NO128997B - - Google Patents
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- Publication number
- NO128997B NO128997B NO03276/70A NO327670A NO128997B NO 128997 B NO128997 B NO 128997B NO 03276/70 A NO03276/70 A NO 03276/70A NO 327670 A NO327670 A NO 327670A NO 128997 B NO128997 B NO 128997B
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- ethyl
- acid
- phenylsulfonyl
- imino
- Prior art date
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- 150000003839 salts Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- -1 methyl-substituted cycloheptyl group Chemical group 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KMGGBHZGPFPRGZ-UHFFFAOYSA-N 2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethanamine;dihydrochloride Chemical compound Cl.Cl.C1=CC(CCN)=CC=C1S(=O)(=O)N1C(=N)N(C2CCCCC2)CC1 KMGGBHZGPFPRGZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XXGHBKNXFXULMV-UHFFFAOYSA-N Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1CCN(C2CCCC2)C1=N Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1CCN(C2CCCC2)C1=N XXGHBKNXFXULMV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HKTCTLBSJWAWDO-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-1-propylurea Chemical compound CCCN(C(N)=O)S(=O)(=O)C1=CC=C(Cl)C=C1 HKTCTLBSJWAWDO-UHFFFAOYSA-N 0.000 description 1
- LIGJMUDWIGAHRT-UHFFFAOYSA-N 1-(benzenesulfonyl)-4,5-dihydroimidazol-2-amine Chemical compound NC1=NCCN1S(=O)(=O)C1=CC=CC=C1 LIGJMUDWIGAHRT-UHFFFAOYSA-N 0.000 description 1
- ZIRLDYOJRFPDFO-UHFFFAOYSA-N 1-butyl-1-(4-methylphenyl)sulfonylurea Chemical compound CCCCN(C(N)=O)S(=O)(=O)C1=CC=C(C)C=C1 ZIRLDYOJRFPDFO-UHFFFAOYSA-N 0.000 description 1
- IFLWJIZMQKKSKF-UHFFFAOYSA-N 2-[4-[2-imino-3-(4-methylcyclohexyl)imidazolidin-1-yl]sulfonylphenyl]ethanamine dihydrochloride Chemical compound Cl.Cl.CC1CCC(CC1)N1CCN(C1=N)S(=O)(=O)C1=CC=C(CCN)C=C1 IFLWJIZMQKKSKF-UHFFFAOYSA-N 0.000 description 1
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
- OAIRTVZAAFZBMR-UHFFFAOYSA-N 2-propan-2-yloxyacetic acid Chemical compound CC(C)OCC(O)=O OAIRTVZAAFZBMR-UHFFFAOYSA-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
- HTNUUDFQRYBJPH-UHFFFAOYSA-N 3-methoxypropanehydrazide Chemical compound COCCC(=O)NN HTNUUDFQRYBJPH-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DVNBASXKSCNLKQ-UHFFFAOYSA-N 3-propan-2-yloxypropanoic acid Chemical compound CC(C)OCCC(O)=O DVNBASXKSCNLKQ-UHFFFAOYSA-N 0.000 description 1
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- GZRRCHXCLCFXFT-UHFFFAOYSA-N Cl.Cl.NC(CC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCCC1)=N)C Chemical compound Cl.Cl.NC(CC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCCC1)=N)C GZRRCHXCLCFXFT-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 150000001199 N-acyl amides Chemical class 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- PJYGPNGTUCHYIC-UHFFFAOYSA-N bis(1h-pyrazol-5-yl)methanone Chemical compound C1=CNN=C1C(=O)C=1C=CNN=1 PJYGPNGTUCHYIC-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-M ethanimidate Chemical compound CC([O-])=N DLFVBJFMPXGRIB-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical group [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- UKPFUYSIRKPFNU-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]-2-ethoxyacetamide Chemical compound C1=CC(CCNC(=O)COCC)=CC=C1S(=O)(=O)N1C(=N)N(C2CCCCC2)CC1 UKPFUYSIRKPFNU-UHFFFAOYSA-N 0.000 description 1
- XOEJTDSWDYGGPB-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]-2-methoxyacetamide Chemical compound C1=CC(CCNC(=O)COC)=CC=C1S(=O)(=O)N1C(=N)N(C2CCCCC2)CC1 XOEJTDSWDYGGPB-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
Description
Analogifremgangsmåte for fremstilling av nye, farmakologisk virksomme derivater av P-aminoalkyl-;benzensulfonamider.
Det ble funnet at p-subst. fenylsulfonyl-2-imino-imidazolidin med den generelle formel I,
hvor R^ betyr en cykloalkylrest med 5-8 karbonatomer,
;betyr hydrogen, en etyl- eller en metylgruppe,
R, betyr en eventuelt forgrenet alkylgruppe med 1-6 karbonatomer,
m betyr 2 eller 3 og
n betyr 1 eller 2, c.;
såvel som addisjonssalter med uorganiske eller organiske syrer, viser hypoglykemisk virkning på varmblodige dyr.
I forbindelsene med den generelle formel I kan R^ f.eks.
bety cyklopentylgruppen ; hvilken eventuelt kan være substituert med alkylrester med 1 - 3 karbonatomer, cykloheksyl-gruppen, hvilkeikan være substituert med etyl eller metyl og den eventuelt med metyl substituerte cykloheptylgruppen, såvel som cyklooktylgruppen.
R^ kan f.eks. bety metyl-, etyl-, propyl-, isopropyl-, butyl-, sek.butyl-, tert.butyl-, isobutyl-, pentyl-, isopentyl-, 2,2-dimetyl-propyl-, 1-metyl-butyl-, 1-etyl-propyl- eller 1,2-dimetyl-propylgruppen, eller en rettkjedet eller forgrenet heksylrest, f.eks. en n-heksyl-, metyl-pentyl-, dimetyl-butyl-eller etyl-butylgruppe.
Etter analogifremgangsmåten ifolge oppfinnelsen fremstilles forbindelsene med den generelle formel I ved at man omsetter et amin med den generelle formel II,
hvor R^, R2 og m har den under formel I angitte
betydning,
med en karboksylsyre med den generelle formel III,
hvor R^ og n hair den under den generelle formel I
angitte betydning,
eller med et reaksjonsdyktig derivat av en slik karboksylsyre og overforer, hvis onsket, de erholdte reaksjonsproduktene i saltet av en uorganisk eller organisk syre.
Omsetningen av et amin med den generelle formel II med en karboksylsyre med den generelle formel III kan f.eks. finne sted på den måten at man med tilsvarende syre overforer forst aminet i ammonium-saltet med den generelle formel III, og derefter overforer dette ved torr oppvarming i amidet med den generelle formel I. Ifdlge en foretrukket utforelsesform av fremgangsmåten ifblge oppfinnelsen omsetter man et amin med den generelle formel II med en karboksylsyre med den generelle formel III i nærvær av et vannavspaltende middel i et inert opplbsningsmiddel. Et særlig egnet vannavspaltende middel er f.eks. N,N'-dicykloheksyl-karbodiimid. Videre kan som vannavspaltende middel karbonyl-dipyrazol anvendes. Som inert opplbsningsmiddel kommer i betraktning f.eks. hydrokarboner, som benzen, toluen eller xylen, eter, som dietyleter, dioksan eller tetrahydrofuran, klorerte hydrokarboner, som metylenklorid, kloroform, trikloretylen og lavere ketoner, som aceton eller metyletylketon.
Som reaksjonsdyktige derivater av en karboksylsyre med den generelle formel III, kommer fblgende f.eks. i betraktning: halogenider, særlig klorider, lavere alkylestere, særlig metyl- eller etylester, fenylester, amider, lavere mono- hhv. dialkylamider, særlig N-metyl- og N,N-dimetylamidet, difenylamidet, videre N-acylamider, som f.eks. acetylamidet og benzoylamidet.
Omsetningen av de foran nevnte reaksjonsdyktige derivatene av kar-boksylsyrer skjer fortrinnsvis ved romtemperatur eller ved oppvarming i et av de foran nevnte inerte organiske opplbsnings-midler. Reaksjonen kan i alminnelighet gjennomfbres uten til-setning av kondensasjonsmidler, og, hvis onsket, kan slike midler, f.eks. alkalimetallalkoholater og alkalimetallhydroksyder, imidler-tid tilsettes.
Et halogenid av en karboksylsyre med den generelle formel III omsettes ifblge oppfinnelsen fortrinnsvis i nærvær av et syre-
bindende middel. Som slike kan uorganiske baser eller salter,
som f.eks. en alkalihydroksyd, -acetat, -hydrogenkarbonat, -karbonat og -fosfat, som natriumhydroksyd, -acetat, -hydrogenkarbonat, -karbonat og -fosfat, eller de tilsvarende kaliumforbind-elser anvendes. Videre kan også kalsiumoksyd, -karbonat, såvel som -fosfat og magnesiumkarbonat anvendes. I stedet for uorganiske baser eller salter egner seg også organiske baser, som f.eks. pyridin, trimetyl- eller trietylamin, diisopropylamin, eller kol-lidin. Disse^kan, tilsatt i overskudd, også tjene som opplbsningsmiddel.
I stedet for aminer med den generelle formel II, kan man ved omsetningen ifblge oppfinnelsen med et karboksylsyreklorid også an-vende N-alkalimetallderivater av disse forbindelser, som Æ.eks. natrium-, kalium- eller litiumderivater.
UtgangsforbindeIser med den generelle formel II er på sin side nye forbindelser og kan f.eks. fremstilles ved at man omsetter et reaksjonsdyktig derivat av en sulfonsyre med den generelle formel IV,
hvor R betyr en enkel alkyl- hhv. arylrest, f.eks. en metyl-, hhv. en fenylgruppe,
m har den under formel I angitte betydning,
med 2-amino-2-imidazolin-derivater med den generelle formel V,
hvor R^ og R2 har den under formel I angitte betydning. og derefter hydrolytisk avspalter acylbeskyttelsesgruppen (R-CO-). De intermediært erholdte av formel II avledede N-acylforbindelsene er likeledes hittil ikke beskrevet i litteraturen. Som reaksjonsdyktige derivater av en sulfonsyre med den generelle formel IV kommer halogenider, særlig klorider og anhydrider med den generelle formel IVa, hvor R har den under formel IV angitte betydning, i betraktning. Anhydrider med den generelle formel IVa kan på enkel måte erholdes ved omsetning av tilsvarende substituerte sulfonsyrehalogenider med salter av tilsvarende substituerte sulfonsyrer. Karboksylsyrene med den generelle formel III kan fremstilles på enkel måte ved omsetning av alkoholater med den generelle formel VI,
hvor R^ har den under den generelle formel I angitte betydning, og hvor
m betyr et enverdig metall,
med halogenalkansyrer med den generelle formel VII,
eller dennes lavere alkylestere, samt eventuell efterfdlgende hydrolyse. De erholdte syrene blir, hvis onsket, på i og for seg kjent måte overfort i reaksjonsdyktige, funksjonelle derivater.
For fremstilling av derivater av karboksylsyrene med den generelle formel III, hvor n er lik 2, har man den mulighet å anlagre tilsvarende alkanoler til akrylsyrederivater.
Efter en annen fremgangsmåte, kommer man frem til utgangsstoffer med den generelle formel II, ved at man substituerer p-(2-aminoalkyl)-benzensulfonamidet (fremstilt analogt E. Miller, J.Amer. Chem.Soc. 62, 21ol (194o)) med den generelle formel VIII,
hvor m har den under formel I angitte betydning,
med substituerte N-(2-bromalkyl)-cyanamider i alkalisk medium.
De nye aktivstoffene eller de farmasbytisk aksepterbare saltene av disse kan administreres peroralt eller parenteralt. For salt-dannelse kan anvendes fysiologisk aksepterbare uorganiske eller organiske syrer, f.eks. saltsyre, bromhydrogensyre, svovelsyre, fosforsyre, metansulfonsyre, eddiksyre, melkesyre, ravsyre, vin-syre og maleinsyre, såvel som blodsukkersenkende sulfonylurin-stoffer, som f.eks. p-toluensulfonyl-butyl-urinstoff, p-klor-benzensulfonyl-propyl-urinstoff og p-[^2-(2-metoksy-5-klor-benza-mido)-etyl]-fenylsulfonyl-cykloheksyl-urinstoff. De daglige doser ligger mellom lo og loo mg/kg for varmblodige dyr.
De efterfdlgende eksempler redegjbr nærmere for fremstillingen
av de nye forbindelser med den generelle formel I og av hittil ikke beskrevne mellomprodukter, men representerer på ingen måte de eneste utfbrelsesformene for fremstillingen. Temperaturene er angitt i Celsiusgrader.
EKSEMPEL 1
En opplosning av 40,9 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidin-dihydroklorid med smp. 2 70°c i 100 ml vann tilsettes 150 ml 2-n natronlut og den frisatte basen ekstraheres med metylenklorid. Ekstraktet som er torket med natriumsulfat tilsettes ved 0° 20,6 g N,N'-dicyklo-heksyl-karbodiimid. Deretter tildrypper man ved 0° en opplosning av 9,0 g metoksyeddiksyre i 30 ml metylenklorid i lopet av 5 minutter. Etter to timers omroring ved 0° filtreres det utfelte N,N'-dicykloheksylurinstoffet fra og det klare fil-tratet inndampes. Det således erholdte rå l-[p-(2-metoksy-acetamido-etyl)-fenylsulfonyl]-2-imino-3-cyklopentylimidazolidin omkrystalliseres i eddikester-aceton. Det inneholder 1 mol krystallvann og smelter ved 151 - 151,5°.
På analog måte erholdes med hver gang 20,6 g N,N'-dicykloheksyl-karbodiimid og 9,0 g metoksyeddiksyre: a) fra 42,4 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin-dihydroklorid med smp. 24 7 - 250° l-[p- (2-metoksyacetamido-etyl)-fenylsulfonyl]-2-imino-3-cyklo-heksyl-imidazolidin med smp. 150 - 151° (monohydrat; i eddikester)5 b) fra 43,8 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-(4-metylcykloheksyl)-imidazolidin-dihydroklorid med smp. 260° l-[p- (2-metoksyacetamido-etyl)-fenylsulfonyl]-2-imino-3-(4-metylcykloheksyD-imidazolidin, smp. 159 - 160° (hemihydrat;
i eddikester).
EKSEMPEL 2
En opplosning av 42,3 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin-dihydroklorid med smp. 24 7 - 250°C i 200 ml vann tilsettes 300 ml 2-n natronlut og ekstraheres med metylenklorid. Ekstraktet, som er torket med natriumsulfat, tilsettes 50,5 g trietylamin. Deretter tildrypper man ved romtemperatur en opplosning av 13,5 g etoksyacetylklorid i 100 ml metylenklorid i lbpet av 20 minutter og rorer den erholdte blandingen en time ved romtemperatur. Deretter vaskes reaksjonslosningen forst med 100 ml 2-n natronlut og deretter to ganger med 100 ml vann. De forente vandige fasene ekstraheres nå to ganger med metylenklorid og de erholdte metylen-kloridekstraktene forenes med den vaskede reaksjonslosningen. Ved inndampning av den med natriumsulfat torkede metylenklorid-losningen erholder man det rå l-[p-(2-etoksy-acetamido-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin, hvilket
smelter ved omkrystallisasjon i eddikester —petroleter med 111 - 113°.
På analog måte erholdes med 50,5 g trietylamin:
a) fra 43,7 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cyklopentyl-imidazolidin-dihydroklorid med smp. 270° og 13,5
g etoksyacetylklorid l-[p- (2-etoksyacetamido-etyl)-fenylsul-fonyl]-2-imino-3-cyklopentyl-imidazolidin med smp. 105 - 106,5° (i eddikester);
EKSEMPEL 3
Analogt eksempel 1 erholdes ved anvendelse av hver gang 20,6 g N ,N.j.-dicykloheksyl-karbodiimid: fra 42,3 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin-dihydroklorid og 11,8 g propoksy-eddiksyre l-[p- (2- (propoksy-acetamido)-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin, smp. lOO - 102°.
fra 42,3 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cykloheksyl-imidazolidin-dihydroklorid og 11,8 g isopropoksy-eddiksyre l-[p-(2-(isopropoksy-acetamido)-etyl)-fenylsulfonyl]-2- imino-3-cykloheksyl-imidazolidin, smp. 105 - 107°.
fra 43,7 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-(2-metyl-cykloheksyl)-imidazolidin-dihydroklorid og 10,4 g 3- metoksy-propionsyre l-[p- (3-metoksy-propionamido)-etyl)-fenylsulfonyl]-2-imino-3- (2-metyl-cykloheksyl-imidazolidin, smp. 130 - 132°.
fra 42,3 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-cyklo-
heksyl-imidazolidin-dihydroklorid og 11,8 g 3-acetoksypropion-syre 1- [p-(2-(3-etoksy-propionamido)-etyl)-fenylsulfonyl] -2-imino-3-cykloheksyl-imidazolidin, smp. 13o - 132°.
fra 43,7 g 1-jjp-(2-amino-etyl) -f enylsulf onyl] -2-imino-3-(2-metyl-cykloheksyl)-imidazolidin-dihydroklorid og 13,2 g 3-isopropoksy-propionsyre l-[p-(2-(3-isopropoksypropionamido)-etyl)-fenylsulfonyl]-2-imino-3-(2-metylcykloheksyl)-imidazolidin, smp. 128 - 13o°.
fra 43,7 g 1-[p- (2-amino-propyl) -f enylsulf onyl] -2-imino-3-cykloheksyl-imidazolidin-dihydroklorid og 9,o g metoksyeddiksyre l-[p-(2-(metoksy-acetamido)-propyl-fenylsulfonyl] -2-imino-3-cykloheksyl-imidazolidin, smp. 12o - 121°.
fra 43,7 g l-[p-(2-amino-etyl)-fenylsulfonyl] -2-imino-3-cykloheksyl-4-metyl-imidazolidin-dihydroklorid og lo,4 g etoksy-eddiksyrejjL- p-(2-etoksy-acetamido)-etyl)-fenylsul-fonyl] -2-imino-3-cykloheksyl-4-metyl-imidazolidin, smp. 115-117°.
fra 42,1 g l-[p-(2-amino-etyl)-fenylsulfonyl]-2-imino-3-(3-cykloheksen-l-yl)-imidazolidin-dihydroklorid og 9,o g metoksyeddiksyre l-[p-(2-metoksy-acetamido)-etyl)-fenylsulfonyl]-2-imino-3-(3-cykloheksen-l-yl)-imidazolidin.
Claims (1)
- Analogifremgangsmåte for fremstilling av nye, farmakologisk aktive derivater av p-aminoalkyl-benzensulfonamidet med den generelle formel I,hvor betyr en cykloalkylrest med 5-8 karbonatomer ,R2 betyr hydrogen, en etyl- eller en metylgruppe, R^ betyr en eventuelt forgrenet alkylgruppe med 1-6 karbonatomer, m betyr 2 eller 3 og n betyr 1 eller 2, såvel som deres addisjonssalter med uorganiske eller organiske syrer, karakterisert ved at man omsetter en forbindelse med den generelle formel II, hvor R^, R. og m har den under formel I angitte betydning, med en karboksylsyre med den generelle formel III, hvor R^ og n har den under den generelle formel I angitte betydning, eller med et reaksjonsdyktig derivat av en slik karboksylsyre og overforer det erholdte reaksjonsproduktet, hvis onsket, i saltet til en uorganisk eller organisk syre.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1340069A CH519501A (de) | 1969-09-04 | 1969-09-04 | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128997B true NO128997B (no) | 1974-02-11 |
Family
ID=4392089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO03276/70A NO128997B (no) | 1969-09-04 | 1970-08-27 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3729462A (no) |
| AT (1) | AT294824B (no) |
| BE (1) | BE755685A (no) |
| BG (1) | BG17962A3 (no) |
| CA (1) | CA920601A (no) |
| CH (2) | CH519501A (no) |
| CS (1) | CS166015B2 (no) |
| DE (1) | DE2043773C3 (no) |
| DK (1) | DK131674C (no) |
| ES (1) | ES383344A1 (no) |
| FI (1) | FI52573C (no) |
| FR (1) | FR2070671B1 (no) |
| GB (1) | GB1306602A (no) |
| IE (1) | IE34504B1 (no) |
| IL (1) | IL35224A (no) |
| NL (1) | NL165155C (no) |
| NO (1) | NO128997B (no) |
| PL (1) | PL73403B1 (no) |
| SE (1) | SE367824B (no) |
| SU (1) | SU398039A3 (no) |
| ZA (1) | ZA706044B (no) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2881427A1 (fr) * | 2005-01-31 | 2006-08-04 | Oreal | Derives de 3-sulfanylpropanamide, composition les contenant et leur utilisation pour stimuler la pousse des cheveux et des cils et/ou freiner leur chute et/ou limiter leur depigmentation |
-
0
- BE BE755685D patent/BE755685A/xx unknown
-
1969
- 1969-09-04 CH CH1340069A patent/CH519501A/de not_active IP Right Cessation
- 1969-09-04 CH CH74872A patent/CH518945A/de not_active IP Right Cessation
-
1970
- 1970-08-27 NO NO03276/70A patent/NO128997B/no unknown
- 1970-08-27 FI FI702364A patent/FI52573C/fi active
- 1970-08-27 NL NL7012732.A patent/NL165155C/xx not_active IP Right Cessation
- 1970-08-27 SE SE11648/70A patent/SE367824B/xx unknown
- 1970-08-27 DK DK440870A patent/DK131674C/da active
- 1970-09-01 US US00068793A patent/US3729462A/en not_active Expired - Lifetime
- 1970-09-03 CS CS6050A patent/CS166015B2/cs unknown
- 1970-09-03 AT AT802270A patent/AT294824B/de not_active IP Right Cessation
- 1970-09-03 IE IE1148/70A patent/IE34504B1/xx unknown
- 1970-09-03 FR FR7032047A patent/FR2070671B1/fr not_active Expired
- 1970-09-03 CA CA092253A patent/CA920601A/en not_active Expired
- 1970-09-03 ZA ZA706044A patent/ZA706044B/xx unknown
- 1970-09-03 ES ES383344A patent/ES383344A1/es not_active Expired
- 1970-09-03 SU SU1471571A patent/SU398039A3/ru active
- 1970-09-03 GB GB4210670A patent/GB1306602A/en not_active Expired
- 1970-09-03 DE DE2043773A patent/DE2043773C3/de not_active Expired
- 1970-09-03 BG BG15600A patent/BG17962A3/xx unknown
- 1970-09-03 IL IL35224A patent/IL35224A/en unknown
- 1970-09-03 PL PL1970142967A patent/PL73403B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE34504L (en) | 1971-03-04 |
| DE2043773C3 (de) | 1980-02-21 |
| SE367824B (no) | 1974-06-10 |
| IL35224A (en) | 1973-11-28 |
| US3729462A (en) | 1973-04-24 |
| PL73403B1 (no) | 1974-08-30 |
| FI52573C (fi) | 1977-10-10 |
| DK131674C (da) | 1976-01-19 |
| IE34504B1 (en) | 1975-05-28 |
| CS166015B2 (no) | 1976-01-29 |
| FR2070671A1 (no) | 1971-09-17 |
| IL35224A0 (en) | 1970-11-30 |
| CA920601A (en) | 1973-02-06 |
| ZA706044B (en) | 1971-04-28 |
| NL165155C (nl) | 1981-03-16 |
| FR2070671B1 (no) | 1973-12-21 |
| NL7012732A (no) | 1971-03-08 |
| CH519501A (de) | 1972-02-29 |
| DE2043773B2 (de) | 1979-06-28 |
| NL165155B (nl) | 1980-10-15 |
| ES383344A1 (es) | 1973-01-01 |
| AT294824B (de) | 1971-12-10 |
| BE755685A (fr) | 1971-03-03 |
| SU398039A3 (no) | 1973-09-17 |
| GB1306602A (en) | 1973-02-14 |
| DE2043773A1 (de) | 1971-03-18 |
| FI52573B (no) | 1977-06-30 |
| BG17962A3 (no) | 1974-03-05 |
| DK131674B (da) | 1975-08-18 |
| CH518945A (de) | 1972-02-15 |
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