CH518947A - Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamids - Google Patents
Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamidsInfo
- Publication number
- CH518947A CH518947A CH90972A CH90972A CH518947A CH 518947 A CH518947 A CH 518947A CH 90972 A CH90972 A CH 90972A CH 90972 A CH90972 A CH 90972A CH 518947 A CH518947 A CH 518947A
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- carbon atoms
- ethyl
- imidazolidine
- imino
- Prior art date
Links
- 230000002218 hypoglycaemic effect Effects 0.000 title abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 5
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 2
- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- -1 2-butyramidoethyl Chemical group 0.000 description 59
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 125000001424 substituent group Chemical group 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FFNKZSVHHUBFHT-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].[Na].NC#N FFNKZSVHHUBFHT-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- PVYDJRHPECQXDP-UHFFFAOYSA-N 1-butylimidazolidine Chemical compound CCCCN1CCNC1 PVYDJRHPECQXDP-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000004965 chloroalkyl group Chemical group 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- CXAKSLWZQIMUCN-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]butanamide Chemical compound C1=CC(CCNC(=O)CCC)=CC=C1S(=O)(=O)N1C(=N)N(C2CCCCC2)CC1 CXAKSLWZQIMUCN-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-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
- 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
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- YBDUTMIDSPYXJI-UHFFFAOYSA-N 4-[2-(pentanoylamino)ethyl]benzenesulfonyl chloride Chemical compound CCCCC(=O)NCCC1=CC=C(S(Cl)(=O)=O)C=C1 YBDUTMIDSPYXJI-UHFFFAOYSA-N 0.000 description 1
- UBLDWVTWRHQBGK-UHFFFAOYSA-N 4-[2-(propanoylamino)ethyl]benzenesulfonyl chloride Chemical compound CCC(=O)NCCC1=CC=C(S(Cl)(=O)=O)C=C1 UBLDWVTWRHQBGK-UHFFFAOYSA-N 0.000 description 1
- HFYNRSCRXOUYMU-UHFFFAOYSA-N C(CCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCC1)=N Chemical compound C(CCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCC1)=N HFYNRSCRXOUYMU-UHFFFAOYSA-N 0.000 description 1
- PJGTTXRVROQQIY-UHFFFAOYSA-N C(CCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCCCC1)=N Chemical compound C(CCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCCCC1)=N PJGTTXRVROQQIY-UHFFFAOYSA-N 0.000 description 1
- QXPRRXDUEKXHKK-UHFFFAOYSA-N C(CCCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCC)=N Chemical compound C(CCCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCC)=N QXPRRXDUEKXHKK-UHFFFAOYSA-N 0.000 description 1
- MYIODBQTLJBMON-UHFFFAOYSA-N C1(CCCCC1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N Chemical compound C1(CCCCC1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N MYIODBQTLJBMON-UHFFFAOYSA-N 0.000 description 1
- NPNVRHKBOQXNEV-UHFFFAOYSA-N CC(C)CC(NCCC(C=C1)=CC=C1S(N(CCN1C(C)(C)C)C1=N)(=O)=O)=O Chemical compound CC(C)CC(NCCC(C=C1)=CC=C1S(N(CCN1C(C)(C)C)C1=N)(=O)=O)=O NPNVRHKBOQXNEV-UHFFFAOYSA-N 0.000 description 1
- ZKBSDURCCGFXBH-UHFFFAOYSA-N CCCC(NCCC(C=C1)=CC=C1S(N(CCN1C(C)(C)C)C1=N)(=O)=O)=O Chemical compound CCCC(NCCC(C=C1)=CC=C1S(N(CCN1C(C)(C)C)C1=N)(=O)=O)=O ZKBSDURCCGFXBH-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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- FLNXBHJVHXGRFS-UHFFFAOYSA-N N-(2-phenylethyl)acetamide sulfurochloridic acid Chemical compound S(=O)(=O)(O)Cl.C(C)(=O)NCCC1=CC=CC=C1 FLNXBHJVHXGRFS-UHFFFAOYSA-N 0.000 description 1
- SXYUWQRKXHAAGL-UHFFFAOYSA-N N-[2-[4-(3-cycloheptyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]acetamide Chemical compound C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCCCC1)=N SXYUWQRKXHAAGL-UHFFFAOYSA-N 0.000 description 1
- LYLRVBXQEWRZAV-UHFFFAOYSA-N N-[2-[4-(3-cyclopentyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]cyclohexanecarboxamide Chemical compound C1(CCCCC1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCC1)=N LYLRVBXQEWRZAV-UHFFFAOYSA-N 0.000 description 1
- FMIMKZFOIZJPLQ-UHFFFAOYSA-N N-[2-[4-(3-cyclopentyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]pentanamide Chemical compound C(CCCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCC1)=N FMIMKZFOIZJPLQ-UHFFFAOYSA-N 0.000 description 1
- BDYLAEUWUGVYNG-UHFFFAOYSA-N N-[2-[4-[2-imino-3-(2-methylpropyl)imidazolidin-1-yl]sulfonylphenyl]ethyl]pentanamide Chemical compound C(CCCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N BDYLAEUWUGVYNG-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UNHQZBAKHUKRFS-UHFFFAOYSA-N n-(2-chloroethyl)-2-methylpropan-2-amine;hydrochloride Chemical compound Cl.CC(C)(C)NCCCl UNHQZBAKHUKRFS-UHFFFAOYSA-N 0.000 description 1
- HDGFPODNOGMHTB-UHFFFAOYSA-N n-(2-chloroethyl)cyclohexanamine;hydrochloride Chemical compound Cl.ClCCNC1CCCCC1 HDGFPODNOGMHTB-UHFFFAOYSA-N 0.000 description 1
- WHGGDTWMUDFICJ-UHFFFAOYSA-N n-(2-chloroethyl)propan-1-amine;hydrochloride Chemical compound Cl.CCCNCCCl WHGGDTWMUDFICJ-UHFFFAOYSA-N 0.000 description 1
- WDORQUYYTPJBLE-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)N2C(N(C3CCCCC3)CC2)=N)C=C1 WDORQUYYTPJBLE-UHFFFAOYSA-N 0.000 description 1
- HKVBUWBJODATAO-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]-3-methylbutanamide Chemical compound C1=CC(CCNC(=O)CC(C)C)=CC=C1S(=O)(=O)N1C(=N)N(C2CCCCC2)CC1 HKVBUWBJODATAO-UHFFFAOYSA-N 0.000 description 1
- HTTLBENFCMFRIM-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]benzamide Chemical compound N=C1N(C2CCCCC2)CCN1S(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC=CC=C1 HTTLBENFCMFRIM-UHFFFAOYSA-N 0.000 description 1
- YACZNKYXRHXWGF-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]pentanamide Chemical compound C1=CC(CCNC(=O)CCCC)=CC=C1S(=O)(=O)N1C(=N)N(C2CCCCC2)CC1 YACZNKYXRHXWGF-UHFFFAOYSA-N 0.000 description 1
- XWKAGDYOTYFYPW-UHFFFAOYSA-N n-cyanobenzenesulfonamide Chemical class N#CNS(=O)(=O)C1=CC=CC=C1 XWKAGDYOTYFYPW-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- C07D203/24—Sulfur atoms
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH90972A CH518947A (de) | 1969-09-04 | 1969-09-04 | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH90972A CH518947A (de) | 1969-09-04 | 1969-09-04 | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamids |
| CH1340269A CH519502A (de) | 1969-09-04 | 1969-09-04 | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH518947A true CH518947A (de) | 1972-02-15 |
Family
ID=4392107
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH90972A CH518947A (de) | 1969-09-04 | 1969-09-04 | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamids |
| CH90872A CH518946A (de) | 1969-09-04 | 1969-09-04 | Verfahren zur Herstellung von neuen Derivaten des p-Amino-alkyl-benzolsulfonamids |
| CH1340269A CH519502A (de) | 1969-09-04 | 1969-09-04 | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamids |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH90872A CH518946A (de) | 1969-09-04 | 1969-09-04 | Verfahren zur Herstellung von neuen Derivaten des p-Amino-alkyl-benzolsulfonamids |
| CH1340269A CH519502A (de) | 1969-09-04 | 1969-09-04 | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamids |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT294825B (cs) |
| BG (3) | BG17552A3 (cs) |
| CA (1) | CA920600A (cs) |
| CH (3) | CH518947A (cs) |
| CS (3) | CS171218B2 (cs) |
| ES (3) | ES383346A1 (cs) |
| NL (2) | NL7012728A (cs) |
| NO (1) | NO128913B (cs) |
| PL (1) | PL73360B1 (cs) |
| RO (3) | RO62420A (cs) |
| SE (1) | SE365513B (cs) |
-
1969
- 1969-09-04 CH CH90972A patent/CH518947A/de not_active IP Right Cessation
- 1969-09-04 CH CH90872A patent/CH518946A/de not_active IP Right Cessation
- 1969-09-04 CH CH1340269A patent/CH519502A/de not_active IP Right Cessation
- 1969-09-12 SE SE12576/69A patent/SE365513B/xx unknown
- 1969-09-12 NO NO366169A patent/NO128913B/no unknown
-
1970
- 1970-08-27 NL NL7012728A patent/NL7012728A/xx unknown
- 1970-09-03 ES ES383346A patent/ES383346A1/es not_active Expired
- 1970-09-03 RO RO7023470A patent/RO62420A/ro unknown
- 1970-09-03 CS CS605270A patent/CS171218B2/cs unknown
- 1970-09-03 RO RO6437770A patent/RO56790A/ro unknown
- 1970-09-03 RO RO7023570A patent/RO61494A/ro unknown
- 1970-09-03 CA CA092249A patent/CA920600A/en not_active Expired
- 1970-09-03 PL PL14296970A patent/PL73360B1/pl unknown
- 1970-09-03 BG BG017095A patent/BG17552A3/xx unknown
- 1970-09-03 BG BG017094A patent/BG17551A3/xx unknown
- 1970-09-03 ES ES383347A patent/ES383347A1/es not_active Expired
- 1970-09-03 AT AT802470A patent/AT294825B/de not_active IP Right Cessation
- 1970-09-03 BG BG015602A patent/BG17543A3/xx unknown
- 1970-09-03 ES ES383348A patent/ES383348A1/es not_active Expired
- 1970-09-03 CS CS271770A patent/CS171219B2/cs unknown
- 1970-09-03 CS CS271875A patent/CS171220B2/cs unknown
-
1980
- 1980-06-13 NL NL8003454A patent/NL8003454A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BG17543A3 (bg) | 1973-11-10 |
| SE365513B (cs) | 1974-03-25 |
| ES383348A1 (es) | 1973-01-16 |
| NO128913B (cs) | 1974-01-28 |
| CS171219B2 (cs) | 1976-10-29 |
| RO62420A (fr) | 1978-02-15 |
| BG17552A3 (bg) | 1973-11-10 |
| NL7012728A (cs) | 1971-03-08 |
| PL73360B1 (cs) | 1974-08-30 |
| BG17551A3 (bg) | 1973-11-10 |
| ES383347A1 (es) | 1973-01-16 |
| CS171218B2 (cs) | 1976-10-29 |
| CA920600A (en) | 1973-02-06 |
| CH518946A (de) | 1972-02-15 |
| AT294825B (de) | 1971-12-10 |
| CH519502A (de) | 1972-02-29 |
| RO56790A (cs) | 1974-08-01 |
| CS171220B2 (cs) | 1976-10-29 |
| ES383346A1 (es) | 1973-01-01 |
| NL8003454A (nl) | 1980-10-31 |
| RO61494A (cs) | 1977-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |