HU196368B - Process for production of 1-/3-brom-/25/-methil-prophionil/-pirrolidin-/25/-carbonic acid - Google Patents
Process for production of 1-/3-brom-/25/-methil-prophionil/-pirrolidin-/25/-carbonic acid Download PDFInfo
- Publication number
- HU196368B HU196368B HU862811A HU281186A HU196368B HU 196368 B HU196368 B HU 196368B HU 862811 A HU862811 A HU 862811A HU 281186 A HU281186 A HU 281186A HU 196368 B HU196368 B HU 196368B
- Authority
- HU
- Hungary
- Prior art keywords
- bromo
- methyl
- acid
- benzyl ester
- pyrrolidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 17
- BUPXDXGYFXDDAA-GSVOUGTGSA-N (2s)-3-bromo-2-methylpropanoic acid Chemical compound BrC[C@@H](C)C(O)=O BUPXDXGYFXDDAA-GSVOUGTGSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
- VVCLBQFBKZQOAF-NSHDSACASA-N benzyl (2s)-pyrrolidine-2-carboxylate Chemical compound O=C([C@H]1NCCC1)OCC1=CC=CC=C1 VVCLBQFBKZQOAF-NSHDSACASA-N 0.000 claims description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 150000004682 monohydrates Chemical class 0.000 claims description 4
- 150000001718 carbodiimides Chemical group 0.000 claims description 3
- BUPXDXGYFXDDAA-VKHMYHEASA-N (2r)-3-bromo-2-methylpropanoic acid Chemical compound BrC[C@H](C)C(O)=O BUPXDXGYFXDDAA-VKHMYHEASA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 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 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 6
- 229930182821 L-proline Natural products 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- BUPXDXGYFXDDAA-UHFFFAOYSA-N 3-bromo-2-methylpropanoic acid Chemical compound BrCC(C)C(O)=O BUPXDXGYFXDDAA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- -1 benzyl ester Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- NEDMOHHWRPHBAL-MERQFXBCSA-N benzyl (2s)-pyrrolidin-1-ium-2-carboxylate;chloride Chemical compound Cl.O=C([C@H]1NCCC1)OCC1=CC=CC=C1 NEDMOHHWRPHBAL-MERQFXBCSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- VGLKHVQPWGFXEG-NCJHBDPTSA-K europium(3+);(1z)-2,2,3,3,4,4,4-heptafluoro-1-(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)butan-1-olate Chemical compound [Eu+3].C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C.C1CC2(C)C(=O)\C(=C(/[O-])C(F)(F)C(F)(F)C(F)(F)F)C1C2(C)C VGLKHVQPWGFXEG-NCJHBDPTSA-K 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZHHOUXSQMHJPRA-ZETCQYMHSA-N trimethylsilyl (2s)-pyrrolidine-2-carboxylate Chemical compound C[Si](C)(C)OC(=O)[C@@H]1CCCN1 ZHHOUXSQMHJPRA-ZETCQYMHSA-N 0.000 description 1
Classifications
-
- 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
- C07D207/10—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 hetero atoms or 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
- C07D207/12—Oxygen or sulfur atoms
-
- 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
- C07D207/10—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 hetero atoms or 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B9/00—General processes of refining or remelting of metals; Apparatus for electroslag or arc remelting of metals
- C22B9/02—Refining by liquating, filtering, centrifuging, distilling, or supersonic wave action including acoustic waves
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Acoustics & Sound (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU862811A HU196368B (en) | 1986-07-04 | 1986-07-04 | Process for production of 1-/3-brom-/25/-methil-prophionil/-pirrolidin-/25/-carbonic acid |
| YU01180/87A YU118087A (en) | 1986-07-04 | 1987-06-24 | Process for obtaining acylated heterocyclic substance |
| CH2523/87A CH672786A5 (enrdf_load_stackoverflow) | 1986-07-04 | 1987-07-02 | |
| IT21179/87A IT1221952B (it) | 1986-07-04 | 1987-07-03 | Procedimento per preparare un composto eterociclico acilato |
| CS875051A CS262693B2 (en) | 1986-07-04 | 1987-07-03 | Process for preparing 1-/3-brom-/2s/-methylpropionyl/pyrrolidin-/2s/-carboxylic acid |
| ES8701951A ES2004443A6 (es) | 1986-07-04 | 1987-07-03 | Procedimiento de preparacion del acido 1-(3-bromo-(2s)-metilpropionil)-pirrolidin-(2s)-carboxilico |
| NO872796A NO872796L (no) | 1986-07-04 | 1987-07-03 | Fremgangsmte for fremstilling av en acylert heterocyklisk forbindelse. |
| PL1987266620A PL150350B1 (en) | 1986-07-04 | 1987-07-03 | Method of obtaining 1-3-bromo-/2s/-methylpropionyl -pyrrolidine-/2s/-carboxylic acid of formula 1 and its monohydride |
| JP62166755A JPS6322557A (ja) | 1986-07-04 | 1987-07-03 | アシル化複素環化合物の製造方法 |
| DK343587A DK343587A (da) | 1986-07-04 | 1987-07-03 | Acylerede heterocycliske forbindelser |
| DD87304596A DD263984A5 (de) | 1986-07-04 | 1987-07-03 | Verfahren zur herstellung von 1-[3-brom-(2s)-methylpropionyl]-pyrrolidin-(2s)-carbonsaeure |
| AT0168087A AT387382B (de) | 1986-07-04 | 1987-07-03 | Verfahren zur herstellung eines bromacylprolins |
| SE8702753A SE8702753L (sv) | 1986-07-04 | 1987-07-03 | Forfarande for framstellning av en acylerad heterocyklisk forening |
| PT85256A PT85256B (pt) | 1986-07-04 | 1987-07-03 | Processo para a preparacao de acido 1-(3-bromo-{2s}-metilpropionil)-pirrolidino-{2s}-carboxilico |
| FI872966A FI872966A7 (fi) | 1986-07-04 | 1987-07-03 | Foerfarande foer framstaellning av en acylerad heterocyklisk foerening. |
| CN198787104582A CN87104582A (zh) | 1986-07-04 | 1987-07-03 | 制备酰化的杂环化合物的方法 |
| GR871051A GR871051B (en) | 1986-07-04 | 1987-07-03 | A process for preparing an acylated heterocyclic compound |
| KR1019870007155A KR880001589A (ko) | 1986-07-04 | 1987-07-04 | 아실화된 헤테르고리 화합물의 제조방법 |
| DE19873722278 DE3722278A1 (de) | 1986-07-04 | 1987-07-06 | Verfahren zur herstellung von 1-(3'-(brom)-(2's)-(methyl)-propionyl) -pyrrolidin-(2s)-carbonsaeure oder ihres monohydrates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU862811A HU196368B (en) | 1986-07-04 | 1986-07-04 | Process for production of 1-/3-brom-/25/-methil-prophionil/-pirrolidin-/25/-carbonic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT44491A HUT44491A (en) | 1988-03-28 |
| HU196368B true HU196368B (en) | 1988-11-28 |
Family
ID=10961203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU862811A HU196368B (en) | 1986-07-04 | 1986-07-04 | Process for production of 1-/3-brom-/25/-methil-prophionil/-pirrolidin-/25/-carbonic acid |
Country Status (19)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8802849A (nl) * | 1988-11-18 | 1990-06-18 | Stamicarbon | Werkwijze voor de enantioselectieve bereiding van d-(-)-3-hal-methylpropionzuur of derivaten daarvan en de bereiding van captopril daaruit. |
| CN103086939A (zh) * | 2011-10-28 | 2013-05-08 | 华中药业股份有限公司 | 1-(3-溴-2-d-甲基丙酰基)吡咯烷-2-羧酸的重结晶方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU184082B (en) * | 1979-12-29 | 1984-06-28 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing 1-3-/3mercapto-/2s/-methyl-propinyl/-pyrrolidine-/2s/-carboxylic acid |
| IE50839B1 (en) * | 1980-02-26 | 1986-07-23 | Wyeth John & Brother Ltd | Novel processes for preparing proline derivatives and analogous compounds |
-
1986
- 1986-07-04 HU HU862811A patent/HU196368B/hu unknown
-
1987
- 1987-06-24 YU YU01180/87A patent/YU118087A/xx unknown
- 1987-07-02 CH CH2523/87A patent/CH672786A5/de not_active IP Right Cessation
- 1987-07-03 GR GR871051A patent/GR871051B/el unknown
- 1987-07-03 FI FI872966A patent/FI872966A7/fi not_active Application Discontinuation
- 1987-07-03 CS CS875051A patent/CS262693B2/cs unknown
- 1987-07-03 ES ES8701951A patent/ES2004443A6/es not_active Expired
- 1987-07-03 JP JP62166755A patent/JPS6322557A/ja active Pending
- 1987-07-03 SE SE8702753A patent/SE8702753L/xx not_active Application Discontinuation
- 1987-07-03 DD DD87304596A patent/DD263984A5/de not_active IP Right Cessation
- 1987-07-03 PT PT85256A patent/PT85256B/pt not_active IP Right Cessation
- 1987-07-03 DK DK343587A patent/DK343587A/da not_active Application Discontinuation
- 1987-07-03 AT AT0168087A patent/AT387382B/de not_active IP Right Cessation
- 1987-07-03 NO NO872796A patent/NO872796L/no unknown
- 1987-07-03 PL PL1987266620A patent/PL150350B1/pl unknown
- 1987-07-03 CN CN198787104582A patent/CN87104582A/zh active Pending
- 1987-07-03 IT IT21179/87A patent/IT1221952B/it active
- 1987-07-04 KR KR1019870007155A patent/KR880001589A/ko not_active Withdrawn
- 1987-07-06 DE DE19873722278 patent/DE3722278A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT8721179A0 (it) | 1987-07-03 |
| ATA168087A (de) | 1988-06-15 |
| KR880001589A (ko) | 1988-04-25 |
| DD263984A5 (de) | 1989-01-18 |
| AT387382B (de) | 1989-01-10 |
| PL150350B1 (en) | 1990-05-31 |
| FI872966A7 (fi) | 1988-01-05 |
| CS505187A2 (en) | 1988-08-16 |
| ES2004443A6 (es) | 1989-01-01 |
| GR871051B (en) | 1987-11-09 |
| PL266620A1 (en) | 1988-07-07 |
| NO872796L (no) | 1988-01-05 |
| PT85256A (en) | 1987-08-01 |
| HUT44491A (en) | 1988-03-28 |
| FI872966A0 (fi) | 1987-07-03 |
| CH672786A5 (enrdf_load_stackoverflow) | 1989-12-29 |
| NO872796D0 (no) | 1987-07-03 |
| CN87104582A (zh) | 1988-01-20 |
| SE8702753D0 (sv) | 1987-07-03 |
| YU118087A (en) | 1988-06-30 |
| DK343587A (da) | 1988-01-05 |
| PT85256B (pt) | 1990-03-30 |
| DK343587D0 (da) | 1987-07-03 |
| DE3722278A1 (de) | 1988-01-07 |
| SE8702753L (sv) | 1988-01-05 |
| JPS6322557A (ja) | 1988-01-30 |
| CS262693B2 (en) | 1989-03-14 |
| IT1221952B (it) | 1990-08-31 |
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