CH616921A5 - - Google Patents
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- CH616921A5 CH616921A5 CH181279A CH181279A CH616921A5 CH 616921 A5 CH616921 A5 CH 616921A5 CH 181279 A CH181279 A CH 181279A CH 181279 A CH181279 A CH 181279A CH 616921 A5 CH616921 A5 CH 616921A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- formula
- compound
- carbon atoms
- hydrogen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 43
- -1 hydroxy, amino Chemical group 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 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 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 241000251730 Chondrichthyes Species 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000007257 deesterification reaction Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 33
- 238000002844 melting Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000002841 Lewis acid Substances 0.000 description 11
- 150000007517 lewis acids Chemical class 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- UJEWTUDSLQGTOA-UHFFFAOYSA-N Piretanide Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 UJEWTUDSLQGTOA-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 229960004050 aminobenzoic acid Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002934 diuretic Substances 0.000 description 4
- 229940030606 diuretics Drugs 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- WSDGTEVEZCDJGX-UHFFFAOYSA-N methyl 3-amino-4-phenoxy-5-pyrrolidin-1-ylbenzoate Chemical compound C1CCCN1C1=CC(C(=O)OC)=CC(N)=C1OC1=CC=CC=C1 WSDGTEVEZCDJGX-UHFFFAOYSA-N 0.000 description 3
- WYUJUHDZHVCFGK-UHFFFAOYSA-N methyl 4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoate Chemical compound C=1C=CC=CC=1OC=1C(S(N)(=O)=O)=CC(C(=O)OC)=CC=1N1CCCC1 WYUJUHDZHVCFGK-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000000894 saliuretic effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical class NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 description 2
- QFZHYXHTUFZHOZ-UHFFFAOYSA-N 3-amino-4-phenoxy-5-pyrrolidin-1-ylbenzoic acid Chemical compound C=1C=CC=CC=1OC=1C(N)=CC(C(O)=O)=CC=1N1CCCC1 QFZHYXHTUFZHOZ-UHFFFAOYSA-N 0.000 description 2
- QCPLUUVFRFVGDJ-UHFFFAOYSA-N 3-nitro-4-phenoxy-5-pyrrolidin-1-ylbenzoic acid Chemical compound C=1C=CC=CC=1OC=1C([N+]([O-])=O)=CC(C(=O)O)=CC=1N1CCCC1 QCPLUUVFRFVGDJ-UHFFFAOYSA-N 0.000 description 2
- SZSJZOHUWPLSNK-UHFFFAOYSA-N 4-(4-aminophenoxy)-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid Chemical compound C1=CC(N)=CC=C1OC1=C(N2CCCC2)C=C(C(O)=O)C=C1S(N)(=O)=O SZSJZOHUWPLSNK-UHFFFAOYSA-N 0.000 description 2
- HBBNLOSHGSHJIA-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid Chemical compound C=1C=C(O)C=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 HBBNLOSHGSHJIA-UHFFFAOYSA-N 0.000 description 2
- PEYSEJDTZLYIOL-UHFFFAOYSA-N 4-(benzenesulfinyl)-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1S(=O)C=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 PEYSEJDTZLYIOL-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000005621 boronate group Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- ZKYCAYQUHKVHIR-UHFFFAOYSA-N methyl 3,5-dinitro-4-phenoxybenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC([N+]([O-])=O)=C1OC1=CC=CC=C1 ZKYCAYQUHKVHIR-UHFFFAOYSA-N 0.000 description 2
