LT4578B - Chromano dariniai - Google Patents
Chromano dariniai Download PDFInfo
- Publication number
- LT4578B LT4578B LT99-017A LT99017A LT4578B LT 4578 B LT4578 B LT 4578B LT 99017 A LT99017 A LT 99017A LT 4578 B LT4578 B LT 4578B
- Authority
- LT
- Lithuania
- Prior art keywords
- group
- substituted
- alkyl
- unsubstituted
- aryl
- Prior art date
Links
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 98
- 125000005843 halogen group Chemical group 0.000 claims abstract description 81
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 80
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 69
- 150000003839 salts Chemical class 0.000 claims abstract description 59
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 38
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 27
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 18
- -1 C 6 alkoxy group Chemical group 0.000 claims description 295
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 143
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 120
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 86
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 56
- 125000000217 alkyl group Chemical class 0.000 claims description 52
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 125000003545 alkoxy group Chemical class 0.000 claims description 44
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 31
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 229940079593 drug Drugs 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 17
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000003282 alkyl amino group Chemical class 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 10
- 206010019280 Heart failures Diseases 0.000 claims description 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 8
- 125000000383 tetramethylene group Chemical class [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 8
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 7
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- ZIPLUEXSCPLCEI-UHFFFAOYSA-N cyanamide group Chemical group C(#N)[NH-] ZIPLUEXSCPLCEI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 290
- 238000005481 NMR spectroscopy Methods 0.000 description 125
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 118
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 239000002904 solvent Substances 0.000 description 64
- 238000006243 chemical reaction Methods 0.000 description 58
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 55
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 27
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 27
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 235000019441 ethanol Nutrition 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 239000002585 base Substances 0.000 description 19
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 19
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 19
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 18
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 14
- 150000003462 sulfoxides Chemical class 0.000 description 14
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 13
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 238000009835 boiling Methods 0.000 description 13
- 150000002170 ethers Chemical class 0.000 description 13
- 239000012442 inert solvent Substances 0.000 description 13
- 239000000376 reactant Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 10
- 239000003849 aromatic solvent Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000007810 chemical reaction solvent Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 6
- 239000000829 suppository Substances 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 210000004165 myocardium Anatomy 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 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 5
- 239000002674 ointment Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- ZGROZVHFENRYAI-UHFFFAOYSA-N n-(2,2-dimethyl-7-nitrochromen-6-yl)benzamide Chemical compound C1=C2C=CC(C)(C)OC2=CC([N+]([O-])=O)=C1NC(=O)C1=CC=CC=C1 ZGROZVHFENRYAI-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000001562 benzopyrans Chemical class 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- QKLSFAVXZOMRGP-UHFFFAOYSA-N n-(2,2-dimethyl-5-nitro-1a,7b-dihydrooxireno[2,3-c]chromen-6-yl)benzamide Chemical compound C1=C2C3OC3C(C)(C)OC2=CC([N+]([O-])=O)=C1NC(=O)C1=CC=CC=C1 QKLSFAVXZOMRGP-UHFFFAOYSA-N 0.000 description 3
- DTXJMMCSCCMLLB-UHFFFAOYSA-N n-(3-bromo-4-hydroxy-2,2-dimethyl-7-nitro-3,4-dihydrochromen-6-yl)benzamide Chemical compound C1=C2C(O)C(Br)C(C)(C)OC2=CC([N+]([O-])=O)=C1NC(=O)C1=CC=CC=C1 DTXJMMCSCCMLLB-UHFFFAOYSA-N 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JSPQBFOFUCKECH-UHFFFAOYSA-N (3-amino-2,2-dimethyl-7-nitrochromen-6-yl)-(4-hydroxyphenyl)methanone Chemical compound OC1=CC=C(C(=O)C=2C(=CC3=C(C=C(C(O3)(C)C)N)C=2)[N+](=O)[O-])C=C1 JSPQBFOFUCKECH-UHFFFAOYSA-N 0.000 description 2
- RECCURWJDVZHIH-UHFFFAOYSA-N (4-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=C(Cl)C=C1 RECCURWJDVZHIH-UHFFFAOYSA-N 0.000 description 2
- SRYLJBWDZZMDSK-UHFFFAOYSA-N (4-methoxyphenyl)thiourea Chemical compound COC1=CC=C(NC(N)=S)C=C1 SRYLJBWDZZMDSK-UHFFFAOYSA-N 0.000 description 2
- BLYAANPIHFKKMQ-UHFFFAOYSA-N (4-nitrophenyl)thiourea Chemical compound NC(=S)NC1=CC=C([N+]([O-])=O)C=C1 BLYAANPIHFKKMQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- WROPMDUJGWMIFK-UHFFFAOYSA-N 2,2-dimethyl-5-nitro-1a,7b-dihydrooxireno[2,3-c]chromen-6-amine Chemical compound CC1(C)OC2=CC([N+]([O-])=O)=C(N)C=C2C2C1O2 WROPMDUJGWMIFK-UHFFFAOYSA-N 0.000 description 2
- OMQAQIYAMSIFEK-UHFFFAOYSA-N 2,2-dimethyl-7-nitrochromen-6-amine Chemical compound [O-][N+](=O)C1=C(N)C=C2C=CC(C)(C)OC2=C1 OMQAQIYAMSIFEK-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- 239000000305 astragalus gummifer gum Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 description 2
- UCGFRIAOVLXVKL-UHFFFAOYSA-N benzylthiourea Chemical compound NC(=S)NCC1=CC=CC=C1 UCGFRIAOVLXVKL-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000000059 bradycardiac effect Effects 0.000 description 2
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 230000002057 chronotropic effect Effects 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
- 238000010511 deprotection reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012153 distilled water Substances 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
