BE559983A - - Google Patents
Info
- Publication number
- BE559983A BE559983A BE559983DA BE559983A BE 559983 A BE559983 A BE 559983A BE 559983D A BE559983D A BE 559983DA BE 559983 A BE559983 A BE 559983A
- Authority
- BE
- Belgium
- Prior art keywords
- compounds
- reacted
- sulfonyl
- phenyl
- benzene
- Prior art date
Links
- -1 4-phenoxy-phenyl Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 230000000875 corresponding Effects 0.000 claims description 13
- 150000002513 isocyanates Chemical class 0.000 claims description 13
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 claims description 12
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 11
- 239000011780 sodium chloride Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-Dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002357 guanidines Chemical class 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 150000002542 isoureas Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 150000003585 thioureas Chemical class 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000004202 carbamide Substances 0.000 description 23
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 235000013877 carbamide Nutrition 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 239000003610 charcoal Substances 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000001184 potassium carbonate Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 229940093912 Gynecological Sulfonamides Drugs 0.000 description 8
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 8
- 150000003456 sulfonamides Chemical class 0.000 description 8
- 229940026752 topical Sulfonamides Drugs 0.000 description 8
- 210000004369 Blood Anatomy 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- BHHGXPLMPWCGHP-UHFFFAOYSA-N 2-Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- FFLYUXVZEPLMCL-UHFFFAOYSA-N ethylchloranuidyl formate Chemical compound CC[Cl-]OC=O FFLYUXVZEPLMCL-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000002218 hypoglycaemic Effects 0.000 description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical class CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- UAVOCTDYPKOULU-UHFFFAOYSA-N methylchloranuidyl formate Chemical compound C[Cl-]OC=O UAVOCTDYPKOULU-UHFFFAOYSA-N 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- UMIVUZJMDHLJKB-ANTNIJRQSA-N 2-amino-9-(2-hydroxyethoxymethyl)-3H-purin-6-one;[(E)-(3-aminopyridin-2-yl)methylideneamino]thiourea Chemical compound NC(=S)N\N=C\C1=NC=CC=C1N.N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 UMIVUZJMDHLJKB-ANTNIJRQSA-N 0.000 description 2
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical class NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 2
- ZMTSMVZAFDWQRM-UHFFFAOYSA-N 2-phenylethylurea Chemical compound NC(=O)NCCC1=CC=CC=C1 ZMTSMVZAFDWQRM-UHFFFAOYSA-N 0.000 description 2
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropan-1-amine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- FVMLGSFCWGLYET-UHFFFAOYSA-N COC(NS(=O)(=O)C1=CC=C(C=C1)C(C)C)=O Chemical compound COC(NS(=O)(=O)C1=CC=C(C=C1)C(C)C)=O FVMLGSFCWGLYET-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 description 2
- AAYHAFZXFMIUSN-UHFFFAOYSA-N cyclohexanesulfonamide Chemical compound NS(=O)(=O)C1CCCCC1 AAYHAFZXFMIUSN-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 229910003439 heavy metal oxide Inorganic materials 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- KNVDHKOSDVFZTO-UHFFFAOYSA-N methyl N-(4-methylphenyl)sulfonylcarbamate Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 KNVDHKOSDVFZTO-UHFFFAOYSA-N 0.000 description 2
- 231100000324 minimal toxicity Toxicity 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003461 sulfonyl halides Chemical class 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- OXIHBMGOHJFHII-UHFFFAOYSA-N (4-methoxyphenyl)sulfonylurea Chemical compound COC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 OXIHBMGOHJFHII-UHFFFAOYSA-N 0.000 description 1
- XPHSXSCBRHRUND-UHFFFAOYSA-N 1-(1,2,3,4-tetrahydronaphthalen-1-yloxy)-1,2,3,4-tetrahydronaphthalene Chemical compound C12=CC=CC=C2CCCC1OC1C2=CC=CC=C2CCC1 XPHSXSCBRHRUND-UHFFFAOYSA-N 0.000 description 1
- CZHCDTXIWCBSSU-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-(2-phenylethyl)urea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCCC1=CC=CC=C1 CZHCDTXIWCBSSU-UHFFFAOYSA-N 0.000 description 1
- TYCNEYCZTJHLJI-UHFFFAOYSA-N 1-benzyl-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCC1=CC=CC=C1 TYCNEYCZTJHLJI-UHFFFAOYSA-N 0.000 description 1
- VITPICOSHHCBFU-UHFFFAOYSA-N 1-sulfonylguanidine Chemical class NC(=N)N=S(=O)=O VITPICOSHHCBFU-UHFFFAOYSA-N 0.000 description 1
- ILKGEOVHANZEFC-UHFFFAOYSA-N 4-ethoxybenzenesulfonamide Chemical compound CCOC1=CC=C(S(N)(=O)=O)C=C1 ILKGEOVHANZEFC-UHFFFAOYSA-N 0.000 description 1
- MLTGAVXHWSDGIS-UHFFFAOYSA-N 4-ethylbenzenesulfonamide Chemical compound CCC1=CC=C(S(N)(=O)=O)C=C1 MLTGAVXHWSDGIS-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- APHBIZLAPOZWKB-UHFFFAOYSA-N C(C)OC(NS(=O)(=O)C1=CC(=C(C=C1)OC)C)=O Chemical compound C(C)OC(NS(=O)(=O)C1=CC(=C(C=C1)OC)C)=O APHBIZLAPOZWKB-UHFFFAOYSA-N 0.000 description 1
- NSAFKZLBMOZYPV-UHFFFAOYSA-N C1(CCCCC1)S(=O)(=O)NC(=O)OCC Chemical compound C1(CCCCC1)S(=O)(=O)NC(=O)OCC NSAFKZLBMOZYPV-UHFFFAOYSA-N 0.000 description 1
- SMQFZIONCSEEIY-UHFFFAOYSA-N CC(C)N(C(N)=O)S(=O)(=O)C1=CC=CC=C1 Chemical compound CC(C)N(C(N)=O)S(=O)(=O)C1=CC=CC=C1 SMQFZIONCSEEIY-UHFFFAOYSA-N 0.000 description 1
- RKKLYANQCPQFQU-UHFFFAOYSA-N CCC(CC)S(=O)(=O)NC(=O)OCC Chemical compound CCC(CC)S(=O)(=O)NC(=O)OCC RKKLYANQCPQFQU-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N Cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- 206010012601 Diabetes mellitus Diseases 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- VATAIZDYZPAXOX-UHFFFAOYSA-M N-(4-methylphenyl)sulfonylcarbamate Chemical compound CC1=CC=C(S(=O)(=O)NC([O-])=O)C=C1 VATAIZDYZPAXOX-UHFFFAOYSA-M 0.000 description 1
- CDQYMWJDKABVFK-UHFFFAOYSA-N N-(oxomethylidene)cyclohexanesulfonamide Chemical compound O=C=NS(=O)(=O)C1CCCCC1 CDQYMWJDKABVFK-UHFFFAOYSA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N Phenylpropanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- JCTPOQWBYYXZAV-UHFFFAOYSA-N S(=O)(=O)(N)N.C(CCC)OC1=CC=CC=C1 Chemical compound S(=O)(=O)(N)N.C(CCC)OC1=CC=CC=C1 JCTPOQWBYYXZAV-UHFFFAOYSA-N 0.000 description 1
- YTHCJQMYQMGUJK-UHFFFAOYSA-N S(=O)(=O)=NC(=O)OCC.C1=CC=CC=C1 Chemical class S(=O)(=O)=NC(=O)OCC.C1=CC=CC=C1 YTHCJQMYQMGUJK-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 206010044334 Trance Diseases 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004946 alkenylalkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 244000052616 bacterial pathogens Species 0.000 description 1
- YIYZHARUXWKUEN-UHFFFAOYSA-N benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1.NS(=O)(=O)C1=CC=CC=C1 YIYZHARUXWKUEN-UHFFFAOYSA-N 0.000 description 1
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- RJNJWHFSKNJCTB-UHFFFAOYSA-N benzylurea Chemical compound NC(=O)NCC1=CC=CC=C1 RJNJWHFSKNJCTB-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 150000001714 carbamic acid halides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000973 chemotherapeutic Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- HZNQVAOLVRFZBE-UHFFFAOYSA-N ethenylcyclohexane Chemical group C=C[C]1CCCCC1 HZNQVAOLVRFZBE-UHFFFAOYSA-N 0.000 description 1
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl N-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000020828 fasting Nutrition 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000968 intestinal Effects 0.000 description 1
- 230000002147 killing Effects 0.000 description 1
- 230000002045 lasting Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001717 pathogenic Effects 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000286 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
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- IHRQVOBHLWHVSE-UHFFFAOYSA-N sulfamide;toluene Chemical compound NS(N)(=O)=O.CC1=CC=CC=C1 IHRQVOBHLWHVSE-UHFFFAOYSA-N 0.000 description 1
- JMSCRSRHQXBZSD-UHFFFAOYSA-N sulfonylcyanamide Chemical class O=S(=O)=NC#N JMSCRSRHQXBZSD-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07C311/58—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
- 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 |
|---|---|
| BE559983A true BE559983A (cs) |
Family
ID=182459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE559983D BE559983A (cs) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE559983A (cs) |
-
0
- BE BE559983D patent/BE559983A/fr unknown
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