HRP980528A2 - Sulfonamid-substituted chromanes, process for their preparation, their use as medicaments, and pharmaceutical preparations containing them - Google Patents
Sulfonamid-substituted chromanes, process for their preparation, their use as medicaments, and pharmaceutical preparations containing themInfo
- Publication number
- HRP980528A2 HRP980528A2 HR19742508.9A HRP980528A HRP980528A2 HR P980528 A2 HRP980528 A2 HR P980528A2 HR P980528 A HRP980528 A HR P980528A HR P980528 A2 HRP980528 A2 HR P980528A2
- Authority
- HR
- Croatia
- Prior art keywords
- hydrogen
- atoms
- methyl
- group
- ethyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 29
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title description 40
- 238000002360 preparation method Methods 0.000 title description 8
- 230000008569 process Effects 0.000 title description 6
- 150000001843 chromanes Chemical class 0.000 title description 2
- 239000001257 hydrogen Substances 0.000 claims description 150
- 229910052739 hydrogen Inorganic materials 0.000 claims description 150
- 125000004432 carbon atom Chemical group C* 0.000 claims description 140
- -1 methoxy, dimethylamino, sulfamoyl Chemical group 0.000 claims description 124
- 150000001875 compounds Chemical class 0.000 claims description 117
- 150000002431 hydrogen Chemical class 0.000 claims description 97
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 125000000623 heterocyclic group Chemical group 0.000 claims description 70
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 50
- 229910052801 chlorine Inorganic materials 0.000 claims description 49
- 229910052794 bromium Inorganic materials 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 46
- 229910052731 fluorine Inorganic materials 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 39
- 125000001544 thienyl group Chemical group 0.000 claims description 34
- 239000000126 substance Substances 0.000 claims description 24
- 238000011321 prophylaxis Methods 0.000 claims description 21
- 229940079593 drug Drugs 0.000 claims description 20
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000002541 furyl group Chemical group 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 claims description 16
- 238000002560 therapeutic procedure Methods 0.000 claims description 16
- 239000013543 active substance Substances 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 206010003119 arrhythmia Diseases 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 230000006793 arrhythmia Effects 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 206010003662 Atrial flutter Diseases 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 230000028327 secretion Effects 0.000 claims description 4
- 231100000397 ulcer Toxicity 0.000 claims description 4
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 3
- 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
- 230000001746 atrial effect Effects 0.000 claims description 3
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 230000000968 intestinal effect Effects 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 208000000689 peptic esophagitis Diseases 0.000 claims description 3
- 230000033764 rhythmic process Effects 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 230000002861 ventricular Effects 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 230000002496 gastric effect Effects 0.000 claims 2
- 208000003663 ventricular fibrillation Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
- 238000002844 melting Methods 0.000 description 35
- 230000008018 melting Effects 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000000460 chlorine Substances 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000003208 petroleum Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000002585 base Substances 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 230000009471 action Effects 0.000 description 15
- 229940124530 sulfonamide Drugs 0.000 description 15
- 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 14
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 14
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- 150000003456 sulfonamides Chemical class 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005804 alkylation reaction Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 210000000287 oocyte Anatomy 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UAXWPLCLDSMHRF-UHFFFAOYSA-N 6-hydroxy-2,2-dimethyl-3h-chromen-4-one Chemical compound OC1=CC=C2OC(C)(C)CC(=O)C2=C1 UAXWPLCLDSMHRF-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- ICXNHPVYFIDZLM-UHFFFAOYSA-N n-(6-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-(2-methoxyethyl)methanesulfonamide Chemical compound C1=C(O)C=C2C(N(CCOC)S(C)(=O)=O)CC(C)(C)OC2=C1 ICXNHPVYFIDZLM-UHFFFAOYSA-N 0.000 description 6
- OFIYHCBSSMCXCP-UHFFFAOYSA-N n-ethyl-n-(6-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)methanesulfonamide Chemical compound C1=C(O)C=C2C(N(CC)S(C)(=O)=O)CC(C)(C)OC2=C1 OFIYHCBSSMCXCP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 230000003213 activating effect Effects 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- 238000007112 amidation reaction Methods 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000012262 resinous product Substances 0.000 description 5
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-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
- 241000700199 Cavia porcellus Species 0.000 description 4
- 108091006146 Channels Proteins 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 241000269370 Xenopus <genus> Species 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 230000009435 amidation Effects 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 229940082627 class iii antiarrhythmics Drugs 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- FWAJYAMELADUBX-UHFFFAOYSA-N n-(6-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-methylethanesulfonamide Chemical compound C1=C(O)C=C2C(N(C)S(=O)(=O)CC)CC(C)(C)OC2=C1 FWAJYAMELADUBX-UHFFFAOYSA-N 0.000 description 4
- JOCBJLUTRVFIDZ-UHFFFAOYSA-N n-(6-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-propylethanesulfonamide Chemical compound C1=C(O)C=C2C(N(CCC)S(=O)(=O)CC)CC(C)(C)OC2=C1 JOCBJLUTRVFIDZ-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 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
- JOZWPJGRGUOZGY-UHFFFAOYSA-N 1-bromo-3-ethoxypropane Chemical compound CCOCCCBr JOZWPJGRGUOZGY-UHFFFAOYSA-N 0.000 description 3
- APPZTNAPKBNODA-UHFFFAOYSA-N 2,2-dimethyl-6-phenylmethoxy-3,4-dihydrochromen-4-amine Chemical compound C=1C=C2OC(C)(C)CC(N)C2=CC=1OCC1=CC=CC=C1 APPZTNAPKBNODA-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 210000004413 cardiac myocyte Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 210000001072 colon Anatomy 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000005595 deprotonation Effects 0.000 description 3
- 238000010537 deprotonation reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- FECOFNLZPVRHCX-UHFFFAOYSA-N ethyl 4-[[4-[2-methoxyethyl(methylsulfonyl)amino]-2,2-dimethyl-3,4-dihydrochromen-6-yl]oxy]butanoate Chemical compound O1C(C)(C)CC(N(CCOC)S(C)(=O)=O)C2=CC(OCCCC(=O)OCC)=CC=C21 FECOFNLZPVRHCX-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- YJZDSGSPTJUALV-UHFFFAOYSA-N n-(6-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-methylmethanesulfonamide Chemical compound C1=C(O)C=C2C(N(C)S(C)(=O)=O)CC(C)(C)OC2=C1 YJZDSGSPTJUALV-UHFFFAOYSA-N 0.000 description 3
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 210000002460 smooth muscle Anatomy 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- YKURFHOYVQJKSA-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydrochromen-3-amine Chemical compound C1=CC=C2CC(N)C(C)(C)OC2=C1 YKURFHOYVQJKSA-UHFFFAOYSA-N 0.000 description 2
- MITIYLBEZOKYLX-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydrochromene Chemical compound C1=CC=C2OC(C)(C)CCC2=C1 MITIYLBEZOKYLX-UHFFFAOYSA-N 0.000 description 2
- XWROIWDXQLSBBR-UHFFFAOYSA-N 2,2-dimethyl-6-phenylmethoxy-3h-chromen-4-one Chemical compound C=1C=C2OC(C)(C)CC(=O)C2=CC=1OCC1=CC=CC=C1 XWROIWDXQLSBBR-UHFFFAOYSA-N 0.000 description 2
- SEBPXHSZHLFWRL-UHFFFAOYSA-N 3,4-dihydro-2,2,5,7,8-pentamethyl-2h-1-benzopyran-6-ol Chemical compound O1C(C)(C)CCC2=C1C(C)=C(C)C(O)=C2C SEBPXHSZHLFWRL-UHFFFAOYSA-N 0.000 description 2
- HBLDKCGIBIGVPC-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-3-ol Chemical class C1=CC=C2CC(O)COC2=C1 HBLDKCGIBIGVPC-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-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
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
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- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000009090 positive inotropic effect Effects 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
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000001536 pro-arrhythmogenic effect Effects 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
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
- 229960003401 ramipril Drugs 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000002336 repolarization Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000000050 smooth muscle relaxant Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 150000003413 spiro compounds Chemical class 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
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742508A DE19742508A1 (de) | 1997-09-26 | 1997-09-26 | Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980528A2 true HRP980528A2 (en) | 1999-06-30 |
Family
ID=7843708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR19742508.9A HRP980528A2 (en) | 1997-09-26 | 1998-09-25 | Sulfonamid-substituted chromanes, process for their preparation, their use as medicaments, and pharmaceutical preparations containing them |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6177449B1 (zh) |
| EP (1) | EP0906911B1 (zh) |
| JP (1) | JP4422222B2 (zh) |
| KR (1) | KR19990030120A (zh) |
| CN (1) | CN1216763A (zh) |
| AR (1) | AR014915A1 (zh) |
| AT (1) | ATE265445T1 (zh) |
| AU (1) | AU755735B2 (zh) |
| BR (1) | BR9803367A (zh) |
| CA (1) | CA2248300C (zh) |
| CZ (1) | CZ307198A3 (zh) |
| DE (2) | DE19742508A1 (zh) |
| ES (1) | ES2221107T3 (zh) |
| HR (1) | HRP980528A2 (zh) |
| HU (1) | HUP9802155A3 (zh) |
| ID (1) | ID20967A (zh) |
| IL (1) | IL126280A (zh) |
| NO (1) | NO984476L (zh) |
| NZ (1) | NZ332030A (zh) |
| PL (1) | PL328854A1 (zh) |
| RU (1) | RU2220965C2 (zh) |
| SK (1) | SK131898A3 (zh) |
| TR (1) | TR199801903A2 (zh) |
| TW (1) | TW565559B (zh) |
| ZA (1) | ZA988788B (zh) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19748469A1 (de) * | 1997-11-03 | 1999-05-06 | Hoechst Marion Roussel De Gmbh | Sulfonamid-substituierte Benzopyranderivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| 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 |
| TW589305B (en) | 2001-02-14 | 2004-06-01 | Nissan Chemical Ind Ltd | 4-aminobenzopyran derivatives |
| FI20011507A0 (fi) * | 2001-07-10 | 2001-07-10 | Orion Corp | Uusia yhdisteitä |
| US7001660B2 (en) * | 2001-07-16 | 2006-02-21 | Gilbert Garitano | Images in solids surfaces |
| FI20030030A0 (fi) * | 2003-01-09 | 2003-01-09 | Orion Corp | Uusia yhdisteitä |
| US7368582B2 (en) | 2003-10-17 | 2008-05-06 | Solvay Pharmaceuticals Gmbh | Amidomethyl-substituted 2-(4-sulfonylamino)-3-hydroxy-3,4-dihydro-2H-chromen-6-yl compounds, a process and intermediates for their production, and pharmaceutical compositions containing them |
| MY147767A (en) * | 2004-06-16 | 2013-01-31 | Janssen Pharmaceutica Nv | Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders |
| EP1871758B1 (en) * | 2005-04-12 | 2010-08-25 | Abbott Products GmbH | Aminoalkyl-amidomethyl-substituted 2- (4-sulphonylamino) -3-hydroxy-3 , 4-dihydro-2h-cromen-6-yl derivatives and their use as potassium channel blockers |
| US7714150B2 (en) | 2005-04-12 | 2010-05-11 | Solvay Pharmaceuticals Gmbh | Aminoalkyl-amidomethyl-substituted 2-(4-sulphonylamino)-3-hydroxy-3,4-dihydro-2H-chroman-6-yl derivatives |
| TW201022223A (en) * | 2008-08-14 | 2010-06-16 | Nissan Chemical Ind Ltd | Di-substituted benzopyrane compound |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820834A (en) | 1984-06-26 | 1989-04-11 | Merck & Co., Inc. | Benzodiazepine analogs |
| FR2639349B1 (fr) | 1988-11-23 | 1991-02-22 | Sanofi Sa | Nouveaux derives du chromane actifs sur le systeme nerveux central, leur procede de preparation et les compositions pharmaceutiques en contenant |
| US5104890A (en) * | 1989-03-28 | 1992-04-14 | Fujisawa Pharmaceutical Company, Ltd. | Benzopyran derivatives and processes for preparation thereof |
| US5428031A (en) | 1991-12-03 | 1995-06-27 | Merck & Co., Inc. | Methods of treating cardiac arrhythmia |
| AU711986B2 (en) * | 1996-05-15 | 1999-10-28 | Hoechst Aktiengesellschaft | Sulfonamide-substituted chromans, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them |
| DE19706675A1 (de) * | 1997-02-20 | 1998-08-27 | Hoechst Ag | Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19742509A1 (de) * | 1997-09-26 | 1999-04-01 | Hoechst Marion Roussel De Gmbh | Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
-
1997
- 1997-09-26 DE DE19742508A patent/DE19742508A1/de not_active Withdrawn
-
1998
- 1998-09-17 IL IL12628098A patent/IL126280A/xx not_active IP Right Cessation
- 1998-09-19 ES ES98117810T patent/ES2221107T3/es not_active Expired - Lifetime
- 1998-09-19 AT AT98117810T patent/ATE265445T1/de not_active IP Right Cessation
- 1998-09-19 EP EP98117810A patent/EP0906911B1/de not_active Expired - Lifetime
- 1998-09-19 DE DE59811267T patent/DE59811267D1/de not_active Expired - Lifetime
- 1998-09-22 CA CA002248300A patent/CA2248300C/en not_active Expired - Fee Related
- 1998-09-22 CN CN98119539A patent/CN1216763A/zh active Pending
- 1998-09-24 AR ARP980104775A patent/AR014915A1/es not_active Application Discontinuation
- 1998-09-24 CZ CZ983071A patent/CZ307198A3/cs unknown
- 1998-09-24 RU RU98117567/04A patent/RU2220965C2/ru not_active IP Right Cessation
- 1998-09-24 ID IDP981279A patent/ID20967A/id unknown
- 1998-09-24 SK SK1318-98A patent/SK131898A3/sk unknown
- 1998-09-24 TR TR1998/01903A patent/TR199801903A2/xx unknown
- 1998-09-24 NZ NZ332030A patent/NZ332030A/xx unknown
- 1998-09-25 JP JP27216898A patent/JP4422222B2/ja not_active Expired - Fee Related
- 1998-09-25 AU AU87082/98A patent/AU755735B2/en not_active Ceased
- 1998-09-25 NO NO984476A patent/NO984476L/no not_active Application Discontinuation
- 1998-09-25 PL PL98328854A patent/PL328854A1/xx unknown
- 1998-09-25 KR KR1019980039836A patent/KR19990030120A/ko not_active Application Discontinuation
- 1998-09-25 HR HR19742508.9A patent/HRP980528A2/hr not_active Application Discontinuation
- 1998-09-25 HU HU9802155A patent/HUP9802155A3/hu unknown
- 1998-09-25 ZA ZA988788A patent/ZA988788B/xx unknown
- 1998-09-25 BR BR9803367-0A patent/BR9803367A/pt not_active IP Right Cessation
- 1998-10-22 TW TW087115865A patent/TW565559B/zh active
-
1999
- 1999-10-20 US US09/421,277 patent/US6177449B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| TR199801903A3 (tr) | 1999-04-21 |
| KR19990030120A (ko) | 1999-04-26 |
| ID20967A (id) | 1999-04-01 |
| CA2248300A1 (en) | 1999-03-26 |
| JPH11158171A (ja) | 1999-06-15 |
| RU2220965C2 (ru) | 2004-01-10 |
| HUP9802155A2 (hu) | 1999-09-28 |
| AU755735B2 (en) | 2002-12-19 |
| US6177449B1 (en) | 2001-01-23 |
| BR9803367A (pt) | 2000-05-09 |
| TR199801903A2 (xx) | 1999-04-21 |
| TW565559B (en) | 2003-12-11 |
| AU8708298A (en) | 1999-04-15 |
| EP0906911A1 (de) | 1999-04-07 |
| SK131898A3 (en) | 1999-06-11 |
| CA2248300C (en) | 2008-12-02 |
| DE59811267D1 (de) | 2004-06-03 |
| NZ332030A (en) | 2000-04-28 |
| HUP9802155A3 (en) | 2002-04-29 |
| NO984476D0 (no) | 1998-09-25 |
| CN1216763A (zh) | 1999-05-19 |
| ZA988788B (en) | 1999-03-26 |
| NO984476L (no) | 1999-03-29 |
| HU9802155D0 (en) | 1998-11-30 |
| DE19742508A1 (de) | 1999-04-01 |
| ATE265445T1 (de) | 2004-05-15 |
| AR014915A1 (es) | 2001-04-11 |
| PL328854A1 (en) | 1999-03-29 |
| CZ307198A3 (cs) | 1999-04-14 |
| IL126280A0 (en) | 1999-05-09 |
| EP0906911B1 (de) | 2004-04-28 |
| IL126280A (en) | 2003-10-31 |
| ES2221107T3 (es) | 2004-12-16 |
| JP4422222B2 (ja) | 2010-02-24 |
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