DE2119260A1 - Neue Phthalimidverbindungen und Verfahren zu ihrer Herstellung - Google Patents
Neue Phthalimidverbindungen und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2119260A1 DE2119260A1 DE19712119260 DE2119260A DE2119260A1 DE 2119260 A1 DE2119260 A1 DE 2119260A1 DE 19712119260 DE19712119260 DE 19712119260 DE 2119260 A DE2119260 A DE 2119260A DE 2119260 A1 DE2119260 A1 DE 2119260A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- acid
- ethyl
- chlorine
- isopropyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 43
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 238000005804 alkylation reaction Methods 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 9
- 238000005886 esterification reaction Methods 0.000 claims description 9
- 150000004702 methyl esters Chemical class 0.000 claims description 9
- 230000029936 alkylation Effects 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 6
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000026030 halogenation Effects 0.000 claims description 5
- 238000005658 halogenation reaction Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- JOSOUQLGXHXQDR-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1N1C(=O)C2=CC=CC=C2C1=O JOSOUQLGXHXQDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000005580 one pot reaction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000013078 crystal Substances 0.000 description 12
- -1 alkyl toluenesulfonate Chemical compound 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000538 analytical sample Substances 0.000 description 8
- 150000002148 esters Chemical group 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 229940054066 benzamide antipsychotics Drugs 0.000 description 7
- 150000003936 benzamides Chemical class 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- BEZQTEBPMMEPNB-UHFFFAOYSA-N ethyl 4-amino-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(N)C=C1O BEZQTEBPMMEPNB-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 201000003152 motion sickness Diseases 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- QQOXBFUTRLDXDP-UHFFFAOYSA-N p-Aminosalicylic acid methyl ester Chemical compound COC(=O)C1=CC=C(N)C=C1O QQOXBFUTRLDXDP-UHFFFAOYSA-N 0.000 description 2
- 125000005544 phthalimido group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- YBUHABZMSNVUKQ-UHFFFAOYSA-N propan-2-yl 4-amino-2-hydroxybenzoate Chemical compound CC(C)OC(=O)C1=CC=C(N)C=C1O YBUHABZMSNVUKQ-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RQTVIKMRXYJTDX-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-phenylpiperidine-4-carbonitrile Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC(C=2C=CC=CC=2)(C#N)CC1 RQTVIKMRXYJTDX-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 208000037175 Travel-Related Illness Diseases 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- LVFRSNCBCHABAM-UHFFFAOYSA-N ethyl 3-chlorobenzoate Chemical compound CCOC(=O)C1=CC=CC(Cl)=C1 LVFRSNCBCHABAM-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- JAVRNIFMYIJXIE-UHFFFAOYSA-N methyl 2-chlorobenzoate Chemical compound COC(=O)C1=CC=CC=C1Cl JAVRNIFMYIJXIE-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Spinning Or Twisting Of Yarns (AREA)
- Clamps And Clips (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US458770A | 1970-01-21 | 1970-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2119260A1 true DE2119260A1 (de) | 1972-03-30 |
Family
ID=21711507
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712119260 Pending DE2119260A1 (de) | 1970-01-21 | 1971-01-21 | Neue Phthalimidverbindungen und Verfahren zu ihrer Herstellung |
