CS221801B2 - Method of praparation of the derivative of 4-deoxy-4-aminoerythromycine a - Google Patents
Method of praparation of the derivative of 4-deoxy-4-aminoerythromycine a Download PDFInfo
- Publication number
- CS221801B2 CS221801B2 CS78703A CS70378A CS221801B2 CS 221801 B2 CS221801 B2 CS 221801B2 CS 78703 A CS78703 A CS 78703A CS 70378 A CS70378 A CS 70378A CS 221801 B2 CS221801 B2 CS 221801B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen
- product
- acid
- solution
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 230000002829 reductive effect Effects 0.000 claims description 11
- 150000003863 ammonium salts Chemical class 0.000 claims description 9
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 8
- 239000005695 Ammonium acetate Substances 0.000 claims description 8
- 229940043376 ammonium acetate Drugs 0.000 claims description 8
- 235000019257 ammonium acetate Nutrition 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 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 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- 150000004678 hydrides Chemical group 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical group [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- 229960003276 erythromycin Drugs 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- 229940126601 medicinal product Drugs 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
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- 239000000047 product Substances 0.000 description 58
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- 239000000243 solution Substances 0.000 description 51
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
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- 239000000203 mixture Substances 0.000 description 35
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
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- 239000007787 solid Substances 0.000 description 14
- 229960004132 diethyl ether Drugs 0.000 description 13
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 239000000376 reactant Substances 0.000 description 11
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
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- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 239000013505 freshwater Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- -1 Sulfonamide derivatives of erythromycylamine Chemical class 0.000 description 5
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- 239000007858 starting material Substances 0.000 description 4
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- RJUOFRHFMOGWOG-UHFFFAOYSA-N 4-(chloroamino)-4-oxobutanoic acid Chemical compound OC(=O)CCC(O)=NCl RJUOFRHFMOGWOG-UHFFFAOYSA-N 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229930006677 Erythromycin A Natural products 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 150000002118 epoxides Chemical class 0.000 description 1
- YVTFLQUPRIIRFE-QUMKBVJLSA-N erythronolide A Chemical compound CC[C@H]1OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O YVTFLQUPRIIRFE-QUMKBVJLSA-N 0.000 description 1
- ZFBRGCCVTUPRFQ-HWRKYNCUSA-N erythronolide B Chemical compound CC[C@H]1OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C ZFBRGCCVTUPRFQ-HWRKYNCUSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76548077A | 1977-02-04 | 1977-02-04 | |
| US05/856,479 US4150220A (en) | 1977-02-04 | 1977-12-01 | Semi-synthetic 4"-erythromycin A derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS221801B2 true CS221801B2 (en) | 1983-04-29 |
Family
ID=27117613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS78703A CS221801B2 (en) | 1977-02-04 | 1978-02-02 | Method of praparation of the derivative of 4-deoxy-4-aminoerythromycine a |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS5827798B2 (it) |
| AR (1) | AR222147A1 (it) |
| AU (1) | AU501298B1 (it) |
| BG (2) | BG33159A3 (it) |
| CA (1) | CA1106367A (it) |
| CH (1) | CH628906A5 (it) |
| CS (1) | CS221801B2 (it) |
| DD (1) | DD140048A5 (it) |
| DE (1) | DE2804507C2 (it) |
| DK (1) | DK148036C (it) |
| ES (2) | ES466057A1 (it) |
| FI (1) | FI780354A7 (it) |
| FR (2) | FR2379550A1 (it) |
| GB (2) | GB1585315A (it) |
| GR (1) | GR68691B (it) |
| HU (1) | HU182559B (it) |
| IE (1) | IE46661B1 (it) |
| IL (2) | IL53968A0 (it) |
| IT (1) | IT1094209B (it) |
| LU (1) | LU79004A1 (it) |
| NL (1) | NL176174C (it) |
| NO (2) | NO146472C (it) |
| NZ (1) | NZ186385A (it) |
| PH (2) | PH14421A (it) |
| PL (1) | PL116228B1 (it) |
| PT (1) | PT67568B (it) |
| RO (4) | RO77345A (it) |
| SE (2) | SE445223B (it) |
| SU (1) | SU927122A3 (it) |
| YU (3) | YU40913B (it) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4133950A (en) * | 1978-01-03 | 1979-01-09 | Pfizer Inc. | 4"-Deoxy-4"-carbamate and dithiocarbamate derivatives of oleandomycin and its esters |
| US4124755A (en) * | 1978-01-03 | 1978-11-07 | Pfizer Inc. | 11-Alkanoyl-4"-deoxy-4"-isonitrilo-oleandomycin derivatives |
| US4382085A (en) * | 1982-03-01 | 1983-05-03 | Pfizer Inc. | 4"-Epi erythromycin A and derivatives thereof as useful antibacterial agents |
| US4518590A (en) * | 1984-04-13 | 1985-05-21 | Pfizer Inc. | 9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method |
| HN1998000074A (es) * | 1997-06-11 | 1999-01-08 | Pfizer Prod Inc | Derivados de macrolidos c-4 sustituidos |
| US6407074B1 (en) | 1997-06-11 | 2002-06-18 | Pfizer Inc | C-4″-substituted macrolide derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3836519A (en) * | 1973-05-04 | 1974-09-17 | Abbott Lab | Sulfonyl derivatives of erythromycin |
| US3884903A (en) * | 1973-06-21 | 1975-05-20 | Abbott Lab | 4{41 -Deoxy-4{41 -oxoerythromycin B derivatives |
-
1978
- 1978-01-10 SE SE7800270A patent/SE445223B/sv not_active IP Right Cessation
- 1978-01-13 PH PH20662A patent/PH14421A/en unknown
- 1978-01-17 ES ES466057A patent/ES466057A1/es not_active Expired
- 1978-01-18 YU YU73/78A patent/YU40913B/xx unknown
- 1978-01-18 AR AR270752A patent/AR222147A1/es active
- 1978-01-23 PT PT67568A patent/PT67568B/pt unknown
- 1978-01-31 CH CH106178A patent/CH628906A5/fr not_active IP Right Cessation
- 1978-02-02 DE DE2804507A patent/DE2804507C2/de not_active Expired
- 1978-02-02 CS CS78703A patent/CS221801B2/cs unknown
- 1978-02-02 GR GR55330A patent/GR68691B/el unknown
- 1978-02-02 CA CA296,037A patent/CA1106367A/en not_active Expired
- 1978-02-02 RO RO7893080A patent/RO77345A/ro unknown
- 1978-02-02 RO RO78101651A patent/RO79687A7/ro unknown
- 1978-02-02 GB GB4165/78A patent/GB1585315A/en not_active Expired
- 1978-02-02 RO RO105255A patent/RO81622B/ro unknown
- 1978-02-02 RO RO78101650A patent/RO79686A7/ro unknown
- 1978-02-02 GB GB34309/79A patent/GB1585316A/en not_active Expired
- 1978-02-03 JP JP53011352A patent/JPS5827798B2/ja not_active Expired
- 1978-02-03 IT IT20005/78A patent/IT1094209B/it active
- 1978-02-03 LU LU79004A patent/LU79004A1/xx unknown
- 1978-02-03 IE IE239/78A patent/IE46661B1/en not_active IP Right Cessation
- 1978-02-03 DK DK51878A patent/DK148036C/da not_active IP Right Cessation
- 1978-02-03 IL IL53968A patent/IL53968A0/xx not_active IP Right Cessation
- 1978-02-03 SU SU782573754A patent/SU927122A3/ru active
- 1978-02-03 FR FR7803066A patent/FR2379550A1/fr active Granted
- 1978-02-03 BG BG040069A patent/BG33159A3/xx unknown
- 1978-02-03 NZ NZ186385A patent/NZ186385A/xx unknown
- 1978-02-03 FI FI780354A patent/FI780354A7/fi not_active Application Discontinuation
- 1978-02-03 NO NO780389A patent/NO146472C/no unknown
- 1978-02-03 HU HU78PI611A patent/HU182559B/hu not_active IP Right Cessation
- 1978-02-03 DD DD78203547A patent/DD140048A5/de unknown
- 1978-02-03 PL PL1978204428A patent/PL116228B1/pl unknown
- 1978-02-03 BG BG038579A patent/BG32718A3/xx unknown
- 1978-02-03 NL NLAANVRAGE7801262,A patent/NL176174C/xx not_active IP Right Cessation
- 1978-02-03 AU AU32990/78A patent/AU501298B1/en not_active Expired
- 1978-07-07 FR FR7820334A patent/FR2385735A1/fr active Granted
- 1978-08-08 ES ES472429A patent/ES472429A1/es not_active Expired
- 1978-09-01 PH PH21555A patent/PH16675A/en unknown
-
1981
- 1981-01-27 IL IL61997A patent/IL61997A0/xx unknown
- 1981-06-05 NO NO811913A patent/NO150484C/no unknown
-
1983
- 1983-02-07 YU YU265/83A patent/YU40798B/xx unknown
- 1983-02-16 SE SE8300870A patent/SE457086B/xx not_active IP Right Cessation
- 1983-11-21 YU YU2279/83A patent/YU40799B/xx unknown
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