PL69770B1 - - Google Patents
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- PL69770B1 PL69770B1 PL1967120799A PL12079967A PL69770B1 PL 69770 B1 PL69770 B1 PL 69770B1 PL 1967120799 A PL1967120799 A PL 1967120799A PL 12079967 A PL12079967 A PL 12079967A PL 69770 B1 PL69770 B1 PL 69770B1
- Authority
- PL
- Poland
- Prior art keywords
- pattern
- benzenesulfonyl
- beta
- ethyl
- group
- Prior art date
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- -1 dimethylcyclohexyl Chemical group 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 235000013877 carbamide Nutrition 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000003672 ureas Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- PVMBGVAQRSHDBB-UHFFFAOYSA-N benzenesulfonylthiourea Chemical class NC(=S)NS(=O)(=O)C1=CC=CC=C1 PVMBGVAQRSHDBB-UHFFFAOYSA-N 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 210
- 238000001953 recrystallisation Methods 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 23
- 125000003170 phenylsulfonyl group Chemical class C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000004202 carbamide Substances 0.000 description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 239000008280 blood Substances 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FZOOOJPISNODNI-UHFFFAOYSA-N 5-chloro-2-methoxybenzamide Chemical compound COC1=CC=C(Cl)C=C1C(N)=O FZOOOJPISNODNI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KBQJVHYRJXJLPJ-UHFFFAOYSA-N CC(CC1)CC(C)C1NC(NS(C1=CC=C(CCNC(C(C=C(C=C2)Cl)=C2OC)=O)C=C1)(=O)=O)=O Chemical compound CC(CC1)CC(C)C1NC(NS(C1=CC=C(CCNC(C(C=C(C=C2)Cl)=C2OC)=O)C=C1)(=O)=O)=O KBQJVHYRJXJLPJ-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QYUHFVHEYKOZJC-UHFFFAOYSA-N (2,4-dimethylcyclohexyl)urea Chemical compound CC1CCC(NC(N)=O)C(C)C1 QYUHFVHEYKOZJC-UHFFFAOYSA-N 0.000 description 2
- PNZOMJKWVDVPIE-UHFFFAOYSA-N (4,4-dimethylcyclohexyl)urea Chemical compound CC1(C)CCC(NC(N)=O)CC1 PNZOMJKWVDVPIE-UHFFFAOYSA-N 0.000 description 2
- VDTXCHSYBRHTLC-UHFFFAOYSA-N 1,1-diethyl-4-isocyanatocyclohexane Chemical compound CCC1(CC)CCC(N=C=O)CC1 VDTXCHSYBRHTLC-UHFFFAOYSA-N 0.000 description 2
- NAYGFGSBOKLOAY-UHFFFAOYSA-N 4,4-diethylcyclohexan-1-amine Chemical compound CCC1(CC)CCC(N)CC1 NAYGFGSBOKLOAY-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KORMROQYMLPVPO-UHFFFAOYSA-N 2-methoxy-5-methyl-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound COC1=CC=C(C)C=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 KORMROQYMLPVPO-UHFFFAOYSA-N 0.000 description 1
- PKVFZJADFGHKEM-UHFFFAOYSA-N 3,4-dimethylcyclohexan-1-amine Chemical compound CC1CCC(N)CC1C PKVFZJADFGHKEM-UHFFFAOYSA-N 0.000 description 1
- ASWKQZSDUDPQAO-UHFFFAOYSA-N 3-(4,4-dimethylcyclohexyl)-1,1-diphenylurea Chemical compound C1CC(C)(C)CCC1NC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 ASWKQZSDUDPQAO-UHFFFAOYSA-N 0.000 description 1
- BLVFFMPFHWIUGX-UHFFFAOYSA-N 3-methyl-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound CC1=CC=CC(C(=O)NCCC=2C=CC(=CC=2)S(N)(=O)=O)=C1 BLVFFMPFHWIUGX-UHFFFAOYSA-N 0.000 description 1
