JP5372505B2 - 抗菌活性を示すプレウロムチリン誘導体 - Google Patents
抗菌活性を示すプレウロムチリン誘導体 Download PDFInfo
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- JP5372505B2 JP5372505B2 JP2008524308A JP2008524308A JP5372505B2 JP 5372505 B2 JP5372505 B2 JP 5372505B2 JP 2008524308 A JP2008524308 A JP 2008524308A JP 2008524308 A JP2008524308 A JP 2008524308A JP 5372505 B2 JP5372505 B2 JP 5372505B2
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- Prior art keywords
- mutilin
- acetyl
- sulfanyl
- cyclopent
- ethylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 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 6
- 230000000844 anti-bacterial effect Effects 0.000 title description 4
- 230000001747 exhibiting effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 239000003814 drug Substances 0.000 claims abstract description 8
- 229960002771 retapamulin Drugs 0.000 claims description 189
- -1 (3- (morpholin-4-yl) -cyclohexane-1-yl) -sulfanyl Chemical group 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
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- 238000011282 treatment Methods 0.000 claims description 16
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
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- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
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- 239000012453 solvate Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 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
- 239000012085 test solution Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229940098465 tincture Drugs 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
- 201000008827 tuberculosis Diseases 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 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
- 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
-
- 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
- A61P31/02—Local antiseptics
-
- 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
- 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0515995.9 | 2005-08-03 | ||
| GBGB0515995.9A GB0515995D0 (en) | 2005-08-03 | 2005-08-03 | Organic compounds |
| PCT/AT2006/000318 WO2007014409A1 (en) | 2005-08-03 | 2006-07-26 | Pleuromutilin derivatives useful as antibacterials |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009502974A JP2009502974A (ja) | 2009-01-29 |
| JP2009502974A5 JP2009502974A5 (enExample) | 2012-12-13 |
| JP5372505B2 true JP5372505B2 (ja) | 2013-12-18 |
Family
ID=34984042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008524308A Expired - Fee Related JP5372505B2 (ja) | 2005-08-03 | 2006-07-26 | 抗菌活性を示すプレウロムチリン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8343972B2 (enExample) |
| EP (2) | EP1910282B1 (enExample) |
| JP (1) | JP5372505B2 (enExample) |
| GB (1) | GB0515995D0 (enExample) |
| TW (1) | TWI414511B (enExample) |
| WO (1) | WO2007014409A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US8222407B2 (en) | 2007-05-24 | 2012-07-17 | Kyorin Pharmaceutical Co., Ltd. | Mutilin derivative having heterocyclic aromatic ring carboxylic acid structure in substituent at 14-position |
| EP2159220A1 (en) | 2008-09-02 | 2010-03-03 | Nabriva Therapeutics AG | Organic compounds |
| WO2010056855A1 (en) * | 2008-11-13 | 2010-05-20 | Teva Pharmaceutical Industries Ltd. | Preparation of retapamulin via its pleuromutilin-thiol precursor |
| EP2433926A1 (en) * | 2010-09-09 | 2012-03-28 | Nabriva Therapeutics AG | Pleuromutilin derivatives for use in the treatment of diseases mediated by microbes |
| 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 |
| MX349739B (es) * | 2012-03-20 | 2017-08-10 | Firmenich & Cie | Compuestos para una liberacion controlada de moleculas perfumantes activas. |
| CN103319437B (zh) * | 2013-06-20 | 2016-05-04 | 中国农业科学院兰州畜牧与兽药研究所 | 具有噻二唑骨架的截短侧耳素类衍生物及其制备方法、应用 |
| MX383032B (es) | 2015-06-17 | 2025-03-13 | Nabriva Therapeutics GmbH | Formulaciones farmaceuticas inyectables de lefamulina. |
| 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 |
| WO2020198478A1 (en) | 2019-03-28 | 2020-10-01 | Zoetis Services Llc | Serotonin 5-ht2b inhibitory compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9918037D0 (en) * | 1999-07-30 | 1999-09-29 | Biochemie Gmbh | Organic compounds |
| GB0017031D0 (en) * | 2000-07-11 | 2000-08-30 | Biochemie Gmbh | Antimicrobials |
| GB0207495D0 (en) | 2002-03-28 | 2002-05-08 | Biochemie Gmbh | Organic compounds |
| GB0209262D0 (en) * | 2002-04-23 | 2002-06-05 | Biochemie Gmbh | Organic compounds |
| JP4611020B2 (ja) * | 2002-07-24 | 2011-01-12 | ナブリバ・セラピユーテイクス・アクチエンゲゼルシヤフト | 抗菌剤としてのプレウロムチリン（ｐｌｅｕｒｏｍｕｔｉｌｉｎ）誘導体 |
| GB0308114D0 (en) * | 2003-04-08 | 2003-05-14 | Glaxo Group Ltd | Novel compounds |
-
2005
- 2005-08-03 GB GBGB0515995.9A patent/GB0515995D0/en not_active Ceased
-
2006
- 2006-07-26 EP EP06760805.9A patent/EP1910282B1/en not_active Not-in-force
- 2006-07-26 US US11/997,637 patent/US8343972B2/en not_active Expired - Fee Related
- 2006-07-26 JP JP2008524308A patent/JP5372505B2/ja not_active Expired - Fee Related
- 2006-07-26 EP EP10009686A patent/EP2266956A3/en not_active Withdrawn
- 2006-07-26 WO PCT/AT2006/000318 patent/WO2007014409A1/en not_active Ceased
- 2006-08-02 TW TW095128307A patent/TWI414511B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TW200738608A (en) | 2007-10-16 |
| WO2007014409A1 (en) | 2007-02-08 |
| EP2266956A3 (en) | 2012-04-18 |
| EP1910282A1 (en) | 2008-04-16 |
| JP2009502974A (ja) | 2009-01-29 |
| EP2266956A2 (en) | 2010-12-29 |
| US8343972B2 (en) | 2013-01-01 |
| EP1910282B1 (en) | 2014-07-02 |
| TWI414511B (zh) | 2013-11-11 |
| US20080306072A1 (en) | 2008-12-11 |
| GB0515995D0 (en) | 2005-09-07 |
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