NO123388B - - Google Patents
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- Publication number
- NO123388B NO123388B NO5146/68A NO514668A NO123388B NO 123388 B NO123388 B NO 123388B NO 5146/68 A NO5146/68 A NO 5146/68A NO 514668 A NO514668 A NO 514668A NO 123388 B NO123388 B NO 123388B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- reacted
- methoxy
- general formula
- chloroanilide
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 40
- -1 lower alkenoxy Chemical group 0.000 claims description 13
- 239000008280 blood Substances 0.000 claims description 11
- 210000004369 blood Anatomy 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000003456 sulfonamides Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 229940124530 sulfonamide Drugs 0.000 claims description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- VQEHSBSZLWUDML-UHFFFAOYSA-N 2-chloro-5-(2-methylpropyl)pyrimidine Chemical compound CC(C)CC1=CN=C(Cl)N=C1 VQEHSBSZLWUDML-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical class O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 229940118019 malondialdehyde Drugs 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- ZINCSSQSZVBPDS-UHFFFAOYSA-N 2-chloro-5-propan-2-yloxypyrimidine Chemical compound CC(C)OC1=CN=C(Cl)N=C1 ZINCSSQSZVBPDS-UHFFFAOYSA-N 0.000 claims 1
- YAKIJEZSDKOGGQ-UHFFFAOYSA-N 5-(2-methylpropyl)pyrimidin-2-amine Chemical compound CC(C)CC1=CN=C(N)N=C1 YAKIJEZSDKOGGQ-UHFFFAOYSA-N 0.000 claims 1
- UVVXVOXBBHGUIX-UHFFFAOYSA-N 5-propan-2-yloxypyrimidin-2-amine Chemical compound CC(C)OC1=CN=C(N)N=C1 UVVXVOXBBHGUIX-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229960003424 phenylacetic acid Drugs 0.000 description 4
- 239000003279 phenylacetic acid Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- FNXYWHTZDAVRTB-UHFFFAOYSA-N 3-methyl-1,2-oxazol-5-amine Chemical compound CC=1C=C(N)ON=1 FNXYWHTZDAVRTB-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- UYFXWXGHKHSRMK-UHFFFAOYSA-N COC(C=CC(Cl)=C1)=C1NC(CC(C=C1)=CC=C1S(Cl)(=O)=O)=O Chemical compound COC(C=CC(Cl)=C1)=C1NC(CC(C=C1)=CC=C1S(Cl)(=O)=O)=O UYFXWXGHKHSRMK-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- UQBLCEMTGKJIPI-UHFFFAOYSA-N N-[2-(5-methoxypyrimidin-2-yl)oxyethyl]benzenesulfonamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NCCOC1=NC=C(C=N1)OC UQBLCEMTGKJIPI-UHFFFAOYSA-N 0.000 description 2
- YSOMTIHBNLYURM-UHFFFAOYSA-N NC1=NC=C(C=N1)SC(C)C Chemical compound NC1=NC=C(C=N1)SC(C)C YSOMTIHBNLYURM-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- MEYLZWCRIMFXNG-UHFFFAOYSA-N 1,1-diethoxy-2-ethylsulfanylethane Chemical compound CCOC(OCC)CSCC MEYLZWCRIMFXNG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- ADSHNWROWDRQOX-UHFFFAOYSA-N 5-(2,2-dimethylpropyl)pyrimidin-2-amine Chemical compound CC(C)(C)CC1=CN=C(N)N=C1 ADSHNWROWDRQOX-UHFFFAOYSA-N 0.000 description 1
- FHVPUBOGJQUCQQ-UHFFFAOYSA-N 5-(2-methylpropyl)-2-methylsulfonylpyrimidine Chemical compound CC(C)CC1=CN=C(S(C)(=O)=O)N=C1 FHVPUBOGJQUCQQ-UHFFFAOYSA-N 0.000 description 1
- CXDAPRCYUQYNCC-UHFFFAOYSA-N 5-ethylsulfanylpyrimidin-2-amine Chemical compound C(C)SC=1C=NC(=NC1)N CXDAPRCYUQYNCC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 229960004111 buformin Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- NUQDEHHKOXSIEA-UHFFFAOYSA-N glymidine sodium Chemical compound [Na+].N1=CC(OCCOC)=CN=C1[N-]S(=O)(=O)C1=CC=CC=C1 NUQDEHHKOXSIEA-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1695855A DE1695855C3 (de) | 1967-12-30 | 1967-12-30 | 4-(5-Isobutyl-2-pyrimidinyl)-sulfonamidophenylessigsäure-(2-methoxy-5chloranilid) und dessen Salze mit physiologisch verträglichen Basen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123388B true NO123388B (es) | 1971-11-08 |
Family
ID=7436399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO5146/68A NO123388B (es) | 1967-12-30 | 1968-12-23 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3621026A (es) |
| AT (4) | AT281848B (es) |
| BE (1) | BE726253A (es) |
| BG (1) | BG15214A3 (es) |
| BR (1) | BR6805262D0 (es) |
| CH (1) | CH562218A5 (es) |
| CS (5) | CS151493B2 (es) |
| DE (1) | DE1695855C3 (es) |
| DK (1) | DK119663B (es) |
| FI (1) | FI51182C (es) |
| FR (2) | FR1599571A (es) |
| GB (1) | GB1254720A (es) |
| IE (1) | IE32495B1 (es) |
| IL (1) | IL31024A (es) |
| NL (1) | NL159581B (es) |
| NO (1) | NO123388B (es) |
| SE (1) | SE358391B (es) |
| YU (1) | YU35359B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3878212A (en) * | 1970-04-28 | 1975-04-15 | Clemens Rufer | Blood sugar lowering sulfamoyl pyrimidines and asymmetrical carbon atom |
| DE2021962C3 (de) * | 1970-04-28 | 1981-12-24 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Blutzuckersenkende Sulfamoylpyrimidine mit asymmetrischem Kohlenstoffatom |
| DE2150279C2 (de) * | 1971-10-05 | 1983-08-25 | Schering AG, 1000 Berlin und 4709 Bergkamen | Blutzuckersenkende Sulfamoylpyrimidine mit asymmetrischem Kohlenstoffatom |
| US3878213A (en) * | 1971-03-31 | 1975-04-15 | Hanns Ahrens | Certain 4-(n-pyrimidin-2-ylsulfamoyl)-phenylacetamides |
| US3829434A (en) * | 1972-11-10 | 1974-08-13 | Pfizer | Piperidinesulfonylurea derivatives |
| DE2401879A1 (de) * | 1974-01-16 | 1975-07-24 | Hoechst Ag | Benzolsulfonamidopyrimidine und verfahren zu ihrer herstellung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL129627C (es) * | 1964-05-20 |
-
1967
- 1967-12-30 DE DE1695855A patent/DE1695855C3/de not_active Expired
-
1968
- 1968-09-08 YU YU2089/68A patent/YU35359B/xx unknown
- 1968-09-10 CH CH1863970A patent/CH562218A5/xx not_active IP Right Cessation
- 1968-09-13 FI FI682581A patent/FI51182C/fi active
- 1968-09-17 AT AT07003/69A patent/AT281848B/de not_active IP Right Cessation
- 1968-09-17 AT AT07000/69A patent/AT281845B/de not_active IP Right Cessation
- 1968-09-17 AT AT907368A patent/AT281835B/de not_active IP Right Cessation
- 1968-09-17 AT AT07001/69A patent/AT281846B/de not_active IP Right Cessation
- 1968-09-27 DK DK468468AA patent/DK119663B/da not_active IP Right Cessation
- 1968-10-16 BG BG012210A patent/BG15214A3/bg unknown
- 1968-11-06 IL IL31024A patent/IL31024A/xx unknown
- 1968-11-19 IE IE1397/68A patent/IE32495B1/xx unknown
- 1968-12-17 CS CS222*[A patent/CS151493B2/cs unknown
- 1968-12-17 CS CS221*[A patent/CS151492B2/cs unknown
- 1968-12-17 CS CS223*[A patent/CS151494B2/cs unknown
- 1968-12-17 CS CS8551A patent/CS151490B2/cs unknown
- 1968-12-17 CS CS220*[A patent/CS151491B2/cs unknown
- 1968-12-19 US US786548A patent/US3621026A/en not_active Expired - Lifetime
- 1968-12-20 GB GB60767/68A patent/GB1254720A/en not_active Expired
- 1968-12-23 NO NO5146/68A patent/NO123388B/no unknown
- 1968-12-30 FR FR1599571D patent/FR1599571A/fr not_active Expired
- 1968-12-30 BE BE726253D patent/BE726253A/xx unknown
- 1968-12-30 SE SE18013/68A patent/SE358391B/xx unknown
- 1968-12-30 NL NL6818838.A patent/NL159581B/xx not_active IP Right Cessation
- 1968-12-30 BR BR205262/68A patent/BR6805262D0/pt unknown
-
1969
- 1969-03-28 FR FR183308A patent/FR8288M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CS151493B2 (es) | 1973-10-19 |
| BG15214A3 (bg) | 1975-09-05 |
| YU208968A (en) | 1980-06-30 |
| IE32495B1 (en) | 1973-08-22 |
| AT281845B (de) | 1970-06-10 |
| US3621026A (en) | 1971-11-16 |
| CS151494B2 (es) | 1973-10-19 |
| DE1695855B2 (de) | 1978-11-16 |
| IE32495L (en) | 1969-06-30 |
| FR8288M (es) | 1970-11-09 |
| BE726253A (es) | 1969-06-30 |
| NL6818838A (es) | 1969-07-02 |
| SE358391B (es) | 1973-07-30 |
| BR6805262D0 (pt) | 1973-02-13 |
| FR1599571A (es) | 1970-07-15 |
| AT281848B (de) | 1970-06-10 |
| CS151491B2 (es) | 1973-10-19 |
| GB1254720A (en) | 1971-11-24 |
| IL31024A0 (en) | 1969-01-29 |
| DE1695855C3 (de) | 1979-07-12 |
| YU35359B (en) | 1980-12-31 |
| FI51182B (es) | 1976-08-02 |
| CS151492B2 (es) | 1973-10-19 |
| DE1695855A1 (de) | 1971-05-13 |
| NL159581B (nl) | 1979-03-15 |
| CH562218A5 (es) | 1975-05-30 |
| AT281835B (de) | 1970-06-10 |
| IL31024A (en) | 1972-10-29 |
| DK119663B (da) | 1971-02-08 |
| FI51182C (fi) | 1976-11-10 |
| CS151490B2 (es) | 1973-10-19 |
| AT281846B (de) | 1970-06-10 |
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