SU465007A3 - Способ получени сложных эфиров 2-алкилтиазол-5-карбоновой кислоты - Google Patents
Способ получени сложных эфиров 2-алкилтиазол-5-карбоновой кислотыInfo
- Publication number
- SU465007A3 SU465007A3 SU1792313A SU1792313A SU465007A3 SU 465007 A3 SU465007 A3 SU 465007A3 SU 1792313 A SU1792313 A SU 1792313A SU 1792313 A SU1792313 A SU 1792313A SU 465007 A3 SU465007 A3 SU 465007A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- ether
- carboxylic acid
- acetone
- solution
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 116
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 105
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
- 239000000243 solution Substances 0.000 description 50
- -1 methoxy, ethoxy Chemical group 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000002253 acid Substances 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- IOSZDNOGOPHEPH-UHFFFAOYSA-N 2-propyl-1,3-thiazole-5-carboxylic acid Chemical compound CCCC1=NC=C(C(O)=O)S1 IOSZDNOGOPHEPH-UHFFFAOYSA-N 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 125000004494 ethyl ester group Chemical group 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
- 239000011976 maleic acid Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000002211 ultraviolet spectrum Methods 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- YZVFSQQHQPPKNX-UHFFFAOYSA-N 1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CS1 YZVFSQQHQPPKNX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HTGCVLNFLVVCST-UHFFFAOYSA-N 1-piperazin-1-ylethanol Chemical compound CC(O)N1CCNCC1 HTGCVLNFLVVCST-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- MOXHFAKEWAXEAX-UHFFFAOYSA-N 1-[4-(2-ethoxyphenyl)piperazin-1-yl]ethanol Chemical compound CCOC1=CC=CC=C1N1CCN(C(C)O)CC1 MOXHFAKEWAXEAX-UHFFFAOYSA-N 0.000 description 2
- GAYUEVJYRZZYQK-UHFFFAOYSA-N 1-[4-(2-methoxyphenyl)piperazin-1-yl]ethanol Chemical compound COC1=CC=CC=C1N1CCN(C(C)O)CC1 GAYUEVJYRZZYQK-UHFFFAOYSA-N 0.000 description 2
- QCXCIYPOMMIBHO-UHFFFAOYSA-N 2-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC1=NC=C(C(O)=O)S1 QCXCIYPOMMIBHO-UHFFFAOYSA-N 0.000 description 2
- WCTXVLFQFQHNIC-UHFFFAOYSA-N 4-ethyl-2-propyl-1,3-thiazole-5-carboxylic acid Chemical compound CCCC1=NC(CC)=C(C(O)=O)S1 WCTXVLFQFQHNIC-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- MWWWSLZJPVXZCM-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)ethanol Chemical compound C(C1=CC=CC=C1)N1CCN(CC1)C(C)O MWWWSLZJPVXZCM-UHFFFAOYSA-N 0.000 description 1
- TWYOUDMVPKKSFG-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)piperazin-1-yl]ethanol Chemical compound ClC1=C(C=CC=C1)N1CCN(CC1)C(C)O TWYOUDMVPKKSFG-UHFFFAOYSA-N 0.000 description 1
- AZCOZURUZYWULA-UHFFFAOYSA-N 1-[4-(2-methylphenyl)piperazin-1-yl]ethanol Chemical compound C1(=C(C=CC=C1)N1CCN(CC1)C(C)O)C AZCOZURUZYWULA-UHFFFAOYSA-N 0.000 description 1
- UQUPPLFTEGJWPV-UHFFFAOYSA-N 1-[4-(4-methylphenyl)piperazin-1-yl]ethanol Chemical compound C1(=CC=C(C=C1)N1CCN(CC1)C(C)O)C UQUPPLFTEGJWPV-UHFFFAOYSA-N 0.000 description 1
- KNQNDRIJHNYXGG-UHFFFAOYSA-N 1-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(C(O)C)CCN1C1=CC=CC(C(F)(F)F)=C1 KNQNDRIJHNYXGG-UHFFFAOYSA-N 0.000 description 1
- VHTFTFTUQPIYPF-UHFFFAOYSA-N 2-(2-ethoxyphenyl)piperazine Chemical compound CCOC1=CC=CC=C1C1NCCNC1 VHTFTFTUQPIYPF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BNKZFUBCZHESJT-UHFFFAOYSA-N 2-butyl-1,3-thiazole-5-carboxylic acid Chemical compound CCCCC1=NC=C(C(O)=O)S1 BNKZFUBCZHESJT-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- OIJVSQBQVLWHQR-UHFFFAOYSA-N ethyl 2-butyl-1,3-thiazole-5-carboxylate Chemical compound CCCCC1=NC=C(S1)C(=O)OCC OIJVSQBQVLWHQR-UHFFFAOYSA-N 0.000 description 1
- XMCNMSAYSUPIOF-UHFFFAOYSA-N ethyl 2-propyl-1,3-thiazole-5-carboxylate Chemical compound CCCC1=NC=C(C(=O)OCC)S1 XMCNMSAYSUPIOF-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001394 sodium malate Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7121466A FR2141526B1 (enrdf_load_stackoverflow) | 1971-06-14 | 1971-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU465007A3 true SU465007A3 (ru) | 1975-03-25 |
Family
ID=9078582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1792313A SU465007A3 (ru) | 1971-06-14 | 1972-06-09 | Способ получени сложных эфиров 2-алкилтиазол-5-карбоновой кислоты |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5515477B1 (enrdf_load_stackoverflow) |
| DD (1) | DD99799A5 (enrdf_load_stackoverflow) |
| DK (1) | DK145224C (enrdf_load_stackoverflow) |
| ES (1) | ES403786A1 (enrdf_load_stackoverflow) |
| HU (1) | HU163928B (enrdf_load_stackoverflow) |
| IL (1) | IL39611A (enrdf_load_stackoverflow) |
| SU (1) | SU465007A3 (enrdf_load_stackoverflow) |
| ZA (1) | ZA724090B (enrdf_load_stackoverflow) |
-
1972
- 1972-06-06 IL IL39611A patent/IL39611A/xx unknown
- 1972-06-09 SU SU1792313A patent/SU465007A3/ru active
- 1972-06-09 DD DD16358272A patent/DD99799A5/xx unknown
- 1972-06-13 HU HURO000664 patent/HU163928B/hu unknown
- 1972-06-13 ES ES403786A patent/ES403786A1/es not_active Expired
- 1972-06-14 ZA ZA724090A patent/ZA724090B/xx unknown
- 1972-06-14 JP JP5869472A patent/JPS5515477B1/ja active Pending
- 1972-06-14 DK DK295272A patent/DK145224C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK145224B (da) | 1982-10-11 |
| DD99799A5 (enrdf_load_stackoverflow) | 1973-08-20 |
| ES403786A1 (es) | 1975-05-16 |
| HU163928B (enrdf_load_stackoverflow) | 1973-11-28 |
| IL39611A0 (en) | 1972-08-30 |
| ZA724090B (en) | 1973-03-28 |
| DK145224C (da) | 1983-03-07 |
| IL39611A (en) | 1975-07-28 |
| JPS5515477B1 (enrdf_load_stackoverflow) | 1980-04-23 |
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