DE2537288A1 - Herstellung von trifluormethylsubstituierten aminobenzonitrilen - Google Patents
Herstellung von trifluormethylsubstituierten aminobenzonitrilenInfo
- Publication number
- DE2537288A1 DE2537288A1 DE19752537288 DE2537288A DE2537288A1 DE 2537288 A1 DE2537288 A1 DE 2537288A1 DE 19752537288 DE19752537288 DE 19752537288 DE 2537288 A DE2537288 A DE 2537288A DE 2537288 A1 DE2537288 A1 DE 2537288A1
- Authority
- DE
- Germany
- Prior art keywords
- trifluoromethyl
- substituted
- group
- ammonia
- aminobenzonitrile
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title description 7
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical class NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 title description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- -1 alkyl pyridines Chemical class 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VBPYHJRQZZCFCW-UHFFFAOYSA-N 4-chloro-3-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(C#N)=CC=C1Cl VBPYHJRQZZCFCW-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- GANPUEIPQFDYQA-UHFFFAOYSA-N 2-chloro-3-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C#N)=C1Cl GANPUEIPQFDYQA-UHFFFAOYSA-N 0.000 description 2
- LCISFYAQKHOWBP-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(Cl)C(C#N)=C1 LCISFYAQKHOWBP-UHFFFAOYSA-N 0.000 description 2
- NATCCVDNYHLFSP-UHFFFAOYSA-N 3,4-dibromo-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(C#N)=CC(Br)=C1Br NATCCVDNYHLFSP-UHFFFAOYSA-N 0.000 description 2
- HJTIGEGEIQXAGV-UHFFFAOYSA-N 3,4-dichloro-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(C#N)=CC(Cl)=C1Cl HJTIGEGEIQXAGV-UHFFFAOYSA-N 0.000 description 2
- MWLZJOBGDXBMBP-UHFFFAOYSA-N 4-amino-3-(trifluoromethyl)benzonitrile Chemical compound NC1=CC=C(C#N)C=C1C(F)(F)F MWLZJOBGDXBMBP-UHFFFAOYSA-N 0.000 description 2
- KSXUIQQDHHFSRN-UHFFFAOYSA-N 4-bromo-3-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(C#N)=CC=C1Br KSXUIQQDHHFSRN-UHFFFAOYSA-N 0.000 description 2
- TUWQECDDVRORJX-UHFFFAOYSA-N 4-chloro-3,5-bis(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(C#N)=CC(C(F)(F)F)=C1Cl TUWQECDDVRORJX-UHFFFAOYSA-N 0.000 description 2
- CQZQCORFYSSCFY-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzonitrile Chemical compound FC1=CC=C(C#N)C=C1C(F)(F)F CQZQCORFYSSCFY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QIQGUVQYKWGKPM-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(Cl)=C(Cl)C(C#N)=C1 QIQGUVQYKWGKPM-UHFFFAOYSA-N 0.000 description 1
- UHOSMRSMWHLHJO-UHFFFAOYSA-N 2-amino-3-(trifluoromethyl)benzonitrile Chemical compound NC1=C(C#N)C=CC=C1C(F)(F)F UHOSMRSMWHLHJO-UHFFFAOYSA-N 0.000 description 1
- ZLCIALUBLCAXPL-UHFFFAOYSA-N 2-amino-5-(trifluoromethyl)benzonitrile Chemical compound NC1=CC=C(C(F)(F)F)C=C1C#N ZLCIALUBLCAXPL-UHFFFAOYSA-N 0.000 description 1
- ICEINTPQBJRYDE-UHFFFAOYSA-N 2-bromo-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(Br)C(C#N)=C1 ICEINTPQBJRYDE-UHFFFAOYSA-N 0.000 description 1
- VQLZELVAXQLLQK-UHFFFAOYSA-N 2-chloro-3,5-bis(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(C#N)=C(Cl)C(C(F)(F)F)=C1 VQLZELVAXQLLQK-UHFFFAOYSA-N 0.000 description 1
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical class ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 1
- LCLVMSCLLULGRY-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)benzonitrile Chemical compound FC1=CC=C(C(F)(F)F)C=C1C#N LCLVMSCLLULGRY-UHFFFAOYSA-N 0.000 description 1
- LAOYKZXANJZURG-UHFFFAOYSA-N 4-amino-3,5-bis(trifluoromethyl)benzonitrile Chemical compound NC1=C(C(F)(F)F)C=C(C#N)C=C1C(F)(F)F LAOYKZXANJZURG-UHFFFAOYSA-N 0.000 description 1
- ZUWZYKRZBLJCJO-UHFFFAOYSA-N 4-amino-3-bromo-5-(trifluoromethyl)benzonitrile Chemical compound NC1=C(Br)C=C(C#N)C=C1C(F)(F)F ZUWZYKRZBLJCJO-UHFFFAOYSA-N 0.000 description 1
- YSBUJICJITXTSW-UHFFFAOYSA-N 4-amino-3-chloro-5-(trifluoromethyl)benzonitrile Chemical compound NC1=C(Cl)C=C(C#N)C=C1C(F)(F)F YSBUJICJITXTSW-UHFFFAOYSA-N 0.000 description 1
- OYQJGMPKFMIKHB-UHFFFAOYSA-N 4-amino-3-iodo-5-(trifluoromethyl)benzonitrile Chemical compound NC1=C(I)C=C(C#N)C=C1C(F)(F)F OYQJGMPKFMIKHB-UHFFFAOYSA-N 0.000 description 1
- GRNQHTXPUDZMGB-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1C#N GRNQHTXPUDZMGB-UHFFFAOYSA-N 0.000 description 1
- PWVWHORSCWVBKV-UHFFFAOYSA-N 4-chloro-3-(trifluoromethyl)benzoyl fluoride Chemical compound FC(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 PWVWHORSCWVBKV-UHFFFAOYSA-N 0.000 description 1
- WKKIELWEPGRLHF-UHFFFAOYSA-N 4-chloro-3-iodo-5-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(C#N)=CC(I)=C1Cl WKKIELWEPGRLHF-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- VCOYRKXQRUGBKS-UHFFFAOYSA-N N.[Cl] Chemical group N.[Cl] VCOYRKXQRUGBKS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- HPMLGNIUXVXALD-UHFFFAOYSA-N benzoyl fluoride Chemical compound FC(=O)C1=CC=CC=C1 HPMLGNIUXVXALD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752537288 DE2537288A1 (de) | 1975-08-21 | 1975-08-21 | Herstellung von trifluormethylsubstituierten aminobenzonitrilen |
| CH1053676A CH605688A5 (enrdf_load_stackoverflow) | 1975-08-21 | 1976-08-18 | |
| JP9826176A JPS5225741A (en) | 1975-08-21 | 1976-08-19 | Production of trifluoromethyl substituted aminobenzonitrile |
| GB3460776A GB1495375A (en) | 1975-08-21 | 1976-08-19 | Preparation of trifluoromethyl-substituted aminobenzonitriles |
| FR7625393A FR2321485A1 (fr) | 1975-08-21 | 1976-08-20 | Procede de production de trifluoromethyl-aminobenzonitriles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752537288 DE2537288A1 (de) | 1975-08-21 | 1975-08-21 | Herstellung von trifluormethylsubstituierten aminobenzonitrilen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2537288A1 true DE2537288A1 (de) | 1977-03-03 |
Family
ID=5954534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752537288 Withdrawn DE2537288A1 (de) | 1975-08-21 | 1975-08-21 | Herstellung von trifluormethylsubstituierten aminobenzonitrilen |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5225741A (enrdf_load_stackoverflow) |
| CH (1) | CH605688A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2537288A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2321485A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1495375A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053247A1 (de) * | 1980-11-28 | 1982-06-09 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 6-Fluor-anthranilsäurenitril oder 6-Fluor-anthranilsäure und 6-Fluor-anthranilsäurenitril |
| WO2002100339A3 (en) * | 2001-06-13 | 2003-10-16 | Biogal Gyogyszergyar | Novel process for preparing rac-bicalutamide and its intermediates |
| CN1301965C (zh) * | 2004-08-26 | 2007-02-28 | 大连绿源药业有限责任公司 | 2－三氟甲基－4－氰基苯胺的制备方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6239404Y2 (enrdf_load_stackoverflow) * | 1979-11-09 | 1987-10-07 | ||
| WO1997000845A1 (fr) * | 1995-06-20 | 1997-01-09 | Nippon Soda Co., Ltd. | Derives de 2,3-dihalogeno-6-trifluoromethylbenzene et procede de production |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB757361A (en) * | 1954-02-01 | 1956-09-19 | Ici Ltd | New monoazo dyestuffs of the benzene-azo-benzene series |
| US3375267A (en) * | 1965-01-21 | 1968-03-26 | Hooker Chemical Corp | Aminotetrafluorobenzonitrile |
| GB1075300A (en) * | 1965-06-14 | 1967-07-12 | Smith Kline French Lab | N-substituted-5-sulfamoyl-4-trifluoromethylanthranilic acids |
| US3549635A (en) * | 1968-07-01 | 1970-12-22 | Sandoz Ag | Preparation of substituted-2(1h)-quinazolinones |
| FR2079439A5 (enrdf_load_stackoverflow) * | 1970-02-02 | 1971-11-12 | Laskar Serge | |
| DE2448061A1 (de) * | 1974-10-09 | 1976-04-15 | Bayer Ag | Verfahren zur herstellung von 2-cyano-4-trifluormethyl-6-nitro-n,n-di-n-propyl-anilin |
-
1975
- 1975-08-21 DE DE19752537288 patent/DE2537288A1/de not_active Withdrawn
-
1976
- 1976-08-18 CH CH1053676A patent/CH605688A5/xx not_active IP Right Cessation
- 1976-08-19 JP JP9826176A patent/JPS5225741A/ja active Pending
- 1976-08-19 GB GB3460776A patent/GB1495375A/en not_active Expired
- 1976-08-20 FR FR7625393A patent/FR2321485A1/fr active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053247A1 (de) * | 1980-11-28 | 1982-06-09 | BASF Aktiengesellschaft | Verfahren zur Herstellung von 6-Fluor-anthranilsäurenitril oder 6-Fluor-anthranilsäure und 6-Fluor-anthranilsäurenitril |
| WO2002100339A3 (en) * | 2001-06-13 | 2003-10-16 | Biogal Gyogyszergyar | Novel process for preparing rac-bicalutamide and its intermediates |
| CN1301965C (zh) * | 2004-08-26 | 2007-02-28 | 大连绿源药业有限责任公司 | 2－三氟甲基－4－氰基苯胺的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH605688A5 (enrdf_load_stackoverflow) | 1978-10-13 |
| FR2321485B1 (enrdf_load_stackoverflow) | 1980-05-09 |
| FR2321485A1 (fr) | 1977-03-18 |
| JPS5225741A (en) | 1977-02-25 |
| GB1495375A (en) | 1977-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |