DD203718A5 - Verfahren zur herstellung von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxylsalzen bzw. den ensprechenden carboxysaeuren - Google Patents
Verfahren zur herstellung von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxylsalzen bzw. den ensprechenden carboxysaeuren Download PDFInfo
- Publication number
- DD203718A5 DD203718A5 DD81244216A DD24421681A DD203718A5 DD 203718 A5 DD203718 A5 DD 203718A5 DD 81244216 A DD81244216 A DD 81244216A DD 24421681 A DD24421681 A DD 24421681A DD 203718 A5 DD203718 A5 DD 203718A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- aryl
- lower alkyl
- preparation
- substituted
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- -1 thiolate salts Chemical class 0.000 claims abstract description 46
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000003138 primary alcohols Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 13
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000007944 thiolates Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- TUZFIWBNGKNFPW-UHFFFAOYSA-M sodium;2-methylpropane-2-thiolate Chemical compound [Na+].CC(C)(C)[S-] TUZFIWBNGKNFPW-UHFFFAOYSA-M 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BKPXEDRKBBTGAQ-UHFFFAOYSA-N 4-(2,6-dimethylanilino)oxolan-2-one Chemical compound CC1=CC=CC(C)=C1NC1CC(=O)OC1 BKPXEDRKBBTGAQ-UHFFFAOYSA-N 0.000 description 1
- JLPLJLLOCNCVTA-UHFFFAOYSA-N 4-bromooxolan-2-one Chemical compound BrC1COC(=O)C1 JLPLJLLOCNCVTA-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- PPQJYSFHPKMDDM-UHFFFAOYSA-N 4-tert-butylsulfanyl-2-(2,3,6-trimethylanilino)butanoic acid Chemical compound C(=O)(O)C(CCSC(C)(C)C)NC1=C(C(=CC=C1C)C)C PPQJYSFHPKMDDM-UHFFFAOYSA-N 0.000 description 1
- YWLUWLQYBLKWCF-UHFFFAOYSA-N 4-tert-butylsulfanyl-2-(2-methoxy-6-methylanilino)butanoic acid Chemical compound C(=O)(O)C(CCSC(C)(C)C)NC1=C(C=CC=C1C)OC YWLUWLQYBLKWCF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OAEZDDAJJCXHAL-UHFFFAOYSA-N C(=O)(O)C1(CC=CC2=CC=CC=C12)NCCCSC(C)(C)C Chemical compound C(=O)(O)C1(CC=CC2=CC=CC=C12)NCCCSC(C)(C)C OAEZDDAJJCXHAL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- GDAMWPQNFIQQAB-UHFFFAOYSA-M potassium;2-methylpropane-2-thiolate Chemical compound [K+].CC(C)(C)[S-] GDAMWPQNFIQQAB-UHFFFAOYSA-M 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16245380A | 1980-06-23 | 1980-06-23 | |
| US06/184,846 US4311849A (en) | 1980-09-08 | 1980-09-08 | Process for making 3-(N-arylamino)-gamma-butyrothiolactones |
| US20086480A | 1980-10-27 | 1980-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD203718A5 true DD203718A5 (de) | 1983-11-02 |
Family
ID=27388753
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81244216A DD203718A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxylsalzen bzw. den ensprechenden carboxysaeuren |
| DD81244217A DD209443A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von acylaminoderivaten von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxysaeuren |
| DD81231058A DD160416A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von 3-(n-aryl-n-acylamio)-gamma-butyrothiolactonen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81244217A DD209443A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von acylaminoderivaten von 1-(aryl- oder subst.-aryl)amino-1-thioalkancarboxysaeuren |
