RU2012120614A - Новые бацитрациновые антибиотики - Google Patents
Новые бацитрациновые антибиотики Download PDFInfo
- Publication number
- RU2012120614A RU2012120614A RU2012120614/04A RU2012120614A RU2012120614A RU 2012120614 A RU2012120614 A RU 2012120614A RU 2012120614/04 A RU2012120614/04 A RU 2012120614/04A RU 2012120614 A RU2012120614 A RU 2012120614A RU 2012120614 A RU2012120614 A RU 2012120614A
- Authority
- RU
- Russia
- Prior art keywords
- compound according
- compound
- pharmaceutical composition
- isoleucine
- bacitracine
- Prior art date
Links
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 title claims abstract 3
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 229940088710 antibiotic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- FAQNEUQXEJMKEU-WDSKDSINSA-N (2s,3s)-2-amino-3-methylhex-5-enoic acid Chemical compound C=CC[C@H](C)[C@H](N)C(O)=O FAQNEUQXEJMKEU-WDSKDSINSA-N 0.000 claims abstract 2
- 108010001478 Bacitracin Proteins 0.000 claims abstract 2
- 208000035143 Bacterial infection Diseases 0.000 claims abstract 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical group CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims abstract 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical group CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims abstract 2
- 229960003071 bacitracin Drugs 0.000 claims abstract 2
- 229930184125 bacitracin Natural products 0.000 claims abstract 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract 2
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims abstract 2
- 150000004677 hydrates Chemical class 0.000 claims abstract 2
- 238000000338 in vitro Methods 0.000 claims abstract 2
- 229960000310 isoleucine Drugs 0.000 claims abstract 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims abstract 2
- 230000001225 therapeutic effect Effects 0.000 claims abstract 2
- 239000004474 valine Chemical group 0.000 claims abstract 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
- C07K7/58—Bacitracins; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/03—Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof
-
- 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
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
-
- 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
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
1. Соединение, представленное формулойгдепо меньшей мере один из R, Rи Rпредставляет собой -CH=CH, и гдеR, Rи Rнезависимо представляют собой -H, -CHили -CH=CH, и его соли и гидраты.2. Соединение по п.1, где один из R, Rи Rпредставляет собой -CH.3. Соединение по п.1, где два из R, Rи Rпредставляют собой -CH.4. Соединение по п.1, где Rпредставляет собой -CH=CH.5. Соединение по п.1, где Rпредставляет собой -CH=CH.6. Соединение по п.1, где Rпредставляет собой -CH=CH.7. Соединение по п.1, где Rи Rпредставляют собой -CH=CH.8. Соединение по п.1, где Rи Rпредставляют собой -CH=CH.9. Соединение по п.1, где Rи Rпредставляют собой -CH=CH.10. Соединение по п.1, где R, Rи Rпредставляют собой -CH=CH.11. Композиция, содержащая соединение по п.1.12. Фармацевтическая композиция, содержащая соединение по п.1.13. Фармацевтическая композиция по п.12, обладающая терапевтическим эффектом.14. Применение соединения по п.1 для изготовления лекарственного средства для лечения бактериальных инфекций.15. Способ получения соединений по п.1 путем замещения изолейцина или валина на 5-метилен-изолейцин при синтезе in vitro бацитрацина.
Claims (15)
1. Соединение, представленное формулой
где
по меньшей мере один из R1, R2 и R3 представляет собой -CH=CH2, и где
R1, R2 и R3 независимо представляют собой -H, -CH3 или -CH=CH2, и его соли и гидраты.
2. Соединение по п.1, где один из R1, R2 и R3 представляет собой -CH3.
3. Соединение по п.1, где два из R1, R2 и R3 представляют собой -CH3.
4. Соединение по п.1, где R1 представляет собой -CH=CH2.
5. Соединение по п.1, где R2 представляет собой -CH=CH2.
6. Соединение по п.1, где R3 представляет собой -CH=CH2.
7. Соединение по п.1, где R1 и R2 представляют собой -CH=CH2.
8. Соединение по п.1, где R2 и R3 представляют собой -CH=CH2.
9. Соединение по п.1, где R1 и R3 представляют собой -CH=CH2.
10. Соединение по п.1, где R1, R2 и R3 представляют собой -CH=CH2.
11. Композиция, содержащая соединение по п.1.
12. Фармацевтическая композиция, содержащая соединение по п.1.
13. Фармацевтическая композиция по п.12, обладающая терапевтическим эффектом.
14. Применение соединения по п.1 для изготовления лекарственного средства для лечения бактериальных инфекций.
15. Способ получения соединений по п.1 путем замещения изолейцина или валина на 5-метилен-изолейцин при синтезе in vitro бацитрацина.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25551709P | 2009-10-28 | 2009-10-28 | |
| US61/255,517 | 2009-10-28 | ||
| PCT/EP2010/064523 WO2011051073A1 (en) | 2009-10-28 | 2010-09-30 | New bacitracin antibiotics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012120614A true RU2012120614A (ru) | 2013-12-10 |
| RU2536588C2 RU2536588C2 (ru) | 2014-12-27 |
Family
ID=43417043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012120614/04A RU2536588C2 (ru) | 2009-10-28 | 2010-09-30 | Новые бацитрациновые антибиотики |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US8410044B2 (ru) |
| EP (1) | EP2493493B1 (ru) |
| JP (1) | JP5763082B2 (ru) |
| KR (1) | KR20120097379A (ru) |
| CN (1) | CN102596218B (ru) |
| AU (1) | AU2010311762B2 (ru) |
| BR (1) | BR112012009943A2 (ru) |
| CA (1) | CA2774590A1 (ru) |
| CY (1) | CY1118233T1 (ru) |
| DK (1) | DK2493493T3 (ru) |
| ES (1) | ES2588205T3 (ru) |
| HR (1) | HRP20161020T1 (ru) |
| HU (1) | HUE029412T2 (ru) |
| IL (1) | IL219183A (ru) |
| IN (1) | IN2012DN01971A (ru) |
| LT (1) | LT2493493T (ru) |
| PL (1) | PL2493493T3 (ru) |
| PT (1) | PT2493493T (ru) |
| RU (1) | RU2536588C2 (ru) |
| SI (1) | SI2493493T1 (ru) |
| WO (1) | WO2011051073A1 (ru) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20160022T1 (hr) | 2009-10-28 | 2016-03-11 | Xellia Pharmaceuticals Aps | 2-amino-3-metil-heks-5-enoiäśna kiselina i njena uporaba u proizvodnji peptida kao što su bacitracini |
| CN109444318B (zh) * | 2018-12-03 | 2021-04-27 | 上海市食品药品检验研究院 | 一种用于分析杆菌肽组分的高效液相色谱方法 |
| CN111057131A (zh) * | 2019-12-13 | 2020-04-24 | 上海市食品药品检验所 | 一种杆菌肽及其组分的分析方法 |
| CN111678996A (zh) * | 2020-04-26 | 2020-09-18 | 上海市食品药品检验所 | 杆菌肽氧化组分及其分析方法和双键磺酸化半胱氨酸氧化组分的碎裂模式 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5300491A (en) * | 1991-10-31 | 1994-04-05 | Apothekernes Laboratorium A.S. | Treatment of protozoal infection |
| WO1997047313A1 (en) * | 1996-06-10 | 1997-12-18 | The Board Of Trustees Of The Leland Stanford Junior University | Total synthesis of bacitracin polypetides |
-
2010
- 2010-09-30 CN CN201080048962.4A patent/CN102596218B/zh not_active Expired - Fee Related
- 2010-09-30 AU AU2010311762A patent/AU2010311762B2/en not_active Ceased
- 2010-09-30 HR HRP20161020TT patent/HRP20161020T1/hr unknown
- 2010-09-30 BR BR112012009943A patent/BR112012009943A2/pt not_active IP Right Cessation
- 2010-09-30 WO PCT/EP2010/064523 patent/WO2011051073A1/en active Application Filing
- 2010-09-30 HU HUE10765613A patent/HUE029412T2/en unknown
- 2010-09-30 ES ES10765613.4T patent/ES2588205T3/es active Active
- 2010-09-30 PL PL10765613T patent/PL2493493T3/pl unknown
- 2010-09-30 LT LTEP10765613.4T patent/LT2493493T/lt unknown
- 2010-09-30 CA CA2774590A patent/CA2774590A1/en not_active Abandoned
- 2010-09-30 PT PT107656134T patent/PT2493493T/pt unknown
- 2010-09-30 DK DK10765613.4T patent/DK2493493T3/en active
- 2010-09-30 JP JP2012535720A patent/JP5763082B2/ja not_active Expired - Fee Related
- 2010-09-30 IN IN1971DEN2012 patent/IN2012DN01971A/en unknown
- 2010-09-30 US US13/502,142 patent/US8410044B2/en active Active
- 2010-09-30 KR KR1020127013675A patent/KR20120097379A/ko not_active Abandoned
- 2010-09-30 SI SI201031258A patent/SI2493493T1/sl unknown
- 2010-09-30 RU RU2012120614/04A patent/RU2536588C2/ru not_active IP Right Cessation
- 2010-09-30 EP EP10765613.4A patent/EP2493493B1/en active Active
-
2012
- 2012-04-15 IL IL219183A patent/IL219183A/en not_active IP Right Cessation
-
2016
- 2016-08-25 CY CY20161100841T patent/CY1118233T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN2012DN01971A (ru) | 2015-08-21 |
| CY1118233T1 (el) | 2017-06-28 |
| ES2588205T3 (es) | 2016-10-31 |
| AU2010311762B2 (en) | 2015-09-24 |
| EP2493493A1 (en) | 2012-09-05 |
| AU2010311762A1 (en) | 2012-03-29 |
| CA2774590A1 (en) | 2011-05-05 |
| US20120202737A1 (en) | 2012-08-09 |
| HUE029412T2 (en) | 2017-02-28 |
| KR20120097379A (ko) | 2012-09-03 |
| DK2493493T3 (en) | 2016-09-05 |
| CN102596218A (zh) | 2012-07-18 |
| WO2011051073A1 (en) | 2011-05-05 |
| JP5763082B2 (ja) | 2015-08-12 |
| SI2493493T1 (sl) | 2016-10-28 |
| US8410044B2 (en) | 2013-04-02 |
| CN102596218B (zh) | 2014-10-22 |
| LT2493493T (lt) | 2016-09-26 |
| BR112012009943A2 (pt) | 2019-09-24 |
| PT2493493T (pt) | 2016-08-31 |
| EP2493493B1 (en) | 2016-07-06 |
| IL219183A0 (en) | 2012-06-28 |
| PL2493493T3 (pl) | 2017-01-31 |
| IL219183A (en) | 2015-04-30 |
| HRP20161020T1 (hr) | 2016-10-21 |
| JP2013509367A (ja) | 2013-03-14 |
| RU2536588C2 (ru) | 2014-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20171001 |