JP5373393B2 - ヒドロキシアミノ基またはアシルオキシアミノシクロアルキル基を含むプレウロムチリン誘導体 - Google Patents
ヒドロキシアミノ基またはアシルオキシアミノシクロアルキル基を含むプレウロムチリン誘導体 Download PDFInfo
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- JP5373393B2 JP5373393B2 JP2008518554A JP2008518554A JP5373393B2 JP 5373393 B2 JP5373393 B2 JP 5373393B2 JP 2008518554 A JP2008518554 A JP 2008518554A JP 2008518554 A JP2008518554 A JP 2008518554A JP 5373393 B2 JP5373393 B2 JP 5373393B2
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- Prior art keywords
- mutilin
- amino
- acetyl
- cycloalkyl
- hydroxy
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- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 title claims description 32
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical class C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 title description 7
- 229960002771 retapamulin Drugs 0.000 claims abstract description 138
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- STZYTFJPGGDRJD-NHUWBDDWSA-N retapamulin Chemical compound C([C@H]([C@@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CS[C@@H]3C[C@H]4CC[C@H](N4C)C3)C)C[C@]32[C@H]1C(=O)CC3 STZYTFJPGGDRJD-NHUWBDDWSA-N 0.000 claims abstract description 8
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 7
- OBUUFWIMEGVAQS-UHFFFAOYSA-N Pleuromutenol Natural products CC1C(O)C(C)(C=C)CC(O)C2(C)C(C)CCC31C2C(=O)CC3 OBUUFWIMEGVAQS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
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- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- XZNONKDSWHVKCF-UHFFFAOYSA-N 2-[3-(2-methylpropanoyloxyamino)cyclohexyl]sulfanylacetic acid Chemical compound CC(C)C(=O)ONC1CCCC(SCC(O)=O)C1 XZNONKDSWHVKCF-UHFFFAOYSA-N 0.000 claims description 2
- OFCKRECIZRHXHW-UHFFFAOYSA-N 2-[3-(acetyloxyamino)cyclohexyl]sulfanylacetic acid Chemical compound CC(=O)ONC1CCCC(SCC(O)=O)C1 OFCKRECIZRHXHW-UHFFFAOYSA-N 0.000 claims description 2
- KDAUXTOIDWPFSZ-UHFFFAOYSA-N 2-[3-(hydroxyamino)cyclohexyl]sulfanylacetic acid Chemical compound ONC1CCCC(SCC(O)=O)C1 KDAUXTOIDWPFSZ-UHFFFAOYSA-N 0.000 claims description 2
- MFTWJCTURNOFDW-UHFFFAOYSA-N 2-[3-(hydroxyamino)cyclopentyl]sulfanylacetic acid Chemical compound ONC1CCC(SCC(O)=O)C1 MFTWJCTURNOFDW-UHFFFAOYSA-N 0.000 claims description 2
- WUYBWQYPYSVHRL-UHFFFAOYSA-N 2-[3-[acetyl(acetyloxy)amino]cyclohexyl]sulfanylacetic acid Chemical compound CC(=O)ON(C(C)=O)C1CCCC(SCC(O)=O)C1 WUYBWQYPYSVHRL-UHFFFAOYSA-N 0.000 claims description 2
- FPWCUFLIYCMVIO-UHFFFAOYSA-N 2-[3-[formyl(hydroxy)amino]cyclohexyl]sulfanylacetic acid Chemical compound O=CN(O)C1CCCC(SCC(O)=O)C1 FPWCUFLIYCMVIO-UHFFFAOYSA-N 0.000 claims description 2
- HNLHYCWDBQHCAX-UHFFFAOYSA-N 2-[3-[formyl(hydroxy)amino]cyclopentyl]sulfanylacetic acid Chemical compound O=CN(O)C1CCC(SCC(O)=O)C1 HNLHYCWDBQHCAX-UHFFFAOYSA-N 0.000 claims description 2
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- 238000011200 topical administration Methods 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/95—Spiro compounds containing "not free" spiro atoms
- C07C2603/98—Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members
- C07C2603/99—Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members containing eight-membered rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0513060.4 | 2005-06-27 | ||
| GB0513060A GB0513060D0 (en) | 2005-06-27 | 2005-06-27 | Organic compounds |
| GB0515997.5 | 2005-08-03 | ||
| GB0515997A GB0515997D0 (en) | 2005-08-03 | 2005-08-03 | Organic compounds |
| PCT/AT2006/000260 WO2007000004A1 (en) | 2005-06-27 | 2006-06-26 | Pleuromutilin derivatives containing a hydroxyamino- or acyloxyaminocycloalkyl group |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008546810A JP2008546810A (ja) | 2008-12-25 |
| JP2008546810A5 JP2008546810A5 (enExample) | 2012-10-25 |
| JP5373393B2 true JP5373393B2 (ja) | 2013-12-18 |
Family
ID=36764461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008518554A Expired - Fee Related JP5373393B2 (ja) | 2005-06-27 | 2006-06-26 | ヒドロキシアミノ基またはアシルオキシアミノシクロアルキル基を含むプレウロムチリン誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7790767B2 (enExample) |
| EP (2) | EP1896404B1 (enExample) |
| JP (1) | JP5373393B2 (enExample) |
| TW (1) | TW200730488A (enExample) |
| WO (1) | WO2007000004A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1896404B1 (en) * | 2005-06-27 | 2014-09-17 | Nabriva Therapeutics AG | Pleuromutilin derivatives containing a hydroxyamino- or acyloxyaminocycloalkyl group |
| EP1808431A1 (en) | 2006-01-16 | 2007-07-18 | Nabriva Therapeutics Forschungs GmbH | Mutilin derivatives and their use as pharmaceutical |
| EP1972618A1 (en) | 2007-03-20 | 2008-09-24 | Nabriva Therapeutics AG | Pleuromutilin derivatives for the treatment of diseases mediated by microbes |
| EP2149571A4 (en) | 2007-05-24 | 2010-09-01 | Kyorin Seiyaku Kk | MUTILINE DERIVATIVE WITH A RINGED, HETEROCYCLIC AND AROMATIC CARBOXYLIC ACID STRUCTURE IN A SUBSTITUTE AT POSITION 14 |
| EP2159220A1 (en) * | 2008-09-02 | 2010-03-03 | Nabriva Therapeutics AG | Organic compounds |
| AR090010A1 (es) | 2011-04-15 | 2014-10-15 | Bayer Cropscience Ag | 5-(ciclohex-2-en-1-il)-penta-2,4-dienos y 5-(ciclohex-2-en-1-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas, usos y metodos de tratamiento |
| CN102229580B (zh) * | 2011-05-12 | 2014-02-26 | 南通大学 | 新型截短侧耳素衍生物、其制备方法及其医药用途 |
| US9173395B2 (en) | 2011-07-04 | 2015-11-03 | Bayer Intellectual Property Gmbh | Use of substituted isoquinolinones, isoquinolindiones, isoquinolintriones and dihydroisoquinolinones or in each case salts thereof as active agents against abiotic stress in plants |
| CN103204787B (zh) * | 2012-01-17 | 2014-10-01 | 北京艾百诺科技有限公司 | 含有取代方酸的乙酸妙林酯及其应用 |
| CN105916499B (zh) * | 2014-01-22 | 2020-02-18 | 纳布里瓦治疗股份公司 | 12-表-截短侧耳素 |
| JP6818019B2 (ja) | 2015-06-17 | 2021-01-20 | ナブリヴァ セラピュティクス ゲーエムベーハー | レファムリンの注射可能医薬組成物 |
| TWI762573B (zh) | 2017-02-10 | 2022-05-01 | 奧地利商納畢瓦治療有限責任公司 | 截短側耳素之純化 |
| IL297268A (en) * | 2020-04-17 | 2022-12-01 | Nabriva Therapeutics GmbH | Therapeutic use of pleuromutilins |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3054875B2 (ja) * | 1995-02-13 | 2000-06-19 | 株式会社小松製作所 | プラズマトーチ |
| UY25225A1 (es) * | 1997-10-29 | 2000-12-29 | Smithkline Beecham Plc | Derivados de pleuromutilina utiles como agentes antimicrobianos |
| CO5150194A1 (es) * | 1999-01-27 | 2002-04-29 | Abbott Lab | Inhibidores hidroxamato inversos de las metalopreteinasas matriciales |
| GB0017031D0 (en) * | 2000-07-11 | 2000-08-30 | Biochemie Gmbh | Antimicrobials |
| US20030212056A1 (en) * | 2001-11-02 | 2003-11-13 | Jingwu Duan | Beta-sulfone derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE) |
| GB0207495D0 (en) * | 2002-03-28 | 2002-05-08 | Biochemie Gmbh | Organic compounds |
| GB0209262D0 (en) * | 2002-04-23 | 2002-06-05 | Biochemie Gmbh | Organic compounds |
| EP1896404B1 (en) * | 2005-06-27 | 2014-09-17 | Nabriva Therapeutics AG | Pleuromutilin derivatives containing a hydroxyamino- or acyloxyaminocycloalkyl group |
-
2006
- 2006-06-26 EP EP06741055.5A patent/EP1896404B1/en not_active Not-in-force
- 2006-06-26 EP EP10009685.8A patent/EP2298733B1/en not_active Not-in-force
- 2006-06-26 TW TW095122957A patent/TW200730488A/zh unknown
- 2006-06-26 WO PCT/AT2006/000260 patent/WO2007000004A1/en not_active Ceased
- 2006-06-26 JP JP2008518554A patent/JP5373393B2/ja not_active Expired - Fee Related
- 2006-06-26 US US11/814,672 patent/US7790767B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US7790767B2 (en) | 2010-09-07 |
| US20090306203A1 (en) | 2009-12-10 |
| EP1896404B1 (en) | 2014-09-17 |
| EP1896404A1 (en) | 2008-03-12 |
| JP2008546810A (ja) | 2008-12-25 |
| EP2298733A3 (en) | 2011-12-14 |
| EP2298733B1 (en) | 2016-05-25 |
| WO2007000004A1 (en) | 2007-01-04 |
| EP2298733A2 (en) | 2011-03-23 |
| TW200730488A (en) | 2007-08-16 |
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