| DD81231058A DD160416A5 (de) | 1980-06-23 | 1981-06-23 | Verfahren zur herstellung von 3-(n-aryl-n-acylamio)-gamma-butyrothiolactonen |
Country Status (8)
| Country | Link |
|---|---|
| CH (1) | CH648307A5 (fr) |
| DD (3) | DD203718A5 (fr) |
| DE (1) | DE3123864A1 (fr) |
| ES (3) | ES503313A0 (fr) |
| FR (3) | FR2485013A1 (fr) |
| GB (1) | GB2078741B (fr) |
| IT (1) | IT1136849B (fr) |
| NL (1) | NL8103024A (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5175310A (en) * | 1990-03-16 | 1992-12-29 | Elf Atochem North America, Inc. | Process for producing alkylthio- and arylthio-substituted carboxylic acids and their thioesters |
| CN1035252C (zh) * | 1993-11-23 | 1997-06-25 | 王桂英 | 氨甲基甲酸-1，1，1-三氯-2-(2,4－二氯硫酚基) 乙基酯及其制备方法 |
| ES2088817B1 (es) * | 1993-12-02 | 1997-08-01 | Univ La Laguna | Control de nematodos fitoparasitos con lignanos tipo dibencil-butirolactonas. |
| CN114891221B (zh) * | 2019-10-14 | 2023-09-15 | 中国科学院上海有机化学研究所 | 聚（γ-硫代丁内酯） |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2408601A1 (fr) * | 1977-11-01 | 1979-06-08 | Chevron Res | Procede d'acylation d'une aniline substituee par une lactone en l'absence d'accepteur d'acide |
| BR8000986A (pt) * | 1979-02-22 | 1980-10-29 | Chevron Res | Composto fungicida, processo para controlar o crescimento de fungos, composicao fungicidas e processo para o controle de fungos |
| MA19111A1 (fr) * | 1979-10-26 | 1981-12-31 | Ciba Geigy Ag | Derives de l'homoserine,procede pour leur preparation et leur utilisation en tant que microbicides |
-
1981
- 1981-06-16 DE DE19813123864 patent/DE3123864A1/de not_active Withdrawn
- 1981-06-19 FR FR8112167A patent/FR2485013A1/fr active Granted
- 1981-06-22 IT IT22482/81A patent/IT1136849B/it active
- 1981-06-23 CH CH4154/81A patent/CH648307A5/de not_active IP Right Cessation
- 1981-06-23 NL NL8103024A patent/NL8103024A/nl not_active Application Discontinuation
- 1981-06-23 GB GB8119334A patent/GB2078741B/en not_active Expired
- 1981-06-23 ES ES503313A patent/ES503313A0/es active Granted
- 1981-06-23 DD DD81244216A patent/DD203718A5/de unknown
- 1981-06-23 DD DD81244217A patent/DD209443A5/de unknown
- 1981-06-23 DD DD81231058A patent/DD160416A5/de unknown
- 1981-11-17 FR FR8121478A patent/FR2491069B1/fr not_active Expired
- 1981-11-17 FR FR8121477A patent/FR2491062A1/fr active Granted
-
1982
- 1982-06-14 ES ES513071A patent/ES8304115A1/es not_active Expired
- 1982-06-14 ES ES513070A patent/ES8304114A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2491069B1 (fr) | 1983-12-16 |
| ES513070A0 (es) | 1983-02-16 |
| IT1136849B (it) | 1986-09-03 |
| ES8304114A1 (es) | 1983-02-16 |
| GB2078741A (en) | 1982-01-13 |
| ES8300105A1 (es) | 1982-10-01 |
| FR2491069A1 (fr) | 1982-04-02 |
| FR2491062B1 (fr) | 1985-01-18 |
| FR2485013B1 (fr) | 1984-06-29 |
| NL8103024A (nl) | 1982-01-18 |
| CH648307A5 (de) | 1985-03-15 |
| ES503313A0 (es) | 1982-10-01 |
| ES513071A0 (es) | 1983-02-16 |
| DD160416A5 (de) | 1983-07-27 |
| GB2078741B (en) | 1984-02-08 |
| FR2485013A1 (fr) | 1981-12-24 |
| ES8304115A1 (es) | 1983-02-16 |
| DD209443A5 (de) | 1984-05-09 |
| DE3123864A1 (de) | 1982-03-04 |
| IT8122482A0 (it) | 1981-06-22 |
| FR2491062A1 (fr) | 1982-04-02 |
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