CH518287A - Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamids - Google Patents
Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamidsInfo
- Publication number
- CH518287A CH518287A CH1260271A CH1260271A CH518287A CH 518287 A CH518287 A CH 518287A CH 1260271 A CH1260271 A CH 1260271A CH 1260271 A CH1260271 A CH 1260271A CH 518287 A CH518287 A CH 518287A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl
- imino
- phenylsulfonyl
- imidazolidine
- carbon atoms
- Prior art date
Links
- 230000002218 hypoglycaemic effect Effects 0.000 title abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
- 239000012948 isocyanate Substances 0.000 claims abstract description 5
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 5
- 150000002540 isothiocyanates Chemical class 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000007858 starting material Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 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
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 235000013312 flour Nutrition 0.000 claims 1
- -1 polymethylene group Polymers 0.000 abstract description 70
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- 238000002844 melting Methods 0.000 description 48
- 230000008018 melting Effects 0.000 description 48
- 239000000243 solution Substances 0.000 description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 229910052938 sodium sulfate Inorganic materials 0.000 description 20
- 235000011152 sodium sulphate Nutrition 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical compound CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 0.000 description 16
- 239000000155 melt Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 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 11
- 239000000203 mixture Substances 0.000 description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 7
- 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 6
- 230000001476 alcoholic effect Effects 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 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 5
- 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
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 4
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- 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 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- JATNWMBUDXLMEO-UHFFFAOYSA-N 1-isothiocyanato-3-methylbutane Chemical compound CC(C)CCN=C=S JATNWMBUDXLMEO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 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
- VHBFEIBMZHEWSX-UHFFFAOYSA-N 2-isothiocyanatopropane Chemical compound CC(C)N=C=S VHBFEIBMZHEWSX-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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 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 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- DEWFPFYAXBRYJB-UHFFFAOYSA-N N-[2-[4-(3-butyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]acetamide Chemical compound C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCC)=N DEWFPFYAXBRYJB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
- 239000004480 active ingredient Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 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 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- CZALJDQHONFVFU-UHFFFAOYSA-N isocyanatocyclopentane Chemical compound O=C=NC1CCCC1 CZALJDQHONFVFU-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- MZSJGCPBOVTKHR-UHFFFAOYSA-N isothiocyanatocyclohexane Chemical compound S=C=NC1CCCCC1 MZSJGCPBOVTKHR-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 2
- 229940117953 phenylisothiocyanate Drugs 0.000 description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- OSBIEFWIIINTNJ-UHFFFAOYSA-N 1,2-dichloro-4-isothiocyanatobenzene Chemical compound ClC1=CC=C(N=C=S)C=C1Cl OSBIEFWIIINTNJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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
- WEIHUEHPZFRVLC-UHFFFAOYSA-N 1-cyclohexyl-3-[2-[4-(2-imino-3-propylimidazolidin-1-yl)sulfonylphenyl]ethyl]urea Chemical compound C1(CCCCC1)NC(NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCC)=N)=O WEIHUEHPZFRVLC-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
- 239000001638 1-isothiocyanatohexane Substances 0.000 description 1
- CEOHWRLZPYDCNW-UHFFFAOYSA-N 2-[4-(2-imino-3-methylimidazolidin-1-yl)sulfonylphenyl]ethanamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C)=N CEOHWRLZPYDCNW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IBWNKMXZXZSQBT-UHFFFAOYSA-N 2-[4-(3-butyl-4-ethyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethanamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(C(C1)CC)CCCC)=N IBWNKMXZXZSQBT-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- IWQRYOWHSNKCPG-UHFFFAOYSA-N 2-bromoethyl(2-methylpropyl)cyanamide Chemical compound BrCCN(C#N)CC(C)C IWQRYOWHSNKCPG-UHFFFAOYSA-N 0.000 description 1
- BWVWYLWQVXEGDZ-UHFFFAOYSA-N 2-bromoethyl(cyclohexyl)cyanamide Chemical compound BrCCN(C#N)C1CCCCC1 BWVWYLWQVXEGDZ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 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
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- IVVUCKOOPIKAFT-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonylpropylurea Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)CCCNC(=O)N IVVUCKOOPIKAFT-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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 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
- FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 1
- YQXLWFHKVJXOQL-UHFFFAOYSA-N 4-isothiocyanatocyclohexene Chemical compound S=C=NC1CCC=CC1 YQXLWFHKVJXOQL-UHFFFAOYSA-N 0.000 description 1
- VGBASMXDKFZLAK-UHFFFAOYSA-N 4-methylimidazolidine Chemical compound CC1CNCN1 VGBASMXDKFZLAK-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RGLOATRSJRPWFV-UHFFFAOYSA-N Cl.Cl.CC1CCC(CC1)N1CCNC1 Chemical compound Cl.Cl.CC1CCC(CC1)N1CCNC1 RGLOATRSJRPWFV-UHFFFAOYSA-N 0.000 description 1
- YDUIKAHKGGZHTG-UHFFFAOYSA-N Cl.Cl.N=C1NCCN1C1CCCC1 Chemical compound Cl.Cl.N=C1NCCN1C1CCCC1 YDUIKAHKGGZHTG-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
- 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 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
- UEVBWFUMZSYXNQ-UHFFFAOYSA-N Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1C=CCCC1)=N Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1C=CCCC1)=N UEVBWFUMZSYXNQ-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-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
- 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 229940100389 Sulfonylurea Drugs 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
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000005840 aryl radicals 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- UKPBEPCQTDRZSE-UHFFFAOYSA-N cyclizine hydrochloride Chemical compound Cl.C1CN(C)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 UKPBEPCQTDRZSE-UHFFFAOYSA-N 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 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
- 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
- 239000008298 dragée Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 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
- 239000005457 ice water Substances 0.000 description 1
- DBDWEKIVKGVZEL-UHFFFAOYSA-N imidazolidine dihydrochloride Chemical compound Cl.Cl.N1CNCC1 DBDWEKIVKGVZEL-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1260271A CH518287A (de) | 1969-08-08 | 1969-08-08 | Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamids |
Applications Claiming Priority (2)
| 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 |
| CH1260271A CH518287A (de) | 1969-08-08 | 1969-08-08 | Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH518287A true CH518287A (de) | 1972-01-31 |
Family
ID=4379702
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1260271A CH518287A (de) | 1969-08-08 | 1969-08-08 | Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamids |
| CH1208569A CH513874A (de) | 1969-08-08 | 1969-08-08 | Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamids |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1208569A CH513874A (de) | 1969-08-08 | 1969-08-08 | Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamids |
Country Status (19)
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1052113A (enrdf_load_stackoverflow) * | 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 NL NL7011391.A patent/NL167423C/xx not_active IP Right Cessation
- 1970-07-31 SE SE10548/70A patent/SE367408B/xx unknown
- 1970-07-31 FI FI702117A patent/FI52461C/fi active
- 1970-07-31 NO NO2971/70A patent/NO124373B/no unknown
- 1970-07-31 DK DK397270AA patent/DK125854B/da not_active IP Right Cessation
- 1970-08-05 US US00061510A patent/US3725430A/en not_active Expired - Lifetime
- 1970-08-07 GB GB3816970A patent/GB1313578A/en not_active Expired
- 1970-08-07 PL PL1970142702A patent/PL80964B1/pl unknown
- 1970-08-07 ZA ZA705468A patent/ZA705468B/xx unknown
- 1970-08-07 DE DE2039419A patent/DE2039419C3/de not_active Expired
- 1970-08-07 BG BG015430A patent/BG17961A3/xx unknown
- 1970-08-07 AT AT722070A patent/AT303750B/de not_active IP Right Cessation
- 1970-08-07 IL IL35080A patent/IL35080A/en unknown
- 1970-08-07 BG BG016384A patent/BG17544A3/xx unknown
- 1970-08-07 IE IE1022/70A patent/IE34445B1/xx unknown
- 1970-08-07 FR FR7029218A patent/FR2068476B1/fr not_active Expired
- 1970-08-07 CA CA090196A patent/CA925089A/en not_active Expired
- 1970-08-07 ES ES382540A patent/ES382540A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO124373B (enrdf_load_stackoverflow) | 1972-04-10 |
| FI52461C (fi) | 1977-09-12 |
| BE754597A (fr) | 1971-02-08 |
| PL80964B1 (enrdf_load_stackoverflow) | 1975-08-30 |
| IE34445B1 (en) | 1975-05-14 |
| NL167423B (nl) | 1981-07-16 |
| ZA705468B (en) | 1971-04-28 |
| DE2039419B2 (de) | 1978-01-05 |
| CH513874A (de) | 1971-10-15 |
| DE2039419C3 (de) | 1978-09-14 |
| ES382540A1 (es) | 1972-12-01 |
| FI52461B (enrdf_load_stackoverflow) | 1977-05-31 |
| IL35080A (en) | 1973-11-28 |
| BG17961A3 (bg) | 1974-03-05 |
| DE2039419A1 (de) | 1971-02-18 |
| BG17544A3 (bg) | 1973-11-10 |
| FR2068476A1 (enrdf_load_stackoverflow) | 1971-08-27 |
| SE367408B (enrdf_load_stackoverflow) | 1974-05-27 |
| FR2068476B1 (enrdf_load_stackoverflow) | 1973-12-21 |
| IL35080A0 (en) | 1970-10-30 |
| CA925089A (en) | 1973-04-24 |
| NL7011391A (enrdf_load_stackoverflow) | 1971-02-10 |
| IE34445L (en) | 1971-02-08 |
| GB1313578A (en) | 1973-04-11 |
| AT303750B (de) | 1972-12-11 |
| NL167423C (nl) | 1981-12-16 |
| DK125854B (da) | 1973-05-14 |
| US3725430A (en) | 1973-04-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2215503A1 (de) | Pyridinderivate und Verfahren zu deren Herstellung | |
| DE2316377C3 (de) | Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen | |
| DE69101141T2 (de) | Neue Guanidinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen. | |
| DE2555789A1 (de) | Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel | |
| DE1445675C3 (de) | Pyridylharnstoffe und Verfahren zu ihrer Herstellung | |
| DE1518874A1 (de) | Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung | |
| DE69632919T2 (de) | Verfahren zur herstellung von 2-chlor-5-chloromethyl-thiazol | |
| DE1912847A1 (de) | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkylbenzolsulfonamids | |
| CH518287A (de) | Verfahren zur Herstellung von neuen Derivaten des p-(Aminoalkyl)-benzolsulfonamids | |
| DE1246722B (de) | Verfahren zur Herstellung von Harnstoffderivaten | |
| DE1443911A1 (de) | Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung | |
| DE1003716B (de) | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen | |
| DE2555685A1 (de) | Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel | |
| DE1695092B2 (de) | N-(4-Sulfonamidophenyl)-a-alkylsuccinimide und deren Salze mit Basen, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen | |
| DE60221660T2 (de) | Bis(trifluoromethyl)hydantoine als intermediate pharmazeutisch aktiver bestandteile | |
| AT221100B (de) | Verfahren zur Herstellung neuer Sulfonylharnstoffe | |
| DE974506C (de) | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen | |
| DE1668168C3 (de) | N1 substituierte N Arylsulfonyl harnstoffe, deren pharmakologisch ver fragliche Salze, Verfahren zu deren Her Stellung und diese enthaltende pharma zeutische Präparate | |
| AT228797B (de) | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen | |
| DE2525851C2 (enrdf_load_stackoverflow) | ||
| CH510031A (de) | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkylbenzolsulfonamids | |
| CH518946A (de) | Verfahren zur Herstellung von neuen Derivaten des p-Amino-alkyl-benzolsulfonamids | |
| DE2043756A1 (de) | Verfahren zur Herstellung von neuen De rivaten des p Aminoalkyl benzolsulfonamids | |
| DE1937972A1 (de) | Neue Pyrrolidinderivate und deren Herstellung | |
| AT290530B (de) | Verfahren zur Herstellung von neuen Imidazolidinderivaten und ihren Salzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |