NO122899B - - Google Patents
Download PDFInfo
- Publication number
- NO122899B NO122899B NO150954A NO15095463A NO122899B NO 122899 B NO122899 B NO 122899B NO 150954 A NO150954 A NO 150954A NO 15095463 A NO15095463 A NO 15095463A NO 122899 B NO122899 B NO 122899B
- Authority
- NO
- Norway
- Prior art keywords
- urea
- benzenesulfonyl
- methyl
- melting point
- salt
- Prior art date
Links
- -1 phenoxy-phenyl Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 23
- 150000001412 amines Chemical class 0.000 claims description 20
- 229940100389 Sulfonylurea Drugs 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 77
- 230000008018 melting Effects 0.000 description 77
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 55
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 229910021529 ammonia Inorganic materials 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 18
- YBLWHGQKHHKWRU-UHFFFAOYSA-N 1,3-bis-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 YBLWHGQKHHKWRU-UHFFFAOYSA-N 0.000 description 17
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 17
- 239000004202 carbamide Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- 235000013877 carbamide Nutrition 0.000 description 14
- 230000000875 corresponding effect Effects 0.000 description 14
- 239000000155 melt Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 238000004519 manufacturing process Methods 0.000 description 10
- JTDKEDJPCUTMJL-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JTDKEDJPCUTMJL-UHFFFAOYSA-N 0.000 description 9
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 150000003672 ureas Chemical class 0.000 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 150000003940 butylamines Chemical class 0.000 description 5
- RUUGNIQERAFPSL-UHFFFAOYSA-N ethyl n-(benzenesulfonyl)carbamate Chemical class CCOC(=O)NS(=O)(=O)C1=CC=CC=C1 RUUGNIQERAFPSL-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 5
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-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
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 150000003946 cyclohexylamines Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RIGBPMDIGYBTBJ-UHFFFAOYSA-N glycyclamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RIGBPMDIGYBTBJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003941 n-butylamines Chemical class 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- IHRQVOBHLWHVSE-UHFFFAOYSA-N sulfamide;toluene Chemical compound NS(N)(=O)=O.CC1=CC=CC=C1 IHRQVOBHLWHVSE-UHFFFAOYSA-N 0.000 description 4
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 3
- AAYHAFZXFMIUSN-UHFFFAOYSA-N cyclohexanesulfonamide Chemical compound NS(=O)(=O)C1CCCCC1 AAYHAFZXFMIUSN-UHFFFAOYSA-N 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
- NWIFRSJMWOEKNP-UHFFFAOYSA-N n-[(4-methylphenyl)sulfonylcarbamoyl]acetamide Chemical compound CC(=O)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 NWIFRSJMWOEKNP-UHFFFAOYSA-N 0.000 description 3
- XBJPGFREXQDWPN-UHFFFAOYSA-N n-[(4-methylphenyl)sulfonylcarbamoyl]benzamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC(=O)C1=CC=CC=C1 XBJPGFREXQDWPN-UHFFFAOYSA-N 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- KUIYILOSSGJKHZ-UHFFFAOYSA-N 1,3-bis(benzenesulfonyl)urea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NS(=O)(=O)C1=CC=CC=C1 KUIYILOSSGJKHZ-UHFFFAOYSA-N 0.000 description 2
- RCVYTGONPBOXIF-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)sulfonyl-3-(2-methylpropyl)urea Chemical compound CC1=C(C=C(C=C1)S(=O)(=O)NC(=O)NCC(C)C)Cl RCVYTGONPBOXIF-UHFFFAOYSA-N 0.000 description 2
- BEEJXRDKFNZHFV-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-pentylurea Chemical compound CCCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 BEEJXRDKFNZHFV-UHFFFAOYSA-N 0.000 description 2
- BNZMOMQBYDNFHM-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NS(=O)(=O)C1=CC=CC=C1 BNZMOMQBYDNFHM-UHFFFAOYSA-N 0.000 description 2
- DNIIWANRGRGVRG-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-cyclohexylurea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1CCCCC1 DNIIWANRGRGVRG-UHFFFAOYSA-N 0.000 description 2
- URMFMMLIAIRVRO-UHFFFAOYSA-N 1-butyl-3-(2-methylphenyl)sulfonylurea Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1C URMFMMLIAIRVRO-UHFFFAOYSA-N 0.000 description 2
- FXXMUIOXUGJJKO-UHFFFAOYSA-N 1-butyl-3-(4-propan-2-ylphenyl)sulfonylurea Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C(C)C)C=C1 FXXMUIOXUGJJKO-UHFFFAOYSA-N 0.000 description 2
- HMTRNPUZXPJBFK-UHFFFAOYSA-N 1-cyclohexyl-3-cyclohexylsulfonylurea Chemical compound C1(CCCCC1)S(=O)(=O)NC(=O)NC1CCCCC1 HMTRNPUZXPJBFK-UHFFFAOYSA-N 0.000 description 2
- NGCONVFTEJQTHZ-UHFFFAOYSA-N 1-cyclohexylsulfonyl-3-(2-methylpropyl)urea Chemical compound C1(CCCCC1)S(=O)(=O)NC(=O)NCC(C)C NGCONVFTEJQTHZ-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- MQBITTBZTXUIPN-UHFFFAOYSA-N 2-methylpropylurea Chemical compound CC(C)CNC(N)=O MQBITTBZTXUIPN-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZLWBVTOHKZXGIU-UHFFFAOYSA-N C(C1=CC=CC=C1)S(=O)(=O)NC(=O)NS(=O)(=O)CC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)S(=O)(=O)NC(=O)NS(=O)(=O)CC1=CC=CC=C1 ZLWBVTOHKZXGIU-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IIZVFUFUALIPHV-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NCC(C)C Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NCC(C)C IIZVFUFUALIPHV-UHFFFAOYSA-N 0.000 description 2
- FKOAGWCOPBGKCQ-UHFFFAOYSA-N O=C(NS(C1CCCCC1)(=O)=O)NS(C1CCCCC1)(=O)=O Chemical compound O=C(NS(C1CCCCC1)(=O)=O)NS(C1CCCCC1)(=O)=O FKOAGWCOPBGKCQ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- QOCVOOWVZVIZEO-UHFFFAOYSA-N benzene;sulfamide Chemical class NS(N)(=O)=O.C1=CC=CC=C1 QOCVOOWVZVIZEO-UHFFFAOYSA-N 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- AFOGBLYPWJJVAL-UHFFFAOYSA-N phenbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 AFOGBLYPWJJVAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- LVVLYDLSCDLQMG-UHFFFAOYSA-N 1,1-bis-(4-methylphenyl)sulfonylurea Chemical class Cc1ccc(cc1)S(=O)(=O)N(C(N)=O)S(=O)(=O)c1ccc(C)cc1 LVVLYDLSCDLQMG-UHFFFAOYSA-N 0.000 description 1
- ZRIXMRNZDNXRIH-UHFFFAOYSA-N 1,3-bis[(2-methylphenyl)sulfonyl]urea Chemical compound Cc1ccccc1S(=O)(=O)NC(=O)NS(=O)(=O)c1ccccc1C ZRIXMRNZDNXRIH-UHFFFAOYSA-N 0.000 description 1
- OLSJVTLNNWLLIL-UHFFFAOYSA-N 1,3-disulfonylurea Chemical compound O=S(=O)=NC(=O)N=S(=O)=O OLSJVTLNNWLLIL-UHFFFAOYSA-N 0.000 description 1
- FELQIYPBTCCPET-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-octylurea Chemical compound CCCCCCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 FELQIYPBTCCPET-UHFFFAOYSA-N 0.000 description 1
- VJLQCOHTKNASNE-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 VJLQCOHTKNASNE-UHFFFAOYSA-N 0.000 description 1
- QSLBKVNCTRJJNT-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-propylurea Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 QSLBKVNCTRJJNT-UHFFFAOYSA-N 0.000 description 1
- BBFCVFYDYALSMF-UHFFFAOYSA-N 1-benzylsulfonyl-3-butylurea Chemical compound CCCCNC(=O)NS(=O)(=O)CC1=CC=CC=C1 BBFCVFYDYALSMF-UHFFFAOYSA-N 0.000 description 1
- IGHUGYISOXSCRI-UHFFFAOYSA-N 1-butyl-3-naphthalen-2-ylsulfonylurea Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)NC(=O)NCCCC IGHUGYISOXSCRI-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- TYRVXLIAZXPCND-UHFFFAOYSA-N 1-ethyl-3-(4-methylphenyl)sulfonylurea Chemical compound CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 TYRVXLIAZXPCND-UHFFFAOYSA-N 0.000 description 1
- AQRJDVDPXATDJF-UHFFFAOYSA-N 1-hexyl-3-(4-methylphenyl)sulfonylurea Chemical compound CCCCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 AQRJDVDPXATDJF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HEBTZZBBPUFAFE-UHFFFAOYSA-N 2-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=C=O HEBTZZBBPUFAFE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- AZILYAJHYBTQJL-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)S(=O)(=O)NC(=O)NC1CCCCC1 Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)NC(=O)NC1CCCCC1 AZILYAJHYBTQJL-UHFFFAOYSA-N 0.000 description 1
- LXLUTMFWSPJANZ-UHFFFAOYSA-N C1=C(C=CC=2CCCCC1=2)S(=O)(=O)NC(=O)NCC(C)C Chemical compound C1=C(C=CC=2CCCCC1=2)S(=O)(=O)NC(=O)NCC(C)C LXLUTMFWSPJANZ-UHFFFAOYSA-N 0.000 description 1
- CKFHAFLKWXJTOL-UHFFFAOYSA-N CC(C)C(C=C1)=CC=C1S(NC(NS(C1=CC=C(C(C)C)C=C1)(=O)=O)=O)(=O)=O Chemical compound CC(C)C(C=C1)=CC=C1S(NC(NS(C1=CC=C(C(C)C)C=C1)(=O)=O)=O)(=O)=O CKFHAFLKWXJTOL-UHFFFAOYSA-N 0.000 description 1
- MQBZVZWIESZJLM-UHFFFAOYSA-N CC(C)CNC(NS(C(C=C1)=CC(OC)=C1OC)(=O)=O)=O Chemical compound CC(C)CNC(NS(C(C=C1)=CC(OC)=C1OC)(=O)=O)=O MQBZVZWIESZJLM-UHFFFAOYSA-N 0.000 description 1
- ULZJFSDAGGMEOD-UHFFFAOYSA-N CC(C=C(C=C1)S(NC(NCC2CCCCC2)=O)(=O)=O)=C1OC Chemical compound CC(C=C(C=C1)S(NC(NCC2CCCCC2)=O)(=O)=O)=C1OC ULZJFSDAGGMEOD-UHFFFAOYSA-N 0.000 description 1
- BOAAZJCANBJWST-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC(C1CCCCC1)=O Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC(C1CCCCC1)=O BOAAZJCANBJWST-UHFFFAOYSA-N 0.000 description 1
- GKKQDMAZFBKRLQ-UHFFFAOYSA-N CCCCS(NC(NS(CCCC)(=O)=O)=O)(=O)=O Chemical compound CCCCS(NC(NS(CCCC)(=O)=O)=O)(=O)=O GKKQDMAZFBKRLQ-UHFFFAOYSA-N 0.000 description 1
- CTSIWFGEHNIDOW-UHFFFAOYSA-N COC(NS(=O)(=O)C1=CC(=C(C=C1)C)Cl)=O Chemical compound COC(NS(=O)(=O)C1=CC(=C(C=C1)C)Cl)=O CTSIWFGEHNIDOW-UHFFFAOYSA-N 0.000 description 1
- XTPNRFBDHIQAAI-UHFFFAOYSA-N COC(NS(=O)(=O)C1CCCCC1)=O Chemical compound COC(NS(=O)(=O)C1CCCCC1)=O XTPNRFBDHIQAAI-UHFFFAOYSA-N 0.000 description 1
