NO810638L - Fremgangsmaate til fremstilling av 5-cyano(3,4`-bipyridin)-6(1h)-on - Google Patents
Fremgangsmaate til fremstilling av 5-cyano(3,4`-bipyridin)-6(1h)-onInfo
- Publication number
- NO810638L NO810638L NO810638A NO810638A NO810638L NO 810638 L NO810638 L NO 810638L NO 810638 A NO810638 A NO 810638A NO 810638 A NO810638 A NO 810638A NO 810638 L NO810638 L NO 810638L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- cyano
- salt
- approx
- inorganic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- SEQOYYYZFNJQSV-UHFFFAOYSA-N 2-oxo-5-pyridin-4-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=NC=C1 SEQOYYYZFNJQSV-UHFFFAOYSA-N 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 28
- 125000002091 cationic group Chemical group 0.000 claims description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- -1 inorganic acid halide Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000022244 formylation Effects 0.000 description 3
- 238000006170 formylation reaction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- PNAHPHGJXNKLNF-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-4-ylprop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=NC=C1 PNAHPHGJXNKLNF-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 235000005152 nicotinamide Nutrition 0.000 description 2
- 150000005480 nicotinamides Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000011345 viscous material Substances 0.000 description 2
- YDQIHMPBIKSISO-UHFFFAOYSA-N 1h-pyridin-2-one;5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound O=C1C=CC=CN1.N#CC1=CN=CC(C=2C=CN=CC=2)=C1 YDQIHMPBIKSISO-UHFFFAOYSA-N 0.000 description 1
- UAOTWASOGSHQAI-UHFFFAOYSA-N 2-methoxy-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound C1=C(C#N)C(OC)=NC=C1C1=CC=NC=C1 UAOTWASOGSHQAI-UHFFFAOYSA-N 0.000 description 1
- NTHQYHTZRJMPFI-UHFFFAOYSA-N 2-oxo-5-pyridin-2-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=CC=N1 NTHQYHTZRJMPFI-UHFFFAOYSA-N 0.000 description 1
- AKKQMYMAJMINPN-UHFFFAOYSA-N 2-oxo-5-pyridin-2-yl-1h-pyridine-3-carboxamide Chemical class N1C(=O)C(C(=O)N)=CC(C=2N=CC=CC=2)=C1 AKKQMYMAJMINPN-UHFFFAOYSA-N 0.000 description 1
- ZQMMLUFYTCOQTB-UHFFFAOYSA-N 2-pyridin-2-ylpropanedial Chemical compound O=CC(C=O)C1=CC=CC=N1 ZQMMLUFYTCOQTB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229960002105 amrinone Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007975 iminium salts Chemical class 0.000 description 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OWVFJYJLBSWYII-UHFFFAOYSA-N n,n-dimethyl-2-pyridin-4-ylethenamine Chemical compound CN(C)C=CC1=CC=NC=C1 OWVFJYJLBSWYII-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- 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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/124,807 US4310670A (en) | 1980-02-26 | 1980-02-26 | Low-temperature, aqueous conversion of 4-picoline derivative to 5-cyano-[3,4'-bipyridin]-6(1H)-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO810638L true NO810638L (no) | 1981-08-27 |
Family
ID=22416874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810638A NO810638L (no) | 1980-02-26 | 1981-02-25 | Fremgangsmaate til fremstilling av 5-cyano(3,4`-bipyridin)-6(1h)-on |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4310670A (fr) |
| JP (1) | JPS56150065A (fr) |
| KR (1) | KR830005142A (fr) |
| AT (1) | AT375068B (fr) |
| AU (1) | AU6748881A (fr) |
| BE (1) | BE887662A (fr) |
| CA (1) | CA1128518A (fr) |
| DE (1) | DE3107280A1 (fr) |
| DK (1) | DK83881A (fr) |
| ES (1) | ES8202331A1 (fr) |
| FI (1) | FI810583L (fr) |
| FR (1) | FR2476648A1 (fr) |
| GB (1) | GB2070008B (fr) |
| IL (1) | IL62159A (fr) |
| IT (1) | IT1169216B (fr) |
| LU (1) | LU83170A1 (fr) |
| NL (1) | NL8100923A (fr) |
| NO (1) | NO810638L (fr) |
| NZ (1) | NZ196281A (fr) |
| PH (1) | PH15837A (fr) |
| PT (1) | PT72572B (fr) |
| SE (1) | SE431748B (fr) |
| ZA (1) | ZA811123B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO163008C (no) * | 1982-05-24 | 1990-03-21 | Sterling Drug Inc | 2-(laverealkoksy)-1-(pyridinyl)etenyl-lavere-alkylketon og fremgangsmaate for fremstilling av pyridinylnikotinderivater. |
| DE3842062A1 (de) * | 1988-12-14 | 1990-06-28 | Hoechst Ag | Explosionssichere 1-dimethylamino-3-dimethylimino-2-arylpropen-1-salze, verfahren zu ihrer herstellung und ihre verwendung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4072746A (en) * | 1975-10-14 | 1978-02-07 | Sterling Drug Inc. | 3-Amino-5-(pyridinyl)-2(1H)-pyridinones |
| US4004012A (en) * | 1975-10-14 | 1977-01-18 | Sterling Drug Inc. | 3-Cyano-5-(pyridinyl)-2(1H)-pyridinones |
-
1980
- 1980-02-26 US US06/124,807 patent/US4310670A/en not_active Expired - Lifetime
-
1981
- 1981-02-17 NZ NZ196281A patent/NZ196281A/xx unknown
- 1981-02-18 IL IL62159A patent/IL62159A/xx unknown
- 1981-02-20 GB GB8105368A patent/GB2070008B/en not_active Expired
- 1981-02-20 AU AU67488/81A patent/AU6748881A/en not_active Abandoned
- 1981-02-20 ZA ZA00811123A patent/ZA811123B/xx unknown
- 1981-02-24 SE SE8101204A patent/SE431748B/sv unknown
- 1981-02-24 PH PH25255A patent/PH15837A/en unknown
- 1981-02-24 FR FR8103608A patent/FR2476648A1/fr active Pending
- 1981-02-24 IT IT19951/81A patent/IT1169216B/it active
- 1981-02-25 AT AT0088481A patent/AT375068B/de not_active IP Right Cessation
- 1981-02-25 FI FI810583A patent/FI810583L/fi not_active Application Discontinuation
- 1981-02-25 DK DK83881A patent/DK83881A/da not_active Application Discontinuation
- 1981-02-25 PT PT72572A patent/PT72572B/pt unknown
- 1981-02-25 ES ES499775A patent/ES8202331A1/es not_active Expired
- 1981-02-25 CA CA371,706A patent/CA1128518A/fr not_active Expired
- 1981-02-25 BE BE1/10149A patent/BE887662A/fr not_active IP Right Cessation
- 1981-02-25 NL NL8100923A patent/NL8100923A/nl not_active Application Discontinuation
- 1981-02-25 NO NO810638A patent/NO810638L/no unknown
- 1981-02-26 LU LU83170A patent/LU83170A1/fr unknown
- 1981-02-26 JP JP2759881A patent/JPS56150065A/ja active Pending
- 1981-02-26 DE DE19813107280 patent/DE3107280A1/de not_active Withdrawn
- 1981-07-25 KR KR1019810000617A patent/KR830005142A/ko unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE8101204L (sv) | 1981-08-27 |
| IL62159A0 (en) | 1981-03-31 |
| ES499775A0 (es) | 1982-01-16 |
| GB2070008A (en) | 1981-09-03 |
| PT72572B (en) | 1982-03-19 |
| NL8100923A (nl) | 1981-09-16 |
| AU6748881A (en) | 1981-09-03 |
| FR2476648A1 (fr) | 1981-08-28 |
| DK83881A (da) | 1981-08-27 |
| LU83170A1 (fr) | 1981-09-11 |
| NZ196281A (en) | 1983-12-16 |
| PT72572A (en) | 1981-03-01 |
| GB2070008B (en) | 1984-04-18 |
| IL62159A (en) | 1984-06-29 |
| SE431748B (sv) | 1984-02-27 |
| CA1128518A (fr) | 1982-07-27 |
| ATA88481A (de) | 1983-11-15 |
| BE887662A (fr) | 1981-08-25 |
| DE3107280A1 (de) | 1982-01-07 |
| ES8202331A1 (es) | 1982-01-16 |
| FI810583L (fi) | 1981-08-27 |
| US4310670A (en) | 1982-01-12 |
| IT1169216B (it) | 1987-05-27 |
| ZA811123B (en) | 1982-03-31 |
| IT8119951A0 (it) | 1981-02-24 |
| JPS56150065A (en) | 1981-11-20 |
| PH15837A (en) | 1983-04-08 |
| KR830005142A (ko) | 1983-08-03 |
| AT375068B (de) | 1984-06-25 |
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