HU181114B - Process for producing substituted pyrrolidinyl-benzoic acid derivatives - Google Patents
Process for producing substituted pyrrolidinyl-benzoic acid derivatives Download PDFInfo
- Publication number
- HU181114B HU181114B HU80801073A HU107380A HU181114B HU 181114 B HU181114 B HU 181114B HU 80801073 A HU80801073 A HU 80801073A HU 107380 A HU107380 A HU 107380A HU 181114 B HU181114 B HU 181114B
- Authority
- HU
- Hungary
- Prior art keywords
- methyl
- benzoic acid
- formula
- acid
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- SSALRORMOVCZTK-UHFFFAOYSA-N 2-pyrrolidin-1-ylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1N1CCCC1 SSALRORMOVCZTK-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 84
- -1 3,4-methylenedioxy group Chemical group 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000009903 catalytic hydrogenation reaction Methods 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 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- NIESLGOMXRSOCK-UHFFFAOYSA-N 2-(pyrrolidin-1-ylsulfamoyl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1S(=O)(=O)NN1CCCC1 NIESLGOMXRSOCK-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical class NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims 1
- WXSRPJAOBRLWOI-UHFFFAOYSA-N 3-pyrrolidin-1-yl-2-sulfamoylbenzoic acid Chemical class N1(CCCC1)C=1C(=C(C(=O)O)C=CC=1)S(N)(=O)=O WXSRPJAOBRLWOI-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000012059 conventional drug carrier Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- 239000000243 solution Substances 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 229960000583 acetic acid Drugs 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000012362 glacial acetic acid Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 20
- 238000001953 recrystallisation Methods 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 14
- 239000005457 ice water Substances 0.000 description 14
- 239000013078 crystal Substances 0.000 description 12
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- GZYGYLSHLHOMAO-UHFFFAOYSA-N 2,5-dimethoxy-2-methyloxolane Chemical compound COC1CCC(C)(OC)O1 GZYGYLSHLHOMAO-UHFFFAOYSA-N 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000005711 Benzoic acid Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical class NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- IRTAOLBCCZQOFT-UHFFFAOYSA-N 3-(2,5-dimethylpyrrolidin-1-yl)-4-(4-methoxyphenoxy)-5-sulfamoylbenzoic acid Chemical compound C1=CC(OC)=CC=C1OC1=C(N2C(CCC2C)C)C=C(C(O)=O)C=C1S(N)(=O)=O IRTAOLBCCZQOFT-UHFFFAOYSA-N 0.000 description 5
- KFOBXDSIKYKNAW-UHFFFAOYSA-N 3-(2,5-dimethylpyrrolidin-1-yl)-4-(4-methylphenoxy)-5-sulfamoylbenzoic acid Chemical compound CC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=C(C)C=C1 KFOBXDSIKYKNAW-UHFFFAOYSA-N 0.000 description 5
- NAETXYOXMDYNLE-UHFFFAOYSA-N 3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC=CC(C(O)=O)=C1 NAETXYOXMDYNLE-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 230000000054 salidiuretic effect Effects 0.000 description 3
- 230000000894 saliuretic effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- POCFQAWMLJURSR-UHFFFAOYSA-N 3-(2,5-dimethylpyrrolidin-1-yl)-4-(6-methylpyridin-3-yl)oxy-5-sulfamoylbenzoic acid Chemical compound CC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=C(C)N=C1 POCFQAWMLJURSR-UHFFFAOYSA-N 0.000 description 2
