NO132800B - - Google Patents
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- Publication number
- NO132800B NO132800B NO1151/73A NO115171A NO132800B NO 132800 B NO132800 B NO 132800B NO 1151/73 A NO1151/73 A NO 1151/73A NO 115171 A NO115171 A NO 115171A NO 132800 B NO132800 B NO 132800B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- compound
- reaction
- volume
- solvent
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 4
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000006476 reductive cyclization reaction Methods 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 230000002829 reductive effect Effects 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- OUPDZXREZCZTCA-UHFFFAOYSA-N 7-chloro-2-ethoxy-5-phenyl-3h-1,4-benzodiazepine Chemical compound N=1CC(OCC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 OUPDZXREZCZTCA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- -1 acetic acid Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- CSSDVHWBCPHDBJ-UHFFFAOYSA-N ethyl 2-azido-n-(2-benzoyl-4-nitrophenyl)ethanimidate Chemical compound [N-]=[N+]=NCC(OCC)=NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 CSSDVHWBCPHDBJ-UHFFFAOYSA-N 0.000 description 2
- YEKALOQQGUZECI-UHFFFAOYSA-N ethyl n-(2-benzoyl-4-chlorophenyl)-2-bromoethanimidate Chemical compound CCOC(CBr)=NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 YEKALOQQGUZECI-UHFFFAOYSA-N 0.000 description 2
- AIUKYLGCVRVLRS-UHFFFAOYSA-N ethyl n-(2-benzoyl-4-nitrophenyl)-2-bromoethanimidate Chemical compound CCOC(CBr)=NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 AIUKYLGCVRVLRS-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NRIUXRXDBVAPGT-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC(Cl)=CC=C1N NRIUXRXDBVAPGT-UHFFFAOYSA-N 0.000 description 1
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
- PZPZDEIASIKHPY-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-phenylmethanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PZPZDEIASIKHPY-UHFFFAOYSA-N 0.000 description 1
- GNWZFNSUAXDUEQ-UHFFFAOYSA-N 2-ethoxy-7-nitro-5-phenyl-3h-1,4-benzodiazepine Chemical compound N=1CC(OCC)=NC2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GNWZFNSUAXDUEQ-UHFFFAOYSA-N 0.000 description 1
- PVCXBJUOIGBRLH-UHFFFAOYSA-N 7-chloro-2-ethoxy-5-(4-methoxyphenyl)-3h-1,4-benzodiazepine Chemical compound N=1CC(OCC)=NC2=CC=C(Cl)C=C2C=1C1=CC=C(OC)C=C1 PVCXBJUOIGBRLH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- SUUQFZBBDDLXAJ-UHFFFAOYSA-N ethyl 2-azido-N-[4-chloro-2-(4-methoxybenzoyl)phenyl]ethanimidate Chemical compound [N-]=[N+]=NCC(OCC)=NC1=CC=C(Cl)C=C1C(=O)C1=CC=C(OC)C=C1 SUUQFZBBDDLXAJ-UHFFFAOYSA-N 0.000 description 1
- QPIVNKFAQXSDRQ-UHFFFAOYSA-N ethyl 2-azido-n-(2-benzoyl-4-chlorophenyl)ethanimidate Chemical compound [N-]=[N+]=NCC(OCC)=NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 QPIVNKFAQXSDRQ-UHFFFAOYSA-N 0.000 description 1
- HXYZKZNHHDFXNG-UHFFFAOYSA-N ethyl 2-bromo-n-[4-chloro-2-(4-methoxybenzoyl)phenyl]ethanimidate Chemical compound CCOC(CBr)=NC1=CC=C(Cl)C=C1C(=O)C1=CC=C(OC)C=C1 HXYZKZNHHDFXNG-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/20—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO752039A NO138849C (no) | 1970-03-27 | 1975-06-09 | Fremgangsmaate til fremstilling av 2-alkoksy-1,4-benzodiazepinderivater |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2580470A JPS4811112B1 (ru) | 1970-03-27 | 1970-03-27 | |
| JP2580570A JPS5010316B1 (ru) | 1970-03-27 | 1970-03-27 | |
| JP3495070A JPS5011920B1 (ru) | 1970-04-23 | 1970-04-23 | |
| JP4663770A JPS4924060B1 (ru) | 1970-05-28 | 1970-05-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO132800B true NO132800B (ru) | 1975-09-29 |
| NO132800C NO132800C (ru) | 1976-01-07 |
Family
