NO792148L - Sulfonylurinstoff, fremgangsmaate til dets fremstilling, farmasoeytiske preparater paa basis av forbindelsene og deres anvendelse - Google Patents
Sulfonylurinstoff, fremgangsmaate til dets fremstilling, farmasoeytiske preparater paa basis av forbindelsene og deres anvendelseInfo
- Publication number
- NO792148L NO792148L NO792148A NO792148A NO792148L NO 792148 L NO792148 L NO 792148L NO 792148 A NO792148 A NO 792148A NO 792148 A NO792148 A NO 792148A NO 792148 L NO792148 L NO 792148L
- Authority
- NO
- Norway
- Prior art keywords
- oxo
- benzenesulfonyl
- isoindoline
- carboxamido
- ethyl7
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title description 10
- 239000000126 substance Substances 0.000 title description 9
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- -1 dialkylcycloalkyl Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000004202 carbamide Substances 0.000 claims description 17
- 235000013877 carbamide Nutrition 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000008280 blood Substances 0.000 claims description 11
- 210000004369 blood Anatomy 0.000 claims description 11
- 229940100389 Sulfonylurea Drugs 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000003672 ureas Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical class NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical class OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 claims description 3
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzene seleninic acid Natural products O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical group O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003455 sulfinic acids Chemical class 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 229960001330 hydroxycarbamide Drugs 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000002844 melting Methods 0.000 description 74
- 230000008018 melting Effects 0.000 description 74
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 68
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 32
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000155 melt Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 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
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- XTBAPWCYTNCZTO-UHFFFAOYSA-N isoindol-1-one Chemical compound C1=CC=C2C(=O)N=CC2=C1 XTBAPWCYTNCZTO-UHFFFAOYSA-N 0.000 description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 2
- 230000005923 long-lasting effect Effects 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
- 229910000474 mercury oxide Inorganic materials 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
- APTFDFXACXBQDO-UHFFFAOYSA-N 1-butyl-3-hydroxyurea Chemical compound CCCCNC(=O)NO APTFDFXACXBQDO-UHFFFAOYSA-N 0.000 description 1
- FYEPDPWQNJDLJT-UHFFFAOYSA-N 1-isocyanatopropan-2-ylbenzene Chemical compound O=C=NCC(C)C1=CC=CC=C1 FYEPDPWQNJDLJT-UHFFFAOYSA-N 0.000 description 1
- JFRFGCASIOOBDA-UHFFFAOYSA-N 2,2,2-trichloro-n-cyclohexylacetamide Chemical compound ClC(Cl)(Cl)C(=O)NC1CCCCC1 JFRFGCASIOOBDA-UHFFFAOYSA-N 0.000 description 1
- OKETYEJKSGDMRO-UHFFFAOYSA-N 2,3-dihydroisoindol-1-one;sodium Chemical compound [Na].C1=CC=C2C(=O)NCC2=C1 OKETYEJKSGDMRO-UHFFFAOYSA-N 0.000 description 1
- HACRKYQRZABURO-UHFFFAOYSA-N 2-phenylethyl isocyanate Chemical compound O=C=NCCC1=CC=CC=C1 HACRKYQRZABURO-UHFFFAOYSA-N 0.000 description 1
- VNPWIDIVQOFLQS-UHFFFAOYSA-N 3-methyl-2,3-dihydroisoindol-1-one Chemical compound C1=CC=C2C(C)NC(=O)C2=C1 VNPWIDIVQOFLQS-UHFFFAOYSA-N 0.000 description 1
- IDRHULKVTQXQRN-UHFFFAOYSA-N 3-oxo-1h-isoindole-2-carbonyl chloride Chemical compound C1=CC=C2C(=O)N(C(=O)Cl)CC2=C1 IDRHULKVTQXQRN-UHFFFAOYSA-N 0.000 description 1
- QQNMVGPIDSWXTK-UHFFFAOYSA-N 4,6-dichloro-2,3-dihydroisoindol-1-one Chemical compound ClC1=CC(Cl)=CC2=C1CNC2=O QQNMVGPIDSWXTK-UHFFFAOYSA-N 0.000 description 1
- PSKBCTAXSVTOTA-UHFFFAOYSA-N 5-chloro-2,3-dihydroisoindol-1-one Chemical compound ClC1=CC=C2C(=O)NCC2=C1 PSKBCTAXSVTOTA-UHFFFAOYSA-N 0.000 description 1
- PXYMACAYRGWCDC-UHFFFAOYSA-N 5-cyclohexyl-1h-imidazole-2-carboxamide Chemical class N1C(C(=O)N)=NC(C2CCCCC2)=C1 PXYMACAYRGWCDC-UHFFFAOYSA-N 0.000 description 1
- AHKBMKCIJLCNIH-UHFFFAOYSA-N 5-methyl-2,3-dihydroisoindol-1-one Chemical compound CC1=CC=C2C(=O)NCC2=C1 AHKBMKCIJLCNIH-UHFFFAOYSA-N 0.000 description 1
- VCEOKEOSVQLRNW-UHFFFAOYSA-N 6-chloro-2,3-dihydroisoindol-1-one Chemical compound ClC1=CC=C2CNC(=O)C2=C1 VCEOKEOSVQLRNW-UHFFFAOYSA-N 0.000 description 1
- HFFIGYBPDNKEMJ-UHFFFAOYSA-N 6-methyl-2,3-dihydroisoindol-1-one Chemical compound CC1=CC=C2CNC(=O)C2=C1 HFFIGYBPDNKEMJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940127003 anti-diabetic drug Drugs 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 1
- RJNJWHFSKNJCTB-UHFFFAOYSA-N benzylurea Chemical compound NC(=O)NCC1=CC=CC=C1 RJNJWHFSKNJCTB-UHFFFAOYSA-N 0.000 description 1
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 1
- ONENTOHJOJEWPH-UHFFFAOYSA-N n-(benzenesulfonyl)-1h-imidazole-2-carboxamide Chemical class N=1C=CNC=1C(=O)NS(=O)(=O)C1=CC=CC=C1 ONENTOHJOJEWPH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 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
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 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
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 nitrogen-containing ring
- C07D217/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782828079 DE2828079A1 (de) | 1978-06-27 | 1978-06-27 | Sulfonylharnstoffe und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO792148L true NO792148L (no) | 1979-12-28 |
Family
ID=6042843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO792148A NO792148L (no) | 1978-06-27 | 1979-06-26 | Sulfonylurinstoff, fremgangsmaate til dets fremstilling, farmasoeytiske preparater paa basis av forbindelsene og deres anvendelse |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4282239A (pt) |
| EP (1) | EP0006587B1 (pt) |
| JP (1) | JPS5511580A (pt) |
| AR (1) | AR223975A1 (pt) |
| AT (1) | ATE382T1 (pt) |
| AU (1) | AU527494B2 (pt) |
| BE (1) | BE877308A (pt) |
| CA (1) | CA1122598A (pt) |
| CU (1) | CU35107A (pt) |
| DD (1) | DD144539A5 (pt) |
| DE (2) | DE2828079A1 (pt) |
| DK (1) | DK269579A (pt) |
| ES (6) | ES481755A1 (pt) |
| FI (1) | FI792008A (pt) |
| FR (1) | FR2429786A1 (pt) |
| GB (1) | GB2024221A (pt) |
| GR (1) | GR74059B (pt) |
| IL (1) | IL57639A0 (pt) |
| IT (1) | IT1121923B (pt) |
| JO (1) | JO1010B1 (pt) |
| LU (1) | LU81423A1 (pt) |
| MA (1) | MA18501A1 (pt) |
| MT (1) | MTP848B (pt) |
| MW (1) | MW2079A1 (pt) |
| NL (1) | NL7904975A (pt) |
| NO (1) | NO792148L (pt) |
| OA (1) | OA06283A (pt) |
| PT (1) | PT69803A (pt) |
| SE (1) | SE7905557L (pt) |
| ZA (1) | ZA793178B (pt) |
| ZM (1) | ZM5879A1 (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2951135A1 (de) * | 1979-12-19 | 1981-06-25 | Hoechst Ag, 6230 Frankfurt | Sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| DE3134780A1 (de) * | 1981-09-02 | 1983-03-10 | Hoechst Ag, 6000 Frankfurt | "sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung" |
| CN103058913B (zh) * | 2012-12-13 | 2015-09-30 | 江苏弘和药物研发有限公司 | 5-氯异吲哚酮的合成方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1618389U (de) | 1950-10-05 | 1950-12-28 | Eisen Fuchs G M B H | Endpreistabelle fuer walzeisen. |
| DE1670700U (de) | 1952-11-12 | 1954-01-21 | Siemens Ag | Aufhaengevorrichtung fuer pendelleuchten. |
| DE1670660U (de) | 1953-08-26 | 1954-01-21 | Aerzener Bastkunst M Cramer | Halter fuer blumentoepfe und pflanzenschalen. |
| LU47776A1 (pt) * | 1964-07-30 | 1966-07-13 | ||
| DE1445774A1 (de) * | 1964-07-30 | 1969-01-23 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| FR1528139A (fr) * | 1966-05-14 | 1968-06-07 | Hoechst Ag | Benzène-sulfonyl-urées et leur préparation |
| DE1670700B2 (de) * | 1966-05-14 | 1978-06-22 | Hoechst Ag, 6000 Frankfurt | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und deren Verwendung |
| LU56669A1 (pt) * | 1967-08-12 | 1970-02-18 | ||
| DE2000339C3 (de) * | 1970-01-05 | 1979-04-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Isochinolinderivate |
| US3819633A (en) * | 1970-04-01 | 1974-06-25 | Erba Carlo Spa | (iso)quinolyl sulfonylureas having antidiabetic activity |
| GB1329812A (en) * | 1971-02-15 | 1973-09-12 | Science Union & Cie | Benzenesulphonyl semicarbazides and a process for their preparation |
| BE791638A (fr) * | 1971-11-20 | 1973-05-21 | Hoechst Ag | Sulfonyl-urees, leur procede de preparation et leurs applications |
| DE2238870C3 (de) | 1972-08-07 | 1978-09-28 | Hoechst Ag, 6000 Frankfurt | Benzolsulfonylharnstoffe |
| IL45823A (en) * | 1973-10-20 | 1977-10-31 | Hoechst Ag | Substituted 1-phenyl-4-alkyl(dialkyl or cyclic) aminoalkyl-1,4-dihydro-2h-isoquinoline-3-one derivatives |
| SE431451B (sv) * | 1973-10-24 | 1984-02-06 | Otsuka Pharma Co Ltd | Forfarande for framstellning av 2,3-dihydroxipropoxikinoliner eller -isokinoliner |
| US4129729A (en) * | 1978-01-03 | 1978-12-12 | Monsanto Company | 3-Phenacyl and phenacylidene phthalimidines and corresponding naphthoyl derivatives |
-
1974
- 1974-06-25 MT MT848A patent/MTP848B/xx unknown
-
1978
- 1978-06-27 DE DE19782828079 patent/DE2828079A1/de not_active Withdrawn
-
1979
- 1979-04-22 PT PT69803A patent/PT69803A/pt unknown
- 1979-05-07 FR FR7911479A patent/FR2429786A1/fr active Granted
- 1979-06-21 ES ES481755A patent/ES481755A1/es not_active Expired
- 1979-06-21 CU CU7935107A patent/CU35107A/es unknown
- 1979-06-22 DE DE7979102066T patent/DE2961309D1/de not_active Expired
- 1979-06-22 AT AT79102066T patent/ATE382T1/de active
- 1979-06-22 EP EP79102066A patent/EP0006587B1/de not_active Expired
- 1979-06-25 MW MW20/79A patent/MW2079A1/xx unknown
- 1979-06-25 AR AR277039A patent/AR223975A1/es active
- 1979-06-25 DD DD79213876A patent/DD144539A5/de unknown
- 1979-06-25 ZM ZM58/79A patent/ZM5879A1/xx unknown
- 1979-06-25 FI FI792008A patent/FI792008A/fi not_active Application Discontinuation
- 1979-06-25 LU LU81423A patent/LU81423A1/de unknown
- 1979-06-25 GB GB7922038A patent/GB2024221A/en not_active Withdrawn
- 1979-06-25 US US06/051,548 patent/US4282239A/en not_active Expired - Lifetime
- 1979-06-25 IL IL57639A patent/IL57639A0/xx unknown
- 1979-06-25 SE SE7905557A patent/SE7905557L/xx unknown
- 1979-06-25 GR GR59423A patent/GR74059B/el unknown
- 1979-06-25 IT IT23846/79A patent/IT1121923B/it active
- 1979-06-25 JO JO19791010A patent/JO1010B1/en active
- 1979-06-26 CA CA330,942A patent/CA1122598A/en not_active Expired
- 1979-06-26 OA OA56836A patent/OA06283A/xx unknown
- 1979-06-26 ZA ZA793178A patent/ZA793178B/xx unknown
- 1979-06-26 MA MA18696A patent/MA18501A1/fr unknown
- 1979-06-26 AU AU48380/79A patent/AU527494B2/en not_active Expired - Fee Related
- 1979-06-26 DK DK269579A patent/DK269579A/da not_active Application Discontinuation
- 1979-06-26 NO NO792148A patent/NO792148L/no unknown
- 1979-06-26 NL NL7904975A patent/NL7904975A/nl not_active Application Discontinuation
- 1979-06-27 BE BE0/195996A patent/BE877308A/xx unknown
- 1979-06-27 JP JP8027979A patent/JPS5511580A/ja active Pending
-
1980
- 1980-04-01 ES ES490201A patent/ES490201A0/es active Granted
- 1980-04-01 ES ES490199A patent/ES490199A0/es active Granted
- 1980-04-01 ES ES490202A patent/ES8101051A1/es not_active Expired
- 1980-04-01 ES ES490200A patent/ES490200A0/es active Granted
- 1980-04-01 ES ES490198A patent/ES8101049A1/es not_active Expired
Also Published As
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