CA1037028A - Watersoluble extracts of corynebacteria, process for obtaining them and their use - Google Patents
Watersoluble extracts of corynebacteria, process for obtaining them and their useInfo
- Publication number
- CA1037028A CA1037028A CA226,296A CA226296A CA1037028A CA 1037028 A CA1037028 A CA 1037028A CA 226296 A CA226296 A CA 226296A CA 1037028 A CA1037028 A CA 1037028A
- Authority
- CA
- Canada
- Prior art keywords
- watersoluble
- extracts
- fragments
- molecular weight
- corynebacteria
- 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
- 239000000284 extract Substances 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 32
- GMKMEZVLHJARHF-UHFFFAOYSA-N (2R,6R)-form-2.6-Diaminoheptanedioic acid Natural products OC(=O)C(N)CCCC(N)C(O)=O GMKMEZVLHJARHF-UHFFFAOYSA-N 0.000 claims abstract description 25
- GMKMEZVLHJARHF-SYDPRGILSA-N meso-2,6-diaminopimelic acid Chemical compound [O-]C(=O)[C@@H]([NH3+])CCC[C@@H]([NH3+])C([O-])=O GMKMEZVLHJARHF-SYDPRGILSA-N 0.000 claims abstract description 25
- 238000000605 extraction Methods 0.000 claims abstract description 11
- 230000001580 bacterial effect Effects 0.000 claims abstract description 7
- 241000186216 Corynebacterium Species 0.000 claims abstract description 6
- 239000012634 fragment Substances 0.000 claims description 18
- 235000000346 sugar Nutrition 0.000 claims description 9
- RADQQIMFQHYCBI-UHFFFAOYSA-N 6-[[4-[2-[2-[2-acetamido-4-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6-dihydroxy-1-oxohexan-3-yl]oxypropanoylamino]propanoylamino]-4-carboxybutanoyl]amino]-2-amino-7-(1-carboxyethylamino)-7-oxoheptanoic acid Chemical compound OC(=O)C(N)CCCC(C(=O)NC(C)C(O)=O)NC(=O)CCC(C(O)=O)NC(=O)C(C)NC(=O)C(C)OC(C(NC(C)=O)C=O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1NC(C)=O RADQQIMFQHYCBI-UHFFFAOYSA-N 0.000 claims description 8
- 108700033544 disaccharide tetrapeptide Proteins 0.000 claims description 8
- 239000013638 trimer Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000539 dimer Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 150000008163 sugars Chemical class 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 239000003599 detergent Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000005185 salting out Methods 0.000 claims description 4
- 239000006228 supernatant Substances 0.000 claims description 4
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 claims description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 3
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 238000000502 dialysis Methods 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 229920002401 polyacrylamide Polymers 0.000 claims 2
- 239000000568 immunological adjuvant Substances 0.000 abstract description 3
- 238000011197 physicochemical method Methods 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 11
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 7
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 5
- 235000004279 alanine Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 4
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 4
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 4
- 210000002421 cell wall Anatomy 0.000 description 4
- 235000013922 glutamic acid Nutrition 0.000 description 4
- 239000004220 glutamic acid Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229950006780 n-acetylglucosamine Drugs 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- 229960005261 aspartic acid Drugs 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 229960005486 vaccine Drugs 0.000 description 2
- MSFSPUZXLOGKHJ-PGYHGBPZSA-N 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucopyranose Chemical compound OC(=O)[C@@H](C)O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O MSFSPUZXLOGKHJ-PGYHGBPZSA-N 0.000 description 1
- SATHPVQTSSUFFW-UHFFFAOYSA-N 4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol Chemical compound OC1C(OC)C(O)COC1OCC1C(O)C(OC)C(O)C(OC2C(C(CO)OC(C)C2O)O)O1 SATHPVQTSSUFFW-UHFFFAOYSA-N 0.000 description 1
- 240000000736 Amomum maximum Species 0.000 description 1
- 241001046548 Anaerobium Species 0.000 description 1
- 229920000189 Arabinogalactan Polymers 0.000 description 1
- 239000001904 Arabinogalactan Substances 0.000 description 1
- 241000490494 Arabis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000237074 Centris Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241001517310 Eria Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 241000370541 Idia Species 0.000 description 1
- 229920006063 Lamide® Polymers 0.000 description 1
- 241000100287 Membras Species 0.000 description 1
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 1
- MNLRQHMNZILYPY-MDMHTWEWSA-N N-acetyl-alpha-D-muramic acid Chemical compound OC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O)[C@@H]1NC(C)=O MNLRQHMNZILYPY-MDMHTWEWSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000019312 arabinogalactan Nutrition 0.000 description 1
- 229960002319 barbital Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- 239000000850 decongestant Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000015961 delipidation Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/66—Microorganisms or materials therefrom
- A61K35/74—Bacteria
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
- C12P1/04—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes by using bacteria
-
- 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
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
- A61K2039/55516—Proteins; Peptides
-
- 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
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55588—Adjuvants of undefined constitution
- A61K2039/55594—Adjuvants of undefined constitution from bacteria
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/15—Corynebacterium
-
- 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
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/27—Cyclic peptide or cyclic protein
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Mycology (AREA)
- Biotechnology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Immunology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7415570A FR2269961B1 (en, 2012) | 1974-05-06 | 1974-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1037028A true CA1037028A (en) | 1978-08-22 |
Family
ID=9138474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,296A Expired CA1037028A (en) | 1974-05-06 | 1975-05-05 | Watersoluble extracts of corynebacteria, process for obtaining them and their use |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4013788A (en, 2012) |
| JP (1) | JPS50155685A (en, 2012) |
| BE (1) | BE828635A (en, 2012) |
| CA (1) | CA1037028A (en, 2012) |
| CH (1) | CH604725A5 (en, 2012) |
| CS (1) | CS196267B2 (en, 2012) |
| DE (1) | DE2519938A1 (en, 2012) |
| DK (1) | DK194975A (en, 2012) |
| FR (1) | FR2269961B1 (en, 2012) |
| GB (1) | GB1502320A (en, 2012) |
| IL (1) | IL47205A (en, 2012) |
| NL (1) | NL7505246A (en, 2012) |
| SE (1) | SE7505032L (en, 2012) |
| SU (1) | SU727112A3 (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2320107A1 (fr) * | 1975-08-05 | 1977-03-04 | Anvar | Nouveaux adjuvants immunologiques, procede pour leur obtention et compositions les contenant |
| FR2321896A1 (fr) * | 1975-08-29 | 1977-03-25 | Anvar | Agents adjuvants immunologiques actifs en solution aqueuse |
| US4148877A (en) * | 1975-12-29 | 1979-04-10 | Choay S. A. | Fraction capable of inducing in vivo a resistance to bacterial infections, process for obtaining said fraction from bacteria and drugs containing said fraction |
| FR2374042A1 (fr) * | 1976-06-04 | 1978-07-13 | Merieux Inst | Nouveau medicament immunostimulant et son procede de preparation |
