DK2476701T3 - Antimikrobielle midler på basis af heminderivater - Google Patents
Antimikrobielle midler på basis af heminderivater Download PDFInfo
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- DK2476701T3 DK2476701T3 DK10815682.9T DK10815682T DK2476701T3 DK 2476701 T3 DK2476701 T3 DK 2476701T3 DK 10815682 T DK10815682 T DK 10815682T DK 2476701 T3 DK2476701 T3 DK 2476701T3
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- ZWCXYZRRTRDGQE-LUPIJMBPSA-N valyl gramicidin a Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)CC(C)C)C(=O)NCCO)=CNC2=C1 ZWCXYZRRTRDGQE-LUPIJMBPSA-N 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- 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
- A61P31/04—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
- A61P31/10—Antimycotics
-
- 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
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/795—Porphyrin- or corrin-ring-containing peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/795—Porphyrin- or corrin-ring-containing peptides
- C07K14/805—Haemoglobins; Myoglobins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (17)
1
1. Forbindelse med almen formel (I):
j nvor ι~ί-ι og n2 er ae samme ener forskellige, og hvor enten et af Ri og R2 er -OH, og det andet er - Val-Gly-Ala-(D-Leu)-Ala-(D- Val)-Val-(D-Val)-Trp-(D-Leu)-X-(D-Leu)-Trp-(D-Leu)-Trp-NHCH2CH2OH, hvor X=Trp, Phe eller Tyr (gramicidin D), - Νδ- cyclo-(Orn-Leu-D-Phe-Pro-Val)2 (gramicidin S), -Arg-Gly-Asp-OH, SEQ ID NO: 1 [-Arg-Arg-Trp-Trp-Arg-Phe- OH], -ArgArgTrpHisArgLeuLysGlu (OMe)OH eller- ArgTrpHisArgLeuLys- Glu(OMe)OH; eller Ri og R2 hver især er -NHCH2CH2OH, -GlyOMe, -NHCH(CH2OH)CH2OH, - NHCH2CH(OH)CH2OH, - Glu(ArgOMe)-ArgOMe, -HA, -Arg-ArgOMe, -ArgOMe, - SerOMe, - ØAlaHA eller -pAlaHis, hvor HA er histaminenheden ΝΠ —IIN—ch2—ch2—^ I j og Men+ er Fe2+eller Fe3+ eller et farmaceutisk acceptabelt salt deraf til anvendelse ved behandlingen eller forebyggelsen af sygdomme forårsaget af bakterier eller mikrosvampe, hvor forbindelsen indgives til en patient med behov herfor.
2. Forbindelse til anvendelse ifølge krav 1, hvor sygdommene er forårsaget af grampositive bakterier fra bakterieslægter Staphylococcus, Bacillus, Enterococcus og/eller Micrococcus. 2
3. Forbindelse til anvendelse ifølge krav 1, hvor bakterierne er resistente bakterier.
4. Forbindelse til anvendelse ifølge krav 1, hvor sygdommene er forårsaget af mikrosvampe fra mikrosvampeslægter Candida og/eller Cryptococcus.
5. Heminderivat med almen formel (I):
R.](0)C i c(0)R2 j hvor R-ι og R2 er de samme eller forskellige, og hvor enten et af Ri og R2 er -OH, og det andet er - Val-Gly-Ala-(D-Leu)-Ala-(D-Val)-Val-(D-Val)-Trp-(D-Leu)-X-(D-Leu)-Trp-(D-Leu)-Trp-NHCH2CH2OH, hvor X=Trp, Phe eller Tyr (gramicidin D), -N5-cyclo-(Orn-Leu-D-Phe-Pro-Val)2 (gramicidin S), -Arg-Gly- Asp-OH, SEQ ID NO: 1 [-Arg-Arg-Trp-Trp-Arg-Phe-OH],
eller Ri og R2 hver især er -NHCH2CH2OH, -GlyOMe, NHCH(CH2OH)CH2OH, - NHCH2CH(OH)CH2OH, - Glu(ArgOMe)-ArgOMe /ww.mn i.« λ._ λ._/-μι*- '-vor HA er histaminenheden • et farmaceutisk acceptabelt salt deraf.
6. Forbindelse ifølge krav 5, hvor et af Ri og R2 er -OH, og det andet er -Arg-Gly-Asp-OH, -Val-Gly-Ala-(D-Leu)-Ala-(D-Val)-Val-(D-Val)-Trp-(D-Leu)-X-(D-Leu)-Trp-(D-Leu)-Trp-NHCH2CH2OH, hvor X=Trp, Phe eller Tyr (gramicidin D), -Νδ- cyclo-(Orn-Leu-D-Phe-Pro-Val)2 (gramicidin S) eller SEQ ID NO: 1 [-Arg-Arg-T rp-T rp-Arg-Phe-OH]. 3
7. Forbindelse ifølge krav 5, hvor Ri=R2= -NHCH2CH2OH, -GlyOMe, -NHCH(CH2OH)CH2OH, -NHCH2CH(OH)CH2OH, -Glu(ArgOMe)-ArgOMe, -HA eller-Arg-ArgOMe.
8. Fremgangsmåde til fremstilling af forbindelser med almen formel (I) ifølge et af kravene 5 til 7, hvilken fremgangsmåde omfatter omsætning af et he-minderivat aktiveret ved carboxygruppe(r) med en aminokomponent.
9. Fremgangsmåde ifølge krav 8, hvorved det aktiverede heminderivat er hemin 6,7-bis-N-oxysuccinimidester eller hemin 6(7)-mono-N-oxy-5-norbornen-2,3-dicarboximidester, og opløsningsmidlet er N,N-dimethylformamid.
10. Fremgangsmåde ifølge krav 8, hvorved dhtert-butyl-pyrocarbonat anvendes til at aktivere en af carboxygrupperne af heminet, hvilken fremgangsmåde udføres i Ν,Ν-dimethylformamid i nærvær af pyridin.
11. Farmaceutisk sammensætning, der som en aktiv bestanddel omfatter en forbindelse med formel (I) ifølge krav 5 eller et farmaceutisk acceptabelt salt deraf, formuleret med en farmaceutisk acceptabel bærer eller excipiens.
12. Antiseptisk og/eller desinficerende sammensætning, omfattende en forbindelse med formel (I) ifølge krav 5.
13. Ikke-terapeutisk anvendelse af en forbindelse med almen formel (I) eller et farmaceutisk acceptabelt salt deraf:
4 hvor R-\ og R2 er de samme eller forskellige, og hvor enten et af Ri og R2 er -OH, og det andet er - Val-Gly-Ala-(D-Leu)-Ala-(D-Val)-Val-(D-Val)-Trp-(D-Leu)-X-(D-Leu)-Trp-(D-Leu)-Trp-NHCH2CH2OH, hvor X=Trp, Phe eller Tyr (gramicidin D), - N6-cyclo-(Orn-Leu-D-Phe-Pro-Val)2 (gramicidin S), -Arg-Gly-Asp-OH, SEQ ID NO: 1 [-Arg-Arg-Trp-Trp-Arg-Phe-OH]; eller Ri og R2 hver især er -NHCH2CH2OH, -GlyOMe, -NHCH(CH2OH)CH2OH, - NHCH2CH(OH)CH2OH, - Glu(ArgOMe)-ArgOMe,
HA er histaminenheden i j * som et antimikrobielt middel.
14. Anvendelse ifølge krav 13, hvor et antimikrobielt middel er et antibakteri-elt middel, som virker mod grampositive bakterieslægter Staphylococcus, Bacillus, Enterococcus og/eller Micrococcus.
15. Anvendelse ifølge krav 14, hvor bakterierne er resistente bakterier.
16. Anvendelse ifølge krav 13, hvor et antimikrobielt middel er et antisvam-pemiddel, som virker mod mikrosvampeslægter Candida og/eller Cryptococ-cus.
17. Anvendelse ifølge krav 13-16, hvor i forbindelsen med almen formel (I) enten et af Ri og R2 er -OH, og det andet er - Val-Gly-Ala-(D-Leu)-Ala-(D-Val)-Val-(D-Val)-Trp-(D-Leu)-X-(D-Leu)-Trp-(D-Leu)-Trp-NHCH2CH2OH, hvor X=Trp, Phe eller Tyr (gramicidin D), - N5-cyclo-(Orn-Leu-D-Phe-Pro-Val)2 (gramicidin S), -Arg-Gly- Asp-OH, SEQID NO:1 [-Arg-Arg-Trp-Trp-Arg-Phe-OH]; eller Ri og R2 hver især er -NHCH2CH2OH, -GlyOMe, NHCH(CH2OH)CH2OH, - NHCH2CH(OH)CH2OH, - Glu(ArgOMe)-ArgOMe, -ua λ,λ,
1--- ua histaminenheden
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2009133914/04A RU2415868C1 (ru) | 2009-09-10 | 2009-09-10 | Производные гемина, обладающие антимикробной активностью, или их фармацевтически приемлемые соли, способ получения, фармкомпозиция и применение |
| PCT/RU2010/000488 WO2011031187A1 (ru) | 2009-09-10 | 2010-09-08 | Антимикробные средства на основе производных гемина |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2476701T3 true DK2476701T3 (da) | 2014-11-17 |
Family
ID=43732659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK10815682.9T DK2476701T3 (da) | 2009-09-10 | 2010-09-08 | Antimikrobielle midler på basis af heminderivater |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8906897B2 (da) |
| EP (1) | EP2476701B8 (da) |
| CN (1) | CN102906110B (da) |
| DK (1) | DK2476701T3 (da) |
| EA (1) | EA020802B1 (da) |
| ES (1) | ES2527432T3 (da) |
| IN (1) | IN2012DN02980A (da) |
| PL (1) | PL2476701T3 (da) |
| RU (1) | RU2415868C1 (da) |
| UA (1) | UA108480C2 (da) |
| WO (1) | WO2011031187A1 (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2475498C1 (ru) | 2011-11-17 | 2013-02-20 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Новые производные гемина с антибактериальной и противовирусной активностью |
| CN102967649B (zh) * | 2012-05-24 | 2015-03-04 | 新疆科丽生物技术有限公司 | 电感耦合等离子体质谱在氯高铁血红素药物检测中的应用 |
| EP3295962B1 (en) * | 2016-09-15 | 2021-01-27 | Nano4Imaging GmbH | Tetrapyrrole conjugates as mri contrast agents |
| RU2678985C2 (ru) | 2017-02-06 | 2019-02-05 | Общество с ограниченной ответственностью "Научно-производственная фирма ВЕРТА" | Биоцидный пептид и препарат на его основе |
| WO2019023706A1 (en) * | 2017-07-28 | 2019-01-31 | The Penn State Research Foundation | ULTRASOUND-SENSITIVE PEPTIDE PARTICLES FOR ADMINISTRATION OF SPACE-RESOLVED MOLECULES |
| RU2656595C1 (ru) * | 2018-03-16 | 2018-06-06 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Циклическое производное гемина с антимикробными свойствами и способ его синтеза |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US5629198A (en) * | 1991-08-02 | 1997-05-13 | Meiji Milk Products Co., Ltd. | Anti-HIV agent |
| IL116126A0 (en) | 1995-11-24 | 1996-01-31 | Yeda Res & Dev | Process for the preparation of bacteriochlorophyllis some novel compounds of this type and pharmaceutical compositions comprising them |
| US6001808A (en) | 1996-08-19 | 1999-12-14 | Metatron, Inc. | Method of treating herpes virus infections with spermostatic gramicidin |
| RU2238950C2 (ru) * | 2002-04-25 | 2004-10-27 | Небольсин Владимир Евгеньевич | Производные гемина и их фармацевтически приемлемые соли, способ получения, применение и фармацевтическая композиция |
| RU2250906C2 (ru) * | 2003-07-10 | 2005-04-27 | Небольсин Владимир Евгеньевич | Способы получения геминпептидов и их применение в качестве нуклеолитических агентов |
| RU2296131C2 (ru) * | 2004-11-26 | 2007-03-27 | ООО "Фарминтерпрайсез" | Геминпептид, его фармацевтически приемлемые соли и применение в качестве противовирусного и вирулецидного агента |
| RU2280649C1 (ru) | 2004-11-26 | 2006-07-27 | ООО "Фарминтерпрайсез" | Геминпептиды, их фармацевтически приемлемые соли, фармкомпозиция и применение в качестве противоопухолевых агентов |
| RU2404191C2 (ru) * | 2007-07-09 | 2010-11-20 | ООО "Фарминтерпрайсез" | Производные гемина или их фармацевтически приемлемые соли, способ получения, композиция и применение |
-
2009
- 2009-09-10 RU RU2009133914/04A patent/RU2415868C1/ru active
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- 2010-08-09 UA UAA201204487A patent/UA108480C2/ru unknown
- 2010-09-08 PL PL10815682T patent/PL2476701T3/pl unknown
- 2010-09-08 ES ES10815682.9T patent/ES2527432T3/es active Active
- 2010-09-08 US US13/395,149 patent/US8906897B2/en not_active Expired - Fee Related
- 2010-09-08 EP EP10815682.9A patent/EP2476701B8/en active Active
- 2010-09-08 WO PCT/RU2010/000488 patent/WO2011031187A1/ru not_active Ceased
- 2010-09-08 CN CN201080048604.3A patent/CN102906110B/zh not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2476701A1 (en) | 2012-07-18 |
| RU2415868C1 (ru) | 2011-04-10 |
| UA108480C2 (en) | 2015-05-12 |
| PL2476701T3 (pl) | 2015-03-31 |
| EP2476701B1 (en) | 2014-08-13 |
| HK1179278A1 (zh) | 2013-09-27 |
| CN102906110B (zh) | 2016-04-13 |
| EP2476701A4 (en) | 2013-01-16 |
| CN102906110A (zh) | 2013-01-30 |
| US20120264724A1 (en) | 2012-10-18 |
| IN2012DN02980A (da) | 2015-07-31 |
| EA020802B1 (ru) | 2015-01-30 |
| EP2476701B8 (en) | 2014-09-24 |
| EA201270405A1 (ru) | 2012-08-30 |
| ES2527432T3 (es) | 2015-01-23 |
| WO2011031187A1 (ru) | 2011-03-17 |
| US8906897B2 (en) | 2014-12-09 |
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