NO124726B - - Google Patents
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- Publication number
- NO124726B NO124726B NO69968A NO96869A NO124726B NO 124726 B NO124726 B NO 124726B NO 69968 A NO69968 A NO 69968A NO 96869 A NO96869 A NO 96869A NO 124726 B NO124726 B NO 124726B
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- imino
- phenylsulfonyl
- imidazolidine
- chloride
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 19
- 150000007522 mineralic acids Chemical class 0.000 claims description 15
- 150000007524 organic acids Chemical class 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000012546 transfer Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- 125000005039 triarylmethyl group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 333
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 252
- -1 methylene chloride Chemical compound 0.000 description 182
- 239000000243 solution Substances 0.000 description 136
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 85
- 235000011121 sodium hydroxide Nutrition 0.000 description 84
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
- PVYDJRHPECQXDP-UHFFFAOYSA-N 1-butylimidazolidine Chemical compound CCCCN1CCNC1 PVYDJRHPECQXDP-UHFFFAOYSA-N 0.000 description 65
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- 239000003921 oil Substances 0.000 description 47
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 36
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
- 229910052938 sodium sulfate Inorganic materials 0.000 description 30
- 235000011152 sodium sulphate Nutrition 0.000 description 30
- 235000002639 sodium chloride Nutrition 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000001816 cooling Methods 0.000 description 27
- 238000001704 evaporation Methods 0.000 description 26
- 239000007858 starting material Substances 0.000 description 26
- 229920006395 saturated elastomer Polymers 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 23
- 230000008020 evaporation Effects 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000008346 aqueous phase Substances 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- 239000000155 melt Substances 0.000 description 18
- 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 16
- 238000001035 drying Methods 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000012071 phase Substances 0.000 description 16
- 229910052708 sodium Inorganic materials 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 15
- 239000011780 sodium chloride Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- PQZVCRPSQXDXJL-UHFFFAOYSA-N butylcyanamide Chemical compound CCCCNC#N PQZVCRPSQXDXJL-UHFFFAOYSA-N 0.000 description 12
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- 230000001476 alcoholic effect Effects 0.000 description 11
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- 239000012458 free base Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 10
- 239000004540 pour-on Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- BTLIVIIPQUIEES-UHFFFAOYSA-N 2-chloroethyl(cyclohexyl)cyanamide Chemical compound ClCCN(C#N)C1CCCCC1 BTLIVIIPQUIEES-UHFFFAOYSA-N 0.000 description 9
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 238000010790 dilution Methods 0.000 description 9
- 239000012895 dilution Substances 0.000 description 9
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
- QAHCMZKTFRUHKX-UHFFFAOYSA-N Cl.C(CCC)N1C(=NCC1)N Chemical compound Cl.C(CCC)N1C(=NCC1)N QAHCMZKTFRUHKX-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 238000006243 chemical reaction Methods 0.000 description 8
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 8
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 8
- VSHNWNOZERVVNK-UHFFFAOYSA-N 4-(2-acetamidoethyl)benzenesulfonyl chloride Chemical compound CC(=O)NCCC1=CC=C(S(Cl)(=O)=O)C=C1 VSHNWNOZERVVNK-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- HLOVCHVXIIXUHK-UHFFFAOYSA-N butyl(2-chloroethyl)cyanamide Chemical compound ClCCN(C#N)CCCC HLOVCHVXIIXUHK-UHFFFAOYSA-N 0.000 description 6
- 229960003280 cupric chloride Drugs 0.000 description 6
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- GCWFLQIRNPJFIC-UHFFFAOYSA-N 1-cyclohexyl-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.N=C1NCCN1C1CCCCC1 GCWFLQIRNPJFIC-UHFFFAOYSA-N 0.000 description 5
- 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 5
- VLSUMNVKYSAGLX-UHFFFAOYSA-N 4-[2-[(3-methoxybenzoyl)amino]ethyl]benzenesulfonyl chloride Chemical compound COC=1C=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)Cl)C=CC1 VLSUMNVKYSAGLX-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- MRJYEIYPZFWJLC-UHFFFAOYSA-N n-[2-(4-sulfamoylphenyl)ethyl]butanamide Chemical compound CCCC(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 MRJYEIYPZFWJLC-UHFFFAOYSA-N 0.000 description 5
- 150000002828 nitro derivatives Chemical class 0.000 description 5
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- FIZLLOWJEFBXDX-UHFFFAOYSA-N 1-(2-acetamidoethyl)-4-chlorosulfonyloxybenzene Chemical compound C(C)(=O)NCCC1=CC=C(C=C1)OS(=O)(=O)Cl FIZLLOWJEFBXDX-UHFFFAOYSA-N 0.000 description 4
- OJJUIUGRFDCUHE-UHFFFAOYSA-N 1-[2-(butanoylamino)ethyl]-4-chlorosulfonyloxybenzene Chemical compound C(CCC)(=O)NCCC1=CC=C(C=C1)OS(=O)(=O)Cl OJJUIUGRFDCUHE-UHFFFAOYSA-N 0.000 description 4
- QYPYMNLNXFYDHW-UHFFFAOYSA-N 1-chlorosulfonyloxy-4-[2-(propanoylamino)ethyl]benzene Chemical compound C(CC)(=O)NCCC1=CC=C(C=C1)OS(=O)(=O)Cl QYPYMNLNXFYDHW-UHFFFAOYSA-N 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 4
- QRBBHPXLBAWRQG-UHFFFAOYSA-N 2-chloroethyl(cyclopentyl)cyanamide Chemical compound ClCCN(C#N)C1CCCC1 QRBBHPXLBAWRQG-UHFFFAOYSA-N 0.000 description 4
- FKSKVGHKDDXOPL-UHFFFAOYSA-N 3-[4-[2-imino-3-(2-methylpropyl)imidazolidin-1-yl]sulfonylphenyl]propan-1-amine dihydrochloride Chemical compound Cl.Cl.NCCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N FKSKVGHKDDXOPL-UHFFFAOYSA-N 0.000 description 4
- LKOUQIVOCUNXJM-UHFFFAOYSA-N 4-(2-formamidoethyl)benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(CCNC=O)C=C1 LKOUQIVOCUNXJM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ISEOIHWYBXTSTC-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzenesulfonyl chloride Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(Cl)(=O)=O)C=C1 ISEOIHWYBXTSTC-UHFFFAOYSA-N 0.000 description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 4
- 230000002218 hypoglycaemic effect Effects 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 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 3
- VFGUNEPUWQZLPW-UHFFFAOYSA-N 1-cyclopentyl-4,5-dihydroimidazol-2-amine Chemical compound NC1=NCCN1C1CCCC1 VFGUNEPUWQZLPW-UHFFFAOYSA-N 0.000 description 3
- XPWZNVWRBSAUMG-UHFFFAOYSA-N 1-propyl-4,5-dihydroimidazol-2-amine hydrochloride Chemical compound Cl.C(CC)N1C(NCC1)=N XPWZNVWRBSAUMG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- DTXCPFPGOGPELE-UHFFFAOYSA-N 2-chloroethyl(2-methylpropyl)cyanamide Chemical compound ClCCN(C#N)CC(C)C DTXCPFPGOGPELE-UHFFFAOYSA-N 0.000 description 3
- IMMWXRJMBHEVIP-UHFFFAOYSA-N 2-chloroethyl(propyl)cyanamide Chemical compound ClCCN(C#N)CCC IMMWXRJMBHEVIP-UHFFFAOYSA-N 0.000 description 3
- RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 3
- CRADEZLCQMNNCF-UHFFFAOYSA-N 4-(3-aminopropyl)benzenesulfonamide;hydrochloride Chemical compound Cl.NCCCC1=CC=C(S(N)(=O)=O)C=C1 CRADEZLCQMNNCF-UHFFFAOYSA-N 0.000 description 3
- WFMRQGSULRIJPM-UHFFFAOYSA-N 4-[2-(butanoylamino)ethyl]benzenesulfonyl chloride Chemical compound CCCC(=O)NCCC1=CC=C(S(Cl)(=O)=O)C=C1 WFMRQGSULRIJPM-UHFFFAOYSA-N 0.000 description 3
- POHYRSNCNRDCQV-UHFFFAOYSA-N 4-[2-(cyclohexanecarbonylamino)ethyl]benzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1CCNC(=O)C1CCCCC1 POHYRSNCNRDCQV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000000543 intermediate Substances 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
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- ZIOZMZMOOGVIFG-UHFFFAOYSA-N n-(2-phenylethyl)butanamide Chemical compound CCCC(=O)NCCC1=CC=CC=C1 ZIOZMZMOOGVIFG-UHFFFAOYSA-N 0.000 description 1
- NOOOMJZHMKSKBF-UHFFFAOYSA-N n-(2-phenylethyl)formamide Chemical compound O=CNCCC1=CC=CC=C1 NOOOMJZHMKSKBF-UHFFFAOYSA-N 0.000 description 1
- RBPXCUDFQLFKPO-UHFFFAOYSA-N n-(2-phenylethyl)pentanamide Chemical compound CCCCC(=O)NCCC1=CC=CC=C1 RBPXCUDFQLFKPO-UHFFFAOYSA-N 0.000 description 1
- ZXNZKPHZMIMFGR-UHFFFAOYSA-N n-[2-(4-sulfamoylphenyl)ethyl]propanamide Chemical compound CCC(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 ZXNZKPHZMIMFGR-UHFFFAOYSA-N 0.000 description 1
- OEEYJFMYYIFSCF-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)N2C(N(C3CCCCC3)CC2)=N)C=C1 OEEYJFMYYIFSCF-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
- MJHARKXTXVHVIH-UHFFFAOYSA-N n-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]formamide Chemical compound N=C1N(C2CCCCC2)CCN1S(=O)(=O)C1=CC=C(CCNC=O)C=C1 MJHARKXTXVHVIH-UHFFFAOYSA-N 0.000 description 1
- CFRFZQGIJFUAIY-UHFFFAOYSA-N n-[3-(4-aminophenyl)propyl]benzamide Chemical class C1=CC(N)=CC=C1CCCNC(=O)C1=CC=CC=C1 CFRFZQGIJFUAIY-UHFFFAOYSA-N 0.000 description 1
- VRPBBQHVIQRQDQ-UHFFFAOYSA-N n-methyl-n-(3-phenylpropyl)acetamide Chemical compound CC(=O)N(C)CCCC1=CC=CC=C1 VRPBBQHVIQRQDQ-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 238000007911 parenteral administration Methods 0.000 description 1
- CWHFDTWZHFRTAB-UHFFFAOYSA-N phenyl cyanate Chemical compound N#COC1=CC=CC=C1 CWHFDTWZHFRTAB-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water 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
- UFIRKHUKHAOTKH-UHFFFAOYSA-N tert-butyl(2-chloroethyl)cyanamide Chemical compound CC(C)(C)N(C#N)CCCl UFIRKHUKHAOTKH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000016788 valerian Nutrition 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH388468A CH505829A (de) | 1968-03-14 | 1968-03-14 | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkylbenzolsulfonamids |
Publications (1)
Publication Number | Publication Date |
---|---|
NO124726B true NO124726B (cs) | 1972-05-29 |
Family
ID=4265567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO69968A NO124726B (cs) | 1968-03-14 | 1969-03-07 |
Country Status (18)
Country | Link |
---|---|
JP (6) | JPS5020069B1 (cs) |
AT (1) | AT287694B (cs) |
BE (1) | BE729837A (cs) |
BG (6) | BG17303A3 (cs) |
CH (1) | CH505829A (cs) |
CS (1) | CS166693B2 (cs) |
DE (1) | DE1912847B2 (cs) |
DK (1) | DK126327B (cs) |
FI (1) | FI51179C (cs) |
FR (1) | FR2003887A1 (cs) |
GB (1) | GB1269081A (cs) |
IE (1) | IE32670B1 (cs) |
IL (1) | IL31802A (cs) |
MY (1) | MY7500049A (cs) |
NL (1) | NL144931B (cs) |
NO (1) | NO124726B (cs) |
PL (1) | PL79938B1 (cs) |
SE (1) | SE354863B (cs) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE754597A (fr) * | 1969-08-08 | 1971-02-08 | Geigy Ag J R | Alkyl-benzene-sulfonamides et medicaments contenant de tels composes |
BE755684A (fr) * | 1969-09-04 | 1971-03-03 | Geigy Ag J R | P-aminoalkyl-benzene-sulfonamides et medicaments contenant de tels composes |
BE755686A (fr) * | 1969-09-04 | 1971-03-03 | Geigy Ag J R | Aminoalkyl-benzene-sulfonamides et medicaments renfermant de tels composes |
BE755681A (fr) * | 1969-09-04 | 1971-03-03 | Geigy Ag J R | P-aminoalkyl-benzene-sulfonamides et medicaments contenant de tels composes |
BE755682A (fr) * | 1969-09-04 | 1971-03-03 | Geigy Ag J R | P-aminoalkyl-benzene-sulfonamides et medicaments contenant de tels composes |
US4591597A (en) * | 1983-04-05 | 1986-05-27 | Ciba-Geigy Corporation | Antidiabetic iminosulphonamides |
US6335445B1 (en) * | 1997-03-24 | 2002-01-01 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1224812A (fr) * | 1956-12-28 | 1960-06-27 | Geigy Ag J R | Nouveaux 2-imino-1.3-di-n-hétérocycles et leur procédé de préparation |
GB1052113A (cs) * | 1963-02-07 |
-
1968
- 1968-03-14 CH CH388468A patent/CH505829A/de not_active IP Right Cessation
-
1969
- 1969-03-05 FI FI690664A patent/FI51179C/fi active
- 1969-03-07 SE SE03171/69A patent/SE354863B/xx unknown
- 1969-03-07 NO NO69968A patent/NO124726B/no unknown
- 1969-03-07 DK DK127669AA patent/DK126327B/da not_active IP Right Cessation
- 1969-03-12 NL NL696903831A patent/NL144931B/xx not_active IP Right Cessation
- 1969-03-13 DE DE1912847A patent/DE1912847B2/de active Granted
- 1969-03-13 AT AT248269A patent/AT287694B/de not_active IP Right Cessation
- 1969-03-13 FR FR6907109A patent/FR2003887A1/fr not_active Withdrawn
- 1969-03-13 BE BE729837D patent/BE729837A/xx not_active IP Right Cessation
- 1969-03-13 CS CS1829A patent/CS166693B2/cs unknown
- 1969-03-13 IE IE333/69A patent/IE32670B1/xx unknown
- 1969-03-13 PL PL1969132326A patent/PL79938B1/pl unknown
- 1969-03-13 BG BG011840A patent/BG17303A3/xx unknown
- 1969-03-13 IL IL31802A patent/IL31802A/en unknown
- 1969-03-14 GB GB03512/69A patent/GB1269081A/en not_active Expired
- 1969-06-13 BG BG12441A patent/BG21216A3/xx unknown
- 1969-06-13 BG BG012442A patent/BG17305A3/xx unknown
- 1969-06-13 BG BG012439A patent/BG17304A3/xx unknown
- 1969-06-13 BG BG012440A patent/BG17540A3/xx unknown
- 1969-06-13 BG BG012438A patent/BG17539A3/xx unknown
-
1971
- 1971-02-20 JP JP46007933A patent/JPS5020069B1/ja active Pending
- 1971-02-20 JP JP46007935A patent/JPS5020071B1/ja active Pending
- 1971-02-20 JP JP46007934A patent/JPS5020070B1/ja active Pending
- 1971-02-20 JP JP46007932A patent/JPS5020068B1/ja active Pending
- 1971-02-20 JP JP46007931A patent/JPS5020067B1/ja active Pending
-
1975
- 1975-01-16 JP JP50006498A patent/JPS512468B1/ja active Pending
- 1975-12-30 MY MY49/75A patent/MY7500049A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
FR2003887A1 (cs) | 1969-11-14 |
BG17540A3 (bg) | 1973-11-10 |
BE729837A (cs) | 1969-09-15 |
IE32670B1 (en) | 1973-10-17 |
JPS512468B1 (cs) | 1976-01-26 |
JPS5020071B1 (cs) | 1975-07-11 |
PL79938B1 (en) | 1975-08-30 |
BG17539A3 (bg) | 1973-11-10 |
GB1269081A (en) | 1972-03-29 |
DE1912847C3 (cs) | 1979-05-23 |
DE1912847B2 (de) | 1978-09-14 |
IL31802A0 (en) | 1969-05-28 |
JPS5020068B1 (cs) | 1975-07-11 |
AT287694B (de) | 1971-02-10 |
MY7500049A (en) | 1975-12-31 |
IL31802A (en) | 1972-09-28 |
SE354863B (cs) | 1973-03-26 |
FI51179C (fi) | 1976-11-10 |
IE32670L (en) | 1969-09-14 |
DE1912847A1 (de) | 1969-10-16 |
BG17303A3 (bg) | 1973-07-25 |
NL144931B (nl) | 1975-02-17 |
JPS5020069B1 (cs) | 1975-07-11 |
JPS5020070B1 (cs) | 1975-07-11 |
NL6903831A (cs) | 1969-09-16 |
FI51179B (cs) | 1976-08-02 |
BG17305A3 (bg) | 1973-07-25 |
CS166693B2 (cs) | 1976-03-29 |
JPS5020067B1 (cs) | 1975-07-11 |
DK126327B (da) | 1973-07-02 |
BG17304A3 (bg) | 1973-07-25 |
CH505829A (de) | 1971-04-15 |
BG21216A3 (cs) | 1976-03-20 |
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