DE2442851A1 - Basisch substituierte 3-sulfamoylbenzoesaeurederivate und verfahren zu ihrer herstellung - Google Patents
Basisch substituierte 3-sulfamoylbenzoesaeurederivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2442851A1 DE2442851A1 DE2442851A DE2442851A DE2442851A1 DE 2442851 A1 DE2442851 A1 DE 2442851A1 DE 2442851 A DE2442851 A DE 2442851A DE 2442851 A DE2442851 A DE 2442851A DE 2442851 A1 DE2442851 A1 DE 2442851A1
- Authority
- DE
- Germany
- Prior art keywords
- radicals
- acid
- general formula
- carbon atoms
- alkyl
- 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
- 239000002253 acid Substances 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 15
- -1 monounsaturated alkyl radical Chemical class 0.000 claims description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- NAETXYOXMDYNLE-UHFFFAOYSA-N 3-sulfamoylbenzoic acid Chemical class NS(=O)(=O)C1=CC=CC(C(O)=O)=C1 NAETXYOXMDYNLE-UHFFFAOYSA-N 0.000 claims description 7
- 125000005521 carbonamide group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000001153 fluoro group Chemical class F* 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- NJSJBTVAKUBCKG-UHFFFAOYSA-N propylazanide Chemical compound CCC[NH-] NJSJBTVAKUBCKG-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 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 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- JINHRCIIIZUAHL-UHFFFAOYSA-N 3-(diethylsulfamoyl)-4-(4-methylpiperazin-1-yl)benzoic acid Chemical compound CCN(CC)S(=O)(=O)C1=CC(C(O)=O)=CC=C1N1CCN(C)CC1 JINHRCIIIZUAHL-UHFFFAOYSA-N 0.000 description 2
- GCLKEAVEYRTOIE-UHFFFAOYSA-N 3-(dimethylsulfamoyl)-4-(4-methylpiperazin-1-yl)benzoic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=CC=C1N1CCN(C)CC1 GCLKEAVEYRTOIE-UHFFFAOYSA-N 0.000 description 2
- ZAGQFLZTAPIZOI-UHFFFAOYSA-N 3-(dimethylsulfamoyl)-4-(4-methylpiperazin-1-yl)benzoyl chloride;hydrochloride Chemical compound Cl.CN(C)S(=O)(=O)C1=CC(C(Cl)=O)=CC=C1N1CCN(C)CC1 ZAGQFLZTAPIZOI-UHFFFAOYSA-N 0.000 description 2
- YMPQIPORTHDIJK-UHFFFAOYSA-N 4-chloro-3-(dimethylsulfamoyl)benzoic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=CC=C1Cl YMPQIPORTHDIJK-UHFFFAOYSA-N 0.000 description 2
- QUGATESWYVRCPQ-UHFFFAOYSA-N 5-cyano-2-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound C1CN(C)CCN1C1=CC=C(C#N)C=C1S(N)(=O)=O QUGATESWYVRCPQ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- CSCFNOKJIMTZSC-UHFFFAOYSA-N benzoyl chloride;hydrochloride Chemical compound Cl.ClC(=O)C1=CC=CC=C1 CSCFNOKJIMTZSC-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 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 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
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- YKSVXVKIYYQWBB-UHFFFAOYSA-N 1-butylpiperazine Chemical compound CCCCN1CCNCC1 YKSVXVKIYYQWBB-UHFFFAOYSA-N 0.000 description 1
- UTTXEYODTTZTMS-UHFFFAOYSA-N 1-piperidin-1-yl-2-pyrrolidin-1-ylazepane Chemical compound C1CCCN1C1N(N2CCCCC2)CCCCC1 UTTXEYODTTZTMS-UHFFFAOYSA-N 0.000 description 1
