NO138142B - ANALOGICAL PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 6 (ALFA-AMINOBENZYL-ALFA-PENICILLOYL-AMINO) -CAPRONIC ACID AND SALTS thereof - Google Patents
ANALOGICAL PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 6 (ALFA-AMINOBENZYL-ALFA-PENICILLOYL-AMINO) -CAPRONIC ACID AND SALTS thereof 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)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (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 The present invention relates to the preparation of 6-(α-.aminobenzyl-α-penicilloylamino)-caproic acid with the formula
såvel salter derav. as well as salts thereof.
Forbindelsen med formel I kan også foreligge som salter, f. The compound of formula I can also exist as salts, e.g.
eks- som Na-, K— eller Ca-salt. Videre kan forbindelsen foreligge som et indre salt, hvorved saltdannelsen skjer mellom aminogruppe og karboksylgruppe. ex- such as Na-, K- or Ca-salt. Furthermore, the compound can exist as an internal salt, whereby the salt formation takes place between the amino group and the carboxyl group.
Forbindelsen med formel I og dens salter kan fremstilles The compound of formula I and its salts can be prepared
ved at man omsetter en forbindélse med den generelle formel by converting a compound with the general formula
med 6-aminokapronsyre og overfører, hvis ønsket, reaksjons- with 6-aminocaproic acid and transfers, if desired, reaction
produktet til et salt. the product into a salt.
Omsetningen av forbinelsen med formel II med 6-aminokapron- The reaction of the compound of formula II with 6-aminocapron-
syre foretas hensiktsmessig i vandig-alkalisk medium. Reak- acid is conveniently carried out in an aqueous-alkaline medium. Reac-
sjonsstemperaturen er fortrinnsvis 5 - 30°C. the reaction temperature is preferably 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. The compound of formula I and its pharmaceutically acceptable salts can be used to inhibit allergic reactions. which acts by administration-of 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- Thus, the in vitro precipitation of anti-pencilloyl antibodies, above all anti-ampicilloyl antibodies (extracted from rabbit and guinea pig sera) could be inhibited by pencilloyl antigens with the help of 6-(α-aminobenzyl- α-penicilloyl-amino)caproic acid. Furthermore, it was found that the aforementioned penicilloic acid derivative inhibits hemagglutination of pre-coated erythrocytes by ampicilloyl antigens with anti-penicilloyl antibodies, above all anti-ampicilloyl antibodies. Similarly, the contraction induced by ampicilloyl antigens in guinea pig ileum passively sensitized by anti-ampicilloyl rabbit γ-globulin (Schultz-Dale-forsdk) was inhibited. In vivo, 6-(α-aminobenzyl-α-penicilloyl-amino)-caproic acid could cause penicillin-allergic reactions, such as the passive skin
: anaphylaxi hos marsvin såvel som den urtikarielle hudreaksjon, i hos ampicillinalergiske mennesker, hemmes. Det analoge gjel-^: anaphylaxis in guinea pigs as well as the urticarial skin reaction in ampicillin-allergic people are inhibited. The analogous gill-^
der for 6-[a-amino- (1,4-cykloheksadienyl)metyl-a-penicilloyl- : aminoj-kapronsyre. there for 6-[α-amino-(1,4-cyclohexadienyl)methyl-α-penicilloyl-: aminoj-caproic acid.
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. The following test report shows the effect of the process product compared with N 6 -(benzyl-a-penicilloyl-N 2-formyl-L-lysine produced according to Danish patent no-, 125 250.
F 0_R_S_0_K_S_R_A_P_P_0 RT F 0_R_S_0_K_S_R_A_P_P_0 RT
Formål: Purpose:
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 - To assess the relative activity for 6-(oc-aminobenzyl-α-pehicilloylamino)-caproic acid, prepared according to application No. 790/72 hereinafter referred to as compound A, and 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. (benzyl-oc-penicilloyl)-N 2-formyl-L-lysine, prepared according to Danish patent no. 125,250 and hereinafter referred to as compound B, for the inhibition of experimental allergic reactions caused by ampicillin.
Fr emqanq småt éi Fr emqanq small éi
Antilegemer fremstilles i kaniner ved konjugater av ampicillin med okso-gamma-globulin i fullstendig Freund's hjelpemiddel. Antibodies are produced in rabbits by conjugates of ampicillin with oxo-gamma-globulin in complete Freund's adjuvant.
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 These antisera are injected intradermally in various dilutions. groups of 4 guinea pigs, which 24 hours later intravenously receive 1 mg of the conjugate formed of ampicillin with poly-lysine. The inhibitory hapten, i.e. compound A or B, is co-injected at doses of lOO, 20, 10 and 1 mg together with
0,5 ml 1%'s Evans blått. De uttredende blå reaksjoner (passive kutane anaphylaktiske reaksjoner) måles 30 minutter senere. 0.5 ml 1% Evans blue. The resulting blue reactions (passive cutaneous anaphylactic reactions) are measured 30 minutes later.
I tabellen nedenfor er disse reaksjoner uttrykt i % av de reaksjoner som oppnåes i dyr som ikke ble behandlet med det inhiberende hapten. In the table below, these reactions are expressed in % of the reactions obtained in animals that were not treated with the inhibitory hapten.
