DE2130313A1 - Neue Sulfamylbenzoesaeuren - Google Patents
Neue SulfamylbenzoesaeurenInfo
- Publication number
- DE2130313A1 DE2130313A1 DE19712130313 DE2130313A DE2130313A1 DE 2130313 A1 DE2130313 A1 DE 2130313A1 DE 19712130313 DE19712130313 DE 19712130313 DE 2130313 A DE2130313 A DE 2130313A DE 2130313 A1 DE2130313 A1 DE 2130313A1
- Authority
- DE
- Germany
- Prior art keywords
- esters
- acid
- pharmaceutically acceptable
- acceptable salts
- benzyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims description 65
- 150000007513 acids Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 62
- -1 4-Benzyl-2-n-pentylamino Chemical group 0.000 claims description 58
- 150000002148 esters Chemical class 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 46
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- XIJMVBVJMIFZMG-UHFFFAOYSA-N 2-amino-4-benzyl-5-sulfamoylbenzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC(CC=2C=CC=CC=2)=C1S(N)(=O)=O XIJMVBVJMIFZMG-UHFFFAOYSA-N 0.000 claims description 6
- XDNHTCYIKNVQFR-UHFFFAOYSA-N 3-amino-4-benzyl-5-sulfamoylbenzoic acid Chemical compound NC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1CC1=CC=CC=C1 XDNHTCYIKNVQFR-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- VCPBYLUDWGYFIQ-UHFFFAOYSA-N 4-benzyl-3-(butylamino)-5-sulfamoylbenzoic acid Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1CC1=CC=CC=C1 VCPBYLUDWGYFIQ-UHFFFAOYSA-N 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- BRLCHEHYRZYNFN-UHFFFAOYSA-N 4-benzyl-2-(benzylamino)-5-sulfamoylbenzoic acid Chemical compound C(C1=CC=CC=C1)C1=CC(=C(C(=O)O)C=C1S(N)(=O)=O)NCC1=CC=CC=C1 BRLCHEHYRZYNFN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- QETFFKSYPSDMFB-UHFFFAOYSA-N 4-benzyl-3-(benzylamino)-5-sulfamoylbenzoic acid Chemical compound C=1C=CC=CC=1CC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1NCC1=CC=CC=C1 QETFFKSYPSDMFB-UHFFFAOYSA-N 0.000 claims description 3
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 3
- DJRAVHMIQHVJNA-UHFFFAOYSA-N 4-benzyl-3-(pentylamino)-5-sulfamoylbenzoic acid Chemical compound C(C1=CC=CC=C1)C1=C(C=C(C(=O)O)C=C1S(N)(=O)=O)NCCCCC DJRAVHMIQHVJNA-UHFFFAOYSA-N 0.000 claims description 2
- HJVKGTAPQMDDQQ-UHFFFAOYSA-N 4-benzyl-3-(propylamino)-5-sulfamoylbenzoic acid Chemical compound C(C1=CC=CC=C1)C1=C(C=C(C(=O)O)C=C1S(N)(=O)=O)NCCC HJVKGTAPQMDDQQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- PZPDKQHALFLZOC-UHFFFAOYSA-N 4-benzyl-2-(3-methylbutylamino)-5-sulfamoylbenzoic acid Chemical compound C(C1=CC=CC=C1)C1=CC(=C(C(=O)O)C=C1S(N)(=O)=O)NCCC(C)C PZPDKQHALFLZOC-UHFFFAOYSA-N 0.000 claims 1
- SRDQDDBXYMKKOO-UHFFFAOYSA-N 4-benzyl-2-(butylamino)-5-sulfamoylbenzoic acid Chemical compound C(C1=CC=CC=C1)C1=CC(=C(C(=O)O)C=C1S(N)(=O)=O)NCCCC SRDQDDBXYMKKOO-UHFFFAOYSA-N 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 135
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- 238000001914 filtration Methods 0.000 description 32
- 238000001035 drying Methods 0.000 description 30
- 238000001953 recrystallisation Methods 0.000 description 27
- 239000002244 precipitate Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000001816 cooling Methods 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 238000003756 stirring Methods 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- WFWWEYIITVTCFL-UHFFFAOYSA-N 4-benzoyl-3,5-dinitrobenzoic acid Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=C(C(=O)O)C=C1[N+](=O)[O-])[N+](=O)[O-] WFWWEYIITVTCFL-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- FGHJJNBWLUIOMI-UHFFFAOYSA-N ethyl 4-benzoyl-3,5-dinitrobenzoate Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=C(C(=O)OCC)C=C1[N+](=O)[O-])[N+](=O)[O-] FGHJJNBWLUIOMI-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- YKQXJSFODOCRGV-UHFFFAOYSA-N 3-amino-4-benzoyl-5-nitrobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1C(=O)C1=CC=CC=C1 YKQXJSFODOCRGV-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- CEIOMRZKEHGPJQ-UHFFFAOYSA-N 4-benzoyl-5-chloro-2-nitrobenzoic acid Chemical class C(C1=CC=CC=C1)(=O)C1=CC(=C(C(=O)O)C=C1Cl)[N+](=O)[O-] CEIOMRZKEHGPJQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- WKBBZFMQPBZOHW-UHFFFAOYSA-N N-(4-benzoyl-5-chloro-2-nitrophenyl)acetamide Chemical compound N(C(=O)C)C1=CC(=C(C(=O)C2=CC=CC=C2)C=C1[N+](=O)[O-])Cl WKBBZFMQPBZOHW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- KDQZGAUVCAKSOF-UHFFFAOYSA-N (4-amino-2-chloro-5-nitrophenyl)-phenylmethanone Chemical compound NC1=CC(=C(C(=O)C2=CC=CC=C2)C=C1[N+](=O)[O-])Cl KDQZGAUVCAKSOF-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 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
- HUNCYHBHFMHLCR-UHFFFAOYSA-N 4-(4-chlorobenzoyl)-3,5-dinitrobenzoic acid Chemical compound ClC1=CC=C(C(=O)C2=C(C=C(C(=O)O)C=C2[N+](=O)[O-])[N+](=O)[O-])C=C1 HUNCYHBHFMHLCR-UHFFFAOYSA-N 0.000 description 2
- SGILKVUOQHYDHT-UHFFFAOYSA-N 4-acetamido-2-chloro-5-nitrobenzoic acid Chemical compound CC(=O)NC1=CC(Cl)=C(C(O)=O)C=C1[N+]([O-])=O SGILKVUOQHYDHT-UHFFFAOYSA-N 0.000 description 2
- ZRLWMTGZWHJPSH-UHFFFAOYSA-N 4-benzoyl-3-nitro-5-sulfamoylbenzoic acid Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=C(C(=O)O)C=C1S(N)(=O)=O)[N+](=O)[O-] ZRLWMTGZWHJPSH-UHFFFAOYSA-N 0.000 description 2
- MWVOTWTWISZRQF-UHFFFAOYSA-N 4-benzoyl-5-chloro-2-nitrobenzonitrile Chemical compound ClC1=C(C(=O)C2=CC=CC=C2)C=C(C(=C1)C#N)[N+](=O)[O-] MWVOTWTWISZRQF-UHFFFAOYSA-N 0.000 description 2
- LVBUJNCDSYAPTH-UHFFFAOYSA-N 4-benzyl-3-butyl-5-sulfamoylbenzoic acid Chemical compound C(C1=CC=CC=C1)C1=C(C=C(C(=O)O)C=C1S(N)(=O)=O)CCCC LVBUJNCDSYAPTH-UHFFFAOYSA-N 0.000 description 2
- JIHQBENXEXHFLV-UHFFFAOYSA-N 4-ethoxycarbonyl-2,6-dinitrobenzoic acid Chemical compound [N+](=O)([O-])C1=C(C(=O)O)C(=CC(=C1)C(=O)OCC)[N+](=O)[O-] JIHQBENXEXHFLV-UHFFFAOYSA-N 0.000 description 2
- BDGUMNKYAUAVEV-UHFFFAOYSA-N 5-amino-1,1-dioxo-3-phenyl-1,2-benzothiazole-6-carboxylic acid Chemical compound NC=1C(=CC2=C(C(=NS2(=O)=O)C2=CC=CC=C2)C1)C(=O)O BDGUMNKYAUAVEV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 206010037423 Pulmonary oedema Diseases 0.000 description 2
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- DFXHFSMWJBYOOE-UHFFFAOYSA-N cyanomethyl 4-benzyl-3-butyl-5-sulfamoylbenzoate Chemical compound C(C1=CC=CC=C1)C1=C(C=C(C(=O)OCC#N)C=C1S(N)(=O)=O)CCCC DFXHFSMWJBYOOE-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000000894 saliuretic effect Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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- SMSAPZICLFYVJS-QEGASFHISA-N rescinnamine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1 SMSAPZICLFYVJS-QEGASFHISA-N 0.000 description 1
- 229960001965 rescinnamine Drugs 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960002256 spironolactone Drugs 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
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229940057613 veratrum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/61—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2974270 | 1970-06-18 | ||
| US28876572A | 1972-09-15 | 1972-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2130313A1 true DE2130313A1 (de) | 1971-12-30 |
Family
ID=26260060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712130313 Pending DE2130313A1 (de) | 1970-06-18 | 1971-06-18 | Neue Sulfamylbenzoesaeuren |
Country Status (10)
| Country | Link |
|---|---|
| AT (3) | AT317869B (enrdf_load_stackoverflow) |
| BG (2) | BG20576A3 (enrdf_load_stackoverflow) |
| CA (1) | CA979440A (enrdf_load_stackoverflow) |
| DE (1) | DE2130313A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2100779B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1327481A (enrdf_load_stackoverflow) |
| LU (1) | LU63352A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7108420A (enrdf_load_stackoverflow) |
| SE (3) | SE392267B (enrdf_load_stackoverflow) |
| ZA (1) | ZA713698B (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE76C (de) * | 1877-07-07 | G. CRESPEL in Frankfurt a. M | Trockenapparat |
-
1970
- 1970-06-18 GB GB2974270A patent/GB1327481A/en not_active Expired
-
1971
- 1971-06-08 ZA ZA713698A patent/ZA713698B/xx unknown
- 1971-06-16 AT AT00572/73A patent/AT317869B/de not_active IP Right Cessation
- 1971-06-16 AT AT00573/73A patent/AT317178B/de active
- 1971-06-16 AT AT518271A patent/AT311940B/de not_active IP Right Cessation
- 1971-06-17 CA CA115,926A patent/CA979440A/en not_active Expired
- 1971-06-17 LU LU63352D patent/LU63352A1/xx unknown
- 1971-06-17 FR FR7122071A patent/FR2100779B1/fr not_active Expired
- 1971-06-17 SE SE7107903A patent/SE392267B/xx unknown
- 1971-06-18 DE DE19712130313 patent/DE2130313A1/de active Pending
- 1971-06-18 NL NL7108420A patent/NL7108420A/xx unknown
- 1971-06-18 BG BG017852A patent/BG20576A3/xx unknown
- 1971-06-18 BG BG19592A patent/BG19139A3/xx unknown
-
1974
- 1974-02-04 SE SE7401454A patent/SE405358B/xx unknown
- 1974-02-04 SE SE7401453A patent/SE404921B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG20576A3 (bg) | 1975-12-05 |
| FR2100779A1 (enrdf_load_stackoverflow) | 1972-03-24 |
| GB1327481A (en) | 1973-08-22 |
| CA979440A (en) | 1975-12-09 |
| SE392267B (sv) | 1977-03-21 |
| ZA713698B (en) | 1972-01-26 |
| AT317869B (de) | 1974-09-25 |
| AT317178B (de) | 1974-08-12 |
| AT311940B (de) | 1973-12-10 |
| NL7108420A (enrdf_load_stackoverflow) | 1971-12-21 |
| SE405358B (sv) | 1978-12-04 |
| SE404921B (sv) | 1978-11-06 |
| FR2100779B1 (enrdf_load_stackoverflow) | 1974-08-30 |
| LU63352A1 (enrdf_load_stackoverflow) | 1971-09-20 |
| BG19139A3 (enrdf_load_stackoverflow) | 1975-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |