DE2917997A1 - Substituierte pyrrolidinyl-benzoesaeure- derivate und verfahren zu ihrer herstellung - Google Patents
Substituierte pyrrolidinyl-benzoesaeure- derivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2917997A1 DE2917997A1 DE19792917997 DE2917997A DE2917997A1 DE 2917997 A1 DE2917997 A1 DE 2917997A1 DE 19792917997 DE19792917997 DE 19792917997 DE 2917997 A DE2917997 A DE 2917997A DE 2917997 A1 DE2917997 A1 DE 2917997A1
- Authority
- DE
- Germany
- Prior art keywords
- benzoic acid
- acid
- formula
- compounds
- mol
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 4
- -1 Hydroxy, amino Chemical group 0.000 claims description 82
- 239000002253 acid Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 206010030113 Oedema Diseases 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 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 2
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical class NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000000054 salidiuretic effect Effects 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 35
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 31
- 239000013078 crystal Substances 0.000 description 30
- 239000005711 Benzoic acid Substances 0.000 description 25
- 229960000583 acetic acid Drugs 0.000 description 25
- 239000012362 glacial acetic acid Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 235000010233 benzoic acid Nutrition 0.000 description 15
- 239000005457 ice water Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- YBERTMQAGHYOFM-UHFFFAOYSA-N methyl 2-(dimethylaminomethylideneamino)sulfonylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)N=CN(C)C YBERTMQAGHYOFM-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 230000020477 pH reduction Effects 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- GZYGYLSHLHOMAO-UHFFFAOYSA-N 2,5-dimethoxy-2-methyloxolane Chemical compound COC1CCC(C)(OC)O1 GZYGYLSHLHOMAO-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229940093915 gynecological organic acid Drugs 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- ZZTYSYZHDBRDFC-UHFFFAOYSA-N 2-(dimethylaminomethylideneamino)sulfonylbenzoic acid Chemical compound CN(C)C=NS(=O)(=O)C1=C(C(=O)O)C=CC=C1 ZZTYSYZHDBRDFC-UHFFFAOYSA-N 0.000 description 3
- VSOOBQALJVLTBH-UHFFFAOYSA-N 2-aminosulfonyl-benzoic acid methyl ester Chemical compound COC(=O)C1=CC=CC=C1S(N)(=O)=O VSOOBQALJVLTBH-UHFFFAOYSA-N 0.000 description 3
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NAETXYOXMDYNLE-UHFFFAOYSA-N 3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC=CC(C(O)=O)=C1 NAETXYOXMDYNLE-UHFFFAOYSA-N 0.000 description 2
- DHLUJPLHLZJUBW-UHFFFAOYSA-N 6-methylpyridin-3-ol Chemical compound CC1=CC=C(O)C=N1 DHLUJPLHLZJUBW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 229940030606 diuretics Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- CXNFUAIWZFIMAK-UHFFFAOYSA-N methyl 2-(aminomethylideneamino)sulfonylbenzoate Chemical compound COC(C1=C(C=CC=C1)S(=O)(=O)N=CN)=O CXNFUAIWZFIMAK-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- URSYNYWKCHXMSX-UHFFFAOYSA-N 2,5-dimethyl-1-pyrrolidin-1-yl-5-sulfamoylcyclohex-3-ene-1-carboxylic acid Chemical compound CC1C(C(=O)O)(CC(C=C1)(S(N)(=O)=O)C)N1CCCC1 URSYNYWKCHXMSX-UHFFFAOYSA-N 0.000 description 1
- JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-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
- AWEUHBGAFMMCMR-UHFFFAOYSA-N 2-pyridin-3-yloxy-5-sulfamoylbenzoic acid Chemical compound OC(=O)C1=CC(S(=O)(=O)N)=CC=C1OC1=CC=CN=C1 AWEUHBGAFMMCMR-UHFFFAOYSA-N 0.000 description 1
- SSALRORMOVCZTK-UHFFFAOYSA-N 2-pyrrolidin-1-ylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1N1CCCC1 SSALRORMOVCZTK-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- APTODWNCSZZWDC-UHFFFAOYSA-N 3-(2,4-dimethylpyrrolidin-1-yl)-4-(4-methylphenoxy)-5-sulfamoylbenzoic acid Chemical compound C1C(C)CC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=C(C)C=C1 APTODWNCSZZWDC-UHFFFAOYSA-N 0.000 description 1
- HDBJSMYEGKHYQJ-UHFFFAOYSA-N 3-(2,5-diethylpyrrolidin-1-yl)-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound CCC1CCC(CC)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 HDBJSMYEGKHYQJ-UHFFFAOYSA-N 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
- 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 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
- PYJXYLUUDORZEP-UHFFFAOYSA-N 3-(2,5-dimethylpyrrolidin-1-yl)-5-sulfamoyl-4-thiophen-3-ylbenzoic acid Chemical compound CC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1C1=CSC=C1 PYJXYLUUDORZEP-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
- 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 1
- 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 1
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 1
- PYHSVQALGTXJOH-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yloxy)-3-(2,5-dimethylpyrrolidin-1-yl)-5-sulfamoylbenzoic acid Chemical compound CC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=C(OCO2)C2=C1 PYHSVQALGTXJOH-UHFFFAOYSA-N 0.000 description 1
- FYHDPZCTKPVHMN-UHFFFAOYSA-N 4-(4-methylphenoxy)-3-(2-methylpyrrolidin-1-yl)-5-sulfamoylbenzoic acid Chemical compound CC1CCCN1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=C(C)C=C1 FYHDPZCTKPVHMN-UHFFFAOYSA-N 0.000 description 1
- YHEYTBRHEWACOH-UHFFFAOYSA-N 4-(4-methylphenoxy)-3-sulfamoyl-5-(2,3,5-trimethylpyrrolidin-1-yl)benzoic acid Chemical compound CC1C(C)CC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=C(C)C=C1 YHEYTBRHEWACOH-UHFFFAOYSA-N 0.000 description 1
- JAHVOIGVRNMSFP-UHFFFAOYSA-N 4-(6-methylpyridin-3-yl)oxy-3-(2-methylpyrrolidin-1-yl)-5-sulfamoylbenzoic acid Chemical compound CC1CCCN1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=C(C)N=C1 JAHVOIGVRNMSFP-UHFFFAOYSA-N 0.000 description 1
- QTMXPVLWWYEZJJ-UHFFFAOYSA-N 4-[3-(dimethylamino)phenoxy]-3-(2,5-dimethylpyrrolidin-1-yl)-5-sulfamoylbenzoic acid Chemical compound CC1CCC(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC(N(C)C)=C1 QTMXPVLWWYEZJJ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- AJHJEGMQAMEHEO-UHFFFAOYSA-N 4-phenoxy-3-sulfamoyl-5-(2,3,4,5-tetramethylpyrrolidin-1-yl)benzoic acid Chemical compound CC1C(C)C(C)C(C)N1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 AJHJEGMQAMEHEO-UHFFFAOYSA-N 0.000 description 1
- LQODLHFZFWMNSY-UHFFFAOYSA-N 4-phenoxy-3-sulfamoyl-5-(2,3,4-trimethylpyrrolidin-1-yl)benzoic acid Chemical compound CC1C(C)C(C)CN1C1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 LQODLHFZFWMNSY-UHFFFAOYSA-N 0.000 description 1
- NKMWZGGOQAABOR-UHFFFAOYSA-N CNC=NS(=O)(=O)C1=C(C(=O)O)C=CC=C1 Chemical compound CNC=NS(=O)(=O)C1=C(C(=O)O)C=CC=C1 NKMWZGGOQAABOR-UHFFFAOYSA-N 0.000 description 1
- HGRGPAAXHOTBAM-UHFFFAOYSA-N Heptan-2,5-dione Chemical compound CCC(=O)CCC(C)=O HGRGPAAXHOTBAM-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- UAYWVJHJZHQCIE-UHFFFAOYSA-L Zinc iodide Inorganic materials I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229960001523 chlortalidone Drugs 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation 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
- ZFOGVSMEHYKOJO-UHFFFAOYSA-N methyl 3-amino-5-(dimethylaminomethylideneamino)sulfonyl-4-(4-methylphenyl)benzoate Chemical compound CN(C)C=NS(=O)(=O)C1=CC(C(=O)OC)=CC(N)=C1C1=CC=C(C)C=C1 ZFOGVSMEHYKOJO-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000005406 washing 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)
Priority Applications (20)
| 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 |
| ES490959A ES8101045A1 (es) | 1979-05-04 | 1980-04-28 | Procedimiento para la preparacion de derivados de acidos pi-rrolidinilsulfamoilbenzoicos sustituidos |
| FI801398A FI73413C (fi) | 1979-05-04 | 1980-04-30 | Foerfarande foer framstaellning av terapeutiskt anvaendbara substituerade pyrrolidinylsulfamoylbensoesyraderivat. |
| DE8080102320T DE3063950D1 (en) | 1979-05-04 | 1980-04-30 | Substituted 3-(1-pyrrolidinyl)-5-sulfamoyl-benzoic acid derivatives, a process for their preparation, pharmaceutical preparations containing them and a process for the preparation thereof |
| AT80102320T ATE3976T1 (de) | 1979-05-04 | 1980-04-30 | Substituierte 3-(1-pyrrolidinyl)-5-sulfamoylbenzoes[ure-derivate, verfahren zu ihrer herstellung, pharmazeutische zubereitungen, die sie enthalten und verfahren zu deren herstellung. |
| HU80801073A HU181114B (en) | 1979-05-04 | 1980-04-30 | Process for producing substituted pyrrolidinyl-benzoic acid derivatives |
| EP80102320A EP0020941B1 (de) | 1979-05-04 | 1980-04-30 | Substituierte 3-(1-Pyrrolidinyl)-5-sulfamoyl-benzoesäure-Derivate, Verfahren zu ihrer Herstellung, pharmazeutische Zubereitungen, die sie enthalten und Verfahren zu deren Herstellung |
| DK193980A DK156300C (da) | 1979-05-04 | 1980-05-01 | Analogifremgangsmaade til fremstilling af substituerede pyrrolidinyl-benzoesyrederivater |
| NO801294A NO154794C (no) | 1979-05-04 | 1980-05-02 | Analogifremgangsmaate til fremstilling av terapeutisk aktive pyrrolidinylsulfamoylbenzosyrederivater. |
| GR61843A GR67661B (enExample) | 1979-05-04 | 1980-05-02 | |
| IL59980A IL59980A (en) | 1979-05-04 | 1980-05-02 | Pyrrolidino benzoic acid derivatives,their preparation and pharmaceutical compositions comprising them |
| AR280883A AR228739A1 (es) | 1979-05-04 | 1980-05-02 | Procedimiento para preparar acidos pirrolidinilsulfamoilbenzoicos |
| AU58034/80A AU533620B2 (en) | 1979-05-04 | 1980-05-02 | Pyrrolidinyl-sulfamoylbenzoic acid derivatives |
| IE900/80A IE49779B1 (en) | 1979-05-04 | 1980-05-02 | Substituted pyrrolidinyl-benzoic acid derivatives and a process for their manufacture |
| NZ193601A NZ193601A (en) | 1979-05-04 | 1980-05-02 | Substituted pyrrolidinylsulphamoylbenzoic acid derivatives;salidiuretic pharmaceutical compositions |
| PH23974A PH17465A (en) | 1979-05-04 | 1980-05-02 | Substituted pirrolidinyl-benzoic acid derivatives and a process for their preparation and pharmaceutical formulation |
| CA000351130A CA1152996A (en) | 1979-05-04 | 1980-05-02 | Substituted pyrrolidinyl-benzoic acid derivatives and a process for their manufacture |
| JP5805080A JPS55149251A (en) | 1979-05-04 | 1980-05-02 | Substituted pyrrolidinylbenzoic acid derivative |
| ZA00802635A ZA802635B (en) | 1979-05-04 | 1980-05-02 | Substituted pyrrolidinyl-benzoic acid derivatives and a process for their manufacture |
| US06/421,030 US4492710A (en) | 1979-05-04 | 1982-09-22 | Substituted pyrrolidinyl-benzoic acid derivatives and a process for their manufacture |
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 |
|---|---|
| DE2917997A1 true DE2917997A1 (de) | 1980-11-20 |
Family
ID=6069917
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792917997 Withdrawn DE2917997A1 (de) | 1979-05-04 | 1979-05-04 | Substituierte pyrrolidinyl-benzoesaeure- derivate und verfahren zu ihrer herstellung |
| DE8080102320T Expired DE3063950D1 (en) | 1979-05-04 | 1980-04-30 | Substituted 3-(1-pyrrolidinyl)-5-sulfamoyl-benzoic acid derivatives, a process for their preparation, pharmaceutical preparations containing them and a process for the preparation thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8080102320T Expired DE3063950D1 (en) | 1979-05-04 | 1980-04-30 | Substituted 3-(1-pyrrolidinyl)-5-sulfamoyl-benzoic acid derivatives, a process for their preparation, pharmaceutical preparations containing them and a process for the preparation thereof |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4492710A (enExample) |
| EP (1) | EP0020941B1 (enExample) |
| JP (1) | JPS55149251A (enExample) |
| AR (1) | AR228739A1 (enExample) |
| AT (1) | ATE3976T1 (enExample) |
| AU (1) | AU533620B2 (enExample) |
| CA (1) | CA1152996A (enExample) |
| DE (2) | DE2917997A1 (enExample) |
| DK (1) | DK156300C (enExample) |
| ES (1) | ES8101045A1 (enExample) |
| FI (1) | FI73413C (enExample) |
| GR (1) | GR67661B (enExample) |
| HU (1) | HU181114B (enExample) |
| IE (1) | IE49779B1 (enExample) |
| IL (1) | IL59980A (enExample) |
| NO (1) | NO154794C (enExample) |
| NZ (1) | NZ193601A (enExample) |
| PH (1) | PH17465A (enExample) |
| ZA (1) | ZA802635B (enExample) |
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 |
| 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 |
| HU181114B (en) | 1983-06-28 |
| GR67661B (enExample) | 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 |
|---|---|---|---|
| 8130 | Withdrawal |