UA75412C2 - Anthranilic acid amides with heteroarylsulfonyl lateral chain, their use as medical and diagnostic agent and pharmaceutical composition containing them - Google Patents

Anthranilic acid amides with heteroarylsulfonyl lateral chain, their use as medical and diagnostic agent and pharmaceutical composition containing them Download PDF

Info

Publication number: UA75412C2
Authority: UA; Ukraine
Prior art keywords: group; carbon atoms; alkyl; heteroaryl; phenyl
Prior art date: 2001-06-12

Application number

UA2004010206A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Sanofi Aventis Deutschland

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-06-12

Filing date

2002-05-31

Publication date

2006-04-17

2002-05-31 Application filed by Sanofi Aventis Deutschland filed Critical Sanofi Aventis Deutschland

2006-04-17 Publication of UA75412C2 publication Critical patent/UA75412C2/uk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 7
PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title description 4
229940039227 diagnostic agent Drugs 0.000 title 1
239000000032 diagnostic agent Substances 0.000 title 1
125000005143 heteroarylsulfonyl group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 94
238000011282 treatment Methods 0.000 claims abstract description 14
206010003658 Atrial Fibrillation Diseases 0.000 claims abstract description 9
239000013543 active substance Substances 0.000 claims abstract description 8
206010003662 Atrial flutter Diseases 0.000 claims abstract description 7
206010003119 arrhythmia Diseases 0.000 claims abstract description 6
230000006793 arrhythmia Effects 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 192
125000000217 alkyl group Chemical group 0.000 claims description 177
-1 methylsulfonylamino group Chemical group 0.000 claims description 162
125000001072 heteroaryl group Chemical group 0.000 claims description 149
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 136
125000001624 naphthyl group Chemical group 0.000 claims description 133
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 131
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 107
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 105
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 103
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 97
125000001424 substituent group Chemical group 0.000 claims description 90
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 80
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 64
150000003839 salts Chemical class 0.000 claims description 52
125000001041 indolyl group Chemical group 0.000 claims description 39
125000002098 pyridazinyl group Chemical group 0.000 claims description 39
125000005493 quinolyl group Chemical group 0.000 claims description 39
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 38
125000005956 isoquinolyl group Chemical group 0.000 claims description 38
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 38
125000000714 pyrimidinyl group Chemical group 0.000 claims description 38
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 38
125000003373 pyrazinyl group Chemical group 0.000 claims description 37
125000004076 pyridyl group Chemical group 0.000 claims description 37
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
125000002541 furyl group Chemical group 0.000 claims description 13
125000001544 thienyl group Chemical group 0.000 claims description 13
229940126601 medicinal product Drugs 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 9
230000002265 prevention Effects 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 5
230000036982 action potential Effects 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
229940088623 biologically active substance Drugs 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 4
230000000903 blocking effect Effects 0.000 claims description 3
206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000002876 beta blocker Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000002441 reversible effect Effects 0.000 claims description 2
230000033764 rhythmic process Effects 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229940097320 beta blocking agent Drugs 0.000 claims 1
239000012535 impurity Substances 0.000 claims 1
230000001404 mediated effect Effects 0.000 claims 1
239000003416 antiarrhythmic agent Substances 0.000 abstract description 9
210000002837 heart atrium Anatomy 0.000 abstract description 6
239000011591 potassium Substances 0.000 abstract description 5
229910052700 potassium Inorganic materials 0.000 abstract description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 3
230000003288 anthiarrhythmic effect Effects 0.000 abstract description 2
230000003111 delayed effect Effects 0.000 abstract description 2
230000003213 activating effect Effects 0.000 abstract 1
238000011321 prophylaxis Methods 0.000 abstract 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 80
239000000243 solution Substances 0.000 description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
239000002243 precursor Substances 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
238000007429 general method Methods 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
238000000034 method Methods 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
239000007787 solid Substances 0.000 description 14
239000000126 substance Substances 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
150000001412 amines Chemical class 0.000 description 13
230000003993 interaction Effects 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
NNJBQTDFDVLWEQ-UHFFFAOYSA-N 2-(sulfonylamino)benzoic acid Chemical class OC(=O)C1=CC=CC=C1N=S(=O)=O NNJBQTDFDVLWEQ-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000003814 drug Substances 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
WRHNIEDSWVZWKG-UHFFFAOYSA-N 2-(quinolin-8-ylsulfonylamino)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC2=CC=CN=C12 WRHNIEDSWVZWKG-UHFFFAOYSA-N 0.000 description 6
108091006146 Channels Proteins 0.000 description 6
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical compound C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
239000000969 carrier Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000002953 preparative HPLC Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
150000003335 secondary amines Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000004698 Polyethylene Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
230000037396 body weight Effects 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
SSOCGBMGAODFEA-UHFFFAOYSA-N 2-(sulfonylamino)benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1N=S(=O)=O SSOCGBMGAODFEA-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
206010003130 Arrhythmia supraventricular Diseases 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000012043 crude product Substances 0.000 description 3
QTUNRTDRPMOQNG-UHFFFAOYSA-N cyclopropyl(phenyl)methanamine;hydron;chloride Chemical compound Cl.C=1C=CC=CC=1C(N)C1CC1 QTUNRTDRPMOQNG-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
238000001802 infusion Methods 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
QINBXJHYDMZXEJ-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)cyclopropanamine;hydrochloride Chemical compound Cl.C=1C=CC=NC=1CNC1CC1 QINBXJHYDMZXEJ-UHFFFAOYSA-N 0.000 description 3
YKRXJFHSEYGWQY-UHFFFAOYSA-N n-[(1-methylimidazol-2-yl)methyl]-1-phenylmethanamine Chemical compound CN1C=CN=C1CNCC1=CC=CC=C1 YKRXJFHSEYGWQY-UHFFFAOYSA-N 0.000 description 3
230000001536 pro-arrhythmogenic effect Effects 0.000 description 3
239000002516 radical scavenger Substances 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
YLNWJSHBHAFMAT-UHFFFAOYSA-N 1-(5-methylfuran-2-yl)propan-1-amine Chemical compound CCC(N)C1=CC=C(C)O1 YLNWJSHBHAFMAT-UHFFFAOYSA-N 0.000 description 2
ZIUBMNMRMGMHGW-UHFFFAOYSA-N 1-cyclopropyl-n-phenylmethoxymethanimine Chemical compound C=1C=CC=CC=1CON=CC1CC1 ZIUBMNMRMGMHGW-UHFFFAOYSA-N 0.000 description 2
UEBFLTZXUXZPJO-UHFFFAOYSA-N 1-methylimidazole-2-carbaldehyde Chemical compound CN1C=CN=C1C=O UEBFLTZXUXZPJO-UHFFFAOYSA-N 0.000 description 2
JOTQNZHTWXIWHJ-UHFFFAOYSA-N 2-(quinolin-8-ylsulfonylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC2=CC=CN=C12 JOTQNZHTWXIWHJ-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
208000024172 Cardiovascular disease Diseases 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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
102000004257 Potassium Channel Human genes 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000001871 Tachycardia Diseases 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
IXTMWRCNAAVVAI-UHFFFAOYSA-N dofetilide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=C(NS(C)(=O)=O)C=C1 IXTMWRCNAAVVAI-UHFFFAOYSA-N 0.000 description 2
229960002994 dofetilide Drugs 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008103 glucose Substances 0.000 description 2
235000001727 glucose Nutrition 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
PEOCADSFXMBKCG-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)cyclopropanamine;hydrochloride Chemical compound Cl.C=1C=CN=CC=1CNC1CC1 PEOCADSFXMBKCG-UHFFFAOYSA-N 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
108020001213 potassium channel Proteins 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical compound OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
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CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
125000001400 nonyl 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])[H] 0.000 description 1
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
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
230000001575 pathological effect Effects 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
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
IOLQWLOHKZENDW-UHFFFAOYSA-N phenylisobutylamine Chemical compound CCC(N)CC1=CC=CC=C1 IOLQWLOHKZENDW-UHFFFAOYSA-N 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
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
239000003450 potassium channel blocker Substances 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
238000000039 preparative column chromatography Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
108090000765 processed proteins & peptides Proteins 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
125000003226 pyrazolyl group Chemical group 0.000 description 1
XAJWHCVLZBSLNC-UHFFFAOYSA-N pyridin-1-ium-2-sulfonyl chloride;chloride Chemical compound Cl.ClS(=O)(=O)C1=CC=CC=N1 XAJWHCVLZBSLNC-UHFFFAOYSA-N 0.000 description 1
KZVLNAGYSAKYMG-UHFFFAOYSA-N pyridine-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=N1 KZVLNAGYSAKYMG-UHFFFAOYSA-N 0.000 description 1
JQJOGAGLBDBMLU-UHFFFAOYSA-N pyridine-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=N1 JQJOGAGLBDBMLU-UHFFFAOYSA-N 0.000 description 1
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
ITXXHPLNLYEVQT-UHFFFAOYSA-N quinoline-3-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CN=C21 ITXXHPLNLYEVQT-UHFFFAOYSA-N 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000036279 refractory period Effects 0.000 description 1
230000002336 repolarization Effects 0.000 description 1
229920006395 saturated elastomer Polymers 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
239000013049 sediment Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 1
229960000652 sertindole Drugs 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
229960002370 sotalol Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000004544 sputter deposition Methods 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
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
CTIRHWCPXYGDGF-HDICACEKSA-N tedisamil Chemical compound [H][C@]12CN(CC3CC3)C[C@]([H])(CN(CC3CC3)C1)C21CCCC1 CTIRHWCPXYGDGF-HDICACEKSA-N 0.000 description 1
229960002926 tedisamil Drugs 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001425 triazolyl 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
230000002861 ventricular Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Pyridine Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

