CS197241B2 - Method of producing hydroxy-methyl pyridines from acetoxy-methyl pyridines - Google Patents
Method of producing hydroxy-methyl pyridines from acetoxy-methyl pyridines Download PDFInfo
- Publication number
- CS197241B2 CS197241B2 CS892474A CS892474A CS197241B2 CS 197241 B2 CS197241 B2 CS 197241B2 CS 892474 A CS892474 A CS 892474A CS 892474 A CS892474 A CS 892474A CS 197241 B2 CS197241 B2 CS 197241B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methanol
- base
- reaction mixture
- anhydrous
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- FAUHREUVDHNRIB-UHFFFAOYSA-N (2-methylpyridin-3-yl) acetate Chemical class CC(=O)OC1=CC=CN=C1C FAUHREUVDHNRIB-UHFFFAOYSA-N 0.000 title 1
- AQSRRZGQRFFFGS-UHFFFAOYSA-N 2-methylpyridin-3-ol Chemical class CC1=NC=CC=C1O AQSRRZGQRFFFGS-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 75
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical class OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 claims abstract description 18
- KEYZUMLVDCHSTP-UHFFFAOYSA-N pyridin-2-ylmethyl acetate Chemical class CC(=O)OCC1=CC=CC=N1 KEYZUMLVDCHSTP-UHFFFAOYSA-N 0.000 claims abstract description 18
- WWFMINHWJYHXHF-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl]methanol Chemical compound OCC1=CC=CC(CO)=N1 WWFMINHWJYHXHF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 14
- XARIFKSEVODEFM-UHFFFAOYSA-N [6-(acetyloxymethyl)pyridin-2-yl]methyl acetate Chemical compound C(C)(=O)OCC1=NC(=CC=C1)COC(C)=O XARIFKSEVODEFM-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- VSICEQUMRIDAGS-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl]methanol;hydrochloride Chemical compound Cl.OCC1=CC=CC(CO)=N1 VSICEQUMRIDAGS-UHFFFAOYSA-N 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 238000011156 evaluation Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- VURSFJLMQCEOCI-UHFFFAOYSA-N (2,6-dimethylpyridin-3-yl) acetate Chemical compound C(C)(=O)OC=1C(=NC(=CC=1)C)C VURSFJLMQCEOCI-UHFFFAOYSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000002327 cardiovascular agent Substances 0.000 abstract 1
- 229940125692 cardiovascular agent Drugs 0.000 abstract 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 8
- 238000006140 methanolysis reaction Methods 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- -1 dihydroxymethyl Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- UAPCKORZDAFJAB-UHFFFAOYSA-N pyridin-2-ylmethanediol Chemical class OC(O)C1=CC=CC=N1 UAPCKORZDAFJAB-UHFFFAOYSA-N 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- DAXJNUBSBFUTRP-RTQNCGMRSA-N (8r,9s,10r,13s,14s)-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(CO)C2=C1 DAXJNUBSBFUTRP-RTQNCGMRSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000012043 crude product Substances 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
- 238000002955 isolation Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- PTMBWNZJOQBTBK-UHFFFAOYSA-N pyridin-4-ylmethanol Chemical class OCC1=CC=NC=C1 PTMBWNZJOQBTBK-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- LIRQOUKPZWQBRE-UHFFFAOYSA-N (5-ethylpyridin-2-yl)methanol Chemical class CCC1=CC=C(CO)N=C1 LIRQOUKPZWQBRE-UHFFFAOYSA-N 0.000 description 1
- ZRNXOHYTSIFSDP-UHFFFAOYSA-N (6-methylpyridin-2-yl)methyl acetate Chemical compound CC(=O)OCC1=CC=CC(C)=N1 ZRNXOHYTSIFSDP-UHFFFAOYSA-N 0.000 description 1
- HATDKRFMRHQOCW-UHFFFAOYSA-N 1h-pyrrol-2-ylmethyl acetate Chemical group CC(=O)OCC1=CC=CN1 HATDKRFMRHQOCW-UHFFFAOYSA-N 0.000 description 1
