FR2551088A1 - - Google Patents
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- Publication number
- FR2551088A1 FR2551088A1 FR8313828A FR8313828A FR2551088A1 FR 2551088 A1 FR2551088 A1 FR 2551088A1 FR 8313828 A FR8313828 A FR 8313828A FR 8313828 A FR8313828 A FR 8313828A FR 2551088 A1 FR2551088 A1 FR 2551088A1
- Authority
- FR
- France
- Prior art keywords
- peptide
- chain
- amino acids
- subunit
- toxin
- 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.)
- Granted
Links
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 46
- 102000009016 Cholera Toxin Human genes 0.000 claims abstract description 37
- 108010049048 Cholera Toxin Proteins 0.000 claims abstract description 37
- 150000001413 amino acids Chemical class 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000003053 toxin Substances 0.000 claims abstract description 21
- 231100000765 toxin Toxicity 0.000 claims abstract description 21
- 241000588724 Escherichia coli Species 0.000 claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 14
- 206010008631 Cholera Diseases 0.000 claims abstract description 12
- 238000010276 construction Methods 0.000 claims abstract description 8
- 208000015181 infectious disease Diseases 0.000 claims abstract description 8
- 230000002458 infectious effect Effects 0.000 claims abstract description 8
- 210000004899 c-terminal region Anatomy 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 5
- 239000000470 constituent Substances 0.000 claims abstract description 3
- 235000001014 amino acid Nutrition 0.000 claims description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 208000005577 Gastroenteritis Diseases 0.000 claims description 6
- 102000030621 adenylate cyclase Human genes 0.000 claims description 6
- 108060000200 adenylate cyclase Proteins 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 239000003223 protective agent Substances 0.000 claims description 6
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims description 5
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 5
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 claims description 5
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 5
- 230000004913 activation Effects 0.000 claims description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims description 5
- 229940095074 cyclic amp Drugs 0.000 claims description 5
- -1 t-butoxycarbonyl group Chemical group 0.000 claims description 5
- 239000004474 valine Substances 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000010532 solid phase synthesis reaction Methods 0.000 claims description 3
- 229960005486 vaccine Drugs 0.000 claims description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- 150000001510 aspartic acids Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical group C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 2
- 235000013922 glutamic acid Nutrition 0.000 claims description 2
- 239000004220 glutamic acid Substances 0.000 claims description 2
- 150000002307 glutamic acids Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 claims description 2
- 241000282326 Felis catus Species 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000011814 protection agent Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000003745 diagnosis Methods 0.000 abstract 1
- 108700012359 toxins Proteins 0.000 description 17
- 239000012634 fragment Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001308 synthesis method Methods 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 4
- 230000000968 intestinal effect Effects 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000147 enterotoxin Substances 0.000 description 3
- 231100000655 enterotoxin Toxicity 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 210000000936 intestine Anatomy 0.000 description 3
- SZXBQTSZISFIAO-ZETCQYMHSA-N (2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OC(C)(C)C SZXBQTSZISFIAO-ZETCQYMHSA-N 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101710146739 Enterotoxin Proteins 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000023445 activated T cell autonomous cell death Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 230000002163 immunogen Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- 230000005730 ADP ribosylation Effects 0.000 description 1
