ES2640289T3 - Combinaciones con un péptido de esqueleto ciclado - Google Patents
Combinaciones con un péptido de esqueleto ciclado Download PDFInfo
- Publication number
- ES2640289T3 ES2640289T3 ES13745848.5T ES13745848T ES2640289T3 ES 2640289 T3 ES2640289 T3 ES 2640289T3 ES 13745848 T ES13745848 T ES 13745848T ES 2640289 T3 ES2640289 T3 ES 2640289T3
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- Prior art keywords
- dab
- cfu
- compound
- cycled
- combinations
- 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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- 108090000765 processed proteins & peptides Proteins 0.000 title 1
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 abstract description 10
- 229960003405 ciprofloxacin Drugs 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 2
- OGNSCSPNOLGXSM-GSVOUGTGSA-N D-2,4-diaminobutyric acid Chemical group NCC[C@@H](N)C(O)=O OGNSCSPNOLGXSM-GSVOUGTGSA-N 0.000 abstract 1
- OGNSCSPNOLGXSM-VKHMYHEASA-N L-2,4-diaminobutyric acid Chemical group NCC[C@H](N)C(O)=O OGNSCSPNOLGXSM-VKHMYHEASA-N 0.000 abstract 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 abstract 1
- 229960004821 amikacin Drugs 0.000 abstract 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 abstract 1
- 229960004099 azithromycin Drugs 0.000 abstract 1
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 229960003104 ornithine Drugs 0.000 abstract 1
- 239000000816 peptidomimetic Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940125904 compound 1 Drugs 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 108010078777 Colistin Proteins 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000006161 blood agar Substances 0.000 description 2
- 229960003346 colistin Drugs 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- JORAUNFTUVJTNG-BSTBCYLQSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Chemical compound CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O JORAUNFTUVJTNG-BSTBCYLQSA-N 0.000 description 2
- XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 description 2
- KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 description 2
- QAXBVGVYDCAVLV-UHFFFAOYSA-N tiletamine Chemical compound C=1C=CSC=1C1(NCC)CCCCC1=O QAXBVGVYDCAVLV-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GDSCFOSHSOWNDL-UHFFFAOYSA-N Zolasepam Chemical compound N=1CC(=O)N(C)C(N(N=C2C)C)=C2C=1C1=CC=CC=C1F GDSCFOSHSOWNDL-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960004523 tiletamine Drugs 0.000 description 1
- 229960001366 zolazepam Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/7036—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin having at least one amino group directly attached to the carbocyclic ring, e.g. streptomycin, gentamycin, amikacin, validamycin, fortimicins
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
- A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
- A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
- A61K47/6807—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug or compound being a sugar, nucleoside, nucleotide, nucleic acid, e.g. RNA antisense
- A61K47/6809—Antibiotics, e.g. antitumor antibiotics anthracyclins, adriamycin, doxorubicin or daunomycin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
Abstract
Una combinación que comprende un peptidomimético de horquilla-ß de fórmula cyclo(-Thr-Trp-Ile-Dab-Orn-DDab-Dab-Trp-Dab-Dab-Ala-Ser-DPro-Pro) (I), en donde Dab es ácido (S)-2,4-diaminobutanoico; DDab es ácido (R)-2,4-diaminobutanoico; Orn es ácido (S)-2,5-diaminopentanoico; y un compuesto adicional con una actividad antibiótica seleccionado entre ertapenemo, azitromicina, ciprofloxacina, o amikacina, o una sal farmacéuticamente aceptable de los mismos.
Description
aplicaciones de 20 µI sobre placas de agar sangre. Todas las placas de agar se incubaron 18-24 horas a 35°C en aire ambiente.
Recuentos de UFC
5
Se determinó que las UFC/ml en el inóculo eran 7,0 log10 UFC/ml que se corresponden con 5,8 log10 UFC/ratón. A las 4 horas de la infección, el log10 medio de UFC/pulmón fue de 5,63 y el nivel de UFC se mantuvo en un nivel similar después de 24 horas en el grupo solo con vehículo. El tratamiento con una combinación del compuesto 1 a 1,88-25 mg/kg y ciprofloxacina dio como resultado una
10 reducción significativa de los niveles de UFC en comparación con el tratamiento con vehículo (p <0,001). El tratamiento con el compuesto 1 solo (5,5 mg/kg) tuvo un efecto significativo sobre la reducción de las cargas bacterianas (p <0,001), después de lo cual el tratamiento con colistina sola (20 mg/kg) y el tratamiento con ciprofloxacina sola (20 mg/kg) no tuvieron efecto o tuvieron solo ligeros efectos sobre las cargas bacterianas.
15 La evaluación de la curva de dosis-respuesta para la DE50 del compuesto 1 en presencia de una dosis fija de ciprofloxacina (20 mg/kg) contra PA9349 en los pulmones murinos utilizando un modelo de dosis-respuesta sigmoideo (pendiente variable) reveló una estimación de 1,55 mg/kg. La Tabla 3 a continuación resume los valores de eficacia relevantes.
20 Tabla 3: Valores de eficacia del compuesto 1
- Compuesto 1
- Compuesto 1 en presencia de 20 mg/kg de ciprofloxacina
- Nivel superior
- 1,59 log10 UFC/ml -0,21 log10 UFC/ml
- Nivel inferior
- -0,80 log10 UFC/ml -4,17 log10 UFC/ml
- Emax
- -2,4 log10 UFC/ml 3,96 log10 UFC/ml
- DE50
- 7,35 mg/kg 1,55 mg/kg
- Dosis estática
- 9,15 mg/kg nd
- 1 log dosis de destrucción
- nd 0,45 mg/kg
- 2 log dosis de destrucción
- nd 1,00 mg/kg
- 3 log dosis de destrucción
- nd 1,82 mg/kg
- R2
- 0,67 0,54
- nd: no determinado
Eficacia en el modelo de neumonía murina contra Pseudomonas aeruginosa PA18298 y estimación de la DE50
Se determinaron la eficacia y la DE50 del compuesto de fórmula (I) ("compuesto 1") frente al aislado clínico de Pseudomonas aeruginosa PA18298 en un modelo de neumonía en ratones. Los recuentos de colonias en los pulmones se determinaron a las 18 -20 horas del tratamiento.
30
Infección de ratones
Colonias frescas cultivadas durante la noche de PA18298 procedentes de una placa de agar sangre de caballo al 5% fueron suspendidas en solución salina estéril al 0,9% hasta aproximadamente 108 UFC/ml y posteriormente se
35 diluyeron hasta aproximadamente 4x107 UFC/ml. Los ratones hembra (DBA/2, no consanguíneos, 18-22 g, Charles River) se anestesiaron con 0,1 ml de Zoletil (tiletamina + zolazepam) y se les inoculó a través de la nariz una pipeta con 0,05 ml de la suspensión de bacterias que contenía aproximadamente 1x106 UFC. A las 4 horas de la inoculación, los ratones se trataron por vía oral con 45 µΙ de neurofeno (20 mg de ibuprofeno/ml correspondiente a aproximadamente 30 mg/kg) como analgésico.
40
Tratamiento de ratones con el compuesto 1
Se disolvió un vial que contenía 10 mg del compuesto 1 activo en 2 ml de solución salina estéril al 0,9% hasta una concentración de 5 mg/ml y se diluyó adicionalmente con solución salina hasta 2, 1, 0,75, 0,55, 0,275 y 0,137 mg/ml.
45 Los ratones se trataron por vía subcutánea en la región del cuello con 0,2 ml con una dosis única a las 4 horas después de la infección calculándose la dosis en base a un peso medio del animal de 20 g. Como control positivo se utilizó colistina de la misma manera con una dosis fija de 20 mg/kg.
12
Claims (1)
-
imagen1 imagen2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12005743 | 2012-08-08 | ||
| EP12005743 | 2012-08-08 | ||
| PCT/EP2013/066551 WO2014023766A1 (en) | 2012-08-08 | 2013-08-07 | Combinations with a backbone-cyclized peptide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2640289T3 true ES2640289T3 (es) | 2017-11-02 |
Family
ID=46796225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13745848.5T Active ES2640289T3 (es) | 2012-08-08 | 2013-08-07 | Combinaciones con un péptido de esqueleto ciclado |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US9814754B2 (es) |
| EP (1) | EP2882771B1 (es) |
| JP (2) | JP6486271B2 (es) |
| KR (1) | KR102142870B1 (es) |
| CN (1) | CN104684924B (es) |
| AU (1) | AU2013301576B2 (es) |
| BR (1) | BR112015002726B1 (es) |
| CA (1) | CA2887388C (es) |
| CY (1) | CY1120727T1 (es) |
| DK (1) | DK2882771T3 (es) |
| EA (1) | EA030524B1 (es) |
| ES (1) | ES2640289T3 (es) |
| HK (1) | HK1207868A1 (es) |
| HR (1) | HRP20171385T1 (es) |
| HU (1) | HUE036289T2 (es) |
| IL (1) | IL236696B (es) |
| LT (1) | LT2882771T (es) |
| MX (2) | MX366993B (es) |
| NZ (1) | NZ703723A (es) |
| PL (1) | PL2882771T3 (es) |
| PT (1) | PT2882771T (es) |
| RS (1) | RS56350B1 (es) |
| SG (1) | SG11201500130WA (es) |
| SI (1) | SI2882771T1 (es) |
| WO (1) | WO2014023766A1 (es) |
| ZA (1) | ZA201500277B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008104090A1 (en) | 2007-02-28 | 2008-09-04 | Polyphor Ag | Template-fixed peptidomimetics |
| KR101692992B1 (ko) | 2015-05-20 | 2017-01-17 | 연세대학교 산학협력단 | 고리형 펩타이드의 사전 활성화 합성방법 및 이에 따라 합성된 고리형 펩타이드 |
| EP4247338A2 (en) * | 2020-11-23 | 2023-09-27 | Spexis AG | Compositions of a beta-hairpin peptidomimetic and aerosol dosage forms thereof |
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| AU2003232253A1 (en) * | 2003-05-02 | 2004-11-23 | Polyphor Ag | Template-fixed beta-hairpin peptidomimetics with cxcr4 antagonizing activity |
| WO2007079597A1 (en) * | 2006-01-16 | 2007-07-19 | Polyphor Ltd. | Template - fixed peptidomimetics with antimicrobial activity |
| US20100035845A1 (en) | 2008-08-06 | 2010-02-11 | Wyeth | Tigecycline formulations |
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