Resultater; Results;
Konklus j oner Conclusions
Forbindelse Å er langt mere effektiv enn forbindelse B til Compound Å is far more effective than compound B
å hemme allergistiske reaksjoner som skyldes ampicillin. to inhibit allergic reactions caused by 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, Process product-t: .can find application in the form of f arma-;! soy preparations containing this or its salts in mixture with a pharmaceutical organic or inorganic inert carrier material suitable for enteral or parenteral administration, such as e.g. water, plant oils, polyalkylene glycols, etc. The pharmaceutical preparations can be present, e.g. as readings, suspensions or emulsions. If necessary, they are sterilized and/or contain auxiliary substances, such as preservatives, stabilisers, wetting or emulsifying agents,
salter til forandring av det osmotiske trykk eller puffer. De kan også inneholde andre terapeutisk verdifulle stoffer. salts to change the osmotic pressure or puff. They may also contain other therapeutically valuable substances.
For den orale terapi kommer doser på 200-600 mg pr. medikasjon i betraktning. Slike doser kan administreres 2 til 4 ganger daglig. For the oral therapy, doses of 200-600 mg per medication into consideration. Such doses can be administered 2 to 4 times daily.
Det folgende eksempel forklarer fremstillingen av forbindelsen j-følge. >~oppfinnelsen. Temperaturene er angitt i Celsius-grader. The following example explains the production of the compound j-following. >~the invention. Temperatures are given in degrees Celsius.
Eksempel Example
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). 26 g of 6-aminocaproic acid in 345 ml of 1.0 N caustic soda are added over the course of 10 minutes at 10° to 58 g of ampicillin trihydrate and stirred for a further 20 minutes. The solution is then transferred to 1 kg of Amberlite IR 120 and eluted with water. The aqueous solution is lyophilized, the residue is dissolved in alcohol and combined with ethyl acetate. The precipitated material is reacted in a methanolic solution with 2 N sodium ethyl caproate in ethyl acetate and precipitated with ether. From methanol/ether, after treatment with animal charcoal, the sodium salt of 6-(α-aminobenzyl-α-penicilloyl-'■ amino)-caproic acid is obtained, melting point 157-160°, [a]^5 = +30.3° (l,o in water ).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH355871 | 1971-03-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO138142B true NO138142B (en) | 1978-04-03 |
| NO138142C NO138142C (en) | 1978-07-12 |
Family
ID=4258572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO790/72A NO138142C (en) | 1971-03-11 | 1972-03-10 | ANALOGICAL PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 6 (ALFA-AMINOBENZYL-ALFA-PENICILLOYL-AMINO) -CAPRONIC ACID AND SALTS thereof |
Country Status (21)
| Country | Link |
|---|---|
| AT (2) | AT331389B (en) |
| AU (1) | AU461136B2 (en) |
| BE (2) | BE780471A (en) |
| CA (1) | CA972759A (en) |
| CH (1) | CH546783A (en) |
| DE (2) | DE2211419A1 (en) |
| DK (1) | DK136977B (en) |
| ES (2) | ES400624A1 (en) |
| FI (1) | FI52345C (en) |
| FR (2) | FR2128823B1 (en) |
| GB (2) | GB1322149A (en) |
| HK (1) | HK14676A (en) |
| HU (2) | HU166712B (en) |
| IE (2) | IE36204B1 (en) |
| IL (2) | IL38865A (en) |
| NL (2) | NL7202772A (en) |
| NO (1) | NO138142C (en) |
| PH (2) | PH12264A (en) |
| SE (3) | SE406198B (en) |
| YU (1) | YU35011B (en) |
| ZA (2) | ZA721364B (en) |
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/en not_active IP Right Cessation
-
1972
- 1972-03-01 IL IL38865A patent/IL38865A/en unknown
- 1972-03-01 IL IL38864A patent/IL38864A/en unknown
- 1972-03-01 ZA ZA721364A patent/ZA721364B/en unknown
- 1972-03-01 ZA ZA721363A patent/ZA721363B/en unknown
- 1972-03-02 PH PH13316A patent/PH12264A/en unknown
- 1972-03-02 NL NL7202772A patent/NL7202772A/xx 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
- 1972-03-03 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/en unknown
- 1972-03-07 IE IE281/72A patent/IE36203B1/en unknown
- 1972-03-07 AT AT188672A patent/AT331389B/en not_active IP Right Cessation
- 1972-03-07 AT AT188772A patent/AT312802B/en not_active IP Right Cessation
- 1972-03-08 FI FI720618A patent/FI52345C/en active
- 1972-03-09 DE DE19722211419 patent/DE2211419A1/en active Pending
- 1972-03-09 DE DE19722211420 patent/DE2211420A1/en active Pending
- 1972-03-10 YU YU625/72A patent/YU35011B/en unknown
- 1972-03-10 BE BE780471A patent/BE780471A/en unknown
- 1972-03-10 HU HUHO1459A patent/HU166712B/hu unknown
- 1972-03-10 HU HUHO1460A patent/HU165203B/hu unknown
- 1972-03-10 FR FR7208434A patent/FR2128823B1/fr not_active Expired
- 1972-03-10 NO NO790/72A patent/NO138142C/en unknown
- 1972-03-10 ES ES400624A patent/ES400624A1/en not_active Expired
- 1972-03-10 ES ES400623A patent/ES400623A1/en not_active Expired
- 1972-03-10 FR FR7208435A patent/FR2128824B1/fr not_active Expired
- 1972-03-10 GB GB1135172A patent/GB1322149A/en not_active Expired
- 1972-03-10 BE BE780472A patent/BE780472A/en unknown
- 1972-03-10 DK DK112072AA patent/DK136977B/en unknown
- 1972-03-10 SE SE7203125A patent/SE406198B/en unknown
- 1972-03-10 GB GB1135272A patent/GB1333524A/en not_active Expired
-
1975
- 1975-12-08 SE SE7513807A patent/SE7513807L/en unknown
- 1975-12-11 SE SE7514031A patent/SE7514031L/en unknown
-
1976
- 1976-03-18 HK HK146/76*UA patent/HK14676A/en unknown
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