NO124726B - - Google Patents
Download PDFInfo
- 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
- ZPCHDISCPKZZTR-UHFFFAOYSA-N COC(C=CC=C1)=C1C(NCCC(C=C1)=CC=C1OS(Cl)(=O)=O)=O Chemical compound COC(C=CC=C1)=C1C(NCCC(C=C1)=CC=C1OS(Cl)(=O)=O)=O ZPCHDISCPKZZTR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 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 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 150000001649 bromium compounds Chemical class 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 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
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- IIMGUEXQORZTID-UHFFFAOYSA-N n-{2-[4-(aminosulfonyl)phenyl]ethyl}acetamide Chemical compound CC(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 IIMGUEXQORZTID-UHFFFAOYSA-N 0.000 description 3
- 150000003112 potassium compounds Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- MEUNQQDQAZOSMD-UHFFFAOYSA-N 1-butylimidazolidine dihydrochloride Chemical compound Cl.Cl.C(CCC)N1CNCC1 MEUNQQDQAZOSMD-UHFFFAOYSA-N 0.000 description 2
- YLLIDVIRXLNVIQ-UHFFFAOYSA-N 1-chlorosulfonyloxy-4-[2-(3-methylbutanoylamino)ethyl]benzene Chemical compound C(CC(C)C)(=O)NCCC1=CC=C(C=C1)OS(=O)(=O)Cl YLLIDVIRXLNVIQ-UHFFFAOYSA-N 0.000 description 2
- UCBPXDXAGPAWNF-UHFFFAOYSA-N 1-cycloheptyl-4,5-dihydroimidazol-2-amine hydrochloride Chemical compound Cl.C1(CCCCCC1)N1C(NCC1)=N UCBPXDXAGPAWNF-UHFFFAOYSA-N 0.000 description 2
- LLPCIJIXICNULR-UHFFFAOYSA-N 1-cyclohexyl-4,5-dihydroimidazol-2-amine Chemical compound N=C1NCCN1C1CCCCC1 LLPCIJIXICNULR-UHFFFAOYSA-N 0.000 description 2
- NFKAWBGFIMBUMB-UHFFFAOYSA-N 1-phenylpentan-2-one Chemical compound CCCC(=O)CC1=CC=CC=C1 NFKAWBGFIMBUMB-UHFFFAOYSA-N 0.000 description 2
- SICGKKXMGJHKEL-UHFFFAOYSA-N 1-propyl-4,5-dihydroimidazol-2-amine Chemical compound CCCN1CCN=C1N SICGKKXMGJHKEL-UHFFFAOYSA-N 0.000 description 2
- JUOGRBULLOEKKQ-UHFFFAOYSA-N 2,4-dimethylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C(C)=C1 JUOGRBULLOEKKQ-UHFFFAOYSA-N 0.000 description 2
- IOXOZOPLBFXYLM-UHFFFAOYSA-N 2-(4-nitrophenyl)ethanamine Chemical compound NCCC1=CC=C([N+]([O-])=O)C=C1 IOXOZOPLBFXYLM-UHFFFAOYSA-N 0.000 description 2
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 2
- NZCKTGCKFJDGFD-UHFFFAOYSA-N 2-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Br NZCKTGCKFJDGFD-UHFFFAOYSA-N 0.000 description 2
- LERIVQLRZGYHOY-UHFFFAOYSA-N 2-chloro-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)C1=CC=CC=C1Cl LERIVQLRZGYHOY-UHFFFAOYSA-N 0.000 description 2
- LGZOBXWMMCNBBS-UHFFFAOYSA-N 2-chloroethyl(propan-2-yl)cyanamide Chemical compound ClCCN(C#N)C(C)C LGZOBXWMMCNBBS-UHFFFAOYSA-N 0.000 description 2
- RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 2
- KPUJEMIWIHFVAU-UHFFFAOYSA-N 3-[4-(3-butyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]propan-1-amine dihydrochloride Chemical compound Cl.Cl.NCCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCC)=N KPUJEMIWIHFVAU-UHFFFAOYSA-N 0.000 description 2
- VXQJUAGGPBHYDZ-UHFFFAOYSA-N 3-methyl-n-[2-(4-sulfamoylphenyl)ethyl]butanamide Chemical compound CC(C)CC(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 VXQJUAGGPBHYDZ-UHFFFAOYSA-N 0.000 description 2
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 2
- WEDKXGXYWSNRGL-UHFFFAOYSA-N 4-[2-(3-methylbutanoylamino)ethyl]benzenesulfonyl chloride Chemical compound CC(C)CC(=O)NCCC1=CC=C(S(Cl)(=O)=O)C=C1 WEDKXGXYWSNRGL-UHFFFAOYSA-N 0.000 description 2
- BPBRMDDKQRBMGH-UHFFFAOYSA-N 4-[2-[(2-chlorobenzoyl)amino]ethyl]benzenesulfonyl chloride Chemical compound ClC1=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)Cl)C=CC=C1 BPBRMDDKQRBMGH-UHFFFAOYSA-N 0.000 description 2
- JXFHMBPLIXFVHJ-UHFFFAOYSA-N 4-[2-[(2-methoxybenzoyl)amino]ethyl]benzenesulfonyl chloride Chemical compound COC1=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)Cl)C=CC=C1 JXFHMBPLIXFVHJ-UHFFFAOYSA-N 0.000 description 2
- KJUKTPSEYHPBPZ-UHFFFAOYSA-N 4-chloro-2-[2-(4-chlorosulfonyloxyphenyl)ethylcarbamoyl]-1-methoxybenzene Chemical compound COC1=C(C(=O)NCCC2=CC=C(C=C2)OS(=O)(=O)Cl)C=C(C=C1)Cl KJUKTPSEYHPBPZ-UHFFFAOYSA-N 0.000 description 2
- XVYFIASKNQLXOB-UHFFFAOYSA-N CC(C)N1CCN(C1=N)S(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 Chemical compound CC(C)N1CCN(C1=N)S(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 XVYFIASKNQLXOB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MAUBDQXCYHUOID-UHFFFAOYSA-N ClCCN(C#N)C1CCCCCC1 Chemical compound ClCCN(C#N)C1CCCCCC1 MAUBDQXCYHUOID-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MODKMHXGCGKTLE-UHFFFAOYSA-N N-acetylphenylethylamine Chemical compound CC(=O)NCCC1=CC=CC=C1 MODKMHXGCGKTLE-UHFFFAOYSA-N 0.000 description 2
- MVCPJTDZPHSWDT-UHFFFAOYSA-N O.Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N Chemical compound O.Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N MVCPJTDZPHSWDT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IABUULYQQIHCIL-UHFFFAOYSA-N n-(2-phenylethyl)propanamide Chemical compound CCC(=O)NCCC1=CC=CC=C1 IABUULYQQIHCIL-UHFFFAOYSA-N 0.000 description 2
- JNTOAQVMERFDAK-UHFFFAOYSA-N n-[2-(4-sulfamoylphenyl)ethyl]pentanamide Chemical compound CCCCC(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 JNTOAQVMERFDAK-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- CWSBDVGMKLPIDB-UHFFFAOYSA-N (2-carbonochloridoyl-6-methoxyphenyl) acetate Chemical compound COC1=CC=CC(C(Cl)=O)=C1OC(C)=O CWSBDVGMKLPIDB-UHFFFAOYSA-N 0.000 description 1
- 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
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VEQPSNXGMPYISB-UHFFFAOYSA-N 1-(2-methylcyclohexyl)-4,5-dihydroimidazol-2-amine Chemical compound CC1C(CCCC1)N1C(NCC1)=N VEQPSNXGMPYISB-UHFFFAOYSA-N 0.000 description 1
- FZNOLUXDOUODOM-UHFFFAOYSA-N 1-(2-methylpropyl)-4,5-dihydroimidazol-2-amine Chemical compound CC(C)CN1CCN=C1N FZNOLUXDOUODOM-UHFFFAOYSA-N 0.000 description 1
- NRGZTCYIKMLUBQ-UHFFFAOYSA-N 1-(4-methylcyclohexyl)-4,5-dihydroimidazol-2-amine Chemical compound C1CC(C)CCC1N1C(N)=NCC1 NRGZTCYIKMLUBQ-UHFFFAOYSA-N 0.000 description 1
- ZWPNXULAITYOMP-UHFFFAOYSA-N 1-butylimidazolidine hydrate dihydrochloride Chemical compound O.Cl.Cl.C(CCC)N1CNCC1 ZWPNXULAITYOMP-UHFFFAOYSA-N 0.000 description 1
- DALOHKSWURUHEJ-UHFFFAOYSA-N 1-chlorosulfonyloxy-4-[2-(2-methylbutanoylamino)ethyl]benzene Chemical compound CC(C(=O)NCCC1=CC=C(C=C1)OS(=O)(=O)Cl)CC DALOHKSWURUHEJ-UHFFFAOYSA-N 0.000 description 1
- AZEGBNBVTGQIMZ-UHFFFAOYSA-N 1-chlorosulfonyloxy-4-[2-(pentanoylamino)ethyl]benzene Chemical compound C(CCCC)(=O)NCCC1=CC=C(C=C1)OS(=O)(=O)Cl AZEGBNBVTGQIMZ-UHFFFAOYSA-N 0.000 description 1
- ZMOOPIHFRQOSSQ-UHFFFAOYSA-N 1-cycloheptyl-4,5-dihydroimidazol-2-amine Chemical compound NC1=NCCN1C1CCCCCC1 ZMOOPIHFRQOSSQ-UHFFFAOYSA-N 0.000 description 1
- XLTSCTDVKJVDMO-UHFFFAOYSA-N 1-cyclohexyl-4-methyl-4,5-dihydroimidazol-2-amine hydrochloride Chemical compound Cl.C1(CCCCC1)N1C(NC(C1)C)=N XLTSCTDVKJVDMO-UHFFFAOYSA-N 0.000 description 1
- OGFMAESYTKIOHG-UHFFFAOYSA-N 1-cyclohexylimidazolidine Chemical compound C1NCCN1C1CCCCC1 OGFMAESYTKIOHG-UHFFFAOYSA-N 0.000 description 1
- PEXCBPMLLSAJAP-UHFFFAOYSA-N 1-ethylimidazolidine Chemical compound CCN1CCNC1 PEXCBPMLLSAJAP-UHFFFAOYSA-N 0.000 description 1
- BURKAPSUVIMWKT-UHFFFAOYSA-N 1-methyl-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.CN1CCN=C1N BURKAPSUVIMWKT-UHFFFAOYSA-N 0.000 description 1
- HTVCJMIHPBOLRF-UHFFFAOYSA-N 1-methylcyclohex-3-ene-1-carbonyl chloride Chemical compound ClC(=O)C1(C)CCC=CC1 HTVCJMIHPBOLRF-UHFFFAOYSA-N 0.000 description 1
- FKOPGCJIAFSDAO-UHFFFAOYSA-N 1-methylcyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1(C)CCC=CC1 FKOPGCJIAFSDAO-UHFFFAOYSA-N 0.000 description 1
- STPXIOFWKOIYHX-UHFFFAOYSA-N 1-methylcyclohexane-1-carbonyl chloride Chemical compound ClC(=O)C1(C)CCCCC1 STPXIOFWKOIYHX-UHFFFAOYSA-N 0.000 description 1
- MPDMEQLGLCDAFF-UHFFFAOYSA-N 1-propan-2-yl-4,5-dihydroimidazol-2-amine Chemical compound CC(C)N1CCN=C1N MPDMEQLGLCDAFF-UHFFFAOYSA-N 0.000 description 1
- HFKAHDDXEYJSNB-UHFFFAOYSA-N 1-tert-butylimidazolidine Chemical compound CC(C)(C)N1CCNC1 HFKAHDDXEYJSNB-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
- MGBRPGMQNVRQCG-UHFFFAOYSA-N 2,5-dimethylbenzoyl chloride Chemical compound CC1=CC=C(C)C(C(Cl)=O)=C1 MGBRPGMQNVRQCG-UHFFFAOYSA-N 0.000 description 1
- UMQUIRYNOVNYPA-UHFFFAOYSA-N 2-(4-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C=C1 UMQUIRYNOVNYPA-UHFFFAOYSA-N 0.000 description 1
- JVMHULJEYUQYSH-UHFFFAOYSA-N 2-(4-nitrophenyl)ethylazanium;chloride Chemical compound Cl.NCCC1=CC=C([N+]([O-])=O)C=C1 JVMHULJEYUQYSH-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GLGLYBFHBYVBEM-UHFFFAOYSA-N 2-[4-(3-hexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethanamine Chemical compound NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCCCC)=N GLGLYBFHBYVBEM-UHFFFAOYSA-N 0.000 description 1
- UFQKVVPEAOTAFS-UHFFFAOYSA-N 2-[4-[2-imino-3-(4-methylcyclohexyl)imidazolidin-1-yl]sulfonylphenyl]ethanamine Chemical compound NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCC(CC1)C)=N UFQKVVPEAOTAFS-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- 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
- KVQJVAOMYWTLEO-UHFFFAOYSA-N 2-chlorobutanoyl chloride Chemical compound CCC(Cl)C(Cl)=O KVQJVAOMYWTLEO-UHFFFAOYSA-N 0.000 description 1
- VABYVFZVTIDNOA-UHFFFAOYSA-N 2-cyclohexylacetyl chloride Chemical compound ClC(=O)CC1CCCCC1 VABYVFZVTIDNOA-UHFFFAOYSA-N 0.000 description 1
- KHYVMZMSUZJVMR-UHFFFAOYSA-N 2-methoxy-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound COC1=CC=CC=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 KHYVMZMSUZJVMR-UHFFFAOYSA-N 0.000 description 1
- UDEYSTKYJGEJLU-UHFFFAOYSA-N 2-methyl-n-[2-(4-sulfamoylphenyl)ethyl]butanamide Chemical compound CCC(C)C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 UDEYSTKYJGEJLU-UHFFFAOYSA-N 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- XRPVXVRWIDOORM-UHFFFAOYSA-N 2-methylbutanoyl chloride Chemical compound CCC(C)C(Cl)=O XRPVXVRWIDOORM-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
- QGXMHCMPIAYMGT-UHFFFAOYSA-N 2-phenylbutanoyl chloride Chemical compound CCC(C(Cl)=O)C1=CC=CC=C1 QGXMHCMPIAYMGT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 1
- RGAKSNQOIIYQRM-UHFFFAOYSA-N 3,4-dimethylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1C RGAKSNQOIIYQRM-UHFFFAOYSA-N 0.000 description 1
- ZJIOBDJEKDUUCI-UHFFFAOYSA-N 3,5-dimethylbenzoyl chloride Chemical compound CC1=CC(C)=CC(C(Cl)=O)=C1 ZJIOBDJEKDUUCI-UHFFFAOYSA-N 0.000 description 1
- RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-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
- JUADTOTVJUYCRQ-UHFFFAOYSA-N 3-cyclohexylpropanoyl chloride Chemical compound ClC(=O)CCC1CCCCC1 JUADTOTVJUYCRQ-UHFFFAOYSA-N 0.000 description 1
- GIOFEZBLCNCEBN-UHFFFAOYSA-N 3-methyl-n-(2-phenylethyl)butanamide Chemical compound CC(C)CC(=O)NCCC1=CC=CC=C1 GIOFEZBLCNCEBN-UHFFFAOYSA-N 0.000 description 1
- ZLBXTJOXROCVNL-UHFFFAOYSA-N 4-(3-acetamidopropyl)benzenesulfonyl chloride Chemical compound CC(=O)NCCCC1=CC=C(S(Cl)(=O)=O)C=C1 ZLBXTJOXROCVNL-UHFFFAOYSA-N 0.000 description 1
- WHROKRAUCOMXKF-UHFFFAOYSA-N 4-[2-[(2-methylbenzoyl)amino]ethyl]benzenesulfonyl chloride Chemical compound C=1(C(=CC=CC1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)Cl)C WHROKRAUCOMXKF-UHFFFAOYSA-N 0.000 description 1
- SAJLLULZPJIUMU-UHFFFAOYSA-N 4-[2-[(3,4,5-trimethoxybenzoyl)amino]ethyl]benzenesulfonyl chloride Chemical compound COC=1C=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)Cl)C=C(C1OC)OC SAJLLULZPJIUMU-UHFFFAOYSA-N 0.000 description 1
- XLWQUESMILVIPR-UHFFFAOYSA-N 4-ethoxybenzoyl chloride Chemical compound CCOC1=CC=C(C(Cl)=O)C=C1 XLWQUESMILVIPR-UHFFFAOYSA-N 0.000 description 1
- MROWFEAYAXMMRD-UHFFFAOYSA-N 4-nitro-n-propylaniline Chemical class CCCNC1=CC=C([N+]([O-])=O)C=C1 MROWFEAYAXMMRD-UHFFFAOYSA-N 0.000 description 1
- KVWWTCSJLGHLRM-UHFFFAOYSA-N 5-chloro-2-methoxy-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 KVWWTCSJLGHLRM-UHFFFAOYSA-N 0.000 description 1
- JVLUMHRASWENRU-UHFFFAOYSA-N 5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC=C(Cl)C=C1C(Cl)=O JVLUMHRASWENRU-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- YJUFFSOZORIFAY-UHFFFAOYSA-N Br.C(CCC)N1C(NCC1CC)=N Chemical compound Br.C(CCC)N1C(NCC1CC)=N YJUFFSOZORIFAY-UHFFFAOYSA-N 0.000 description 1
- INHNDDDCRWRZDR-UHFFFAOYSA-N BrCCN(S(=O)(=O)C1=CC=CC=C1)C#N Chemical compound BrCCN(S(=O)(=O)C1=CC=CC=C1)C#N INHNDDDCRWRZDR-UHFFFAOYSA-N 0.000 description 1
- HJWCZPCVUBVZKH-UHFFFAOYSA-N BrCCNC#N Chemical compound BrCCNC#N HJWCZPCVUBVZKH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CTLSYOJZINHABE-UHFFFAOYSA-N C(C(C)(C)C)(=O)NCCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N Chemical compound C(C(C)(C)C)(=O)NCCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N CTLSYOJZINHABE-UHFFFAOYSA-N 0.000 description 1
- PLFUGBZQDSYHEJ-UHFFFAOYSA-N C(C)(=O)NC(CC1=CC=C(C=C1)S(=O)(=O)Cl)C Chemical compound C(C)(=O)NC(CC1=CC=C(C=C1)S(=O)(=O)Cl)C PLFUGBZQDSYHEJ-UHFFFAOYSA-N 0.000 description 1
- RTYWYFOMCZKUCZ-UHFFFAOYSA-N C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)C(CNCCCC)C Chemical compound C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)C(CNCCCC)C RTYWYFOMCZKUCZ-UHFFFAOYSA-N 0.000 description 1
- QZDOIJSJBZTHNW-UHFFFAOYSA-N C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C(CC1=CC=CC=C1)C)=N Chemical compound C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C(CC1=CC=CC=C1)C)=N QZDOIJSJBZTHNW-UHFFFAOYSA-N 0.000 description 1
- BDQQDASOCOVQRP-UHFFFAOYSA-N C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCCC)=N Chemical compound C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCCC)=N BDQQDASOCOVQRP-UHFFFAOYSA-N 0.000 description 1
- YACIMXVSOODTHL-UHFFFAOYSA-N C(C)(=O)NCCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N Chemical compound C(C)(=O)NCCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N YACIMXVSOODTHL-UHFFFAOYSA-N 0.000 description 1