| DE2102848A Expired DE2102848C3 (de) | 1970-01-21 | 1971-01-21 | Verfahren zur Herstellung von N-(Diäthylaminoäthyl)-benzamiden |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2102848A Expired DE2102848C3 (de) | 1970-01-21 | 1971-01-21 | Verfahren zur Herstellung von N-(Diäthylaminoäthyl)-benzamiden |
Country Status (15)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0825970B2 (ja) * | 1987-09-01 | 1996-03-13 | 住友化学工業株式会社 | テトラヒドロフタルイミド系化合物の製造法、その中間体および該中間体の製造法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1233877B (de) * | 1961-07-25 | 1967-02-09 | Ile De France | Verfahren zur Herstellung von substituierten N-(tert. Aminoalkyl)-benzamiden |
| FR1407055A (fr) * | 1963-03-05 | 1965-07-30 | Ile De France | Nouveau procédé de préparation de benzamides substitués |
| FR1476925A (fr) * | 1965-04-08 | 1967-04-14 | Ile De France | Nouveau procédé de préparation de nu-tertiaire-aminoalkyl-2-hydroxy (ou alcoxy) 4-amino-5-halogéno benzamides |
-
1970
- 1970-05-14 JP JP45041549A patent/JPS5024B1/ja active Pending
-
1971
- 1971-01-18 GB GB4814872A patent/GB1346792A/en not_active Expired
- 1971-01-18 GB GB224071A patent/GB1346791A/en not_active Expired
- 1971-01-19 BR BR000323/71A patent/BR7100323D0/pt unknown
- 1971-01-20 FR FR717101809A patent/FR2077252B1/fr not_active Expired
- 1971-01-20 FI FI146/71A patent/FI57098C/fi active
- 1971-01-20 AT AT724072A patent/AT322539B/de not_active IP Right Cessation
- 1971-01-20 AT AT45271*#A patent/AT335425B/de not_active IP Right Cessation
- 1971-01-20 SE SE7100631A patent/SE400776B/xx unknown
- 1971-01-20 BE BE761820A patent/BE761820A/xx unknown
- 1971-01-20 NO NO196/71A patent/NO132536C/no unknown
- 1971-01-21 ES ES387498A patent/ES387498A1/es not_active Expired
- 1971-01-21 DE DE19712119260 patent/DE2119260A1/de active Pending
- 1971-01-21 ZA ZA710389A patent/ZA71389B/xx unknown
- 1971-01-21 DE DE2102848A patent/DE2102848C3/de not_active Expired
- 1971-01-21 DK DK25271AA patent/DK136032B/da unknown
- 1971-01-21 CH CH89671A patent/CH544086A/fr not_active IP Right Cessation
- 1971-01-21 NL NL7100795A patent/NL7100795A/xx not_active Application Discontinuation
- 1971-10-05 JP JP46078263A patent/JPS507593B1/ja active Pending
-
1973
- 1973-08-30 SE SE7311784A patent/SE400553B/xx unknown
- 1973-08-30 SE SE7311783A patent/SE402911C/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE402911B (sv) | 1978-07-24 |
| ZA71389B (en) | 1971-10-27 |
| DE2102848A1 (de) | 1971-10-21 |
| BE761820A (fr) | 1971-07-01 |
| DE2102848C3 (de) | 1983-03-10 |
| BR7100323D0 (pt) | 1973-07-19 |
| FR2077252A1 (enrdf_load_stackoverflow) | 1971-10-22 |
| DE2102848B2 (de) | 1975-11-06 |
| NL7100795A (enrdf_load_stackoverflow) | 1971-07-23 |
| FI57098B (fi) | 1980-02-29 |
| SE400553B (sv) | 1978-04-03 |
| SE400776B (sv) | 1978-04-10 |
| CH544086A (fr) | 1973-11-15 |
| DK136032B (da) | 1977-08-01 |
| GB1346791A (en) | 1974-02-13 |
| NO132536B (enrdf_load_stackoverflow) | 1975-08-18 |
| NO132536C (enrdf_load_stackoverflow) | 1975-11-26 |
| JPS507593B1 (enrdf_load_stackoverflow) | 1975-03-27 |
| FI57098C (fi) | 1980-06-10 |
| FR2077252B1 (enrdf_load_stackoverflow) | 1973-06-08 |
| ES387498A1 (es) | 1974-01-16 |
| JPS5024B1 (enrdf_load_stackoverflow) | 1975-01-06 |
| DK136032C (enrdf_load_stackoverflow) | 1981-09-14 |
| GB1346792A (en) | 1974-02-13 |
| AT335425B (de) | 1977-03-10 |
| AT322539B (de) | 1975-05-26 |
| SE402911C (sv) | 1984-03-19 |
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