DK156272B - Fremgangsmaade til fremstilling af 7-d-(-)-alpha-amino-alpha-(p-hydroxyphenylacetamido)desacetoxycephalosporansyre - Google Patents
Fremgangsmaade til fremstilling af 7-d-(-)-alpha-amino-alpha-(p-hydroxyphenylacetamido)desacetoxycephalosporansyre Download PDFInfo
- Publication number
- DK156272B DK156272B DK559588A DK559588A DK156272B DK 156272 B DK156272 B DK 156272B DK 559588 A DK559588 A DK 559588A DK 559588 A DK559588 A DK 559588A DK 156272 B DK156272 B DK 156272B
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- Prior art keywords
- amino
- esterase
- acid
- product
- hydrate
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- 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
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
- C12P37/00—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Description
DK 156272 B
Den foreliggende opfindelse angâr en særlig fremgangsmâde til enzymatisk fremstilling af den kendte forbindelse 7-D-(-)-a-amino-a-(p-hydroxyphenylacetamido)desacetoxycephalosporansyrer.
Skdnt 7-D-(-)-a-amino-α-(p-acetoxyphenylacetamido)desacetoxycepha-5 losporansyre er stabil i normal saltoplpsning, har det vist sig, at den hydrolyseres enzymatisk til den kendte og virkningsfulde 7-D-(-)-a-amino-a-(p-hydroxyphenylacetamidojdesacetoxycephalosporansyre.
Ifplge den foreliggende opfindelse tilvejebringes sâledes en særlig fremgangsmâde til fremstilling af 7-D-(-)-a-amino-a-(p-hydro-10 xyphenylacetamidoJdesacetoxycephalosporansyre, et hydrat eller et farma-ceutisk acceptabelt sait deraf, hvilken fremgangsmâde er ejendommelig ved, at man i vandig oplpsning behandler 7-D-(-)-a-amino-oi-(p-acetoxyphenyl acetamido)desacetoxycephalosporansyre med en esterase ved en pH-værdi mellem ca. 5,0 og ca. 7,5, isolerer produktet pâ i og for sig 15 kendt màde og om pnsket pâ i og for sig kendt mâde omdanner produktet, der forefindes som den fri syre eller et hydrat deraf, til det tilsva-rende, farmaceutisk acceptable sait deraf.
En foretrukken udfprelsesform af fremgangsmâden if0lge opfindelsen er ejendommelig ved, at man fremstiller 7-D-(-)-a-amino-a-(p-hydroxyphe-20 nylacetamido)desacetoxycephalosporansyre, et hydrat eller et farmaceutisk acceptabelt sait deraf ved i vandig oplpsning at behandle 7-D-(-)-a-ami no-α-(p-acetoxyphenylacetamido)desacetoxycephalosporansyre med en esterase, som stammer fra human-serum, animalsk sérum, citrusesterase, hvedeklid, hvedekim eller bacillus subtilis ved en pH-værdi mellem ca.
25 5,0 og ca. 7,5 og ved en koncentration pâ ca. 5 til ca. 10 mg/ml esterase, baseret pâ det totale volumen vandig oplpsning, isolere produktet pâ i og for sig kendt màde og om pnsket omdanne produktet, der forefindes som den fri syre eller et hydrat deraf, til det tilsvarende farmaceutisk acceptable sait deraf.
30 En kommercielt foretrukken udfprelsesform af fremgangsmâden ifdlge den foreliggende opfindelse er ejendommelig ved, at man fremstiller 7-D-(-)-a-amino-a-(p-hydroxyphenylacetamido)desacetoxycephalosporansyre, et hydrat eller et farmaceutisk acceptabelt sait deraf ved i vandig oplds-ning at behandle en 7-D-(-)-a-amino-a-(p-acetoxyphenylacetamido)cepha-35 losporansyre med en esterase valgt blandt citrusesterase, hvedeklid eller hvedekim ved en pH-værdi mellem ca. 5,0 og ca. 7,5 og ved en koncentration pâ ca. 5 til ca. 10 mg/ml esterase, baseret pâ det totale volumen vandig oplosning, isolere produktet pâ i og for sig kendt mâde og
DK 156272B
2 om 0nsket omdanne produktet, der forefindes som den fri syre eller et hydrat deraf, ti1 det tilsvarende farmaceutisk acceptable sait deraf.
Af særlig kommerciel interesse er en fremgangsmâde tîl fremstil-1ing af 7-D-(-)-a-amino-a-(p-hydroxyphenylacetamido)desacetoxycephalo-5 sporansyre, et hydrat eller et farmaceutisk acceptabelt sait deraf, hvilken fremgangsmâde er ejendommelig ved, at man i vandig oplpsning be-handler 7-D-(-)-a-amino-a-(p-acetoxyphenylacetamido)desacetoxycephalo-sporansyre med den kommercielt tilgængelige esterase, groft hvedeklid, ved en pH-værdi mellem 5,5 og 6,0 eller eventuelt i nærvær af en puffer 10 ved en pH-værdi pâ 7,0 ved en koncentration pâ ca. 10 mg/ml esterase, baseret pâ det totale volumen oplesning, isolerer produktet pâ i og for sig kendt mâde og om pnsket omdanner produktet, der forefindes som den fri syre eller et hydrat deraf, ti1 det tilsvarende farmaceutisk acceptable sait deraf.
15 7-D-(-)-a-amino-a-(p-hydroxyphenylacetamido)desacetoxycephalospo- ransyren, fremstillet i overensstemmelse med fremgangsmâden ifolge den foreliggende opfindelse, er kendt som et effektivt antibakterielt mid-del, som er nyttigt tîl behandling af fjerkræ, dyr og mennesker for in-fektionssygdomme, forârsaget af mange Gram-positive og Gram-negative 20 bakterier.
I fdlgende eksempel belyses fremgangsmâden ifplge opfindelsen.
Eksempel
Oplpsninger med 0,5 mg/ml 7-D-(-)-a-amino-a-(p-acetoxyphenylacet-25 amido)desacetoxycephalosporansyre (p-acetoxycephalexin) i normal saltop-ldsning og i human-serum fremstilledes. Standardoplpsninger med 0,5 mg/ml 7-D-(=)-a-ami no-a-(p-hydroxyphenylacetamido)desacetoxycephalospo-ransyre (p-hydroxycephalexin) fremstilledes ogsâ i bâde normal saltop-lpsning og manneske-sérum.
30 Aile de ovennævnte oplpsninger inkuberedes ved 37°C under omryst- ning, og pr0ver til kromatografi blev udtaget efter 0, 2, 4, 8 og 24 ti-mer. Ca. 5 mikroliter af hver prpve sattes pâ hver sin 13 mm brede strimmel Whatman nr. 1 papir, som tprredes og fremkaldtes i en blanding bestâende af 30 dele butylacetat, 15 dele n-butanol, 40 dele eddikesyre 35 og 24 dele vand. Strimlerne blev sâ bioautograferet pâ plader, podet med bacillus subtilis ved en pH-værdi pâ 6,0.
Biokromatogrammerne viste, at p-acetoxycephalexin hurtigt hydroly-seredes til p-hydroxy-formen i human-serum, man var stabil i normal 3
DK 156272B
saltopl0sning.
Claims (3)
1. Fremgangsmâde til fremstilling af 7-D-(-)-a-amino-a-(p-hydro-xypheny1acetamido)desacetoxycephalosporansyre, et hydrat eller et farma- 5 ceutisk acceptabelt sait deraf, KENDETEGNET ved, AT man i vandig oplps-ning behandler 7-D-(-)-û;-amino-a-{p-acetoxyphenylacetamido)desacetoxy-cephalosporansyre med en esterase ved en pH-værdi pà mellem ca. 5,0 og ca. 7,5, isolerer produktet pâ i og for sig kendt mâde, og om pnsket pâ i og for sig kendt mâde omdanner produktet, der forefindes som den fri 10 syre eller et hydrat deraf, til et tilsvarende farmaceutisk acceptabelt sait deraf.
2. Fremgangsmâde if0lge krav 1, KENDETEGNET ved, AT man i vandig oplpsning behandler 7-D-(-)-ar-amino-a-(p-acetoxyphenylacetamido)desace- 15 toxycephalosporansyre med en esterase, som stammer fra human-serum, ani-malsk sérum, citrusesterase, hvedeklid, hvedekim eller bacillus subtilis ved en pH-værdi mellem ca. 5,0 og ca. 7,5 og ved en koncentration pà ca. 5 til ca. 10 mg/ml esterase, baseret pâ det totale volumen vandig oplpsning, isolerer produktet pà i og for sig kendt mâde og om pnsket omdan-20 ner produktet, der forefindes som den fri syre eller et hydrat deraf, til et tilsvarende farmaceutisk acceptabelt sait deraf.
3. Fremgangsmâde ifpige krav 1 eller 2, KENDETEGNET ved, AT man i vandig oplpsning behandler 7-D-(-)-a-amino-a-(p-acetoxyphenylacetamido)- 25 desacetoxycephalosporansyre med den kommercielt tilgængelige esterase, groft hvedeklid, ved en pH-værdi pâ mellem 5,5 og 6,0 eller eventuelt i nærvaer af en puffer ved en pH-værdi pà 7,0 ved en koncentration pà ca. 10 mg/ml esterase, baseret pà det totale volumen oplpsning, isolerer produktet pâ i og for sig kendt mâde og om pnsket omdanner produktet, 30 der forefindes som den fri syre eller et hydrat deraf, til et tilsvarende farmaceutisk acceptabelt sait deraf. 35
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2484874 | 1974-06-05 | ||
| GB2484874A GB1476981A (en) | 1974-06-05 | 1974-06-05 | Substituted penicillanic acids |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK559588D0 DK559588D0 (da) | 1988-10-06 |
| DK559588A DK559588A (da) | 1988-10-06 |
| DK156272B true DK156272B (da) | 1989-07-24 |
| DK156272C DK156272C (da) | 1989-12-18 |
Family
ID=10218206
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK236275A DK155943C (da) | 1974-06-05 | 1975-05-28 | Analogifremgangsmaade til fremstilling af 7-d-(-)-alfa-amino-alfa-(p-acetoxyphenyl)acetamidocephalosporansyrer |
| DK559588A DK156272C (da) | 1974-06-05 | 1988-10-06 | Fremgangsmaade til fremstilling af 7-d-(-)-alpha-amino-alpha-(p-hydroxyphenylacetamido)desacetoxycephalosporansyre |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK236275A DK155943C (da) | 1974-06-05 | 1975-05-28 | Analogifremgangsmaade til fremstilling af 7-d-(-)-alfa-amino-alfa-(p-acetoxyphenyl)acetamidocephalosporansyrer |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4012382A (da) |
| JP (4) | JPS6150955B2 (da) |
| AR (2) | AR210855A1 (da) |
| AT (1) | AT339480B (da) |
| AU (1) | AU496892B2 (da) |
| BE (2) | BE828686A (da) |
| CA (1) | CA1051799A (da) |
| CH (1) | CH617202A5 (da) |
| CS (1) | CS189709B2 (da) |
| DD (3) | DD127730A5 (da) |
| DE (1) | DE2524320C2 (da) |
| DK (2) | DK155943C (da) |
| ES (2) | ES438179A1 (da) |
| FI (1) | FI60867C (da) |
| FR (2) | FR2273546A1 (da) |
| GB (1) | GB1476981A (da) |
| HU (3) | HU174102B (da) |
| IE (1) | IE43052B1 (da) |
| IL (2) | IL47360A (da) |
| IN (1) | IN142267B (da) |
| LU (1) | LU72618A1 (da) |
| SE (2) | SE426171B (da) |
| SU (3) | SU828968A3 (da) |
| YU (3) | YU40121B (da) |
| ZA (2) | ZA752504B (da) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3989694A (en) * | 1974-12-27 | 1976-11-02 | Smithkline Corporation | 7-Acyl-3-(substituted triazolyl thiomethyl)cephalosporins |
| US4286089A (en) * | 1974-12-27 | 1981-08-25 | Smithkline Corporation | 7-Acyl-3-(substituted tetrazolyl thiomethyl)cephalosporins |
| OA05233A (fr) * | 1975-02-04 | 1981-02-28 | Fujisawa Pharmaceutical Co | Procédé de préparation d'acides (7-acétamido Disubstitue)-3- substitue-3- cephem-4-carboxyliques et nouveaux produits industriels. |
| US4093723A (en) * | 1976-05-19 | 1978-06-06 | Smithkline Corporation | 7-Acyl-3-(sulfonic acid and sulfamoyl substituted tetrazolyl thiomethyl) cephalosporins |
| US4107440A (en) * | 1975-12-15 | 1978-08-15 | Smithkline Corporation | Intermediates for preparing substituted phenylglycylcephalosporins |
| IL51651A0 (en) * | 1976-03-19 | 1977-05-31 | Merck Patent Gmbh | Cephem derivatives and processes for their preparation |
| GB1532682A (en) * | 1976-04-27 | 1978-11-22 | Bristol Myers Co | Process for the preparation of cephadroxil |
| US4034092A (en) * | 1976-05-03 | 1977-07-05 | Smithkline Corporation | 7-Acyl-3-(carboxyalkyl and carbamoylalkyl substituted oxadiazolylthiomethyl) cephalosporins |
| AU2550077A (en) * | 1976-06-14 | 1978-11-30 | Merck Patent Gmbh | Penicillins and cephalosporins |
| JPS5346995A (en) * | 1976-10-12 | 1978-04-27 | Sangyo Kagaku Kenkyu Kyokai | Antibacterial agents |
| US4160863A (en) | 1977-04-07 | 1979-07-10 | Bristol-Myers Company | Process for the preparation of the crystalline monohydrate of 7-[D-α-aα-(p-hydroxyphenyl)acetamido]-3-methyl-3-cephem-4-carboxylic acid |
| US4236002A (en) * | 1977-12-23 | 1980-11-25 | Yeda Research & Development Co., Ltd. | Cephalosporin derivatives |
| DE2852067A1 (de) * | 1978-11-29 | 1980-06-12 | Schering Ag | Verfahren zur herstellung von 5-mercapto-1,2,3-triazolen |
| DE2920939A1 (de) * | 1979-05-21 | 1980-11-27 | Schering Ag | Verfahren zur herstellung von 5-mercapto-1,2,3-triazolen |
| JPS58122471U (ja) * | 1982-02-15 | 1983-08-20 | 株式会社ほくさん | クライオスタツトのスペ−サ− |
| JPS59152757U (ja) * | 1983-03-31 | 1984-10-13 | 株式会社ほくさん | クライオスタツトのスペ−サ |
| JPS6019776A (ja) * | 1983-07-12 | 1985-01-31 | Ube Ind Ltd | 安定化された５―メルカプト―１，２，３―チアジアゾール類組成物 |
| JPS6041271A (ja) * | 1984-07-09 | 1985-03-04 | Hitachi Ltd | 超電導装置 |
| GB9216759D0 (en) * | 1992-08-07 | 1992-09-23 | Finpael Spa | Process for the production of 7-amino thiazolyl cephalosporins |
| US6550343B2 (en) * | 2001-07-13 | 2003-04-22 | Westinghouse Air Brake Technologies Corporation | Method and apparatus for testing shear strength of rubber bonded to metal insert |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1461320A (fr) | 1961-04-10 | 1966-02-25 | Nat Res Dev | Procédé de production de dérivés de désacétylation de la céphalosporine c |
| GB1082943A (en) * | 1963-03-27 | 1967-09-13 | Glaxo Lab Ltd | Derivatives of 7-aminocephalosporanic acid |
| GB1082962A (en) * | 1963-05-28 | 1967-09-13 | Glaxo Lab Ltd | Derivatives of 7-aminocephalosporanic acid |
| DE1445639B2 (de) | 1963-11-19 | 1976-09-09 | Ciba-Geigy Ag, Basel (Schweiz) | Verfahren zur herstellung von desacetyl-7-aminocephalosporansaeure |
| FR1460131A (fr) * | 1964-10-30 | 1966-06-17 | Glaxo Lab Ltd | Procédé de préparation de produits de dégradation de la céphalosporine c et de ses dérivés |
| US3453263A (en) * | 1965-03-01 | 1969-07-01 | American Home Prod | Method of preparing penicillins |
| GB1241656A (en) * | 1967-08-21 | 1971-08-04 | Glaxo Lab Ltd | Improvements in or relating to cephalosporin compounds |
| US3489750A (en) * | 1967-09-05 | 1970-01-13 | Bristol Myers Co | 7-amino-cephalosporanic and decephalosporanic acid derivatives |
| GB1277415A (en) * | 1968-06-14 | 1972-06-14 | Glaxo Lab Ltd | Improvements in or relating to cephalosporin derivatives |
| US3579514A (en) * | 1969-01-24 | 1971-05-18 | Bristol Myers Co | 7 - (alpha-(3 - guanyl-1-ureido)aryl-acetamido) cephalosporanic acids and derivatives thereof |
| US3641021A (en) * | 1969-04-18 | 1972-02-08 | Lilly Co Eli | 3 7-(ring-substituted) cephalosporin compounds |
| GB1326531A (en) * | 1969-08-26 | 1973-08-15 | Glaxo Lab Ltd | Cephalosporin compounds |
| US3753977A (en) * | 1969-11-27 | 1973-08-21 | Ciba Geigy Corp | Process for the cleavage of esters of 7-amino-cephem-4-carboxylic acid compounds |
| GB1342241A (en) * | 1970-01-23 | 1974-01-03 | Glaxo Lab Ltd | Cephalosporin compounds |
| GB1334382A (en) * | 1970-03-26 | 1973-10-17 | Glaxo Lab Ltd | Antibiotics |
| US3701775A (en) * | 1970-11-25 | 1972-10-31 | Smith Kline French Lab | Esters of mandeloylaminocephalosporanic acids |
| US3855213A (en) * | 1971-02-18 | 1974-12-17 | Smith Kline French Lab | 3-heterocyclic thiomethyl-cephalosporins |
| IL38099A (en) * | 1970-12-17 | 1976-01-30 | Smith Kline French Lab | 3-heterocyclyl thiomethylcephalosporins |
| US3867380A (en) * | 1971-02-18 | 1975-02-18 | Smithkline Corp | 3-Heterocyclic thiomethylcephalosporins |
| GB1319173A (en) * | 1971-06-17 | 1973-06-06 | Fujisawa Pharmaceutical Co | 7-acylated-3-substituted cephalosporin compounds |
| JPS5442997B2 (da) * | 1971-10-18 | 1979-12-17 | ||
| JPS4868588A (da) * | 1971-12-22 | 1973-09-18 | ||
| US3813388A (en) * | 1972-01-31 | 1974-05-28 | L Crast | 7-(d-(alpha-amino-alpha-phenyl-,2-thienyl-and 3-thienyl-acetamido))-3-(s-(2-methyl-1,2,3-triazole-4-yl)thiomethyl)-3-cephem-4-carboxylic acids |
| CA1076560A (en) * | 1972-06-14 | 1980-04-29 | Smith Kline And French Canada Ltd. | 3-heterocyclic thiomethylcephalosporins |
| US3868369A (en) * | 1972-11-14 | 1975-02-25 | Smithkline Corp | 3-heterocyclicthiomethylcephalosporins |
| US3943129A (en) * | 1972-11-14 | 1976-03-09 | Smithkline Corporation | 7-Amino-3-(1,3,4-thiadiazolinylthio-methyl) cephalosporins |
| US3953439A (en) * | 1973-08-01 | 1976-04-27 | Smithkline Corporation | Substituted phenylglycylcephalosporins |
| US3931160A (en) * | 1974-05-15 | 1976-01-06 | Smithkline Corporation | α-Amino-α-(acylamidophenyl)acetamidocephalosporins |
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1974
- 1974-06-05 GB GB2484874A patent/GB1476981A/en not_active Expired
-
1975
- 1975-04-18 ZA ZA00752504A patent/ZA752504B/xx unknown
- 1975-05-02 BE BE156029A patent/BE828686A/xx not_active IP Right Cessation
- 1975-05-14 HU HU75BI515A patent/HU174102B/hu unknown
- 1975-05-24 IN IN1053/CAL/75A patent/IN142267B/en unknown
- 1975-05-26 IL IL47360A patent/IL47360A/xx unknown
- 1975-05-26 ZA ZA00753387A patent/ZA753387B/xx unknown
- 1975-05-26 AU AU81529/75A patent/AU496892B2/en not_active Expired
- 1975-05-27 US US05/581,054 patent/US4012382A/en not_active Expired - Lifetime
- 1975-05-28 DK DK236275A patent/DK155943C/da not_active IP Right Cessation
- 1975-05-30 LU LU72618A patent/LU72618A1/xx unknown
- 1975-05-30 FI FI751595A patent/FI60867C/fi not_active IP Right Cessation
- 1975-05-30 BE BE156933A patent/BE829758A/xx not_active IP Right Cessation
- 1975-06-02 DE DE2524320A patent/DE2524320C2/de not_active Expired
- 1975-06-02 HU HU75BI536A patent/HU173040B/hu unknown
- 1975-06-02 SE SE7506294A patent/SE426171B/xx not_active IP Right Cessation
- 1975-06-02 HU HU75BI00000516A patent/HU172448B/hu unknown
- 1975-06-02 CA CA228,229A patent/CA1051799A/en not_active Expired
- 1975-06-03 DD DD7500195744A patent/DD127730A5/xx unknown
- 1975-06-03 ES ES438179A patent/ES438179A1/es not_active Expired
- 1975-06-03 DD DD7500195747A patent/DD127731A5/xx unknown
- 1975-06-03 DD DD186424A patent/DD122094A5/xx unknown
- 1975-06-04 SU SU752143253A patent/SU828968A3/ru active
- 1975-06-04 IE IE1245/75A patent/IE43052B1/en unknown
- 1975-06-04 CS CS753917A patent/CS189709B2/cs unknown
- 1975-06-04 FR FR7517489A patent/FR2273546A1/fr not_active Withdrawn
- 1975-06-04 YU YU1437/75A patent/YU40121B/xx unknown
- 1975-06-05 AT AT429375A patent/AT339480B/de active
- 1975-06-05 CH CH727975A patent/CH617202A5/de not_active IP Right Cessation
- 1975-06-05 JP JP50067119A patent/JPS6150955B2/ja not_active Expired
- 1975-06-08 AR AR259056A patent/AR210855A1/es active
- 1975-11-18 SU SU752189817A patent/SU629880A3/ru active
- 1975-11-18 SU SU752189951A patent/SU654171A3/ru active
-
1976
- 1976-01-01 AR AR262382A patent/AR208111A1/es active
- 1976-01-20 FR FR7601467A patent/FR2296639A1/fr active Granted
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1977
- 1977-01-12 ES ES454964A patent/ES454964A1/es not_active Expired
- 1977-11-16 IL IL53407A patent/IL53407A0/xx not_active IP Right Cessation
-
1978
- 1978-04-05 SE SE7803860A patent/SE434840B/sv not_active IP Right Cessation
-
1981
- 1981-08-18 YU YU1997/81A patent/YU45103B/xx unknown
- 1981-08-18 YU YU1998/81A patent/YU43130B/xx unknown
-
1984
- 1984-12-21 JP JP59268756A patent/JPS60166688A/ja active Granted
-
1985
- 1985-04-19 JP JP60082717A patent/JPS60259198A/ja active Granted
- 1985-04-19 JP JP60082716A patent/JPS60260585A/ja active Pending
-
1988
- 1988-10-06 DK DK559588A patent/DK156272C/da not_active IP Right Cessation
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| Date | Code | Title | Description |
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| PUP | Patent expired |