BE565136A - - Google Patents
Info
- Publication number
- BE565136A BE565136A BE565136DA BE565136A BE 565136 A BE565136 A BE 565136A BE 565136D A BE565136D A BE 565136DA BE 565136 A BE565136 A BE 565136A
- Authority
- BE
- Belgium
- Prior art keywords
- urea
- butyl
- amino
- yield
- nitro
- Prior art date
Links
- -1 sulfonyl carbamides Chemical class 0.000 claims 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 45
- 239000000243 solution Substances 0.000 claims 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 27
- 238000002844 melting Methods 0.000 claims 26
- 230000008018 melting Effects 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 24
- 238000006243 chemical reaction Methods 0.000 claims 23
- 238000003756 stirring Methods 0.000 claims 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 18
- 238000001816 cooling Methods 0.000 claims 18
- 239000004202 carbamide Substances 0.000 claims 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 16
- 239000013078 crystal Substances 0.000 claims 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 15
- 239000000706 filtrate Substances 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 15
- 229940100389 Sulfonylurea Drugs 0.000 claims 13
- 235000013877 carbamide Nutrition 0.000 claims 13
- 239000000047 product Substances 0.000 claims 13
- 235000011121 sodium hydroxide Nutrition 0.000 claims 13
- 239000000155 melt Substances 0.000 claims 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 12
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 11
- 239000002244 precipitate Substances 0.000 claims 10
- 238000001953 recrystallisation Methods 0.000 claims 10
- 238000000967 suction filtration Methods 0.000 claims 10
- 229910021529 ammonia Inorganic materials 0.000 claims 9
- 238000000034 method Methods 0.000 claims 9
- 238000001914 filtration Methods 0.000 claims 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 8
- 238000002360 preparation method Methods 0.000 claims 7
- 239000011541 reaction mixture Substances 0.000 claims 7
- 238000010992 reflux Methods 0.000 claims 7
- 229940124530 sulfonamide Drugs 0.000 claims 7
- 150000003672 ureas Chemical class 0.000 claims 7
- 125000003277 amino group Chemical group 0.000 claims 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 claims 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 6
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 5
- 238000010438 heat treatment Methods 0.000 claims 5
- 230000020477 pH reduction Effects 0.000 claims 5
- 238000007127 saponification reaction Methods 0.000 claims 5
- 239000007858 starting material Substances 0.000 claims 5
- 150000003456 sulfonamides Chemical class 0.000 claims 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- 230000009471 action Effects 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- 239000000463 material Substances 0.000 claims 4
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 4
- 230000008569 process Effects 0.000 claims 4
- 238000000746 purification Methods 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- JBJYRLLCKMAPCW-UHFFFAOYSA-N C(C)(=O)NC=1C=C(C)C=CC=1S(=O)(=O)N(C(=O)OCC)CC Chemical compound C(C)(=O)NC=1C=C(C)C=CC=1S(=O)(=O)N(C(=O)OCC)CC JBJYRLLCKMAPCW-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims 3
- 229940127003 anti-diabetic drug Drugs 0.000 claims 3
- 239000003472 antidiabetic agent Substances 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 239000008280 blood Substances 0.000 claims 3
- 210000004369 blood Anatomy 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 238000010531 catalytic reduction reaction Methods 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 3
- 239000012948 isocyanate Substances 0.000 claims 3
- 150000002513 isocyanates Chemical class 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 238000001556 precipitation Methods 0.000 claims 3
- 230000001603 reducing effect Effects 0.000 claims 3
- 230000009467 reduction Effects 0.000 claims 3
- 238000006722 reduction reaction Methods 0.000 claims 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 3
- 238000005292 vacuum distillation Methods 0.000 claims 3
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 239000007868 Raney catalyst Substances 0.000 claims 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 claims 2
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 claims 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- 238000010411 cooking Methods 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000026030 halogenation Effects 0.000 claims 2
- 238000005658 halogenation reaction Methods 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 230000014759 maintenance of location Effects 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 150000002828 nitro derivatives Chemical class 0.000 claims 2
- 239000012299 nitrogen atmosphere Substances 0.000 claims 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical class [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 150000003673 urethanes Chemical class 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- CAFHTWDNMCYSGD-UHFFFAOYSA-N 1-amino-1-(benzenesulfonyl)urea Chemical compound NC(=O)N(N)S(=O)(=O)C1=CC=CC=C1 CAFHTWDNMCYSGD-UHFFFAOYSA-N 0.000 claims 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims 1
- XCVWCSLKKQOBGY-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonic acid Chemical compound CC(=O)C1=CC(N)=CC=C1S(O)(=O)=O XCVWCSLKKQOBGY-UHFFFAOYSA-N 0.000 claims 1
- YUICMICAJZUZOX-UHFFFAOYSA-N 2-amino-n-(oxomethylidene)benzenesulfonamide Chemical class NC1=CC=CC=C1S(=O)(=O)N=C=O YUICMICAJZUZOX-UHFFFAOYSA-N 0.000 claims 1
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical class NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 claims 1
- CGWBIHLHAGNJCX-UHFFFAOYSA-N 2-butylguanidine Chemical compound CCCCNC(N)=N CGWBIHLHAGNJCX-UHFFFAOYSA-N 0.000 claims 1
- RBJVDTBCPCLEJF-UHFFFAOYSA-N 2-methyl-6-nitrobenzenesulfonamide Chemical compound CC1=CC=CC([N+]([O-])=O)=C1S(N)(=O)=O RBJVDTBCPCLEJF-UHFFFAOYSA-N 0.000 claims 1
- MXSQHPHMAHPHMF-UHFFFAOYSA-N 3,4-dimethyl-5-nitrobenzenesulfonamide Chemical compound CC1=CC(S(N)(=O)=O)=CC([N+]([O-])=O)=C1C MXSQHPHMAHPHMF-UHFFFAOYSA-N 0.000 claims 1
- IQKTYAYBZRHHJI-UHFFFAOYSA-N 3-methoxybutan-1-amine Chemical compound COC(C)CCN IQKTYAYBZRHHJI-UHFFFAOYSA-N 0.000 claims 1
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 claims 1
- JESBYSXPKUMFRV-UHFFFAOYSA-N 4-methoxy-3-nitrobenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1[N+]([O-])=O JESBYSXPKUMFRV-UHFFFAOYSA-N 0.000 claims 1
- AXPAQTAYZOBYFO-UHFFFAOYSA-N C(C)(=O)NC1=C(C=C(C)C=C1)S(=O)(=O)CCNC(=O)OCC Chemical compound C(C)(=O)NC1=C(C=C(C)C=C1)S(=O)(=O)CCNC(=O)OCC AXPAQTAYZOBYFO-UHFFFAOYSA-N 0.000 claims 1
- DSTIJFIFWBRQEG-UHFFFAOYSA-N C(C)(=O)NC1=C(C=C(C=C1)S(=O)(=O)NC(NS(=O)(=O)C1=CC(=C(C=C1)NC(C)=O)Br)=O)Br Chemical compound C(C)(=O)NC1=C(C=C(C=C1)S(=O)(=O)NC(NS(=O)(=O)C1=CC(=C(C=C1)NC(C)=O)Br)=O)Br DSTIJFIFWBRQEG-UHFFFAOYSA-N 0.000 claims 1
- OCSUYUKJJMNODW-UHFFFAOYSA-N CC(N(CCCOC)C(NS(C(C=C1)=CC(Br)=C1N)(=O)=O)=O)=O Chemical compound CC(N(CCCOC)C(NS(C(C=C1)=CC(Br)=C1N)(=O)=O)=O)=O OCSUYUKJJMNODW-UHFFFAOYSA-N 0.000 claims 1
- HYWGNLUFJNXLTC-UHFFFAOYSA-N CC1=C(C=C(C=C1)S(=O)(=O)N(C(=O)OCC)CC)NC(C)=O Chemical compound CC1=C(C=C(C=C1)S(=O)(=O)N(C(=O)OCC)CC)NC(C)=O HYWGNLUFJNXLTC-UHFFFAOYSA-N 0.000 claims 1
- ZWXGKPPRJQWQMG-UHFFFAOYSA-N CC=1C=C(C=C(C=1C)[N+](=O)[O-])S(=O)(=O)N(C(=O)OCC)CC Chemical compound CC=1C=C(C=C(C=1C)[N+](=O)[O-])S(=O)(=O)N(C(=O)OCC)CC ZWXGKPPRJQWQMG-UHFFFAOYSA-N 0.000 claims 1
- AATZEGBSZYCRQZ-UHFFFAOYSA-N CCOC(NCCS(C(C=CC(C)=C1)=C1[N+]([O-])=O)(=O)=O)=O Chemical compound CCOC(NCCS(C(C=CC(C)=C1)=C1[N+]([O-])=O)(=O)=O)=O AATZEGBSZYCRQZ-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 208000013016 Hypoglycemia Diseases 0.000 claims 1
- 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 claims 1
- FAVPVYMUKYDOFS-UHFFFAOYSA-N N-(4-amino-3-bromophenyl)sulfonylacetamide Chemical compound C(C)(=O)NS(=O)(C1=CC(=C(C=C1)N)Br)=O FAVPVYMUKYDOFS-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- BLYNBVFNMSLKHC-UHFFFAOYSA-N NS(C(C1)(C=CC=C1[N+]([O-])=O)Cl)(=O)=O Chemical compound NS(C(C1)(C=CC=C1[N+]([O-])=O)Cl)(=O)=O BLYNBVFNMSLKHC-UHFFFAOYSA-N 0.000 claims 1
- XAORHBINKHJHCC-UHFFFAOYSA-N O-ethyl N-sulfonylcarbamothioate Chemical class S(=O)(=O)=NC(=S)OCC XAORHBINKHJHCC-UHFFFAOYSA-N 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000004153 Potassium bromate Substances 0.000 claims 1
- 102000001708 Protein Isoforms Human genes 0.000 claims 1
- 108010029485 Protein Isoforms Proteins 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- IOCYQFZYDYQPJU-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C)C=CC=1S(=O)(=O)N(C(=O)OCC)CC Chemical compound [N+](=O)([O-])C=1C=C(C)C=CC=1S(=O)(=O)N(C(=O)OCC)CC IOCYQFZYDYQPJU-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 230000021736 acetylation Effects 0.000 claims 1
- 238000006640 acetylation reaction Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 230000001919 adrenal effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 230000008901 benefit Effects 0.000 claims 1
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical class NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 claims 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 235000014633 carbohydrates Nutrition 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 150000001912 cyanamides Chemical class 0.000 claims 1
- 150000003946 cyclohexylamines Chemical class 0.000 claims 1
- 230000020176 deacylation Effects 0.000 claims 1
- 238000005947 deacylation reaction Methods 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 235000005911 diet Nutrition 0.000 claims 1
- 230000037213 diet Effects 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002357 guanidines Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000002198 insoluble material Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 150000002542 isoureas Chemical class 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 231100001252 long-term toxicity Toxicity 0.000 claims 1
- 231100000053 low toxicity Toxicity 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- NVNCJNHFYBSIQX-UHFFFAOYSA-N n-(2-methyl-5-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC(S(N)(=O)=O)=CC=C1C NVNCJNHFYBSIQX-UHFFFAOYSA-N 0.000 claims 1
- ONRWLZAUFFYHMP-UHFFFAOYSA-N n-(4-amino-3-chlorophenyl)sulfonylacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C(Cl)=C1 ONRWLZAUFFYHMP-UHFFFAOYSA-N 0.000 claims 1
- HMMYKPHFTBHHOW-UHFFFAOYSA-N n-(4-amino-3-methylphenyl)sulfonylacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C(C)=C1 HMMYKPHFTBHHOW-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229940127017 oral antidiabetic Drugs 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 235000011837 pasties Nutrition 0.000 claims 1
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 235000019396 potassium bromate Nutrition 0.000 claims 1
- 229940094037 potassium bromate Drugs 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000012047 saturated solution Substances 0.000 claims 1
- 150000003385 sodium Chemical class 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- WVAKABMNNSMCDK-UHFFFAOYSA-N sulfacarbamide Chemical class NC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 WVAKABMNNSMCDK-UHFFFAOYSA-N 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/58—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE565136A true BE565136A (en0) |
Family
ID=185745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE565136D BE565136A (en0) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE565136A (en0) |
-
0
- BE BE565136D patent/BE565136A/fr unknown
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