NO119588B - - Google Patents
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- Publication number
- NO119588B NO119588B NO159321A NO15932165A NO119588B NO 119588 B NO119588 B NO 119588B NO 159321 A NO159321 A NO 159321A NO 15932165 A NO15932165 A NO 15932165A NO 119588 B NO119588 B NO 119588B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- benzodiazepine
- dihydro
- acid
- chloro
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 3
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- -1 ketone radical Chemical class 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960005419 nitrogen Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 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
- 239000003208 petroleum Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38946964A | 1964-08-13 | 1964-08-13 | |
| US474159A US3391138A (en) | 1964-08-13 | 1965-07-22 | Certain 1-substituted-benzodiazepin-2-one compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO119588B true NO119588B (de) | 1970-06-08 |
Family
ID=27012718
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO159320A NO118914B (de) | 1964-08-13 | 1965-08-12 | |
| NO159321A NO119588B (de) | 1964-08-13 | 1965-08-12 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO159320A NO118914B (de) | 1964-08-13 | 1965-08-12 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3391138A (de) |
| BE (2) | BE668188A (de) |
| BR (2) | BR6571653D0 (de) |
| CH (1) | CH462831A (de) |
| DE (2) | DE1545952C3 (de) |
| DK (2) | DK120848B (de) |
| FR (1) | FR135F (de) |
| GB (2) | GB1102934A (de) |
| IL (2) | IL23999A (de) |
| NL (2) | NL6510538A (de) |
| NO (2) | NO118914B (de) |
| SE (2) | SE310687B (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2008612A1 (de) * | 1969-03-13 | 1970-10-01 | F. Hoffmann-La Roche & Co Ag, Basel (Schweiz) | Benzodiazepin-Derivate |
| US3989829A (en) * | 1969-04-18 | 1976-11-02 | Sumitomo Chemical Company, Limited | 1,4-Benzodiazepines |
| USRE28972E (en) * | 1969-07-10 | 1976-09-21 | Boehringer Ingelheim Gmbh | 5-Aryl-1H-1,5-benzodiazepine-2,4-diones |
| US3867372A (en) * | 1970-02-03 | 1975-02-18 | Sumitomo Chemical Co | Benzodiazepine process |
| US3691157A (en) * | 1970-08-12 | 1972-09-12 | Rodney Ian Fryer | Preparation of 7-substituted-1-(2-diethylaminoethyl)-5-(2-halophenyl)-1,3-dihydro-2h-1,4-benzodiazepin-2-ones |
| DE2166504B2 (de) * | 1970-08-31 | 1980-01-17 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | 1 -Alkoxyalkoxyalkyl^-halogen-Sphenyl-13-dihydro-2H-l,4-benzodiazepin-2-one und ihre Salze sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| AT314541B (de) * | 1970-10-19 | 1974-04-10 | Sumitomo Chemical Co | Verfahren zur Herstellung von neuen Benzodiazepinen und ihren Salzen |
| US4065451A (en) * | 1971-03-30 | 1977-12-27 | American Home Products | 1,3-Dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetate esters and their acid salts |
| US3886276A (en) * | 1971-03-30 | 1975-05-27 | American Home Prod | 1,3-Dihydro-3 -hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetate esters and their acid salts in compositions and methods for inducing a calming effect |
| US3872089A (en) * | 1971-05-14 | 1975-03-18 | Hoffmann La Roche | Substituted thienodiazepines |
| US3966943A (en) * | 1971-09-13 | 1976-06-29 | The Upjohn Company | 6-Pyridyl benzodiazepines antidepressants |
| US3926952A (en) * | 1972-10-03 | 1975-12-16 | American Home Prod | 1,4-Benzodiazepin-2-ones and their synthesis |
| US4012413A (en) * | 1973-05-17 | 1977-03-15 | The Upjohn Company | Organic compounds and process |
| US3865815A (en) * | 1973-11-29 | 1975-02-11 | Hoffmann La Roche | 7-Hydroxyamino-1,4-benzodiazepines |
| US4006135A (en) * | 1974-06-19 | 1977-02-01 | Ddsa Pharmaceuticals | Hydroxymethyl benzodiazepine derivatives |
| US3969504A (en) * | 1975-02-14 | 1976-07-13 | The Upjohn Co. | 6-Phenyl benzodiazepine antidepressants |
| DE2852606A1 (de) * | 1977-12-14 | 1979-06-21 | Gerot Pharmazeutika | 3-di-n-propyl-acetoxy-benzodiazepin-2-one und verfahren zu deren herstellung |
| AT361492B (de) * | 1978-12-18 | 1981-03-10 | Gerot Pharmazeutika | Verfahren zur herstellung von neuen 3-hydroxy- 1,4-benzodiazepin-2-onen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3236838A (en) * | 1964-06-09 | 1966-02-22 | Hoffmann La Roche | Certain 1-substituted-benzodiazepin-2-one compounds |
-
0
- FR FR135D patent/FR135F/fr active Active
-
1965
- 1965-07-21 IL IL23999A patent/IL23999A/en unknown
- 1965-07-21 IL IL23998A patent/IL23998A/xx unknown
- 1965-07-22 US US474159A patent/US3391138A/en not_active Expired - Lifetime
- 1965-07-23 CH CH1036865A patent/CH462831A/de unknown
- 1965-07-27 DE DE1545952A patent/DE1545952C3/de not_active Expired
- 1965-07-29 BR BR171653/65A patent/BR6571653D0/pt unknown
- 1965-07-29 BR BR171654/65A patent/BR6571654D0/pt unknown
- 1965-07-29 DE DE19651545953 patent/DE1545953A1/de active Pending
- 1965-08-09 GB GB33994/65A patent/GB1102934A/en not_active Expired
- 1965-08-09 GB GB44504/67A patent/GB1106040A/en not_active Expired
- 1965-08-11 DK DK411265AA patent/DK120848B/da unknown
- 1965-08-11 DK DK411365AA patent/DK125554B/da unknown
- 1965-08-12 NL NL6510538A patent/NL6510538A/xx unknown
- 1965-08-12 NL NL6510539A patent/NL6510539A/xx unknown
- 1965-08-12 BE BE668188D patent/BE668188A/xx unknown
- 1965-08-12 BE BE668189D patent/BE668189A/xx unknown
- 1965-08-12 NO NO159320A patent/NO118914B/no unknown
- 1965-08-12 NO NO159321A patent/NO119588B/no unknown
- 1965-08-13 SE SE10628/65A patent/SE310687B/xx unknown
- 1965-08-13 SE SE10629/65A patent/SE312558B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6510538A (de) | 1966-02-14 |
| DK120848B (da) | 1971-07-26 |
| US3391138A (en) | 1968-07-02 |
| DE1545952B2 (de) | 1974-07-04 |
| BE668188A (de) | 1966-02-14 |
| GB1106040A (en) | 1968-03-13 |
| DE1545953A1 (de) | 1969-11-20 |
| BE668189A (de) | 1965-12-01 |
| BR6571653D0 (pt) | 1973-08-14 |
| IL23999A (en) | 1969-05-28 |
| NO118914B (de) | 1970-03-02 |
| DE1545952C3 (de) | 1975-03-06 |
| IL23998A (en) | 1969-02-27 |
| SE310687B (de) | 1969-05-12 |
| DK125554B (da) | 1973-03-05 |
| CH462831A (de) | 1968-09-30 |
| FR135F (de) | |
| DE1545952A1 (de) | 1969-12-18 |
| BR6571654D0 (pt) | 1973-08-14 |
| SE312558B (de) | 1969-07-21 |
| GB1102934A (en) | 1968-02-14 |
| NL6510539A (de) | 1966-02-14 |
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