- QLEIDMAURCRVCX-UHFFFAOYSA-N 1-propylpiperazine Chemical compound CCCN1CCNCC1 QLEIDMAURCRVCX-UHFFFAOYSA-N 0.000 description 1
- NAGGYODWMPFKJQ-UHFFFAOYSA-N 2,4-dibromobenzoic acid Chemical class OC(=O)C1=CC=C(Br)C=C1Br NAGGYODWMPFKJQ-UHFFFAOYSA-N 0.000 description 1
- AXZYPNJQDXTQDX-UHFFFAOYSA-N 2-chloro-4-(4-methylpiperazin-1-yl)-5-morpholin-4-ylsulfonylbenzoic acid Chemical compound C1CN(C)CCN1C1=CC(Cl)=C(C(O)=O)C=C1S(=O)(=O)N1CCOCC1 AXZYPNJQDXTQDX-UHFFFAOYSA-N 0.000 description 1
- PNQXIKJSXNXDRP-UHFFFAOYSA-N 2-chloro-4-(4-methylpiperazin-1-yl)-5-sulfamoylbenzoic acid Chemical compound C1CN(C)CCN1C1=CC(Cl)=C(C(O)=O)C=C1S(N)(=O)=O PNQXIKJSXNXDRP-UHFFFAOYSA-N 0.000 description 1
- DDGOQDDPEWYVRD-UHFFFAOYSA-N 2-chloro-4-fluoro-5-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=C(Cl)C=C1F DDGOQDDPEWYVRD-UHFFFAOYSA-N 0.000 description 1
- KGGYATOAILBNDO-UHFFFAOYSA-N 2-chloro-5-(morpholine-4-carbonyl)benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)N2CCOCC2)=C1 KGGYATOAILBNDO-UHFFFAOYSA-N 0.000 description 1
- XTPRSWPAZJPVMR-UHFFFAOYSA-N 2-hydroxyethylazanide Chemical compound [NH-]CCO XTPRSWPAZJPVMR-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- IESFUTGXHOYJGK-UHFFFAOYSA-N 3-(dimethylsulfamoyl)-4-(4-methylpiperazin-1-yl)benzoic acid;hydrochloride Chemical compound Cl.CN(C)S(=O)(=O)C1=CC(C(O)=O)=CC=C1N1CCN(C)CC1 IESFUTGXHOYJGK-UHFFFAOYSA-N 0.000 description 1
- YTTMBLVRHYUNOB-UHFFFAOYSA-N 3-(dimethylsulfamoyl)-4-piperazin-1-ylbenzoic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=CC=C1N1CCNCC1 YTTMBLVRHYUNOB-UHFFFAOYSA-N 0.000 description 1
- YUNBIUJUMSZKKE-UHFFFAOYSA-N 3-[benzyl(methyl)sulfamoyl]-4-chlorobenzoic acid Chemical compound C=1C(C(O)=O)=CC=C(Cl)C=1S(=O)(=O)N(C)CC1=CC=CC=C1 YUNBIUJUMSZKKE-UHFFFAOYSA-N 0.000 description 1
- WRVZKMDKLOPOMW-UHFFFAOYSA-N 4-(4-benzylpiperazin-1-yl)-3-(dimethylsulfamoyl)benzoic acid;hydrobromide Chemical compound Br.CN(C)S(=O)(=O)C1=CC(C(O)=O)=CC=C1N1CCN(CC=2C=CC=CC=2)CC1 WRVZKMDKLOPOMW-UHFFFAOYSA-N 0.000 description 1
- PRBYWFODNDADRW-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-3-(phenylsulfamoyl)benzoic acid Chemical compound C1CN(C)CCN1C1=CC=C(C(O)=O)C=C1S(=O)(=O)NC1=CC=CC=C1 PRBYWFODNDADRW-UHFFFAOYSA-N 0.000 description 1
- ZHHNWASIWYQHCO-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-3-piperidin-1-ylsulfonylbenzamide Chemical compound C1CN(C)CCN1C1=CC=C(C(N)=O)C=C1S(=O)(=O)N1CCCCC1 ZHHNWASIWYQHCO-UHFFFAOYSA-N 0.000 description 1
- AYYWKZIJRQMSHH-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-3-piperidin-1-ylsulfonylbenzoic acid Chemical compound C1CN(C)CCN1C1=CC=C(C(O)=O)C=C1S(=O)(=O)N1CCCCC1 AYYWKZIJRQMSHH-UHFFFAOYSA-N 0.000 description 1
- GGWZNVXXOLBCER-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-3-piperidin-1-ylsulfonylbenzoic acid;hydrochloride Chemical compound Cl.C1CN(C)CCN1C1=CC=C(C(O)=O)C=C1S(=O)(=O)N1CCCCC1 GGWZNVXXOLBCER-UHFFFAOYSA-N 0.000 description 1
- IFRUAQMWPPXPOS-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-3-pyrrolidin-1-ylsulfonylbenzoic acid;hydrochloride Chemical compound Cl.C1CN(C)CCN1C1=CC=C(C(O)=O)C=C1S(=O)(=O)N1CCCC1 IFRUAQMWPPXPOS-UHFFFAOYSA-N 0.000 description 1
- CIFZXJWEIKCTER-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-3-sulfamoylbenzamide Chemical compound C1CN(C)CCN1C1=CC=C(C(N)=O)C=C1S(N)(=O)=O CIFZXJWEIKCTER-UHFFFAOYSA-N 0.000 description 1
- NEQONZJBWNSLLQ-UHFFFAOYSA-N 4-chloro-2-methyl-5-sulfamoylbenzoic acid Chemical compound CC1=CC(Cl)=C(S(N)(=O)=O)C=C1C(O)=O NEQONZJBWNSLLQ-UHFFFAOYSA-N 0.000 description 1
- OANXBFKRXPGEGI-UHFFFAOYSA-N 4-chloro-3-(diethylsulfamoyl)benzoic acid Chemical compound CCN(CC)S(=O)(=O)C1=CC(C(O)=O)=CC=C1Cl OANXBFKRXPGEGI-UHFFFAOYSA-N 0.000 description 1
- VFIQUWGBANQKJT-UHFFFAOYSA-N 4-chloro-3-(methylsulfamoyl)benzoic acid Chemical compound CNS(=O)(=O)C1=CC(C(O)=O)=CC=C1Cl VFIQUWGBANQKJT-UHFFFAOYSA-N 0.000 description 1
- SSOMJRJEEVXYPJ-UHFFFAOYSA-N 4-chloro-3-(phenylsulfamoyl)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(S(=O)(=O)NC=2C=CC=CC=2)=C1 SSOMJRJEEVXYPJ-UHFFFAOYSA-N 0.000 description 1
- FHALQCKQZFYPGB-UHFFFAOYSA-N 4-chloro-3-morpholin-4-ylsulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(S(=O)(=O)N2CCOCC2)=C1 FHALQCKQZFYPGB-UHFFFAOYSA-N 0.000 description 1
- FCNJMGGLUGSOGL-UHFFFAOYSA-N 4-chloro-3-piperidin-1-ylsulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(S(=O)(=O)N2CCCCC2)=C1 FCNJMGGLUGSOGL-UHFFFAOYSA-N 0.000 description 1
- WRLKLPDTRUYBBV-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzamide Chemical compound NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 WRLKLPDTRUYBBV-UHFFFAOYSA-N 0.000 description 1
- FHQAWINGVCDTTG-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=CC=C1Cl FHQAWINGVCDTTG-UHFFFAOYSA-N 0.000 description 1
- JUDHEAJLYLDRNR-UHFFFAOYSA-N 4-chloro-n-(furan-2-ylmethyl)-n-methyl-3-sulfamoylbenzamide Chemical compound C=1C=C(Cl)C(S(N)(=O)=O)=CC=1C(=O)N(C)CC1=CC=CO1 JUDHEAJLYLDRNR-UHFFFAOYSA-N 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920006063 Lamide® Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000761456 Nops Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- HHRFWSALGNYPHA-UHFFFAOYSA-N [N].C1CNCCN1 Chemical compound [N].C1CNCCN1 HHRFWSALGNYPHA-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- QLTRHMKBZCXXDQ-UHFFFAOYSA-N benzyl 3-(dimethylsulfamoyl)-4-(4-methylpiperazin-1-yl)benzoate;hydrochloride Chemical compound Cl.CN(C)S(=O)(=O)C1=CC(C(=O)OCC=2C=CC=CC=2)=CC=C1N1CCN(C)CC1 QLTRHMKBZCXXDQ-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical class CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- GRUGFRGVVFXQHJ-UHFFFAOYSA-N ethyl 4-(4-methylpiperazin-1-yl)-3-sulfamoylbenzoate Chemical compound NS(=O)(=O)C1=CC(C(=O)OCC)=CC=C1N1CCN(C)CC1 GRUGFRGVVFXQHJ-UHFFFAOYSA-N 0.000 description 1
- KTUHQENNAFLKDE-UHFFFAOYSA-N ethyl 4-chloro-3-sulfamoylbenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 KTUHQENNAFLKDE-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BLIOIVSBJSKNHX-UHFFFAOYSA-N n,n-dibenzyl-3-(dimethylsulfamoyl)-4-(4-methylpiperazin-1-yl)benzamide Chemical compound CN(C)S(=O)(=O)C1=CC(C(=O)N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=C1N1CCN(C)CC1 BLIOIVSBJSKNHX-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- YHMSWIUKEZTQSF-UHFFFAOYSA-N n-benzyl-4-chloro-n-methyl-3-sulfamoylbenzamide Chemical compound C=1C=C(Cl)C(S(N)(=O)=O)=CC=1C(=O)N(C)CC1=CC=CC=C1 YHMSWIUKEZTQSF-UHFFFAOYSA-N 0.000 description 1
- OVCJJELYRSXPRX-UHFFFAOYSA-N n-benzyl-n-methyl-4-(4-methylpiperazin-1-yl)-3-sulfamoylbenzamide Chemical compound C=1C=C(N2CCN(C)CC2)C(S(N)(=O)=O)=CC=1C(=O)N(C)CC1=CC=CC=C1 OVCJJELYRSXPRX-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OOTKJPZEEVPWCR-UHFFFAOYSA-N n-methyl-1-pyridin-2-ylmethanamine Chemical class CNCC1=CC=CC=N1 OOTKJPZEEVPWCR-UHFFFAOYSA-N 0.000 description 1
- OJSDIMLQIDMVNL-UHFFFAOYSA-N n-methylfuran-2-amine Chemical compound CNC1=CC=CO1 OJSDIMLQIDMVNL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 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 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2442851A DE2442851A1 (de) | 1974-09-06 | 1974-09-06 | Basisch substituierte 3-sulfamoylbenzoesaeurederivate und verfahren zu ihrer herstellung |
| NL7510287A NL7510287A (nl) | 1974-09-06 | 1975-09-01 | Werkwijze voor het bereiden van basisch gesubsti- tueerde 3-sulfamoylbenzoezuurderivaten. |
| ES440602A ES440602A1 (es) | 1974-09-06 | 1975-09-01 | Procedimiento para la preparacion de derivados de acido 3- sulfamoibenzoico sustituidos con radicales basicos. |
| FI752472A FI752472A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-06 | 1975-09-03 | |
| LU73330A LU73330A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-09-06 | 1975-09-04 | |
| US05/610,388 US4029787A (en) | 1974-09-06 | 1975-09-04 | Basically substituted 3-sulfamoylbenzoic acid derivatives and process for their preparation |
| IL48048A IL48048A0 (en) | 1974-09-06 | 1975-09-04 | Basically substituted 3-sulfamoylbenzoic acid derivatives and process for their preparation |
| FR7527352A FR2283683A1 (fr) | 1974-09-06 | 1975-09-05 | Derives d'acide 3-sulfamoylbenzoique a substituants basiques et leur procede de preparation |
| ZA00755688A ZA755688B (en) | 1974-09-06 | 1975-09-05 | Basically substituted 3-sulfamoylbenzoic acid derivatives and process for their preparation |
| DK399275A DK399275A (da) | 1974-09-06 | 1975-09-05 | Basisk substituerede 3-sulfamoylbenzoesyrederivater og fremgangsmade til deres fremstilling |
| SE7509897A SE7509897L (sv) | 1974-09-06 | 1975-09-05 | Basiskt substituerade 3-sulfamoylbensoesyraderivat och forfarande for deras framstellning |
| JP50107580A JPS5154574A (en) | 1974-09-06 | 1975-09-06 | Enkiseichikan 33 surufuamoiruansokukosanjudotainoseiho |
| BE159840A BE833184A (fr) | 1974-09-06 | 1975-09-08 | Derives d'acide 3-sulfamoylbenzoique a substants basiques et leur procede de preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2442851A DE2442851A1 (de) | 1974-09-06 | 1974-09-06 | Basisch substituierte 3-sulfamoylbenzoesaeurederivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2442851A1 true DE2442851A1 (de) | 1976-03-18 |
Family
ID=5925106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2442851A Pending DE2442851A1 (de) | 1974-09-06 | 1974-09-06 | Basisch substituierte 3-sulfamoylbenzoesaeurederivate und verfahren zu ihrer herstellung |
Country Status (13)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999002502A3 (en) * | 1997-07-11 | 1999-06-03 | Smithkline Beecham Plc | Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1176613B (it) * | 1984-08-14 | 1987-08-18 | Ravizza Spa | Derivati piperazinici farmacologicamente attivi e processo per la loro preparazione |
| US7544676B2 (en) * | 2005-11-10 | 2009-06-09 | Adolor Corporation | Sulfamoyl benzamides and methods of their use |
| EP2487169B1 (en) * | 2007-08-21 | 2015-05-20 | Senomyx, Inc. | Compounds that inhibit (block) bitter taste in compositions and use thereof |
| US8076491B2 (en) | 2007-08-21 | 2011-12-13 | Senomyx, Inc. | Compounds that inhibit (block) bitter taste in composition and use thereof |
| SG11202110950XA (en) * | 2019-04-02 | 2021-10-28 | Fondazione St Italiano Tecnologia | Modulators of intracellular chloride concentration |
-
1974
- 1974-09-06 DE DE2442851A patent/DE2442851A1/de active Pending
-
1975
- 1975-09-01 NL NL7510287A patent/NL7510287A/xx unknown
- 1975-09-01 ES ES440602A patent/ES440602A1/es not_active Expired
- 1975-09-03 FI FI752472A patent/FI752472A7/fi not_active Application Discontinuation
- 1975-09-04 US US05/610,388 patent/US4029787A/en not_active Expired - Lifetime
- 1975-09-04 LU LU73330A patent/LU73330A1/xx unknown
- 1975-09-04 IL IL48048A patent/IL48048A0/xx unknown
- 1975-09-05 DK DK399275A patent/DK399275A/da unknown
- 1975-09-05 FR FR7527352A patent/FR2283683A1/fr active Granted
- 1975-09-05 ZA ZA00755688A patent/ZA755688B/xx unknown
- 1975-09-05 SE SE7509897A patent/SE7509897L/xx unknown
- 1975-09-06 JP JP50107580A patent/JPS5154574A/ja active Pending
- 1975-09-08 BE BE159840A patent/BE833184A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999002502A3 (en) * | 1997-07-11 | 1999-06-03 | Smithkline Beecham Plc | Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| DK399275A (da) | 1976-03-07 |
| JPS5154574A (en) | 1976-05-13 |
| US4029787A (en) | 1977-06-14 |
| FI752472A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-03-07 |
| IL48048A0 (en) | 1975-11-25 |
| ZA755688B (en) | 1976-08-25 |
| LU73330A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-11 |
| BE833184A (fr) | 1976-03-08 |
| FR2283683B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-07-28 |
| NL7510287A (nl) | 1976-03-09 |
| ES440602A1 (es) | 1977-03-01 |
| FR2283683A1 (fr) | 1976-04-02 |
| SE7509897L (sv) | 1976-03-08 |
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