SK3292002A3 - Benzopyran derivative - Google Patents

Benzopyran derivative Download PDF

Info

Publication number: SK3292002A3
Authority: SK; Slovakia
Prior art keywords: group; synthetic example; alkyl group; pharmaceutically acceptable; nmr
Prior art date: 1999-09-17

Application number

SK329-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Keizo Tanikawa

Kazuhiko Ohrai

Kazufumi Yanagihara

Yukihiro Shigeta

Toru Tsukagoshi

Toru Yamashita

Original Assignee

Nissan Chemical Ind Ltd

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.)

1999-09-17

Filing date

2000-09-14

Publication date

2003-04-01

2000-09-14 Application filed by Nissan Chemical Ind Ltd filed Critical Nissan Chemical Ind Ltd

2003-04-01 Publication of SK3292002A3 publication Critical patent/SK3292002A3/sk

Links

150000001562 benzopyrans Chemical class 0.000 title claims abstract description 20
-1 (substituted)phenyl group Chemical group 0.000 claims abstract description 254
150000003839 salts Chemical class 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
239000004480 active ingredient Substances 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 9
206010003119 arrhythmia Diseases 0.000 claims description 9
230000006793 arrhythmia Effects 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
150000002367 halogens Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 65
230000000694 effects Effects 0.000 abstract description 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 6
239000003416 antiarrhythmic agent Substances 0.000 abstract description 6
230000036747 functional refractory period Effects 0.000 abstract 1
238000005160 1H NMR spectroscopy Methods 0.000 description 54
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 49
239000013078 crystal Substances 0.000 description 36
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 30
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 27
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 26
239000012071 phase Substances 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 23
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 23
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 22
239000000243 solution Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 21
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 18
210000003205 muscle Anatomy 0.000 description 17
239000000203 mixture Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
230000001746 atrial effect Effects 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 10
230000002035 prolonged effect Effects 0.000 description 10
230000002861 ventricular Effects 0.000 description 10
150000003840 hydrochlorides Chemical class 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
230000036982 action potential Effects 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000002775 capsule Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000002674 ointment Substances 0.000 description 5
230000003389 potentiating effect Effects 0.000 description 5
ACUOAQKUXNEDQR-UHFFFAOYSA-N 2,2-dimethyl-7-nitrochromene Chemical compound [O-][N+](=O)C1=CC=C2C=CC(C)(C)OC2=C1 ACUOAQKUXNEDQR-UHFFFAOYSA-N 0.000 description 4
206010003130 Arrhythmia supraventricular Diseases 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
125000004744 butyloxycarbonyl group Chemical group 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
210000003540 papillary muscle Anatomy 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
230000000638 stimulation Effects 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
230000006794 tachycardia Effects 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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 3
239000002202 Polyethylene glycol Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
206010003668 atrial tachycardia Diseases 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000008101 lactose Substances 0.000 description 3
MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 3
229910001486 lithium perchlorate Inorganic materials 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000829 suppository Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
206010003658 Atrial Fibrillation Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
206010042434 Sudden death Diseases 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000018452 Torsade de pointes Diseases 0.000 description 2
208000002363 Torsades de Pointes Diseases 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
206010044565 Tremor Diseases 0.000 description 2
206010047281 Ventricular arrhythmia Diseases 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229950004210 cromakalim Drugs 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 2
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
210000002837 heart atrium Anatomy 0.000 description 2
239000001863 hydroxypropyl cellulose Substances 0.000 description 2
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 2
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
210000005246 left atrium Anatomy 0.000 description 2
229940057995 liquid paraffin Drugs 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 2
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 2
125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
239000006187 pill Substances 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
229950008882 polysorbate Drugs 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007901 soft capsule Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
229960002370 sotalol Drugs 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
206010047302 ventricular tachycardia Diseases 0.000 description 2
239000003871 white petrolatum Substances 0.000 description 2
NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
229940058015 1,3-butylene glycol Drugs 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
CKLFJWXRWIQYOC-UHFFFAOYSA-N 2-(4-fluorophenyl)ethanamine Chemical compound NCCC1=CC=C(F)C=C1 CKLFJWXRWIQYOC-UHFFFAOYSA-N 0.000 description 1
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 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
150000005168 4-hydroxybenzoic acids Chemical class 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 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
206010002091 Anaesthesia Diseases 0.000 description 1
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
229920002261 Corn starch 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
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
208000005189 Embolism Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
102100020870 La-related protein 6 Human genes 0.000 description 1
108050008265 La-related protein 6 Proteins 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 description 1
XHZONIFTGSYGGE-UXHICEINSA-N N-[(3S,4R)-3-hydroxy-2,2-dimethyl-7-nitro-4-(2-phenylethylamino)-3,4-dihydrochromen-6-yl]acetamide Chemical compound C(C)(=O)NC=1C(=CC2=C([C@H]([C@@H](C(O2)(C)C)O)NCCC2=CC=CC=C2)C=1)[N+](=O)[O-] XHZONIFTGSYGGE-UXHICEINSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
208000003734 Supraventricular Tachycardia Diseases 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000002763 arrhythmic effect Effects 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
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 1
239000011230 binding agent Substances 0.000 description 1
235000019437 butane-1,3-diol Nutrition 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
125000006251 butylcarbonyl group Chemical group 0.000 description 1
239000011575 calcium Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
230000008602 contraction Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000006437 ethyl cyclopropyl group Chemical group 0.000 description 1
229960001617 ethyl hydroxybenzoate Drugs 0.000 description 1
235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 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
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000008311 hydrophilic ointment Substances 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)C([H])([H])[H] 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 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
150000007517 lewis acids Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229940049920 malate Drugs 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000001525 mentha piperita l. herb oil Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
OGUSVMMCBOFCIO-UHFFFAOYSA-N n-(2,2-dimethyl-5-nitro-1a,7b-dihydrooxireno[2,3-c]chromen-6-yl)acetamide Chemical compound C12OC2C(C)(C)OC2=C1C=C(NC(=O)C)C([N+]([O-])=O)=C2 OGUSVMMCBOFCIO-UHFFFAOYSA-N 0.000 description 1
NHNCLBFWZWXLSJ-RTWAWAEBSA-N n-[(3s,4r)-3-hydroxy-2,2-dimethyl-7-nitro-4-(3-phenylpropylamino)-3,4-dihydrochromen-6-yl]acetamide Chemical compound N([C@@H]1C=2C=C(C(=CC=2OC(C)(C)[C@H]1O)[N+]([O-])=O)NC(=O)C)CCCC1=CC=CC=C1 NHNCLBFWZWXLSJ-RTWAWAEBSA-N 0.000 description 1
MDZLUBQTHDLOCE-YADHBBJMSA-N n-[(3s,4r)-3-hydroxy-2,2-dimethyl-7-nitro-4-(4-phenylbutylamino)-3,4-dihydrochromen-6-yl]acetamide Chemical compound N([C@@H]1C=2C=C(C(=CC=2OC(C)(C)[C@H]1O)[N+]([O-])=O)NC(=O)C)CCCCC1=CC=CC=C1 MDZLUBQTHDLOCE-YADHBBJMSA-N 0.000 description 1
FWUJNOYGOHKQOJ-UXHICEINSA-N n-[(3s,4r)-3-hydroxy-2,2-dimethyl-7-nitro-4-[2-(4-nitrophenyl)ethylamino]-3,4-dihydrochromen-6-yl]acetamide Chemical compound N([C@@H]1C=2C=C(C(=CC=2OC(C)(C)[C@H]1O)[N+]([O-])=O)NC(=O)C)CCC1=CC=C([N+]([O-])=O)C=C1 FWUJNOYGOHKQOJ-UXHICEINSA-N 0.000 description 1
WZOMMAWHOSUUAP-RTWAWAEBSA-N n-[(3s,4r)-3-hydroxy-4-[2-(4-methoxyphenyl)ethylamino]-2,2-dimethyl-7-nitro-3,4-dihydrochromen-6-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CCN[C@@H]1C2=CC(NC(C)=O)=C([N+]([O-])=O)C=C2OC(C)(C)[C@H]1O WZOMMAWHOSUUAP-RTWAWAEBSA-N 0.000 description 1
XIBBYUDIUCZWRV-UXHICEINSA-N n-[(3s,4r)-4-[2-(4-aminophenyl)ethylamino]-3-hydroxy-2,2-dimethyl-7-nitro-3,4-dihydrochromen-6-yl]acetamide Chemical compound N([C@@H]1C=2C=C(C(=CC=2OC(C)(C)[C@H]1O)[N+]([O-])=O)NC(=O)C)CCC1=CC=C(N)C=C1 XIBBYUDIUCZWRV-UXHICEINSA-N 0.000 description 1
PZFCWOZJJHSBDF-UXHICEINSA-N n-[(3s,4r)-4-[2-(4-chlorophenyl)ethylamino]-3-hydroxy-2,2-dimethyl-7-nitro-3,4-dihydrochromen-6-yl]acetamide Chemical compound N([C@@H]1C=2C=C(C(=CC=2OC(C)(C)[C@H]1O)[N+]([O-])=O)NC(=O)C)CCC1=CC=C(Cl)C=C1 PZFCWOZJJHSBDF-UXHICEINSA-N 0.000 description 1
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
229920001206 natural gum Polymers 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
125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001314 paroxysmal effect Effects 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
235000019477 peppermint oil Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000005561 phenanthryl group Chemical group 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229940051841 polyoxyethylene ether Drugs 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
238000004393 prognosis Methods 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
150000004671 saturated fatty acids Chemical class 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
230000035945 sensitivity Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
229940082004 sodium laurate Drugs 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical class C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)

SK329-2002A 1999-09-17 2000-09-14 Benzopyran derivative SK3292002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP26445599		1999-09-17
PCT/JP2000/006323 WO2001021610A1 (en)	1999-09-17	2000-09-14	Benzopyran derivative

Publications (1)

Publication Number	Publication Date
SK3292002A3 true SK3292002A3 (en)	2003-04-01

Family

ID=17403453

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK329-2002A SK3292002A3 (en)	1999-09-17	2000-09-14	Benzopyran derivative

Country Status (17)

Country	Link
US (1)	US6589983B1 (de)
EP (1)	EP1212314B1 (de)
KR (1)	KR100766676B1 (de)
CN (1)	CN1167697C (de)
AT (1)	ATE311378T1 (de)
AU (1)	AU766935B2 (de)
CA (1)	CA2383583C (de)
CZ (1)	CZ2002802A3 (de)
DE (1)	DE60024471T2 (de)
HK (1)	HK1047106B (de)
HU (1)	HUP0202690A3 (de)
IL (2)	IL147968A0 (de)
NO (1)	NO328013B1 (de)
NZ (1)	NZ517404A (de)
RU (1)	RU2234502C2 (de)
SK (1)	SK3292002A3 (de)
WO (1)	WO2001021610A1 (de)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW589305B (en) *	2001-02-14	2004-06-01	Nissan Chemical Ind Ltd	4-aminobenzopyran derivatives
FI20011507A0 (fi)	2001-07-10	2001-07-10	Orion Corp	Uusia yhdisteitä
EP1432696A1 (de) *	2001-10-04	2004-06-30	Wyeth	Chromanderivate als 5-hydroxytryptamin-6-liganden
ES2353383T3 (es) *	2002-08-29	2011-03-01	Nissan Chemical Industries, Ltd.	Procedimiento de producción de un compuesto de aminobenzopirano.
FI20030030A0 (fi) *	2003-01-09	2003-01-09	Orion Corp	Uusia yhdisteitä
GB0315950D0 (en)	2003-06-11	2003-08-13	Xention Discovery Ltd	Compounds
TWI346112B (en)	2004-02-25	2011-08-01	Nissan Chemical Ind Ltd	Benzopyran compound
JP4840594B2 (ja)	2004-03-23	2011-12-21	日産化学工業株式会社	抗不整脈薬としての３環性ベンゾピラン化合物
GB0412986D0 (en)	2004-06-10	2004-07-14	Xention Discovery Ltd	Compounds
US7576212B2 (en)	2004-12-09	2009-08-18	Xention Limited	Thieno[2,3-B] pyridines as potassium channel inhibitors
WO2006066756A1 (en) *	2004-12-21	2006-06-29	F. Hoffmann-La Roche Ag	Chroman derivatives and uses thereof in the treatment of cns disorders
GB0525164D0 (en)	2005-12-09	2006-01-18	Xention Discovery Ltd	Compounds
US8394974B2 (en) *	2006-03-10	2013-03-12	Nissan Chemical Industries, Ltd.	Process for producing optically active chromene oxide compound
GB0815784D0 (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
GB0815782D0 (en)	2008-08-29	2008-10-08	Xention Ltd	Novel potassium channel blockers
US20130109019A1 (en) *	2010-07-02	2013-05-02	Adrian E. Murillo	Hapten conjugates for target detection
GB201105659D0 (en)	2011-04-01	2011-05-18	Xention Ltd	Compounds
NO3175985T3 (de)	2011-07-01	2018-04-28
AR090037A1 (es)	2011-11-15	2014-10-15	Xention Ltd	Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio
JP2014533258A (ja)	2011-11-15	2014-12-11	ゼンション・リミテッドＸｅｎｔｉｏｎＬｉｍｉｔｅｄ	カリウムチャネル阻害剤としてのチエノ［２，３−ｃ］ピラゾールの使用
JP2015504923A (ja)	2012-01-27	2015-02-16	ギリアードサイエンシーズ，インコーポレイテッド	後期ナトリウムイオンチャネル遮断剤およびカリウムイオンチャネル遮断剤を使用する併用療法
CN113543849B (zh)	2018-12-28	2025-03-21	国立大学法人大阪大学	遗传性缓慢性心律失常治疗药

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9005318D0 (en)	1990-03-09	1990-05-02	Isis Innovation	Antiarrhythmic agents
AU651105B2 (en) *	1990-06-18	1994-07-14	E.R. Squibb & Sons, Inc.	Benzopyran derivatives and heterocyclic analogs thereof as antiischemic agents
GB9301611D0 (en) *	1993-08-04	1993-08-04	Parisella Gerald	Dexterity game
NZ333870A (en) *	1996-07-26	2000-08-25	Nissan Chemical Ind Ltd	4-amino substituted chroman derivatives

2000
- 2000-09-14 WO PCT/JP2000/006323 patent/WO2001021610A1/en not_active Ceased
- 2000-09-14 RU RU2002110115/04A patent/RU2234502C2/ru not_active IP Right Cessation
- 2000-09-14 AU AU73143/00A patent/AU766935B2/en not_active Ceased
- 2000-09-14 CA CA002383583A patent/CA2383583C/en not_active Expired - Fee Related
- 2000-09-14 CZ CZ2002802A patent/CZ2002802A3/cs unknown
- 2000-09-14 NZ NZ517404A patent/NZ517404A/xx unknown
- 2000-09-14 SK SK329-2002A patent/SK3292002A3/sk unknown
- 2000-09-14 US US10/048,026 patent/US6589983B1/en not_active Expired - Fee Related
- 2000-09-14 EP EP00961032A patent/EP1212314B1/de not_active Expired - Lifetime
- 2000-09-14 HU HU0202690A patent/HUP0202690A3/hu unknown
- 2000-09-14 KR KR1020027003510A patent/KR100766676B1/ko not_active Expired - Fee Related
- 2000-09-14 IL IL14796800A patent/IL147968A0/xx active IP Right Grant
- 2000-09-14 CN CNB008129509A patent/CN1167697C/zh not_active Expired - Fee Related
- 2000-09-14 DE DE60024471T patent/DE60024471T2/de not_active Expired - Lifetime
- 2000-09-14 HK HK02108750.1A patent/HK1047106B/en not_active IP Right Cessation
- 2000-09-14 AT AT00961032T patent/ATE311378T1/de not_active IP Right Cessation
2002
- 2002-02-03 IL IL147968A patent/IL147968A/en not_active IP Right Cessation
- 2002-03-15 NO NO20021294A patent/NO328013B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
NZ517404A (en)	2003-01-31
NO20021294D0 (no)	2002-03-15
KR100766676B1 (ko)	2007-10-15
CN1167697C (zh)	2004-09-22
KR20020068505A (ko)	2002-08-27
US6589983B1 (en)	2003-07-08
NO20021294L (no)	2002-03-15
WO2001021610A1 (en)	2001-03-29
EP1212314A1 (de)	2002-06-12
CZ2002802A3 (cs)	2003-02-12
CN1374957A (zh)	2002-10-16
DE60024471T2 (de)	2006-08-03
CA2383583A1 (en)	2001-03-29
HK1047106B (en)	2006-04-28
NO328013B1 (no)	2009-11-09
DE60024471D1 (de)	2006-01-05
ATE311378T1 (de)	2005-12-15
AU766935B2 (en)	2003-10-23
HUP0202690A2 (hu)	2002-12-28
HK1047106A1 (en)	2003-02-07
EP1212314B1 (de)	2005-11-30
AU7314300A (en)	2001-04-24
IL147968A (en)	2006-04-10
CA2383583C (en)	2009-04-07
HUP0202690A3 (en)	2005-02-28
RU2234502C2 (ru)	2004-08-20
IL147968A0 (en)	2002-09-12

Legal Events

Date	Code	Title	Description
2011-03-04	FD9A	Suspended procedure due to non-payment of fee

Publication	Publication Date	Title
US6589983B1 (en)	2003-07-08	Benzopyran derivative
RU2291867C2 (ru)	2007-01-20	Замещенные производные бензопирана против аритмии
US6555574B1 (en)	2003-04-29	4-oxybenzopyran derivative
US6677371B1 (en)	2004-01-13	4-oxybenzopyran derivative
RU2366658C2 (ru)	2009-09-10	Бензопирановое соединение
JP2001151767A (ja)	2001-06-05	ベンゾピラン誘導体
JP4386159B2 (ja)	2009-12-16	置換ベンゾピラン誘導体
JP2001172275A (ja)	2001-06-26	４−オキシベンゾピラン誘導体
JP2001158780A (ja)	2001-06-12	４−オキシベンゾピラン誘導体
AU2002309284A1 (en)	2003-01-08	Substituted benzopyran derivatives against arrhythmia
HK1063785B (en)	2006-04-07	Substituted benzopyran derivatives against arrhythmia