CA1122986A - Process for producing pyridines substituted aromatically or heteroaromatically in the 3 position - Google Patents
Process for producing pyridines substituted aromatically or heteroaromatically in the 3 positionInfo
- Publication number
- CA1122986A CA1122986A CA326,706A CA326706A CA1122986A CA 1122986 A CA1122986 A CA 1122986A CA 326706 A CA326706 A CA 326706A CA 1122986 A CA1122986 A CA 1122986A
- Authority
- CA
- Canada
- Prior art keywords
- aldehyde
- general formula
- aliphatic
- temperature
- ammonia
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 15
- -1 aliphatic oxo compound Chemical class 0.000 claims abstract description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000007789 gas Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 7
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 14
- 150000003222 pyridines Chemical class 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 2
- 229920003023 plastic Polymers 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 239000011814 protection agent Substances 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 26
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 19
- 150000001299 aldehydes Chemical class 0.000 description 13
- HJKGBRPNSJADMB-UHFFFAOYSA-N 3-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1 HJKGBRPNSJADMB-UHFFFAOYSA-N 0.000 description 12
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229940100595 phenylacetaldehyde Drugs 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- UUCLVSDUMKMBSM-UHFFFAOYSA-N 3-benzylpyridine Chemical compound C=1C=CN=CC=1CC1=CC=CC=C1 UUCLVSDUMKMBSM-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 6
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- VJBXDBWLDQDBPG-UHFFFAOYSA-N 3-benzyl-4-methylpyridine Chemical compound CC1=CC=NC=C1CC1=CC=CC=C1 VJBXDBWLDQDBPG-UHFFFAOYSA-N 0.000 description 2
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 2
- 150000005361 3-phenylpyridines Chemical class 0.000 description 2
- YDJITZMUZXZCBI-UHFFFAOYSA-N 4-methyl-3-phenylpyridine Chemical compound CC1=CC=NC=C1C1=CC=CC=C1 YDJITZMUZXZCBI-UHFFFAOYSA-N 0.000 description 2
- MVTFMJPVPXNIFC-UHFFFAOYSA-N 4-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=CN=CC2=CC=CC=C12 MVTFMJPVPXNIFC-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- CWJCFOZDFPMHBR-UHFFFAOYSA-N lithium;3h-pyridin-3-ide Chemical compound [Li+].C1=C[C-]=CN=C1 CWJCFOZDFPMHBR-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- LABTWGUMFABVFG-ONEGZZNKSA-N (3E)-pent-3-en-2-one Chemical compound C\C=C\C(C)=O LABTWGUMFABVFG-ONEGZZNKSA-N 0.000 description 1
- JMTCQDNRTSGBGC-UHFFFAOYSA-N 2-(3-methylphenyl)pyridine Chemical compound CC1=CC=CC(C=2N=CC=CC=2)=C1 JMTCQDNRTSGBGC-UHFFFAOYSA-N 0.000 description 1
- JXNAIOCJWBJGFQ-UHFFFAOYSA-N 2-methyl-5-phenylpyridine Chemical compound C1=NC(C)=CC=C1C1=CC=CC=C1 JXNAIOCJWBJGFQ-UHFFFAOYSA-N 0.000 description 1
- JTGKLBDOZYMAEA-UHFFFAOYSA-N 2-thiophen-2-ylacetaldehyde Chemical compound O=CCC1=CC=CS1 JTGKLBDOZYMAEA-UHFFFAOYSA-N 0.000 description 1
- CKCMNYDVHYXJDG-UHFFFAOYSA-N 2-thiophen-3-ylacetaldehyde Chemical compound O=CCC=1C=CSC=1 CKCMNYDVHYXJDG-UHFFFAOYSA-N 0.000 description 1
- UCWQMPICSBZRLS-UHFFFAOYSA-N 3-benzyl-5-methylpyridine Chemical compound CC1=CN=CC(CC=2C=CC=CC=2)=C1 UCWQMPICSBZRLS-UHFFFAOYSA-N 0.000 description 1
- VPFKZMSXKPTQJG-UHFFFAOYSA-N 3-methyl-5-phenylpyridine Chemical compound CC1=CN=CC(C=2C=CC=CC=2)=C1 VPFKZMSXKPTQJG-UHFFFAOYSA-N 0.000 description 1
- AZAXFLWCDPQVHO-UHFFFAOYSA-N 3-thiophen-2-ylpropanal Chemical compound O=CCCC1=CC=CS1 AZAXFLWCDPQVHO-UHFFFAOYSA-N 0.000 description 1
- QDTQNHLHBKGUBF-UHFFFAOYSA-N 3-thiophen-3-ylpropanal Chemical compound O=CCCC=1C=CSC=1 QDTQNHLHBKGUBF-UHFFFAOYSA-N 0.000 description 1
- RXKHEBJUSZNIQI-UHFFFAOYSA-N 5-benzyl-2-methylpyridine Chemical compound C1=NC(C)=CC=C1CC1=CC=CC=C1 RXKHEBJUSZNIQI-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 150000001399 aluminium compounds Chemical class 0.000 description 1
- 229940077746 antacid containing aluminium compound Drugs 0.000 description 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-O azanium;hydrofluoride Chemical compound [NH4+].F LDDQLRUQCUTJBB-UHFFFAOYSA-O 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000009835 boiling Methods 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
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RYMBAPVTUHZCNF-UHFFFAOYSA-N phenyl(pyridin-3-yl)methanone Chemical compound C=1C=CN=CC=1C(=O)C1=CC=CC=C1 RYMBAPVTUHZCNF-UHFFFAOYSA-N 0.000 description 1
- KKWVSVIYNHRKPT-UHFFFAOYSA-N pyridine-3-carbonyl pyridine-3-carboperoxoate Chemical compound C=1C=CN=CC=1C(=O)OOC(=O)C1=CC=CN=C1 KKWVSVIYNHRKPT-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000005406 washing Methods 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
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/12—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from unsaturated compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782819196 DE2819196A1 (de) | 1978-05-02 | 1978-05-02 | Verfahren zur herstellung substituierter pyridine |
| DEP2819196.0 | 1978-05-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1122986A true CA1122986A (en) | 1982-05-04 |
Family
ID=6038491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA326,706A Expired CA1122986A (en) | 1978-05-02 | 1979-05-01 | Process for producing pyridines substituted aromatically or heteroaromatically in the 3 position |
Country Status (11)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3741159A1 (de) * | 1987-12-04 | 1989-06-15 | Basf Ag | Verfahren zur herstellung von cyano-pyridinen |
| US6492524B1 (en) * | 2001-03-27 | 2002-12-10 | Council Of Scientific And Industrial Research | Process for the synthesis of an aryl pyridine base using a zeolite catalyst |
| DE60143129D1 (de) * | 2001-03-30 | 2010-11-04 | Council Scient Ind Res | Verfahren zur herstellung von aryl-pyridinyl-derivaten unter verwendung von einem zeolith-katalysator |
| JP4119114B2 (ja) | 2001-11-28 | 2008-07-16 | 広栄化学工業株式会社 | 新規なジヒドロキシ（３−ピリジル）ボラン類 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2554946A1 (de) * | 1975-12-06 | 1977-06-23 | Degussa | Verfahren zur gewinnung von pyridin und 3-methylpyridin |
| DE2639701A1 (de) * | 1976-09-03 | 1978-03-09 | Degussa | Verfahren zur herstellung substituierter pyridine |
-
1978
- 1978-05-02 DE DE19782819196 patent/DE2819196A1/de active Granted
-
1979
- 1979-03-06 NL NL7901788A patent/NL7901788A/xx unknown
- 1979-03-28 FR FR7907835A patent/FR2424911A1/fr active Granted
- 1979-04-11 BR BR7902274A patent/BR7902274A/pt unknown
- 1979-04-13 IL IL57069A patent/IL57069A/xx unknown
- 1979-04-25 GB GB7914375A patent/GB2020270B/en not_active Expired
- 1979-04-26 BE BE0/194856A patent/BE875878A/xx not_active IP Right Cessation
- 1979-04-30 IT IT48890/79A patent/IT1162485B/it active
- 1979-05-01 JP JP54052562A patent/JPS5827789B2/ja not_active Expired
- 1979-05-01 CA CA326,706A patent/CA1122986A/en not_active Expired
- 1979-05-01 CH CH407479A patent/CH638786A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2424911B1 (enrdf_load_stackoverflow) | 1984-05-18 |
| CH638786A5 (de) | 1983-10-14 |
| GB2020270A (en) | 1979-11-14 |
| DE2819196C2 (enrdf_load_stackoverflow) | 1989-03-16 |
| BR7902274A (pt) | 1979-12-11 |
| NL7901788A (nl) | 1979-11-06 |
| BE875878A (fr) | 1979-10-26 |
| GB2020270B (en) | 1983-02-02 |
| IT7948890A0 (it) | 1979-04-30 |
| FR2424911A1 (fr) | 1979-11-30 |
| JPS54144379A (en) | 1979-11-10 |
| DE2819196A1 (de) | 1979-11-15 |
| JPS5827789B2 (ja) | 1983-06-11 |
| IL57069A (en) | 1982-08-31 |
| IT1162485B (it) | 1987-04-01 |
| IL57069A0 (en) | 1979-07-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |