ES2499015T3 - Agente profiláctico o terapéutico para la diarrea - Google Patents
Agente profiláctico o terapéutico para la diarrea Download PDFInfo
- Publication number
- ES2499015T3 ES2499015T3 ES08752258.7T ES08752258T ES2499015T3 ES 2499015 T3 ES2499015 T3 ES 2499015T3 ES 08752258 T ES08752258 T ES 08752258T ES 2499015 T3 ES2499015 T3 ES 2499015T3
- Authority
- ES
- Spain
- Prior art keywords
- glu
- val
- cys
- gly
- amino acid
- 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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Links
- 206010012735 Diarrhoea Diseases 0.000 title abstract description 6
- 230000000069 prophylactic effect Effects 0.000 title abstract 2
- 239000003814 drug Substances 0.000 title 1
- 229940124597 therapeutic agent Drugs 0.000 title 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 13
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 abstract description 9
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 abstract description 9
- 230000003213 activating effect Effects 0.000 abstract description 7
- UPCDLBPYWXOCOK-UHFFFAOYSA-N N-L-gamma-glutamyl-S-methyl-L-cysteine Natural products CSCC(C(O)=O)NC(=O)CCC(N)C(O)=O UPCDLBPYWXOCOK-UHFFFAOYSA-N 0.000 abstract description 5
- RITKHVBHSGLULN-WHFBIAKZSA-N L-gamma-glutamyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(O)=O RITKHVBHSGLULN-WHFBIAKZSA-N 0.000 abstract description 4
- SNCKGJWJABDZHI-ZKWXMUAHSA-N gamma-Glu-Ile Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)CC[C@H](N)C(O)=O SNCKGJWJABDZHI-ZKWXMUAHSA-N 0.000 abstract description 4
- RQNSKRXMANOPQY-BQBZGAKWSA-N gamma-Glu-Met Chemical compound CSCC[C@@H](C(O)=O)NC(=O)CC[C@H](N)C(O)=O RQNSKRXMANOPQY-BQBZGAKWSA-N 0.000 abstract description 4
- 108010068906 gamma-glutamylcysteine Proteins 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 3
- JHFNSBBHKSZXKB-VKHMYHEASA-N Asp-Gly Chemical compound OC(=O)C[C@H](N)C(=O)NCC(O)=O JHFNSBBHKSZXKB-VKHMYHEASA-N 0.000 abstract description 2
- OOULJWDSSVOMHX-WDSKDSINSA-N Cys-Met Chemical compound CSCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CS OOULJWDSSVOMHX-WDSKDSINSA-N 0.000 abstract description 2
- FCQBDQYWNGUTPD-BQBZGAKWSA-N Gamma glutamyl ornithine Chemical compound NCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCC(O)=O FCQBDQYWNGUTPD-BQBZGAKWSA-N 0.000 abstract description 2
- SQBNIUOYNOKDTI-WHFBIAKZSA-N Gamma-glutamyl-Serine Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CO)C(O)=O SQBNIUOYNOKDTI-WHFBIAKZSA-N 0.000 abstract description 2
- PABVKUJVLNMOJP-WHFBIAKZSA-N Glu-Cys Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CS)C(O)=O PABVKUJVLNMOJP-WHFBIAKZSA-N 0.000 abstract description 2
- MFBYPDKTAJXHNI-VKHMYHEASA-N Gly-Cys Chemical compound [NH3+]CC(=O)N[C@@H](CS)C([O-])=O MFBYPDKTAJXHNI-VKHMYHEASA-N 0.000 abstract description 2
- MYFMARDICOWMQP-UHFFFAOYSA-N L-L-gamma-Glutamylleucine Natural products CC(C)CC(C(O)=O)NC(=O)CCC(N)C(O)=O MYFMARDICOWMQP-UHFFFAOYSA-N 0.000 abstract description 2
- AQAKHZVPOOGUCK-UHFFFAOYSA-N L-L-gamma-Glutamylvaline Natural products CC(C)C(C(O)=O)NC(=O)CCC(N)C(O)=O AQAKHZVPOOGUCK-UHFFFAOYSA-N 0.000 abstract description 2
- ZUKPVRWZDMRIEO-VKHMYHEASA-N L-cysteinylglycine Chemical compound SC[C@H]([NH3+])C(=O)NCC([O-])=O ZUKPVRWZDMRIEO-VKHMYHEASA-N 0.000 abstract description 2
- ACIJGUBIMXQCMF-UHFFFAOYSA-N N-L-gamma-glutamyl-glycine Natural products OC(=O)C(N)CCC(=O)NCC(O)=O ACIJGUBIMXQCMF-UHFFFAOYSA-N 0.000 abstract description 2
- 108010047857 aspartylglycine Proteins 0.000 abstract description 2
- 108010016616 cysteinylglycine Proteins 0.000 abstract description 2
- WQXXXVRAFAKQJM-WHFBIAKZSA-N gamma-Glu-Ala Chemical compound OC(=O)[C@H](C)NC(=O)CC[C@H](N)C(O)=O WQXXXVRAFAKQJM-WHFBIAKZSA-N 0.000 abstract description 2
- ACIJGUBIMXQCMF-BYPYZUCNSA-N gamma-Glu-Gly Chemical compound OC(=O)[C@@H](N)CCC(=O)NCC(O)=O ACIJGUBIMXQCMF-BYPYZUCNSA-N 0.000 abstract description 2
- MYFMARDICOWMQP-YUMQZZPRSA-N gamma-Glu-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)CC[C@H](N)C(O)=O MYFMARDICOWMQP-YUMQZZPRSA-N 0.000 abstract description 2
- AQAKHZVPOOGUCK-XPUUQOCRSA-N gamma-Glu-Val Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)CC[C@H](N)C(O)=O AQAKHZVPOOGUCK-XPUUQOCRSA-N 0.000 abstract description 2
- BBAYFIRFVORJLJ-UHFFFAOYSA-N gamma-Glutamyl-alpha-ornitine Natural products NCCCC(C(O)=O)NC(=O)CCC(N)C(O)=O BBAYFIRFVORJLJ-UHFFFAOYSA-N 0.000 abstract description 2
- 108010064169 gamma-glutamyl-leucine Proteins 0.000 abstract description 2
- 108010067681 gamma-glutamylornithine Proteins 0.000 abstract description 2
- GWNXFCYUJXASDX-UHFFFAOYSA-N gamma-glutamylthreonine Chemical compound CC(O)C(C(O)=O)NC(=O)CCC(N)C(O)=O GWNXFCYUJXASDX-UHFFFAOYSA-N 0.000 abstract description 2
- 108010032395 gamma-glutamylvaline Proteins 0.000 abstract description 2
- DVCSNHXRZUVYAM-BQBZGAKWSA-N leu-asp Chemical compound CC(C)C[C@H](N)C(=O)N[C@H](C(O)=O)CC(O)=O DVCSNHXRZUVYAM-BQBZGAKWSA-N 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- 150000003862 amino acid derivatives Chemical class 0.000 abstract 3
- 150000001413 amino acids Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- -1 γ-Glu- t-Leu Natural products 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 3
- 210000000287 oocyte Anatomy 0.000 description 3
- HJXBLWNEFLKSSL-XVKPBYJWSA-N (2s)-2-amino-5-[[(2s)-1-(carboxymethylamino)-3-methyl-1-oxobutan-2-yl]amino]-5-oxopentanoic acid Chemical compound OC(=O)CNC(=O)[C@H](C(C)C)NC(=O)CC[C@H](N)C(O)=O HJXBLWNEFLKSSL-XVKPBYJWSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- JARGNLJYKBUKSJ-KGZKBUQUSA-N (2r)-2-amino-5-[[(2r)-1-(carboxymethylamino)-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid;hydrobromide Chemical compound Br.OC(=O)[C@H](N)CCC(=O)N[C@H](CO)C(=O)NCC(O)=O JARGNLJYKBUKSJ-KGZKBUQUSA-N 0.000 description 1
- RWAZIEYJAWTKLB-YFKPBYRVSA-N (2s)-2-amino-5-[[2-(carboxymethylamino)-2-oxoethyl]amino]-5-oxopentanoic acid Chemical compound OC(=O)[C@@H](N)CCC(=O)NCC(=O)NCC(O)=O RWAZIEYJAWTKLB-YFKPBYRVSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- XKAHUJADEPXYAH-UHFFFAOYSA-N gamma-Glu-Ser-Gly Natural products OC(=O)C(N)CCC(=O)NC(CO)C(=O)NCC(O)=O XKAHUJADEPXYAH-UHFFFAOYSA-N 0.000 description 1