- PRPWLZLYDBMMOO-UHFFFAOYSA-N methyl 3-chlorosulfonyl-4-phenoxy-5-pyrrolidin-1-ylbenzoate Chemical compound C=1C=CC=CC=1OC=1C(S(Cl)(=O)=O)=CC(C(=O)OC)=CC=1N1CCCC1 PRPWLZLYDBMMOO-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KBCPMQUSOLSAQO-UHFFFAOYSA-N (4-carboxyphenyl)azanium;chloride Chemical compound Cl.NC1=CC=C(C(O)=O)C=C1 KBCPMQUSOLSAQO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DHZZPKMVVSTYLF-UHFFFAOYSA-N 2-(2-methylanilino)ethanol Chemical compound CC1=CC=CC=C1NCCO DHZZPKMVVSTYLF-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- CJAUDLWNVJOQNN-UHFFFAOYSA-N 2-aminobenzoic acid;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=CC=CC=C1C(O)=O CJAUDLWNVJOQNN-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- FGMRHNYMZYMARX-UHFFFAOYSA-N 3-amino-2-nitrobenzoic acid Chemical class NC1=CC=CC(C(O)=O)=C1[N+]([O-])=O FGMRHNYMZYMARX-UHFFFAOYSA-N 0.000 description 1
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
- WLJHSASKFIZYOP-UHFFFAOYSA-N 3-chlorosulfonyl-4-phenoxy-5-pyrrolidin-1-ylbenzoic acid Chemical compound C=1C=CC=CC=1OC=1C(S(Cl)(=O)=O)=CC(C(=O)O)=CC=1N1CCCC1 WLJHSASKFIZYOP-UHFFFAOYSA-N 0.000 description 1
- OGJGERJACOUQCB-UHFFFAOYSA-N 4-(benzenesulfonyl)-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1S(=O)(=O)C=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 OGJGERJACOUQCB-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- NMUISIINDFJKPE-UHFFFAOYSA-N 4-benzyl-3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=CC=C1CC1=CC=CC=C1 NMUISIINDFJKPE-UHFFFAOYSA-N 0.000 description 1
- CGIGUVDFQZKUBN-UHFFFAOYSA-N 4-phenoxy-3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=CC=C1OC1=CC=CC=C1 CGIGUVDFQZKUBN-UHFFFAOYSA-N 0.000 description 1
- GPVVBCYRRBLXDU-UHFFFAOYSA-N 4-phenyl-3-pyrrolidin-1-yl-5-sulfamoyl-2-sulfooxybenzoic acid Chemical compound C=1C=CC=CC=1C=1C(S(=O)(=O)N)=CC(C(O)=O)=C(OS(O)(=O)=O)C=1N1CCCC1 GPVVBCYRRBLXDU-UHFFFAOYSA-N 0.000 description 1
- GQLRJHUVILNIPL-UHFFFAOYSA-N 4-phenylsulfanyl-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1SC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 GQLRJHUVILNIPL-UHFFFAOYSA-N 0.000 description 1
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940064734 aminobenzoate Drugs 0.000 description 1
- 150000005417 aminobenzoic acid derivatives Chemical class 0.000 description 1
- 235000011162 ammonium carbonates Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229960001523 chlortalidone Drugs 0.000 description 1
- JIVPVXMEBJLZRO-UHFFFAOYSA-N chlorthalidone Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- CKQQMPJQZXIYMJ-UHFFFAOYSA-N dihydrate;dihydrochloride Chemical compound O.O.Cl.Cl CKQQMPJQZXIYMJ-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- CBBVHSHLSCZIHD-UHFFFAOYSA-N mercury silver Chemical compound [Ag].[Hg] CBBVHSHLSCZIHD-UHFFFAOYSA-N 0.000 description 1
- AOXPHVNMBPFOFS-UHFFFAOYSA-N methyl 2-nitrobenzoate Chemical compound COC(=O)C1=CC=CC=C1[N+]([O-])=O AOXPHVNMBPFOFS-UHFFFAOYSA-N 0.000 description 1
- WXGYZMSGMPFLPV-UHFFFAOYSA-N methyl 3,5-diamino-4-phenoxybenzoate Chemical compound NC1=CC(C(=O)OC)=CC(N)=C1OC1=CC=CC=C1 WXGYZMSGMPFLPV-UHFFFAOYSA-N 0.000 description 1
- DLSFAHCVNTZNFC-UHFFFAOYSA-N methyl 3-amino-4-phenoxybenzoate Chemical compound NC1=CC(C(=O)OC)=CC=C1OC1=CC=CC=C1 DLSFAHCVNTZNFC-UHFFFAOYSA-N 0.000 description 1
- UMIJEMFJEZCPQS-UHFFFAOYSA-N methyl 3-amino-5-nitro-4-phenoxybenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC(N)=C1OC1=CC=CC=C1 UMIJEMFJEZCPQS-UHFFFAOYSA-N 0.000 description 1
- VZDNXXPBYLGWOS-UHFFFAOYSA-N methyl 3-aminobenzoate Chemical compound COC(=O)C1=CC=CC(N)=C1 VZDNXXPBYLGWOS-UHFFFAOYSA-N 0.000 description 1
- SQIBNKUEUWGZBH-UHFFFAOYSA-N methyl 3-chlorosulfonylbenzoate Chemical compound COC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 SQIBNKUEUWGZBH-UHFFFAOYSA-N 0.000 description 1
- XRYAKSDEOMNYOF-UHFFFAOYSA-N methyl 3-nitro-4-phenoxy-5-pyrrolidin-1-ylbenzoate Chemical compound C=1C=CC=CC=1OC=1C([N+]([O-])=O)=CC(C(=O)OC)=CC=1N1CCCC1 XRYAKSDEOMNYOF-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000000054 salidiuretic effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/45—Non condensed piperidines, e.g. piperocaine having oxo groups directly attached to the heterocyclic ring, e.g. cycloheximide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
-
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
- C07D265/33—Two oxygen atoms, in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2419970A DE2419970C3 (de) | 1974-04-25 | 1974-04-25 | 3-<l-Pyrrolidinyl)-4-phenoxy-5sulfamoylbenzoesäure und Verfahren zu ihrer Herstellung |
DE2461601A DE2461601C2 (de) | 1974-04-25 | 1974-12-27 | 3-Pyrrolidino-4-phenoxy-5-sulfamoylbenzoesäureester und Verfahren zu ihrer Herstellung |
AU46290/79A AU521892B2 (en) | 1974-04-25 | 1979-04-19 | Sulphamoylbenzoic acid derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
CH616921A5 true CH616921A5 (en, 2012) | 1980-04-30 |
Family
ID=27154410
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH510175A CH615910A5 (en, 2012) | 1974-04-25 | 1975-04-22 | |
CH181479A CH616923A5 (en, 2012) | 1974-04-25 | 1979-02-23 | |
CH181279A CH616921A5 (en, 2012) | 1974-04-25 | 1979-02-23 | |
CH181379A CH616922A5 (en, 2012) | 1974-04-25 | 1979-02-23 | |
CH1064079A CH620677A5 (en, 2012) | 1974-04-25 | 1979-11-29 |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH510175A CH615910A5 (en, 2012) | 1974-04-25 | 1975-04-22 | |
CH181479A CH616923A5 (en, 2012) | 1974-04-25 | 1979-02-23 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH181379A CH616922A5 (en, 2012) | 1974-04-25 | 1979-02-23 | |
CH1064079A CH620677A5 (en, 2012) | 1974-04-25 | 1979-11-29 |
Country Status (14)
Country | Link |
---|---|
US (1) | US4010273A (en, 2012) |
JP (1) | JPS624385B2 (en, 2012) |
AT (1) | AT356091B (en, 2012) |
AU (1) | AU521892B2 (en, 2012) |
BE (1) | BE828441A (en, 2012) |
CA (1) | CA1039734A (en, 2012) |
CH (5) | CH615910A5 (en, 2012) |
DE (2) | DE2419970C3 (en, 2012) |
FR (1) | FR2324298A1 (en, 2012) |
GB (1) | GB1504505A (en, 2012) |
LU (1) | LU72348A1 (en, 2012) |
NL (1) | NL188410C (en, 2012) |
OA (1) | OA04987A (en, 2012) |
SE (2) | SE425486B (en, 2012) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4093735A (en) * | 1974-04-25 | 1978-06-06 | Hoechst Aktiengesellschaft | 5-Sulfamoylbenzoic acid derivatives carrying a heterocyclic substituent |
NL7714062A (nl) * | 1976-12-24 | 1978-06-27 | Hoechst Ag | Werkwijze voor de bereiding van pyrrolo-benzoe- zuur-derivaten. |
CH628622A5 (de) * | 1976-12-24 | 1982-03-15 | Ciba Geigy Ag | Verfahren zur herstellung von neuen in 4-stellung substituierten 3-sulfamoylbenzoesaeuren. |
EP0008367B1 (de) * | 1978-07-20 | 1983-08-10 | BASF Aktiengesellschaft | N-Arylsulfonylpyrrole, ihre Herstellung und diese enthaltende therapeutische Mittel |
EP0010799B1 (en) * | 1978-10-27 | 1982-05-19 | Shell Internationale Researchmaatschappij B.V. | A process for the preparation of 3-azabicyclo(3.1.0)hexane derivatives and modifications thereof |
DE2917997A1 (de) * | 1979-05-04 | 1980-11-20 | Hoechst Ag | Substituierte pyrrolidinyl-benzoesaeure- derivate und verfahren zu ihrer herstellung |
DE3208189A1 (de) * | 1982-03-06 | 1983-09-08 | Hoechst Ag, 6230 Frankfurt | 2-aminomethyl-6-sulfamoylphenolderivate, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
WO1996026197A1 (en) * | 1995-02-22 | 1996-08-29 | Hoechst Pharmaceuticals & Chemicals K.K. | Amorphous piretanide, piretanide polymorphs, process for their preparation and their use |
US5908858A (en) | 1996-04-05 | 1999-06-01 | Sankyo Company, Limited | 1,2-diphenylpyrrole derivatives, their preparation and their therapeutic uses |
US8722668B2 (en) * | 1998-12-23 | 2014-05-13 | Daryl W. Hochman | Methods and compositions for the treatment of neuropathic pain and neuropsychiatric disorders |
US8008283B2 (en) * | 1998-12-23 | 2011-08-30 | Neurotherapeutics Pharma, Inc. | Methods and compositions for the treatment of neuropsychiatric disorders |
DE60336485D1 (de) | 2002-08-19 | 2011-05-05 | Pfizer | Kombinationstherapie gegen hyperproliferative erkrankungen |
NZ552501A (en) * | 2004-08-11 | 2010-03-26 | Kyorin Seiyaku Kk | Novel cyclic aminobenzoic acid derivative |
JP2008520578A (ja) * | 2004-11-15 | 2008-06-19 | ニトロメッド インコーポレーティッド | 複素環式の酸化窒素供与体基を含む利尿化合物、組成物および使用方法 |
DE102005002130A1 (de) * | 2005-01-17 | 2006-07-27 | Sanofi-Aventis Deutschland Gmbh | Substituierte N-Aminomethylensulfonamide, ihre Herstellung und Verwendung als Arzneimittel |
EP1951702A2 (en) * | 2005-10-17 | 2008-08-06 | NeuroTherapeutics Pharma, Inc. | Diuretic-like compound analogs useful for regulation of central nervous system disorders |
US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
JP2010533205A (ja) | 2007-07-12 | 2010-10-21 | トラガラ ファーマシューティカルズ,インク. | 癌、腫瘍、および腫瘍関連障害を治療するための方法および組成物 |
WO2014014519A1 (en) | 2012-07-20 | 2014-01-23 | University Of Rochester | Method of treating and preventing brain impairment using na+-k+ -2ci- cotransporter isoform 1 inhibitors |
AU2014255381A1 (en) | 2013-04-17 | 2015-10-08 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
CN111132673A (zh) | 2017-05-03 | 2020-05-08 | 维瓦斯治疗公司 | 非稠合三环化合物 |
EP3691623B1 (en) | 2017-08-21 | 2022-10-05 | Vivace Therapeutics, Inc. | Benzosulfonyl compounds |
US11524943B1 (en) | 2017-12-06 | 2022-12-13 | Vivace Therapeutics, Inc. | Benzocarbonyl compounds |
JP7611812B2 (ja) | 2018-04-06 | 2025-01-10 | ツィレンティン アーゲー | 多汗症を治療するためのブメタニド誘導体 |
US20210163406A1 (en) | 2018-04-06 | 2021-06-03 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Bumetanide Derivatives for the Therapy of Stroke and Other Neurological Diseases/Disorders Involving NKCCs |
US11661403B2 (en) | 2018-05-16 | 2023-05-30 | Vivace Therapeutics, Inc. | Oxadiazole compounds |
CN113574055B (zh) | 2019-01-18 | 2024-07-23 | 阿斯利康(瑞典)有限公司 | Pcsk9抑制剂及其使用方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1122541B (de) * | 1959-12-28 | 1962-01-25 | Hoechst Ag | Verfahren zur Herstellung von Sulfamyl-anthranilsaeuren |
US3565920A (en) * | 1966-12-29 | 1971-02-23 | Ciba Geigy Corp | 5-sulfamyl-anthranilic acids |
IE33874B1 (en) * | 1968-12-24 | 1974-11-27 | Leo Pharm Prod Ltd | New sulphamyl-benzoic acid derivatives |
US3939267A (en) * | 1972-10-13 | 1976-02-17 | Ciba-Geigy Corporation | 4-Ethers of 3-amino-5-sulfamoylbenzoic acids |
-
1974
- 1974-04-25 DE DE2419970A patent/DE2419970C3/de not_active Expired
- 1974-12-27 DE DE2461601A patent/DE2461601C2/de not_active Expired
-
1975
- 1975-04-18 NL NLAANVRAGE7504653,A patent/NL188410C/xx not_active IP Right Cessation
- 1975-04-22 CH CH510175A patent/CH615910A5/de not_active IP Right Cessation
- 1975-04-23 LU LU72348A patent/LU72348A1/xx unknown
- 1975-04-23 US US05/570,649 patent/US4010273A/en not_active Expired - Lifetime
- 1975-04-24 CA CA225,818A patent/CA1039734A/en not_active Expired
- 1975-04-24 AT AT316475A patent/AT356091B/de not_active IP Right Cessation
- 1975-04-25 JP JP50050627A patent/JPS624385B2/ja not_active Expired
- 1975-04-25 BE BE155823A patent/BE828441A/xx not_active IP Right Cessation
- 1975-04-25 GB GB17337/75A patent/GB1504505A/en not_active Expired
- 1975-04-25 FR FR7513047A patent/FR2324298A1/fr active Granted
- 1975-04-25 OA OA55483A patent/OA04987A/xx unknown
-
1978
- 1978-02-27 SE SE7802175A patent/SE425486B/sv not_active IP Right Cessation
- 1978-02-27 SE SE7802176A patent/SE425488B/sv not_active IP Right Cessation
-
1979
- 1979-02-23 CH CH181479A patent/CH616923A5/de not_active IP Right Cessation
- 1979-02-23 CH CH181279A patent/CH616921A5/de not_active IP Right Cessation
- 1979-02-23 CH CH181379A patent/CH616922A5/de not_active IP Right Cessation
- 1979-04-19 AU AU46290/79A patent/AU521892B2/en not_active Expired
- 1979-11-29 CH CH1064079A patent/CH620677A5/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE2419970C3 (de) | 1980-06-12 |
CH616922A5 (en, 2012) | 1980-04-30 |
NL7504653A (nl) | 1975-10-28 |
DE2461601C2 (de) | 1982-07-01 |
SE7802176L (sv) | 1978-02-27 |
CA1039734A (en) | 1978-10-03 |
AT356091B (de) | 1980-04-10 |
SE425486B (sv) | 1982-10-04 |
ATA316475A (de) | 1979-09-15 |
AU521892B2 (en) | 1982-05-06 |
US4010273A (en) | 1977-03-01 |
FR2324298B1 (en, 2012) | 1979-08-10 |
JPS50142558A (en, 2012) | 1975-11-17 |
BE828441A (fr) | 1975-10-27 |
CH615910A5 (en, 2012) | 1980-02-29 |
LU72348A1 (en, 2012) | 1977-02-03 |
NL188410B (nl) | 1992-01-16 |
SE425488B (sv) | 1982-10-04 |
CH620677A5 (en, 2012) | 1980-12-15 |
OA04987A (fr) | 1980-11-30 |
DE2419970B2 (en, 2012) | 1979-09-27 |
GB1504505A (en) | 1978-03-22 |
JPS624385B2 (en, 2012) | 1987-01-30 |
FR2324298A1 (fr) | 1977-04-15 |
AU4629079A (en) | 1979-11-01 |
SE7802175L (sv) | 1978-02-27 |
DE2461601A1 (de) | 1976-07-08 |
NL188410C (nl) | 1992-06-16 |
DE2419970A1 (de) | 1975-11-13 |
CH616923A5 (en, 2012) | 1980-04-30 |
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PL | Patent ceased | ||
PL | Patent ceased |