HRP20031028A2 - Anthranilic acid amides with a heteroarylsulfonyl side chain, method for the production thereof, use thereof as a medicament or diagnostic agent and pharmaceutical preparations containing said compounds - Google Patents

Anthranilic acid amides with a heteroarylsulfonyl side chain, method for the production thereof, use thereof as a medicament or diagnostic agent and pharmaceutical preparations containing said compounds Download PDF

Info

Publication number: HRP20031028A2
Authority: HR; Croatia
Prior art keywords: phenyl; heteroaryl; alkyl; naphthyl; hydrogen
Prior art date: 2001-06-12

Application number

HR20031028A

Other languages

English (en)

Croatian (hr)

Inventor

Brendel Joachim

Bhme Thomas

Peukert Stefan

Kleemann Heinz-Werner

Original Assignee

Aventis Pharma Deutschland Gmbh

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

2003-12-11

Publication date

2005-10-31

2003-12-11 Application filed by Aventis Pharma Deutschland Gmbh filed Critical Aventis Pharma Deutschland Gmbh

2005-10-31 Publication of HRP20031028A2 publication Critical patent/HRP20031028A2/hr

Links

150000001875 compounds Chemical class 0.000 title claims description 98
239000003814 drug Substances 0.000 title claims description 16
238000004519 manufacturing process Methods 0.000 title claims description 8
239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
238000000034 method Methods 0.000 title description 10
PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title description 5
239000000032 diagnostic agent Substances 0.000 title 1
229940039227 diagnostic agent Drugs 0.000 title 1
125000005143 heteroarylsulfonyl group Chemical group 0.000 title 1
-1 dimethylamino, sulfamoyl Chemical group 0.000 claims description 229
125000004432 carbon atom Chemical group C* 0.000 claims description 173
125000001072 heteroaryl group Chemical group 0.000 claims description 149
125000000217 alkyl group Chemical group 0.000 claims description 147
229910052801 chlorine Inorganic materials 0.000 claims description 145
229910052731 fluorine Inorganic materials 0.000 claims description 144
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 142
125000001624 naphthyl group Chemical group 0.000 claims description 139
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 137
229910052739 hydrogen Inorganic materials 0.000 claims description 131
239000001257 hydrogen Substances 0.000 claims description 131
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 117
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 111
150000002431 hydrogen Chemical class 0.000 claims description 103
125000001424 substituent group Chemical group 0.000 claims description 94
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
150000003839 salts Chemical class 0.000 claims description 55
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 41
125000005956 isoquinolyl group Chemical group 0.000 claims description 41
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 41
125000003373 pyrazinyl group Chemical group 0.000 claims description 41
125000004076 pyridyl group Chemical group 0.000 claims description 41
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 41
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 41
125000005493 quinolyl group Chemical group 0.000 claims description 41
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 41
125000000714 pyrimidinyl group Chemical group 0.000 claims description 40
125000001041 indolyl group Chemical group 0.000 claims description 39
125000002098 pyridazinyl group Chemical group 0.000 claims description 38
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 33
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 32
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 15
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
229910052794 bromium Inorganic materials 0.000 claims description 12
229940079593 drug Drugs 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 12
206010003658 Atrial Fibrillation Diseases 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 9
238000011321 prophylaxis Methods 0.000 claims description 8
238000002560 therapeutic procedure Methods 0.000 claims description 7
206010003662 Atrial flutter Diseases 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 5
206010003119 arrhythmia 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
230000000903 blocking effect Effects 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 3
230000006793 arrhythmia Effects 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
229920000728 polyester Polymers 0.000 claims description 3
239000002876 beta blocker Substances 0.000 claims 1
229940097320 beta blocking agent Drugs 0.000 claims 1
230000001404 mediated effect Effects 0.000 claims 1
230000033764 rhythmic process Effects 0.000 claims 1
239000000460 chlorine Substances 0.000 description 73
239000000243 solution Substances 0.000 description 41
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 38
239000000543 intermediate Substances 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
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 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000000203 mixture Substances 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
239000007787 solid Substances 0.000 description 14
230000033228 biological regulation Effects 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
150000001412 amines Chemical class 0.000 description 11
239000002904 solvent Substances 0.000 description 11
239000007832 Na2SO4 Substances 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
239000000047 product Substances 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
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 9
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
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
NNJBQTDFDVLWEQ-UHFFFAOYSA-N 2-(sulfonylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N=S(=O)=O NNJBQTDFDVLWEQ-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
239000003416 antiarrhythmic agent Substances 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
108091006146 Channels Proteins 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
230000009471 action Effects 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
238000011282 treatment Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
239000002253 acid Substances 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
230000003288 anthiarrhythmic effect Effects 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
229910000029 sodium carbonate Inorganic materials 0.000 description 5
235000017550 sodium carbonate Nutrition 0.000 description 5
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
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 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
102000004257 Potassium Channel Human genes 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000002585 base Substances 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
239000000969 carrier Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
230000003111 delayed effect Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
210000002837 heart atrium Anatomy 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
108020001213 potassium channel Proteins 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
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 3
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
RSFXOPDETMHJCK-HNNXBMFYSA-N 2-amino-n-[(1s)-1-phenylpropyl]benzamide Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1N RSFXOPDETMHJCK-HNNXBMFYSA-N 0.000 description 3
SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 3
TUNNNFLDZNSBQK-UHFFFAOYSA-N 5-fluoro-2-(quinolin-8-ylsulfonylamino)benzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1NS(=O)(=O)C1=CC=CC2=CC=CN=C12 TUNNNFLDZNSBQK-UHFFFAOYSA-N 0.000 description 3
QFPGRDDFLCHSMR-UHFFFAOYSA-N 6-methylpyridine-3-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=N1 QFPGRDDFLCHSMR-UHFFFAOYSA-N 0.000 description 3
206010003130 Arrhythmia supraventricular Diseases 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
101001026214 Homo sapiens Potassium voltage-gated channel subfamily A member 5 Proteins 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
230000003213 activating effect Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003795 chemical substances by application Substances 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
239000003995 emulsifying agent Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
238000001802 infusion Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-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
WIKJAZKXHCHEGC-UHFFFAOYSA-N n-cyclopropyl-n-methylpyridin-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=NC=1N(C)C1CC1 WIKJAZKXHCHEGC-UHFFFAOYSA-N 0.000 description 3
CYTORULYNPVOJI-UHFFFAOYSA-N n-cyclopropyl-n-methylpyridin-3-amine;hydrochloride Chemical compound Cl.C=1C=CN=CC=1N(C)C1CC1 CYTORULYNPVOJI-UHFFFAOYSA-N 0.000 description 3
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000001536 pro-arrhythmogenic effect Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
AQFLVLHRZFLDDV-VIFPVBQESA-N (1s)-1-phenylpropan-1-amine Chemical compound CC[C@H](N)C1=CC=CC=C1 AQFLVLHRZFLDDV-VIFPVBQESA-N 0.000 description 2
GGUMJDNMKLAOQA-UHFFFAOYSA-N 1-cyclopropyl-1-(6-methoxypyridin-2-yl)-n-phenylmethoxymethanamine Chemical compound COC1=CC=CC(C(NOCC=2C=CC=CC=2)C2CC2)=N1 GGUMJDNMKLAOQA-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
PALFZIMHIMRYFF-UHFFFAOYSA-N 1-cyclopropyl-n-pyridin-2-ylmethanimine Chemical compound C1CC1C=NC1=CC=CC=N1 PALFZIMHIMRYFF-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
COHYOBKZKMKMIX-UHFFFAOYSA-N 1-phenyl-n-(pyridin-3-ylmethyl)methanamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CN=C1 COHYOBKZKMKMIX-UHFFFAOYSA-N 0.000 description 2
VQGKOCARCUCUMC-UHFFFAOYSA-N 1-pyridin-3-ylpropan-1-amine Chemical compound CCC(N)C1=CC=CN=C1 VQGKOCARCUCUMC-UHFFFAOYSA-N 0.000 description 2
AFHFHXVRHACYSR-UHFFFAOYSA-N 1-pyridin-4-ylpropan-1-one Chemical compound CCC(=O)C1=CC=NC=C1 AFHFHXVRHACYSR-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
DLDOXWDYWXYCLC-INIZCTEOSA-N 2-amino-5-methoxy-n-[(1s)-1-phenylpropyl]benzamide Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C1=CC(OC)=CC=C1N DLDOXWDYWXYCLC-INIZCTEOSA-N 0.000 description 2
FWRBAPRINZNBIZ-UHFFFAOYSA-N 2-amino-5-methyl-n-[1-(5-methylfuran-2-yl)propyl]benzamide Chemical compound C=1C=C(C)OC=1C(CC)NC(=O)C1=CC(C)=CC=C1N FWRBAPRINZNBIZ-UHFFFAOYSA-N 0.000 description 2
SZCPTRGBOVXVCA-UHFFFAOYSA-N 2-amino-6-chlorobenzoic acid Chemical compound NC1=CC=CC(Cl)=C1C(O)=O SZCPTRGBOVXVCA-UHFFFAOYSA-N 0.000 description 2
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
KTDYNOKUFSRVDV-UHFFFAOYSA-N 5-methyl-n-[1-(5-methylfuran-2-yl)propyl]-2-(pyridin-2-ylsulfonylamino)benzamide Chemical compound C=1C=C(C)OC=1C(CC)NC(=O)C1=CC(C)=CC=C1NS(=O)(=O)C1=CC=CC=N1 KTDYNOKUFSRVDV-UHFFFAOYSA-N 0.000 description 2
LDFISZJWVADWOR-UHFFFAOYSA-N 5-methyl-n-[1-(5-methylfuran-2-yl)propyl]-2-nitrobenzamide Chemical compound C=1C=C(C)OC=1C(CC)NC(=O)C1=CC(C)=CC=C1[N+]([O-])=O LDFISZJWVADWOR-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
208000024172 Cardiovascular disease Diseases 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
241001465754 Metazoa Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
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HGCKEQOMTKMGHK-UHFFFAOYSA-N n-benzyl-n-(pyridin-2-ylmethyl)-2-(quinolin-8-ylsulfonylamino)benzamide Chemical compound C=1C=CC=C(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C=1C(=O)N(CC=1N=CC=CC=1)CC1=CC=CC=C1 HGCKEQOMTKMGHK-UHFFFAOYSA-N 0.000 description 1
PPHSOCROFCONHN-UHFFFAOYSA-N n-benzyl-n-(pyridin-3-ylmethyl)-2-(quinolin-8-ylsulfonylamino)benzamide Chemical compound C=1C=CC=C(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C=1C(=O)N(CC=1C=NC=CC=1)CC1=CC=CC=C1 PPHSOCROFCONHN-UHFFFAOYSA-N 0.000 description 1
DYAXICMTNLURRU-UHFFFAOYSA-N n-benzyl-n-cyclopropyl-2-(quinolin-8-ylsulfonylamino)benzamide Chemical compound C=1C=CC=C(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C=1C(=O)N(C1CC1)CC1=CC=CC=C1 DYAXICMTNLURRU-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
NMRFEBKWDIFJNE-UHFFFAOYSA-N n-cyclohexyl-2-(quinolin-8-ylsulfonylamino)benzamide Chemical compound C=1C=CC=C(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C=1C(=O)NC1CCCCC1 NMRFEBKWDIFJNE-UHFFFAOYSA-N 0.000 description 1
ZEBGMLIVBIDGOZ-UHFFFAOYSA-N n-cyclopropyl-n-(pyridin-3-ylmethyl)-2-(quinolin-8-ylsulfonylamino)benzamide Chemical compound C=1C=CC=C(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C=1C(=O)N(C1CC1)CC1=CC=CN=C1 ZEBGMLIVBIDGOZ-UHFFFAOYSA-N 0.000 description 1
GFUKEKROWXOBQW-UHFFFAOYSA-N n-cyclopropyl-n-phenyl-2-(quinolin-8-ylsulfonylamino)benzamide Chemical compound C=1C=CC=C(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C=1C(=O)N(C=1C=CC=CC=1)C1CC1 GFUKEKROWXOBQW-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
INKGFTSGGGUXDH-UHFFFAOYSA-N n-methyl-n-phenylpyridin-3-amine Chemical compound C=1C=CN=CC=1N(C)C1=CC=CC=C1 INKGFTSGGGUXDH-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
125000004123 n-propyl group Chemical group [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
229910052757 nitrogen Inorganic materials 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
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
125000002971 oxazolyl group Chemical group 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
229910052760 oxygen Inorganic materials 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
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
230000002085 persistent effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 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
230000009090 positive inotropic effect Effects 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
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000001737 promoting 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
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-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
VHXJRLYFEJAIAM-UHFFFAOYSA-N quinoline-2-sulfonyl chloride Chemical compound C1=CC=CC2=NC(S(=O)(=O)Cl)=CC=C21 VHXJRLYFEJAIAM-UHFFFAOYSA-N 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
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000036279 refractory period Effects 0.000 description 1
230000002336 repolarization Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 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
229960000652 sertindole Drugs 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
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229960002370 sotalol Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 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
229910052717 sulfur Inorganic materials 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
230000002459 sustained effect Effects 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
229960002926 tedisamil Drugs 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
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
238000002604 ultrasonography Methods 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
239000003039 volatile agent Substances 0.000 description 1
238000005303 weighing Methods 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

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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)
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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)

HR20031028A 2001-06-12 2003-12-11 Anthranilic acid amides with a heteroarylsulfonyl side chain, method for the production thereof, use thereof as a medicament or diagnostic agent and pharmaceutical preparations containing said compounds HRP20031028A2 (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
HRP20031028A2 true HRP20031028A2 (en)	2005-10-31

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HR20031028A HRP20031028A2 (en)	2001-06-12	2003-12-11	Anthranilic acid amides with a heteroarylsulfonyl side chain, method for the production thereof, use thereof as a medicament or diagnostic agent and pharmaceutical preparations containing said compounds

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

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2001
- 2001-06-12 DE DE10128331A patent/DE10128331A1/de not_active Withdrawn
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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
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
UA75412C2 (en)	2006-04-17
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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Date	Code	Title	Description
2005-10-31	A1OB	Publication of a patent application
2006-02-10	PNAN	Change of the applicant name, address/residence	Owner name: SANOFI-AVENTIS DEUTSCHLAND GMBH, DE
2006-04-21	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2010-05-29	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20100529 Year of fee payment: 9
2012-02-16	ODBC	Application rejected

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