CA1291165C - Alkylsulfonamidophenylalkylamines - Google Patents
AlkylsulfonamidophenylalkylaminesInfo
- Publication number
- CA1291165C CA1291165C CA000493000A CA493000A CA1291165C CA 1291165 C CA1291165 C CA 1291165C CA 000493000 A CA000493000 A CA 000493000A CA 493000 A CA493000 A CA 493000A CA 1291165 C CA1291165 C CA 1291165C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- phenyl
- butyl
- ethyl
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- DOAVYLWNNKCAPE-UHFFFAOYSA-N n-[4-[4-[ethyl(heptyl)amino]butyl]phenyl]methanesulfonamide Chemical compound CCCCCCCN(CC)CCCCC1=CC=C(NS(C)(=O)=O)C=C1 DOAVYLWNNKCAPE-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- OHQPVBCPZDSVEO-UHFFFAOYSA-N 4-[4-[ethyl(heptyl)amino]butyl]aniline Chemical compound CCCCCCCN(CC)CCCCC1=CC=C(N)C=C1 OHQPVBCPZDSVEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- IYGHRZKVMZBESY-UHFFFAOYSA-N n-[4-[4-[ethyl(heptyl)amino]butyl]phenyl]methanesulfonamide;hydrochloride Chemical compound Cl.CCCCCCCN(CC)CCCCC1=CC=C(NS(C)(=O)=O)C=C1 IYGHRZKVMZBESY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract description 7
- 230000003389 potentiating effect Effects 0.000 abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 40
- 239000000203 mixture Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 23
- -1 phenylalkyl quaternary ammonium salts Chemical class 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000463 material Substances 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 14
- 239000000284 extract Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 206010003119 arrhythmia Diseases 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000006793 arrhythmia Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229920002472 Starch Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 235000019698 starch Nutrition 0.000 description 8
- WPSYTTKBGAZSCX-UHFFFAOYSA-N Clofilium Chemical compound CCCCCCC[N+](CC)(CC)CCCCC1=CC=C(Cl)C=C1 WPSYTTKBGAZSCX-UHFFFAOYSA-N 0.000 description 7
- 241000124008 Mammalia Species 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000036982 action potential Effects 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 239000003039 volatile agent Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000005422 alkyl sulfonamido group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 description 4
- 230000001746 atrial effect Effects 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 208000003663 ventricular fibrillation Diseases 0.000 description 4
- YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 description 3
- JEGLXZHTUFJVAI-UHFFFAOYSA-N 4-[4-[butyl(heptyl)amino]butyl]aniline Chemical compound CCCCCCCN(CCCC)CCCCC1=CC=C(N)C=C1 JEGLXZHTUFJVAI-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
- 239000005711 Benzoic acid Substances 0.000 description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 3
- 208000001871 Tachycardia Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 210000005003 heart tissue Anatomy 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 description 3
- XSPMQFCWWFJNPX-UHFFFAOYSA-N n-ethyl-n-heptyl-4-(4-nitrophenyl)butanamide Chemical compound CCCCCCCN(CC)C(=O)CCCC1=CC=C([N+]([O-])=O)C=C1 XSPMQFCWWFJNPX-UHFFFAOYSA-N 0.000 description 3
- 125000006501 nitrophenyl group Chemical group 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 230000002336 repolarization Effects 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 230000002861 ventricular Effects 0.000 description 3
- KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 2
- KDVYUJWTHVXKRG-UHFFFAOYSA-N C(C(=O)O)(=O)O.C(C)N(CCCCC1=CC=C(C=C1)NS(=O)(=O)C)CCCCCCC Chemical compound C(C(=O)O)(=O)O.C(C)N(CCCCC1=CC=C(C=C1)NS(=O)(=O)C)CCCCCCC KDVYUJWTHVXKRG-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000011833 dog model Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000037024 effective refractory period Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 2
- 239000011491 glass wool Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- MUDZMUDNRIHODX-UHFFFAOYSA-N n-[3-[4-[ethyl(heptyl)amino]butyl]phenyl]methanesulfonamide Chemical compound CCCCCCCN(CC)CCCCC1=CC=CC(NS(C)(=O)=O)=C1 MUDZMUDNRIHODX-UHFFFAOYSA-N 0.000 description 2
- VCOVYGJLHFVYEY-UHFFFAOYSA-N n-[4-[3-(dimethylamino)propyl]phenyl]methanesulfonamide Chemical compound CN(C)CCCC1=CC=C(NS(C)(=O)=O)C=C1 VCOVYGJLHFVYEY-UHFFFAOYSA-N 0.000 description 2
- TWCDOODKCFIINW-UHFFFAOYSA-N n-[4-[4-[butyl(heptyl)amino]butyl]phenyl]methanesulfonamide Chemical compound CCCCCCCN(CCCC)CCCCC1=CC=C(NS(C)(=O)=O)C=C1 TWCDOODKCFIINW-UHFFFAOYSA-N 0.000 description 2
- IKMSUNQJSUPFEZ-UHFFFAOYSA-N n-[4-[4-[ethyl(heptyl)amino]butyl]phenyl]methanesulfonamide;hydrobromide Chemical compound Br.CCCCCCCN(CC)CCCCC1=CC=C(NS(C)(=O)=O)C=C1 IKMSUNQJSUPFEZ-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- NTURQZFFJDCTMZ-UHFFFAOYSA-N 1-(2-bromoethyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CCBr)C=C1 NTURQZFFJDCTMZ-UHFFFAOYSA-N 0.000 description 1
- AUVALWUPUHHNQV-UHFFFAOYSA-N 2-hydroxy-3-propylbenzoic acid Chemical class CCCC1=CC=CC(C(O)=O)=C1O AUVALWUPUHHNQV-UHFFFAOYSA-N 0.000 description 1
- JLHCINAXHMPNIO-UHFFFAOYSA-N 3-[4-(ethylsulfonylamino)phenyl]propanoyl chloride Chemical compound CCS(=O)(=O)NC1=CC=C(CCC(Cl)=O)C=C1 JLHCINAXHMPNIO-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SLOWBFFBASJEAL-UHFFFAOYSA-K 4-(4-chlorophenyl)butyl-diethyl-heptylazanium;phosphate Chemical compound [O-]P([O-])([O-])=O.CCCCCCC[N+](CC)(CC)CCCCC1=CC=C(Cl)C=C1.CCCCCCC[N+](CC)(CC)CCCCC1=CC=C(Cl)C=C1.CCCCCCC[N+](CC)(CC)CCCCC1=CC=C(Cl)C=C1 SLOWBFFBASJEAL-UHFFFAOYSA-K 0.000 description 1
- QPHLFSGMBIJFRA-UHFFFAOYSA-N 4-(4-nitrophenyl)butan-1-amine Chemical compound NCCCCC1=CC=C([N+]([O-])=O)C=C1 QPHLFSGMBIJFRA-UHFFFAOYSA-N 0.000 description 1
- WQMLUHZFRFCQDB-UHFFFAOYSA-N 4-(4-nitrophenyl)butyric acid Chemical compound OC(=O)CCCC1=CC=C([N+]([O-])=O)C=C1 WQMLUHZFRFCQDB-UHFFFAOYSA-N 0.000 description 1
- HXHGULXINZUGJX-UHFFFAOYSA-N 4-chlorobutanol Chemical compound OCCCCCl HXHGULXINZUGJX-UHFFFAOYSA-N 0.000 description 1
- MUGBWUBMQSQNAC-UHFFFAOYSA-N 5-(4-nitrophenyl)pentan-2-one Chemical compound CC(=O)CCCC1=CC=C([N+]([O-])=O)C=C1 MUGBWUBMQSQNAC-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010003130 Arrhythmia supraventricular Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- 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
- 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
-
- 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
- C07C311/08—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 six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Engineering & Computer Science (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/660,816 US4569801A (en) | 1984-10-15 | 1984-10-15 | Alkylsulfonamidophenylalkylamines |
| US660,816 | 1984-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1291165C true CA1291165C (en) | 1991-10-22 |
Family
ID=24651088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000493000A Expired - Lifetime CA1291165C (en) | 1984-10-15 | 1985-10-15 | Alkylsulfonamidophenylalkylamines |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4569801A (enExample) |
| EP (1) | EP0178874B1 (enExample) |
| JP (1) | JPS6197256A (enExample) |
| KR (1) | KR880001008B1 (enExample) |
| CN (1) | CN1004133B (enExample) |
| AR (1) | AR241528A1 (enExample) |
| AT (1) | ATE41922T1 (enExample) |
| AU (1) | AU586644B2 (enExample) |
| CA (1) | CA1291165C (enExample) |
| DK (1) | DK164450C (enExample) |
| ES (1) | ES8609229A1 (enExample) |
| GR (1) | GR852496B (enExample) |
| HU (1) | HU195479B (enExample) |
| IL (1) | IL76707A0 (enExample) |
| NZ (1) | NZ213812A (enExample) |
| PT (1) | PT81299B (enExample) |
| SU (1) | SU1424730A3 (enExample) |
| ZA (1) | ZA857871B (enExample) |
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|---|---|---|---|---|
| US5155268A (en) * | 1984-05-04 | 1992-10-13 | The Upjohn Company | Antiarrhythmic N-aminoalkylene alkyl and aryl sulfonamides |
| GB8609630D0 (en) * | 1986-04-19 | 1986-05-21 | Pfizer Ltd | Anti-arrhythmia agents |
| EG18188A (en) * | 1986-05-01 | 1992-09-30 | Pfizer Ltd | Process for preparation anti-arhythmia agents |
| GB8706662D0 (en) * | 1987-03-20 | 1987-04-23 | Pfizer Ltd | Anti-arrhythmia agents |
| DE3732094A1 (de) * | 1987-09-24 | 1989-04-06 | Basf Ag | Bispidinderivate als klasse iii-antiarrhythmika |
| US4906634A (en) * | 1988-03-08 | 1990-03-06 | Schering A.G. | Novel N-[4-(aminosubstituted)phenyl]methanesulfonamides and their use as cardiovascular agents |
| US5238959A (en) * | 1988-04-08 | 1993-08-24 | Eli Lilly And Company | 3-phenyloxy-3-phenyl propanamines |
| CA1337128C (en) * | 1988-04-08 | 1995-09-26 | David Wayne Robertson | Propanamine derivatives |
| US5405997A (en) * | 1989-07-25 | 1995-04-11 | The Upjohn Company | Antiarrhythmic methanesulfonamides |
| JPH10505829A (ja) * | 1994-09-12 | 1998-06-09 | ファルマシア・アンド・アップジョン・カンパニー | 抗不整脈活性を有する４−（４−メタンスルホンアミドフェニル）ブチルアミン誘導体 |
| US5874475A (en) * | 1995-12-21 | 1999-02-23 | Pharmacia & Upjohn Company | Antiarrhythmic (S)-enantiomers of methanesulfonamides |
| US6012457A (en) * | 1997-07-08 | 2000-01-11 | The Regents Of The University Of California | Device and method for forming a circumferential conduction block in a pulmonary vein |
| US5971983A (en) | 1997-05-09 | 1999-10-26 | The Regents Of The University Of California | Tissue ablation device and method of use |
| US6024740A (en) | 1997-07-08 | 2000-02-15 | The Regents Of The University Of California | Circumferential ablation device assembly |
| US6245064B1 (en) | 1997-07-08 | 2001-06-12 | Atrionix, Inc. | Circumferential ablation device assembly |
| US6164283A (en) * | 1997-07-08 | 2000-12-26 | The Regents Of The University Of California | Device and method for forming a circumferential conduction block in a pulmonary vein |
| US6514249B1 (en) | 1997-07-08 | 2003-02-04 | Atrionix, Inc. | Positioning system and method for orienting an ablation element within a pulmonary vein ostium |
| US6652515B1 (en) | 1997-07-08 | 2003-11-25 | Atrionix, Inc. | Tissue ablation device assembly and method for electrically isolating a pulmonary vein ostium from an atrial wall |
| US6966908B2 (en) | 1997-07-08 | 2005-11-22 | Atrionix, Inc. | Tissue ablation device assembly and method for electrically isolating a pulmonary vein ostium from an atrial wall |
| US6869431B2 (en) | 1997-07-08 | 2005-03-22 | Atrionix, Inc. | Medical device with sensor cooperating with expandable member |
| US6500174B1 (en) | 1997-07-08 | 2002-12-31 | Atrionix, Inc. | Circumferential ablation device assembly and methods of use and manufacture providing an ablative circumferential band along an expandable member |
| US6997925B2 (en) * | 1997-07-08 | 2006-02-14 | Atrionx, Inc. | Tissue ablation device assembly and method for electrically isolating a pulmonary vein ostium from an atrial wall |
| WO2000010557A1 (fr) * | 1998-08-25 | 2000-03-02 | Nippon Shinyaku Co.,Ltd. | Preparations solides stabilisees |
| US6607502B1 (en) | 1998-11-25 | 2003-08-19 | Atrionix, Inc. | Apparatus and method incorporating an ultrasound transducer onto a delivery member |
| US6758830B1 (en) | 1999-05-11 | 2004-07-06 | Atrionix, Inc. | Catheter positioning system |
| EP2289448B1 (en) | 1999-05-11 | 2013-03-13 | Atrionix, Inc. | Tissue ablation system including a balloon anchor wire |
| AU6321301A (en) * | 2000-05-16 | 2001-11-26 | Atrionix Inc | Apparatus and method incorporating an ultrasound transducer onto a delivery member |
| AU6682401A (en) | 2000-06-13 | 2001-12-24 | Atrionix Inc | Surgical ablation probe for forming a circumferential lesion |
| CA2391051C (en) | 2000-09-08 | 2011-07-12 | Atrionix, Inc. | Medical device with sensor cooperating with expandable member |
| US6755822B2 (en) | 2001-06-01 | 2004-06-29 | Cryocor, Inc. | Device and method for the creation of a circumferential cryogenic lesion in a pulmonary vein |
| US6932804B2 (en) | 2003-01-21 | 2005-08-23 | The Regents Of The University Of California | System and method for forming a non-ablative cardiac conduction block |
| WO2003095016A1 (en) * | 2002-05-08 | 2003-11-20 | The Regents Of The University Of California | System and method for forming a non-ablative cardiac conduction block |
| US20040106896A1 (en) * | 2002-11-29 | 2004-06-03 | The Regents Of The University Of California | System and method for forming a non-ablative cardiac conduction block |
| US6786202B2 (en) * | 2002-09-24 | 2004-09-07 | Caterpillar Inc | Hydraulic pump circuit |
| US7317950B2 (en) * | 2002-11-16 | 2008-01-08 | The Regents Of The University Of California | Cardiac stimulation system with delivery of conductive agent |
| US7670335B2 (en) | 2003-07-21 | 2010-03-02 | Biosense Webster, Inc. | Ablation device with spiral array ultrasound transducer |
| US7247269B2 (en) * | 2003-07-21 | 2007-07-24 | Biosense Webster, Inc. | Method for making a spiral array ultrasound transducer |
| MXPA06007624A (es) * | 2003-12-31 | 2007-01-30 | Johnson & Johnson | Montaje de dispositivo de ablacion circunferencial con dos miembros expansibles. |
| US8932208B2 (en) * | 2005-05-26 | 2015-01-13 | Maquet Cardiovascular Llc | Apparatus and methods for performing minimally-invasive surgical procedures |
| US20060270900A1 (en) * | 2005-05-26 | 2006-11-30 | Chin Albert K | Apparatus and methods for performing ablation |
| US20070185479A1 (en) * | 2006-02-06 | 2007-08-09 | Liming Lau | Methods and devices for performing ablation and assessing efficacy thereof |
| US20070225697A1 (en) * | 2006-03-23 | 2007-09-27 | Ketan Shroff | Apparatus and methods for cardiac ablation |
| US20080039879A1 (en) * | 2006-08-09 | 2008-02-14 | Chin Albert K | Devices and methods for atrial appendage exclusion |
| US8728073B2 (en) | 2006-10-10 | 2014-05-20 | Biosense Webster, Inc. | Multi-region staged inflation balloon |
| US8512387B2 (en) * | 2007-09-07 | 2013-08-20 | Robert S. Fishel | Esophageal cooling system for ablation procedures associated with cardiac arrhythmias |
| WO2009045265A1 (en) | 2007-10-05 | 2009-04-09 | Maquet Cardiovascular, Llc | Devices and methods for minimally-invasive surgical procedures |
| US20090209986A1 (en) * | 2008-02-15 | 2009-08-20 | Stewart Michael C | Devices, Tools and Methods for Atrial Appendage Exclusion |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR152F (enExample) * | 1962-01-24 | |||
| US3574741A (en) * | 1969-04-14 | 1971-04-13 | Mead Johnson & Co | Sulfonamidophenalkylamines |
| HU173192B (hu) * | 1973-08-13 | 1979-03-28 | Fujisawa Pharmaceutical Co | Sposob poluchenija novykh proizvodnykh fenilglicina |
| US4277501A (en) * | 1977-12-19 | 1981-07-07 | Eli Lilly And Company | Para-nitrophenylalkylamines and pharmaceutical compositions |
| US4289787A (en) * | 1977-12-19 | 1981-09-15 | Eli Lilly And Company | Quaternary ammonium antiarrhythmic drugs |
| CA1120058A (en) * | 1978-07-03 | 1982-03-16 | Jack Mills | Phenethanolamines, formulations and potentiation of oncolytic drugs |
| US4336269A (en) * | 1979-12-10 | 1982-06-22 | Eli Lilly And Company | Para-nitrophenylalkylamines |
| EP0164865B1 (en) * | 1984-05-04 | 1988-12-21 | The Upjohn Company | N-(aminoalkylphenyl)sulfonamides their preparation and therapeutic use |
-
1984
- 1984-10-15 US US06/660,816 patent/US4569801A/en not_active Expired - Fee Related
-
1985
- 1985-10-14 EP EP85307338A patent/EP0178874B1/en not_active Expired
- 1985-10-14 CN CN85107020.5A patent/CN1004133B/zh not_active Expired
- 1985-10-14 ES ES547840A patent/ES8609229A1/es not_active Expired
- 1985-10-14 HU HU853969A patent/HU195479B/hu not_active IP Right Cessation
- 1985-10-14 AU AU48558/85A patent/AU586644B2/en not_active Ceased
- 1985-10-14 ZA ZA857871A patent/ZA857871B/xx unknown
- 1985-10-14 DK DK468185A patent/DK164450C/da not_active IP Right Cessation
- 1985-10-14 NZ NZ213812A patent/NZ213812A/xx unknown
- 1985-10-14 PT PT81299A patent/PT81299B/pt not_active IP Right Cessation
- 1985-10-14 AT AT85307338T patent/ATE41922T1/de not_active IP Right Cessation
- 1985-10-14 AR AR85301936A patent/AR241528A1/es active
- 1985-10-14 KR KR1019850007530A patent/KR880001008B1/ko not_active Expired
- 1985-10-14 SU SU853961255A patent/SU1424730A3/ru active
- 1985-10-14 IL IL76707A patent/IL76707A0/xx not_active IP Right Cessation
- 1985-10-15 GR GR852496A patent/GR852496B/el unknown
- 1985-10-15 CA CA000493000A patent/CA1291165C/en not_active Expired - Lifetime
- 1985-10-15 JP JP60230895A patent/JPS6197256A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0178874A1 (en) | 1986-04-23 |
| AU586644B2 (en) | 1989-07-20 |
| EP0178874B1 (en) | 1989-04-05 |
| IL76707A0 (en) | 1986-02-28 |
| AU4855885A (en) | 1986-04-24 |
| CN1004133B (zh) | 1989-05-10 |
| NZ213812A (en) | 1989-01-06 |
| KR860003210A (ko) | 1986-05-21 |
| ZA857871B (en) | 1987-05-27 |
| DK164450B (da) | 1992-06-29 |
| ES547840A0 (es) | 1986-09-01 |
| GR852496B (enExample) | 1986-02-18 |
| AR241528A1 (es) | 1992-08-31 |
| JPS6197256A (ja) | 1986-05-15 |
| KR880001008B1 (ko) | 1988-06-13 |
| CN85107020A (zh) | 1986-04-10 |
| HU195479B (en) | 1988-05-30 |
| HUT38610A (en) | 1986-06-30 |
| PT81299B (pt) | 1988-02-17 |
| DK468185A (da) | 1986-04-16 |
| DK164450C (da) | 1992-11-16 |
| ATE41922T1 (de) | 1989-04-15 |
| US4569801A (en) | 1986-02-11 |
| PT81299A (en) | 1985-11-01 |
| SU1424730A3 (ru) | 1988-09-15 |
| ES8609229A1 (es) | 1986-09-01 |
| DK468185D0 (da) | 1985-10-14 |
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| MKLA | Lapsed |