| FR2378855A1 (fr) * | 1977-01-27 | 1978-08-25 | Cassenne Lab Sa | Nouvelles glycoproteines isolees d'hafnia, procede de preparation et application a titre de medicaments |
| GB1598457A (en) * | 1977-03-22 | 1981-09-23 | Glaxo Lab Ltd | Process for the preparation of a fraction containing peptidoglycan material from streptomyces griseus |
| JPS58874B2 (ja) * | 1979-08-30 | 1983-01-08 | 株式会社 目黒研究所 | 糖蛋白ｗｅｎａｃ及びその製造法 |
| DE3011461C2 (de) * | 1980-03-25 | 1986-10-30 | Dr. Madaus & Co, 5000 Köln | Verwendung von Propionibakterien |
| FR2480604A1 (fr) * | 1980-04-22 | 1981-10-23 | Pasteur Institut | Fractions nouvelles extraites de bacteries aerobies, douees de proprietes antitumorales, antibacteriennes et inductrices d'interferon et leur procede de preparation |
| US4479935A (en) * | 1980-04-22 | 1984-10-30 | Institut Pasteur | Fractions extracted from aerobic bacteria, endowed with antitumoral, antibacterial and interferon inducing properties, and process for their preparation |
| FR2490496A1 (fr) * | 1980-09-19 | 1982-03-26 | Roussel Uclaf | Nouvelles glycoproteines immunostimulantes extraites de klebsiella pneumoniae, leur procede d'obtention, leur application a titre de medicaments et les compositions les renfermant |
| FR2490495A1 (fr) * | 1980-09-19 | 1982-03-26 | Roussel Uclaf | Nouvelles glycoproteines hydrosolubles immunostimulantes extraites de klebsiella pneumoniae, leur procede d'obtention, leur application a titre de medicaments et les compositions les renfermant |
| JPS57163835U (en, 2012) * | 1981-04-07 | 1982-10-15 | ||
| JPH0742310B2 (ja) * | 1984-01-23 | 1995-05-10 | 味の素株式会社 | Ｌ−アスパルチル−ｌ−フエニルアラニン又はその低級アルキルエステルの晶析法 |
| IT1237903B (it) * | 1989-12-14 | 1993-06-18 | Medidom Lab | Derivati semisintetici ad attivita' immunomodulante atti alla somminitrazione parenterale ed orale |
| WO1994016727A1 (en) * | 1993-01-29 | 1994-08-04 | Vetrepharm, Inc. | Immunotherapeutic composition |
| US5976580A (en) | 1995-06-07 | 1999-11-02 | Novus International, Inc. | Nutrient formulation and process for enhancing the health, livability, cumulative weight gain or feed efficiency in poultry and other animals |
| JP4759182B2 (ja) * | 2001-08-03 | 2011-08-31 | 花王株式会社 | 水溶性ショウキョウエキス |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2189021A1 (en) | 1972-06-20 | 1974-01-25 | Anvar | Non-arthrogenic immunological adjuvants - obtained by extraction of lipid-free mycobacterial residues |
-
1974
- 1974-05-06 FR FR7415570A patent/FR2269961B1/fr not_active Expired
-
1975
- 1975-04-29 SE SE7505032A patent/SE7505032L/xx unknown
- 1975-04-30 IL IL47205A patent/IL47205A/xx unknown
- 1975-04-30 BE BE155997A patent/BE828635A/xx unknown
- 1975-04-30 US US05/573,200 patent/US4013788A/en not_active Expired - Lifetime
- 1975-05-02 JP JP50052653A patent/JPS50155685A/ja active Pending
- 1975-05-02 NL NL7505246A patent/NL7505246A/xx not_active Application Discontinuation
- 1975-05-05 DK DK194975A patent/DK194975A/da unknown
- 1975-05-05 SU SU752131288A patent/SU727112A3/ru active
- 1975-05-05 CH CH577475A patent/CH604725A5/xx not_active IP Right Cessation
- 1975-05-05 DE DE19752519938 patent/DE2519938A1/de active Pending
- 1975-05-05 CA CA226,296A patent/CA1037028A/en not_active Expired
- 1975-05-05 GB GB18754/75A patent/GB1502320A/en not_active Expired
- 1975-05-05 CS CS753097A patent/CS196267B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL47205A (en) | 1978-06-15 |
| GB1502320A (en) | 1978-03-01 |
| SU727112A3 (ru) | 1980-04-05 |
| FR2269961A1 (en, 2012) | 1975-12-05 |
| US4013788A (en) | 1977-03-22 |
| CH604725A5 (en, 2012) | 1978-09-15 |
| DE2519938A1 (de) | 1975-11-27 |
| BE828635A (fr) | 1975-10-30 |
| CS196267B2 (en) | 1980-03-31 |
| SE7505032L (sv) | 1975-11-07 |
| JPS50155685A (en, 2012) | 1975-12-16 |
| NL7505246A (nl) | 1975-11-10 |
| IL47205A0 (en) | 1975-06-25 |
| DK194975A (da) | 1975-11-07 |
| FR2269961B1 (en, 2012) | 1978-03-24 |
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