CA1152493A - Thiolated polypeptide compound derived from a tetanus toxin fragment, the process for obtaining and its applications - Google Patents
Thiolated polypeptide compound derived from a tetanus toxin fragment, the process for obtaining and its applicationsInfo
- Publication number
- CA1152493A CA1152493A CA000365671A CA365671A CA1152493A CA 1152493 A CA1152493 A CA 1152493A CA 000365671 A CA000365671 A CA 000365671A CA 365671 A CA365671 A CA 365671A CA 1152493 A CA1152493 A CA 1152493A
- Authority
- CA
- Canada
- Prior art keywords
- thiolation
- groups
- agent
- fragment
- iib
- 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.)
- Expired
Links
- 239000012634 fragment Substances 0.000 title claims abstract description 77
- 150000001875 compounds Chemical class 0.000 title claims abstract description 47
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract description 40
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 40
- 229920001184 polypeptide Polymers 0.000 title claims abstract description 39
- 108010055044 Tetanus Toxin Proteins 0.000 title claims abstract description 38
- 229940118376 tetanus toxin Drugs 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims description 42
- 230000008569 process Effects 0.000 title claims description 30
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 40
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 20
- 230000009844 retrograde axon cargo transport Effects 0.000 claims abstract description 5
- 238000006177 thiolation reaction Methods 0.000 claims description 43
- 239000000126 substance Substances 0.000 claims description 22
- NRFJZTXWLKPZAV-UHFFFAOYSA-N N-(2-oxo-3-thiolanyl)acetamide Chemical compound CC(=O)NC1CCSC1=O NRFJZTXWLKPZAV-UHFFFAOYSA-N 0.000 claims description 5
- 229960004753 citiolone Drugs 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- QXDUMOMMZMHKOH-UHFFFAOYSA-N 2-sulfanylpentanamide Chemical compound CCCC(S)C(N)=O QXDUMOMMZMHKOH-UHFFFAOYSA-N 0.000 claims description 4
- CNHYKKNIIGEXAY-UHFFFAOYSA-N thiolan-2-imine Chemical compound N=C1CCCS1 CNHYKKNIIGEXAY-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 abstract description 23
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- 238000002474 experimental method Methods 0.000 description 7
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- 239000000243 solution Substances 0.000 description 7
- 231100000419 toxicity Toxicity 0.000 description 7
- 230000001988 toxicity Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 6
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 150000002270 gangliosides Chemical class 0.000 description 6
- 241000700605 Viruses Species 0.000 description 5
- 239000000427 antigen Substances 0.000 description 5
- 108091007433 antigens Proteins 0.000 description 5
- 102000036639 antigens Human genes 0.000 description 5
- 239000002246 antineoplastic agent Substances 0.000 description 5
- 238000002372 labelling Methods 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- 230000002588 toxic effect Effects 0.000 description 5
- 102000016607 Diphtheria Toxin Human genes 0.000 description 4
- 108010053187 Diphtheria Toxin Proteins 0.000 description 4
- 206010043376 Tetanus Diseases 0.000 description 4
- 230000008335 axon cargo transport Effects 0.000 description 4
- 230000003376 axonal effect Effects 0.000 description 4
- 125000005414 dithiopyridyl group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
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- 239000011541 reaction mixture Substances 0.000 description 4
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- 239000003053 toxin Substances 0.000 description 4
- 231100000765 toxin Toxicity 0.000 description 4
- 108700012359 toxins Proteins 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JWDFQMWEFLOOED-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(pyridin-2-yldisulfanyl)propanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCSSC1=CC=CC=N1 JWDFQMWEFLOOED-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229960000814 tetanus toxoid Drugs 0.000 description 3
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 2
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 2
- 102000009016 Cholera Toxin Human genes 0.000 description 2
- 108010049048 Cholera Toxin Proteins 0.000 description 2
- 241000193449 Clostridium tetani Species 0.000 description 2
- 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 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
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- SGNXVBOIDPPRJJ-PSASIEDQSA-N 1-[(1r,6r)-9-azabicyclo[4.2.1]non-4-en-5-yl]ethanone Chemical compound CC(=O)C1=CCC[C@@H]2CC[C@H]1N2 SGNXVBOIDPPRJJ-PSASIEDQSA-N 0.000 description 1
- FZWBNHMXJMCXLU-UHFFFAOYSA-N 2,3,4,5-tetrahydroxy-6-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexanal Chemical compound OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OCC(O)C(O)C(O)C(O)C=O)O1 FZWBNHMXJMCXLU-UHFFFAOYSA-N 0.000 description 1
- AENZGWONVTXLRC-UHFFFAOYSA-N 2-(2,5-dioxopyrrol-1-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1C(=O)C=CC1=O AENZGWONVTXLRC-UHFFFAOYSA-N 0.000 description 1
- CYWHLOXWVAWMFO-UHFFFAOYSA-N 3-sulfanyl-1h-pyridine-2-thione Chemical compound SC1=CC=CN=C1S CYWHLOXWVAWMFO-UHFFFAOYSA-N 0.000 description 1
- UHBAPGWWRFVTFS-UHFFFAOYSA-N 4,4'-dipyridyl disulfide Chemical compound C=1C=NC=CC=1SSC1=CC=NC=C1 UHBAPGWWRFVTFS-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 108090000526 Papain Proteins 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 208000012322 Raynaud phenomenon Diseases 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 101710182532 Toxin a Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- ZHAFUINZIZIXFC-UHFFFAOYSA-N [9-(dimethylamino)-10-methylbenzo[a]phenoxazin-5-ylidene]azanium;chloride Chemical compound [Cl-].O1C2=CC(=[NH2+])C3=CC=CC=C3C2=NC2=C1C=C(N(C)C)C(C)=C2 ZHAFUINZIZIXFC-UHFFFAOYSA-N 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 239000003948 anatoxin Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
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- KIWQWJKWBHZMDT-UHFFFAOYSA-N homocysteine thiolactone Chemical compound NC1CCSC1=O KIWQWJKWBHZMDT-UHFFFAOYSA-N 0.000 description 1
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- 208000018389 neoplasm of cerebral hemisphere Diseases 0.000 description 1
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- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
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- 229940055729 papain Drugs 0.000 description 1
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- 229920002866 paraformaldehyde Polymers 0.000 description 1
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- 230000000607 poisoning effect Effects 0.000 description 1
- 238000009597 pregnancy test Methods 0.000 description 1
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- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
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- HHLJUSLZGFYWKW-UHFFFAOYSA-N triethanolamine hydrochloride Chemical compound Cl.OCCN(CCO)CCO HHLJUSLZGFYWKW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K19/00—Hybrid peptides, i.e. peptides covalently bound to nucleic acids, or non-covalently bound protein-protein complexes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/385—Haptens or antigens, bound to carriers
-
- 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
- A61K47/62—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 a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
- A61K47/6415—Toxins or lectins, e.g. clostridial toxins or Pseudomonas exotoxins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- 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
- C07K14/33—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria from Clostridium (G)
-
- 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
- C07K14/34—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from bacteria from Corynebacterium (G)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
- A61K2039/6031—Proteins
- A61K2039/6037—Bacterial toxins, e.g. diphteria toxoid [DT], tetanus toxoid [TT]
-
- 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)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Biophysics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Toxicology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7929.289 | 1979-11-28 | ||
| FR7929289A FR2470773B1 (enrdf_load_stackoverflow) | 1979-11-28 | 1979-11-28 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000425262A Division CA1178949A (en) | 1979-11-28 | 1983-04-05 | Thiolated polypeptide compound derived from a tetanus toxin fragment, the process for obtaining and its applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1152493A true CA1152493A (en) | 1983-08-23 |
Family
ID=9232177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000365671A Expired CA1152493A (en) | 1979-11-28 | 1980-11-27 | Thiolated polypeptide compound derived from a tetanus toxin fragment, the process for obtaining and its applications |
Country Status (5)
| Country | Link |
|---|---|
| EP (2) | EP0065320B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5690097A (enrdf_load_stackoverflow) |
| CA (1) | CA1152493A (enrdf_load_stackoverflow) |
| ES (2) | ES8202831A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2470773B1 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7435792B2 (en) | 1997-08-14 | 2008-10-14 | Institut Pasteur | Hybrid proteins that migrate retrogradely and transynaptically into the CNS |
| US7923015B2 (en) | 1997-08-14 | 2011-04-12 | Institut Pasteur | Methods for direct visualization of active synapses |
| US7923216B2 (en) | 1997-08-14 | 2011-04-12 | Institut Pasteur | In vivo modulation of neuronal transport |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2498192A2 (fr) * | 1981-01-22 | 1982-07-23 | Pasteur Institut | Nouveau compose polypeptidique thiole provenant d'un fragment de la toxine tetanique, son procede d'obtention et ses applications |
| SE8102193L (sv) * | 1981-04-06 | 1982-10-07 | Pharmacia Ab | Terapeutiskt aktiv organisk forening och dess anvendning |
| GB8334499D0 (en) * | 1983-12-24 | 1984-02-01 | Beecham Group Plc | Derivatives |
| CA2109527A1 (en) * | 1991-05-03 | 1992-11-04 | Elaine Tuomanen | Amino-acid sequence homologies between selectins and b pertussis toxin-peptides derived therefrom, antibodies thereto and pharmaceutical compositions |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3171831A (en) * | 1961-02-14 | 1965-03-02 | Schwarz Biores Inc | Thiolation of proteins by reaction with homocysteine thiolactone in the presence of tertiary amine |
| DE1617880A1 (de) * | 1966-10-06 | 1971-07-22 | Karl Dr Med Theurer | Verfahren zur Gewinnung von organotropen,bioaktiven Wirkstoffen,insbesondere von Arzneimitteln |
| FR2270891A2 (en) * | 1974-05-15 | 1975-12-12 | Anvar | Vaccines by glutaraldehyde detoxification - especially multivalent vaccines e.g. against tetanus and diphtheria |
| IN140168B (enrdf_load_stackoverflow) * | 1974-10-14 | 1976-09-25 | All India Inst Med | |
| JPS5272284A (en) * | 1975-12-12 | 1977-06-16 | Dainippon Pharmaceutical Co | Enzymeeimmunoassay reagent |
| JPS5341420A (en) * | 1976-09-29 | 1978-04-14 | Mochida Pharm Co Ltd | Immunochemically measuring methoa of hapten |
| SE427505B (sv) * | 1977-03-04 | 1983-04-11 | Pharmacia Diagnostics Ab | Reagens till anvendning vid immunkemiska bestemningsmetoder |
| US4234561A (en) * | 1978-02-06 | 1980-11-18 | Research Corporation | Antigen for early pregnancy test and contraceptive vaccine |
-
1979
- 1979-11-28 FR FR7929289A patent/FR2470773B1/fr not_active Expired
-
1980
- 1980-11-27 ES ES497182A patent/ES8202831A1/es not_active Expired
- 1980-11-27 CA CA000365671A patent/CA1152493A/en not_active Expired
- 1980-11-28 JP JP16683380A patent/JPS5690097A/ja active Pending
- 1980-11-28 EP EP82105526A patent/EP0065320B1/fr not_active Expired
- 1980-11-28 EP EP80401708A patent/EP0030496B1/fr not_active Expired
-
1981
- 1981-12-01 ES ES507625A patent/ES507625A0/es active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7435792B2 (en) | 1997-08-14 | 2008-10-14 | Institut Pasteur | Hybrid proteins that migrate retrogradely and transynaptically into the CNS |
| US7923015B2 (en) | 1997-08-14 | 2011-04-12 | Institut Pasteur | Methods for direct visualization of active synapses |
| US7923216B2 (en) | 1997-08-14 | 2011-04-12 | Institut Pasteur | In vivo modulation of neuronal transport |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2470773A1 (enrdf_load_stackoverflow) | 1981-06-12 |
| ES8400460A1 (es) | 1983-10-16 |
| EP0065320B1 (fr) | 1985-04-03 |
| FR2470773B1 (enrdf_load_stackoverflow) | 1983-01-28 |
| ES497182A0 (es) | 1982-03-01 |
| ES507625A0 (es) | 1983-10-16 |
| EP0065320A1 (fr) | 1982-11-24 |
| EP0030496A1 (fr) | 1981-06-17 |
| EP0030496B1 (fr) | 1983-07-13 |
| JPS5690097A (en) | 1981-07-21 |
| ES8202831A1 (es) | 1982-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |