SK542007A3 - Substituované sulfónamidy, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents
Substituované sulfónamidy, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie Download PDFInfo
- Publication number
- SK542007A3 SK542007A3 SK54-2007A SK542007A SK542007A3 SK 542007 A3 SK542007 A3 SK 542007A3 SK 542007 A SK542007 A SK 542007A SK 542007 A3 SK542007 A3 SK 542007A3
- Authority
- SK
- Slovakia
- Prior art keywords
- sulfamoyl
- benzene
- bis
- benzamide
- ethyl
- Prior art date
Links
- 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 78
- 239000003814 drug Substances 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 229940124530 sulfonamide Drugs 0.000 title claims description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 150000004677 hydrates Chemical class 0.000 claims abstract description 7
- 239000012453 solvate Substances 0.000 claims abstract description 7
- LLFQHNCOIPUFIJ-UHFFFAOYSA-N 4-sulfamoylbenzenesulfonyl chloride Chemical compound NS(=O)(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 LLFQHNCOIPUFIJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 238000007344 nucleophilic reaction Methods 0.000 claims abstract description 3
- -1 4- (N, N-diethylaminoethoxy) benzyl Chemical group 0.000 claims description 107
- UCAGLBKTLXCODC-UHFFFAOYSA-M 4-sulfamoylbenzoate Chemical compound NS(=O)(=O)C1=CC=C(C([O-])=O)C=C1 UCAGLBKTLXCODC-UHFFFAOYSA-M 0.000 claims description 39
- 238000002360 preparation method Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 18
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- SOSVTEHBZNSARP-UHFFFAOYSA-N 4-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC=C(C(Cl)=O)C=C1 SOSVTEHBZNSARP-UHFFFAOYSA-N 0.000 claims description 6
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 claims description 5
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- MWFFIRCXGDGFQB-UHFFFAOYSA-N 4-sulfamoylbenzamide Chemical compound NC(=O)C1=CC=C(S(N)(=O)=O)C=C1 MWFFIRCXGDGFQB-UHFFFAOYSA-N 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 claims description 2
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims description 2
- ZRZSNDOSAKVANP-UHFFFAOYSA-N 2-[ethyl(methyl)amino]ethyl 4-sulfamoylbenzoate Chemical compound CCN(C)CCOC(=O)C1=CC=C(S(N)(=O)=O)C=C1 ZRZSNDOSAKVANP-UHFFFAOYSA-N 0.000 claims description 2
- WCPDSPPFBHHROY-UHFFFAOYSA-N 2-[ethyl(propyl)amino]ethyl 4-sulfamoylbenzoate Chemical compound CCCN(CC)CCOC(=O)C1=CC=C(S(N)(=O)=O)C=C1 WCPDSPPFBHHROY-UHFFFAOYSA-N 0.000 claims description 2
- ASDZGCFPQRLHEY-UHFFFAOYSA-N 3-[ethyl(methyl)amino]propyl 4-sulfamoylbenzoate Chemical compound CCN(C)CCCOC(=O)C1=CC=C(S(N)(=O)=O)C=C1 ASDZGCFPQRLHEY-UHFFFAOYSA-N 0.000 claims description 2
- XYLJNLCSTIOKRM-UHFFFAOYSA-N Alphagan Chemical compound C1=CC2=NC=CN=C2C(Br)=C1NC1=NCCN1 XYLJNLCSTIOKRM-UHFFFAOYSA-N 0.000 claims description 2
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 claims description 2
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000150 Sympathomimetic Substances 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000002876 beta blocker Substances 0.000 claims description 2
- 229940097320 beta blocking agent Drugs 0.000 claims description 2
- 229960004324 betaxolol Drugs 0.000 claims description 2
- CHDPSNLJFOQTRK-UHFFFAOYSA-N betaxolol hydrochloride Chemical compound [Cl-].C1=CC(OCC(O)C[NH2+]C(C)C)=CC=C1CCOCC1CC1 CHDPSNLJFOQTRK-UHFFFAOYSA-N 0.000 claims description 2
- 229960003679 brimonidine Drugs 0.000 claims description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 2
- 229960004484 carbachol Drugs 0.000 claims description 2
- 229960002896 clonidine Drugs 0.000 claims description 2
- RFWZESUMWJKKRN-UHFFFAOYSA-N dapiprazole Chemical compound CC1=CC=CC=C1N1CCN(CCC=2N3CCCCC3=NN=2)CC1 RFWZESUMWJKKRN-UHFFFAOYSA-N 0.000 claims description 2
- 229960002947 dapiprazole Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- GGXICVAJURFBLW-CEYXHVGTSA-N latanoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 GGXICVAJURFBLW-CEYXHVGTSA-N 0.000 claims description 2
- 229960001160 latanoprost Drugs 0.000 claims description 2
- 229960000831 levobunolol Drugs 0.000 claims description 2
- IXHBTMCLRNMKHZ-LBPRGKRZSA-N levobunolol Chemical compound O=C1CCCC2=C1C=CC=C2OC[C@@H](O)CNC(C)(C)C IXHBTMCLRNMKHZ-LBPRGKRZSA-N 0.000 claims description 2
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- QRHSBFIPYGMRKI-UHFFFAOYSA-N n-(3-piperidin-1-ylpropyl)-4-sulfamoylbenzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)NCCCN1CCCCC1 QRHSBFIPYGMRKI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000734 parasympathomimetic agent Substances 0.000 claims description 2
- 230000001499 parasympathomimetic effect Effects 0.000 claims description 2
- 229940005542 parasympathomimetics Drugs 0.000 claims description 2
- 229960001416 pilocarpine Drugs 0.000 claims description 2
- 150000003180 prostaglandins Chemical class 0.000 claims description 2
- 230000001975 sympathomimetic effect Effects 0.000 claims description 2
- 229940064707 sympathomimetics Drugs 0.000 claims description 2
- 229960004605 timolol Drugs 0.000 claims description 2
- 229960002368 travoprost Drugs 0.000 claims description 2
- MKPLKVHSHYCHOC-AHTXBMBWSA-N travoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1 MKPLKVHSHYCHOC-AHTXBMBWSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 3
- ACDPSQMEFRHYJP-UHFFFAOYSA-N 3-[butyl(ethyl)amino]propyl 4-sulfamoylbenzoate Chemical compound CCCCN(CC)CCCOC(=O)C1=CC=C(S(N)(=O)=O)C=C1 ACDPSQMEFRHYJP-UHFFFAOYSA-N 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 229960002610 apraclonidine Drugs 0.000 claims 1
- IEJXVRYNEISIKR-UHFFFAOYSA-N apraclonidine Chemical compound ClC1=CC(N)=CC(Cl)=C1NC1=NCCN1 IEJXVRYNEISIKR-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 35
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- 239000007787 solid Substances 0.000 description 33
- 150000003863 ammonium salts Chemical class 0.000 description 24
- 235000002639 sodium chloride Nutrition 0.000 description 19
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
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- 239000000126 substance Substances 0.000 description 9
- RSIYXJOWRJIOEC-UHFFFAOYSA-N 4-amino-n-(3-morpholin-4-ylpropyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NCCCN1CCOCC1 RSIYXJOWRJIOEC-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 8
- LFPUFCAIFUNCLI-UHFFFAOYSA-N 2-[4-(aminomethyl)phenoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(CN)C=C1 LFPUFCAIFUNCLI-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000004410 intraocular pressure Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000003389 potentiating effect Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
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- 125000001302 tertiary amino group Chemical group 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- AQOKCDNYWBIDND-FTOWTWDKSA-N bimatoprost Chemical compound CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1 AQOKCDNYWBIDND-FTOWTWDKSA-N 0.000 description 1
- 229960002470 bimatoprost Drugs 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000004406 elevated intraocular pressure Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- BUGQZUIRDSIVRZ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-sulfamoylbenzamide Chemical compound CN(C)CCNC(=O)C1=CC=C(S(N)(=O)=O)C=C1 BUGQZUIRDSIVRZ-UHFFFAOYSA-N 0.000 description 1
- 230000004493 normal intraocular pressure Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- CMHHMUWAYWTMGS-UHFFFAOYSA-N oxybuprocaine Chemical compound CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N CMHHMUWAYWTMGS-UHFFFAOYSA-N 0.000 description 1
- 229960003502 oxybuprocaine Drugs 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- 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
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- 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
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Ophthalmology & Optometry (AREA)
- AIDS & HIV (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (31)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SK54-2007A SK542007A3 (sk) | 2007-04-20 | 2007-04-20 | Substituované sulfónamidy, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
| TW097108546A TWI392492B (zh) | 2007-04-20 | 2008-03-11 | 經取代磺醯胺，其製法，包括該經取代磺醯胺之組成物及其用途 |
| ARP080101430A AR065966A1 (es) | 2007-04-20 | 2008-04-04 | Sulfonamidas substituidas, proceso para su preparacion, composicion farmaceutica de las mismas y su uso |
| JOP/2008/0180A JO3206B1 (ar) | 2007-04-20 | 2008-04-17 | سلفوناميدات مستبدلة وعملية لتحضيرها وتركيب صيدلى يشتمل عليها واستعمالها في علاج الجلوكوما |
| UY31028A UY31028A1 (es) | 2007-04-20 | 2008-04-17 | Sulfonamidas substituidas, proceso para su preparacion, composicion farmaceutica de las mismas y su uso. |
| RU2009134079/04A RU2474574C2 (ru) | 2007-04-20 | 2008-04-18 | Замещенные сульфонамиды, способ их получения, лекарственные препараты, которые их содержат, и их использование |
| CN200880012806A CN101663267A (zh) | 2007-04-20 | 2008-04-18 | 取代的磺酰胺、其制备方法、包含其的药物组合物及其应用 |
| SI200831379T SI2142499T1 (sl) | 2007-04-20 | 2008-04-18 | Substituirani sulfonamidi, postopek priprave le-teh, farmacevtski sestavek, vsebujoč le-te ter njihova uporaba za zdravljenje glavkoma |
| NZ581302A NZ581302A (en) | 2007-04-20 | 2008-04-18 | Subsituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use in treating glaucoma |
| HUE08741979A HUE024552T2 (hu) | 2007-04-20 | 2008-04-18 | Helyettesített szulfonamidok, eljárás elõállításukra, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk glaucoma kezelésére |
| JP2010504023A JP5492764B2 (ja) | 2007-04-20 | 2008-04-18 | 置換スルホンアミド、その製造方法、それを含有する製薬組成物及びその使用 |
| PT87419792T PT2142499E (pt) | 2007-04-20 | 2008-04-18 | Sulfonamidas substituídas, processo para a sua preparação, composição farmacêutica compreendendo-as e sua utilização para o tratamento de glaucoma |
| CL2008001109A CL2008001109A1 (es) | 2007-04-20 | 2008-04-18 | Compuestos derivados de sulfonamidas; procedimiento de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso para el tratamiento del glaucoma. |
| PCT/SK2008/050005 WO2008130332A1 (fr) | 2007-04-20 | 2008-04-18 | Sulfamides substitués, leur procédé de préparation, composition pharmaceutique en contenant et leur utilisation |
| MX2009010528A MX2009010528A (es) | 2007-04-20 | 2008-04-18 | Sulfonamidas sustituidas, procedimiento para su preparacion, composicion farmaceutica que comprende las mismas y su uso. |
| UAA200910016A UA99279C2 (ru) | 2007-04-20 | 2008-04-18 | Замещенные сульфонамиды, способ их получения, фармацевтическая композиция, которая их содержит, и их применение |
| CA2684591A CA2684591C (fr) | 2007-04-20 | 2008-04-18 | Sulfamides substitues, leur procede de preparation, composition pharmaceutique en contenant et leur utilisation |
| AU2008241590A AU2008241590B2 (en) | 2007-04-20 | 2008-04-18 | Substituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use |
| ES08741979.2T ES2528284T3 (es) | 2007-04-20 | 2008-04-18 | Sulfonamidas sustituidas, procedimiento para su preparación, composición farmacéutica que las contiene y su uso para tratar el glaucoma |
| EP08741979.2A EP2142499B1 (fr) | 2007-04-20 | 2008-04-18 | Sulfamides substitués, leur procédé de préparation, composition pharmaceutique en contenant et leur utilisation pour le traitement de glaucome |
| BRPI0809728A BRPI0809728A2 (pt) | 2007-04-20 | 2008-04-18 | "sulfonamidas substituídas, processo de preparação, composição farmacêutica que as compõem, assim como seu uso." |
| PE2008000680A PE20090807A1 (es) | 2007-04-20 | 2008-04-18 | Sulfonamidas substituidas, proceso para su preparacion y composicion farmaceutica de las mismas |
| DK08741979.2T DK2142499T3 (en) | 2007-04-20 | 2008-04-18 | Substituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use for the treatment of glaucoma |
| HRP20141246AT HRP20141246T1 (hr) | 2007-04-20 | 2008-04-18 | Supstituirani sulfonamidi, postupak za njihovu pripremu, farmaceutski sastavi koji ih sadrže i njihova upotreba za lijeäśenje glaukoma |
| PL08741979T PL2142499T3 (pl) | 2007-04-20 | 2008-04-18 | Podstawione sulfonamidy, sposób ich wytwarzania, zawierająca je kompozycja farmaceutyczna oraz ich zastosowanie do leczenia jaskry |
| SA08290238A SA08290238B1 (ar) | 2007-04-20 | 2008-04-19 | استخدام سلفونات أميد مستبدلة وعملية لتحضيرها وتركيبة دوائية تشملها |
| US12/596,820 US8193184B2 (en) | 2007-04-20 | 2008-04-20 | Substituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use |
| ZA200906305A ZA200906305B (en) | 2007-04-20 | 2009-09-10 | Substituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use |
| IL200952A IL200952A0 (en) | 2007-04-20 | 2009-09-15 | Substituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use |
| TNP2009000421A TN2009000421A1 (en) | 2007-04-20 | 2009-10-13 | Substituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use |
| MA32329A MA31364B1 (fr) | 2007-04-20 | 2009-11-05 | Sulfamides substitués, leur procédé de préparation, composition pharmaceutique en contenant et leur utilisation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SK54-2007A SK542007A3 (sk) | 2007-04-20 | 2007-04-20 | Substituované sulfónamidy, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK542007A3 true SK542007A3 (sk) | 2008-11-06 |
Family
ID=39671772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK54-2007A SK542007A3 (sk) | 2007-04-20 | 2007-04-20 | Substituované sulfónamidy, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US8193184B2 (fr) |
| EP (1) | EP2142499B1 (fr) |
| JP (1) | JP5492764B2 (fr) |
| CN (1) | CN101663267A (fr) |
| AR (1) | AR065966A1 (fr) |
| AU (1) | AU2008241590B2 (fr) |
| BR (1) | BRPI0809728A2 (fr) |
| CA (1) | CA2684591C (fr) |
| CL (1) | CL2008001109A1 (fr) |
| DK (1) | DK2142499T3 (fr) |
| ES (1) | ES2528284T3 (fr) |
| HR (1) | HRP20141246T1 (fr) |
| HU (1) | HUE024552T2 (fr) |
| IL (1) | IL200952A0 (fr) |
| JO (1) | JO3206B1 (fr) |
| MA (1) | MA31364B1 (fr) |
| MX (1) | MX2009010528A (fr) |
| NZ (1) | NZ581302A (fr) |
| PE (1) | PE20090807A1 (fr) |
| PL (1) | PL2142499T3 (fr) |
| PT (1) | PT2142499E (fr) |
| RU (1) | RU2474574C2 (fr) |
| SA (1) | SA08290238B1 (fr) |
| SI (1) | SI2142499T1 (fr) |
| SK (1) | SK542007A3 (fr) |
| TN (1) | TN2009000421A1 (fr) |
| TW (1) | TWI392492B (fr) |
| UA (1) | UA99279C2 (fr) |
| UY (1) | UY31028A1 (fr) |
| WO (1) | WO2008130332A1 (fr) |
| ZA (1) | ZA200906305B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115141128B (zh) * | 2022-06-24 | 2024-09-13 | 沈阳药科大学 | 3-芳基-3-(磺胺苯甲酰胺基)丙(烯)酸衍生物及其制备方法及应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789938A (en) * | 1952-11-24 | 1957-04-23 | Merck & Co Inc | Method of producing a diuretic effect with p-carboxybenzenesulfonamide |
| CH451142A (de) * | 1965-01-19 | 1968-05-15 | Sandoz Ag | Verfahren zur Herstellung neuer basisch substituierter Benzoesäureamide |
| GB1523631A (en) * | 1975-07-08 | 1978-09-06 | Leo Pharm Prod Ltd | Sulphonamide derivatives |
| EP0029090A3 (fr) * | 1979-09-28 | 1981-07-01 | American Cyanamid Company | Sulfonamides contenant un phénol stériquement empêché; composition stabilisée à base d'un polymère synthétique et des sulfonamides mentionnés |
| FR2504528A1 (fr) * | 1981-04-23 | 1982-10-29 | Choay Sa | Dialcoxy (2,4) benzenesulfonamides n-substitues |
| JPS5939867A (ja) * | 1982-08-27 | 1984-03-05 | Fuji Yakuhin Kogyo Kk | ２−クロロスルホニル−４−ｎ−置換スルフアミル−クロロベンゼンの製造法 |
| JPS6041071B2 (ja) * | 1983-07-28 | 1985-09-13 | ソシエテ・デチユ−デ・シヤンテイフイツク・エ・アンデユストリエル・ドウ・リル−ドウ−フランス | 安息香酸誘導体 |
| US4678855A (en) * | 1985-10-09 | 1987-07-07 | Merck & Co., Inc. | Substituted benzenesulfonamides |
| US4721809A (en) * | 1986-09-18 | 1988-01-26 | American Home Products Corporation | Alkylsulfonamido or perfluoroalkylsulfonamido benzenesulfonamides |
| ES2199247T3 (es) * | 1994-03-11 | 2004-02-16 | Pharmacopeia Drug Discovery, Inc. | Derivados de sulfonamida y su uso. |
| JP2001162950A (ja) * | 1999-12-13 | 2001-06-19 | Fuji Photo Film Co Ltd | 感熱記録材料 |
| JP4139712B2 (ja) * | 2002-03-14 | 2008-08-27 | ライオン株式会社 | 漂白活性化剤及び漂白剤組成物 |
| DK1765454T3 (en) * | 2004-07-02 | 2016-05-02 | Mati Therapeutics Inc | Device for submission of treatment medium to eye |
| SE0401969D0 (sv) * | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Piperidine derivatives |
| WO2008071421A1 (fr) * | 2006-12-15 | 2008-06-19 | Nicox S.A. | Esters de l'acide nitrique des inhibiteurs d'anhydrase carbonique |
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