- 108010044804 gamma-glutamyl-seryl-glycine Proteins 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
-
- 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
-
- 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
-
- 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
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
-
- 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
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Agente, que comprende un compuesto que posee una acción activadora del receptor cálcico para su utilización en un procedimiento destinado al tratamiento profiláctico o terapéutico de la diarrea, en el que el compuesto se selecciona de entre un péptido o un derivado peptídico, en el que el péptido es de un tipo o de dos, o más, seleccionados de entre el grupo constituido por γ-Glu-X-Gly (X representa un aminoácido o un derivado de aminoácido), γ-Glu-Val-Y (Y representa un aminoácido o un derivado de aminoácido), γ-Glu-Ala, γ-Glu-Gly, γ-Glu-Cys, γ-Glu-Met, γ-Glu-Thr, γ-Glu-Val, γ-Glu-Orn, Asp- Gly, Cys-Gly, Cys- Met, Glu-Cys, Gly-Cys, Leu-Asp, γ-Glu-Met(O), γ-Glu-γ-Glu-Val, γ-Glu-Val-NH2, γ-Glu-Val-ol, γ-Glu-Ser, γ-Glu-Tau, γ-Glu-Cys(S-Me)(O), γ-Glu-Leu, γ-Glu-Ile, γ-Glu-t-Leu, y γ-Glu-Cys(S-Me), y en el que el derivado peptídico presenta una estructura de la fórmula siguiente (3): γ-Glu-X-OCH(Z)CO2H ...(3) en el que X representa un aminoácido o un derivado de aminoácido y Z representa H o CH3.
Description
E08752258
04-09-2014
La acción activadora del receptor cálcico, de un péptido, se evaluó utilizando el procedimiento descrito en el Ejemplo
13. Es decir, se prepararon ovocitos a los que se inyectó ARNc del receptor cálcico, o agua esterilizada, pinzando el
5 potencial de membrana a -70 mV mediante el procedimiento doble de pinzado del potencial del electrodo. A los ovocitos en los que se pinzó el potencial, se añadieron γ-Glu-Cys-Gly (50 µM), γ-Glu-Cys(SNO)-Gly (50 µM), γ-Glu-Ala (50 µM), γ-Glu-Gly (500 µM), γ-Glu-Cys (50 µM), γ-Glu-Met (500 µM), γ-Glu-Thr (50 µM), γ-Glu-Val (50 µM), γ-Glu-Orn (500 µM), Asp-Gly (1 mM), Cys-Gly (1 mM), Cys-Met (1 mM), Glu-Cys (50 µM), Gly-Cys (500 µM) o Leu-Asp (1 mM), midiéndose la corriente de respuesta del Cl dependiente de la concentración del ion de Ca. En la figura 4 se
10 muestran los resultados, que demostraron que el péptido descrito anteriormente poseía una acción definida activadora del receptor cálcico.
15 La acción activadora del receptor cálcico, de un péptido, se evaluó de la misma forma que la del Ejemplo 17. Cada uno de los péptidos que se muestran en la Tabla 1, se añadió a los ovocitos en los que se había pinzado el potencial a 1000 µM, 300 µM, 100 µM, 30 µM, 10 µM, 3 µM, 1 µM, 0,3 µM y 0,1 µM, midiéndose la corriente de respuesta de Cl dependiente de la concentración del ion Ca. La concentración más baja a la que se detectó la corriente se muestra en la Tabla 1 como “actividad”. Los resultados revelaron que cada uno de los 32 tipos de péptido tenía una
20 acción activadora del receptor de calcio.
