DE2022746A1 - Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren Herstellung - Google Patents
Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren HerstellungInfo
- Publication number
- DE2022746A1 DE2022746A1 DE19702022746 DE2022746A DE2022746A1 DE 2022746 A1 DE2022746 A1 DE 2022746A1 DE 19702022746 DE19702022746 DE 19702022746 DE 2022746 A DE2022746 A DE 2022746A DE 2022746 A1 DE2022746 A1 DE 2022746A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- given above
- meaning given
- compounds
- tetrahydronaphthalene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000008280 blood Substances 0.000 title claims description 6
- 210000004369 blood Anatomy 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- DQGBPFUIAYFOLA-UHFFFAOYSA-N 2-(sulfonylamino)pyrimidine Chemical class O=S(=O)=NC1=NC=CC=N1 DQGBPFUIAYFOLA-UHFFFAOYSA-N 0.000 title description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000003230 pyrimidines Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- VITPICOSHHCBFU-UHFFFAOYSA-N 1-sulfonylguanidine Chemical class NC(=N)N=S(=O)=O VITPICOSHHCBFU-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- XHHQBJXXOLETKS-UHFFFAOYSA-N N-pyrimidin-2-yl-1,2,3,4-tetrahydronaphthalene-1-sulfonamide Chemical class C1(CCCC2=CC=CC=C12)S(=O)(=O)NC1=NC=CC=N1 XHHQBJXXOLETKS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000005695 dehalogenation reaction Methods 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 150000005006 2-aminopyrimidines Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- -1 alkyl radical Chemical class 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- 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 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000005695 2-halopyrimidines Chemical class 0.000 description 2
- 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 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000004283 biguanides Chemical class 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- SRYALXBZLHTHHG-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N)CCCC2=C1 SRYALXBZLHTHHG-UHFFFAOYSA-N 0.000 description 1
- FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 1
- 150000008319 1H-pyrimidin-2-ones Chemical class 0.000 description 1
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 description 1
- VQEHSBSZLWUDML-UHFFFAOYSA-N 2-chloro-5-(2-methylpropyl)pyrimidine Chemical compound CC(C)CC1=CN=C(Cl)N=C1 VQEHSBSZLWUDML-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- NDQUBPLFXGTFFG-UHFFFAOYSA-N 5,6,7,8-tetrahydronaphthalene-2-sulfonamide Chemical compound C1CCCC2=CC(S(=O)(=O)N)=CC=C21 NDQUBPLFXGTFFG-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- ZBSQZROSYZVCNG-UHFFFAOYSA-N NC1=NC=C(C=N1)OC1CCCCC1 Chemical compound NC1=NC=C(C=N1)OC1CCCCC1 ZBSQZROSYZVCNG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- AYIJTSJNSMGSMG-UHFFFAOYSA-M [Cl-].C[N+](C)(C)C1=NC=C(C=N1)CC(C)C Chemical compound [Cl-].C[N+](C)(C)C1=NC=C(C=N1)CC(C)C AYIJTSJNSMGSMG-UHFFFAOYSA-M 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 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
- 235000010419 agar Nutrition 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000005005 aminopyrimidines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- HLBLNLYCFFWMFF-UHFFFAOYSA-N n-pyrimidin-2-ylbenzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NC1=NC=CC=N1 HLBLNLYCFFWMFF-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000003765 sweetening agent 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
- 229940095064 tartrate Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702022746 DE2022746A1 (de) | 1970-05-09 | 1970-05-09 | Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren Herstellung |
| CH359575A CH572913A5 (enrdf_load_stackoverflow) | 1970-05-09 | 1971-05-05 | |
| CH664071A CH563992A5 (enrdf_load_stackoverflow) | 1970-05-09 | 1971-05-05 | |
| CH359375A CH563993A5 (enrdf_load_stackoverflow) | 1970-05-09 | 1971-05-05 | |
| CH359475A CH563994A5 (enrdf_load_stackoverflow) | 1970-05-09 | 1971-05-05 | |
| GB03422/71A GB1291661A (en) | 1970-05-09 | 1971-05-06 | Sulphonylamino-pyrimidines |
| AT410372A AT307428B (de) | 1970-05-09 | 1971-05-07 | Verfahren zur Herstellung von neuen Tetrahydronaphthalinsulfonylaminopyrimidinen sowie deren Salzen |
| AT399671A AT306728B (de) | 1970-05-09 | 1971-05-07 | Verfahren zur Herstellung von neuen Tetrahydronaphthalinsulfonylaminopyrimidinen sowie deren Salzen |
| FR7116514A FR2100641B1 (enrdf_load_stackoverflow) | 1970-05-09 | 1971-05-07 | |
| AT410472A AT306738B (de) | 1970-05-09 | 1971-05-07 | Verfahren zur Herstellung von neuen Tetrahydronaphthalinsulfonylaminopyrimidinen sowie deren Salzen |
| AT410272A AT306737B (de) | 1970-05-09 | 1971-05-07 | Verfahren zur Herstellung von neuen Tetrahydronaphthalinsulfonylaminopyrimidinen sowie deren Salzen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702022746 DE2022746A1 (de) | 1970-05-09 | 1970-05-09 | Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2022746A1 true DE2022746A1 (de) | 1971-12-02 |
Family
ID=5770688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702022746 Pending DE2022746A1 (de) | 1970-05-09 | 1970-05-09 | Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| AT (4) | AT306738B (enrdf_load_stackoverflow) |
| CH (4) | CH563994A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2022746A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2100641B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1291661A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2125514A1 (enrdf_load_stackoverflow) * | 1971-02-17 | 1972-09-29 | Hoechst Ag | |
| EP0420064A3 (en) * | 1989-09-25 | 1992-02-26 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
| WO2012070015A1 (en) * | 2010-11-24 | 2012-05-31 | Stemergie Biotechnology Sa | Inhibitors of the activity of complex iii of the mitochondrial electron transport chain and use thereof for treating diseases |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2152230A1 (de) * | 1971-10-20 | 1973-04-26 | Boehringer Mannheim Gmbh | Blutzuckersenkende sulfonylaminopyrimidine und verfahren zu deren herstellung |
-
1970
- 1970-05-09 DE DE19702022746 patent/DE2022746A1/de active Pending
-
1971
- 1971-05-05 CH CH359475A patent/CH563994A5/xx not_active IP Right Cessation
- 1971-05-05 CH CH359375A patent/CH563993A5/xx not_active IP Right Cessation
- 1971-05-05 CH CH664071A patent/CH563992A5/xx not_active IP Right Cessation
- 1971-05-05 CH CH359575A patent/CH572913A5/xx not_active IP Right Cessation
- 1971-05-06 GB GB03422/71A patent/GB1291661A/en not_active Expired
- 1971-05-07 AT AT410472A patent/AT306738B/de not_active IP Right Cessation
- 1971-05-07 AT AT410272A patent/AT306737B/de not_active IP Right Cessation
- 1971-05-07 AT AT399671A patent/AT306728B/de not_active IP Right Cessation
- 1971-05-07 AT AT410372A patent/AT307428B/de not_active IP Right Cessation
- 1971-05-07 FR FR7116514A patent/FR2100641B1/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2125514A1 (enrdf_load_stackoverflow) * | 1971-02-17 | 1972-09-29 | Hoechst Ag | |
