NO138142B - Analogifremgangsmaate for fremstilling av terapeutisk aktive 6(alfa-aminobenzyl-alfa-penicilloyl-amino)-kapronsyre og salter derav - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive 6(alfa-aminobenzyl-alfa-penicilloyl-amino)-kapronsyre og salter derav Download PDFInfo
- Publication number
- NO138142B NO138142B NO790/72A NO79072A NO138142B NO 138142 B NO138142 B NO 138142B NO 790/72 A NO790/72 A NO 790/72A NO 79072 A NO79072 A NO 79072A NO 138142 B NO138142 B NO 138142B
- Authority
- NO
- Norway
- Prior art keywords
- alfa
- penicilloyl
- salts
- aminobenzyl
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 3
- 229960002684 aminocaproic acid Drugs 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- 229960000723 ampicillin Drugs 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 125000000926 ampicilloyl group Chemical group [H]N([H])[C@@]([H])(C(=O)N([H])[C@]1([H])C(=O)N2[C@]1([H])SC(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])C(*)=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OPEGYZAATHKDEM-HCWXCVPCSA-N (2r,4s)-2-[(r)-carboxy(formamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid Chemical class CC1(C)S[C@H]([C@H](NC=O)C(O)=O)N[C@H]1C(O)=O OPEGYZAATHKDEM-HCWXCVPCSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960003311 ampicillin trihydrate Drugs 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 108010074605 gamma-Globulins Proteins 0.000 description 1
- 230000035931 haemagglutination Effects 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 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 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002568 urticarial effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
Nærværende oppfinnelse vedrører fremstilling av 6- (a-.aminobensyl-a-penicilloylamino)-kapronsyre med formelen
såvel salter derav.
Forbindelsen med formel I kan også foreligge som salter, f.
eks- som Na-, K— eller Ca-salt. Videre kan forbindelsen foreligge som et indre salt, hvorved saltdannelsen skjer mellom aminogruppe og karboksylgruppe.
Forbindelsen med formel I og dens salter kan fremstilles
ved at man omsetter en forbindélse med den generelle formel
med 6-aminokapronsyre og overfører, hvis ønsket, reaksjons-
produktet til et salt.
Omsetningen av forbinelsen med formel II med 6-aminokapron-
syre foretas hensiktsmessig i vandig-alkalisk medium. Reak-
sjonsstemperaturen er fortrinnsvis 5 - 30°C.
Forbindelsen med formelen I og dens -farmasøytisk aksepterbare salter kan anvendes til hemning av allergiske -reaksjoner. som opptrer ved administrasjon-av pencilliner.
Således kunne in vitro utfellingen av anti-pencilloyl-anti-- stoffer, frem for alt anti-ampicilloyl-antistoffer (utvun-net fra kanin- og marsvinsera) hemmes ved pencilloyl-antigen-ner ved hjelp av 6-(a-aminobenzyl-a-penicilloyl-amino)kapronsyre. Videre ble det funnet at forannevnte penicilloinsyre-derivat hemmer hemagglutinasjon av med anti-penicilloyl-antistoffer, frem for alt anti-ampicilloyl-antistoffer, pre-irikuberte erythrozyter ved ampicilloyl-antigener. Likeledes lot den ved ampicilloyl-antigener fremkalte kontraksjon av i det ved anti-ampicilloyl-kanin-y-globulin passivt sensibili-serte marsvin-ileum (Schultz-Dale-forsdk) seg hemme. In vivo kunne ved 6-(a-aminobenzyl-a-penicilloyl-amino)-kapronsyre penicillinallergiske reaksjoner, som f.eks. den passive hud-
: anaphylaxi hos marsvin såvel som den urtikarielle hudreaksjon, i hos ampicillinalergiske mennesker, hemmes. Det analoge gjel-^
der for 6-[a-amino- (1,4-cykloheksadienyl)metyl-a-penicilloyl- : aminoj-kapronsyre.
Den følgende forsøksrapport viser virkningen av fremgangsmåte-produktet sammenliknet med N 6 -(bensyl-a-penicilloyl-N 2-formyl-L-lysin fremstillt ifølge dansk patent nr-, 125 250.
F 0_R_S_0_K_S_R_A_P_P_0 RT
Formål:
For å vurdere den relative aktivitet for 6- (oc-aminobenzyl-a-pehicilloylamino)-kapronsyre, fremstilt ifolge soknad nr. 790/72 i det folgende betegnet som forbindelse A, og for N -
(benzyl-oc-penicilloyl)-N 2-formyl-L-lysin, fremstilt ifolge dansk patent nr. 125.250 og i det folgende betegnet som forbindelse B, for hemning av eksperimentelle allergiske reaksjoner som skyldes ampicillin.
Fr emqanq småt éi
Antilegemer fremstilles i kaniner ved konjugater av ampicillin med okso-gamma-globulin i fullstendig Freund's hjelpemiddel.
Disse antisera injiseres intradermalt i forskjellige fortyn-nelser tfl. grupper på 4 marsvin, som 24 timer senere intravenost mottar 1 mg av konjugatet som er dannet av ampicillin med poly-lysin. Det inhiberende hapten, dvs. forbindelse A eller B, injiseres samtidig med doser på lOO, 20, 10 og 1 mg sammen med
0,5 ml 1%'s Evans blått. De uttredende blå reaksjoner (passive kutane anaphylaktiske reaksjoner) måles 30 minutter senere.
I tabellen nedenfor er disse reaksjoner uttrykt i % av de reaksjoner som oppnåes i dyr som ikke ble behandlet med det inhiberende hapten.
Resultater;
Konklus j oner
Forbindelse Å er langt mere effektiv enn forbindelse B til
å hemme allergistiske reaksjoner som skyldes ampicillin.
Fremgangsmåteprodukte-t: .kan finne anvendelse i form av f arma- ;! soytiske preparater som inneholder dette eller dens salter i i' blanding =med et for den enterale eller parenterale adminxstra-' sjon egnet farmasoytiskj organisk eller uorganisk inert bære-materiale, som f.eks. vann, planteoljer, polyalkylenglykoler o.s.v.. De farmasøytiske preparater kan foreligge f.eks. som opplesninger, suspensjoner eller emulsjoner. Eventuelt er de sterilisert og/eller inneholder hjelpestoffer, som konserve-rings-, stabiliserings-, fuktnings- éller emulgeringsmidler,
salter til forandring av det osmotiske trykk eller puffer. De kan også inneholde andre terapeutisk verdifulle stoffer.
For den orale terapi kommer doser på 200-600 mg pr. medikasjon i betraktning. Slike doser kan administreres 2 til 4 ganger daglig.
Det folgende eksempel forklarer fremstillingen av forbindelsen j-følge. >~oppfinnelsen. Temperaturene er angitt i Celsius-grader.
Eksempel
26 g 6-aminokapronsyre i 345 ml 1,0 N natronlut tilsettes i lopet av 10 minutter ved 10° 58 g ampicillin-trihydrat og ro-res om ytterligere i 20 minutter. Derpå overfores oppløsningen til 1 kg Amberlite IR 120 og elueres med vann. Den vandige opplosning lyofiliseres, resten opploses i alkohol og felles med etylacetat. Det utfelte materiale omsetter man i metano-lisk opplosning med 2 N natriumetylkaproat i etylacetat og feller med eter. Fra metanol/eter får man etter behandling med dyrekull natriumsaltet av 6- (a-aminobenzyl-a-penicilloyl- '■ amino)-kapronsyre5smeltepunkt 157-160°, [a]^5 = +30,3° (l,o i vann).