ID=27458380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1151/71A NO132800C (ru) | 1970-03-27 | 1971-03-26 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4102881A (ru) |
| BE (1) | BE764913A (ru) |
| CA (2) | CA922317A (ru) |
| CH (1) | CH559188A5 (ru) |
| DE (1) | DE2114441A1 (ru) |
| DK (1) | DK131374B (ru) |
| FI (1) | FI55334C (ru) |
| FR (1) | FR2085748B1 (ru) |
| GB (1) | GB1353486A (ru) |
| NL (1) | NL7104132A (ru) |
| NO (1) | NO132800C (ru) |
| PH (1) | PH9214A (ru) |
| SE (1) | SE400968B (ru) |
| YU (1) | YU34997B (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709898A (en) * | 1971-02-09 | 1973-01-09 | Upjohn Co | Process for the production of triazolobenzodiazepines and intermediates |
| US3681343A (en) * | 1971-05-11 | 1972-08-01 | Upjohn Co | 6-phenyl-s-triazolo{8 4,3-a{9 {8 1,4{9 {0 benzodiazepines |
| US4755508A (en) * | 1984-06-26 | 1988-07-05 | Merck & Co., Inc. | Benzodiazepine analogs and use as antogonists of gastrin and cholecystokinin |
| US5939414A (en) * | 1996-10-31 | 1999-08-17 | Merck & Co., Inc. | Benzodiazepine hydrazide derivatives as inhibitors of HIV integrase |
| WO1998018473A1 (en) * | 1996-10-31 | 1998-05-07 | Merck & Co., Inc. | Benzodiazepine hydrazide derivatives as inhibitors of hiv integrase |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462418A (en) * | 1963-10-29 | 1969-08-19 | Hoffmann La Roche | Preparation of 1,4-benzodiazepin-2-one-4-oxide from 2-lower alkoxy-1,4-benzodiazepine-4-oxide |
| DK120901B (da) * | 1965-09-17 | 1971-08-02 | Rexolin Chem | Fremgangsmåde til fremstilling af 7-chlor-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-on. |
| US3987052A (en) * | 1969-03-17 | 1976-10-19 | The Upjohn Company | 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
| ZA705076B (en) * | 1969-07-30 | 1971-04-28 | Grindstedvaerket As | New 1,4-benzodiazepines |
| BE755139A (fr) * | 1969-08-21 | 1971-02-22 | Upjohn Co | Derives de benzodiazepinones, leurs intermediaires, et leur preparatio |
| FR2022598A1 (en) * | 1969-11-04 | 1970-07-31 | Pakeda Chemical Ind | Sedative chloro-phenyl-triazolobenzodiazepines |
-
1971
- 1971-03-24 YU YU737/71A patent/YU34997B/xx unknown
- 1971-03-25 CH CH437571A patent/CH559188A5/xx not_active IP Right Cessation
- 1971-03-25 FR FR7110689A patent/FR2085748B1/fr not_active Expired
- 1971-03-25 DE DE19712114441 patent/DE2114441A1/de not_active Withdrawn
- 1971-03-26 PH PH12320*UA patent/PH9214A/en unknown
- 1971-03-26 BE BE764913A patent/BE764913A/xx unknown
- 1971-03-26 NO NO1151/71A patent/NO132800C/no unknown
- 1971-03-26 SE SE7103998A patent/SE400968B/xx unknown
- 1971-03-26 DK DK147671AA patent/DK131374B/da unknown
- 1971-03-26 CA CA108803A patent/CA922317A/en not_active Expired
- 1971-03-26 NL NL7104132A patent/NL7104132A/xx unknown
- 1971-03-29 FI FI896/71A patent/FI55334C/fi active
- 1971-04-19 GB GB2562271*A patent/GB1353486A/en not_active Expired
-
1972
- 1972-11-16 CA CA156599A patent/CA936864A/en not_active Expired
-
1974
- 1974-06-12 US US05/478,823 patent/US4102881A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| YU34997B (en) | 1980-06-30 |
| DE2114441A1 (de) | 1971-10-14 |
| GB1353486A (en) | 1974-05-15 |
| PH9214A (en) | 1975-07-10 |
| US4102881A (en) | 1978-07-25 |
| DK131374C (ru) | 1975-12-01 |
| CA922317A (en) | 1973-03-06 |
| YU73771A (en) | 1979-12-31 |
| FI55334C (fi) | 1979-07-10 |
| NL7104132A (ru) | 1971-09-29 |
| FR2085748B1 (ru) | 1974-08-02 |
| FI55334B (fi) | 1979-03-30 |
| FR2085748A1 (ru) | 1971-12-31 |
| CA936864A (en) | 1973-11-13 |
| BE764913A (fr) | 1971-08-16 |
| DK131374B (da) | 1975-07-07 |
| SE400968B (sv) | 1978-04-17 |
| CH559188A5 (ru) | 1975-02-28 |
| NO132800C (ru) | 1976-01-07 |
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