UA2004010206A 2001-06-12 2002-05-31 Anthranilic acid amides with heteroarylsulfonyl lateral chain, their use as medical and diagnostic agent and pharmaceutical composition containing them UA75412C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10128331A DE10128331A1 (de)	2001-06-12	2001-06-12	Anthranilsäureamide mit Heteroarylsulfonyl-Seitenkette, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen
PCT/EP2002/005956 WO2002100825A2 (de)	2001-06-12	2002-05-31	Anthranilsäureamide mit heteroarylsulfonyl-seitenkette und ihre verwendung als antiarrhythmische wirkstoffe

Publications (1)

Publication Number	Publication Date
UA75412C2 true UA75412C2 (en)	2006-04-17

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UA2004010206A UA75412C2 (en)	2001-06-12	2002-05-31	Anthranilic acid amides with heteroarylsulfonyl lateral chain, their use as medical and diagnostic agent and pharmaceutical composition containing them

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US (2)	US6903216B2 (pt)
EP (1)	EP1399423B9 (pt)
JP (1)	JP4422477B2 (pt)
KR (1)	KR100863924B1 (pt)
CN (1)	CN1247544C (pt)
AR (1)	AR036045A1 (pt)
AT (1)	ATE378318T1 (pt)
AU (1)	AU2002316939B2 (pt)
BG (1)	BG108415A (pt)
BR (1)	BR0210374A (pt)
CA (1)	CA2450076C (pt)
CO (1)	CO5540283A2 (pt)
CR (1)	CR7140A (pt)
CY (1)	CY1107427T1 (pt)
CZ (1)	CZ20033361A3 (pt)
DE (2)	DE10128331A1 (pt)
DK (1)	DK1399423T3 (pt)
EC (1)	ECSP034883A (pt)
EE (1)	EE05196B1 (pt)
ES (1)	ES2295360T3 (pt)
HK (1)	HK1065316A1 (pt)
HR (1)	HRP20031028A2 (pt)
HU (1)	HUP0400159A3 (pt)
IL (2)	IL159247A0 (pt)
MA (1)	MA27037A1 (pt)
MX (1)	MXPA03010875A (pt)
MY (1)	MY138341A (pt)
NO (1)	NO20035450D0 (pt)
NZ (1)	NZ530081A (pt)
OA (1)	OA12631A (pt)
PE (1)	PE20021066A1 (pt)
PL (1)	PL364371A1 (pt)
PT (1)	PT1399423E (pt)
RS (1)	RS97703A (pt)
RU (1)	RU2293727C2 (pt)
SK (1)	SK15222003A3 (pt)
TN (1)	TNSN03134A1 (pt)
TW (1)	TWI304400B (pt)
UA (1)	UA75412C2 (pt)
WO (1)	WO2002100825A2 (pt)
ZA (1)	ZA200308520B (pt)

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DE10128331A1 (de) *	2001-06-12	2002-12-19	Aventis Pharma Gmbh	Anthranilsäureamide mit Heteroarylsulfonyl-Seitenkette, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen
US7119112B2 (en) *	2002-02-28	2006-10-10	Icagen, Inc.	Sulfonamides as potassium channel blockers
EP1500650A4 (en) *	2002-04-26	2006-08-23	Ishihara Sangyo Kaisha	PYRIDINE COMPOUNDS OR SALTS THEREOF AND HERBICIDES CONTAINING SAME
EP1388535A1 (en) *	2002-08-07	2004-02-11	Aventis Pharma Deutschland GmbH	Acylated arylcycloalkylamines and their use as pharmaceuticals
DE10312061A1 (de) *	2003-03-18	2004-09-30	Aventis Pharma Deutschland Gmbh	Kombination von Phenylcarbonsäureamiden mit Blockern des IK-Kanals und deren Verwendung zur Behandlung von Vorhofarrhythmien
GB0315950D0 (en)	2003-06-11	2003-08-13	Xention Discovery Ltd	Compounds
EP1489071A1 (en) *	2003-06-18	2004-12-22	4Sc Ag	N-substituted, 3,4-dihydro-1H-isoquinoline as potassium channels modulators
WO2005016896A1 (en)	2003-08-08	2005-02-24	Janssen Pharmaceutica, N.V.	2- (quinoxalin-5-ylsulfonylamino) -benzamide compounds as cck2 modulators
DE10341233A1 (de) *	2003-09-08	2005-03-24	Aventis Pharma Deutschland Gmbh	Kombination von Phenylcarbonsäureamiden mit beta-Adrenozeptoren-Blockern und deren Verwendung zur Behandlung von Vorhofarrhythmien
DE102004009931A1 (de) *	2004-02-26	2005-09-15	Aventis Pharma Deutschland Gmbh	Kv1.5-Blocker zur selektiven Steigerung der Vorhofkontraktilität und Behandlung der Herzinsuffizienz
GB0412986D0 (en)	2004-06-10	2004-07-14	Xention Discovery Ltd	Compounds
US7569589B2 (en)	2004-07-29	2009-08-04	Merck & Co., Inc.	Potassium channel inhibitors
KR20070057252A (ko)	2004-09-24	2007-06-04	얀센 파마슈티카 엔.브이.	설폰아미드 화합물
US7576212B2 (en)	2004-12-09	2009-08-18	Xention Limited	Thieno[2,3-B] pyridines as potassium channel inhibitors
GB0525164D0 (en)	2005-12-09	2006-01-18	Xention Discovery Ltd	Compounds
KR101390239B1 (ko) *	2006-04-27	2014-04-30	사노피-아벤티스 도이칠란트 게엠베하	Ｔａｓｋ-1 및 ｔａｓｋ-3 이온 채널 억제제
WO2008124524A2 (en) *	2007-04-03	2008-10-16	Janssen Pharmaceutica N.V.	Aryl sulfonamide compounds as modulators of the cck2 receptor
GB0815782D0 (en)	2008-08-29	2008-10-08	Xention Ltd	Novel potassium channel blockers
GB0815781D0 (en)	2008-08-29	2008-10-08	Xention Ltd	Novel potassium channel blockers
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2001
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- 2002-05-31 DK DK02745333T patent/DK1399423T3/da active
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Also Published As

Publication number	Publication date
US6903216B2 (en)	2005-06-07
MXPA03010875A (es)	2004-02-17
TNSN03134A1 (en)	2005-12-23
WO2002100825A2 (de)	2002-12-19
EP1399423B1 (de)	2007-11-14
DE10128331A1 (de)	2002-12-19
EP1399423B9 (de)	2008-02-27
NZ530081A (en)	2005-07-29
CA2450076A1 (en)	2002-12-19
AR036045A1 (es)	2004-08-04
EE05196B1 (et)	2009-08-17
ES2295360T3 (es)	2008-04-16
US20030114499A1 (en)	2003-06-19
IL159247A0 (en)	2004-06-01
HUP0400159A2 (hu)	2004-07-28
CY1107427T1 (el)	2012-12-19
KR20040030668A (ko)	2004-04-09
HRP20031028A2 (en)	2005-10-31
CO5540283A2 (es)	2005-07-29
ZA200308520B (en)	2004-09-06
PE20021066A1 (es)	2003-01-21
DE50211213D1 (de)	2007-12-27
SK15222003A3 (sk)	2004-06-08
BR0210374A (pt)	2004-07-13
IL159247A (en)	2010-06-16
BG108415A (en)	2004-07-30
WO2002100825A3 (de)	2003-12-11
CN1529695A (zh)	2004-09-15
CN1247544C (zh)	2006-03-29
CR7140A (es)	2004-04-15
RS97703A (en)	2006-12-15
HK1065316A1 (en)	2005-02-18
TWI304400B (en)	2008-12-21
RU2004100302A (ru)	2005-04-10
KR100863924B1 (ko)	2008-10-17
HUP0400159A3 (en)	2008-10-28
JP2004533464A (ja)	2004-11-04
US7235664B2 (en)	2007-06-26
NO20035450D0 (no)	2003-12-08
AU2002316939B2 (en)	2006-11-23
PL364371A1 (en)	2004-12-13
ATE378318T1 (de)	2007-11-15
RU2293727C2 (ru)	2007-02-20
JP4422477B2 (ja)	2010-02-24
EP1399423A2 (de)	2004-03-24
CZ20033361A3 (cs)	2004-05-12
MA27037A1 (fr)	2004-12-20
CA2450076C (en)	2010-11-30
DK1399423T3 (da)	2008-03-17
EE200300558A (et)	2004-02-16
PT1399423E (pt)	2008-02-07
MY138341A (en)	2009-05-29
US20050137200A1 (en)	2005-06-23
OA12631A (fr)	2006-06-14
ECSP034883A (es)	2004-01-28

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