HRP980098A2 - Sulfonamido substituted condensed, seven-membered ring compounds, their use as medicines and pharmaceutical preparations containing them - Google Patents
Sulfonamido substituted condensed, seven-membered ring compounds, their use as medicines and pharmaceutical preparations containing themInfo
- Publication number
- HRP980098A2 HRP980098A2 HR19707656.4A HRP980098A HRP980098A2 HR P980098 A2 HRP980098 A2 HR P980098A2 HR P980098 A HRP980098 A HR P980098A HR P980098 A2 HRP980098 A2 HR P980098A2
- Authority
- HR
- Croatia
- Prior art keywords
- hydrogen
- group
- carbon atoms
- alkyl
- residues
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 96
- 239000003814 drug Substances 0.000 title claims description 29
- 229940079593 drug Drugs 0.000 title claims description 22
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 158
- 239000001257 hydrogen Substances 0.000 claims description 141
- 229910052739 hydrogen Inorganic materials 0.000 claims description 141
- -1 methoxy, dimethylamino, sulfamoyl Chemical group 0.000 claims description 123
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 150000002431 hydrogen Chemical class 0.000 claims description 70
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
- 229910052794 bromium Inorganic materials 0.000 claims description 53
- 229910052801 chlorine Inorganic materials 0.000 claims description 53
- 229910052731 fluorine Inorganic materials 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 49
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
- 125000001544 thienyl group Chemical group 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 30
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 28
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 238000011321 prophylaxis Methods 0.000 claims description 21
- 238000002560 therapeutic procedure Methods 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 239000013543 active substance Substances 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 206010003119 arrhythmia Diseases 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 230000006793 arrhythmia Effects 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 206010003662 Atrial flutter Diseases 0.000 claims description 5
- 210000002784 stomach Anatomy 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 206010012735 Diarrhoea Diseases 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 4
- 230000036982 action potential Effects 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 230000028327 secretion Effects 0.000 claims description 4
- 231100000397 ulcer Toxicity 0.000 claims description 4
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010049418 Sudden Cardiac Death Diseases 0.000 claims description 3
- 206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 3
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 3
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 3
- 230000000968 intestinal effect Effects 0.000 claims description 3
- 208000000689 peptic esophagitis Diseases 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 230000002861 ventricular Effects 0.000 claims description 3
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 2
- 208000008131 Ventricular Flutter Diseases 0.000 claims description 2
- 230000001746 atrial effect Effects 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 230000033764 rhythmic process Effects 0.000 claims description 2
- 210000004211 gastric acid Anatomy 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000003663 ventricular fibrillation Diseases 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 235000002639 sodium chloride Nutrition 0.000 description 33
- 239000000243 solution Substances 0.000 description 31
- 239000000460 chlorine Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 238000000034 method Methods 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 230000009471 action Effects 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 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 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 229940124530 sulfonamide Drugs 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 238000005804 alkylation reaction Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 150000003456 sulfonamides Chemical class 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 210000000287 oocyte Anatomy 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000029936 alkylation Effects 0.000 description 6
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003416 antiarrhythmic agent Substances 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- QJQARXIEBJBMRM-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1-benzoxepin-5-amine Chemical compound NC1CCCOC2=CC=CC=C12 QJQARXIEBJBMRM-UHFFFAOYSA-N 0.000 description 4
- XKLXISLVCPHTBP-UHFFFAOYSA-N 7-butoxy-3,4-dihydro-2h-1-benzoxepin-5-one Chemical compound O1CCCC(=O)C2=CC(OCCCC)=CC=C21 XKLXISLVCPHTBP-UHFFFAOYSA-N 0.000 description 4
- QYQASVFLGKZSDY-UHFFFAOYSA-N 7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepin-5-amine Chemical compound NC1CCCOC2=C1C=C(Cl)C=C2C QYQASVFLGKZSDY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- 108091006146 Channels Proteins 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 241000269370 Xenopus <genus> Species 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 229940082627 class iii antiarrhythmics Drugs 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- RXJABQVUUIEBPN-UHFFFAOYSA-N n-(2,3,4,5-tetrahydro-1-benzoxepin-5-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1CCCOC2=CC=CC=C12 RXJABQVUUIEBPN-UHFFFAOYSA-N 0.000 description 4
- GPOBCZJJYHHURS-UHFFFAOYSA-N n-(3-fluoro-6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-yl)ethanesulfonamide Chemical compound CCS(=O)(=O)NC1CCCCC2=CC=C(F)C=C12 GPOBCZJJYHHURS-UHFFFAOYSA-N 0.000 description 4
- YPNUCOGOQRPGOQ-UHFFFAOYSA-N n-methyl-n-trimethylsilylethanesulfonamide Chemical compound CCS(=O)(=O)N(C)[Si](C)(C)C YPNUCOGOQRPGOQ-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- KNTMEDNZPJADJU-UHFFFAOYSA-N 3,4-dihydro-2h-1-benzoxepin-5-one Chemical compound O=C1CCCOC2=CC=CC=C12 KNTMEDNZPJADJU-UHFFFAOYSA-N 0.000 description 3
- GNYVDKZVCARRFI-UHFFFAOYSA-N 7-nitro-1a,2,3,8b-tetrahydrooxireno[2,3-d][1]benzoxepine Chemical compound O1CCC2OC2C2=CC([N+](=O)[O-])=CC=C21 GNYVDKZVCARRFI-UHFFFAOYSA-N 0.000 description 3
- FBRORVGGWHTZRD-UHFFFAOYSA-N 7-nitro-2,3-dihydro-1-benzoxepine Chemical compound O1CCC=CC2=CC([N+](=O)[O-])=CC=C21 FBRORVGGWHTZRD-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 150000001336 alkenes Chemical group 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 210000004413 cardiac myocyte Anatomy 0.000 description 3
- 210000001072 colon Anatomy 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 3
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 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
- 238000001802 infusion Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- FJCDITXLMZHSID-DGCLKSJQSA-N n-[(4r,5r)-4-hydroxy-7-nitro-2,3,4,5-tetrahydro-1-benzoxepin-5-yl]-n-methylethanesulfonamide Chemical compound CCS(=O)(=O)N(C)[C@H]1[C@H](O)CCOC2=CC=C([N+]([O-])=O)C=C12 FJCDITXLMZHSID-DGCLKSJQSA-N 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 210000002460 smooth muscle Anatomy 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 2
- JOXZTUJZGKRJGL-UHFFFAOYSA-N 4-(sulfonylamino)-3,4-dihydro-2h-chromene Chemical group C1=CC=C2C(N=S(=O)=O)CCOC2=C1 JOXZTUJZGKRJGL-UHFFFAOYSA-N 0.000 description 2
- MBGGFXOXUIDRJD-UHFFFAOYSA-N 4-Butoxyphenol Chemical compound CCCCOC1=CC=C(O)C=C1 MBGGFXOXUIDRJD-UHFFFAOYSA-N 0.000 description 2
- BXQCAAAJCZAMKV-UHFFFAOYSA-N 7-chloro-9-methyl-3,4-dihydro-2h-1-benzoxepin-5-one Chemical compound O1CCCC(=O)C2=C1C(C)=CC(Cl)=C2 BXQCAAAJCZAMKV-UHFFFAOYSA-N 0.000 description 2
- SICRGBQSJUIEMG-UHFFFAOYSA-N 7-nitro-2,3,4,5-tetrahydro-1-benzoxepin-5-amine Chemical compound NC1CCCOC2=CC=C([N+]([O-])=O)C=C12 SICRGBQSJUIEMG-UHFFFAOYSA-N 0.000 description 2
- HCJDDRWAVYLBCZ-UHFFFAOYSA-N 7-nitro-3,4-dihydro-2h-1-benzoxepin-5-one Chemical compound O1CCCC(=O)C2=CC([N+](=O)[O-])=CC=C21 HCJDDRWAVYLBCZ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
- C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (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)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19707656A DE19707656A1 (de) | 1997-02-26 | 1997-02-26 | Sulfonamid-substituierte anellierte 7-Ring-Verbindungen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980098A2 true HRP980098A2 (en) | 1998-12-31 |
Family
ID=7821518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR19707656.4A HRP980098A2 (en) | 1997-02-26 | 1998-02-25 | Sulfonamido substituted condensed, seven-membered ring compounds, their use as medicines and pharmaceutical preparations containing them |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0861836B1 (cs) |
| JP (1) | JP4171097B2 (cs) |
| KR (1) | KR19980071625A (cs) |
| CN (1) | CN1110490C (cs) |
| AR (1) | AR011163A1 (cs) |
| AT (1) | ATE286039T1 (cs) |
| AU (1) | AU737461B2 (cs) |
| BR (1) | BR9800207A (cs) |
| CA (1) | CA2230349A1 (cs) |
| CZ (1) | CZ53998A3 (cs) |
| DE (2) | DE19707656A1 (cs) |
| ES (1) | ES2234044T3 (cs) |
| HR (1) | HRP980098A2 (cs) |
| HU (1) | HUP9800395A3 (cs) |
| ID (1) | ID19931A (cs) |
| IL (1) | IL123454A0 (cs) |
| MX (1) | MX9801516A (cs) |
| NO (1) | NO980785L (cs) |
| NZ (1) | NZ329838A (cs) |
| PL (1) | PL325045A1 (cs) |
| RU (1) | RU2223264C2 (cs) |
| SK (1) | SK283312B6 (cs) |
| TR (1) | TR199800301A2 (cs) |
| TW (1) | TW452574B (cs) |
| ZA (1) | ZA981562B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19858253A1 (de) * | 1998-12-17 | 2000-06-21 | Aventis Pharma Gmbh | Verwendung von Inhibitoren des KQt1-Kanals zur Herstellung eines Medikaments zur Behandlung von Krankheiten, die durch Helminthen und Ektoparasiten hervorgerufen werden |
| DE19929076A1 (de) * | 1999-06-25 | 2000-12-28 | Aventis Pharma Gmbh | Indanylsubstituierte Benzolcarbonamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| US7119112B2 (en) * | 2002-02-28 | 2006-10-10 | Icagen, Inc. | Sulfonamides as potassium channel blockers |
| TW200403058A (en) | 2002-04-19 | 2004-03-01 | Bristol Myers Squibb Co | Heterocyclo inhibitors of potassium channel function |
| AU2003291310A1 (en) | 2002-11-06 | 2004-06-03 | Bristol-Myers Squibb Company | Fused heterocyclic compounds and use thereof |
| JP4502280B2 (ja) * | 2005-03-31 | 2010-07-14 | 塩野義製薬株式会社 | スルファミンカルボン酸誘導体の製造方法 |
| RU2405777C1 (ru) * | 2009-05-13 | 2010-12-10 | Государственное образовательное учреждение высшего профессионального образования "Пермский государственный университет" | СПОСОБ ПОЛУЧЕНИЯ 4-БЕНЗОИЛ-1Н-БЕНЗО[c]ОКСЕПИН-3-ОНА |
| US20120309796A1 (en) * | 2011-06-06 | 2012-12-06 | Fariborz Firooznia | Benzocycloheptene acetic acids |
| RU2538962C1 (ru) * | 2013-11-19 | 2015-01-10 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования "Казанский (Приволжский) Федеральный Университет" (ФГАОУ ВПО КФУ) | Противогрибковые соединения на основе производных 3,5,8-триоксабицикло[5.1.0]октана |
