NO126799B - - Google Patents
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- Publication number
- NO126799B NO126799B NO04310/70A NO431070A NO126799B NO 126799 B NO126799 B NO 126799B NO 04310/70 A NO04310/70 A NO 04310/70A NO 431070 A NO431070 A NO 431070A NO 126799 B NO126799 B NO 126799B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- benzodiazepine
- chloro
- phenyl
- volume
- Prior art date
Links
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000003635 deoxygenating effect Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000013078 crystal Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000000921 elemental analysis Methods 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 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
- 150000003839 salts Chemical class 0.000 description 6
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 5
- 239000005708 Sodium hypochlorite Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 5
- -1 2-(substituted amidino)-1,4-benzodiazepine Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002905 orthoesters Chemical class 0.000 description 3
- TVPIWCSCVOUSLA-UHFFFAOYSA-N 7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-amine;dihydrochloride Chemical compound Cl.Cl.N=1CC(N)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 TVPIWCSCVOUSLA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003158 myorelaxant agent Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- SFXZVEKHZPHJTH-UHFFFAOYSA-N 1h-1,4-benzodiazepin-2-amine Chemical class N1C(N)=CN=CC2=CC=CC=C21 SFXZVEKHZPHJTH-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- FWEBLHYEGFAQCZ-UHFFFAOYSA-N 2-[(2-aminophenyl)methylideneamino]-2-phenylacetonitrile Chemical compound NC1=C(C=NC(C#N)C2=CC=CC=C2)C=CC=C1 FWEBLHYEGFAQCZ-UHFFFAOYSA-N 0.000 description 1
- FZKNTBXBZONMAY-UHFFFAOYSA-N 7-chloro-5-(4-methoxyphenyl)-3h-1,4-benzodiazepin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=NCC(N)=NC2=CC=C(Cl)C=C12 FZKNTBXBZONMAY-UHFFFAOYSA-N 0.000 description 1
- OKSINCZQDWSATA-UHFFFAOYSA-N 7-nitro-5-phenyl-3h-1,4-benzodiazepin-2-amine Chemical compound N=1CC(N)=NC2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 OKSINCZQDWSATA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 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 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical class BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical class [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44091720A JPS4910957B1 (xx) | 1969-11-15 | 1969-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126799B true NO126799B (xx) | 1973-03-26 |
Family
ID=14034327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO04310/70A NO126799B (xx) | 1969-11-15 | 1970-11-11 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3703525A (xx) |
| JP (1) | JPS4910957B1 (xx) |
| AT (3) | AT301559B (xx) |
| BE (1) | BE758921A (xx) |
| CH (2) | CH544102A (xx) |
| DE (2) | DE2055889C2 (xx) |
| DK (1) | DK140638B (xx) |
| ES (2) | ES385570A1 (xx) |
| FI (1) | FI51700C (xx) |
| FR (1) | FR2073363B1 (xx) |
| GB (2) | GB1336743A (xx) |
| NL (1) | NL166687C (xx) |
| NO (1) | NO126799B (xx) |
| SE (1) | SE363332B (xx) |
| YU (1) | YU35126B (xx) |
| ZA (1) | ZA707593B (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2159527A1 (de) * | 1970-12-11 | 1972-06-22 | Ciba-Geigy Ag, Basel (Schweiz) | Verfahren zur Herstellung von Diazepinderivaten und nach diesen Verfahren herstellbare neue Diazepinderivate |
| CH562246A5 (xx) * | 1971-04-08 | 1975-05-30 | Ciba Geigy Ag | |
| BE786530A (fr) * | 1971-07-23 | 1973-01-22 | Ciba Geigy | Procede de preparation de nouveaux derives de diazepine et composes obtenus |
| US4027029A (en) * | 1972-02-07 | 1977-05-31 | Ciba-Geigy Corporation | Diazepine derivatives |
| BE795020A (fr) * | 1972-02-07 | 1973-08-06 | Ciba Geigy | Procede de preparation de nouvelles diazepines |
| CH579083A5 (xx) * | 1972-12-29 | 1976-08-31 | Ciba Geigy Ag | |
| JPS5747914B2 (xx) * | 1974-04-12 | 1982-10-13 | ||
| JPS5747915B2 (xx) * | 1974-04-17 | 1982-10-13 | ||
| US4243589A (en) * | 1979-11-30 | 1981-01-06 | Hoffmann-La Roche Inc. | Triazolobenzazepines and processes for their production |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI50981C (fi) * | 1968-11-05 | 1976-09-10 | Takeda Chemical Industries Ltd | Menetelmä unilääkkeinä ja rauhoittavina lääkkeinä vaikuttavien s-triat solo-(4,3-a)(1,4)-bentsodiatsepiinien valmistamiseksi. |
| US3987052A (en) * | 1969-03-17 | 1976-10-19 | The Upjohn Company | 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
-
0
- BE BE758921D patent/BE758921A/xx not_active IP Right Cessation
-
1969
- 1969-11-15 JP JP44091720A patent/JPS4910957B1/ja active Pending
-
1970
- 1970-11-09 ZA ZA707593A patent/ZA707593B/xx unknown
- 1970-11-11 AT AT906071A patent/AT301559B/de not_active IP Right Cessation
- 1970-11-11 AT AT1015470A patent/AT301554B/de not_active IP Right Cessation
- 1970-11-11 AT AT906171A patent/AT301560B/de not_active IP Right Cessation
- 1970-11-11 NO NO04310/70A patent/NO126799B/no unknown
- 1970-11-13 YU YU2787/70A patent/YU35126B/xx unknown
- 1970-11-13 SE SE15393/70A patent/SE363332B/xx unknown
- 1970-11-13 FI FI703058A patent/FI51700C/fi active
- 1970-11-13 DK DK576970AA patent/DK140638B/da unknown
- 1970-11-13 CH CH1199973A patent/CH544102A/de not_active IP Right Cessation
- 1970-11-13 FR FR7040746A patent/FR2073363B1/fr not_active Expired
- 1970-11-13 DE DE2055889A patent/DE2055889C2/de not_active Expired
- 1970-11-13 DE DE2065714A patent/DE2065714C2/de not_active Expired
- 1970-11-13 CH CH1685670A patent/CH553797A/xx not_active IP Right Cessation
- 1970-11-13 NL NL7016706.A patent/NL166687C/xx not_active IP Right Cessation
- 1970-11-14 ES ES385570A patent/ES385570A1/es not_active Expired
- 1970-11-16 US US90139A patent/US3703525A/en not_active Expired - Lifetime
- 1970-11-16 GB GB5438370A patent/GB1336743A/en not_active Expired
- 1970-11-16 GB GB5438370A patent/GB1336744A/en not_active Expired
-
1973
- 1973-04-14 ES ES413732A patent/ES413732A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT301554B (de) | 1972-09-11 |
| BE758921A (fr) | 1971-04-16 |
| CH553797A (de) | 1974-09-13 |
| NL166687B (nl) | 1981-04-15 |
| FR2073363B1 (xx) | 1974-08-23 |
| DE2055889A1 (de) | 1971-05-27 |
| FI51700B (xx) | 1976-11-30 |
| DE2065714C2 (de) | 1982-07-01 |
| FI51700C (fi) | 1977-03-10 |
| JPS4910957B1 (xx) | 1974-03-13 |
| ES413732A1 (es) | 1976-01-16 |
| AT301559B (de) | 1972-09-11 |
| GB1336744A (en) | 1973-11-07 |
| ZA707593B (en) | 1971-07-28 |
| AT301560B (de) | 1972-09-11 |
| GB1336743A (en) | 1973-11-07 |
| FR2073363A1 (xx) | 1971-10-01 |
| DK140638B (da) | 1979-10-15 |
| NL166687C (nl) | 1981-09-15 |
| YU35126B (en) | 1980-09-25 |
| DK140638C (xx) | 1980-03-10 |
| NL7016706A (xx) | 1971-05-18 |
| SE363332B (xx) | 1974-01-14 |
| ES385570A1 (es) | 1973-11-16 |
| CH544102A (de) | 1973-12-28 |
| DE2055889C2 (de) | 1982-04-01 |
| DE2065714A1 (de) | 1975-03-13 |
| YU278770A (en) | 1980-03-15 |
| US3703525A (en) | 1972-11-21 |
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