SE201887C1 - - Google Patents
Info
- Publication number
- SE201887C1 SE201887C1 SE201887DA SE201887C1 SE 201887 C1 SE201887 C1 SE 201887C1 SE 201887D A SE201887D A SE 201887DA SE 201887 C1 SE201887 C1 SE 201887C1
- Authority
- SE
- Sweden
- Prior art keywords
- carbon atoms
- benzenesulfonyl
- solution
- radical
- toluenesulfonyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000008280 blood Substances 0.000 claims description 15
- 210000004369 blood Anatomy 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical compound CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- 230000010030 glucose lowering effect Effects 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000005587 carbonate group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- -1 p-toluenesulfonyl Chemical group 0.000 description 17
- 159000000000 sodium salts Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 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 11
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- SETDGFFRAQQPBH-UHFFFAOYSA-N ethyl N-butyl-N-(4-methylphenyl)sulfonylcarbamate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC)C SETDGFFRAQQPBH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- IIHYYTZVOBOZSG-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC)C.[Na] Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC)C.[Na] IIHYYTZVOBOZSG-UHFFFAOYSA-N 0.000 description 3
- YPMFGPMFQZTXJD-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)N(C(=O)OCC)CCCC YPMFGPMFQZTXJD-UHFFFAOYSA-N 0.000 description 3
- CPWDGULOUMCELT-UHFFFAOYSA-N C1=C(C=CC=2CCCCC12)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound C1=C(C=CC=2CCCCC12)S(=O)(=O)N(C(=O)OCC)CCCC CPWDGULOUMCELT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- WTWDVBBHANGJOK-UHFFFAOYSA-N ethyl N-(4-methylphenyl)sulfonyl-N-(2-methylpropyl)carbamate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CC(C)C)C WTWDVBBHANGJOK-UHFFFAOYSA-N 0.000 description 3
- XGTNRRPHBDIQBP-UHFFFAOYSA-N ethyl N-(4-methylphenyl)sulfonyl-N-(3-phenylpropyl)carbamate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC1=CC=CC=C1 XGTNRRPHBDIQBP-UHFFFAOYSA-N 0.000 description 3
- CXLBYPJSAWOYSI-UHFFFAOYSA-N ethyl n-methyl-n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)N(C)S(=O)(=O)C1=CC=C(C)C=C1 CXLBYPJSAWOYSI-UHFFFAOYSA-N 0.000 description 3
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- QTYDNBLDZCJBBC-UHFFFAOYSA-N C(C)C1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound C(C)C1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC QTYDNBLDZCJBBC-UHFFFAOYSA-N 0.000 description 2
- SGXHNBVJMTXCPY-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C(C)C)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C(C)C)C SGXHNBVJMTXCPY-UHFFFAOYSA-N 0.000 description 2
- UUIZPHZFIIOUNE-UHFFFAOYSA-N COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC UUIZPHZFIIOUNE-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000011440 grout Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229940127017 oral antidiabetic Drugs 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- HQRWWHIETAKIMO-UHFFFAOYSA-N 1-phenylbutan-1-ol Chemical class CCCC(O)C1=CC=CC=C1 HQRWWHIETAKIMO-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