- IGUIYPUGCIHEGB-UHFFFAOYSA-N 2-[2-(acetyloxymethyl)pyridin-3-yl]acetic acid Chemical compound CC(=O)OCC1=C(C=CC=N1)CC(=O)O IGUIYPUGCIHEGB-UHFFFAOYSA-N 0.000 description 1
- HBPKFYFSUQATFO-UHFFFAOYSA-N 2-methyl-1,2,3,6-tetrahydropyridine Chemical compound CC1CC=CCN1 HBPKFYFSUQATFO-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- JLVBSBMJQUMAMW-UHFFFAOYSA-N 6-methyl-2-pyridinemethanol Chemical compound CC1=CC=CC(CO)=N1 JLVBSBMJQUMAMW-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
- 150000001204 N-oxides Chemical class 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- FVRABHGHBLRNNR-UHFFFAOYSA-N liriodenine Natural products O=C1C=CC=c2c1cc3nccc4cc5OCOc5c2c34 FVRABHGHBLRNNR-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- GSOOLIFIQJUSFP-UHFFFAOYSA-N pyridin-2-ylmethanol;hydrochloride Chemical compound [Cl-].OCC1=CC=CC=[NH+]1 GSOOLIFIQJUSFP-UHFFFAOYSA-N 0.000 description 1
- ZGXKOLGDFWQRMM-UHFFFAOYSA-N pyridin-4-ylmethyl acetate Chemical compound CC(=O)OCC1=CC=NC=C1 ZGXKOLGDFWQRMM-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI000533 HU167834B (enrdf_load_stackoverflow) | 1973-12-29 | 1973-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS197241B2 true CS197241B2 (en) | 1980-04-30 |
Family
ID=11000944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS892474A CS197241B2 (en) | 1973-12-29 | 1974-12-22 | Method of producing hydroxy-methyl pyridines from acetoxy-methyl pyridines |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT339303B (enrdf_load_stackoverflow) |
| CH (1) | CH601235A5 (enrdf_load_stackoverflow) |
| CS (1) | CS197241B2 (enrdf_load_stackoverflow) |
| DD (1) | DD115903A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2460039C3 (enrdf_load_stackoverflow) |
| ES (1) | ES433392A1 (enrdf_load_stackoverflow) |
| HU (1) | HU167834B (enrdf_load_stackoverflow) |
| PL (1) | PL95853B1 (enrdf_load_stackoverflow) |
| SU (1) | SU510998A3 (enrdf_load_stackoverflow) |
| YU (1) | YU36928B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2835178A1 (de) * | 1978-08-11 | 1980-02-14 | Adidas Sportschuhe | Sportschuh, insbesondere laufschuh zur verwendung auf harten bahnen |
| DE19542035A1 (de) | 1995-11-10 | 1997-05-15 | Basf Ag | Verfahren zur Herstellung von hydroxyhaltigen Verbindungen aus Ameisensäureestern |
-
1973
- 1973-12-29 HU HURI000533 patent/HU167834B/hu unknown
-
1974
- 1974-12-12 CH CH1654274A patent/CH601235A5/xx not_active IP Right Cessation
- 1974-12-12 AT AT990174A patent/AT339303B/de not_active IP Right Cessation
- 1974-12-19 DE DE19742460039 patent/DE2460039C3/de not_active Expired
- 1974-12-22 CS CS892474A patent/CS197241B2/cs unknown
- 1974-12-23 DD DD18335574A patent/DD115903A5/xx unknown
- 1974-12-26 SU SU2091928A patent/SU510998A3/ru active
- 1974-12-27 ES ES433392A patent/ES433392A1/es not_active Expired
- 1974-12-27 YU YU348074A patent/YU36928B/xx unknown
- 1974-12-28 PL PL17690474A patent/PL95853B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT339303B (de) | 1977-10-10 |
| YU348074A (en) | 1982-06-18 |
| ES433392A1 (es) | 1976-12-01 |
| PL95853B1 (pl) | 1977-11-30 |
| HU167834B (enrdf_load_stackoverflow) | 1975-12-25 |
| ATA990174A (de) | 1977-02-15 |
| DD115903A5 (enrdf_load_stackoverflow) | 1975-10-20 |
| CH601235A5 (enrdf_load_stackoverflow) | 1978-06-30 |
| SU510998A3 (ru) | 1976-04-15 |
| DE2460039C3 (de) | 1979-03-01 |
| DE2460039A1 (de) | 1975-07-10 |
| DE2460039B2 (de) | 1978-06-29 |
| YU36928B (en) | 1984-08-31 |
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