SK17698A3 - Sulfonamide substituted compounds, a medicament containing same and their use - Google Patents

Sulfonamide substituted compounds, a medicament containing same and their use Download PDF

Info

Publication number: SK17698A3
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; trifluoromethyl; atom; methyl
Prior art date: 1997-02-11

Application number

SK176-98A

Other languages

English (en)

Slovak (sk)

Inventor

Uwe Gerlach

Joachim Brendel

Hans J Lang

Klaus Weidmann

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1997-02-11

Filing date

1998-02-09

Publication date

1998-09-09

1998-02-09 Application filed by Hoechst Ag filed Critical Hoechst Ag

1998-09-09 Publication of SK17698A3 publication Critical patent/SK17698A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 64
239000003814 drug Substances 0.000 title claims description 20
125000000565 sulfonamide group Chemical group 0.000 title claims 2
229940124530 sulfonamide Drugs 0.000 title description 9
-1 N-morpholino Chemical group 0.000 claims abstract description 146
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 120
229910052801 chlorine Inorganic materials 0.000 claims abstract description 84
125000000217 alkyl group Chemical group 0.000 claims abstract description 78
229910052731 fluorine Inorganic materials 0.000 claims abstract description 78
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 75
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 70
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 53
125000002947 alkylene group Chemical group 0.000 claims abstract description 52
229910052794 bromium Inorganic materials 0.000 claims abstract description 50
125000005936 piperidyl group Chemical group 0.000 claims abstract description 31
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 30
229910052740 iodine Inorganic materials 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 20
229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
125000004423 acyloxy group Chemical group 0.000 claims abstract description 11
229910052799 carbon Inorganic materials 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 178
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 95
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 88
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 80
239000001257 hydrogen Substances 0.000 claims description 69
125000006343 heptafluoro propyl group Chemical group 0.000 claims description 60
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 60
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 59
125000001424 substituent group Chemical group 0.000 claims description 58
125000001153 fluoro group Chemical group F* 0.000 claims description 54
150000002431 hydrogen Chemical class 0.000 claims description 50
239000000460 chlorine Substances 0.000 claims description 49
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 46
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 46
239000011737 fluorine Substances 0.000 claims description 42
125000001309 chloro group Chemical group Cl* 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
125000004430 oxygen atom Chemical group O* 0.000 claims description 30
125000002883 imidazolyl group Chemical group 0.000 claims description 29
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
125000001544 thienyl group Chemical group 0.000 claims description 23
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 22
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
125000004076 pyridyl group Chemical group 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 18
238000011282 treatment Methods 0.000 claims description 16
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 15
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000005956 isoquinolyl group Chemical group 0.000 claims description 10
125000005493 quinolyl group Chemical group 0.000 claims description 10
206010003119 arrhythmia Diseases 0.000 claims description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
101150020251 NR13 gene Proteins 0.000 claims description 5
230000006793 arrhythmia Effects 0.000 claims description 5
150000001540 azides Chemical class 0.000 claims description 5
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
230000000903 blocking effect Effects 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
206010003658 Atrial Fibrillation Diseases 0.000 claims description 2
206010012735 Diarrhoea Diseases 0.000 claims description 2
208000007107 Stomach Ulcer Diseases 0.000 claims description 2
206010049418 Sudden Cardiac Death Diseases 0.000 claims description 2
206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 2
206010047281 Ventricular arrhythmia Diseases 0.000 claims description 2
230000000747 cardiac effect Effects 0.000 claims description 2
230000002496 gastric effect Effects 0.000 claims description 2
208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 2
208000000689 peptic esophagitis Diseases 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
230000002861 ventricular Effects 0.000 claims description 2
208000003663 ventricular fibrillation Diseases 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
239000001301 oxygen Substances 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
206010022714 Intestinal ulcer Diseases 0.000 claims 1
230000036982 action potential Effects 0.000 claims 1
230000001746 atrial effect Effects 0.000 claims 1
208000035475 disorder Diseases 0.000 claims 1
230000027119 gastric acid secretion Effects 0.000 claims 1
230000010355 oscillation Effects 0.000 claims 1
125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
230000033764 rhythmic process Effects 0.000 claims 1
229910002091 carbon monoxide Inorganic materials 0.000 abstract 2
229910052717 sulfur Inorganic materials 0.000 abstract 2
101000869592 Daucus carota Major allergen Dau c 1 Proteins 0.000 abstract 1
101000650136 Homo sapiens WAS/WASL-interacting protein family member 3 Proteins 0.000 abstract 1
102100027539 WAS/WASL-interacting protein family member 3 Human genes 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
108091006146 Channels Proteins 0.000 description 11
230000008569 process Effects 0.000 description 10
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 8
150000003456 sulfonamides Chemical class 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000009471 action Effects 0.000 description 5
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
FSOABSKPUNBUIA-UHFFFAOYSA-N 3,3-dimethyl-2,4-dihydronaphthalen-1-one Chemical compound C1=CC=C2CC(C)(C)CC(=O)C2=C1 FSOABSKPUNBUIA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 2
ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 2
DBUVJCMIFADARZ-UHFFFAOYSA-N 1-phenyl-2,3-dihydroquinolin-4-one Chemical compound C12=CC=CC=C2C(=O)CCN1C1=CC=CC=C1 DBUVJCMIFADARZ-UHFFFAOYSA-N 0.000 description 2
XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
OBUSDOCQRDNLMK-UHFFFAOYSA-N 7,7-dimethyl-5-oxo-6,8-dihydronaphthalene-1-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2CC(C)(C)CC(=O)C2=C1 OBUSDOCQRDNLMK-UHFFFAOYSA-N 0.000 description 2
ASDSSALPMXLNCA-UHFFFAOYSA-N 7-nitro-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(N)CCCC2=C1 ASDSSALPMXLNCA-UHFFFAOYSA-N 0.000 description 2
GWAQYWSNCVEJMW-UHFFFAOYSA-N 7-nitro-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC([N+](=O)[O-])=CC=C21 GWAQYWSNCVEJMW-UHFFFAOYSA-N 0.000 description 2
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
102000004257 Potassium Channel Human genes 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
230000003288 anthiarrhythmic effect Effects 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
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 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
229950004210 cromakalim Drugs 0.000 description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000007336 electrophilic substitution reaction Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
235000001727 glucose Nutrition 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
OCQWTVFWBULPAL-UHFFFAOYSA-N methyl 5-amino-7,7-dimethyl-6,8-dihydro-5h-naphthalene-1-carboxylate Chemical compound NC1CC(C)(C)CC2=C1C=CC=C2C(=O)OC OCQWTVFWBULPAL-UHFFFAOYSA-N 0.000 description 2
MDLXXYXMTCHKDR-UHFFFAOYSA-N n-(3,3-dimethyl-2,4-dihydro-1h-naphthalen-1-yl)-n-methylmethanesulfonamide Chemical compound C1=CC=C2C(N(C)S(C)(=O)=O)CC(C)(C)CC2=C1 MDLXXYXMTCHKDR-UHFFFAOYSA-N 0.000 description 2
WLLUSICJOIXZMI-UHFFFAOYSA-N n-(3,3-dimethyl-7-nitro-2,4-dihydro-1h-naphthalen-1-yl)-n-methylmethanesulfonamide Chemical compound C1=C([N+]([O-])=O)C=C2C(N(C)S(C)(=O)=O)CC(C)(C)CC2=C1 WLLUSICJOIXZMI-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
108020001213 potassium channel Proteins 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
230000002040 relaxant effect Effects 0.000 description 2
230000028327 secretion Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
XMSJNFPFPZYDQQ-UHFFFAOYSA-N 1,1,2-tri(propan-2-yl)guanidine Chemical compound CC(C)N=C(N)N(C(C)C)C(C)C XMSJNFPFPZYDQQ-UHFFFAOYSA-N 0.000 description 1
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 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
PHFFZLIQGNLRRH-BYEGLACWSA-N 1-[(e)-[5-(4-chlorophenyl)furan-2-yl]methylideneamino]-3-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]imidazolidine-2,4-dione;dihydrochloride Chemical compound Cl.Cl.C1CN(CCO)CCN1CCCN1C(=O)N(\N=C\C=2OC(=CC=2)C=2C=CC(Cl)=CC=2)CC1=O PHFFZLIQGNLRRH-BYEGLACWSA-N 0.000 description 1
MREBEPTUUMTTIA-XYGWBWBKSA-N 1-[(z)-[5-(4-chlorophenyl)furan-2-yl]methylideneamino]-3-[4-(4-methylpiperazin-1-yl)butyl]imidazolidine-2,4-dione Chemical compound C1CN(C)CCN1CCCCN1C(=O)N(\N=C/C=2OC(=CC=2)C=2C=CC(Cl)=CC=2)CC1=O MREBEPTUUMTTIA-XYGWBWBKSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
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 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
241000269370 Xenopus <genus> Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000001346 alkyl aryl ethers Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
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239000003963 antioxidant agent Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000011575 calcium Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000004413 cardiac myocyte Anatomy 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000020411 cell activation Effects 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
239000000032 diagnostic agent Substances 0.000 description 1
229940039227 diagnostic agent Drugs 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
238000007908 dry granulation Methods 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000021323 fish oil Nutrition 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
230000002102 hyperpolarization Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
150000002641 lithium Chemical group 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000001055 magnesium Nutrition 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
229940049920 malate Drugs 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
PSBBCMSHYXJCOM-UHFFFAOYSA-N methyl 5-(methanesulfonamido)-7,7-dimethyl-6,8-dihydro-5h-naphthalene-1-carboxylate Chemical compound CS(=O)(=O)NC1CC(C)(C)CC2=C1C=CC=C2C(=O)OC PSBBCMSHYXJCOM-UHFFFAOYSA-N 0.000 description 1
GLJBGBIBIKPQJC-UHFFFAOYSA-N methyl 5-[hexyl(methylsulfonyl)amino]-7,7-dimethyl-6,8-dihydro-5h-naphthalene-1-carboxylate Chemical compound C1=CC=C(C(=O)OC)C2=C1C(N(CCCCCC)S(C)(=O)=O)CC(C)(C)C2 GLJBGBIBIKPQJC-UHFFFAOYSA-N 0.000 description 1
NPZNMBZVCWHMKN-UHFFFAOYSA-N methyl 7,7-dimethyl-5-(methylsulfonylmethylamino)-6,8-dihydro-5H-naphthalene-1-carboxylate Chemical compound CS(=O)(=O)CNC1CC(C)(C)CC2=C1C=CC=C2C(=O)OC NPZNMBZVCWHMKN-UHFFFAOYSA-N 0.000 description 1
JPBAWARNVNPWLX-UHFFFAOYSA-N methyl 7,7-dimethyl-5-oxo-6,8-dihydronaphthalene-1-carboxylate Chemical compound O=C1CC(C)(C)CC2=C1C=CC=C2C(=O)OC JPBAWARNVNPWLX-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004118 muscle contraction Effects 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
MOJQCTLZAIOIGJ-UHFFFAOYSA-N n-butyl-n-(1,2,3,4-tetrahydronaphthalen-1-yl)ethanesulfonamide Chemical compound C1=CC=C2C(N(CCCC)S(=O)(=O)CC)CCCC2=C1 MOJQCTLZAIOIGJ-UHFFFAOYSA-N 0.000 description 1
XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
CQEBDPCUDWZCFN-UHFFFAOYSA-N n-methyl-n-(1,2,3,4-tetrahydronaphthalen-1-yl)ethanesulfonamide Chemical compound C1=CC=C2C(N(C)S(=O)(=O)CC)CCCC2=C1 CQEBDPCUDWZCFN-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
210000000287 oocyte Anatomy 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000004036 potassium channel stimulating agent Substances 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000033904 relaxation of vascular smooth muscle Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
125000004436 sodium atom Chemical group 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/07—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (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)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Quinoline Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

SK176-98A 1997-02-11 1998-02-09 Sulfonamide substituted compounds, a medicament containing same and their use SK17698A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19705133A DE19705133A1 (de)	1997-02-11	1997-02-11	Sulfonamid-substituierte Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

Publications (1)

Publication Number	Publication Date
SK17698A3 true SK17698A3 (en)	1998-09-09

Family

ID=7819888

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK176-98A SK17698A3 (en)	1997-02-11	1998-02-09	Sulfonamide substituted compounds, a medicament containing same and their use

Country Status (22)

Country	Link
US (1)	US6087399A (fr)
EP (1)	EP0857724A1 (fr)
JP (1)	JPH10218855A (fr)
KR (1)	KR19980071212A (fr)
CN (1)	CN1193012A (fr)
AR (1)	AR011115A1 (fr)
AU (1)	AU727216B2 (fr)
BR (1)	BR9800596A (fr)
CA (1)	CA2227930A1 (fr)
CZ (1)	CZ38598A3 (fr)
DE (1)	DE19705133A1 (fr)
HR (1)	HRP980066B1 (fr)
HU (1)	HUP9800277A3 (fr)
ID (1)	ID21266A (fr)
IL (1)	IL123229A (fr)
NO (1)	NO311567B1 (fr)
NZ (1)	NZ329716A (fr)
PL (1)	PL324768A1 (fr)
SK (1)	SK17698A3 (fr)
TR (1)	TR199800195A2 (fr)
TW (1)	TW450967B (fr)
ZA (1)	ZA981063B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69621482D1 (de) *	1995-02-09	2002-07-11	Canon Kk	Druckersystem, Drucker, Datenverarbeitungsgerät und Charaktersatzspeicher-Herunterladungssteuerprogramm
CZ302691B6 (cs)	1998-07-08	2011-09-07	Sanofi - Aventis Deutschland GmbH	N-Arylamidová sloucenina, zpusob její prípravy, farmaceutický prostredek tuto slouceninu obsahující, tato sloucenina pro použití jako aktivátor a pro použití k terapii nebo profylaxi
TW200403058A (en)	2002-04-19	2004-03-01	Bristol Myers Squibb Co	Heterocyclo inhibitors of potassium channel function
JP2009026126A (ja) *	2007-07-20	2009-02-05	Nec Electronics Corp	半導体装置

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EP0386839B1 (fr) *	1989-03-08	1997-01-15	Merck Sharp & Dohme Ltd.	Dérivés de tétrahydroquinoléine utiles pour les affections neurodégénératives
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1997
- 1997-02-11 DE DE19705133A patent/DE19705133A1/de not_active Withdrawn
1998
- 1998-01-27 CA CA002227930A patent/CA2227930A1/fr not_active Abandoned
- 1998-02-05 EP EP98101980A patent/EP0857724A1/fr not_active Withdrawn
- 1998-02-09 NZ NZ329716A patent/NZ329716A/xx unknown
- 1998-02-09 SK SK176-98A patent/SK17698A3/sk unknown
- 1998-02-09 CZ CZ98385A patent/CZ38598A3/cs unknown
- 1998-02-09 AR ARP980100549A patent/AR011115A1/es unknown
- 1998-02-09 IL IL12322998A patent/IL123229A/en not_active IP Right Cessation
- 1998-02-09 TR TR1998/00195A patent/TR199800195A2/xx unknown
- 1998-02-09 ID IDP980154A patent/ID21266A/id unknown
- 1998-02-10 KR KR1019980003769A patent/KR19980071212A/ko not_active Withdrawn
- 1998-02-10 CN CN98106455A patent/CN1193012A/zh active Pending
- 1998-02-10 JP JP10028635A patent/JPH10218855A/ja active Pending
- 1998-02-10 AU AU53860/98A patent/AU727216B2/en not_active Ceased
- 1998-02-10 ZA ZA981063A patent/ZA981063B/xx unknown
- 1998-02-10 NO NO19980564A patent/NO311567B1/no not_active IP Right Cessation
- 1998-02-10 HU HU9800277A patent/HUP9800277A3/hu unknown
- 1998-02-10 HR HR980066A patent/HRP980066B1/xx not_active IP Right Cessation
- 1998-02-11 PL PL98324768A patent/PL324768A1/xx unknown
- 1998-02-11 BR BR9800596A patent/BR9800596A/pt not_active IP Right Cessation
- 1998-03-02 TW TW087101663A patent/TW450967B/zh not_active IP Right Cessation
1999
- 1999-04-27 US US09/299,726 patent/US6087399A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU5386098A (en)	1998-08-13
NO980564D0 (no)	1998-02-10
US6087399A (en)	2000-07-11
NO311567B1 (no)	2001-12-10
CA2227930A1 (fr)	1998-08-11
HRP980066A2 (en)	1998-10-31
CN1193012A (zh)	1998-09-16
ID21266A (id)	1999-05-12
JPH10218855A (ja)	1998-08-18
HUP9800277A2 (hu)	1999-06-28
AU727216B2 (en)	2000-12-07
AR011115A1 (es)	2000-08-02
EP0857724A1 (fr)	1998-08-12
IL123229A (en)	2002-04-21
TR199800195A2 (xx)	1998-09-21
NO980564L (no)	1998-08-12
BR9800596A (pt)	1999-07-20
CZ38598A3 (cs)	1998-08-12
NZ329716A (en)	2000-01-28
DE19705133A1 (de)	1998-08-13
TW450967B (en)	2001-08-21
HRP980066B1 (en)	2002-06-30
IL123229A0 (en)	1998-09-24
ZA981063B (en)	1998-08-11
KR19980071212A (ko)	1998-10-26
MX9801121A (es)	1998-08-30
HUP9800277A3 (en)	2000-01-28
HU9800277D0 (en)	1998-04-28
PL324768A1 (en)	1998-08-17

Publication	Publication Date	Title
EP0261539B1 (fr)	1991-03-06	Phénylsulfonamides substitués
KR20040030668A (ko)	2004-04-09	헤테로아릴설포닐 측쇄를 갖는 안트라닐산 아미드, 이의제조방법, 약제 또는 진단제로서의 이의 용도 및 당해화합물을 함유하는 약제학적 제제
EP0906911B1 (fr)	2004-04-28	Dérivés sulfonamide de chromane substitués ayant une activité de bloquage de canaux de potassium, procédé pour leur préparation, utilisation comme médicaments et compositions pharmaceutiques les contenant
ES2234044T3 (es)	2005-06-16	Compuestos anulares de siete miembros, condensados sustituidos con sulfonamido con actividad bloqueante del canal de potasio.
EP0915087B1 (fr)	2003-04-02	Composés cycliques à cinq chaínons annelés portant un groupe sulfonamide, leur utilisation comme médicaments ainsi que compositions pharmaceutiques les contenant
SK17698A3 (en)	1998-09-09	Sulfonamide substituted compounds, a medicament containing same and their use
US6184221B1 (en)	2001-02-06	Sulfonamide-substituted compounds, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them
JP4317601B2 (ja)	2009-08-19	スルホンアミド−置換された化合物、それらの製法、医薬または診断薬としてのそれらの使用およびそれらを含有する医薬製剤
DE19742509A1 (de)	1999-04-01	Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen
MXPA98001121A (en)	1998-11-12	Compositions replaced with sulfonamide, procedure for its preparation, its employment as a diagnostic medicine or agent as well as a medicine that conti
HK1017680A (en)	1999-11-26	Sulfonamide-substituted compounds, processes for their prepartion, their use as a medicament oder diagnostic, and medicament comprising them
DE19730326A1 (de)	1999-01-21	Sulfonamid-substituierte Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen
MXPA97010126A (en)	1998-11-09	Substituted compounds with sulfonamide, procedure for preparation, employment as a medicine or diagnostic agent, as well as pharmaceutical preparations that contain them
WO1998037083A1 (fr)	1998-08-27	Thiophenes substitues par un sulfamide, mode de fabrication et utilisation en tant que medicament ou agent diagnostique, et medicament contenant de tels thiophenes
DE19652213A1 (de)	1998-06-18	Sulfonamid-substituierte Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE19733779A1 (de)	1999-02-11	Sulfonamid-substituierte Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
MXPA98006267A (en)	1999-04-27	Substituted compounds with sulfonamide, procedure for its preparation, its use as a diagnostic medicine or agent as well as a medicine that contains them