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-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
- NRPHEJYDQNWSJF-UHFFFAOYSA-N 3-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)N=C=O)=C1 NRPHEJYDQNWSJF-UHFFFAOYSA-N 0.000 description 1
- ZPBSZCDTNNYFHY-UHFFFAOYSA-N 4-ethyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CCC1=CC=C(S(=O)(=O)N=C=O)C=C1 ZPBSZCDTNNYFHY-UHFFFAOYSA-N 0.000 description 1
- JVFCCRJSBNUDDU-UHFFFAOYSA-N 4-phenylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=CC=C1 JVFCCRJSBNUDDU-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- QWVRQSHZVLYRGA-UHFFFAOYSA-N C(C)(C)C1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC Chemical compound C(C)(C)C1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC QWVRQSHZVLYRGA-UHFFFAOYSA-N 0.000 description 1
- FKUHUJNUUPQBPS-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CC(C)C)C.[Na] Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CC(C)C)C.[Na] FKUHUJNUUPQBPS-UHFFFAOYSA-N 0.000 description 1
- BRPWJGGNZPPHPH-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCC(C)C)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCC(C)C)C BRPWJGGNZPPHPH-UHFFFAOYSA-N 0.000 description 1
- KZQGKHFWQGKZKV-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCC)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCCC)C KZQGKHFWQGKZKV-UHFFFAOYSA-N 0.000 description 1
- MJCOZDIYSTVCFC-UHFFFAOYSA-N C1(CCCCC1)N(C(=O)OC(C)S(=O)(=O)C)CCCC Chemical compound C1(CCCCC1)N(C(=O)OC(C)S(=O)(=O)C)CCCC MJCOZDIYSTVCFC-UHFFFAOYSA-N 0.000 description 1
- ITKNZZZSCYVMSW-UHFFFAOYSA-N CC=1C=C(C=CC1)S(=O)(=O)N(C(=O)OCC)CCCC.[Na] Chemical compound CC=1C=C(C=CC1)S(=O)(=O)N(C(=O)OCC)CCCC.[Na] ITKNZZZSCYVMSW-UHFFFAOYSA-N 0.000 description 1
- BTSODEYLXPCYNU-UHFFFAOYSA-N CCCCCCN(C(=O)OCC)S(=O)(=O)C1=CC(C)=C(C)C=C1 Chemical compound CCCCCCN(C(=O)OCC)S(=O)(=O)C1=CC(C)=C(C)C=C1 BTSODEYLXPCYNU-UHFFFAOYSA-N 0.000 description 1
- AWNJBVFZTVGLLR-UHFFFAOYSA-N CCCCOC(NS(C(C=C1)=CC=C1C1=CC=CC=C1)(=O)=O)=O Chemical compound CCCCOC(NS(C(C=C1)=CC=C1C1=CC=CC=C1)(=O)=O)=O AWNJBVFZTVGLLR-UHFFFAOYSA-N 0.000 description 1
- AFUNFTWQTLZMNW-UHFFFAOYSA-N CCOC(NCS(C1CCCCC1)(=O)=O)=O Chemical compound CCOC(NCS(C1CCCCC1)(=O)=O)=O AFUNFTWQTLZMNW-UHFFFAOYSA-N 0.000 description 1
- LLQWEWYYTZYEPM-UHFFFAOYSA-N COC(C=CC(S(NC(OCCC1=CC=CC=C1)=O)(=O)=O)=C1)=C1OC Chemical compound COC(C=CC(S(NC(OCCC1=CC=CC=C1)=O)(=O)=O)=C1)=C1OC LLQWEWYYTZYEPM-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
- QJIKFNAHUAFCTD-UHFFFAOYSA-N COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC.[Na] Chemical compound COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)CCCC.[Na] QJIKFNAHUAFCTD-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- AUOLSMHJPJPGMI-UHFFFAOYSA-N O=C=NS(=O)(=O)CC1CCCCC1 Chemical compound O=C=NS(=O)(=O)CC1CCCCC1 AUOLSMHJPJPGMI-UHFFFAOYSA-N 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical class CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- AAYHAFZXFMIUSN-UHFFFAOYSA-N cyclohexanesulfonamide Chemical compound NS(=O)(=O)C1CCCCC1 AAYHAFZXFMIUSN-UHFFFAOYSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- BCAARMUWIRURQS-UHFFFAOYSA-N dicalcium;oxocalcium;silicate Chemical compound [Ca+2].[Ca+2].[Ca]=O.[O-][Si]([O-])([O-])[O-] BCAARMUWIRURQS-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- KWHXRPOBVUXTNC-UHFFFAOYSA-N ethyl N-(4-methoxyphenyl)sulfonyl-N-methylcarbamate Chemical compound COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C KWHXRPOBVUXTNC-UHFFFAOYSA-N 0.000 description 1