- GUUWCXQMQNOYLN-UHFFFAOYSA-N COC(NS(C(C=C1)=CC=C1C1=CC=CC=C1)(=O)=O)=O Chemical compound COC(NS(C(C=C1)=CC=C1C1=CC=CC=C1)(=O)=O)=O GUUWCXQMQNOYLN-UHFFFAOYSA-N 0.000 description 1
- QQZGDZQZTKFSSB-UHFFFAOYSA-N COC(NS(C(C=C1)=CC=C1OC1=CC=CC=C1)(=O)=O)=O Chemical compound COC(NS(C(C=C1)=CC=C1OC1=CC=CC=C1)(=O)=O)=O QQZGDZQZTKFSSB-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical class CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- KGINXYFISQQUQW-UHFFFAOYSA-N N-(benzenesulfonyl)carbamoyl chloride Chemical class C1(=CC=CC=C1)S(=O)(=O)NC(=O)Cl KGINXYFISQQUQW-UHFFFAOYSA-N 0.000 description 1
- LOWQEDSQFHBDHF-UHFFFAOYSA-N N-(benzenesulfonylcarbamoyl)acetamide Chemical compound C(C)(=O)NC(=O)NS(=O)(=O)C1=CC=CC=C1 LOWQEDSQFHBDHF-UHFFFAOYSA-N 0.000 description 1
- FTUZUVASIBBRPH-UHFFFAOYSA-N N-[(4-methylphenyl)sulfonylcarbamoyl]butanamide Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC(CCC)=O FTUZUVASIBBRPH-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical class NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 description 1
- DZLLYADKCHLBMB-UHFFFAOYSA-N cyclohexylmethylurea Chemical compound NC(=O)NCC1CCCCC1 DZLLYADKCHLBMB-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ONOVYVJUYZYMCH-UHFFFAOYSA-N ethyl n-(4-acetamidophenyl)sulfonylcarbamate Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 ONOVYVJUYZYMCH-UHFFFAOYSA-N 0.000 description 1
- XSXLCQLOFRENHC-UHFFFAOYSA-N ethyl n-benzylcarbamate Chemical compound CCOC(=O)NCC1=CC=CC=C1 XSXLCQLOFRENHC-UHFFFAOYSA-N 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011551 heat transfer agent Substances 0.000 description 1
- JUVJQIPDVWOVNP-UHFFFAOYSA-N hexylurea Chemical compound CCCCCCNC(N)=O JUVJQIPDVWOVNP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QLMOTGNQTSOZNZ-UHFFFAOYSA-N methyl N-(3,4-dimethoxyphenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC(=C(C=C1)OC)OC)=O QLMOTGNQTSOZNZ-UHFFFAOYSA-N 0.000 description 1
- XWQXWXZSAIORQC-UHFFFAOYSA-N methyl N-(3,4-dimethylphenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC(=C(C=C1)C)C)=O XWQXWXZSAIORQC-UHFFFAOYSA-N 0.000 description 1
- WFDSPGCVYBQWGJ-UHFFFAOYSA-N methyl N-(5,6,7,8-tetrahydronaphthalen-2-ylsulfonyl)carbamate Chemical compound COC(NS(=O)(=O)C1=CC=2CCCCC=2C=C1)=O WFDSPGCVYBQWGJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- ITHCVNUFCWSLGQ-UHFFFAOYSA-N n-(benzenesulfonylcarbamoyl)benzamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC(=O)C1=CC=CC=C1 ITHCVNUFCWSLGQ-UHFFFAOYSA-N 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
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/0802—Preparation methods
- G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/0802—Preparation methods
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK0048292 | 1962-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122899B true NO122899B (en:Method) | 1971-08-30 |
Family
ID=7224885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO150954A NO122899B (en:Method) | 1962-11-24 | 1963-11-23 |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT246565B (en:Method) |
| BE (1) | BE640262A (en:Method) |
| CH (1) | CH438948A (en:Method) |
| DE (1) | DE1472988B2 (en:Method) |
| DK (1) | DK107989C (en:Method) |
| FR (1) | FR1385488A (en:Method) |
| GB (1) | GB1061288A (en:Method) |
| LU (1) | LU44864A1 (en:Method) |
| NL (1) | NL300538A (en:Method) |
| NO (1) | NO122899B (en:Method) |
| SE (1) | SE311282B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004024700A1 (de) * | 2004-05-19 | 2005-12-15 | Clariant Gmbh | Pulverrundkorn |
-
0
- NL NL300538D patent/NL300538A/xx unknown
-
1962
- 1962-11-24 DE DE1472988A patent/DE1472988B2/de active Pending
-
1963
- 1963-11-18 GB GB45453/63A patent/GB1061288A/en not_active Expired
- 1963-11-21 BE BE640262A patent/BE640262A/xx unknown
- 1963-11-21 CH CH1427463A patent/CH438948A/de unknown
- 1963-11-22 DK DK548463AA patent/DK107989C/da active
- 1963-11-22 LU LU44864D patent/LU44864A1/xx unknown
- 1963-11-22 SE SE12932/63A patent/SE311282B/xx unknown
- 1963-11-22 FR FR954672A patent/FR1385488A/fr not_active Expired
- 1963-11-23 NO NO150954A patent/NO122899B/no unknown
- 1963-11-25 AT AT943763A patent/AT246565B/de active
Also Published As
| Publication number | Publication date |
|---|---|
| AT246565B (de) | 1966-04-25 |
| DE1472988A1 (de) | 1969-05-08 |
| DK107989C (da) | 1967-07-24 |
| GB1061288A (en) | 1967-03-08 |
| CH438948A (de) | 1967-06-30 |
| SE311282B (en:Method) | 1969-06-02 |
| DE1472988B2 (de) | 1974-04-04 |
| NL300538A (en:Method) | |
| BE640262A (en:Method) | 1964-05-21 |
| FR1385488A (fr) | 1965-01-15 |
| LU44864A1 (en:Method) | 1965-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK159680B (da) | Cycliske imider til anvendelse ved fremstilling af cycliske aminosyrer | |
| DE1185180B (de) | Verfahren zur Herstellung von Benzolsulfonylharnstoffen | |
| NO151837B (no) | Anordning ved fagverk for bruk under bygging av bygninger og andre konstruksjoner | |
| CN111848463B (zh) | 樟脑磺胺基肟醚类化合物及其制备方法和应用 | |
| US3013072A (en) | Novel process for the production of sulfonylureas | |
| US3005022A (en) | Process for the production of sulfonylureas | |
| DE1518874A1 (de) | Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung | |
| NO122899B (en:Method) | ||
| FI56834C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva bensensulfonylkarbamid | |
| US2990326A (en) | Sulfonyl-urethanes and a process for preparing them | |
| NO129637B (en:Method) | ||
| US3439033A (en) | Benzene-sulfonyl ureas | |
| US3097240A (en) | Novel sulfonyl-ureas | |
| US3202680A (en) | New benzenesulfonyl ureas and process for their manufacture | |
| US3033902A (en) | Arylsulfonylureas | |
| US3108098A (en) | Novel nu-morpholinesulfonyl ureas | |
| CH390907A (de) | Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexylharnstoffen | |
| US3169138A (en) | 1-chloro-n-sulfonyl-formamidines and process for their manufacture | |
| SU435610A1 (en:Method) | ||
| EP0006587B1 (de) | Sulfonylharnstoffe, Verfahren zu ihrer Herstellung sowie pharmazeutische Präparate auf Basis dieser Verbindungen | |
| CH351589A (de) | Verfahren zur Herstellung von Sulfonylharnstoffen | |
| US3136814A (en) | Sulfonylurea derivatives | |
| RU2144915C1 (ru) | Способ получения арилсульфонилмочевин | |
| US3334302A (en) | Dicyclic sulfonylurea compounds | |
| AT203510B (de) | Verfahren zur Herstellung von neuen Sulfonylharnstoffen |