IL42400A - Preparation of 2-alkoxy or alkenyloxy-4,5-substituted-aminoalkylbenzamides and certain new intermediates therefor - Google Patents
Preparation of 2-alkoxy or alkenyloxy-4,5-substituted-aminoalkylbenzamides and certain new intermediates thereforInfo
- Publication number
- IL42400A IL42400A IL42400A IL4240073A IL42400A IL 42400 A IL42400 A IL 42400A IL 42400 A IL42400 A IL 42400A IL 4240073 A IL4240073 A IL 4240073A IL 42400 A IL42400 A IL 42400A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- acid
- produced
- alkoxy
- mixture
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 4
- 239000000543 intermediate Substances 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 25
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 16
- 150000002540 isothiocyanates Chemical class 0.000 claims description 12
- -1 monoalkylamino Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000001035 drying Methods 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229940046892 lead acetate Drugs 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- LASJRIHCUCYPGY-UHFFFAOYSA-N n,n-diethyl-2-isothiocyanatoethanamine Chemical compound CCN(CC)CCN=C=S LASJRIHCUCYPGY-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000003936 benzamides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- XCAUINMIESBTBL-UHFFFAOYSA-N lead(ii) sulfide Chemical compound [Pb]=S XCAUINMIESBTBL-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KMTVCPOROYMLTN-UHFFFAOYSA-N 1-(2-isothiocyanatoethyl)piperidine Chemical compound S=C=NCCN1CCCCC1 KMTVCPOROYMLTN-UHFFFAOYSA-N 0.000 description 1
- SJXGCZHADALIJA-UHFFFAOYSA-N 2-(diethylamino)ethylcarbamodithioic acid Chemical compound CCN(CC)CCNC(S)=S SJXGCZHADALIJA-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 description 1
- CJKJNTJPOYSDQL-UHFFFAOYSA-N 2-methylsulfonylbenzamide Chemical compound CS(=O)(=O)C1=CC=CC=C1C(N)=O CJKJNTJPOYSDQL-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- DDAMPNWYDILDPV-UHFFFAOYSA-N benzamide;phosphoric acid Chemical compound OP(O)(O)=O.NC(=O)C1=CC=CC=C1 DDAMPNWYDILDPV-UHFFFAOYSA-N 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- APGXDGZXGZROMN-UHFFFAOYSA-N n-piperidin-1-ium-1-ylcarbamodithioate Chemical compound SC(=S)NN1CCCCC1 APGXDGZXGZROMN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Furan Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7220042A FR2188600A5 (en) | 1972-06-02 | 1972-06-02 | N-(substd alkyl)-2-alk(enyl)oxybenzamides - antiemetics digestion-regulators and psychotropics |
| FR7220041A FR2187779A1 (en) | 1972-06-02 | 1972-06-02 | N-(substd alkyl)-2-alk(enyl)oxybenzamides - antiemetics digestion-regulators and psychotropics |
| FR7225671A FR2192102A1 (en) | 1972-07-13 | 1972-07-13 | N-(substd alkyl)-2-alk(enyl)oxybenzamides - antiemetics digestion-regulators and psychotropics |
| FR7225670A FR2192556A5 (en) | 1972-07-13 | 1972-07-13 | N-(substd alkyl)-2-alk(enyl)oxybenzamides - antiemetics digestion-regulators and psychotropics |
| FR7312392A FR2224448A1 (en) | 1973-04-05 | 1973-04-05 | N-(substd alkyl)-2-alk(enyl)oxybenzamides - antiemetics digestion-regulators and psychotropics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42400A0 IL42400A0 (en) | 1973-07-30 |
| IL42400A true IL42400A (en) | 1977-08-31 |
Family
ID=27515375
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42400A IL42400A (en) | 1972-06-02 | 1973-05-30 | Preparation of 2-alkoxy or alkenyloxy-4,5-substituted-aminoalkylbenzamides and certain new intermediates therefor |
| IL48880A IL48880A (en) | 1972-06-02 | 1973-05-30 | Isothiocyanates and their preparation |
| IL48880A IL48880A0 (en) | 1972-06-02 | 1976-01-20 | Novel isothiocyanates and their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL48880A IL48880A (en) | 1972-06-02 | 1973-05-30 | Isothiocyanates and their preparation |
| IL48880A IL48880A0 (en) | 1972-06-02 | 1976-01-20 | Novel isothiocyanates and their preparation |
Country Status (17)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2305176A1 (fr) * | 1975-03-28 | 1976-10-22 | Ile De France | Nouveau medicament a base de n-(diethylaminoethyl) 2-methoxy-5-methyl-sulfonyl benzamide |
| CH614709A5 (enrdf_load_stackoverflow) * | 1975-09-25 | 1979-12-14 | Ciba Geigy Ag |
-
1973
- 1973-05-28 PH PH14664*UA patent/PH9265A/en unknown
- 1973-05-29 CS CS3876A patent/CS174886B2/cs unknown
- 1973-05-29 DE DE2327414A patent/DE2327414C2/de not_active Expired
- 1973-05-29 YU YU01421/73A patent/YU39107B/xx unknown
- 1973-05-29 JP JP6076573A patent/JPS5537545B2/ja not_active Expired
- 1973-05-29 BG BG023737A patent/BG21854A3/xx unknown
- 1973-05-30 IL IL42400A patent/IL42400A/en unknown
- 1973-05-30 HU HUSO1081A patent/HU168115B/hu unknown
- 1973-05-30 IE IE866/73A patent/IE37726B1/xx unknown
- 1973-05-30 BE BE1005109A patent/BE800234A/xx not_active IP Right Cessation
- 1973-05-30 CH CH785973A patent/CH575913A5/xx not_active IP Right Cessation
- 1973-05-30 IL IL48880A patent/IL48880A/xx unknown
- 1973-05-31 RO RO197374983A patent/RO73007A/ro unknown
- 1973-05-31 DD DD171219A patent/DD109617A5/xx unknown
- 1973-06-01 GB GB3253875A patent/GB1422223A/en not_active Expired
- 1973-06-01 GB GB2627373A patent/GB1422221A/en not_active Expired
- 1973-06-01 CA CA172,965A patent/CA1016175A/en not_active Expired
- 1973-06-01 GB GB582375A patent/GB1422222A/en not_active Expired
- 1973-06-01 LU LU67729A patent/LU67729A1/xx unknown
- 1973-08-17 JP JP48092346A patent/JPS5070323A/ja active Pending
- 1973-09-20 AU AU60514/73A patent/AU476711B2/en not_active Expired
-
1976
- 1976-01-20 IL IL48880A patent/IL48880A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE800234A (fr) | 1973-11-30 |
| PH9265A (en) | 1975-07-30 |
| CA1016175A (en) | 1977-08-23 |
| IL48880A0 (en) | 1976-03-31 |
| GB1422223A (en) | 1976-01-21 |
| YU142173A (en) | 1982-06-30 |
| HU168115B (enrdf_load_stackoverflow) | 1976-02-28 |
| LU67729A1 (enrdf_load_stackoverflow) | 1974-07-05 |
| AU6051473A (en) | 1975-03-20 |
| BG21854A3 (bg) | 1976-09-20 |
| DD109617A5 (enrdf_load_stackoverflow) | 1974-11-12 |
| GB1422222A (en) | 1976-01-21 |
| IE37726B1 (en) | 1977-09-28 |
| IE37726L (en) | 1973-12-02 |
| DE2327414A1 (de) | 1973-12-13 |
| AU476711B2 (en) | 1976-09-30 |
| CH575913A5 (enrdf_load_stackoverflow) | 1976-05-31 |
| IL42400A0 (en) | 1973-07-30 |
| RO73007A (fr) | 1981-11-04 |
| JPS4985038A (enrdf_load_stackoverflow) | 1974-08-15 |
| IL48880A (en) | 1977-10-31 |
| JPS5070323A (enrdf_load_stackoverflow) | 1975-06-11 |
| JPS5537545B2 (enrdf_load_stackoverflow) | 1980-09-29 |
| CS174886B2 (enrdf_load_stackoverflow) | 1977-04-29 |
| GB1422221A (en) | 1976-01-21 |
| DE2327414C2 (de) | 1983-02-17 |
| YU39107B (en) | 1984-06-30 |
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