- BKYYCAHIYKBYMS-UHFFFAOYSA-N C(CC(C)C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCC)=N Chemical compound C(CC(C)C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCC)=N BKYYCAHIYKBYMS-UHFFFAOYSA-N 0.000 description 1
- PMONMYFTGFMGQU-UHFFFAOYSA-N C(CC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N(C#N)CCBr Chemical compound C(CC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N(C#N)CCBr PMONMYFTGFMGQU-UHFFFAOYSA-N 0.000 description 1
- BTMMEDVPNNMGKV-UHFFFAOYSA-N C(CC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCCC1)=N Chemical compound C(CC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCCC1)=N BTMMEDVPNNMGKV-UHFFFAOYSA-N 0.000 description 1
- PHWREDBOXVMLAP-UHFFFAOYSA-N C(CC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCC)=N Chemical compound C(CC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCC)=N PHWREDBOXVMLAP-UHFFFAOYSA-N 0.000 description 1
- YQBYGMRUSOXMNH-UHFFFAOYSA-N C(CCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCCCC)=N Chemical compound C(CCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCCCC)=N YQBYGMRUSOXMNH-UHFFFAOYSA-N 0.000 description 1
- MDNNEMNZDSIFNB-UHFFFAOYSA-N C1(CCCCC1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N(C#N)CCBr Chemical compound C1(CCCCC1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N(C#N)CCBr MDNNEMNZDSIFNB-UHFFFAOYSA-N 0.000 description 1
- RUEAHQZSRQAURE-UHFFFAOYSA-N C1(CCCCC1)CCC(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCC)=N Chemical compound C1(CCCCC1)CCC(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCC)=N RUEAHQZSRQAURE-UHFFFAOYSA-N 0.000 description 1
- NWXYBTIJPZFDOV-UHFFFAOYSA-N C=CC(NCCC(C=C1)=CC=C1S(N(CCN1C2CC=CCC2)C1=N)(=O)=O)=O Chemical compound C=CC(NCCC(C=C1)=CC=C1S(N(CCN1C2CC=CCC2)C1=N)(=O)=O)=O NWXYBTIJPZFDOV-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
- WVDWCMJCDLCEJV-UHFFFAOYSA-N CC(NCCC(C=C1)=CC=C1S(N(CCN1C2CC=CCC2)C1=N)(=O)=O)=O Chemical compound CC(NCCC(C=C1)=CC=C1S(N(CCN1C2CC=CCC2)C1=N)(=O)=O)=O WVDWCMJCDLCEJV-UHFFFAOYSA-N 0.000 description 1
- HBUYQFAOHJBBSI-UHFFFAOYSA-N CCC(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1CCN(CC(C)C)C1=N Chemical compound CCC(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1CCN(CC(C)C)C1=N HBUYQFAOHJBBSI-UHFFFAOYSA-N 0.000 description 1
- ONUIPYAWAUVYNJ-UHFFFAOYSA-N CCCCN1C(CC)CN(C1=N)S(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 Chemical compound CCCCN1C(CC)CN(C1=N)S(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 ONUIPYAWAUVYNJ-UHFFFAOYSA-N 0.000 description 1
- MDLRVOSKRUZDKD-UHFFFAOYSA-N CN(C(C)=O)C(CC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCC)=N)C Chemical compound CN(C(C)=O)C(CC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCC)=N)C MDLRVOSKRUZDKD-UHFFFAOYSA-N 0.000 description 1
- QZNOUZQFGHAFPL-UHFFFAOYSA-N COC=1C=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N2C(N(CC2)C2C(CCCC2)C)=N)C=CC=1OC Chemical compound COC=1C=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N2C(N(CC2)C2C(CCCC2)C)=N)C=CC=1OC QZNOUZQFGHAFPL-UHFFFAOYSA-N 0.000 description 1
- QMZNBHGINAJUAJ-UHFFFAOYSA-N Cl.C(CCC)N1C(NC(C1)C)=N Chemical compound Cl.C(CCC)N1C(NC(C1)C)=N QMZNBHGINAJUAJ-UHFFFAOYSA-N 0.000 description 1
- NCCZKTAICSSBSY-UHFFFAOYSA-N Cl.C1(CCCC1)N1C(NCC1)=N Chemical compound Cl.C1(CCCC1)N1C(NCC1)=N NCCZKTAICSSBSY-UHFFFAOYSA-N 0.000 description 1
- YOEPDJWIIKJUDS-UHFFFAOYSA-N Cl.C=1(C(=CC=CC1)C(=O)NCCC1=CC=C(C=C1)N)C Chemical compound Cl.C=1(C(=CC=CC1)C(=O)NCCC1=CC=C(C=C1)N)C YOEPDJWIIKJUDS-UHFFFAOYSA-N 0.000 description 1
- SJIOYKBEGQBSQA-UHFFFAOYSA-N Cl.CC1CCC(CC1)N1C(NCC1)=N Chemical compound Cl.CC1CCC(CC1)N1C(NCC1)=N SJIOYKBEGQBSQA-UHFFFAOYSA-N 0.000 description 1
- XWBHFCQCSPJKDJ-UHFFFAOYSA-N Cl.Cl.N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCCC)=N Chemical compound Cl.Cl.N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCCC)=N XWBHFCQCSPJKDJ-UHFFFAOYSA-N 0.000 description 1
- GSRZPWLSQILHLC-UHFFFAOYSA-N Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCCCC1)=N Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCCCC1)=N GSRZPWLSQILHLC-UHFFFAOYSA-N 0.000 description 1
- KIZWCOOTKIEAEX-UHFFFAOYSA-N Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)C1CCCCC1)=N Chemical compound Cl.Cl.NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)C1CCCCC1)=N KIZWCOOTKIEAEX-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 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
- JMFCJXVIQYEKLR-UHFFFAOYSA-N N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCC)=N Chemical compound N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1C)CCC)=N JMFCJXVIQYEKLR-UHFFFAOYSA-N 0.000 description 1
- PEZDBWBNFPWCBE-UHFFFAOYSA-N N-[2-(4-aminophenyl)ethyl]-5-chloro-2-methoxybenzamide hydrochloride Chemical compound Cl.NC1=CC=C(C=C1)CCNC(C1=C(C=CC(=C1)Cl)OC)=O PEZDBWBNFPWCBE-UHFFFAOYSA-N 0.000 description 1
- NTLPLRVQZQPABO-UHFFFAOYSA-N N-[2-[4-(2-imino-3-propan-2-ylimidazolidin-1-yl)sulfonylphenyl]ethyl]propanamide Chemical compound C(CC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C(C)C)=N NTLPLRVQZQPABO-UHFFFAOYSA-N 0.000 description 1
- MNTHPLSYGFGBLK-UHFFFAOYSA-N N-[2-[4-(3-butyl-2-imino-4-methylimidazolidin-1-yl)sulfonylphenyl]ethyl]acetamide Chemical compound CCCCN1C(C)CN(C1=N)S(=O)(=O)C1=CC=C(CCNC(C)=O)C=C1 MNTHPLSYGFGBLK-UHFFFAOYSA-N 0.000 description 1
- PPXRDBMPQQVPNM-UHFFFAOYSA-N N-[2-[4-(3-butyl-2-imino-4-methylimidazolidin-1-yl)sulfonylphenyl]ethyl]pentanamide Chemical compound C(CCCC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(C(C1)C)CCCC)=N PPXRDBMPQQVPNM-UHFFFAOYSA-N 0.000 description 1
- PXRMKVUCTBQBDK-UHFFFAOYSA-N N-[2-[4-(3-cyclopentyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]acetamide Chemical compound N(C(=O)C)CCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1CCCC1)=N PXRMKVUCTBQBDK-UHFFFAOYSA-N 0.000 description 1
- VJNXIWSALNAUIA-UHFFFAOYSA-N N-[2-[4-(3-hexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]acetamide Chemical compound C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CCCCCC)=N VJNXIWSALNAUIA-UHFFFAOYSA-N 0.000 description 1
- JICJWJRJPDTJMA-UHFFFAOYSA-N N-[2-[4-(aziridin-1-ylsulfonyl)phenyl]ethyl]acetamide Chemical compound C(C)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1CC1 JICJWJRJPDTJMA-UHFFFAOYSA-N 0.000 description 1
- WGVFWWPXLZRONW-UHFFFAOYSA-N N-[2-[4-(aziridin-1-ylsulfonyl)phenyl]ethyl]propanamide Chemical compound C(CC)(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N1CC1 WGVFWWPXLZRONW-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
- YPKBVWZHVTZSPU-UHFFFAOYSA-N N-acetylamphetamine Chemical compound CC(=O)NC(C)CC1=CC=CC=C1 YPKBVWZHVTZSPU-UHFFFAOYSA-N 0.000 description 1
- ALWWQUZWXXTCEP-UHFFFAOYSA-N N-methyl-N-[1-(4-sulfamoylphenyl)propan-2-yl]acetamide Chemical compound CC(CC1=CC=C(C=C1)S(N)(=O)=O)N(C)C(C)=O ALWWQUZWXXTCEP-UHFFFAOYSA-N 0.000 description 1
- GPNMIXDSOVPYMC-UHFFFAOYSA-N NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C(C)C)=N Chemical compound NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C(C)C)=N GPNMIXDSOVPYMC-UHFFFAOYSA-N 0.000 description 1
- FUPXDAKLRDTVOA-UHFFFAOYSA-N NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1C(CCCC1)C)=N Chemical compound NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)C1C(CCCC1)C)=N FUPXDAKLRDTVOA-UHFFFAOYSA-N 0.000 description 1
- RCLDZNSCFBHGGV-UHFFFAOYSA-N NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N Chemical compound NCCC1=CC=C(C=C1)S(=O)(=O)N1C(N(CC1)CC(C)C)=N RCLDZNSCFBHGGV-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- QSZQFXNPVRLTKF-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)CCCNC(C1=CC=CC=C1)=O Chemical class [N+](=O)([O-])C1=CC=C(C=C1)CCCNC(C1=CC=CC=C1)=O QSZQFXNPVRLTKF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 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
- 238000006480 benzoylation reaction Methods 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- XBXHEDNNWSJZPK-UHFFFAOYSA-N chlorosulfonyloxybenzene Chemical compound ClS(=O)(=O)OC1=CC=CC=C1 XBXHEDNNWSJZPK-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- JOGZZTFIGKYTSV-UHFFFAOYSA-N ethylcyanamide Chemical compound CCNC#N JOGZZTFIGKYTSV-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 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 (ru) | 1972-05-29 |
Family
ID=4265567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO69968A NO124726B (ru) | 1968-03-14 | 1969-03-07 |
Country Status (18)
| Country | Link |
|---|---|
| JP (6) | JPS5020068B1 (ru) |
| AT (1) | AT287694B (ru) |
| BE (1) | BE729837A (ru) |
| BG (6) | BG17303A3 (ru) |
| CH (1) | CH505829A (ru) |
| CS (1) | CS166693B2 (ru) |
| DE (1) | DE1912847B2 (ru) |
| DK (1) | DK126327B (ru) |
| FI (1) | FI51179C (ru) |
| FR (1) | FR2003887A1 (ru) |
| GB (1) | GB1269081A (ru) |
| IE (1) | IE32670B1 (ru) |
| IL (1) | IL31802A (ru) |
| MY (1) | MY7500049A (ru) |
| NL (1) | NL144931B (ru) |
| NO (1) | NO124726B (ru) |
| PL (1) | PL79938B1 (ru) |
| SE (1) | SE354863B (ru) |
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 |
| BE755681A (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 |
| 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 (ru) * | 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 NO NO69968A patent/NO124726B/no unknown
- 1969-03-07 DK DK127669AA patent/DK126327B/da not_active IP Right Cessation
- 1969-03-07 SE SE03171/69A patent/SE354863B/xx unknown
- 1969-03-12 NL NL696903831A patent/NL144931B/xx not_active IP Right Cessation
- 1969-03-13 BG BG11840A patent/BG17303A3/xx unknown
- 1969-03-13 DE DE1912847A patent/DE1912847B2/de active Granted
- 1969-03-13 IL IL31802A patent/IL31802A/en unknown
- 1969-03-13 FR FR6907109A patent/FR2003887A1/fr not_active Withdrawn
- 1969-03-13 AT AT248269A patent/AT287694B/de not_active IP Right Cessation
- 1969-03-13 CS CS1829A patent/CS166693B2/cs unknown
- 1969-03-13 PL PL1969132326A patent/PL79938B1/pl unknown
- 1969-03-13 IE IE333/69A patent/IE32670B1/xx unknown
- 1969-03-13 BE BE729837D patent/BE729837A/xx not_active IP Right Cessation
- 1969-03-14 GB GB03512/69A patent/GB1269081A/en not_active Expired
- 1969-06-13 BG BG12440A patent/BG17540A3/xx unknown
- 1969-06-13 BG BG12441A patent/BG21216A3/xx unknown
- 1969-06-13 BG BG12439A patent/BG17304A3/xx unknown
- 1969-06-13 BG BG12442A patent/BG17305A3/xx unknown
- 1969-06-13 BG BG12438A patent/BG17539A3/xx unknown
-
1971
- 1971-02-20 JP JP46007932A patent/JPS5020068B1/ja active Pending
- 1971-02-20 JP JP46007935A patent/JPS5020071B1/ja active Pending
- 1971-02-20 JP JP46007931A patent/JPS5020067B1/ja active Pending
- 1971-02-20 JP JP46007934A patent/JPS5020070B1/ja active Pending
- 1971-02-20 JP JP46007933A patent/JPS5020069B1/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 |
|---|---|
| FI51179C (fi) | 1976-11-10 |
| SE354863B (ru) | 1973-03-26 |
| IE32670B1 (en) | 1973-10-17 |
| IL31802A (en) | 1972-09-28 |
| BG17539A3 (ru) | 1973-11-10 |
| BG21216A3 (ru) | 1976-03-20 |
| NL144931B (nl) | 1975-02-17 |
| CH505829A (de) | 1971-04-15 |
| DE1912847A1 (de) | 1969-10-16 |
| NL6903831A (ru) | 1969-09-16 |
| JPS5020071B1 (ru) | 1975-07-11 |
| BE729837A (ru) | 1969-09-15 |
| MY7500049A (en) | 1975-12-31 |
| JPS5020070B1 (ru) | 1975-07-11 |
| PL79938B1 (en) | 1975-08-30 |
| CS166693B2 (ru) | 1976-03-29 |
| FI51179B (ru) | 1976-08-02 |
| AT287694B (de) | 1971-02-10 |
| JPS5020068B1 (ru) | 1975-07-11 |
| IL31802A0 (en) | 1969-05-28 |
| JPS512468B1 (ru) | 1976-01-26 |
| BG17540A3 (ru) | 1973-11-10 |
| JPS5020067B1 (ru) | 1975-07-11 |
| FR2003887A1 (ru) | 1969-11-14 |
| GB1269081A (en) | 1972-03-29 |
| DE1912847B2 (de) | 1978-09-14 |
| DK126327B (da) | 1973-07-02 |
| BG17304A3 (ru) | 1973-07-25 |
| BG17303A3 (ru) | 1973-07-25 |
| IE32670L (en) | 1969-09-14 |
| JPS5020069B1 (ru) | 1975-07-11 |
| BG17305A3 (ru) | 1973-07-25 |
| DE1912847C3 (ru) | 1979-05-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3454635A (en) | Benzenesulfonyl-ureas and process for their manufacture | |
| CA1190224A (en) | Derivatives of 1,2-diamino-cyclobutene-3,4-dione as potent histamine h.sub.2-antagonists | |
| US3507961A (en) | Benzenesulfonyl ureas as anti-diabetic agents | |
| WO2000047577A1 (en) | Phenyl urea and phenyl thiourea derivatives as orexin receptor antagonists | |
| NO155290B (no) | Analogifremgangsmaate til fremstilling av terapeutisk virksomme sulfonylurinstoffderivater. | |
| NO159136B (no) | Truseinnlegg. | |
| NZ240480A (en) | Aminosulphonyl carbamates and pharmaceutical compositions thereof | |
| HU184259B (en) | Process for producing 2-imidazoline derivatives | |
| NO326650B1 (no) | Substituerte 4-fenyltetrahydroisokinoliner, anvendelse derav for fremstilling av medikamenter, i tillegg til helbredende midler inneholdende samme | |
| DK157862B (da) | Analogifremgangsmaade til fremstilling af imidazolylphenylamidiner eller farmaceutisk acceptable syreadditionssalte deraf | |
| NO124726B (ru) | ||
| NO151837B (no) | Anordning ved fagverk for bruk under bygging av bygninger og andre konstruksjoner | |
| CA1053242A (en) | Heterocyclic guanidine derivatives | |
| NO177993B (no) | Analogifremgangsmåte for fremstilling av terapeutisk aktive amin-derivater | |
| US3406199A (en) | Benzenesulfonyl ureas and process for their manufacture | |
| US3812144A (en) | Derivatives of p-aminoalkylbenzene sulfonamide | |
| WO2005044810A1 (en) | Glyt2 modulators | |
| IE45782B1 (en) | 1-(n-acylcarbamoyl)-2-cyanoziridines | |
| CA1101858A (en) | Naphthalene derivatives | |
| CA1238908A (en) | 2-aminomethylphenol derivatives, a process for their preparation, their use, and pharmaceutical formulations based on these compounds | |
| NO122416B (ru) | ||
| US3538085A (en) | 1-phenylsulfonyl-2-imino-imidazolidines and hexahydropyrimidines | |
| NO312896B1 (no) | Nye 4-(1-piperazinyl)benzosyrederivater, fremgangsmåte for fremstilling derav, samt farmasöytiske preparater som omfatter dem | |
| JPS5988458A (ja) | アミン誘導体およびその塩 | |
| NO774407L (no) | Fremgangsmaate for fremstilling av imidazolderivater |