- KPEWEBCZLHGNCF-UHFFFAOYSA-N 4-chloro-2-methoxy-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound COC1=CC(Cl)=CC=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 KPEWEBCZLHGNCF-UHFFFAOYSA-N 0.000 description 1
- KVWWTCSJLGHLRM-UHFFFAOYSA-N 5-chloro-2-methoxy-n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 KVWWTCSJLGHLRM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BTMCEWPXVDOLNA-UHFFFAOYSA-N C(C)OC1=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N)C=C(C=C1)Cl Chemical compound C(C)OC1=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N)C=C(C=C1)Cl BTMCEWPXVDOLNA-UHFFFAOYSA-N 0.000 description 1
- MQMGIYCPSAEYRL-UHFFFAOYSA-N CC(C)(CC1)CCC1NC(NS(C1=CC=C(CCNC(C(C=C(C=C2)Cl)=C2OC)=O)C=C1)(=O)=O)=O Chemical compound CC(C)(CC1)CCC1NC(NS(C1=CC=C(CCNC(C(C=C(C=C2)Cl)=C2OC)=O)C=C1)(=O)=O)=O MQMGIYCPSAEYRL-UHFFFAOYSA-N 0.000 description 1
- CSAPZDLWQINUHW-UHFFFAOYSA-N CC(C)(CC1)CCC1NC(NS(C1=CC=C(CCNC(C(C=C(C=C2)F)=C2OC)=O)C=C1)(=O)=O)=O Chemical compound CC(C)(CC1)CCC1NC(NS(C1=CC=C(CCNC(C(C=C(C=C2)F)=C2OC)=O)C=C1)(=O)=O)=O CSAPZDLWQINUHW-UHFFFAOYSA-N 0.000 description 1
- MHMKJMSAAXXFIB-UHFFFAOYSA-N CC(C)(CC1)CCC1NC(NS(C1=CC=C(CCNC(C(C=CC(Cl)=C2)=C2OC)=O)C=C1)(=O)=O)=O Chemical compound CC(C)(CC1)CCC1NC(NS(C1=CC=C(CCNC(C(C=CC(Cl)=C2)=C2OC)=O)C=C1)(=O)=O)=O MHMKJMSAAXXFIB-UHFFFAOYSA-N 0.000 description 1
- PEGZLTNLEMBHPB-UHFFFAOYSA-N CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)C(C)=O)=C2OCC)=O)C=C1)(=O)=O)=O Chemical compound CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)C(C)=O)=C2OCC)=O)C=C1)(=O)=O)=O PEGZLTNLEMBHPB-UHFFFAOYSA-N 0.000 description 1
- JBTIKDMEEOWHNF-UHFFFAOYSA-N CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)F)=C2OCC)=O)C=C1)(=O)=O)=O Chemical compound CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)F)=C2OCC)=O)C=C1)(=O)=O)=O JBTIKDMEEOWHNF-UHFFFAOYSA-N 0.000 description 1
- JQPKNQYFRGRBDC-UHFFFAOYSA-N CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)OC)=C2OC)=O)C=C1)(=O)=O)=O Chemical compound CCOC(N(C)S(C1=CC=C(CCNC(C(C=C(C=C2)OC)=C2OC)=O)C=C1)(=O)=O)=O JQPKNQYFRGRBDC-UHFFFAOYSA-N 0.000 description 1
- FBMJVABQSUZJJS-UHFFFAOYSA-N CCOC(N(C)S(C1=CC=C(CCNC(C2=CC(C)=CC(C)=C2)=O)C=C1)(=O)=O)=O Chemical compound CCOC(N(C)S(C1=CC=C(CCNC(C2=CC(C)=CC(C)=C2)=O)C=C1)(=O)=O)=O FBMJVABQSUZJJS-UHFFFAOYSA-N 0.000 description 1
- QIANTASSQORWDD-UHFFFAOYSA-N COC1=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N(C(=O)OCC)C)C=CC=C1 Chemical compound COC1=C(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)N(C(=O)OCC)C)C=CC=C1 QIANTASSQORWDD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 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 description 1
- CEPMBCDLZASDSK-UHFFFAOYSA-N N-[2-[4-(carbamoylsulfamoyl)phenyl]ethyl]-5-chloro-2-methoxybenzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 CEPMBCDLZASDSK-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- QIOOIKAWHHBWFW-UHFFFAOYSA-N acetic acid 2,4-dimethylcyclohexan-1-amine Chemical compound C(C)(=O)O.CC1C(CCC(C1)C)N QIOOIKAWHHBWFW-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 239000012267 brine Substances 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
