DK141402B - Analogifremgangsmåde til fremstilling af sulfonylurinstoffer. - Google Patents
Analogifremgangsmåde til fremstilling af sulfonylurinstoffer. Download PDFInfo
- Publication number
- DK141402B DK141402B DK66875AA DK66875A DK141402B DK 141402 B DK141402 B DK 141402B DK 66875A A DK66875A A DK 66875AA DK 66875 A DK66875 A DK 66875A DK 141402 B DK141402 B DK 141402B
- Authority
- DK
- Denmark
- Prior art keywords
- carbon atoms
- tetrahydro
- alkyl
- general formula
- sulfonamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 7
- 229940100389 Sulfonylurea Drugs 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 38
- -1 1-pyrrolidinylcarbonyl Chemical group 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000007858 starting material Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- IPJWYIMXBIVBIE-UHFFFAOYSA-N 3-(pyrrolidine-1-carbonyl)-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonamide Chemical compound C1CC2=CC(S(=O)(=O)N)=CC=C2CCN1C(=O)N1CCCC1 IPJWYIMXBIVBIE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004946 alkenylalkyl group Chemical group 0.000 claims description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- 238000004458 analytical method Methods 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- UUSODXRMARGLBX-UHFFFAOYSA-N cyclohex-3-en-1-amine Chemical compound NC1CCC=CC1 UUSODXRMARGLBX-UHFFFAOYSA-N 0.000 claims 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims 1
- IRUXSKJXJFMZPQ-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine-7-sulfonamide Chemical compound C1CNCCC2=CC(S(=O)(=O)N)=CC=C21 IRUXSKJXJFMZPQ-UHFFFAOYSA-N 0.000 description 8
- SAEYSWGHEJBKJR-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine-7-sulfonamide;hydrochloride Chemical compound Cl.C1CNCCC2=CC(S(=O)(=O)N)=CC=C21 SAEYSWGHEJBKJR-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- HTKJPTDHFNSMBO-UHFFFAOYSA-N ethyl n-[[3-(dimethylcarbamoyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]sulfonyl]carbamate Chemical compound C1CN(C(=O)N(C)C)CCC2=CC(S(=O)(=O)NC(=O)OCC)=CC=C21 HTKJPTDHFNSMBO-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- FTGNOMQIUBEEQB-UHFFFAOYSA-N n,n-dimethyl-7-sulfamoyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCC2=CC=C(S(N)(=O)=O)C=C21 FTGNOMQIUBEEQB-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000010030 glucose lowering effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LYEVRBLWCZKGAP-UHFFFAOYSA-N n-ethyl-7-sulfamoyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)NCC)CCC2=CC=C(S(N)(=O)=O)C=C21 LYEVRBLWCZKGAP-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- REBPYAODWOHSEM-UHFFFAOYSA-N 1-[[3-(azepane-1-carbonyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]sulfonyl]-3-cyclohexylurea Chemical compound C=1C=C2CCN(C(=O)N3CCCCCC3)CCC2=CC=1S(=O)(=O)NC(=O)NC1CCCCC1 REBPYAODWOHSEM-UHFFFAOYSA-N 0.000 description 1
- NRIAHRVBMRSEPN-UHFFFAOYSA-N 1-cyclohexyl-3-[[3-(piperidine-1-carbonyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]sulfonyl]urea Chemical compound C=1C=C2CCN(C(=O)N3CCCCC3)CCC2=CC=1S(=O)(=O)NC(=O)NC1CCCCC1 NRIAHRVBMRSEPN-UHFFFAOYSA-N 0.000 description 1
- JZNSPHRXZDXNFP-UHFFFAOYSA-N 1-cyclohexyl-3-[[3-(pyrrolidine-1-carbonyl)-1,2,4,5-tetrahydro-3-benzazepin-7-yl]sulfonyl]urea Chemical compound C=1C=C2CCN(C(=O)N3CCCC3)CCC2=CC=1S(=O)(=O)NC(=O)NC1CCCCC1 JZNSPHRXZDXNFP-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- GQMOMOBMXHFFLZ-UHFFFAOYSA-N 3-(3,6-dihydro-2h-pyridine-1-carbonyl)-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonamide Chemical compound C1CC2=CC(S(=O)(=O)N)=CC=C2CCN1C(=O)N1CCC=CC1 GQMOMOBMXHFFLZ-UHFFFAOYSA-N 0.000 description 1
- ZMCVNMJRGWFDPX-UHFFFAOYSA-N 3-(morpholine-4-carbonyl)-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonamide Chemical compound C1CC2=CC(S(=O)(=O)N)=CC=C2CCN1C(=O)N1CCOCC1 ZMCVNMJRGWFDPX-UHFFFAOYSA-N 0.000 description 1
- ZUCBVIPKFRJTBM-UHFFFAOYSA-N 3-(piperidine-1-carbonyl)-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonamide Chemical compound C1CC2=CC(S(=O)(=O)N)=CC=C2CCN1C(=O)N1CCCCC1 ZUCBVIPKFRJTBM-UHFFFAOYSA-N 0.000 description 1
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 1
- BSCWMRIFHUJKIQ-UHFFFAOYSA-N 7-(butylcarbamoylsulfamoyl)-n,n-dimethyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCC2=CC(S(=O)(=O)NC(=O)NCCCC)=CC=C21 BSCWMRIFHUJKIQ-UHFFFAOYSA-N 0.000 description 1
- IXXIMPXURGICHK-UHFFFAOYSA-N 7-(cycloheptylcarbamoylsulfamoyl)-n,n-dimethyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)N(C)C)CCC2=CC=C1S(=O)(=O)NC(=O)NC1CCCCCC1 IXXIMPXURGICHK-UHFFFAOYSA-N 0.000 description 1
- FQSWFTMIOSATJI-UHFFFAOYSA-N 7-(cyclohexylcarbamoylsulfamoyl)-n,n-dimethyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)N(C)C)CCC2=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 FQSWFTMIOSATJI-UHFFFAOYSA-N 0.000 description 1
- RJUJVOBJALNQJY-UHFFFAOYSA-N 7-(cyclohexylcarbamoylsulfamoyl)-n,n-dipropyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)N(CCC)CCC)CCC2=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RJUJVOBJALNQJY-UHFFFAOYSA-N 0.000 description 1
- OQPNRINCQXFFPX-UHFFFAOYSA-N 7-(cyclohexylcarbamoylsulfamoyl)-n-ethyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)NCC)CCC2=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 OQPNRINCQXFFPX-UHFFFAOYSA-N 0.000 description 1
- RWWNYYBXOWDSTB-UHFFFAOYSA-N 7-(cyclohexylcarbamoylsulfamoyl)-n-methyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)NC)CCC2=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RWWNYYBXOWDSTB-UHFFFAOYSA-N 0.000 description 1
- HNBHELMUMHPWEC-UHFFFAOYSA-N 7-(cyclohexylcarbamoylsulfamoyl)-n-propyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)NCCC)CCC2=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 HNBHELMUMHPWEC-UHFFFAOYSA-N 0.000 description 1
- FNOPWGONDSXJKA-UHFFFAOYSA-N 7-(cyclopentylcarbamoylsulfamoyl)-n,n-dimethyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)N(C)C)CCC2=CC=C1S(=O)(=O)NC(=O)NC1CCCC1 FNOPWGONDSXJKA-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- WIORSDCKXGFOKX-RZDIXWSQSA-N C1C[C@@H](C)CC[C@@H]1NC(=O)NS(=O)(=O)C1=CC=C(CCN(CC2)C(=O)N(C)C)C2=C1 Chemical compound C1C[C@@H](C)CC[C@@H]1NC(=O)NS(=O)(=O)C1=CC=C(CCN(CC2)C(=O)N(C)C)C2=C1 WIORSDCKXGFOKX-RZDIXWSQSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 108010015776 Glucose oxidase Proteins 0.000 description 1
- 239000004366 Glucose oxidase Substances 0.000 description 1
- 208000013016 Hypoglycemia Diseases 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- VCZFCDMBZCEPFV-UHFFFAOYSA-N azepane-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCCC1 VCZFCDMBZCEPFV-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 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
- 238000009835 boiling Methods 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([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
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VHFUHRXYRYWELT-UHFFFAOYSA-N methyl 2,2,2-trichloroacetate Chemical compound COC(=O)C(Cl)(Cl)Cl VHFUHRXYRYWELT-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 1
- UYQZCEYUPSAIPO-UHFFFAOYSA-N n,n-dibutyl-7-(cyclohexylcarbamoylsulfamoyl)-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)N(CCCC)CCCC)CCC2=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 UYQZCEYUPSAIPO-UHFFFAOYSA-N 0.000 description 1
- WHYRIKPJPSDPBS-UHFFFAOYSA-N n,n-dibutyl-7-sulfamoyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)N(CCCC)CCCC)CCC2=CC=C(S(N)(=O)=O)C=C21 WHYRIKPJPSDPBS-UHFFFAOYSA-N 0.000 description 1
- SSBIDBPAYDSMLM-UHFFFAOYSA-N n,n-diethyl-7-sulfamoyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)N(CC)CC)CCC2=CC=C(S(N)(=O)=O)C=C21 SSBIDBPAYDSMLM-UHFFFAOYSA-N 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- RXELUSSSEBVGMU-UHFFFAOYSA-N n,n-dipropyl-7-sulfamoyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)N(CCC)CCC)CCC2=CC=C(S(N)(=O)=O)C=C21 RXELUSSSEBVGMU-UHFFFAOYSA-N 0.000 description 1
- OWRABTHGOKNUDV-UHFFFAOYSA-N n,n-dipropylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)CCC OWRABTHGOKNUDV-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- XVRWIBQGQCJOQI-UHFFFAOYSA-N n-butyl-7-(cyclohexylcarbamoylsulfamoyl)-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=C2CCN(C(=O)NCCCC)CCC2=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 XVRWIBQGQCJOQI-UHFFFAOYSA-N 0.000 description 1
- PEFOLHOPGIFTNO-UHFFFAOYSA-N n-butyl-7-sulfamoyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)NCCCC)CCC2=CC=C(S(N)(=O)=O)C=C21 PEFOLHOPGIFTNO-UHFFFAOYSA-N 0.000 description 1
- XPHFZBNDYJSFEG-UHFFFAOYSA-N n-ethyl-n-methyl-7-sulfamoyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)N(C)CC)CCC2=CC=C(S(N)(=O)=O)C=C21 XPHFZBNDYJSFEG-UHFFFAOYSA-N 0.000 description 1
- XZVYDRLPXWFRIS-UHFFFAOYSA-N n-ethyl-n-methylcarbamoyl chloride Chemical compound CCN(C)C(Cl)=O XZVYDRLPXWFRIS-UHFFFAOYSA-N 0.000 description 1
- CUPAGEQUYSPEEA-UHFFFAOYSA-N n-methyl-7-sulfamoyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)NC)CCC2=CC=C(S(N)(=O)=O)C=C21 CUPAGEQUYSPEEA-UHFFFAOYSA-N 0.000 description 1
- SGJKQYGQLKFBIV-UHFFFAOYSA-N n-propan-2-yl-7-sulfamoyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1CN(C(=O)NC(C)C)CCC2=CC=C(S(N)(=O)=O)C=C21 SGJKQYGQLKFBIV-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- BIFDXOOJPDHKJH-UHFFFAOYSA-N piperidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCC1 BIFDXOOJPDHKJH-UHFFFAOYSA-N 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- XACWJIQLDLUFSR-UHFFFAOYSA-N pyrrolidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCC1 XACWJIQLDLUFSR-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical class OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH253974A CH593263A5 (en:Method) | 1974-02-22 | 1974-02-22 | |
| CH253974 | 1974-02-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK66875A DK66875A (en:Method) | 1975-11-03 |
| DK141402B true DK141402B (da) | 1980-03-10 |
| DK141402C DK141402C (en:Method) | 1980-09-08 |
Family
ID=4236065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK66875AA DK141402B (da) | 1974-02-22 | 1975-02-21 | Analogifremgangsmåde til fremstilling af sulfonylurinstoffer. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4024128A (en:Method) |
| JP (1) | JPS50117789A (en:Method) |
| AR (2) | AR215838A1 (en:Method) |
| AT (1) | AT343126B (en:Method) |
| BE (1) | BE825790A (en:Method) |
| CA (1) | CA1055935A (en:Method) |
| CH (1) | CH593263A5 (en:Method) |
| DD (1) | DD118633A5 (en:Method) |
| DE (1) | DE2507531A1 (en:Method) |
| DK (1) | DK141402B (en:Method) |
| ES (1) | ES434930A1 (en:Method) |
| FI (1) | FI59092C (en:Method) |
| FR (1) | FR2261774B1 (en:Method) |
| GB (1) | GB1472502A (en:Method) |
| HU (1) | HU170156B (en:Method) |
| IE (1) | IE40805B1 (en:Method) |
| IL (1) | IL46455A (en:Method) |
| LU (1) | LU71887A1 (en:Method) |
| NL (1) | NL7501029A (en:Method) |
| NO (1) | NO144038C (en:Method) |
| PH (1) | PH12224A (en:Method) |
| SE (1) | SE417604B (en:Method) |
| ZA (1) | ZA75300B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL106114B1 (pl) * | 1976-12-31 | 1979-11-30 | Akad Medyczna | Sposob wytwarzania nowych n-(4-/2-/pirazolo-1-karbonamido/-etylo/-benzenosulfonylo)-mocznikow |
| US4659706A (en) * | 1985-12-20 | 1987-04-21 | Smithkline Beckman Corporation | Sulfinyl and sulfonyl substituted 3-benzazepines |
| WO1988007858A1 (en) * | 1987-04-09 | 1988-10-20 | Smithkline Beckman Corporation | Sulfinyl and sulfonyl substituted 3-benzazepines |
| EP1283199A4 (en) * | 2000-05-16 | 2003-12-17 | Takeda Chemical Industries Ltd | MELANINE CONCENTRATING HORMONE ANTAGONISTS |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1443911C3 (de) * | 1964-12-08 | 1974-12-05 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
| DE1921737A1 (de) * | 1969-04-29 | 1970-11-12 | Bayer Ag | Heterocyclische Acylreste enthaltende Sulfonylharnstoffe und Sulfonylsemicarbazide mit antidiabetischer Wirkung |
| DE2027436A1 (en) * | 1970-06-04 | 1971-12-16 | Dr Karl Thomae GmbH, 7950 Biberach | Sulphenylurea cpds, hypoglycaemics |
| DE1933388A1 (de) * | 1969-07-01 | 1971-01-21 | Thomae Gmbh Dr K | Neue Sulfonylharnstoffe und Verfahren zu ihrer Herstellung |
| US3725388A (en) * | 1970-06-25 | 1973-04-03 | Boehringer Sohn Ingelheim | N-acyl-7-(n{41 -cycloalkyl-ureido-n{40 -sulfonyl)-isoquinolines and -benzazepines and alkali metal salts thereof |
-
1974
- 1974-02-22 CH CH253974A patent/CH593263A5/xx not_active IP Right Cessation
-
1975
- 1975-01-15 ZA ZA00750300A patent/ZA75300B/xx unknown
- 1975-01-17 IL IL46455A patent/IL46455A/xx unknown
- 1975-01-29 NL NL7501029A patent/NL7501029A/xx not_active Application Discontinuation
- 1975-02-12 FI FI750379A patent/FI59092C/fi not_active IP Right Cessation
- 1975-02-12 PH PH16804A patent/PH12224A/en unknown
- 1975-02-13 US US05/549,572 patent/US4024128A/en not_active Expired - Lifetime
- 1975-02-17 IE IE316/75A patent/IE40805B1/xx unknown
- 1975-02-19 SE SE7501885A patent/SE417604B/xx unknown
- 1975-02-19 AR AR257691A patent/AR215838A1/es active
- 1975-02-20 FR FR7505270A patent/FR2261774B1/fr not_active Expired
- 1975-02-20 LU LU71887A patent/LU71887A1/xx unknown
- 1975-02-20 CA CA220,472A patent/CA1055935A/en not_active Expired
- 1975-02-20 JP JP50020434A patent/JPS50117789A/ja active Pending
- 1975-02-20 DD DD184318A patent/DD118633A5/xx unknown
- 1975-02-21 HU HUHO1773A patent/HU170156B/hu unknown
- 1975-02-21 BE BE153566A patent/BE825790A/xx not_active IP Right Cessation
- 1975-02-21 DK DK66875AA patent/DK141402B/da not_active IP Right Cessation
- 1975-02-21 ES ES434930A patent/ES434930A1/es not_active Expired
- 1975-02-21 NO NO750593A patent/NO144038C/no unknown
- 1975-02-21 AT AT134475A patent/AT343126B/de not_active IP Right Cessation
- 1975-02-21 DE DE19752507531 patent/DE2507531A1/de not_active Ceased
- 1975-02-21 GB GB733775A patent/GB1472502A/en not_active Expired
- 1975-09-03 AR AR260241A patent/AR218212A1/es active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |