BG103829A - Нитробензамид, приложим като антиаритмично средство - Google Patents

Нитробензамид, приложим като антиаритмично средство Download PDF

Info

Publication number: BG103829A
Authority: BG; Bulgaria
Prior art keywords: compound; pharmaceutically acceptable; propyl; provides; dimethoxyphenyl
Prior art date: 1997-03-27

Application number

BG103829A

Other languages

Bulgarian (bg)

English (en)

Inventor

Graham SLATER

Paul WESTLAKE

Original Assignee

Smithkline Beecham P.L.C.

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.)

1997-03-27

Filing date

1999-10-22

Publication date

2000-04-28

1999-10-22 Application filed by Smithkline Beecham P.L.C. filed Critical Smithkline Beecham P.L.C.

2000-04-28 Publication of BG103829A publication Critical patent/BG103829A/bg

Links

KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical compound NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 title description 3
239000003416 antiarrhythmic agent Substances 0.000 title description 3
230000003288 anthiarrhythmic effect Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 12
239000007787 solid Substances 0.000 claims abstract description 10
238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 9
239000000126 substance Substances 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 8
238000002329 infrared spectrum Methods 0.000 claims abstract description 8
238000002844 melting Methods 0.000 claims abstract description 7
230000008018 melting Effects 0.000 claims abstract description 7
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims abstract 2
206010003119 arrhythmia Diseases 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 9
239000003125 aqueous solvent Substances 0.000 claims description 8
230000000302 ischemic effect Effects 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
230000006793 arrhythmia Effects 0.000 claims description 7
QLUVAVFNMRXIIZ-UHFFFAOYSA-N n-[3-[2-(3,4-dimethoxyphenyl)ethylamino]propyl]-4-nitrobenzamide;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CCNCCCNC(=O)C1=CC=C([N+]([O-])=O)C=C1 QLUVAVFNMRXIIZ-UHFFFAOYSA-N 0.000 claims description 7
230000033764 rhythmic process Effects 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
238000011321 prophylaxis Methods 0.000 claims description 4
230000001225 therapeutic effect Effects 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
YLTPZEHUQLEQMN-UHFFFAOYSA-N 2-[3-[2-(3,4-dimethoxyphenyl)ethylamino]propyl]-4-nitrobenzamide hydrochloride Chemical compound Cl.COC=1C=C(C=CC1OC)CCNCCCC1=C(C(=O)N)C=CC(=C1)[N+](=O)[O-] YLTPZEHUQLEQMN-UHFFFAOYSA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 6
239000000843 powder Substances 0.000 abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 18
239000000243 solution Substances 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 8
239000000725 suspension Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
238000009472 formulation Methods 0.000 description 5
230000036571 hydration Effects 0.000 description 5
238000006703 hydration reaction Methods 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
206010047281 Ventricular arrhythmia Diseases 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000005388 cross polarization Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
238000011067 equilibration Methods 0.000 description 3
239000000945 filler Substances 0.000 description 3
238000011049 filling Methods 0.000 description 3
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
239000004909 Moisturizer Substances 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
239000013543 active substance Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
239000003925 fat Substances 0.000 description 2
235000019197 fats Nutrition 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000001333 moisturizer Effects 0.000 description 2
MLPSBRLFRKNBKR-UHFFFAOYSA-N n-[3-[2-(3,4-dimethoxyphenyl)ethylamino]propyl]-4-nitrobenzamide;hydrate;hydrochloride Chemical compound O.Cl.C1=C(OC)C(OC)=CC=C1CCNCCCNC(=O)C1=CC=C([N+]([O-])=O)C=C1 MLPSBRLFRKNBKR-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000002028 premature Effects 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
238000000279 solid-state nuclear magnetic resonance spectrum Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
230000002110 toxicologic effect Effects 0.000 description 2
231100000759 toxicological effect Toxicity 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
238000004482 13C cross polarization magic angle spinning Methods 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
235000019489 Almond oil 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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
241000282412 Homo Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
229920004459 Kel-F® PCTFE Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
206010027783 Moaning Diseases 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
208000004301 Sinus Arrhythmia Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000008168 almond oil Substances 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
229940063655 aluminum stearate Drugs 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
230000002763 arrhythmic effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
238000012769 bulk production Methods 0.000 description 1
239000008364 bulk solution Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical compound FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000002131 composite material Substances 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
230000008828 contractile function Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000010247 heart contraction Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
XEAKAKKNLOUHDV-UHFFFAOYSA-N n-[3-[2-(3,4-dimethoxyphenyl)ethylamino]propyl]-4-nitrobenzamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNCCCNC(=O)C1=CC=C([N+]([O-])=O)C=C1 XEAKAKKNLOUHDV-UHFFFAOYSA-N 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
208000008510 paroxysmal tachycardia Diseases 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000001536 pro-arrhythmogenic effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000012385 systemic delivery Methods 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
230000000213 tachycardiac effect Effects 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BG103829A 1997-03-27 1999-10-22 Нитробензамид, приложим като антиаритмично средство BG103829A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9706376.2A GB9706376D0 (en)	1997-03-27	1997-03-27	Novel pharmaceutical
PCT/EP1998/001913 WO1998043947A1 (en)	1997-03-27	1998-03-24	Nitro-benzamide useful as anti-arrhythmic agent

Publications (1)

Publication Number	Publication Date
BG103829A true BG103829A (bg)	2000-04-28

Family

ID=10809958

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG103829A BG103829A (bg)	1997-03-27	1999-10-22	Нитробензамид, приложим като антиаритмично средство

Country Status (37)

Country	Link
US (1)	US20040092771A1 (zh)
EP (1)	EP0971882B1 (zh)
JP (1)	JP2001518088A (zh)
KR (1)	KR20010005566A (zh)
CN (1)	CN1257478A (zh)
AP (1)	AP1205A (zh)
AT (1)	ATE228997T1 (zh)
AU (1)	AU741476B2 (zh)
BG (1)	BG103829A (zh)
BR (1)	BR9809054A (zh)
CA (1)	CA2285197A1 (zh)
DE (1)	DE69809891T2 (zh)
DK (1)	DK0971882T3 (zh)
DZ (1)	DZ2452A1 (zh)
EA (1)	EA002439B1 (zh)
EG (1)	EG21226A (zh)
ES (1)	ES2189163T3 (zh)
GB (1)	GB9706376D0 (zh)
HK (1)	HK1025089A1 (zh)
HU (1)	HUP0001683A3 (zh)
ID (1)	ID22787A (zh)
IL (1)	IL132042A0 (zh)
IN (1)	IN188180B (zh)
MA (1)	MA26477A1 (zh)
NO (1)	NO994682L (zh)
NZ (1)	NZ337794A (zh)
OA (1)	OA11200A (zh)
PE (1)	PE61799A1 (zh)
PL (1)	PL335879A1 (zh)
PT (1)	PT971882E (zh)
SK (1)	SK283056B6 (zh)
TR (1)	TR199902356T2 (zh)
TW (1)	TW518318B (zh)
UA (1)	UA57066C2 (zh)
UY (1)	UY24937A1 (zh)
WO (1)	WO1998043947A1 (zh)
ZA (1)	ZA982558B (zh)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9923934D0 (en) *	1999-10-08	1999-12-08	Smithkline Beecham Plc	Novel pharmaceutical
GB9923933D0 (en) *	1999-10-08	1999-12-08	Smithkline Beecham Lab	Novel pharmaceutical
US8483008B2 (en) *	2008-11-08	2013-07-09	Westerngeco L.L.C.	Coil shooting mode

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2726267B1 (fr) *	1994-10-26	1998-01-02	Smithkline Beecham Lab	Nouveaux agents anti-arythmiques, compositions pharmaceutiques les contenant, et procede pour les preparer

1997
- 1997-03-27 GB GBGB9706376.2A patent/GB9706376D0/en active Pending
1998
- 1998-03-24 HU HU0001683A patent/HUP0001683A3/hu unknown
- 1998-03-24 DE DE69809891T patent/DE69809891T2/de not_active Expired - Fee Related
- 1998-03-24 CN CN98805301A patent/CN1257478A/zh active Pending
- 1998-03-24 KR KR1019997008629A patent/KR20010005566A/ko not_active Application Discontinuation
- 1998-03-24 AT AT98920498T patent/ATE228997T1/de not_active IP Right Cessation
- 1998-03-24 ES ES98920498T patent/ES2189163T3/es not_active Expired - Lifetime
- 1998-03-24 AP APAP/P/1999/001651A patent/AP1205A/en active
- 1998-03-24 JP JP54116698A patent/JP2001518088A/ja not_active Ceased
- 1998-03-24 CA CA002285197A patent/CA2285197A1/en not_active Abandoned
- 1998-03-24 ID IDW991093A patent/ID22787A/id unknown
- 1998-03-24 SK SK1302-99A patent/SK283056B6/sk unknown
- 1998-03-24 NZ NZ337794A patent/NZ337794A/en unknown
- 1998-03-24 EP EP98920498A patent/EP0971882B1/en not_active Expired - Lifetime
- 1998-03-24 BR BR9809054-2A patent/BR9809054A/pt not_active IP Right Cessation
- 1998-03-24 PL PL98335879A patent/PL335879A1/xx unknown
- 1998-03-24 TR TR1999/02356T patent/TR199902356T2/xx unknown
- 1998-03-24 WO PCT/EP1998/001913 patent/WO1998043947A1/en not_active Application Discontinuation
- 1998-03-24 PT PT98920498T patent/PT971882E/pt unknown
- 1998-03-24 EA EA199900879A patent/EA002439B1/ru not_active IP Right Cessation
- 1998-03-24 IL IL13204298A patent/IL132042A0/xx unknown
- 1998-03-24 DK DK98920498T patent/DK0971882T3/da active
- 1998-03-24 UA UA99095241A patent/UA57066C2/uk unknown
- 1998-03-24 AU AU73341/98A patent/AU741476B2/en not_active Ceased
- 1998-03-25 MA MA25011A patent/MA26477A1/fr unknown
- 1998-03-25 DZ DZ980062A patent/DZ2452A1/xx active
- 1998-03-25 PE PE1998000218A patent/PE61799A1/es not_active Application Discontinuation
- 1998-03-26 EG EG34498A patent/EG21226A/xx active
- 1998-03-26 ZA ZA9802558A patent/ZA982558B/xx unknown
- 1998-03-26 IN IN786DE1998 patent/IN188180B/en unknown
- 1998-03-26 UY UY24937A patent/UY24937A1/es unknown
- 1998-04-01 TW TW087104862A patent/TW518318B/zh not_active IP Right Cessation
1999
- 1999-09-24 NO NO994682A patent/NO994682L/no not_active Application Discontinuation
- 1999-09-27 OA OA9900218A patent/OA11200A/en unknown
- 1999-10-22 BG BG103829A patent/BG103829A/bg unknown
2000
- 2000-07-17 HK HK00104363A patent/HK1025089A1/xx not_active IP Right Cessation
2003
- 2003-12-02 US US10/725,893 patent/US20040092771A1/en not_active Abandoned

Also Published As

Publication number	Publication date
NO994682D0 (no)	1999-09-24
SK283056B6 (sk)	2003-02-04
TW518318B (en)	2003-01-21
NO994682L (no)	1999-09-24
IN188180B (zh)	2002-08-31
UA57066C2 (uk)	2003-06-16
CN1257478A (zh)	2000-06-21
UY24937A1 (es)	2000-12-29
BR9809054A (pt)	2000-08-01
EA199900879A1 (ru)	2000-04-24
DZ2452A1 (fr)	2003-01-18
PT971882E (pt)	2003-04-30
HUP0001683A2 (hu)	2000-09-28
JP2001518088A (ja)	2001-10-09
HUP0001683A3 (en)	2002-11-28
ES2189163T3 (es)	2003-07-01
AU741476B2 (en)	2001-11-29
EP0971882B1 (en)	2002-12-04
ZA982558B (en)	1999-09-27
PE61799A1 (es)	1999-09-10
EA002439B1 (ru)	2002-04-25
NZ337794A (en)	2001-06-29
IL132042A0 (en)	2001-03-19
AP9901651A0 (en)	1999-09-30
OA11200A (en)	2003-05-21
US20040092771A1 (en)	2004-05-13
AP1205A (en)	2003-09-17
DE69809891D1 (de)	2003-01-16
HK1025089A1 (en)	2000-11-03
EP0971882A1 (en)	2000-01-19
PL335879A1 (en)	2000-05-22
DK0971882T3 (da)	2003-03-31
TR199902356T2 (xx)	2000-01-21
DE69809891T2 (de)	2003-07-24
MA26477A1 (fr)	2004-12-20
GB9706376D0 (en)	1997-05-14
ID22787A (id)	1999-12-09
KR20010005566A (ko)	2001-01-15
EG21226A (en)	2001-03-31
CA2285197A1 (en)	1998-10-08
AU7334198A (en)	1998-10-22
WO1998043947A1 (en)	1998-10-08
ATE228997T1 (de)	2002-12-15
SK130299A3 (en)	2000-05-16

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