NO124373B - - Google Patents
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- Publication number
- NO124373B NO124373B NO2971/70A NO297170A NO124373B NO 124373 B NO124373 B NO 124373B NO 2971/70 A NO2971/70 A NO 2971/70A NO 297170 A NO297170 A NO 297170A NO 124373 B NO124373 B NO 124373B
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- imino
- phenylsulfonyl
- imidazolidine
- amino
- Prior art date
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- -1 polymethylene chain Polymers 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 238000002360 preparation method Methods 0.000 claims description 5
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 178
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 235000011121 sodium hydroxide Nutrition 0.000 description 27
- 239000007858 starting material Substances 0.000 description 23
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 238000001816 cooling Methods 0.000 description 21
- 239000000155 melt Substances 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 235000011054 acetic acid Nutrition 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000052 vinegar Substances 0.000 description 17
- 235000021419 vinegar Nutrition 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 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 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 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 13
- IFZHITIIUYASRA-UHFFFAOYSA-N 2-[4-(3-butyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethanamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCC)=N IFZHITIIUYASRA-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 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 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 230000001476 alcoholic effect Effects 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000004540 pour-on Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IAERAFZPWNQKDJ-UHFFFAOYSA-N [4-(2-aminoethyl)phenyl]sulfonylazanium;chloride Chemical compound [Cl-].NS(=O)(=O)C1=CC=C(CC[NH3+])C=C1 IAERAFZPWNQKDJ-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- TUFJIDJGIQOYFY-UHFFFAOYSA-N 2-isothiocyanatobutane Chemical compound CCC(C)N=C=S TUFJIDJGIQOYFY-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- SETZYUAKRVTFIN-UHFFFAOYSA-N Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(C(C1)C)CCCC)=N Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(C(C1)C)CCCC)=N SETZYUAKRVTFIN-UHFFFAOYSA-N 0.000 description 4
- PKCVXIPHDFILSW-UHFFFAOYSA-N Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N PKCVXIPHDFILSW-UHFFFAOYSA-N 0.000 description 4
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
- LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical compound CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KRCLYFSUYKGUDP-UHFFFAOYSA-N 2-[4-(2-imino-5-methyl-3-propylimidazolidin-1-yl)sulfonylphenyl]ethanamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCC)=N KRCLYFSUYKGUDP-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
- 239000013543 active substance Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000001439 (2R)-2-isothiocyanatobutane Substances 0.000 description 2
- MDGPKPJUIQTTTM-UHFFFAOYSA-N 2-[4-(3-butyl-2-imino-5-methylimidazolidin-1-yl)sulfonylphenyl]ethanamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCCC)=N MDGPKPJUIQTTTM-UHFFFAOYSA-N 0.000 description 2
- SKWDIXBVQATQSG-UHFFFAOYSA-N 2-chloro-5-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(C(O)=O)=C1 SKWDIXBVQATQSG-UHFFFAOYSA-N 0.000 description 2
- ZFWFRTVIIMTOLY-UHFFFAOYSA-N 2-isothiocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=S ZFWFRTVIIMTOLY-UHFFFAOYSA-N 0.000 description 2
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- NIXOMDXYSSDZCJ-UHFFFAOYSA-N Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCC)=N Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCC)=N NIXOMDXYSSDZCJ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- MVCPJTDZPHSWDT-UHFFFAOYSA-N O.Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N Chemical compound O.Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N MVCPJTDZPHSWDT-UHFFFAOYSA-N 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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 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
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000010438 heat treatment Methods 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
- 238000004519 manufacturing process Methods 0.000 description 2
- XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 description 2
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 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
- 238000010992 reflux Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 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
- IJFOCKLZHLDYOC-UHFFFAOYSA-N 1-[2-[4-(3-butyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]-3-cyclohex-3-en-1-ylthiourea Chemical compound C1(CC=CCC1)NC(NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCC)=N)=S IJFOCKLZHLDYOC-UHFFFAOYSA-N 0.000 description 1
- UGYDNPVAOQSBPS-UHFFFAOYSA-N 1-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]-3-cyclopentylthiourea Chemical compound N=C1N(C2CCCCC2)CCN1S(=O)(=O)C(C=C1)=CC=C1CCNC(=S)NC1CCCC1 UGYDNPVAOQSBPS-UHFFFAOYSA-N 0.000 description 1
- CVSSKUBPMMGPLF-UHFFFAOYSA-N 1-[2-[4-(3-cyclopentyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]-3-ethylthiourea Chemical compound CCNC(=S)NCCC1=CC=C(C=C1)S(=O)(=O)N1CCN(C2CCCC2)C1=N CVSSKUBPMMGPLF-UHFFFAOYSA-N 0.000 description 1
- ZSAQYGMPXBQGDC-UHFFFAOYSA-N 1-[2-[4-[2-imino-3-(4-methylcyclohexyl)imidazolidin-1-yl]sulfonylphenyl]ethyl]-3-propylurea Chemical compound C(CC)NC(NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCC(CC1)C)=N)=O ZSAQYGMPXBQGDC-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
- DDRDBILMIMLNDF-UHFFFAOYSA-N 1-butyl-3-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]urea Chemical compound C1=CC(CCNC(=O)NCCCC)=CC=C1S(=O)(=O)N1C(=N)N(C2CCCCC2)CC1 DDRDBILMIMLNDF-UHFFFAOYSA-N 0.000 description 1
- PVYDJRHPECQXDP-UHFFFAOYSA-N 1-butylimidazolidine Chemical compound CCCCN1CCNC1 PVYDJRHPECQXDP-UHFFFAOYSA-N 0.000 description 1
- LLPCIJIXICNULR-UHFFFAOYSA-N 1-cyclohexyl-4,5-dihydroimidazol-2-amine Chemical compound N=C1NCCN1C1CCCCC1 LLPCIJIXICNULR-UHFFFAOYSA-N 0.000 description 1
- UQNAQAROTUILLB-UHFFFAOYSA-N 1-isocyanato-3-methylbutane Chemical compound CC(C)CCN=C=O UQNAQAROTUILLB-UHFFFAOYSA-N 0.000 description 1
- JATNWMBUDXLMEO-UHFFFAOYSA-N 1-isothiocyanato-3-methylbutane Chemical compound CC(C)CCN=C=S JATNWMBUDXLMEO-UHFFFAOYSA-N 0.000 description 1
- LYIHNFCGUFETAP-UHFFFAOYSA-N 1-isothiocyanatocyclohexene Chemical compound S=C=NC1=CCCCC1 LYIHNFCGUFETAP-UHFFFAOYSA-N 0.000 description 1
- WXYAXKKXIGHXDS-UHFFFAOYSA-N 1-isothiocyanatohexane Chemical compound CCCCCCN=C=S WXYAXKKXIGHXDS-UHFFFAOYSA-N 0.000 description 1
- KKASGUHLXWAKEZ-UHFFFAOYSA-N 1-isothiocyanatopropane Chemical compound CCCN=C=S KKASGUHLXWAKEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- BWVWYLWQVXEGDZ-UHFFFAOYSA-N 2-bromoethyl(cyclohexyl)cyanamide Chemical compound BrCCN(C#N)C1CCCCC1 BWVWYLWQVXEGDZ-UHFFFAOYSA-N 0.000 description 1
- QRBBHPXLBAWRQG-UHFFFAOYSA-N 2-chloroethyl(cyclopentyl)cyanamide Chemical compound ClCCN(C#N)C1CCCC1 QRBBHPXLBAWRQG-UHFFFAOYSA-N 0.000 description 1
- IMMWXRJMBHEVIP-UHFFFAOYSA-N 2-chloroethyl(propyl)cyanamide Chemical compound ClCCN(C#N)CCC IMMWXRJMBHEVIP-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-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
- 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- CFLOEWZVQZAZRW-UHFFFAOYSA-N C(CC)NC(NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(C(C1)C)CCCC)=N)=O Chemical compound C(CC)NC(NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(C(C1)C)CCCC)=N)=O CFLOEWZVQZAZRW-UHFFFAOYSA-N 0.000 description 1
- DGDVOAMNBORAHW-UHFFFAOYSA-N CC(C)CN1CCN(C1=N)S(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 Chemical compound CC(C)CN1CCN(C1=N)S(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 DGDVOAMNBORAHW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QAHCMZKTFRUHKX-UHFFFAOYSA-N Cl.C(CCC)N1C(=NCC1)N Chemical compound Cl.C(CCC)N1C(=NCC1)N QAHCMZKTFRUHKX-UHFFFAOYSA-N 0.000 description 1
- XWBHFCQCSPJKDJ-UHFFFAOYSA-N Cl.Cl.N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCCC)=N Chemical compound Cl.Cl.N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCCC)=N XWBHFCQCSPJKDJ-UHFFFAOYSA-N 0.000 description 1
- NDGHDTMMXDGXPT-UHFFFAOYSA-N Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C(C)C(CC)C)=N Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C(C)C(CC)C)=N NDGHDTMMXDGXPT-UHFFFAOYSA-N 0.000 description 1
- YCKLBCBTFLQEGH-UHFFFAOYSA-N Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C(C)C)=N Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C(C)C)=N YCKLBCBTFLQEGH-UHFFFAOYSA-N 0.000 description 1
- RCQMQPMDDLTCQP-UHFFFAOYSA-N ClCCN(C#N)C1CCC(CC1)C Chemical compound ClCCN(C#N)C1CCC(CC1)C RCQMQPMDDLTCQP-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
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- NXAUJCQGNVSSNV-UHFFFAOYSA-N N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCC)=N Chemical compound N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCC)=N NXAUJCQGNVSSNV-UHFFFAOYSA-N 0.000 description 1
- MNTHPLSYGFGBLK-UHFFFAOYSA-N N-[2-[4-(3-butyl-2-imino-4-methylimidazolidin-1-yl)sulfonylphenyl]ethyl]acetamide Chemical compound CCCCN1C(C)CN(C1=N)S(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 MNTHPLSYGFGBLK-UHFFFAOYSA-N 0.000 description 1
- DEWFPFYAXBRYJB-UHFFFAOYSA-N N-[2-[4-(3-butyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]acetamide Chemical class C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCC)=N DEWFPFYAXBRYJB-UHFFFAOYSA-N 0.000 description 1
- PXRMKVUCTBQBDK-UHFFFAOYSA-N N-[2-[4-(3-cyclopentyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]acetamide Chemical compound N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCC1)=N PXRMKVUCTBQBDK-UHFFFAOYSA-N 0.000 description 1
- OOAHCJDVPGESFA-UHFFFAOYSA-N N-[2-[4-[benzenesulfonyl(carbamoyl)amino]cyclohexyl]ethyl]-5-chloro-2-methoxybenzamide Chemical compound COC1=C(C(=O)NCCC2CCC(CC2)N(C(=O)N)S(=O)(=O)C2=CC=CC=C2)C=C(C=C1)Cl OOAHCJDVPGESFA-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
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 239000002253 acid 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
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines 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
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- HLOVCHVXIIXUHK-UHFFFAOYSA-N butyl(2-chloroethyl)cyanamide Chemical compound ClCCN(C#N)CCCC HLOVCHVXIIXUHK-UHFFFAOYSA-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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical compound NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 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
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- CZALJDQHONFVFU-UHFFFAOYSA-N isocyanatocyclopentane Chemical compound O=C=NC1CCCC1 CZALJDQHONFVFU-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- MZSJGCPBOVTKHR-UHFFFAOYSA-N isothiocyanatocyclohexane Chemical compound S=C=NC1CCCCC1 MZSJGCPBOVTKHR-UHFFFAOYSA-N 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
- 125000005394 methallyl group Chemical group 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 1
- IEQUJSXSDUKTLF-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]acetamide Chemical compound C1=CC(CCNC(=O)C)=CC=C1S(=O)(=O)N1C(=N)N(C2CCCCC2)CC1 IEQUJSXSDUKTLF-UHFFFAOYSA-N 0.000 description 1
- CHGVIQWWXDOWRN-UHFFFAOYSA-N n-butyl-n-methylcarbamoyl chloride Chemical compound CCCCN(C)C(Cl)=O CHGVIQWWXDOWRN-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- BIFDXOOJPDHKJH-UHFFFAOYSA-N piperidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCC1 BIFDXOOJPDHKJH-UHFFFAOYSA-N 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
- 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
- 125000001424 substituent group Chemical group 0.000 description 1
- BPSUJSDZHLTNJR-UHFFFAOYSA-N sulfamide;hydrochloride Chemical compound Cl.NS(N)(=O)=O BPSUJSDZHLTNJR-UHFFFAOYSA-N 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
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 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
- 230000007306 turnover Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1208569A CH513874A (de) | 1969-08-08 | 1969-08-08 | Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124373B true NO124373B (cs) | 1972-04-10 |
Family
ID=4379702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2971/70A NO124373B (cs) | 1969-08-08 | 1970-07-31 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3725430A (cs) |
| AT (1) | AT303750B (cs) |
| BE (1) | BE754597A (cs) |
| BG (2) | BG17961A3 (cs) |
| CA (1) | CA925089A (cs) |
| CH (2) | CH518287A (cs) |
| DE (1) | DE2039419C3 (cs) |
| DK (1) | DK125854B (cs) |
| ES (1) | ES382540A1 (cs) |
| FI (1) | FI52461C (cs) |
| FR (1) | FR2068476B1 (cs) |
| GB (1) | GB1313578A (cs) |
| IE (1) | IE34445B1 (cs) |
| IL (1) | IL35080A (cs) |
| NL (1) | NL167423C (cs) |
| NO (1) | NO124373B (cs) |
| PL (1) | PL80964B1 (cs) |
| SE (1) | SE367408B (cs) |
| ZA (1) | ZA705468B (cs) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1052113A (cs) * | 1963-02-07 | |||
| DE1218154B (de) * | 1964-04-20 | 1966-06-02 | Bayer Ag | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| US3538085A (en) * | 1966-03-24 | 1970-11-03 | Geigy Chem Corp | 1-phenylsulfonyl-2-imino-imidazolidines and hexahydropyrimidines |
| CH505829A (de) * | 1968-03-14 | 1971-04-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkylbenzolsulfonamids |
-
0
- BE BE754597D patent/BE754597A/xx unknown
-
1969
- 1969-08-08 CH CH1260271A patent/CH518287A/de not_active IP Right Cessation
- 1969-08-08 CH CH1208569A patent/CH513874A/de not_active IP Right Cessation
-
1970
- 1970-07-31 DK DK397270AA patent/DK125854B/da not_active IP Right Cessation
- 1970-07-31 FI FI702117A patent/FI52461C/fi active
- 1970-07-31 NL NL7011391.A patent/NL167423C/xx not_active IP Right Cessation
- 1970-07-31 SE SE10548/70A patent/SE367408B/xx unknown
- 1970-07-31 NO NO2971/70A patent/NO124373B/no unknown
- 1970-08-05 US US00061510A patent/US3725430A/en not_active Expired - Lifetime
- 1970-08-07 BG BG15430A patent/BG17961A3/xx unknown
- 1970-08-07 IL IL35080A patent/IL35080A/en unknown
- 1970-08-07 IE IE1022/70A patent/IE34445B1/xx unknown
- 1970-08-07 PL PL1970142702A patent/PL80964B1/pl unknown
- 1970-08-07 ES ES382540A patent/ES382540A1/es not_active Expired
- 1970-08-07 FR FR7029218A patent/FR2068476B1/fr not_active Expired
- 1970-08-07 DE DE2039419A patent/DE2039419C3/de not_active Expired
- 1970-08-07 GB GB3816970A patent/GB1313578A/en not_active Expired
- 1970-08-07 CA CA090196A patent/CA925089A/en not_active Expired
- 1970-08-07 BG BG16384A patent/BG17544A3/xx unknown
- 1970-08-07 ZA ZA705468A patent/ZA705468B/xx unknown
- 1970-08-07 AT AT722070A patent/AT303750B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH513874A (de) | 1971-10-15 |
| IL35080A (en) | 1973-11-28 |
| DE2039419B2 (de) | 1978-01-05 |
| DE2039419C3 (de) | 1978-09-14 |
| SE367408B (cs) | 1974-05-27 |
| ES382540A1 (es) | 1972-12-01 |
| FI52461C (fi) | 1977-09-12 |
| FI52461B (cs) | 1977-05-31 |
| FR2068476A1 (cs) | 1971-08-27 |
| AT303750B (de) | 1972-12-11 |
| DE2039419A1 (de) | 1971-02-18 |
| NL167423C (nl) | 1981-12-16 |
| IE34445B1 (en) | 1975-05-14 |
| PL80964B1 (cs) | 1975-08-30 |
| GB1313578A (en) | 1973-04-11 |
| IE34445L (en) | 1971-02-08 |
| CA925089A (en) | 1973-04-24 |
| BG17544A3 (cs) | 1973-11-10 |
| ZA705468B (en) | 1971-04-28 |
| BE754597A (fr) | 1971-02-08 |
| US3725430A (en) | 1973-04-03 |
| IL35080A0 (en) | 1970-10-30 |
| CH518287A (de) | 1972-01-31 |
| FR2068476B1 (cs) | 1973-12-21 |
| NL7011391A (cs) | 1971-02-10 |
| DK125854B (da) | 1973-05-14 |
| NL167423B (nl) | 1981-07-16 |
| BG17961A3 (cs) | 1974-03-05 |
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