- 208000010444 Acidosis Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 206010027417 Metabolic acidosis Diseases 0.000 description 1
- 241000607626 Vibrio cholerae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001147 anti-toxic effect Effects 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 210000000990 duodenal loop Anatomy 0.000 description 1
- 210000001842 enterocyte Anatomy 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 229930186900 holotoxin Natural products 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 108020004084 membrane receptors Proteins 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000024715 positive regulation of secretion Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000006918 subunit interaction Effects 0.000 description 1
- 108020001572 subunits Proteins 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000033 toxigenic Toxicity 0.000 description 1
- 230000001551 toxigenic effect Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 229940118696 vibrio cholerae Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/195—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria
- C07K14/28—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria from Vibrionaceae (F)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/195—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria
- C07K14/24—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria from Enterobacteriaceae (F), e.g. Citrobacter, Serratia, Proteus, Providencia, Morganella, Yersinia
- C07K14/245—Escherichia (G)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/832—Drug, bio-affecting and body treating compositions involving bacterial toxin that has modified amino acid sequence
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/81—Packaged device or kit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/975—Kit
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8313828A FR2551088B1 (en, 2012) | 1983-08-29 | 1983-08-29 | |
| US06/643,955 US4686281A (en) | 1983-08-29 | 1984-08-24 | Novel synthetic peptide, process for its preparation and medicaments containing it |
| DE8484401720T DE3462040D1 (en) | 1983-08-29 | 1984-08-27 | Synthetic peptide, process for its preparation, and drugs thereof |
| MA20438A MA20214A1 (fr) | 1983-08-29 | 1984-08-27 | Nouveau peptide de synthese, son procede de preparation. |
| EP84401720A EP0139555B1 (fr) | 1983-08-29 | 1984-08-27 | Nouveau peptide de synthèse, son procédé de préparation et médicaments le contenant |
| AT84401720T ATE24918T1 (de) | 1983-08-29 | 1984-08-27 | Synthetische peptide, verfahren zu deren herstellung und sie enthaltende arzneimittel. |
| GR80230A GR80230B (en) | 1983-08-29 | 1984-08-28 | Novel synthesis peptide method for the preparation thereof and medicaments containing them |
| ES535471A ES8608046A1 (es) | 1983-08-29 | 1984-08-28 | Procedimiento de un nuevo peptido como agente de proteccion contra el colera y-0 las gastroenteritis infecciosas. |
| JP59180250A JPS60155195A (ja) | 1983-08-29 | 1984-08-29 | 新規合成ペプチド、その製法及びそれを含む医薬 |
| OA58377A OA07802A (fr) | 1983-08-29 | 1984-08-29 | Nouveau pesticide de synthèse, son procédé de préparation et médicaments le contenant. |
| US07/004,416 US4898815A (en) | 1983-08-29 | 1987-01-20 | Novel synthetic peptide, process for its preparation and medicaments containing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8313828A FR2551088B1 (en, 2012) | 1983-08-29 | 1983-08-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2551088A1 true FR2551088A1 (en, 2012) | 1985-03-01 |
| FR2551088B1 FR2551088B1 (en, 2012) | 1985-12-06 |
Family
ID=9291849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8313828A Expired FR2551088B1 (en, 2012) | 1983-08-29 | 1983-08-29 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4686281A (en, 2012) |
| EP (1) | EP0139555B1 (en, 2012) |
| JP (1) | JPS60155195A (en, 2012) |
| AT (1) | ATE24918T1 (en, 2012) |
| DE (1) | DE3462040D1 (en, 2012) |
| ES (1) | ES8608046A1 (en, 2012) |
| FR (1) | FR2551088B1 (en, 2012) |
| GR (1) | GR80230B (en, 2012) |
| MA (1) | MA20214A1 (en, 2012) |
| OA (1) | OA07802A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997000088A3 (en) * | 1995-06-14 | 1997-03-27 | Baylor College Medicine | Rotavirus enterotoxin nsp4 and methods of using same |
| US6673355B1 (en) | 1995-06-14 | 2004-01-06 | Baylor College Of Medicine | Rotavirus enterotoxin NSP4 and methods of using same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3712890A1 (de) * | 1987-04-15 | 1988-10-27 | Teichmann Reinhard K Priv Doz | Verwendung antigener substanzen zur prophylaxe oder therapie von stoerungen und krankheiten im verdauungstrakt von tieren und menschen |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2395030A1 (fr) * | 1977-06-22 | 1979-01-19 | Sandoz Sa | Vaccins pour le traitement de la colibacillose des porcelets et leur preparation |
| US4392997A (en) * | 1981-07-06 | 1983-07-12 | Northwestern University | Antigenic peptide compounds |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2919592A1 (de) * | 1979-05-15 | 1981-01-15 | Max Planck Gesellschaft | Verfahren zur herstellung von thymosin- alpha 1 und derivaten davon |
| DE3163469D1 (en) * | 1980-05-12 | 1984-06-14 | Choay Sa | Oligopeptides with specific inhibiting properties of collagen induced aggregation, process for preparing the same and pharmaceutical compositions containing them |
| US4520016A (en) * | 1980-06-17 | 1985-05-28 | Kabigen Ab | Bacteriolytic proteins |
| DE3117934A1 (de) * | 1981-05-06 | 1982-12-09 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Neues peptid, verfahren zu seiner gewinnung und dieses enthaltendes arzneimittel |
| US4415558A (en) * | 1981-06-08 | 1983-11-15 | The Salk Institute For Biological Studies | CRF And analogs |
| NL8102856A (nl) * | 1981-06-15 | 1983-01-03 | Unilever Nv | Werkwijze ter bereiding van bloedceleiwit en haem uit haemoglobine. |
| FR2525592B1 (en, 2012) * | 1982-04-26 | 1984-09-14 | Pasteur Institut | |
| ZA838780B (en) * | 1982-11-26 | 1985-01-30 | Nyegaard & Co As | Peptide compounds |
| US4410514A (en) * | 1982-12-06 | 1983-10-18 | The Salk Institute For Biological Studies | GnRH Agonists |
| US4504414A (en) * | 1983-03-28 | 1985-03-12 | Board Of Regents, The University Of Texas System | Synthetic pyridyl-alanyl decapeptides having antiovulatory activity |
| US4504415A (en) * | 1983-04-04 | 1985-03-12 | Hoffman-La Roche Inc. | Synthesis of thymosin α1 and desacetyl thymosin α1 |
| US4478827A (en) * | 1983-05-09 | 1984-10-23 | The General Hospital Corporation | Renin inhibitors |
| US4515920A (en) * | 1984-04-30 | 1985-05-07 | The Rockefeller University | Synthesis of peptides and proteins |
-
1983
- 1983-08-29 FR FR8313828A patent/FR2551088B1/fr not_active Expired
-
1984
- 1984-08-24 US US06/643,955 patent/US4686281A/en not_active Expired - Fee Related
- 1984-08-27 EP EP84401720A patent/EP0139555B1/fr not_active Expired
- 1984-08-27 DE DE8484401720T patent/DE3462040D1/de not_active Expired
- 1984-08-27 MA MA20438A patent/MA20214A1/fr unknown
- 1984-08-27 AT AT84401720T patent/ATE24918T1/de not_active IP Right Cessation
- 1984-08-28 ES ES535471A patent/ES8608046A1/es not_active Expired
- 1984-08-28 GR GR80230A patent/GR80230B/el unknown
- 1984-08-29 OA OA58377A patent/OA07802A/xx unknown
- 1984-08-29 JP JP59180250A patent/JPS60155195A/ja active Pending
-
1987
- 1987-01-20 US US07/004,416 patent/US4898815A/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2395030A1 (fr) * | 1977-06-22 | 1979-01-19 | Sandoz Sa | Vaccins pour le traitement de la colibacillose des porcelets et leur preparation |
| US4392997A (en) * | 1981-07-06 | 1983-07-12 | Northwestern University | Antigenic peptide compounds |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997000088A3 (en) * | 1995-06-14 | 1997-03-27 | Baylor College Medicine | Rotavirus enterotoxin nsp4 and methods of using same |
| US6673355B1 (en) | 1995-06-14 | 2004-01-06 | Baylor College Of Medicine | Rotavirus enterotoxin NSP4 and methods of using same |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE24918T1 (de) | 1987-01-15 |
| GR80230B (en) | 1985-01-02 |
| JPS60155195A (ja) | 1985-08-15 |
| FR2551088B1 (en, 2012) | 1985-12-06 |
| OA07802A (fr) | 1986-11-20 |
| EP0139555B1 (fr) | 1987-01-14 |
| US4686281A (en) | 1987-08-11 |
| US4898815A (en) | 1990-02-06 |
| DE3462040D1 (en) | 1987-02-19 |
| ES535471A0 (es) | 1986-06-16 |
| MA20214A1 (fr) | 1985-04-01 |
| ES8608046A1 (es) | 1986-06-16 |
| EP0139555A1 (fr) | 1985-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |