SU1403990A3 - Способ получени полисахаридов - Google Patents
Способ получени полисахаридов Download PDFInfo
- Publication number
- SU1403990A3 SU1403990A3 SU782574401A SU2574401A SU1403990A3 SU 1403990 A3 SU1403990 A3 SU 1403990A3 SU 782574401 A SU782574401 A SU 782574401A SU 2574401 A SU2574401 A SU 2574401A SU 1403990 A3 SU1403990 A3 SU 1403990A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- stage
- serving
- silt
- amount
- glu
- Prior art date
Links
- 150000004676 glycans Chemical class 0.000 title claims abstract description 42
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 42
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims description 20
- 238000000605 extraction Methods 0.000 claims abstract description 8
- 241000222356 Coriolus Species 0.000 claims abstract description 4
- 238000000108 ultra-filtration Methods 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 16
- 239000000284 extract Substances 0.000 claims description 15
- 238000001223 reverse osmosis Methods 0.000 claims description 12
- 239000006286 aqueous extract Substances 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 11
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 10
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000005185 salting out Methods 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- 230000002538 fungal effect Effects 0.000 claims description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 150000001720 carbohydrates Chemical class 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 4
- 230000002441 reversible effect Effects 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 241000222355 Trametes versicolor Species 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000005342 ion exchange Methods 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 claims 14
- 239000012141 concentrate Substances 0.000 claims 4
- 241000196324 Embryophyta Species 0.000 claims 2
- 238000011210 chromatographic step Methods 0.000 claims 2
- 238000011010 flushing procedure Methods 0.000 claims 2
- ORKBYCQJWQBPFG-WOMZHKBXSA-N (8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 ORKBYCQJWQBPFG-WOMZHKBXSA-N 0.000 claims 1
- 235000003385 Diospyros ebenum Nutrition 0.000 claims 1
- 241000792913 Ebenaceae Species 0.000 claims 1
- 229910000831 Steel Inorganic materials 0.000 claims 1
- 244000299492 Thespesia populnea Species 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 239000010959 steel Substances 0.000 claims 1
- 241000221198 Basidiomycota Species 0.000 abstract 1
- 241000222341 Polyporaceae Species 0.000 abstract 1
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 34
- 239000000243 solution Substances 0.000 description 23
- 238000002474 experimental method Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000001963 growth medium Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000008103 glucose Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 238000006140 methanolysis reaction Methods 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- -1 saccharide compound Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- JVIPLYCGEZUBIO-UHFFFAOYSA-N 2-(4-fluorophenyl)-1,3-dioxoisoindole-5-carboxylic acid Chemical compound O=C1C2=CC(C(=O)O)=CC=C2C(=O)N1C1=CC=C(F)C=C1 JVIPLYCGEZUBIO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 229920001425 Diethylaminoethyl cellulose Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- PWBXSZOZBWBLEW-BZNPZCIMSA-N (2r,3s,4r,5r)-4,5-dihydroxy-2,3,6-trimethoxyhexanal Chemical compound COC[C@@H](O)[C@@H](O)[C@H](OC)[C@@H](OC)C=O PWBXSZOZBWBLEW-BZNPZCIMSA-N 0.000 description 1
- LOODZAPIPITKBN-BZNPZCIMSA-N (2r,3s,4r,5r)-5,6-dihydroxy-2,3,4-trimethoxyhexanal Chemical compound CO[C@@H](C=O)[C@@H](OC)[C@H](OC)[C@H](O)CO LOODZAPIPITKBN-BZNPZCIMSA-N 0.000 description 1
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 description 1
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 description 1
- LXJBARMBDDODTG-UHFFFAOYSA-N UNPD127318 Natural products COCC1OC(O)C(OC)C(OC)C1O LXJBARMBDDODTG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002303 glucose derivatives Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 238000005303 weighing Methods 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Microbiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP727277A JPS5394012A (en) | 1977-01-27 | 1977-01-27 | Novel polysaccharide and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1403990A3 true SU1403990A3 (ru) | 1988-06-15 |
Family
ID=11661383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782574401A SU1403990A3 (ru) | 1977-01-27 | 1978-01-26 | Способ получени полисахаридов |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5394012A (enExample) |
| AU (1) | AU501257B1 (enExample) |
| CA (1) | CA1086720A (enExample) |
| DE (1) | DE2803681A1 (enExample) |
| FR (1) | FR2378799A1 (enExample) |
| GB (1) | GB1581315A (enExample) |
| IT (1) | IT1112608B (enExample) |
| SU (1) | SU1403990A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2134694C1 (ru) * | 1994-12-30 | 1999-08-20 | Чонг Кун Данг Корпорейшн | Аминоолигосахарид ск-4416, способ его получения, ингибитор сахаридгидролазы и антибактериальный агент |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5461112A (en) * | 1977-10-24 | 1979-05-17 | Ono Pharmaceut Co Ltd | Oncostatic polysaccharide* its preparation* and oncostatic drugs containing it as an effective component |
| JPS5712999A (en) * | 1980-06-25 | 1982-01-22 | Chiyokichi Iizuka | Antibiral agent and its preparation |
| EP0049012B1 (en) * | 1980-09-29 | 1985-11-06 | Shell Internationale Researchmaatschappij B.V. | Treatment of pseudoplastic polysaccharide solutions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE757248A (fr) * | 1969-10-15 | 1971-04-08 | Kureha Chemical Ind Co Ltd | Substance a propriete anticancereuse et procedes pour sa preparation |
| JPS536413A (en) * | 1976-07-07 | 1978-01-20 | Kureha Chem Ind Co Ltd | Preparation of n-containing polysaccharides |
| JPS536412A (en) * | 1976-07-07 | 1978-01-20 | Kureha Chem Ind Co Ltd | Preparation of n-containing polysaccharides |
| JPS5315495A (en) * | 1976-07-22 | 1978-02-13 | Kureha Chem Ind Co Ltd | Preparation of polysaccharides |
-
1977
- 1977-01-27 JP JP727277A patent/JPS5394012A/ja active Granted
-
1978
- 1978-01-16 CA CA295,008A patent/CA1086720A/en not_active Expired
- 1978-01-18 AU AU32521/78A patent/AU501257B1/en not_active Expired
- 1978-01-26 SU SU782574401A patent/SU1403990A3/ru active
- 1978-01-26 GB GB3251/78A patent/GB1581315A/en not_active Expired
- 1978-01-27 DE DE19782803681 patent/DE2803681A1/de active Granted
- 1978-01-27 IT IT19741/78A patent/IT1112608B/it active
- 1978-01-27 FR FR7802325A patent/FR2378799A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2134694C1 (ru) * | 1994-12-30 | 1999-08-20 | Чонг Кун Данг Корпорейшн | Аминоолигосахарид ск-4416, способ его получения, ингибитор сахаридгидролазы и антибактериальный агент |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2803681C2 (enExample) | 1989-03-16 |
| CA1086720A (en) | 1980-09-30 |
| IT1112608B (it) | 1986-01-20 |
| JPS5394012A (en) | 1978-08-17 |
| JPS5646481B2 (enExample) | 1981-11-04 |
| FR2378799A1 (fr) | 1978-08-25 |
| DE2803681A1 (de) | 1978-08-17 |
| FR2378799B1 (enExample) | 1980-09-05 |
| AU501257B1 (en) | 1979-06-14 |
| GB1581315A (en) | 1980-12-10 |
| IT7819741A0 (it) | 1978-01-27 |
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