DE2530954A1 - Sulfatierte saponinsalze, verfahren zur herstellung und arzneimittel - Google Patents
Sulfatierte saponinsalze, verfahren zur herstellung und arzneimittelInfo
- Publication number
- DE2530954A1 DE2530954A1 DE19752530954 DE2530954A DE2530954A1 DE 2530954 A1 DE2530954 A1 DE 2530954A1 DE 19752530954 DE19752530954 DE 19752530954 DE 2530954 A DE2530954 A DE 2530954A DE 2530954 A1 DE2530954 A1 DE 2530954A1
- Authority
- DE
- Germany
- Prior art keywords
- aescin
- acid ester
- salt
- psna
- sulfated
- 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.)
- Withdrawn
Links
- 239000001397 quillaja saponaria molina bark Substances 0.000 title description 4
- 229930182490 saponin Natural products 0.000 title description 4
- -1 SAPONIN SALT Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- YFESOSRPNPYODN-RSMWSHJLSA-N (2s,3s,4s,5r,6r)-6-[[(4s,6ar,6bs,8r,8ar,9r,10r,14br)-9-acetyloxy-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2s,3r,4s, Chemical class O([C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)OC1CC[C@]2(C)C3CC=C4[C@@]([C@@]3(CCC2[C@]1(CO)C)C)(C)C[C@@H](O)[C@@]1(CO)[C@@H](OC(C)=O)[C@@H](C(CC14)(C)C)OC(=O)C(\C)=C/C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.O([C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)OC1CC[C@]2(C)C3CC=C4[C@@]([C@@]3(CCC2[C@]1(CO)C)C)(C)C[C@@H](O)[C@@]1(CO)[C@@H](OC(C)=O)[C@@H](C(CC14)(C)C)OC(=O)C(/C)=C/C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YFESOSRPNPYODN-RSMWSHJLSA-N 0.000 claims description 23
- AXNVHPCVMSNXNP-GKTCLTPXSA-N Aescin Natural products O=C(O[C@H]1[C@@H](OC(=O)C)[C@]2(CO)[C@@H](O)C[C@@]3(C)[C@@]4(C)[C@@H]([C@]5(C)[C@H]([C@](CO)(C)[C@@H](O[C@@H]6[C@@H](O[C@H]7[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O7)[C@@H](O)[C@H](O[C@H]7[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O7)[C@@H](C(=O)O)O6)CC5)CC4)CC=C3[C@@H]2CC1(C)C)/C(=C/C)/C AXNVHPCVMSNXNP-GKTCLTPXSA-N 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 238000005670 sulfation reaction Methods 0.000 claims description 7
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 6
- 229940011399 escin Drugs 0.000 claims description 6
- 229930186222 escin Natural products 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 230000019635 sulfation Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 4
- 230000002785 anti-thrombosis Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229920000669 heparin Polymers 0.000 description 4
- 229960002897 heparin Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920001499 Heparinoid Polymers 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 210000002808 connective tissue Anatomy 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000002554 heparinoid Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000007949 saponins Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010018852 Haematoma Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 206010042674 Swelling Diseases 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000002322 anti-exudative effect Effects 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 235000010181 horse chestnut Nutrition 0.000 description 2
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 241000157282 Aesculus Species 0.000 description 1
- 241000157280 Aesculus hippocastanum Species 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000006395 Globulins Human genes 0.000 description 1
- 108010044091 Globulins Proteins 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 206010057267 Periphlebitis Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010042345 Subcutaneous haematoma Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000003724 cholesterol ester group Chemical group 0.000 description 1
- 239000001524 citrus aurantium oil Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 210000004177 elastic tissue Anatomy 0.000 description 1
- KHDOTPVDSFBNMG-UHFFFAOYSA-N ethanol;pyridine Chemical compound CCO.C1=CC=NC=C1 KHDOTPVDSFBNMG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 229940025770 heparinoids Drugs 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000017570 negative regulation of blood coagulation Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 208000001297 phlebitis Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229940046303 sodium cetostearyl sulfate Drugs 0.000 description 1
- CLBALUNQCMWJSU-UHFFFAOYSA-L sodium;hexadecyl sulfate;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O CLBALUNQCMWJSU-UHFFFAOYSA-L 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752530954 DE2530954A1 (de) | 1975-07-11 | 1975-07-11 | Sulfatierte saponinsalze, verfahren zur herstellung und arzneimittel |
| PT65300A PT65300B (de) | 1975-07-11 | 1976-06-30 | Sulfatierte saponisalze verfahren zur herstellung und arzneimittel |
| FI761956A FI761956A7 (enrdf_load_stackoverflow) | 1975-07-11 | 1976-07-05 | |
| BG033671A BG27377A3 (bg) | 1975-07-11 | 1976-07-05 | Метод за получаване на полисярнокисели естери на есцина |
| CS764472A CS193552B2 (en) | 1975-07-11 | 1976-07-06 | Process for preparing salts of escinpolysulphate |
| GB28231/76A GB1492023A (en) | 1975-07-11 | 1976-07-07 | Aescin polysulphuric acid esters |
| SU762378552A SU614741A3 (ru) | 1975-07-11 | 1976-07-07 | Способ получени эфиров эскинполисерной кислоты или их солей |
| YU01668/76A YU166876A (en) | 1975-07-11 | 1976-07-08 | Process for preparing escin esters of polysulfuric acids |
| AU15731/76A AU504838B2 (en) | 1975-07-11 | 1976-07-08 | Aescin polysulphuric acid esters |
| ZA764063A ZA764063B (en) | 1975-07-11 | 1976-07-08 | Improvements relating to sulphated saponin salts |
| CA256,652A CA1064904A (en) | 1975-07-11 | 1976-07-09 | Sulphated saponine salts, process for obtention and medicine |
| HU76MA2795A HU174602B (hu) | 1975-07-11 | 1976-07-09 | Sposob poluchenija sul'fatirovannykh solejj saponinov |
| RO7686930A RO70425A (ro) | 1975-07-11 | 1976-07-10 | Procedeu pentru prepararea esterului de escin polisulfatat |
| PL1976191112A PL99630B1 (pl) | 1975-07-11 | 1976-07-10 | Sposob wytwarzania soli estru kwasu aescynopolisiarkowego z farmakologicznie tolerowanymi zasadami |
| BE168850A BE844054A (fr) | 1975-07-11 | 1976-07-12 | Sels de saponine sulfates, procedes de fabrication de ces sels et leur application comme medicaments |
| PH18680A PH12629A (en) | 1975-07-11 | 1976-07-12 | Pharmacologically acceptable salts of aescin poly-sulphoric acid ester,method of preparing same and pharmaceutical composition containing same |
| JP51082844A JPS5236655A (en) | 1975-07-11 | 1976-07-12 | Production sulphated saponin salt and anti smearing agent containing same |
| FR7621312A FR2316960A1 (fr) | 1975-07-11 | 1976-07-12 | Sels de saponine sulfates, procedes de fabrication de ces sels et leur application comme medicaments |
| HK491/78A HK49178A (en) | 1975-07-11 | 1978-08-31 | Aescin polysulphuric acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752530954 DE2530954A1 (de) | 1975-07-11 | 1975-07-11 | Sulfatierte saponinsalze, verfahren zur herstellung und arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2530954A1 true DE2530954A1 (de) | 1977-01-27 |
Family
ID=5951226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752530954 Withdrawn DE2530954A1 (de) | 1975-07-11 | 1975-07-11 | Sulfatierte saponinsalze, verfahren zur herstellung und arzneimittel |
Country Status (19)
-
1975
- 1975-07-11 DE DE19752530954 patent/DE2530954A1/de not_active Withdrawn
-
1976
- 1976-06-30 PT PT65300A patent/PT65300B/pt unknown
- 1976-07-05 FI FI761956A patent/FI761956A7/fi not_active Application Discontinuation
- 1976-07-05 BG BG033671A patent/BG27377A3/xx unknown
- 1976-07-06 CS CS764472A patent/CS193552B2/cs unknown
- 1976-07-07 GB GB28231/76A patent/GB1492023A/en not_active Expired
- 1976-07-07 SU SU762378552A patent/SU614741A3/ru active
- 1976-07-08 AU AU15731/76A patent/AU504838B2/en not_active Expired
- 1976-07-08 ZA ZA764063A patent/ZA764063B/xx unknown
- 1976-07-08 YU YU01668/76A patent/YU166876A/xx unknown
- 1976-07-09 HU HU76MA2795A patent/HU174602B/hu unknown
- 1976-07-09 CA CA256,652A patent/CA1064904A/en not_active Expired
- 1976-07-10 RO RO7686930A patent/RO70425A/ro unknown
- 1976-07-10 PL PL1976191112A patent/PL99630B1/pl unknown
- 1976-07-12 BE BE168850A patent/BE844054A/xx unknown
- 1976-07-12 PH PH18680A patent/PH12629A/en unknown
- 1976-07-12 FR FR7621312A patent/FR2316960A1/fr active Granted
- 1976-07-12 JP JP51082844A patent/JPS5236655A/ja active Granted
-
1978
- 1978-08-31 HK HK491/78A patent/HK49178A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU614741A3 (ru) | 1978-07-05 |
| PT65300B (de) | 1977-12-13 |
| AU504838B2 (en) | 1979-11-01 |
| ZA764063B (en) | 1977-07-27 |
| BG27377A3 (bg) | 1979-10-12 |
| BE844054A (fr) | 1977-01-12 |
| HK49178A (en) | 1978-09-08 |
| GB1492023A (en) | 1977-11-16 |
| FR2316960B1 (enrdf_load_stackoverflow) | 1979-03-02 |
| CS193552B2 (en) | 1979-10-31 |
| PH12629A (en) | 1979-07-05 |
| PT65300A (de) | 1976-07-01 |
| CA1064904A (en) | 1979-10-23 |
| HU174602B (hu) | 1980-02-28 |
| FI761956A7 (enrdf_load_stackoverflow) | 1977-01-12 |
| FR2316960A1 (fr) | 1977-02-04 |
| JPS5614117B2 (enrdf_load_stackoverflow) | 1981-04-02 |
| YU166876A (en) | 1982-05-31 |
| JPS5236655A (en) | 1977-03-22 |
| RO70425A (ro) | 1980-12-30 |
| PL99630B1 (pl) | 1978-07-31 |
| AU1573176A (en) | 1978-01-12 |
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