TABLA 1
- Número
- Péptido Actividad
- 1
- γ-Glu-Met(O) 1000 µM
- 2
- γ-Glu-Val-Val 1000 µM
- 3
- γ-Glu-Val-Glu 1000 µM
- 4
- γ-Glu-Val-Lys 1000 µM
- 5
- γ-Glu-Val-Arg 1000 µM
- 6
- γ-Glu-Val-Asp 1000 µM
- 7
- γ-Glu-Val-Met 1000 µM
- 8
- γ-Glu-Val-Thr 1000 µM
- 9
- γ-Glu-γ-Glu-Val 1000 µM
- 10
- γ-Glu-Val-NH2 1000 µM
- 11
- γ-Glu-Val-ol 1000 µM
- 12
- γ-Glu-Ser 300 µM
- 13
- γ-Glu-Tau 300 µM
- 14
- γ-Glu-Cys(S-Me)(O) 300 µM
- 15
- γ-Glu-Val-His 100 µM
- 16
- γ-Glu-Val-Orn 100 µM
- 17
- γ-Glu-Leu 100 µM
- 18
- γ-Glu-Ile 100 µM
- 19
- γ-Glu-t-Leu 100 µM
- 20
- γ-Glu-Cys(S-alilo)-Gly 100 µM
- 21
- γ-Glu-Val-Asn 30 µM
- 22
- γ-Glu-Gly-Gly 30 µM
- 23
- γ-Glu-Val-Phe 30 µM
- 24
- γ-Glu-Val-Ser 30 µM
- 25
- γ-Glu-Val-Pro 30 µM
- 26
- γ-Glu-Ser-Gly 30 µM
- 27
- γ-Glu-Cys(S-Me) 30 µM
- 28
- γ-Glu-Val-Cys 10 µM
- 29
- γ-Glu-Val-Gln 10 µM
- 30
- γ-Glu-Abu-Gly 3 µM
- 31
- γ-Glu-Cys(S-Me)-Gly 3 µM
- 32
- γ-Glu-Val-Gly 0,1 µM
A cada uno de los ratones Balb/c, se administró un agente anticáncer para inducir la diarrea, estudiándose el efecto
inhibitorio sobre diarrea de γ-Glu-Val-Gly (al que en lo sucesivo se hace referencia como “γEVG”). A cada uno de los 30 ratones Balb/c de 6 semanas de edad, que se había alimentado con una dieta de nutrientes proteicos (caseína al
4%) durante una semana, se le administró intraperitonealmente durante 3 días consecutivos 5-FU (1 mg/animal/día).
15
Claims (1)
-
imagen1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007123765 | 2007-05-08 | ||
| JP2007123765 | 2007-05-08 | ||
| PCT/JP2008/058328 WO2008139947A1 (ja) | 2007-05-08 | 2008-05-01 | 下痢の予防又は治療剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2499015T3 true ES2499015T3 (es) | 2014-09-26 |
Family
ID=40002155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08752258.7T Active ES2499015T3 (es) | 2007-05-08 | 2008-05-01 | Agente profiláctico o terapéutico para la diarrea |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20100105864A1 (es) |
| EP (1) | EP2156846B1 (es) |
| JP (2) | JP5321452B2 (es) |
| ES (1) | ES2499015T3 (es) |
| WO (1) | WO2008139947A1 (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2299271B9 (en) * | 2005-11-09 | 2014-02-26 | Ajinomoto Co., Inc. | Kokumi-imparting compositions |
| WO2007055388A2 (en) * | 2005-11-09 | 2007-05-18 | Ajinomoto Co., Inc. | Calcium receptor activator |
| US8420144B2 (en) * | 2005-11-09 | 2013-04-16 | Ajinomoto Co., Inc. | Kokumi-imparting agent, method of using, and compositions containing same |
| JPWO2009107660A1 (ja) * | 2008-02-25 | 2011-07-07 | 味の素株式会社 | 糖尿病又は肥満病の予防又は治療剤 |
| WO2009119554A1 (ja) * | 2008-03-24 | 2009-10-01 | 味の素株式会社 | 消化管の重炭酸分泌促進剤 |
| EP2286836A4 (en) * | 2008-04-17 | 2011-10-12 | Ajinomoto Kk | IMMUNOSTIMULATING AGENT |
| SG175000A1 (en) | 2009-04-01 | 2011-11-28 | Ajinomoto Kk | Use of peptide for imparting body taste |
| MX2012007508A (es) | 2009-12-28 | 2012-08-01 | Ajinotomo Co Inc | Derivados de lantionina. |
| CN102753042B (zh) | 2009-12-28 | 2015-01-07 | 味之素株式会社 | 浓味赋予剂 |
| EP2546231B1 (en) | 2010-03-04 | 2018-11-07 | EA Pharma Co., Ltd. | Alkylamine derivative |
| WO2013051685A1 (ja) | 2011-10-07 | 2013-04-11 | 味の素株式会社 | 変異型γ－グルタミルトランスフェラーゼ、及び、γ-グルタミルバリルグリシン又はその塩の製造法 |
| WO2015115612A1 (ja) | 2014-01-31 | 2015-08-06 | 味の素株式会社 | 変異型グルタミン酸－システインリガーゼ、及び、γ－グルタミルバリルグリシンの製造法 |
| EP3115463B1 (en) | 2014-03-05 | 2019-09-18 | Ajinomoto Co., Inc. | Method for producing gamma-glutamyl-valyl-glycine |
| JP6919566B2 (ja) | 2015-09-04 | 2021-08-18 | 味の素株式会社 | γ−グルタミルバリルグリシンの製造法 |
| JP7124338B2 (ja) | 2018-02-27 | 2022-08-24 | 味の素株式会社 | 変異型グルタチオン合成酵素、及び、γ－グルタミルバリルグリシンの製造法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1147459C (zh) * | 1994-10-21 | 2004-04-28 | Nps药物有限公司 | 钙受体活性化合物 |
| ATE430123T1 (de) * | 1996-05-01 | 2009-05-15 | Nps Pharma Inc | Inorganische am ionen-rezeptor aktive verbindungen |
| SE9904132D0 (sv) * | 1999-11-16 | 1999-11-16 | Sbl Vaccin Ab | Pharmaceutical composition for treatment of diarrhea |
| CA2494700C (en) * | 2002-08-26 | 2011-06-28 | Takeda Pharmaceutical Company Limited | Calcium receptor modulating compound and use thereof |
| US20040204577A1 (en) * | 2003-01-24 | 2004-10-14 | Ajinomoto Co., Inc. | Novel peptide-forming enzyme gene |
| US7754677B2 (en) * | 2003-12-05 | 2010-07-13 | Hill's Pet Nutrition, Inc. | Composition and method for reducing diarrhea in a mammal |
| FR2885129B1 (fr) * | 2005-04-29 | 2007-06-15 | Proskelia Sas | Nouveaux derives de l'ureee substituee parun thiazole ou benzothiazole, leur procede de preparation, leur application a titre de medicaments, les compositions pharmaceutiques les renfermant et utilisation. |
| WO2007027548A2 (en) * | 2005-09-02 | 2007-03-08 | Amgen Inc. | Methods of modulating intestinal fluid balance |
| EP2299271B9 (en) * | 2005-11-09 | 2014-02-26 | Ajinomoto Co., Inc. | Kokumi-imparting compositions |
| WO2007055388A2 (en) * | 2005-11-09 | 2007-05-18 | Ajinomoto Co., Inc. | Calcium receptor activator |
| AU2006316705B2 (en) * | 2005-11-25 | 2011-09-29 | Galapagos Sas | Urea derivatives useful as calcium receptor modulators |
| CA2672956C (en) * | 2006-10-26 | 2015-02-10 | Amgen Inc. | Calcium receptor modulating agents |
| KR101491984B1 (ko) * | 2007-05-08 | 2015-02-10 | 아지노모토 가부시키가이샤 | 감미료 |
| EP2156753A4 (en) * | 2007-05-08 | 2010-11-24 | Ajinomoto Kk | FATTY-FREE FOOD |
| CA2692598A1 (en) * | 2007-07-10 | 2009-01-15 | Amgen Inc. | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
| JPWO2009107660A1 (ja) * | 2008-02-25 | 2011-07-07 | 味の素株式会社 | 糖尿病又は肥満病の予防又は治療剤 |
| WO2009119554A1 (ja) * | 2008-03-24 | 2009-10-01 | 味の素株式会社 | 消化管の重炭酸分泌促進剤 |
| WO2010038895A1 (ja) * | 2008-10-03 | 2010-04-08 | 味の素株式会社 | ＣａＳＲアゴニスト |
-
2008
- 2008-05-01 ES ES08752258.7T patent/ES2499015T3/es active Active
- 2008-05-01 WO PCT/JP2008/058328 patent/WO2008139947A1/ja not_active Ceased
- 2008-05-01 EP EP08752258.7A patent/EP2156846B1/en not_active Not-in-force
- 2008-05-01 JP JP2009514106A patent/JP5321452B2/ja active Active
-
2009
- 2009-11-06 US US12/613,727 patent/US20100105864A1/en not_active Abandoned
-
2013
- 2013-05-20 JP JP2013106287A patent/JP5716791B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP5716791B2 (ja) | 2015-05-13 |
| EP2156846A4 (en) | 2012-03-07 |
| JPWO2008139947A1 (ja) | 2010-08-05 |
| JP2013209402A (ja) | 2013-10-10 |
| WO2008139947A1 (ja) | 2008-11-20 |
| US20100105864A1 (en) | 2010-04-29 |
| EP2156846B1 (en) | 2014-08-13 |
| EP2156846A1 (en) | 2010-02-24 |
| JP5321452B2 (ja) | 2013-10-23 |
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