| WO2020193419A1 (en) * | 2019-03-22 | 2020-10-01 | Saniona A/S | Novel potassium channel inhibitors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE464194B (sv) * | 1983-03-04 | 1991-03-18 | Otsuka Pharma Co Ltd | Indanderivat, foerfarande foer framstaellning daerav samt farmaceutiska kompositioner |
| US5258510A (en) * | 1989-10-20 | 1993-11-02 | Otsuka Pharma Co Ltd | Benzoheterocyclic compounds |
| US5428031A (en) * | 1991-12-03 | 1995-06-27 | Merck & Co., Inc. | Methods of treating cardiac arrhythmia |
| GB9225860D0 (en) * | 1992-12-11 | 1993-02-03 | Smithkline Beecham Plc | Novel treatment |
| FR2711139B1 (fr) * | 1993-10-15 | 1995-12-01 | Adir | Nouveaux dérivés de 1,2,3,4-tétrahydronaphtalène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
-
1997
- 1997-02-26 DE DE19707656A patent/DE19707656A1/de not_active Withdrawn
-
1998
- 1998-02-20 AT AT98102952T patent/ATE286039T1/de not_active IP Right Cessation
- 1998-02-20 BR BR9800207A patent/BR9800207A/pt not_active IP Right Cessation
- 1998-02-20 ES ES98102952T patent/ES2234044T3/es not_active Expired - Lifetime
- 1998-02-20 DE DE59812423T patent/DE59812423D1/de not_active Expired - Lifetime
- 1998-02-20 EP EP98102952A patent/EP0861836B1/de not_active Expired - Lifetime
- 1998-02-24 CA CA002230349A patent/CA2230349A1/en not_active Abandoned
- 1998-02-24 AR ARP980100811A patent/AR011163A1/es unknown
- 1998-02-24 ID IDP980258A patent/ID19931A/id unknown
- 1998-02-24 SK SK239-98A patent/SK283312B6/sk unknown
- 1998-02-24 CZ CZ98539A patent/CZ53998A3/cs unknown
- 1998-02-24 KR KR1019980005695A patent/KR19980071625A/ko not_active Ceased
- 1998-02-24 TR TR1998/00301A patent/TR199800301A2/xx unknown
- 1998-02-24 NZ NZ329838A patent/NZ329838A/xx unknown
- 1998-02-25 ZA ZA981562A patent/ZA981562B/xx unknown
- 1998-02-25 NO NO980785A patent/NO980785L/no unknown
- 1998-02-25 MX MX9801516A patent/MX9801516A/es not_active IP Right Cessation
- 1998-02-25 HU HU9800395A patent/HUP9800395A3/hu unknown
- 1998-02-25 RU RU98104586/04A patent/RU2223264C2/ru not_active IP Right Cessation
- 1998-02-25 CN CN98105329A patent/CN1110490C/zh not_active Expired - Fee Related
- 1998-02-25 IL IL12345498A patent/IL123454A0/xx unknown
- 1998-02-25 AU AU56333/98A patent/AU737461B2/en not_active Ceased
- 1998-02-25 HR HR19707656.4A patent/HRP980098A2/hr not_active Application Discontinuation
- 1998-02-25 JP JP04365298A patent/JP4171097B2/ja not_active Expired - Fee Related
- 1998-02-26 PL PL98325045A patent/PL325045A1/xx unknown
- 1998-03-27 TW TW087102578A patent/TW452574B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO980785D0 (no) | 1998-02-25 |
| NO980785L (no) | 1998-08-27 |
| ES2234044T3 (es) | 2005-06-16 |
| ZA981562B (en) | 1998-08-26 |
| TW452574B (en) | 2001-09-01 |
| DE19707656A1 (de) | 1998-08-27 |
| EP0861836A1 (de) | 1998-09-02 |
| SK283312B6 (sk) | 2003-05-02 |
| MX9801516A (es) | 1998-11-30 |
| BR9800207A (pt) | 1999-05-18 |
| IL123454A0 (en) | 1998-09-24 |
| ATE286039T1 (de) | 2005-01-15 |
| CN1110490C (zh) | 2003-06-04 |
| HU9800395D0 (en) | 1998-04-28 |
| CA2230349A1 (en) | 1998-08-26 |
| NZ329838A (en) | 1999-07-29 |
| AU5633398A (en) | 1998-09-03 |
| JP4171097B2 (ja) | 2008-10-22 |
| PL325045A1 (en) | 1998-08-31 |
| HUP9800395A2 (hu) | 2001-04-28 |
| DE59812423D1 (de) | 2005-02-03 |
| AU737461B2 (en) | 2001-08-23 |
| ID19931A (id) | 1998-08-27 |
| CZ53998A3 (cs) | 1998-09-16 |
| HUP9800395A3 (en) | 2002-04-29 |
| SK23998A3 (en) | 1998-09-09 |
| CN1193017A (zh) | 1998-09-16 |
| RU2223264C2 (ru) | 2004-02-10 |
| JPH10287641A (ja) | 1998-10-27 |
| TR199800301A2 (xx) | 1998-09-21 |
| KR19980071625A (ko) | 1998-10-26 |
| EP0861836B1 (de) | 2004-12-29 |
| AR011163A1 (es) | 2000-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODBC | Application rejected |