DE2021105A1 - Neue Sulfamylanthranilsaeuren - Google Patents
Neue SulfamylanthranilsaeurenInfo
- Publication number
- DE2021105A1 DE2021105A1 DE19702021105 DE2021105A DE2021105A1 DE 2021105 A1 DE2021105 A1 DE 2021105A1 DE 19702021105 DE19702021105 DE 19702021105 DE 2021105 A DE2021105 A DE 2021105A DE 2021105 A1 DE2021105 A1 DE 2021105A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- sulfamyl
- salts
- esters
- phenoxy
- 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- Withdrawn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
- 239000002253 acid Substances 0.000 title claims description 67
- 150000007513 acids Chemical class 0.000 title description 3
- -1 aliphatic radical Chemical class 0.000 claims description 102
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000002934 diuretic Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 206010030113 Oedema Diseases 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 claims description 2
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 claims description 2
- 241000489523 Veratrum Species 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims description 2
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229960002474 hydralazine Drugs 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 229960001288 triamterene Drugs 0.000 claims description 2
- 229940057613 veratrum Drugs 0.000 claims description 2
- VEXDRERIMPLZLU-UHFFFAOYSA-N 3-hydroxy-2-methylbutanoic acid Chemical compound CC(O)C(C)C(O)=O VEXDRERIMPLZLU-UHFFFAOYSA-N 0.000 claims 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- FAJWEJFNFUPOBX-UHFFFAOYSA-N 2-(butylamino)-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound C1=C(C(O)=O)C(NCCCC)=CC(OC=2C=CC=CC=2)=C1S(N)(=O)=O FAJWEJFNFUPOBX-UHFFFAOYSA-N 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 241001104043 Syringa Species 0.000 claims 1
- 235000004338 Syringa vulgaris Nutrition 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 239000003405 delayed action preparation Substances 0.000 claims 1
- 229940030606 diuretics Drugs 0.000 claims 1
- 208000021822 hypotensive Diseases 0.000 claims 1
- 230000001077 hypotensive effect Effects 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 239000003286 potassium sparing diuretic agent Substances 0.000 claims 1
- 229940097241 potassium-sparing diuretic Drugs 0.000 claims 1
- 229940080360 rauwolfia alkaloid Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 165
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 59
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- 238000001035 drying Methods 0.000 description 45
- 239000000243 solution Substances 0.000 description 42
- 238000001953 recrystallisation Methods 0.000 description 37
- 239000002244 precipitate Substances 0.000 description 33
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- 238000001914 filtration Methods 0.000 description 22
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 18
- 125000004494 ethyl ester group Chemical group 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002178 crystalline material Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- WZOIPBOIEKNNOL-UHFFFAOYSA-N 2-chloro-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)OC1=CC=CC=C1)S(N)(=O)=O WZOIPBOIEKNNOL-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZEYLIBGIGLXROY-UHFFFAOYSA-N 2-(benzylamino)-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound C1=C(OC=2C=CC=CC=2)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CC=C1 ZEYLIBGIGLXROY-UHFFFAOYSA-N 0.000 description 5
- WAEFWGYFWUXYNS-UHFFFAOYSA-N 2-amino-4-phenoxy-5-sulfamoylbenzoic acid Chemical compound O(C1=CC=CC=C1)C=1C=C(C(C(=O)O)=CC1S(N)(=O)=O)N WAEFWGYFWUXYNS-UHFFFAOYSA-N 0.000 description 5
- DDGOQDDPEWYVRD-UHFFFAOYSA-N 2-chloro-4-fluoro-5-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=C(Cl)C=C1F DDGOQDDPEWYVRD-UHFFFAOYSA-N 0.000 description 5
- SHIZRTZNEZUXFJ-UHFFFAOYSA-N 2-chloro-4-phenylsulfanyl-5-sulfamoylbenzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)SC1=CC=CC=C1)S(N)(=O)=O SHIZRTZNEZUXFJ-UHFFFAOYSA-N 0.000 description 5
- 241000251730 Chondrichthyes Species 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BIWABNSEOIQEOF-UHFFFAOYSA-N 2,4-difluoro-5-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=C(F)C=C1F BIWABNSEOIQEOF-UHFFFAOYSA-N 0.000 description 2
- UORPHGYORXCNKS-UHFFFAOYSA-N 2-(benzylamino)-4-(2-methoxyethoxy)-5-sulfamoylbenzoic acid Chemical compound COCCOC=1C=C(C(C(=O)O)=CC1S(N)(=O)=O)NCC1=CC=CC=C1 UORPHGYORXCNKS-UHFFFAOYSA-N 0.000 description 2
- GWLWXJBOTQVQGF-UHFFFAOYSA-N 2-(benzylamino)-4-phenoxy-5-(phenylsulfamoyl)benzoic acid Chemical compound O(C1=CC=CC=C1)C=1C=C(C(C(=O)O)=CC1S(NC1=CC=CC=C1)(=O)=O)NCC1=CC=CC=C1 GWLWXJBOTQVQGF-UHFFFAOYSA-N 0.000 description 2
- PJDIPBCGHBMOHK-UHFFFAOYSA-N 2-amino-4-fluoro-5-sulfamoylbenzoic acid Chemical compound NC1=CC(F)=C(S(N)(=O)=O)C=C1C(O)=O PJDIPBCGHBMOHK-UHFFFAOYSA-N 0.000 description 2
- LADZDQRGPXWMMA-UHFFFAOYSA-N 2-chloro-4-phenoxy-5-(phenylsulfamoyl)benzoic acid Chemical compound ClC1=C(C(=O)O)C=C(C(=C1)OC1=CC=CC=C1)S(NC1=CC=CC=C1)(=O)=O LADZDQRGPXWMMA-UHFFFAOYSA-N 0.000 description 2
- QOPIIRYHSQOQRN-UHFFFAOYSA-N 2-chloro-5-chlorosulfonyl-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC(S(Cl)(=O)=O)=C(F)C=C1Cl QOPIIRYHSQOQRN-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010019280 Heart failures Diseases 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
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- RQHHBGSOHVYWTM-UHFFFAOYSA-N ethyl 2-chloro-4-fluoro-5-sulfamoylbenzoate Chemical compound CCOC(=O)C1=CC(S(N)(=O)=O)=C(F)C=C1Cl RQHHBGSOHVYWTM-UHFFFAOYSA-N 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-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
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000894 saliuretic effect Effects 0.000 description 2
- 239000012056 semi-solid material Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- 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
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21890/69A GB1260155A (en) | 1969-04-29 | 1969-04-29 | Sulphonamido anthranilic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2021105A1 true DE2021105A1 (de) | 1970-11-05 |
Family
ID=10170523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702021105 Withdrawn DE2021105A1 (de) | 1969-04-29 | 1970-04-29 | Neue Sulfamylanthranilsaeuren |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3755383A (https=) |
| JP (1) | JPS543862B1 (https=) |
| AT (1) | AT299909B (https=) |
| BE (1) | BE749528A (https=) |
| BG (1) | BG17538A3 (https=) |
| DE (1) | DE2021105A1 (https=) |
| DK (1) | DK138599B (https=) |
| ES (1) | ES378948A1 (https=) |
| FR (1) | FR2042387B1 (https=) |
| GB (1) | GB1260155A (https=) |
| HU (1) | HU162439B (https=) |
| IE (1) | IE34283B1 (https=) |
| IL (1) | IL34279A0 (https=) |
| LU (1) | LU60808A1 (https=) |
| NL (1) | NL166398C (https=) |
| RO (1) | RO58846A (https=) |
| SE (1) | SE373840B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005082350A1 (en) * | 2004-02-20 | 2005-09-09 | Aventis Pharmaceuticals Inc. | Furosemide derivatives as modulators of hm74 and their use for the treatment of inflammation |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3875150A (en) * | 1969-04-29 | 1975-04-01 | Leo Pharm Prod Ltd | New sulfamyl-anthranilic acids |
| US3972886A (en) * | 1972-07-13 | 1976-08-03 | Leo Pharmaceutical Products Ltd. | Certain 4-phenoxy-3-heteroarylmethyl or ethyl sulfamyl benzoic acid derivatives |
| JPS58192820A (ja) * | 1982-05-06 | 1983-11-10 | Mochida Pharmaceut Co Ltd | 抗ウイルス作用を有する医薬組成物 |
| DE3101960A1 (de) * | 1981-01-22 | 1982-09-02 | Hoechst Ag, 6000 Frankfurt | "basisch substituierte anthranilsaeuren, verfahren zu ihrer herstellung und ihre verwendung" |
| DE10060809A1 (de) * | 2000-12-07 | 2002-06-20 | Aventis Pharma Gmbh | Substituierte Anthranilsäuren, ihre Verwendung als Medikament oder Diagnostikum, sowie sie enthaltendes Medikament, sowie ein pharmazeutisches Kombinationspräparat mit einem Natrium/Wasserstoff-Austausch (NHE)-Blocker |
| JP2006506383A (ja) * | 2002-10-21 | 2006-02-23 | カイロン コーポレイション | グリコーゲンシンターゼキナーゼ３のインヒビター |
| EP2598478A2 (en) * | 2010-07-26 | 2013-06-05 | Neurotherapeutics Pharma, Inc. | Arylsulfonamide derivatives, compositions, and methods of use |
| US20240000946A1 (en) * | 2020-12-03 | 2024-01-04 | Vilnius University | Carbonic anhydrase inhibitors synthesized on interconnecting linker chains |
| CN113219084A (zh) * | 2021-03-26 | 2021-08-06 | 天圣制药集团股份有限公司 | 一种呋塞米及其制剂中2-呋喃甲胺及其缩合反应杂质的hplc检测方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1261176A (fr) * | 1959-01-09 | 1961-05-19 | Merck & Co Inc | Procédé de fabrication de dérivés de l'aniline tels que la 2-carboxy-5-chloro-4-sulfamylacétanilide |
-
1969
- 1969-04-29 GB GB21890/69A patent/GB1260155A/en not_active Expired
-
1970
- 1970-04-07 IE IE430/70A patent/IE34283B1/xx unknown
- 1970-04-08 IL IL34279A patent/IL34279A0/xx unknown
- 1970-04-14 AT AT339370A patent/AT299909B/de not_active IP Right Cessation
- 1970-04-22 ES ES378948A patent/ES378948A1/es not_active Expired
- 1970-04-23 US US00031413A patent/US3755383A/en not_active Expired - Lifetime
- 1970-04-23 DK DK206670AA patent/DK138599B/da not_active IP Right Cessation
- 1970-04-24 BE BE749528D patent/BE749528A/xx unknown
- 1970-04-27 LU LU60808D patent/LU60808A1/xx unknown
- 1970-04-28 SE SE7005869A patent/SE373840B/xx unknown
- 1970-04-28 HU HULO362A patent/HU162439B/hu unknown
- 1970-04-28 FR FR7015530A patent/FR2042387B1/fr not_active Expired
- 1970-04-29 DE DE19702021105 patent/DE2021105A1/de not_active Withdrawn
- 1970-04-29 RO RO63231A patent/RO58846A/ro unknown
- 1970-04-29 NL NL7006334.A patent/NL166398C/xx not_active IP Right Cessation
- 1970-04-29 BG BG014598A patent/BG17538A3/xx unknown
- 1970-04-30 JP JP3639670A patent/JPS543862B1/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005082350A1 (en) * | 2004-02-20 | 2005-09-09 | Aventis Pharmaceuticals Inc. | Furosemide derivatives as modulators of hm74 and their use for the treatment of inflammation |
| AU2005216879B2 (en) * | 2004-02-20 | 2009-12-10 | Aventis Pharmaceuticals Inc | Furosemide derivatives as modulators of HM74 and their use for the treatment of inflammation |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2042387B1 (https=) | 1974-05-24 |
| BE749528A (fr) | 1970-10-01 |
| HU162439B (https=) | 1973-02-28 |
| BG17538A3 (bg) | 1973-11-10 |
| DK138599C (https=) | 1979-02-19 |
| SE373840B (https=) | 1975-02-17 |
| IE34283L (en) | 1970-10-29 |
| LU60808A1 (https=) | 1970-06-29 |
| NL166398B (nl) | 1981-03-16 |
| DK138599B (da) | 1978-10-02 |
| US3755383A (en) | 1973-08-28 |
| IE34283B1 (en) | 1975-04-02 |
| AT299909B (de) | 1972-07-10 |
| NL7006334A (https=) | 1970-11-02 |
| FR2042387A1 (https=) | 1971-02-12 |
| JPS543862B1 (https=) | 1979-02-27 |
| ES378948A1 (es) | 1973-01-16 |
| NL166398C (nl) | 1981-08-17 |
| IL34279A0 (en) | 1970-06-17 |
| RO58846A (https=) | 1975-10-15 |
| GB1260155A (en) | 1972-01-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |