16 | 2020-08-25 | Rib-X Pharmaceuticals, Inc. | compostos antimicrobianos e métodos de fabricação e uso dos mesmos |
EP2488502A4 (en) | 2009-10-16 | 2013-05-15 | Rib X Pharmaceuticals Inc | ANTIMICROBIAL COMPOUNDS AND METHOD FOR THEIR PREPARATION AND USE |
CN103958514B (zh) * | 2011-04-15 | 2018-07-03 | 梅琳塔治疗公司 | 抗微生物化合物及制备和使用所述化合物的方法 |
MX2016002975A (es) | 2013-09-09 | 2016-10-21 | Melinta Therapeutics Inc | Compuestos antimicrobianos y métodos de fabricación y utilización de los mismos. |
JP2016529325A (ja) | 2013-09-09 | 2016-09-23 | メリンタ セラピューティクス,インコーポレイテッド | 抗微生物化合物ならびにそれの製造方法および使用方法 |
EA201792006A1 (ru) | 2015-03-11 | 2018-04-30 | Мелинта Терапьютикс, Инк. | Антимикробные соединения и способы их получения и их применение |
EP3452479A1 (en) | 2016-05-06 | 2019-03-13 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004080466A1 (en) * | 2003-03-07 | 2004-09-23 | Ribapharm Inc. | Cytidine analogs and methods of use |
WO2009113828A2 (en) * | 2008-03-14 | 2009-09-17 | Cti Bio | Peptide nucleic acid derivatives with good cell penetration and strong affinity for nucleic acid |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3980781A (en) * | 1966-03-31 | 1976-09-14 | Imperial Chemical Industries Limited | Fungicidal composition and method containing 2-amino-pyrimidines |
US3673184A (en) * | 1970-09-02 | 1972-06-27 | Dainippon Pharmaceutical Co | Certain 2-substituted-5,8-dihydro-5-oxopyrido{8 2,3-d{9 pyrimidine-6-carboxylic acid derivatives |
EP0067610A1 (en) * | 1981-06-16 | 1982-12-22 | Beecham Group Plc | Penicillins, a process for their preparation and compositions containing them |
ZA835684B (en) * | 1982-08-27 | 1985-03-27 | Roussel Uclaf | Imidazo(1,2-a)pyrimidines |
IT1197876B (it) * | 1986-10-15 | 1988-12-21 | Pharmachim Engineering Srl | Procedimento per la preparazione dell'acido 5,8-diidro-8-etil-5-osso-2-(1-piperazinil)pirido(2,3-d)pirimidin-6-carbossilico |
JP2549931B2 (ja) * | 1990-01-12 | 1996-10-30 | 株式会社大塚製薬工場 | ピリミドベンズイミダゾール誘導体 |
JP2991382B2 (ja) * | 1990-07-18 | 1999-12-20 | 大日本製薬株式会社 | 縮合三環式化合物およびその塩 |
JP2811230B2 (ja) * | 1990-10-17 | 1998-10-15 | コニカ株式会社 | 新規な写真用カプラー |
US5208141A (en) * | 1990-10-09 | 1993-05-04 | Konica Corporation | Silver halide color photographic light-sensitive material |
US6451968B1 (en) * | 1991-05-24 | 2002-09-17 | Isis Pharmaceuticals, Inc. | Peptide nucleic acids |
US5434257A (en) * | 1992-06-01 | 1995-07-18 | Gilead Sciences, Inc. | Binding compentent oligomers containing unsaturated 3',5' and 2',5' linkages |
US5646163A (en) * | 1992-10-30 | 1997-07-08 | The Procter & Gamble Company | Quinolone 5-(N-heterosubstituted amino) antimicrobials |
IT1263804B (it) * | 1993-01-22 | 1996-09-03 | Luso Farmaco Inst | Derivati pirimidinonici fusi con eterocicli azotati ad attivita' a ii antagonista |
CZ291264B6 (cs) * | 1993-05-12 | 2003-01-15 | E.I. Du Pont De Nemours And Company | Kondenzované bicyklické pyrimidinony, fungicidní prostředek a způsob potlačování padlí travního |
US5502177A (en) * | 1993-09-17 | 1996-03-26 | Gilead Sciences, Inc. | Pyrimidine derivatives for labeled binding partners |
US5668127A (en) * | 1995-06-26 | 1997-09-16 | Pathogenesis Corporation | Nitroimidazole antibacterial compounds and methods of use thereof |
CA2309340C (en) * | 1997-11-07 | 2006-02-21 | Isis Pharmaceuticals Inc. | Pyrimidine derivatives for labeled binding partners |
DE19838998A1 (de) * | 1998-08-27 | 2000-03-09 | Bayer Ag | Neue Naturstoffderivate |
SE9903894D0 (sv) * | 1999-10-28 | 1999-10-28 | New Pharma Research Ab | Novel compounds |
PT1411954E (pt) * | 2000-10-18 | 2011-03-16 | Pharmasset Inc | Nucleosídeos modificados para o tratamento de infecções virais e proliferação celular anormal |
DE10061542A1 (de) * | 2000-12-11 | 2002-06-13 | Bayer Ag | Alkanoylamino-pyrimidine |
DE10061538A1 (de) * | 2000-12-11 | 2002-06-20 | Bayer Ag | Ureido-Dihydropyrimidinone |
HUP0303410A3 (en) * | 2000-12-14 | 2005-12-28 | Procter & Gamble | Antimicrobial quinolones, pharmaceutical compositions containing them and their use |
ATE465739T1 (de) * | 2001-01-29 | 2010-05-15 | Bio Rad Laboratories | Nukleinsäurederivative |
TWI248936B (en) * | 2001-03-21 | 2006-02-11 | Merck Sharp & Dohme | Imidazo-pyrimidine derivatives as ligands for GABA receptors |
WO2002097134A2 (en) * | 2001-05-25 | 2002-12-05 | Isis Pharmaceuticals, Inc. | Modified peptide nucleic acid |
CA2452458A1 (en) * | 2001-07-03 | 2003-01-16 | Isis Pharmaceuticals, Inc. | Nuclease resistant chimeric oligonucleotides |
JP4306206B2 (ja) * | 2001-09-04 | 2009-07-29 | 住友化学株式会社 | イミダゾ[1,2−a]ピリミジン、その用途およびその製造中間体 |
GB0205165D0 (en) * | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
KR20060069836A (ko) * | 2003-08-12 | 2006-06-22 | 아칠리온 파르마세우티칼스 인코포레이티드 | 항-감염제로서의 이소티아졸로퀴놀론 및 관련 화합물 |
KR101272263B1 (ko) * | 2005-07-27 | 2013-06-13 | 아칠리온 파르마세우티칼스 인코포레이티드 | 감염 방지제로서 사용되는8-메톡시-9h-이소티아졸로[5,4-b]퀴놀린-3,4-디온 및관련 화합물 |
WO2007101871A1 (de) * | 2006-03-08 | 2007-09-13 | Basf Se | Substituierte imidazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
US20100112561A1 (en) * | 2006-08-25 | 2010-05-06 | Stefan Lutz | Fluorescent nucleoside analogues |
EP1964841A1 (en) * | 2007-02-28 | 2008-09-03 | sanofi-aventis | Imidazo[1,2-a]azine and their use as pharmaceuticals |
CN104628729B (zh) * | 2009-10-16 | 2018-11-06 | 梅琳塔治疗公司 | 抗微生物化合物和其制备和使用方法 |
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004080466A1 (en) * | 2003-03-07 | 2004-09-23 | Ribapharm Inc. | Cytidine analogs and methods of use |
WO2009113828A2 (en) * | 2008-03-14 | 2009-09-17 | Cti Bio | Peptide nucleic acid derivatives with good cell penetration and strong affinity for nucleic acid |
Non-Patent Citations (3)
Title |
---|
Janeba Zlatko et al.;"Synthesis and Biological Evaluation of Acyclic 3-[(2-Hydroxyethoxy)methyl]Analogues of Antiviral Furo- and Pyrrolo[2,3-d]pyrimidine Nucleosides";Journal of Medicinal Chemistry,2005,vol.48,pages 4690-4696. |
Janeba Zlatko et al.;"Synthesis and Biological Evaluation of Acyclic 3-[(2-Hydroxyethoxy)methyl]Analogues of Antiviral Furo- and Pyrrolo[2,3-d]pyrimidine Nucleosides";Journal of Medicinal Chemistry,2005,vol.48,pages 4690-4696. Wojciechowski Filip et al.;"Peptide Nucleic Acid Containing a Meta-Substituted Phenylpyrrolocytosine Exhibits a Fluorescence Response and Increased Binding Affinity toward RNA";Organic Letters,2009,vol.11,no.21,pages 4878-4881. * |
Wojciechowski Filip et al.;"Peptide Nucleic Acid Containing a Meta-Substituted Phenylpyrrolocytosine Exhibits a Fluorescence Response and Increased Binding Affinity toward RNA";Organic Letters,2009,vol.11,no.21,pages 4878-4881. |
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