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- RXFVMUGPHAMQBM-UHFFFAOYSA-N carbonochloridic acid;methanediimine Chemical class N=C=N.OC(Cl)=O RXFVMUGPHAMQBM-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- CRIPLXMKEUSZFI-UHFFFAOYSA-N ethyl N-[4-[2-[(5-chloro-2-ethoxybenzoyl)amino]ethyl]phenyl]sulfonyl-N-methylcarbamate Chemical compound C1=CC(S(=O)(=O)N(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC(Cl)=CC=C1OCC CRIPLXMKEUSZFI-UHFFFAOYSA-N 0.000 description 1
- ADBNAMBPDJQQAK-UHFFFAOYSA-N ethyl n-[4-[2-[(2-methoxy-5-methylbenzoyl)amino]ethyl]phenyl]sulfonyl-n-methylcarbamate Chemical compound C1=CC(S(=O)(=O)N(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC(C)=CC=C1OC ADBNAMBPDJQQAK-UHFFFAOYSA-N 0.000 description 1
- PETZKKYJUCBAIL-UHFFFAOYSA-N ethyl n-[4-[2-[(3-chlorobenzoyl)amino]ethyl]phenyl]sulfonyl-n-methylcarbamate Chemical compound C1=CC(S(=O)(=O)N(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC=CC(Cl)=C1 PETZKKYJUCBAIL-UHFFFAOYSA-N 0.000 description 1
- UPKPLORFQFROOU-UHFFFAOYSA-N ethyl n-methyl-n-[4-[2-[(2-propoxybenzoyl)amino]ethyl]phenyl]sulfonylcarbamate Chemical compound CCCOC1=CC=CC=C1C(=O)NCCC1=CC=C(S(=O)(=O)N(C)C(=O)OCC)C=C1 UPKPLORFQFROOU-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- RIGBPMDIGYBTBJ-UHFFFAOYSA-N glycyclamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RIGBPMDIGYBTBJ-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910003439 heavy metal oxide Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- HCARVZOXHGYEPX-UHFFFAOYSA-N sodium;n-[2-(4-sulfamoylphenyl)ethyl]benzamide Chemical compound [Na].C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)C1=CC=CC=C1 HCARVZOXHGYEPX-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- BWBONKHPVHMQHE-UHFFFAOYSA-N tiocarlide Chemical group C1=CC(OCCC(C)C)=CC=C1NC(=S)NC1=CC=C(OCCC(C)C)C=C1 BWBONKHPVHMQHE-UHFFFAOYSA-N 0.000 description 1
- 229960002171 tiocarlide Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C07C311/59—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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/50—Spiro compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1966F0049329 DE1252201B (de) | 1966-05-28 | 1966-05-28 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL69770B1 true PL69770B1 (enExample) | 1973-08-31 |
Family
ID=7102926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1967120799A PL69770B1 (enExample) | 1966-05-28 | 1967-05-27 |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1252201B (enExample) |
| PL (1) | PL69770B1 (enExample) |
-
1966
- 1966-05-28 DE DE1966F0049329 patent/DE1252201B/de active Granted
-
1967
- 1967-05-27 PL PL1967120799A patent/PL69770B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1252201B (de) | 1967-10-19 |
| DE1252201C2 (enExample) | 1968-05-22 |
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