| EP0420064A3 (en) * | 1989-09-25 | 1992-02-26 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
| WO2012070015A1 (en) * | 2010-11-24 | 2012-05-31 | Stemergie Biotechnology Sa | Inhibitors of the activity of complex iii of the mitochondrial electron transport chain and use thereof for treating diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| AT307428B (de) | 1973-05-25 |
| AT306728B (de) | 1973-04-25 |
| CH563992A5 (enrdf_load_stackoverflow) | 1975-07-15 |
| AT306738B (de) | 1973-04-25 |
| CH572913A5 (enrdf_load_stackoverflow) | 1976-02-27 |
| FR2100641B1 (enrdf_load_stackoverflow) | 1975-04-18 |
| GB1291661A (en) | 1972-10-04 |
| CH563994A5 (enrdf_load_stackoverflow) | 1975-07-15 |
| FR2100641A1 (enrdf_load_stackoverflow) | 1972-03-24 |
| CH563993A5 (enrdf_load_stackoverflow) | 1975-07-15 |
| AT306737B (de) | 1973-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2517229A1 (de) | Phenylalkylcarbonsaeure-derivate und verfahren zu ihrer herstellung | |
| CH634567A5 (de) | Verfahren zur herstellung von uracilderivaten. | |
| DE2022746A1 (de) | Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren Herstellung | |
| DE1670168C3 (de) | 2-Benzolsulfonamido-4-methyl-5alkyl-pyrimidine und Verfahren zu ihrer Herstellung | |
| DE2427272C3 (de) | 1-(2-(β-Naphthyloxy)-äthyl)-3-methyl -pyrazolon-(5), Verfahren sowie Verwendung als Antithrombotikum | |
| CH513180A (de) | Verfahren zur Herstellung antidiabetisch wirksamer Sulfonamide | |
| DE946804C (de) | Verfahren zur Herstellung von schwefelhaltigen Abkoemmlingen der Barbitursaeure | |
| DE1445531C3 (de) | In 5 Stellung substituierte 2 Benzol sulfonamidopynmidine und Verfahren zu deren Herstellung | |
| AT332881B (de) | Verfahren zur herstellung des neuen n-(4-(beta- (2-methoxy-5-chlor-benzamido) -athyl)-benzolsulfonyl) -n'-cyclopentylharnstoffs und seiner salze | |
| DE1670282C3 (de) | Antidiabetisch wirksame Hydrindensulfonylamino-pyrimidine sowie Verfahren zu deren Herstellung | |
| DE2250469A1 (de) | Verfahren zur herstellung von substituierten benzimidazolen | |
| DE2911492C2 (de) | 5-Substituierte Picolinsäuren, deren Natrium-, Kalium-, Magnesium-, Calcium- und Aluminiumsalze, 5-Indanylester und Säureamide Verfahren zu deren Herstellung und antihypertonische Mittel, welche diese enthalten | |
| DE1445505C3 (de) | Im Phenylkern substituierte 2-Phenylamino-13-diazacyclopentene-(2) | |
| DE1745780C3 (de) | l-Sulfonyläthyl^-methyl-S-nitroimidazole und Verfahren zu ihrer Herstellung | |
| DE2942643C2 (de) | Thienyl(2)-carbonylphenoxyessigsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| AT236407B (de) | Verfahren zur Herstellung von neuen Benzolsulfonyl-alkylen-semicarbaziden | |
| DE1695914C3 (de) | Verfahren zur Herstellung von 1 Di alkylaminoathyl 2 methyl 3 aryl 4 oxo 1,2,3,4 tetrahydrochinazolinen | |
| DE1200824B (de) | Verfahren zur Herstellung von 3, 5-Dioxo-triazolidinen | |
| AT235848B (de) | Verfahren zur Herstellung von neuen Benzolsulfonylalkylensemicarbaziden | |
| DE2048906A1 (de) | Blutzuckersenkende Sulfonylaminopyrimidine und Verfahren zu deren Herstellung | |
| DE1901076A1 (de) | Antidiabetisch wirksame Sulfonylaminopyrimidine und Verfahren zu deren Herstellung | |
| DE1668199B2 (de) | Benzolsulfonyl-3-(2-hydroxycyclohexyl)harnstoffe | |
| DE2135805A1 (de) | Blutzuckersenkende sulfonylharnstoffe und sulfonylsemicarbazide und verfahren zu deren herstellung | |
| AT331809B (de) | Verfahren zur herstellung von neuen benzolsulfonylharnstoffen | |
| DE1493567C3 (de) | Ester von alpha-Alkylthyroxinderivaten und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |