RU1828401C - Способ получени противоопухолевого средства - Google Patents
Способ получени противоопухолевого средстваInfo
- Publication number
- RU1828401C RU1828401C SU4831830A SU4831830A RU1828401C RU 1828401 C RU1828401 C RU 1828401C SU 4831830 A SU4831830 A SU 4831830A SU 4831830 A SU4831830 A SU 4831830A RU 1828401 C RU1828401 C RU 1828401C
- Authority
- RU
- Russia
- Prior art keywords
- solution
- aqueous solution
- bis
- zinc
- hydroxybenzoate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 230000000259 anti-tumor effect Effects 0.000 title 1
- 239000000243 solution Substances 0.000 claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 239000003381 stabilizer Substances 0.000 claims abstract description 5
- 229960001763 zinc sulfate Drugs 0.000 claims abstract description 4
- 229910000368 zinc sulfate Inorganic materials 0.000 claims abstract description 4
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 6
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 5
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 5
- 229960003415 propylparaben Drugs 0.000 claims description 5
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 6
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229930013930 alkaloid Natural products 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- AQTQHPDCURKLKT-JKDPCDLQSA-N vincristine sulfate Chemical compound OS(O)(=O)=O.C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 AQTQHPDCURKLKT-JKDPCDLQSA-N 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- 239000011701 zinc Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 0.000 description 5
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 229960004494 calcium gluconate Drugs 0.000 description 4
- 239000004227 calcium gluconate Substances 0.000 description 4
- 235000013927 calcium gluconate Nutrition 0.000 description 4
- NEEHYRZPVYRGPP-UHFFFAOYSA-L calcium;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O NEEHYRZPVYRGPP-UHFFFAOYSA-L 0.000 description 4
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 4
- TYGUTURXHKSOBP-UHFFFAOYSA-N 10-bromo-5,12-dihydroindolo[2,3-g]carbazole-2,3-diol Chemical compound C1=C(Br)C=C2NC3=C(C4=C(C=C(C(=C4)O)O)N4)C4=CC=C3C2=C1 TYGUTURXHKSOBP-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940040682 calcium gluconate monohydrate Drugs 0.000 description 3
- XLNFVCRGJZBQGX-XRDLMGPZSA-L calcium;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate;hydrate Chemical compound O.[Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O XLNFVCRGJZBQGX-XRDLMGPZSA-L 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229940102223 injectable solution Drugs 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000001755 magnesium gluconate Substances 0.000 description 3
- 229960003035 magnesium gluconate Drugs 0.000 description 3
- 235000015778 magnesium gluconate Nutrition 0.000 description 3
- 229960000306 zinc gluconate Drugs 0.000 description 3
- 235000011478 zinc gluconate Nutrition 0.000 description 3
- 239000011670 zinc gluconate Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WHMDKBIGKVEYHS-IYEMJOQQSA-L Zinc gluconate Chemical compound [Zn+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O WHMDKBIGKVEYHS-IYEMJOQQSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229950001104 anhydrovinblastine Drugs 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000008196 pharmacological composition Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 2
- 229960002110 vincristine sulfate Drugs 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000001465 calcium Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IAKLPCRFBAZVRW-XRDLMGPZSA-L magnesium;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate;hydrate Chemical compound O.[Mg+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O IAKLPCRFBAZVRW-XRDLMGPZSA-L 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
- 229960004982 vinblastine sulfate Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Press Drives And Press Lines (AREA)
- Press-Shaping Or Shaping Using Conveyers (AREA)
- Powder Metallurgy (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU895804A HU204995B (en) | 1989-11-07 | 1989-11-07 | Process for producing pharmaceutical composition comprising alkaloid with bis-indole skeleton, with antitumour activity and suitable fr parenteral purposes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU1828401C true RU1828401C (ru) | 1993-07-15 |
Family
ID=10970758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU4831830A RU1828401C (ru) | 1989-11-07 | 1990-11-06 | Способ получени противоопухолевого средства |
Country Status (37)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4776843B2 (ja) | 1999-10-01 | 2011-09-21 | イムノゲン インコーポレーティッド | 免疫複合体及び化学療法剤を用いる癌治療用組成物及び方法 |
| JP2002100303A (ja) * | 2000-09-20 | 2002-04-05 | Hitachi Ltd | カラ−陰極線管 |
| US20050170015A1 (en) * | 2000-10-31 | 2005-08-04 | Brown Dennis M. | Antiproliferative colchicine compositions and uses thereof |
| FR2863891B1 (fr) * | 2003-12-23 | 2006-03-24 | Pf Medicament | Composition pharmaceutique de vinflunine destinee a une administration parentale, procede de preparation et utilisation |
| US20110015221A1 (en) * | 2003-12-23 | 2011-01-20 | Pierre Fabre Medicament | Pharmaceutical composition of vinflunine which is intended for parenteral administration preparation method thereof and use of same |
| US8512761B2 (en) * | 2006-01-27 | 2013-08-20 | Yale University | Fast acting inhibitor of gastric acid secretion |
| TWI678213B (zh) * | 2015-07-22 | 2019-12-01 | 美商史倍壯製藥公司 | 用於長春新鹼硫酸鹽脂質體注射之即可使用的調配物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD155034A1 (de) * | 1980-07-31 | 1982-05-12 | Uwe Olthoff | Verfahren zur herstellung stabiler kalziumhaltiger injektionsloesungen |
| IT1170152B (it) * | 1982-07-19 | 1987-06-03 | Lilly Co Eli | Miglioramenti a o riguardanti formulazioni di vinca-alcaloidi |
| US4619935A (en) * | 1983-03-17 | 1986-10-28 | Eli Lilly And Company | Stable oncolytic formulations |
| HU195513B (en) * | 1984-10-16 | 1988-05-30 | Richter Gedeon Vegyeszet | Process for producing stable solutions of alkaloides with bis-indole skeleton |
| FR2597750B1 (fr) * | 1986-04-25 | 1989-06-02 | Pf Medicament | Solution aqueuse stable de sulfate de vincristine |
| IL83086A (en) * | 1987-07-06 | 1991-03-10 | Teva Pharma | Stable,injectable solutions of vincristine salts |
| US4923876A (en) * | 1988-04-18 | 1990-05-08 | Cetus Corporation | Vinca alkaloid pharmaceutical compositions |
-
1989
- 1989-11-07 HU HU895804A patent/HU204995B/hu not_active IP Right Cessation
-
1990
- 1990-11-02 SK SK5402-90A patent/SK278421B6/sk unknown
- 1990-11-02 US US07/608,481 patent/US5397784A/en not_active Expired - Fee Related
- 1990-11-02 CZ CS905402A patent/CZ279433B6/cs not_active IP Right Cessation
- 1990-11-05 CH CH3499/90A patent/CH682130A5/de not_active IP Right Cessation
- 1990-11-05 ZA ZA908855A patent/ZA908855B/xx unknown
- 1990-11-06 DE DE4035253A patent/DE4035253B4/de not_active Expired - Fee Related
- 1990-11-06 IL IL9624990A patent/IL96249A/en unknown
- 1990-11-06 NL NL9002412A patent/NL9002412A/nl active Search and Examination
- 1990-11-06 IE IE399390A patent/IE62387B1/en not_active IP Right Cessation
- 1990-11-06 YU YU209590A patent/YU48373B/sh unknown
- 1990-11-06 AT AT0223090A patent/AT401469B/de not_active IP Right Cessation
- 1990-11-06 SE SE9003523A patent/SE509715C2/sv not_active IP Right Cessation
- 1990-11-06 DK DK266390A patent/DK266390A/da not_active Application Discontinuation
- 1990-11-06 UA UA4831830A patent/UA13162A/uk unknown
- 1990-11-06 RU SU4831830A patent/RU1828401C/ru active
- 1990-11-06 CA CA002029368A patent/CA2029368C/en not_active Expired - Fee Related
- 1990-11-06 NO NO904821A patent/NO175565C/no unknown
- 1990-11-06 PT PT95810A patent/PT95810B/pt active IP Right Grant
- 1990-11-06 IT IT06786890A patent/IT1242724B/it active IP Right Grant
- 1990-11-07 MY MYPI90001962A patent/MY104595A/en unknown
- 1990-11-07 AU AU65845/90A patent/AU638504B2/en not_active Ceased
- 1990-11-07 CN CN90109756A patent/CN1053569C/zh not_active Expired - Fee Related
- 1990-11-07 FI FI905508A patent/FI100455B/fi not_active IP Right Cessation
- 1990-11-07 NZ NZ236005A patent/NZ236005A/en unknown
- 1990-11-07 JP JP2300023A patent/JP3042702B2/ja not_active Expired - Fee Related
- 1990-11-07 PL PL90287663A patent/PL164881B1/pl not_active IP Right Cessation
- 1990-11-07 KR KR1019900017973A patent/KR0164601B1/ko not_active Expired - Fee Related
- 1990-11-07 AR AR90318325A patent/AR245592A1/es active
- 1990-11-07 BE BE9001046A patent/BE1004051A4/fr not_active IP Right Cessation
- 1990-11-07 BG BG93175A patent/BG60609B1/bg unknown
- 1990-11-07 GB GB9024222A patent/GB2238241B/en not_active Expired - Fee Related
- 1990-11-07 FR FR9013786A patent/FR2653998B1/fr not_active Expired - Fee Related
- 1990-11-07 ES ES9002834A patent/ES2026062A6/es not_active Expired - Lifetime
- 1990-11-07 GR GR900100795A patent/GR1001041B/el not_active IP Right Cessation
-
1993
- 1993-05-06 LT LTIP512A patent/LT3334B/lt not_active IP Right Cessation
- 1993-06-15 LV LVP-93-585A patent/LV10687B/en unknown
Non-Patent Citations (1)
| Title |
|---|
| Ни, 195513, кл. С 07 D 519/04, 1989. * |
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