- YXTSNKIFXSHVFR-UHFFFAOYSA-N ethyl N-(benzenesulfonyl)-N-hexylcarbamate Chemical compound C1(=CC=CC=C1)S(=O)(=O)N(C(=O)OCC)CCCCCC YXTSNKIFXSHVFR-UHFFFAOYSA-N 0.000 description 1
- XAHONZKANMMOGS-UHFFFAOYSA-N ethyl N-butyl-N-(3-methylbutylsulfonyl)carbamate Chemical compound C(CC(C)C)S(=O)(=O)N(C(=O)OCC)CCCC XAHONZKANMMOGS-UHFFFAOYSA-N 0.000 description 1
- UDKHQNVNZSMYFY-UHFFFAOYSA-N ethyl N-cyclohexylsulfonyl-N-hexylcarbamate Chemical compound CCCCCCN(C(=O)OCC)S(=O)(=O)C1CCCCC1 UDKHQNVNZSMYFY-UHFFFAOYSA-N 0.000 description 1
- VYWRBAWFPGUTSI-UHFFFAOYSA-N ethyl N-hexyl-N-(3-methylbutylsulfonyl)carbamate Chemical compound CCCCCCN(C(=O)OCC)S(=O)(=O)CCC(C)C VYWRBAWFPGUTSI-UHFFFAOYSA-N 0.000 description 1
- WUAOUOQEZHIKQI-UHFFFAOYSA-N ethyl N-hexyl-N-naphthalen-2-ylsulfonylcarbamate Chemical compound C1=C(C=CC2=CC=CC=C12)S(=O)(=O)N(C(=O)OCC)CCCCCC WUAOUOQEZHIKQI-UHFFFAOYSA-N 0.000 description 1
- AUASHCDCDOYZFR-UHFFFAOYSA-N ethyl N-methyl-N-(3-methylphenyl)sulfonylcarbamate Chemical compound CC=1C=C(C=CC1)S(=O)(=O)N(C(=O)OCC)C AUASHCDCDOYZFR-UHFFFAOYSA-N 0.000 description 1
- JRWGBIIVGFLGBX-UHFFFAOYSA-N ethyl N-naphthalen-2-ylsulfonylcarbamate Chemical compound C(C)OC(=O)NS(=O)(=O)C1=CC2=CC=CC=C2C=C1 JRWGBIIVGFLGBX-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- DFWQXANLGSXMKF-UHFFFAOYSA-N ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical class CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 DFWQXANLGSXMKF-UHFFFAOYSA-N 0.000 description 1
- GZXSDYYWLZERLF-UHFFFAOYSA-N ethyl n-ethylcarbamate Chemical class CCNC(=O)OCC GZXSDYYWLZERLF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 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
- WOPQIFVLLOZORP-UHFFFAOYSA-N methyl N-(4-ethylphenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC=C(C=C1)CC)=O WOPQIFVLLOZORP-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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OMSRWEPANMKLLD-UHFFFAOYSA-N n-(oxomethylidene)-4-phenylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N=C=O)=CC=C1C1=CC=CC=C1 OMSRWEPANMKLLD-UHFFFAOYSA-N 0.000 description 1
- YYTMTGSQADIJNA-UHFFFAOYSA-N n-(oxomethylidene)-4-propylbenzenesulfonamide Chemical compound CCCC1=CC=C(S(=O)(=O)N=C=O)C=C1 YYTMTGSQADIJNA-UHFFFAOYSA-N 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- ZDEBIIYKHIBAGS-UHFFFAOYSA-N n-(oxomethylidene)hexane-1-sulfonamide Chemical compound CCCCCCS(=O)(=O)N=C=O ZDEBIIYKHIBAGS-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Landscapes
- 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 |
|---|---|---|---|
| SE201887T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE201887C1 true SE201887C1 (enrdf_load_stackoverflow) | 1965-01-01 |
Family
ID=41986068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE201887D SE201887C1 (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| SE (1) | SE201887C1 (enrdf_load_stackoverflow) |
-
0
- SE SE201887D patent/SE201887C1/sv unknown
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