BE559530A - - Google Patents
Info
- Publication number
- BE559530A BE559530A BE559530DA BE559530A BE 559530 A BE559530 A BE 559530A BE 559530D A BE559530D A BE 559530DA BE 559530 A BE559530 A BE 559530A
- Authority
- BE
- Belgium
- Prior art keywords
- residue
- formula
- alkyl
- new
- sulfonylurea
- Prior art date
Links
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 16
- -1 aliphatic ester Chemical class 0.000 claims description 15
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 claims description 14
- 239000004202 carbamide Substances 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000005842 heteroatoms Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 235000001014 amino acid Nutrition 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- RISUTSCZAANJJQ-UHFFFAOYSA-N sulfinylurea Chemical compound NC(=O)N=S=O RISUTSCZAANJJQ-UHFFFAOYSA-N 0.000 claims description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229960001230 Asparagine Drugs 0.000 claims 1
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 1
- 239000004473 Threonine Substances 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 235000005772 leucine Nutrition 0.000 claims 1
- 235000006109 methionine Nutrition 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 235000004400 serine Nutrition 0.000 claims 1
- 235000008521 threonine Nutrition 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 235000013877 carbamide Nutrition 0.000 description 13
- 229960000583 Acetic Acid Drugs 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FFKAWVXWZJSAFB-UHFFFAOYSA-N N-(5-sulfamoylpyridin-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=N1 FFKAWVXWZJSAFB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-N-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 4
- 210000004369 Blood Anatomy 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- IQOIAHPAAZJVOX-UHFFFAOYSA-N 1-isocyanato-3-methoxypropane Chemical compound COCCCN=C=O IQOIAHPAAZJVOX-UHFFFAOYSA-N 0.000 description 2
- CYWGSFFHHMQKET-UHFFFAOYSA-N 2-methylsulfanylethanamine Chemical compound CSCCN CYWGSFFHHMQKET-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N N',N'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-Butylamine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M Potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- VZJVWSHVAAUDKD-UHFFFAOYSA-N Potassium permanganate Chemical compound [K+].[O-][Mn](=O)(=O)=O VZJVWSHVAAUDKD-UHFFFAOYSA-N 0.000 description 2
- XXEHHTGAKFJOTP-UHFFFAOYSA-N S(=O)(=O)=NC(NCCCOC)=O Chemical compound S(=O)(=O)=NC(NCCCOC)=O XXEHHTGAKFJOTP-UHFFFAOYSA-N 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- FMMXUAFNDXFJLC-UHFFFAOYSA-N ethoxyethane;urea Chemical compound NC(N)=O.CCOCC FMMXUAFNDXFJLC-UHFFFAOYSA-N 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960001663 sulfanilamide Drugs 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 1
- PTDHBZFQKOXBQJ-UHFFFAOYSA-N 1-(2-isocyanatoethoxy)butane Chemical compound CCCCOCCN=C=O PTDHBZFQKOXBQJ-UHFFFAOYSA-N 0.000 description 1
- MZUZUVFWYAMECF-UHFFFAOYSA-N 1-(3-ethoxypropyl)-3-(4-methylphenyl)sulfonylurea Chemical compound CCOCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 MZUZUVFWYAMECF-UHFFFAOYSA-N 0.000 description 1
- FCXNJMQYOGWZFF-UHFFFAOYSA-N 1-(3-methoxypropyl)-3-(4-methylphenyl)sulfonylurea Chemical compound COCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 FCXNJMQYOGWZFF-UHFFFAOYSA-N 0.000 description 1
- NKRADFUIPKZARM-UHFFFAOYSA-N 1-(furan-2-ylmethyl)-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCC1=CC=CO1 NKRADFUIPKZARM-UHFFFAOYSA-N 0.000 description 1
- ZIRLDYOJRFPDFO-UHFFFAOYSA-N 1-butyl-1-(4-methylphenyl)sulfonylurea Chemical compound CCCCN(C(N)=O)S(=O)(=O)C1=CC=C(C)C=C1 ZIRLDYOJRFPDFO-UHFFFAOYSA-N 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- AQLZTHZLYFFVIJ-UHFFFAOYSA-N 2-(2-aminopropan-2-yl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxopyrimidine-4-carboxamide Chemical compound O=C1N(C)C(C(C)(C)N)=NC(C(=O)NCC=2C=CC(F)=CC=2)=C1O AQLZTHZLYFFVIJ-UHFFFAOYSA-N 0.000 description 1
- YHOOQKRPLXODGK-UHFFFAOYSA-N 2-[2-(diethylamino)ethoxy]ethanamine Chemical compound CCN(CC)CCOCCN YHOOQKRPLXODGK-UHFFFAOYSA-N 0.000 description 1
- XWRLJCNCVXILTN-UHFFFAOYSA-N 2-ethylsulfanylethylurea Chemical compound CCSCCNC(N)=O XWRLJCNCVXILTN-UHFFFAOYSA-N 0.000 description 1
- PBNSGRJZNANHFU-UHFFFAOYSA-N 2-methylsulfanylethylurea Chemical compound CSCCNC(N)=O PBNSGRJZNANHFU-UHFFFAOYSA-N 0.000 description 1
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 1
- KHHKBTRFZTUVRD-UHFFFAOYSA-N 2-propylsulfanylethanamine Chemical compound CCCSCCN KHHKBTRFZTUVRD-UHFFFAOYSA-N 0.000 description 1
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- LBYVZRFDLNAPRC-UHFFFAOYSA-N 2-sulfanylguanidine Chemical compound NC(=N)NS LBYVZRFDLNAPRC-UHFFFAOYSA-N 0.000 description 1
- DQRCIZOJEHRUKN-UHFFFAOYSA-N 3-methylsulfanylpropylurea Chemical compound CSCCCNC(N)=O DQRCIZOJEHRUKN-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- JMUCXULQKPWSTJ-UHFFFAOYSA-N 3-piperidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCCC1 JMUCXULQKPWSTJ-UHFFFAOYSA-N 0.000 description 1
- VPBWZBGZWHDNKL-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCC1 VPBWZBGZWHDNKL-UHFFFAOYSA-N 0.000 description 1
- SZTAVLHJSNLEIC-UHFFFAOYSA-N 4-bromo-N-(oxomethylidene)benzenesulfonamide Chemical compound BrC1=CC=C(S(=O)(=O)N=C=O)C=C1 SZTAVLHJSNLEIC-UHFFFAOYSA-N 0.000 description 1
- JGHDVROWMPBQSR-UHFFFAOYSA-N 4-chloro-N-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=C(S(=O)(=O)N=C=O)C=C1 JGHDVROWMPBQSR-UHFFFAOYSA-N 0.000 description 1
- RPLBYMXKOXFVNR-UHFFFAOYSA-N 6-methylpyridine-3-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=N1 RPLBYMXKOXFVNR-UHFFFAOYSA-N 0.000 description 1
- VDTNNGKXZGSZIP-UHFFFAOYSA-N Carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N N',N'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N N-(p-Tolylsulfonyl)-N'-butylcarbamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N N-Aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N Nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M Sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 241000282485 Vulpes vulpes Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001295 alanines Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 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
- ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 1
- 150000001714 carbamic acid halides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 230000000881 depressing Effects 0.000 description 1
- 230000003009 desulfurizing Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- ARJXIGOIOGJAKR-LURJTMIESA-N ethyl (2S)-2-amino-4-methylsulfanylbutanoate Chemical compound CCOC(=O)[C@@H](N)CCSC ARJXIGOIOGJAKR-LURJTMIESA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- VSNHCAURESNICA-UHFFFAOYSA-N hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
- 229940027318 hydroxyurea Drugs 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N isocyanate Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002741 methionine derivatives Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 125000004430 oxygen atoms Chemical group O* 0.000 description 1
- AZEPYUPSYWCRBG-UHFFFAOYSA-N p-Chlorobenzene sulfonyl urea Chemical compound NC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 AZEPYUPSYWCRBG-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 125000004434 sulfur atoms Chemical group 0.000 description 1
- IUOGNVRKWJWKKK-UHFFFAOYSA-N sulfurochloridic acid;urea Chemical class NC(N)=O.OS(Cl)(=O)=O IUOGNVRKWJWKKK-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE559530A true BE559530A (es) |
Family
ID=182179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE559530D BE559530A (es) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE559530A (es) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3021368A (en) * | 1959-04-22 | 1962-02-13 | Smith Kline French Lab | Substituted trifluoromethylthio- and trifluoromethoxyphenyl sulfonylureas |
| US3140314A (en) * | 1960-07-15 | 1964-07-07 | Cilag Chemie | N-p-toluenesulfonyl-nu'-beta-methylsulfinylethyl urea |
| US3281412A (en) * | 1962-07-24 | 1966-10-25 | Squibb & Sons Inc | Chemical compounds |
-
0
- BE BE559530D patent/BE559530A/fr unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3021368A (en) * | 1959-04-22 | 1962-02-13 | Smith Kline French Lab | Substituted trifluoromethylthio- and trifluoromethoxyphenyl sulfonylureas |
| US3140314A (en) * | 1960-07-15 | 1964-07-07 | Cilag Chemie | N-p-toluenesulfonyl-nu'-beta-methylsulfinylethyl urea |
| US3281412A (en) * | 1962-07-24 | 1966-10-25 | Squibb & Sons Inc | Chemical compounds |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2832146A1 (fr) | Base libre de tamsulosine racemique et ses procedes de preparation | |
| BE559530A (es) | ||
| EP0348257A2 (fr) | Nouveaux dérivés d'(hétéro)aryl diazole, leur procédé de préparation et leur application en thérapeutique | |
| EP0659175B1 (fr) | Derives d'(amino-3 phenyl)-1 ethanesulfonate d'alkylammonium optiquement actifs, leur preparation et leur utilisation | |
| CH594650A5 (en) | Antiinflammatory (1,2)-benzothiazine derivs. prepn. | |
| EP0627403B1 (fr) | Procédé de préparation d'acides hydroxyphénylacétiques | |
| FR2574792A1 (fr) | Procede pour la preparation de derives de pyrrolidine | |
| BE631365A (es) | ||
| BE503348A (es) | ||
| BE565136A (es) | ||
| BE439829A (es) | ||
| BE563006A (es) | ||
| BE442010A (es) | ||
| BE444222A (es) | ||
| BE462035A (es) | ||
| BE562530A (es) | ||
| EP0088849A1 (fr) | Isomères lévogyres de composés benzènesulfonamides N-substitués, leur procédé de préparation et compositions pharmaceutiques les contenant | |
| FR2528832A1 (fr) | Nouveaux derives du benzene, leur preparation et leur utilisation comme medicaments | |
| BE559022A (es) | ||
| BE530601A (es) | ||
| CH617673A5 (en) | Process for the preparation of new guanidine compounds | |
| BE570228A (es) | ||
| BE658698A (es) | ||
| CH304629A (fr) | Procédé de préparation d'une sulfonamide hétérocyclique. | |
| BE569297A (es) |