Claims (1)
- Analogifrémgangsmåte for fremstilling av terapeutisk aktiv 6- (ct-aminobensyl-a-penicilloylamino) -kapronsyre med formelenog salter derav,karakterisert vedat man omsetter forbindelsen med formelmed 6-aminokapronsyreog, hvis ønsket, overfører reaksjonsproduktet til et salt.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH355871 | 1971-03-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO138142B true NO138142B (no) | 1978-04-03 |
| NO138142C NO138142C (no) | 1978-07-12 |
Family
ID=4258572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO790/72A NO138142C (no) | 1971-03-11 | 1972-03-10 | Analogifremgangsmaate for fremstilling av terapeutisk aktive 6(alfa-aminobenzyl-alfa-penicilloyl-amino)-kapronsyre og salter derav |
Country Status (21)
| Country | Link |
|---|---|
| AT (2) | AT312802B (no) |
| AU (1) | AU461136B2 (no) |
| BE (2) | BE780472A (no) |
| CA (1) | CA972759A (no) |
| CH (1) | CH546783A (no) |
| DE (2) | DE2211419A1 (no) |
| DK (1) | DK136977B (no) |
| ES (2) | ES400624A1 (no) |
| FI (1) | FI52345C (no) |
| FR (2) | FR2128823B1 (no) |
| GB (2) | GB1333524A (no) |
| HK (1) | HK14676A (no) |
| HU (2) | HU166712B (no) |
| IE (2) | IE36204B1 (no) |
| IL (2) | IL38865A (no) |
| NL (2) | NL7202771A (no) |
| NO (1) | NO138142C (no) |
| PH (2) | PH12264A (no) |
| SE (3) | SE406198B (no) |
| YU (1) | YU35011B (no) |
| ZA (2) | ZA721363B (no) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4316882A (en) * | 1978-04-20 | 1982-02-23 | Levine Bernard B | Compositions for testing to predict and/or diagnose allergy to penicillins |
| CA1209477A (en) * | 1981-03-26 | 1986-08-12 | Bruce E. Haeger | Composition of matter comprising a lyophilized preparation of a penicillin derivative |
-
1971
- 1971-03-11 CH CH355871A patent/CH546783A/xx not_active IP Right Cessation
-
1972
- 1972-03-01 ZA ZA721363A patent/ZA721363B/xx unknown
- 1972-03-01 ZA ZA721364A patent/ZA721364B/xx unknown
- 1972-03-01 IL IL38865A patent/IL38865A/xx unknown
- 1972-03-01 IL IL38864A patent/IL38864A/xx unknown
- 1972-03-02 PH PH13316A patent/PH12264A/en unknown
- 1972-03-02 AU AU39571/72A patent/AU461136B2/en not_active Expired
- 1972-03-02 NL NL7202771A patent/NL7202771A/xx not_active Application Discontinuation
- 1972-03-02 NL NL7202772A patent/NL7202772A/xx unknown
- 1972-03-03 PH PH13315*UA patent/PH9295A/en unknown
- 1972-03-06 CA CA136,277A patent/CA972759A/en not_active Expired
- 1972-03-07 IE IE282/72A patent/IE36204B1/xx unknown
- 1972-03-07 AT AT188772A patent/AT312802B/de not_active IP Right Cessation
- 1972-03-07 IE IE281/72A patent/IE36203B1/xx unknown
- 1972-03-07 AT AT188672A patent/AT331389B/de not_active IP Right Cessation
- 1972-03-08 FI FI720618A patent/FI52345C/fi active
- 1972-03-09 DE DE19722211419 patent/DE2211419A1/de active Pending
- 1972-03-09 DE DE19722211420 patent/DE2211420A1/de active Pending
- 1972-03-10 HU HUHO1459A patent/HU166712B/hu unknown
- 1972-03-10 SE SE7203125A patent/SE406198B/sv unknown
- 1972-03-10 GB GB1135272A patent/GB1333524A/en not_active Expired
- 1972-03-10 ES ES400624A patent/ES400624A1/es not_active Expired
- 1972-03-10 HU HUHO1460A patent/HU165203B/hu unknown
- 1972-03-10 DK DK112072AA patent/DK136977B/da unknown
- 1972-03-10 ES ES400623A patent/ES400623A1/es not_active Expired
- 1972-03-10 FR FR7208434A patent/FR2128823B1/fr not_active Expired
- 1972-03-10 GB GB1135172A patent/GB1322149A/en not_active Expired
- 1972-03-10 BE BE780472A patent/BE780472A/xx unknown
- 1972-03-10 NO NO790/72A patent/NO138142C/no unknown
- 1972-03-10 YU YU625/72A patent/YU35011B/xx unknown
- 1972-03-10 FR FR7208435A patent/FR2128824B1/fr not_active Expired
- 1972-03-10 BE BE780471A patent/BE780471A/xx unknown
-
1975
- 1975-12-08 SE SE7513807A patent/SE7513807L/xx unknown
- 1975-12-11 SE SE7514031A patent/SE7514031L/xx unknown
-
1976
- 1976-03-18 HK HK146/76*UA patent/HK14676A/xx unknown
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