CH506544A - Verfahren zur Herstellung von biologisch aktiven substituierten s-Triazinen - Google Patents
Verfahren zur Herstellung von biologisch aktiven substituierten s-TriazinenInfo
- Publication number
- CH506544A CH506544A CH43068A CH43068A CH506544A CH 506544 A CH506544 A CH 506544A CH 43068 A CH43068 A CH 43068A CH 43068 A CH43068 A CH 43068A CH 506544 A CH506544 A CH 506544A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- compound
- mol
- formula
- triazine
- Prior art date
Links
- 230000001741 anti-phlogistic effect Effects 0.000 title abstract 2
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 29
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims 1
- FYNZLNTWHGFUEV-UHFFFAOYSA-N 1-(1h-pyrrol-2-yl)piperidine Chemical compound C1CCCCN1C1=CC=CN1 FYNZLNTWHGFUEV-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- -1 aliphatic amines Chemical class 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 229960005141 piperazine Drugs 0.000 description 7
- 229960003506 piperazine hexahydrate Drugs 0.000 description 7
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- ALBALSYPOLVIBQ-UHFFFAOYSA-N ClC1=NC(Cl)=NC(NN=CC=2C=CC=CC=2)=N1 Chemical compound ClC1=NC(Cl)=NC(NN=CC=2C=CC=CC=2)=N1 ALBALSYPOLVIBQ-UHFFFAOYSA-N 0.000 description 5
- DUJOMJVTFLDFHI-UHFFFAOYSA-N N-(benzylideneamino)-4-morpholin-4-yl-6-piperazin-1-yl-1,3,5-triazin-2-amine Chemical compound O1CCN(CC1)C=1NC(N=C(N1)N1CCNCC1)=NN=CC1=CC=CC=C1 DUJOMJVTFLDFHI-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
- JNWKVYHHZDMNPE-UHFFFAOYSA-N (4-morpholin-4-yl-6-piperazin-1-yl-1,3,5-triazin-2-yl)hydrazine Chemical compound N=1C(NN)=NC(N2CCNCC2)=NC=1N1CCOCC1 JNWKVYHHZDMNPE-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- LKPFWCPZERQLFI-UHFFFAOYSA-N 2,4,6-trimethylpyridine;hydrochloride Chemical compound Cl.CC1=CC(C)=NC(C)=C1 LKPFWCPZERQLFI-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- LEXOZHHIDPMMAC-YFHOEESVSA-N (z)-1-phenylethylidenehydrazine Chemical compound N/N=C(/C)C1=CC=CC=C1 LEXOZHHIDPMMAC-YFHOEESVSA-N 0.000 description 1
- DXUMYHZTYVPBEZ-UHFFFAOYSA-N 2,4,6-tris(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 DXUMYHZTYVPBEZ-UHFFFAOYSA-N 0.000 description 1
- RSDAJSLPLORXCE-UHFFFAOYSA-N 3,5-dimethyl-1H-pyrazole hydrochloride Chemical compound Cl.CC1=NNC(=C1)C RSDAJSLPLORXCE-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NPZBRCNVYUBMHG-UHFFFAOYSA-N C(C)NC=1NC(N=C(N1)N1CCNCC1)=NN=CC1=CC=CC=C1 Chemical compound C(C)NC=1NC(N=C(N1)N1CCNCC1)=NN=CC1=CC=CC=C1 NPZBRCNVYUBMHG-UHFFFAOYSA-N 0.000 description 1
- FQXHZAVYZJXBMK-UHFFFAOYSA-N CC1=CC(Cl)=CC(Cl)=C1C=NN=C1N=CN=CN1 Chemical compound CC1=CC(Cl)=CC(Cl)=C1C=NN=C1N=CN=CN1 FQXHZAVYZJXBMK-UHFFFAOYSA-N 0.000 description 1
- MGRTYZRZXHGKLN-UHFFFAOYSA-N CC1=CC(Cl)=CC(N2CCOCC2)=C1C=NN=C1N=CN=CN1 Chemical compound CC1=CC(Cl)=CC(N2CCOCC2)=C1C=NN=C1N=CN=CN1 MGRTYZRZXHGKLN-UHFFFAOYSA-N 0.000 description 1
- UAPCQVSJTYDMIT-UHFFFAOYSA-N CCNC(N1)=NC(Cl)=NC1=NN=CC1=CC=CC=C1 Chemical compound CCNC(N1)=NC(Cl)=NC1=NN=CC1=CC=CC=C1 UAPCQVSJTYDMIT-UHFFFAOYSA-N 0.000 description 1
- HDTAYGZNZKNAHF-UHFFFAOYSA-N ClC1=CC(Cl)=C(C=NN=C2N=CN=CN2)C(C2=CC=CC=C2)=C1 Chemical compound ClC1=CC(Cl)=C(C=NN=C2N=CN=CN2)C(C2=CC=CC=C2)=C1 HDTAYGZNZKNAHF-UHFFFAOYSA-N 0.000 description 1
- FMTCNMBEENKRBV-UHFFFAOYSA-N N-(benzylideneamino)-4,6-di(piperazin-1-yl)-1,3,5-triazin-2-amine Chemical compound N1(CCNCC1)C=1NC(N=C(N1)N1CCNCC1)=NN=CC1=CC=CC=C1 FMTCNMBEENKRBV-UHFFFAOYSA-N 0.000 description 1
- AJEBRFSHJYPODA-UHFFFAOYSA-N N1(CCCCC1)C=1NC(N=C(N1)N1CCNCC1)=NN=CC1=CC=CC=C1 Chemical compound N1(CCCCC1)C=1NC(N=C(N1)N1CCNCC1)=NN=CC1=CC=CC=C1 AJEBRFSHJYPODA-UHFFFAOYSA-N 0.000 description 1
- NTRPAMGRKOPFSZ-UHFFFAOYSA-N N1(CCCCC1)C=1NC(N=C(N=1)Cl)=NN=CC1=CC=CC=C1 Chemical compound N1(CCCCC1)C=1NC(N=C(N=1)Cl)=NN=CC1=CC=CC=C1 NTRPAMGRKOPFSZ-UHFFFAOYSA-N 0.000 description 1
- LGZDQSDAHJTRFX-UHFFFAOYSA-N O1CCN(CC1)C1N(CCN(C1)C(=O)OCC)C=1NC(N=CN1)=NN=CC1=CC=CC=C1 Chemical compound O1CCN(CC1)C1N(CCN(C1)C(=O)OCC)C=1NC(N=CN1)=NN=CC1=CC=CC=C1 LGZDQSDAHJTRFX-UHFFFAOYSA-N 0.000 description 1
- OCHUFEQTEADAIO-UHFFFAOYSA-N O1CCN(CC1)C=1NC(N=C(N=1)Cl)=NN=CC1=CC=CC=C1 Chemical compound O1CCN(CC1)C=1NC(N=C(N=1)Cl)=NN=CC1=CC=CC=C1 OCHUFEQTEADAIO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 150000007514 bases Chemical class 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
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0052314 | 1967-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH506544A true CH506544A (de) | 1971-04-30 |
Family
ID=7054073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH43068A CH506544A (de) | 1967-02-17 | 1968-01-11 | Verfahren zur Herstellung von biologisch aktiven substituierten s-Triazinen |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE710932A (en。) |
| CH (1) | CH506544A (en。) |
| DE (1) | DE1670550B2 (en。) |
| FR (2) | FR1568885A (en。) |
| GB (1) | GB1164594A (en。) |
| IL (1) | IL29447A (en。) |
| NL (1) | NL6801544A (en。) |
| SE (1) | SE355021B (en。) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2465405A (en) * | 2008-11-10 | 2010-05-19 | Univ Basel | Triazine, pyrimidine and pyridine analogues and their use in therapy |
| HUE030368T2 (en) | 2010-07-20 | 2017-05-29 | Vestaron Corp | Insecticide triazines and pyrimidines |
-
1967
- 1967-02-17 DE DE19671670550 patent/DE1670550B2/de active Granted
-
1968
- 1968-01-11 CH CH43068A patent/CH506544A/de not_active IP Right Cessation
- 1968-02-02 NL NL6801544A patent/NL6801544A/xx unknown
- 1968-02-09 FR FR1568885D patent/FR1568885A/fr not_active Expired
- 1968-02-11 IL IL29447A patent/IL29447A/xx unknown
- 1968-02-12 FR FR139496A patent/FR8023M/fr not_active Expired
- 1968-02-14 SE SE01939/68A patent/SE355021B/xx unknown
- 1968-02-16 BE BE710932D patent/BE710932A/xx unknown
- 1968-02-19 GB GB8048/68A patent/GB1164594A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR8023M (en。) | 1970-08-03 |
| DE1670550A1 (de) | 1972-02-24 |
| SE355021B (en。) | 1973-04-02 |
| BE710932A (en。) | 1968-07-01 |
| IL29447A (en) | 1971-11-29 |
| DE1670550C3 (en。) | 1973-11-22 |
| GB1164594A (en) | 1969-09-17 |
| FR1568885A (en。) | 1969-05-30 |
| DE1670550B2 (de) | 1973-04-26 |
| NL6801544A (en。) | 1968-08-19 |
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