- UCMVKJNRSLHLFB-UHFFFAOYSA-N 3-(2,5-dimethylpyrrolidin-1-yl)-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound CC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 UCMVKJNRSLHLFB-UHFFFAOYSA-N 0.000 description 2
- XWEPPWHZBWWICP-UHFFFAOYSA-N 3-(2,5-dimethylpyrrolidin-1-yl)-5-sulfamoyl-4-thiophen-2-ylbenzoic acid Chemical compound CC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1C1=CC=CS1 XWEPPWHZBWWICP-UHFFFAOYSA-N 0.000 description 2
- YRNAVPVMADSCBK-UHFFFAOYSA-N 3-(2-ethylpyrrolidin-1-yl)-4-(4-methylphenoxy)-5-sulfamoylbenzoic acid Chemical compound CCC1CCCN1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=C(C)C=C1 YRNAVPVMADSCBK-UHFFFAOYSA-N 0.000 description 2
- YZOPHVMSGNXJAB-UHFFFAOYSA-N 3-(2-methylpyrrolidin-1-yl)-4-pyridin-3-yloxy-5-sulfamoylbenzoic acid Chemical compound CC1CCCN1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CN=C1 YZOPHVMSGNXJAB-UHFFFAOYSA-N 0.000 description 2
- XMFPXASJYCMLSU-UHFFFAOYSA-N 4-(4-methylphenoxy)-3-sulfamoylbenzoic acid Chemical compound CC1=CC=C(OC2=CC=C(C(=O)O)C=C2S(N)(=O)=O)C=C1 XMFPXASJYCMLSU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 206010030113 Oedema Diseases 0.000 description 2
- 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- 238000002425 crystallisation Methods 0.000 description 2
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- 125000005594 diketone group Chemical group 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
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- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910001414 potassium ion Inorganic materials 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
- SXPXTWDTSIXSMS-UHFFFAOYSA-N 2-ethyl-2,5-dimethoxyoxolane Chemical compound CCC1(OC)CCC(OC)O1 SXPXTWDTSIXSMS-UHFFFAOYSA-N 0.000 description 1
- RXOWEHPQOPLQFT-UHFFFAOYSA-N 2-ethyl-5-methyl-1-pyrrolidin-1-yl-5-sulfamoylcyclohex-3-ene-1-carboxylic acid Chemical compound C(C)C1C(C(=O)O)(CC(C=C1)(S(N)(=O)=O)C)N1CCCC1 RXOWEHPQOPLQFT-UHFFFAOYSA-N 0.000 description 1
- OKWHKQVROKVNQF-UHFFFAOYSA-N 2-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1OC=1C(C(O)=O)=CC(S(=O)(=O)N)=CC=1N1CCCC1 OKWHKQVROKVNQF-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- UQYKZFDBWITKAE-UHFFFAOYSA-N 3-(2,5-dimethylpyrrolidin-1-yl)-4-(4-methylanilino)-5-sulfamoylbenzoic acid Chemical compound CC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1NC1=CC=C(C)C=C1 UQYKZFDBWITKAE-UHFFFAOYSA-N 0.000 description 1
- HOSDYTRRIPHADP-UHFFFAOYSA-N 3-(2,5-dimethylpyrrolidin-1-yl)-4-pyridin-3-yloxy-5-sulfamoylbenzoic acid Chemical compound CC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CN=C1 HOSDYTRRIPHADP-UHFFFAOYSA-N 0.000 description 1
- JLAZMBGLYPIWDP-UHFFFAOYSA-N 3-(2-ethyl-5-methylpyrrolidin-1-yl)-4-(4-methylphenoxy)-5-sulfamoylbenzoic acid Chemical compound CCC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=C(C)C=C1 JLAZMBGLYPIWDP-UHFFFAOYSA-N 0.000 description 1
- IBZUOIMTBCEAFE-UHFFFAOYSA-N 3-(2-methylpyrrolidin-1-yl)-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound CC1CCCN1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 IBZUOIMTBCEAFE-UHFFFAOYSA-N 0.000 description 1
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 1
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- 239000004480 active ingredient Substances 0.000 description 1
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- 230000035619 diuresis Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- SYMKYQSQQSRVCQ-UHFFFAOYSA-N methyl 3-(dimethylaminomethylideneamino)sulfonyl-5-nitro-4-pyridin-3-yloxybenzoate Chemical compound CN(C)C=NS(=O)(=O)C1=CC(C(=O)OC)=CC([N+]([O-])=O)=C1OC1=CC=CN=C1 SYMKYQSQQSRVCQ-UHFFFAOYSA-N 0.000 description 1
- ZECAWHMBIUHKAH-UHFFFAOYSA-N methyl 3-amino-5-(dimethylaminomethylideneamino)sulfonyl-4-(6-methylpyridin-3-yl)oxybenzoate Chemical compound CN(C)C=NS(=O)(=O)C1=CC(C(=O)OC)=CC(N)=C1OC1=CC=C(C)N=C1 ZECAWHMBIUHKAH-UHFFFAOYSA-N 0.000 description 1
- GCWKIEZPRYIZGW-UHFFFAOYSA-N methyl 3-amino-5-(dimethylaminomethylideneamino)sulfonyl-4-phenoxybenzoate Chemical compound CN(C)C=NS(=O)(=O)C1=CC(C(=O)OC)=CC(N)=C1OC1=CC=CC=C1 GCWKIEZPRYIZGW-UHFFFAOYSA-N 0.000 description 1
- YONJZPRWFZKGIF-UHFFFAOYSA-N methyl 3-amino-5-(dimethylaminomethylideneamino)sulfonyl-4-thiophen-2-ylbenzoate Chemical compound CN(C)C=NS(=O)(=O)C1=CC(C(=O)OC)=CC(N)=C1C1=CC=CS1 YONJZPRWFZKGIF-UHFFFAOYSA-N 0.000 description 1
- CRIQOPHXBSYSOQ-UHFFFAOYSA-N methyl 4-chloro-3-(dimethylaminomethylideneamino)sulfonyl-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(Cl)C(S(=O)(=O)N=CN(C)C)=C1 CRIQOPHXBSYSOQ-UHFFFAOYSA-N 0.000 description 1
- MEPRRLRSOIESKI-UHFFFAOYSA-N methyl 6-sulfonylcyclohexa-2,4-diene-1-carboxylate Chemical compound COC(=O)C1C=CC=CC1=S(=O)=O MEPRRLRSOIESKI-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229940037179 potassium ion Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035753 saluresis Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc 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
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792917997 DE2917997A1 (de) | 1979-05-04 | 1979-05-04 | Substituierte pyrrolidinyl-benzoesaeure- derivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU181114B true HU181114B (en) | 1983-06-28 |
Family
ID=6069917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80801073A HU181114B (en) | 1979-05-04 | 1980-04-30 | Process for producing substituted pyrrolidinyl-benzoic acid derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4492710A (en:Method) |
| EP (1) | EP0020941B1 (en:Method) |
| JP (1) | JPS55149251A (en:Method) |
| AR (1) | AR228739A1 (en:Method) |
| AT (1) | ATE3976T1 (en:Method) |
| AU (1) | AU533620B2 (en:Method) |
| CA (1) | CA1152996A (en:Method) |
| DE (2) | DE2917997A1 (en:Method) |
| DK (1) | DK156300C (en:Method) |
| ES (1) | ES8101045A1 (en:Method) |
| FI (1) | FI73413C (en:Method) |
| GR (1) | GR67661B (en:Method) |
| HU (1) | HU181114B (en:Method) |
| IE (1) | IE49779B1 (en:Method) |
| IL (1) | IL59980A (en:Method) |
| NO (1) | NO154794C (en:Method) |
| NZ (1) | NZ193601A (en:Method) |
| PH (1) | PH17465A (en:Method) |
| ZA (1) | ZA802635B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3727114A1 (de) * | 1987-08-14 | 1989-02-23 | Basf Ag | Verfahren zur herstellung von pyrrolen |
| JP7245229B2 (ja) * | 2017-08-21 | 2023-03-23 | ビバーチェ セラピューティクス，インク． | ベンゾスルホニル化合物 |
| US11524943B1 (en) | 2017-12-06 | 2022-12-13 | Vivace Therapeutics, Inc. | Benzocarbonyl compounds |
| WO2019222431A1 (en) | 2018-05-16 | 2019-11-21 | Vivace Therapeutics, Inc. | Oxadiazole compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3824003A (en) * | 1973-05-07 | 1974-07-16 | Hughes Aircraft Co | Liquid crystal display panel |
| DE2419970C3 (de) * | 1974-04-25 | 1980-06-12 | Hoechst Ag, 6000 Frankfurt | 3-<l-Pyrrolidinyl)-4-phenoxy-5sulfamoylbenzoesäure und Verfahren zu ihrer Herstellung |
| ES465207A1 (es) * | 1976-12-24 | 1978-11-16 | Hoechst Ag | Procedimiento para la preparacion de derivados de acidos pi-rrolo-benzoicos. |
| CH628622A5 (de) * | 1976-12-24 | 1982-03-15 | Ciba Geigy Ag | Verfahren zur herstellung von neuen in 4-stellung substituierten 3-sulfamoylbenzoesaeuren. |
| DE2658766C2 (de) * | 1976-12-24 | 1986-01-02 | Hoechst Ag, 6230 Frankfurt | 3-N-Pyrrolo-5-sulfamoylbenzoesäure-Derivate und Verfahren zu ihrer Herstellung |
| DE2718494A1 (de) * | 1977-04-26 | 1978-11-09 | Hoechst Ag | Verfahren zur herstellung von pyrrolo-benzoesaeure-derivaten |
-
1979
- 1979-05-04 DE DE19792917997 patent/DE2917997A1/de not_active Withdrawn
-
1980
- 1980-04-28 ES ES490959A patent/ES8101045A1/es not_active Expired
- 1980-04-30 EP EP80102320A patent/EP0020941B1/de not_active Expired
- 1980-04-30 DE DE8080102320T patent/DE3063950D1/de not_active Expired
- 1980-04-30 AT AT80102320T patent/ATE3976T1/de active
- 1980-04-30 FI FI801398A patent/FI73413C/fi not_active IP Right Cessation
- 1980-04-30 HU HU80801073A patent/HU181114B/hu unknown
- 1980-05-01 DK DK193980A patent/DK156300C/da not_active IP Right Cessation
- 1980-05-02 JP JP5805080A patent/JPS55149251A/ja active Pending
- 1980-05-02 NZ NZ193601A patent/NZ193601A/en unknown
- 1980-05-02 GR GR61843A patent/GR67661B/el unknown
- 1980-05-02 ZA ZA00802635A patent/ZA802635B/xx unknown
- 1980-05-02 CA CA000351130A patent/CA1152996A/en not_active Expired
- 1980-05-02 AR AR280883A patent/AR228739A1/es active
- 1980-05-02 AU AU58034/80A patent/AU533620B2/en not_active Expired
- 1980-05-02 NO NO801294A patent/NO154794C/no unknown
- 1980-05-02 IL IL59980A patent/IL59980A/xx unknown
- 1980-05-02 IE IE900/80A patent/IE49779B1/en not_active IP Right Cessation
- 1980-05-02 PH PH23974A patent/PH17465A/en unknown
-
1982
- 1982-09-22 US US06/421,030 patent/US4492710A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FI73413B (fi) | 1987-06-30 |
| DE2917997A1 (de) | 1980-11-20 |
| FI801398A7 (fi) | 1980-11-05 |
| AU5803480A (en) | 1980-11-06 |
| FI73413C (fi) | 1987-10-09 |
| JPS55149251A (en) | 1980-11-20 |
| IL59980A0 (en) | 1980-07-31 |
| EP0020941A1 (de) | 1981-01-07 |
| DK156300B (da) | 1989-07-31 |
| EP0020941B1 (de) | 1983-06-29 |
| NZ193601A (en) | 1984-04-27 |
| PH17465A (en) | 1984-08-29 |
| NO801294L (no) | 1980-11-05 |
| NO154794B (no) | 1986-09-15 |
| ATE3976T1 (de) | 1983-07-15 |
| AU533620B2 (en) | 1983-12-01 |
| US4492710A (en) | 1985-01-08 |
| NO154794C (no) | 1986-12-29 |
| DE3063950D1 (en) | 1983-08-04 |
| ES490959A0 (es) | 1980-12-01 |
| GR67661B (en:Method) | 1981-09-02 |
| DK156300C (da) | 1989-12-18 |
| ZA802635B (en) | 1981-05-27 |
| ES8101045A1 (es) | 1980-12-01 |
| IL59980A (en) | 1983-10-31 |
| DK193980A (da) | 1980-11-05 |
| CA1152996A (en) | 1983-08-30 |
| IE800900L (en) | 1980-11-04 |
| AR228739A1 (es) | 1983-04-15 |
| IE49779B1 (en) | 1985-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |