SU1375140A3 - Способ получени производных цефалоспорина или их аддитивных солей с галоидводородными кислотами - Google Patents
Способ получени производных цефалоспорина или их аддитивных солей с галоидводородными кислотами Download PDFInfo
- Publication number
- SU1375140A3 SU1375140A3 SU864018257A SU4018257A SU1375140A3 SU 1375140 A3 SU1375140 A3 SU 1375140A3 SU 864018257 A SU864018257 A SU 864018257A SU 4018257 A SU4018257 A SU 4018257A SU 1375140 A3 SU1375140 A3 SU 1375140A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- doublet
- amino
- singlet
- multiplet
- acid
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 7
- 239000002253 acid Substances 0.000 title claims description 16
- 229930186147 Cephalosporin Natural products 0.000 title claims description 4
- 229940124587 cephalosporin Drugs 0.000 title claims description 4
- 150000001780 cephalosporins Chemical class 0.000 title claims description 4
- 150000007513 acids Chemical class 0.000 title claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 title claims 2
- 239000012433 hydrogen halide Substances 0.000 title claims 2
- 239000000654 additive Chemical class 0.000 title description 3
- 230000000996 additive effect Effects 0.000 title description 3
- -1 amino, formylamino, aminomethyl Chemical group 0.000 claims description 47
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 229910019854 Ru—N Inorganic materials 0.000 description 29
- 239000008363 phosphate buffer Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000000843 powder Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 235000011167 hydrochloric acid Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 2
- 229960000603 cefalotin Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- KPGQMAZFCDQQQK-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl chloride Chemical compound CON=C(C(Cl)=O)C1=NSC(N)=N1 KPGQMAZFCDQQQK-UHFFFAOYSA-N 0.000 description 1
- PPCNPSIFJFHCJK-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-prop-2-enoxyiminoacetyl chloride Chemical compound NC1=NC(C(=NOCC=C)C(Cl)=O)=NS1 PPCNPSIFJFHCJK-UHFFFAOYSA-N 0.000 description 1
- ADDCQPMHFGZEFZ-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-prop-2-ynoxyiminoacetyl chloride;hydrochloride Chemical compound Cl.NC1=NC(C(=NOCC#C)C(Cl)=O)=NS1 ADDCQPMHFGZEFZ-UHFFFAOYSA-N 0.000 description 1
- MIHIJWOEDDPOLG-UHFFFAOYSA-N 2-methoxyiminoacetic acid Chemical compound CON=CC(O)=O MIHIJWOEDDPOLG-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 239000004484 Briquette Substances 0.000 description 1
- 102220615380 Centrosomal protein 20_I53Q_mutation Human genes 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 101000579646 Penaeus vannamei Penaeidin-1 Proteins 0.000 description 1
- URHBZAZPIZGEOQ-UHFFFAOYSA-N [3-(c-carbonochloridoyl-n-ethoxycarbonimidoyl)-1,2,4-thiadiazol-5-yl]azanium;chloride Chemical compound Cl.CCON=C(C(Cl)=O)C1=NSC(N)=N1 URHBZAZPIZGEOQ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- URDNYFBXXCIKJX-SECBINFHSA-N prop-1-enyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C(=CC)OC(=O)C1=CCS[C@H]2N1C(C2)=O URDNYFBXXCIKJX-SECBINFHSA-N 0.000 description 1
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59794184A | 1984-04-09 | 1984-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1375140A3 true SU1375140A3 (ru) | 1988-02-15 |
Family
ID=24393575
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU864018257A SU1375140A3 (ru) | 1984-04-09 | 1986-02-06 | Способ получени производных цефалоспорина или их аддитивных солей с галоидводородными кислотами |
| SU864023036A SU1367858A3 (ru) | 1984-04-09 | 1986-02-06 | Способ получени производных цефалоспорина |
| SU864019975A SU1487814A3 (ru) | 1984-04-09 | 1986-02-06 | СПОСОБ ПОЛУЧЕНИЯ 7-АМИНО-З-[3(4-КАРБАМОИЛ-1-ПИРИДИНИО)-1-ПРОПЕН1-ИЛ]-3-ЦЕФЕМ-4-КАРБОКСИЛАТА ч. |
| SU864020682A SU1436882A3 (ru) | 1984-04-09 | 1986-02-06 | Способ получени дифенилметилового эфира 7-бензилиденамино-3-(3-хлор-1-пропен-1-ил)-3-цефем-4-карбоновой кислоты |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU864023036A SU1367858A3 (ru) | 1984-04-09 | 1986-02-06 | Способ получени производных цефалоспорина |
| SU864019975A SU1487814A3 (ru) | 1984-04-09 | 1986-02-06 | СПОСОБ ПОЛУЧЕНИЯ 7-АМИНО-З-[3(4-КАРБАМОИЛ-1-ПИРИДИНИО)-1-ПРОПЕН1-ИЛ]-3-ЦЕФЕМ-4-КАРБОКСИЛАТА ч. |
| SU864020682A SU1436882A3 (ru) | 1984-04-09 | 1986-02-06 | Способ получени дифенилметилового эфира 7-бензилиденамино-3-(3-хлор-1-пропен-1-ил)-3-цефем-4-карбоновой кислоты |
Country Status (31)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61145186A (ja) * | 1984-12-20 | 1986-07-02 | Meiji Seika Kaisha Ltd | 新規セフエム化合物及びその製造法 |
| US4708955A (en) * | 1985-06-24 | 1987-11-24 | Bristol-Myers Company | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
| WO1987003875A1 (fr) * | 1985-12-26 | 1987-07-02 | Eisai Co., Ltd. | Derives de cephalosporine |
| AU614723B2 (en) * | 1986-10-13 | 1991-09-12 | Eisai Co. Ltd. | 3-propenylcephem derivative |
| IL84128A (en) * | 1986-10-13 | 1992-12-01 | Eisai Co Ltd | 3-propenylcephem derivatives, their preparation and pharmaceutical compositions containing them |
| JPH085897B2 (ja) * | 1986-11-06 | 1996-01-24 | エーザイ株式会社 | ３−プロペニルセフェム誘導体 |
| FR2622585B1 (fr) * | 1987-11-03 | 1991-04-19 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 3 un radical vinyle substitue, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus |
| EP0764648B1 (en) * | 1988-03-16 | 2002-01-16 | Eisai Co., Ltd. | Cephem derivatives and process for the preparation thereof |
| JPH0699449B2 (ja) * | 1988-03-16 | 1994-12-07 | エーザイ株式会社 | セフェム誘導体の合成中間体 |
| FR2655042B1 (fr) * | 1989-11-29 | 1994-01-21 | Adir Cie | Nouvelles benzothiazolinones substituees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2663332B1 (fr) * | 1990-06-15 | 1997-11-07 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 3 un radical propenyle substitue par un ammonium quaternaire, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus. |
| US5126336A (en) * | 1990-08-23 | 1992-06-30 | Bristol-Myers Squibb Company | Antibiotic c-3 catechol-substituted cephalosporin compounds, compositions and method of use thereof |
| AT396108B (de) * | 1991-08-21 | 1993-06-25 | Biochemie Gmbh | Neues verfahren und neue zwischenprodukte zur herstellung von 7-aminocephalosporansaeurederivaten |
| JPH0741484A (ja) * | 1993-07-29 | 1995-02-10 | Katayama Seiyakushiyo:Kk | セフェム化合物及び抗菌剤 |
| WO1996005205A1 (en) * | 1994-08-16 | 1996-02-22 | Meiji Seika Kabushiki Kaisha | Novel cephem derivative |
| AU761450B2 (en) | 1998-06-22 | 2003-06-05 | Basilea Pharmaceutica Ag | Propenyl cephalosporin derivatives |
| CN100398547C (zh) | 2003-09-09 | 2008-07-02 | 日本化学工业株式会社 | 3-氯甲基-3-头孢烯衍生物的制造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1342241A (en) * | 1970-01-23 | 1974-01-03 | Glaxo Lab Ltd | Cephalosporin compounds |
| US4390534A (en) * | 1978-12-29 | 1983-06-28 | Fujisawa Pharmaceutical Co., Ltd. | Cephem and cepham compounds |
| EP0025017A1 (de) * | 1979-08-28 | 1981-03-11 | Ciba-Geigy Ag | Polyazathiaverbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend solche Verbindungen und Verwendung von letzteren |
| US4409214A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
| GR75644B (cg-RX-API-DMAC7.html) * | 1980-06-18 | 1984-08-02 | Fujisawa Pharmaceutical Co | |
| GR78245B (cg-RX-API-DMAC7.html) * | 1980-09-12 | 1984-09-26 | Ciba Geigy Ag | |
| US4521413A (en) * | 1981-09-14 | 1985-06-04 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4486586A (en) * | 1983-02-10 | 1984-12-04 | Bristol-Myers Company | Cephalosporin derivatives |
-
1985
- 1985-02-14 CA CA000474260A patent/CA1276929C/en not_active Expired - Lifetime
- 1985-03-25 ZA ZA852236A patent/ZA852236B/xx unknown
- 1985-04-02 NZ NZ211659A patent/NZ211659A/xx unknown
- 1985-04-02 AR AR85299945A patent/AR244694A1/es active
- 1985-04-03 DD DD85287524A patent/DD249024A5/de unknown
- 1985-04-03 DD DD85274832A patent/DD236735A5/de unknown
- 1985-04-03 DK DK155985A patent/DK155985A/da not_active Application Discontinuation
- 1985-04-03 SE SE8501680A patent/SE466205B/sv not_active IP Right Cessation
- 1985-04-03 DE DE19853512225 patent/DE3512225A1/de active Granted
- 1985-04-04 GB GB08508846A patent/GB2157293B/en not_active Expired
- 1985-04-04 AU AU40862/85A patent/AU580990B2/en not_active Expired
- 1985-04-04 OA OA58561A patent/OA07985A/xx unknown
- 1985-04-04 FI FI851379A patent/FI84830C/fi not_active IP Right Cessation
- 1985-04-04 PT PT80246A patent/PT80246B/pt unknown
- 1985-04-04 IE IE86685A patent/IE58408B1/en not_active IP Right Cessation
- 1985-04-04 CH CH1498/85A patent/CH669197A5/de not_active IP Right Cessation
- 1985-04-04 NL NL8501002A patent/NL192925C/nl not_active IP Right Cessation
- 1985-04-05 AT AT0103985A patent/AT388735B/de not_active IP Right Cessation
- 1985-04-05 LU LU85840A patent/LU85840A1/fr unknown
- 1985-04-05 IL IL74826A patent/IL74826A/xx not_active IP Right Cessation
- 1985-04-05 IT IT20267/85A patent/IT1190353B/it active
- 1985-04-05 FR FR8505281A patent/FR2563832B1/fr not_active Expired
- 1985-04-08 ES ES542013A patent/ES8607318A1/es not_active Expired
- 1985-04-08 RU SU853878102A patent/RU2056425C1/ru active
- 1985-04-08 GR GR850883A patent/GR850883B/el not_active IP Right Cessation
- 1985-04-09 HU HU87151A patent/HU204277B/hu unknown
- 1985-04-09 HU HU851299A patent/HU193750B/hu unknown
- 1985-04-09 YU YU60085A patent/YU46151B/sh unknown
- 1985-04-09 KR KR1019850002383A patent/KR870002166B1/ko not_active Expired
- 1985-04-09 BE BE0/214810A patent/BE902148A/fr not_active IP Right Cessation
- 1985-04-09 JP JP60075233A patent/JPS615084A/ja active Granted
- 1985-11-12 JP JP60252138A patent/JPS61143390A/ja active Granted
- 1985-11-12 JP JP60252139A patent/JPS61143391A/ja active Granted
- 1985-11-12 JP JP60252140A patent/JPS61143387A/ja active Granted
-
1986
- 1986-01-31 ES ES551550A patent/ES8706155A1/es not_active Expired
- 1986-01-31 ES ES551551A patent/ES8706694A1/es not_active Expired
- 1986-02-06 SU SU864018257A patent/SU1375140A3/ru active
- 1986-02-06 SU SU864023036A patent/SU1367858A3/ru active
- 1986-02-06 SU SU864019975A patent/SU1487814A3/ru active
- 1986-02-06 SU SU864020682A patent/SU1436882A3/ru active
- 1986-03-03 DD DD86287525A patent/DD251752A5/de unknown
- 1986-09-10 ES ES557060A patent/ES8800949A1/es not_active Expired
-
1987
- 1987-06-25 YU YU118987A patent/YU46213B/sh unknown
- 1987-09-10 GB GB08721347A patent/GB2194790B/en not_active Expired
- 1987-09-10 GB GB08721346A patent/GB2194789B/en not_active Expired
- 1987-10-01 MY MYPI87002761A patent/MY101940A/en unknown
-
1988
- 1988-11-11 AU AU25041/88A patent/AU610278B2/en not_active Expired
-
1989
- 1989-04-04 IE IE121089A patent/IE58403B1/en not_active IP Right Cessation
- 1989-04-06 SE SE8901224A patent/SE470259B/sv not_active IP Right Cessation
- 1989-04-06 SE SE8901225A patent/SE505256C2/sv not_active IP Right Cessation
- 1989-04-06 SE SE8901226A patent/SE470260B/sv not_active IP Right Cessation
-
1991
- 1991-08-12 CA CA000616143A patent/CA1340638C/en not_active Expired - Fee Related
- 1991-08-21 CA CA000616144A patent/CA1340672C/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Патент US № 4332800, кл. 424-246, опублик. 1982. Патент US № 4390534, кл. 424-246, опублик. 1983. * |
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