FI57746C - Foerfarande foer framstaellning av icketoxiska syraadditionssalter av 1-bensyl-2,2-dimetylguanidin och 1-fenetyl-2,3-dimetylguanidin vilka anvaendes foer behandling av hjaertrytmstoerningar - Google Patents
Foerfarande foer framstaellning av icketoxiska syraadditionssalter av 1-bensyl-2,2-dimetylguanidin och 1-fenetyl-2,3-dimetylguanidin vilka anvaendes foer behandling av hjaertrytmstoerningar Download PDFInfo
- Publication number
- FI57746C FI57746C FI1567/71A FI156771A FI57746C FI 57746 C FI57746 C FI 57746C FI 1567/71 A FI1567/71 A FI 1567/71A FI 156771 A FI156771 A FI 156771A FI 57746 C FI57746 C FI 57746C
- Authority
- FI
- Finland
- Prior art keywords
- benzyl
- formula
- methyl
- salt
- hydrogen
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- 231100000252 nontoxic Toxicity 0.000 claims description 9
- 230000003000 nontoxic effect Effects 0.000 claims description 9
- 206010003119 arrhythmia Diseases 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- NBJVAZUWGSVCLO-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)guanidine Chemical compound C1(=CC=CC=C1)C(C)NC(=NC)NC NBJVAZUWGSVCLO-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 231100000331 toxic Toxicity 0.000 claims description 3
- 230000002588 toxic effect Effects 0.000 claims description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 101100116570 Caenorhabditis elegans cup-2 gene Proteins 0.000 claims 1
- 101100116572 Drosophila melanogaster Der-1 gene Proteins 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000003440 toxic substance Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 229960004980 betanidine Drugs 0.000 description 5
- NIVZHWNOUVJHKV-UHFFFAOYSA-N bethanidine Chemical compound CN\C(=N/C)NCC1=CC=CC=C1 NIVZHWNOUVJHKV-UHFFFAOYSA-N 0.000 description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N 1,1-dimethylguanidine Chemical compound CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000001077 hypotensive effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000005036 nerve Anatomy 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 230000002889 sympathetic effect Effects 0.000 description 3
- IYWTVNCXVBEYOK-UHFFFAOYSA-N 1,2-dimethyl-3-(2-phenylethyl)guanidine;hydroiodide Chemical compound I.CNC(=NC)NCCC1=CC=CC=C1 IYWTVNCXVBEYOK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010003658 Atrial Fibrillation Diseases 0.000 description 2
- PSZYOAUIDZHMEG-UHFFFAOYSA-N C(C(=O)O)(=O)O.CNC(=NCCC1=CC=CC=C1)NC Chemical compound C(C(=O)O)(=O)O.CNC(=NCCC1=CC=CC=C1)NC PSZYOAUIDZHMEG-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WPQZSUSLLBSFIH-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;iodide Chemical compound I.NC(N)=O WPQZSUSLLBSFIH-UHFFFAOYSA-N 0.000 description 2
- 230000006793 arrhythmia Effects 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000003663 ventricular fibrillation Diseases 0.000 description 2
- WDLCALUKNKNIDF-UHFFFAOYSA-N 1-benzyl-2,3-dimethylguanidine;sulfuric acid Chemical compound OS(O)(=O)=O.CN\C(=N/C)NCC1=CC=CC=C1 WDLCALUKNKNIDF-UHFFFAOYSA-N 0.000 description 1
- LMDZRUQWTMCXND-UHFFFAOYSA-N 2-benzyl-1,1-dimethylguanidine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C(N)=NCC1=CC=CC=C1 LMDZRUQWTMCXND-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000003440 anti-fibrillation Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- ACPFLXJEPKOPGF-UHFFFAOYSA-N diaminomethylidene(dimethyl)azanium;hydrogen sulfate Chemical compound [O-]S([O-])(=O)=O.C[NH+](C)C([NH3+])=N ACPFLXJEPKOPGF-UHFFFAOYSA-N 0.000 description 1
- IOPGBGMYUPEGOK-UHFFFAOYSA-N diethoxymethanimine Chemical compound CCOC(=N)OCC IOPGBGMYUPEGOK-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- SKHIBNDAFWIOPB-UHFFFAOYSA-N hydron;2-phenylethanamine;chloride Chemical compound Cl.NCCC1=CC=CC=C1 SKHIBNDAFWIOPB-UHFFFAOYSA-N 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- MROAQUNKLFXYQN-UHFFFAOYSA-N methanamine;sulfuric acid Chemical compound NC.OS(O)(=O)=O MROAQUNKLFXYQN-UHFFFAOYSA-N 0.000 description 1
- 210000000826 nictitating membrane Anatomy 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
Classifications
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2722070 | 1970-06-05 | ||
| GB2722070 | 1970-06-05 | ||
| GB2722170 | 1970-06-05 | ||
| GB2722270 | 1970-06-05 | ||
| GB2722170 | 1970-06-05 | ||
| GB2722270 | 1970-06-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57746B FI57746B (fi) | 1980-06-30 |
| FI57746C true FI57746C (fi) | 1980-10-10 |
Family
ID=27258609
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1567/71A FI57746C (fi) | 1970-06-05 | 1971-06-04 | Foerfarande foer framstaellning av icketoxiska syraadditionssalter av 1-bensyl-2,2-dimetylguanidin och 1-fenetyl-2,3-dimetylguanidin vilka anvaendes foer behandling av hjaertrytmstoerningar |
| FI802185A FI802185A7 (fi) | 1970-06-05 | 1980-07-08 | Menetelmä farmaseuttisen valmisteen valmistamiseksi, jota käytetään sydämen rytmihäiriöiden hoitamiseksi. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI802185A FI802185A7 (fi) | 1970-06-05 | 1980-07-08 | Menetelmä farmaseuttisen valmisteen valmistamiseksi, jota käytetään sydämen rytmihäiriöiden hoitamiseksi. |
Country Status (9)
| Country | Link |
|---|---|
| AR (2) | AR201263A1 (enrdf_load_stackoverflow) |
| BE (1) | BE768159A (enrdf_load_stackoverflow) |
| CA (1) | CA984297A (enrdf_load_stackoverflow) |
| CH (3) | CH605702A5 (enrdf_load_stackoverflow) |
| ES (2) | ES391920A1 (enrdf_load_stackoverflow) |
| FI (2) | FI57746C (enrdf_load_stackoverflow) |
| FR (1) | FR2100724B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1354513A (enrdf_load_stackoverflow) |
| IL (1) | IL36985A (enrdf_load_stackoverflow) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1302943A (fr) * | 1964-01-04 | 1962-09-07 | Wellcome Found | Benzylguanidines et leur préparation |
| DE1619538B1 (de) * | 1967-08-04 | 1971-06-24 | Bayer Ag | Verfahren zum Färben von Fasermaterialien aus Polyacrylnitril oder acrylnitrilhaltigen Mischpolymerisaten |
-
1970
- 1970-06-05 GB GB2722070A patent/GB1354513A/en not_active Expired
-
1971
- 1971-06-03 FR FR7120148A patent/FR2100724B1/fr not_active Expired
- 1971-06-04 ES ES391920A patent/ES391920A1/es not_active Expired
- 1971-06-04 CH CH816071A patent/CH605702A5/xx not_active IP Right Cessation
- 1971-06-04 FI FI1567/71A patent/FI57746C/fi active
- 1971-06-04 IL IL36985A patent/IL36985A/xx unknown
- 1971-06-04 BE BE768159A patent/BE768159A/xx not_active IP Right Cessation
- 1971-06-04 CA CA114,898A patent/CA984297A/en not_active Expired
-
1972
- 1972-05-19 AR AR242091A patent/AR201263A1/es active
- 1972-05-19 AR AR242092A patent/AR197871A1/es active
-
1974
- 1974-02-16 ES ES423342A patent/ES423342A1/es not_active Expired
-
1977
- 1977-10-24 CH CH1291577A patent/CH611274A5/xx not_active IP Right Cessation
- 1977-10-24 CH CH1291477A patent/CH613942A5/xx not_active IP Right Cessation
-
1980
- 1980-07-08 FI FI802185A patent/FI802185A7/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ES391920A1 (es) | 1974-12-16 |
| BE768159A (fr) | 1971-12-06 |
| CH605702A5 (enrdf_load_stackoverflow) | 1978-10-13 |
| FI802185A7 (fi) | 1981-01-01 |
| FR2100724B1 (enrdf_load_stackoverflow) | 1975-06-06 |
| AR201263A1 (es) | 1975-02-28 |
| FR2100724A1 (enrdf_load_stackoverflow) | 1972-03-24 |
| CH611274A5 (en) | 1979-05-31 |
| IL36985A (en) | 1975-03-13 |
| FI57746B (fi) | 1980-06-30 |
| ES423342A1 (es) | 1976-06-01 |
| GB1354513A (en) | 1974-06-05 |
| AR197871A1 (es) | 1974-05-15 |
| CH613942A5 (en) | 1979-10-31 |
| IL36985A0 (en) | 1971-08-25 |
| CA984297A (en) | 1976-02-24 |
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