- 238000009472 formulation Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- LMYQWQCDUHNQLF-UHFFFAOYSA-N hexylthiourea Chemical compound CCCCCCNC(N)=S LMYQWQCDUHNQLF-UHFFFAOYSA-N 0.000 description 2
- JUVJQIPDVWOVNP-UHFFFAOYSA-N hexylurea Chemical compound CCCCCCNC(N)=O JUVJQIPDVWOVNP-UHFFFAOYSA-N 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229940039009 isoproterenol Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- GCBFSBLOISBTGE-UHFFFAOYSA-N n-(2,2-dimethyl-5-nitro-1a,7b-dihydrooxireno[2,3-c]chromen-6-yl)-2-(4-phenylphenyl)acetamide Chemical compound C1=C2C3OC3C(C)(C)OC2=CC([N+]([O-])=O)=C1NC(=O)CC(C=C1)=CC=C1C1=CC=CC=C1 GCBFSBLOISBTGE-UHFFFAOYSA-N 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 2
- 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 2
- MONRWRVYLOHUFA-UHFFFAOYSA-N pentylurea Chemical compound CCCCCNC(N)=O MONRWRVYLOHUFA-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000007901 soft capsule Substances 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
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 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
- YDAKEVOYUPFWFX-UHFFFAOYSA-N (2-methylphenyl)methylthiourea Chemical compound CC1=CC=CC=C1CNC(N)=S YDAKEVOYUPFWFX-UHFFFAOYSA-N 0.000 description 1
- BLSVCHHBHKGCSQ-UHFFFAOYSA-N (2-methylphenyl)urea Chemical compound CC1=CC=CC=C1NC(N)=O BLSVCHHBHKGCSQ-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- CRHPDONOCLCOOR-UHFFFAOYSA-N (4-chlorophenyl)methylthiourea Chemical compound NC(=S)NCC1=CC=C(Cl)C=C1 CRHPDONOCLCOOR-UHFFFAOYSA-N 0.000 description 1
- XVEFWRUIYOXUGG-UHFFFAOYSA-N (4-chlorophenyl)thiourea Chemical compound NC(=S)NC1=CC=C(Cl)C=C1 XVEFWRUIYOXUGG-UHFFFAOYSA-N 0.000 description 1
- WIYSPOVJUBYXBI-UHFFFAOYSA-N (4-cyanophenyl)methylurea Chemical compound NC(=O)NCC1=CC=C(C#N)C=C1 WIYSPOVJUBYXBI-UHFFFAOYSA-N 0.000 description 1
- UZJXXZZIIAZHAL-UHFFFAOYSA-N (4-fluorophenyl)methylthiourea Chemical compound NC(=S)NCC1=CC=C(F)C=C1 UZJXXZZIIAZHAL-UHFFFAOYSA-N 0.000 description 1
- ISIFPVOJHJASJW-UHFFFAOYSA-N (4-fluorophenyl)methylurea Chemical compound NC(=O)NCC1=CC=C(F)C=C1 ISIFPVOJHJASJW-UHFFFAOYSA-N 0.000 description 1
- IQZBVVPYTDHTIP-UHFFFAOYSA-N (4-fluorophenyl)urea Chemical compound NC(=O)NC1=CC=C(F)C=C1 IQZBVVPYTDHTIP-UHFFFAOYSA-N 0.000 description 1
- UNZSYIMZOJHWNX-UHFFFAOYSA-N (4-methylphenyl)methylthiourea Chemical compound CC1=CC=C(CNC(N)=S)C=C1 UNZSYIMZOJHWNX-UHFFFAOYSA-N 0.000 description 1
- CWQOSUOSPHUYTM-UHFFFAOYSA-N (4-methylphenyl)methylurea Chemical compound CC1=CC=C(CNC(N)=O)C=C1 CWQOSUOSPHUYTM-UHFFFAOYSA-N 0.000 description 1
- JTVLKCKOMVXJQH-UHFFFAOYSA-N (4-nitrophenyl)methylurea Chemical compound NC(=O)NCC1=CC=C([N+]([O-])=O)C=C1 JTVLKCKOMVXJQH-UHFFFAOYSA-N 0.000 description 1
- LXXTVGKSGJADFU-UHFFFAOYSA-N (4-nitrophenyl)urea Chemical compound NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 LXXTVGKSGJADFU-UHFFFAOYSA-N 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- VZOPVKZLLGMDDG-UHFFFAOYSA-N 1-oxido-4-phenylpyridin-1-ium Chemical compound C1=C[N+]([O-])=CC=C1C1=CC=CC=C1 VZOPVKZLLGMDDG-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
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- BTEJBMQXKFTAJI-UHFFFAOYSA-N 2,2-dimethylpropylthiourea Chemical compound CC(C)(C)CNC(N)=S BTEJBMQXKFTAJI-UHFFFAOYSA-N 0.000 description 1
- XTNMUWVPABAFRL-UHFFFAOYSA-N 2,2-dimethylpropylurea Chemical compound CC(C)(C)CNC(N)=O XTNMUWVPABAFRL-UHFFFAOYSA-N 0.000 description 1
- MRWHUNCOQKBNKR-UHFFFAOYSA-N 2,3-dimethylbutan-2-ylurea Chemical compound CC(C)C(C)(C)NC(N)=O MRWHUNCOQKBNKR-UHFFFAOYSA-N 0.000 description 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
- HVHZEKKZMFRULH-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylpyridine Chemical compound CC1=CC(C(C)(C)C)=NC(C(C)(C)C)=C1 HVHZEKKZMFRULH-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- KQGHTOZUPICELS-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]acetic acid Chemical compound CN(C)C1=CC=C(CC(O)=O)C=C1 KQGHTOZUPICELS-UHFFFAOYSA-N 0.000 description 1
- OQCRARVMZPCWNM-UHFFFAOYSA-N 2-chloro-n-(2,2-dimethyl-7-nitrochromen-6-yl)acetamide Chemical compound [O-][N+](=O)C1=C(NC(=O)CCl)C=C2C=CC(C)(C)OC2=C1 OQCRARVMZPCWNM-UHFFFAOYSA-N 0.000 description 1
- WYVNTUOOQQICLA-UHFFFAOYSA-N 2-methylbutan-2-ylthiourea Chemical compound CCC(C)(C)NC(N)=S WYVNTUOOQQICLA-UHFFFAOYSA-N 0.000 description 1
- OVUWGANMOQIFHZ-UHFFFAOYSA-N 2-methylbutan-2-ylurea Chemical compound CCC(C)(C)NC(N)=O OVUWGANMOQIFHZ-UHFFFAOYSA-N 0.000 description 1
- RGTMILHZLXZRGF-UHFFFAOYSA-N 2-methylpropylthiourea Chemical compound CC(C)CNC(N)=S RGTMILHZLXZRGF-UHFFFAOYSA-N 0.000 description 1
- LKXADRQJLNYNQL-UHFFFAOYSA-N 2h-chromen-3-ol Chemical compound C1=CC=C2OCC(O)=CC2=C1 LKXADRQJLNYNQL-UHFFFAOYSA-N 0.000 description 1
- ZYGVZNIJABPMQM-UHFFFAOYSA-N 3,3-dimethylbutan-2-ylthiourea Chemical compound CC(C)(C)C(C)NC(N)=S ZYGVZNIJABPMQM-UHFFFAOYSA-N 0.000 description 1
- CANRFNSRGCDLCS-UHFFFAOYSA-N 3,3-dimethylbutan-2-ylurea Chemical compound CC(C)(C)C(C)NC(N)=O CANRFNSRGCDLCS-UHFFFAOYSA-N 0.000 description 1
- CSPHEIRDIXSNAO-UHFFFAOYSA-N 3,3-dimethylbutylthiourea Chemical compound CC(C)(C)CCNC(N)=S CSPHEIRDIXSNAO-UHFFFAOYSA-N 0.000 description 1
- IUCPQMWUBBCJQN-UHFFFAOYSA-N 3,3-dimethylbutylurea Chemical compound CC(C)(C)CCNC(N)=O IUCPQMWUBBCJQN-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- PIVQQUNOTICCSA-UHFFFAOYSA-N ANTU Chemical group C1=CC=C2C(NC(=S)N)=CC=CC2=C1 PIVQQUNOTICCSA-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
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 1
- DTFBYUNKTKRVOE-UHFFFAOYSA-N CCC(C=C1)=CC=C1OC.I Chemical compound CCC(C=C1)=CC=C1OC.I DTFBYUNKTKRVOE-UHFFFAOYSA-N 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 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
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 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
- POXAIQSXNOEQGM-UHFFFAOYSA-N Isopropylthioharnstoff Natural products CC(C)NC(N)=S POXAIQSXNOEQGM-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- UHGKYJXJYJWDAM-UHFFFAOYSA-N Propylthiourea Chemical compound CCCNC(N)=S UHGKYJXJYJWDAM-UHFFFAOYSA-N 0.000 description 1
- 206010037423 Pulmonary oedema Diseases 0.000 description 1
- 230000010757 Reduction Activity Effects 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 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
- 241000776475 Terrabacteria group Species 0.000 description 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 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
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- RJNJWHFSKNJCTB-UHFFFAOYSA-N benzylurea Chemical compound NC(=O)NCC1=CC=CC=C1 RJNJWHFSKNJCTB-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
- 230000037396 body weight Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- CBRSBDUOPJQVMP-UHFFFAOYSA-N butan-2-ylurea Chemical compound CCC(C)NC(N)=O CBRSBDUOPJQVMP-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000007963 capsule composition Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000022900 cardiac muscle contraction Effects 0.000 description 1
- 230000003177 cardiotonic effect Effects 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
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001844 chromium Chemical class 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
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch 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
- 230000001419 dependent effect Effects 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000003255 drug test Methods 0.000 description 1
- 230000037024 effective refractory period Effects 0.000 description 1
- 150000002148 esters Chemical class 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
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VIRPEGDUZPJZAG-UHFFFAOYSA-N formyl(hydroxy)carbamic acid Chemical compound O=CN(O)C(O)=O VIRPEGDUZPJZAG-UHFFFAOYSA-N 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
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 230000010247 heart contraction Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- CYMUIXDPMCIPKU-UHFFFAOYSA-N hexan-2-ylurea Chemical compound CCCCC(C)NC(N)=O CYMUIXDPMCIPKU-UHFFFAOYSA-N 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 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
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- SQKIZTPMVWJSLG-UHFFFAOYSA-N n-(2,2-dimethyl-5-nitro-1a,7b-dihydrooxireno[2,3-c]chromen-6-yl)-2-phenylacetamide Chemical compound C1=C2C3OC3C(C)(C)OC2=CC([N+]([O-])=O)=C1NC(=O)CC1=CC=CC=C1 SQKIZTPMVWJSLG-UHFFFAOYSA-N 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
- ZMAIELQHCRNNHF-UXHICEINSA-N n-[(3s,4r)-3-hydroxy-2,2-dimethyl-7-nitro-4-pyrrolidin-1-yl-3,4-dihydrochromen-6-yl]benzamide Chemical compound CC([C@H]([C@@H](C1=C2)N3CCCC3)O)(C)OC1=CC([N+]([O-])=O)=C2NC(=O)C1=CC=CC=C1 ZMAIELQHCRNNHF-UXHICEINSA-N 0.000 description 1
- SFMJNHNUOVADRW-UHFFFAOYSA-N n-[5-[9-[4-(methanesulfonamido)phenyl]-2-oxobenzo[h][1,6]naphthyridin-1-yl]-2-methylphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(C)=CC=C1N1C(=O)C=CC2=C1C1=CC(C=3C=CC(NS(C)(=O)=O)=CC=3)=CC=C1N=C2 SFMJNHNUOVADRW-UHFFFAOYSA-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
- VOXMFTOMEDWLAD-UHFFFAOYSA-N naphthalen-2-ylmethylthiourea Chemical compound C1=CC=CC2=CC(CNC(=S)N)=CC=C21 VOXMFTOMEDWLAD-UHFFFAOYSA-N 0.000 description 1
- CLBBRKDGXBLABM-UHFFFAOYSA-N naphthalen-2-ylmethylurea Chemical compound C1=CC=CC2=CC(CNC(=O)N)=CC=C21 CLBBRKDGXBLABM-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- ACLZYRNSDLQOIA-UHFFFAOYSA-N o-tolylthiourea Chemical compound CC1=CC=CC=C1NC(N)=S ACLZYRNSDLQOIA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- KIYXXKTUEPCNLC-UHFFFAOYSA-N pentylthiourea Chemical compound CCCCCNC(N)=S KIYXXKTUEPCNLC-UHFFFAOYSA-N 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
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000006247 phenyl propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006308 propyl amino group Chemical group 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
- 208000005333 pulmonary edema Diseases 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 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
- 238000001228 spectrum Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000007916 tablet composition Substances 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
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- YNBQAYKYNYRCCA-UHFFFAOYSA-N venadaparib Chemical compound C1(CC1)NCC1CN(C1)C(=O)C=1C=C(CC2=NNC(C3=CC=CC=C23)=O)C=CC1F YNBQAYKYNYRCCA-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- 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
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19781996 | 1996-07-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LT99017A LT99017A (en) | 1999-07-26 |
| LT4578B true LT4578B (lt) | 1999-11-25 |
Family
ID=16380875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LT99-017A LT4578B (lt) | 1996-07-26 | 1999-02-23 | Chromano dariniai |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6066631A (zh) |
| EP (1) | EP0934296B1 (zh) |
| KR (1) | KR20000023843A (zh) |
| CN (1) | CN1226243A (zh) |
| AT (1) | ATE242230T1 (zh) |
| AU (1) | AU713573B2 (zh) |
| CA (1) | CA2261143A1 (zh) |
| CZ (1) | CZ24499A3 (zh) |
| DE (1) | DE69722644T2 (zh) |
| HU (1) | HUP9902456A3 (zh) |
| IL (1) | IL128170A0 (zh) |
| LT (1) | LT4578B (zh) |
| NO (1) | NO990265L (zh) |
| NZ (1) | NZ333870A (zh) |
| SK (1) | SK7599A3 (zh) |
| TW (1) | TW491844B (zh) |
| WO (1) | WO1998004542A1 (zh) |
| ZA (1) | ZA976654B (zh) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP9902456A3 (en) * | 1996-07-26 | 2002-04-29 | Nissan Chemical Ind Ltd | Chroman derivatives |
| DE19730989A1 (de) | 1997-07-18 | 1999-01-21 | Merck Patent Gmbh | Piperazin-Derivate |
| EP1085009B1 (en) * | 1998-06-03 | 2004-11-10 | Nissan Chemical Industries, Ltd. | Indan derivatives |
| HUP0202690A3 (en) * | 1999-09-17 | 2005-02-28 | Nissan Chemical Ind Ltd | Benzopyran derivative having antiarrhytmic activity |
| GB0315950D0 (en) | 2003-06-11 | 2003-08-13 | Xention Discovery Ltd | Compounds |
| WO2005037830A1 (en) | 2003-10-10 | 2005-04-28 | Wyeth | Piperidinylchromen-6-ylsulfonamide compounds as 5-hydroxytryptamine-6 ligands |
| TWI346112B (en) | 2004-02-25 | 2011-08-01 | Nissan Chemical Ind Ltd | Benzopyran compound |
| 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 |
| GB0525164D0 (en) | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
| GB0815782D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815781D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB0815784D0 (en) | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| GB201105659D0 (en) | 2011-04-01 | 2011-05-18 | Xention Ltd | Compounds |
| NO3175985T3 (zh) | 2011-07-01 | 2018-04-28 | ||
| CA2862670A1 (en) | 2012-01-27 | 2013-08-01 | Gilead Sciences, Inc. | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS511477A (zh) | 1974-05-31 | 1976-01-08 | Beecham Group Ltd | |
| JPS5657786A (en) | 1979-09-28 | 1981-05-20 | Beecham Group Ltd | Chromanol derivative* its manufacture and medicinal composition containing it |
| JPS5657785A (en) | 1979-09-28 | 1981-05-20 | Beecham Group Ltd | Chromanol derivative* its manufacture and medicinal composition containing it |
| JPS5867683A (ja) | 1981-09-25 | 1983-04-22 | ビーチャム・グループ・ピーエルシー | 活性化合物、その製法およびそれを含む医薬組成物 |
| JPS58188880A (ja) | 1982-04-08 | 1983-11-04 | ビーチャム・グループ・ピーエルシー | ベンゾピラン誘導体、その製法及びそれを含む製薬組成物 |
| EP0157843A1 (en) | 1983-09-14 | 1985-10-16 | Beecham Group Plc | Antihypertensive pyrrylchromanes |
| EP0409165A2 (en) | 1989-07-17 | 1991-01-23 | Nissan Chemical Industries Ltd. | Process for the optical resolution of pyranobenzoxadiazole compounds |
| JPH03141286A (ja) | 1989-07-17 | 1991-06-17 | Nissan Chem Ind Ltd | 光学活性ピラノベンゾオキサジアゾール誘導体 |
| EP0535377A2 (en) | 1991-08-30 | 1993-04-07 | Nissan Chemical Industries Ltd. | Optically active benzopyran compound, process for producing it and optically active manganese complex |
| JPH05507645A (ja) | 1990-03-21 | 1993-11-04 | リサーチ コーポレイション テクノロジーズ インコーポレイテッド | キラル触媒及びそれにより触媒されたエポキシ化反応 |
| JPH05301878A (ja) | 1991-08-30 | 1993-11-16 | Nissan Chem Ind Ltd | 不斉エポキシ化反応 |
| JPH0728983A (ja) | 1993-07-07 | 1995-01-31 | Japan Radio Co Ltd | レーダ画像真位置計測装置 |
| US5420314A (en) | 1994-02-23 | 1995-05-30 | Nissan Chemical Industries, Ltd. | Asymmetric epoxidation reaction |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3064286D1 (en) * | 1979-09-28 | 1983-08-25 | Beecham Group Plc | Chromanol derivatives, a process for their preparation and a pharmaceutical composition comprising them |
| EP0093535B1 (en) * | 1982-04-28 | 1986-12-30 | Beecham Group Plc | Novel chromenes and chromans |
| JP2734457B2 (ja) * | 1994-02-23 | 1998-03-30 | 日産化学工業株式会社 | 不斉エポキシ化反応 |
| WO1997023209A1 (fr) * | 1995-12-25 | 1997-07-03 | Nissan Chemical Industries, Ltd. | Agent therapeutique contre l'insuffisance cardiaque |
| HUP9902456A3 (en) * | 1996-07-26 | 2002-04-29 | Nissan Chemical Ind Ltd | Chroman derivatives |
-
1997
- 1997-07-25 HU HU9902456A patent/HUP9902456A3/hu unknown
- 1997-07-25 AU AU36349/97A patent/AU713573B2/en not_active Ceased
- 1997-07-25 TW TW086110615A patent/TW491844B/zh active
- 1997-07-25 NZ NZ333870A patent/NZ333870A/xx unknown
- 1997-07-25 ZA ZA9706654A patent/ZA976654B/xx unknown
- 1997-07-25 AT AT97933023T patent/ATE242230T1/de not_active IP Right Cessation
- 1997-07-25 CN CN97196736A patent/CN1226243A/zh active Pending
- 1997-07-25 WO PCT/JP1997/002583 patent/WO1998004542A1/en not_active Application Discontinuation
- 1997-07-25 CA CA002261143A patent/CA2261143A1/en not_active Abandoned
- 1997-07-25 SK SK75-99A patent/SK7599A3/sk unknown
- 1997-07-25 CZ CZ99244A patent/CZ24499A3/cs unknown
- 1997-07-25 DE DE69722644T patent/DE69722644T2/de not_active Expired - Fee Related
- 1997-07-25 EP EP97933023A patent/EP0934296B1/en not_active Expired - Lifetime
- 1997-07-25 IL IL12817097A patent/IL128170A0/xx unknown
-
1999
- 1999-01-18 KR KR1019997000359A patent/KR20000023843A/ko not_active Application Discontinuation
- 1999-01-19 US US09/232,645 patent/US6066631A/en not_active Expired - Fee Related
- 1999-01-21 NO NO990265A patent/NO990265L/no not_active Application Discontinuation
- 1999-02-23 LT LT99-017A patent/LT4578B/lt not_active IP Right Cessation
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS511477A (zh) | 1974-05-31 | 1976-01-08 | Beecham Group Ltd | |
| JPS5657786A (en) | 1979-09-28 | 1981-05-20 | Beecham Group Ltd | Chromanol derivative* its manufacture and medicinal composition containing it |
| JPS5657785A (en) | 1979-09-28 | 1981-05-20 | Beecham Group Ltd | Chromanol derivative* its manufacture and medicinal composition containing it |
| JPS5867683A (ja) | 1981-09-25 | 1983-04-22 | ビーチャム・グループ・ピーエルシー | 活性化合物、その製法およびそれを含む医薬組成物 |
| JPS58188880A (ja) | 1982-04-08 | 1983-11-04 | ビーチャム・グループ・ピーエルシー | ベンゾピラン誘導体、その製法及びそれを含む製薬組成物 |
| EP0157843A1 (en) | 1983-09-14 | 1985-10-16 | Beecham Group Plc | Antihypertensive pyrrylchromanes |
| EP0409165A2 (en) | 1989-07-17 | 1991-01-23 | Nissan Chemical Industries Ltd. | Process for the optical resolution of pyranobenzoxadiazole compounds |
| JPH03141286A (ja) | 1989-07-17 | 1991-06-17 | Nissan Chem Ind Ltd | 光学活性ピラノベンゾオキサジアゾール誘導体 |
| US5097037A (en) | 1989-07-17 | 1992-03-17 | Nissan Chemical Industries, Ltd. | Process for the optical resolution of pyranobenzoxadiazole compounds |
| JPH05507645A (ja) | 1990-03-21 | 1993-11-04 | リサーチ コーポレイション テクノロジーズ インコーポレイテッド | キラル触媒及びそれにより触媒されたエポキシ化反応 |
| EP0535377A2 (en) | 1991-08-30 | 1993-04-07 | Nissan Chemical Industries Ltd. | Optically active benzopyran compound, process for producing it and optically active manganese complex |
| JPH05301878A (ja) | 1991-08-30 | 1993-11-16 | Nissan Chem Ind Ltd | 不斉エポキシ化反応 |
| JPH0728983A (ja) | 1993-07-07 | 1995-01-31 | Japan Radio Co Ltd | レーダ画像真位置計測装置 |
| US5420314A (en) | 1994-02-23 | 1995-05-30 | Nissan Chemical Industries, Ltd. | Asymmetric epoxidation reaction |
Non-Patent Citations (3)
| Title |
|---|
| ASHWOOD VA ET AL.: "Synthesis and antihypertensive activity of 4-(cyclic amido)-2H-1-benzopyrans", J MED CHEM., 1986, pages 2194, XP008050667, DOI: doi:10.1021/jm00161a011 |
| JEFFREY T. NORTH ET AL.: "Synthesis of 6-Cyano-2,2-dimethyl-2H-1-benzopyran and Other Substituted 2,2-Dimethyl-2H-1-benzopyrans", J. ORG. CHEM., 1995, pages 3397 - 3400 |
| JOHN M. EVANS ET AL.: "Synthesis and antihypertensive activity of 6,7-disubstituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols", J. MED. CHEM., 1984, pages 1127, XP002048426, DOI: doi:10.1021/jm00375a007 |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9902456A3 (en) | 2002-04-29 |
| SK7599A3 (en) | 1999-07-12 |
| HUP9902456A2 (hu) | 2001-05-28 |
| WO1998004542A1 (en) | 1998-02-05 |
| US6066631A (en) | 2000-05-23 |
| CN1226243A (zh) | 1999-08-18 |
| NO990265L (no) | 1999-03-25 |
| EP0934296B1 (en) | 2003-06-04 |
| TW491844B (en) | 2002-06-21 |
| ZA976654B (en) | 1998-02-10 |
| DE69722644T2 (de) | 2004-05-06 |
| CA2261143A1 (en) | 1998-02-05 |
| CZ24499A3 (cs) | 1999-05-12 |
| ATE242230T1 (de) | 2003-06-15 |
| AU713573B2 (en) | 1999-12-02 |
| NZ333870A (en) | 2000-08-25 |
| IL128170A0 (en) | 1999-11-30 |
| NO990265D0 (no) | 1999-01-21 |
| AU3634997A (en) | 1998-02-20 |
| KR20000023843A (ko) | 2000-04-25 |
| LT99017A (en) | 1999-07-26 |
| DE69722644D1 (de) | 2003-07-10 |
| EP0934296A1 (en) | 1999-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| LT4578B (lt) | Chromano dariniai | |
| JP5057273B2 (ja) | イソインドリン−１−ワン誘導体 | |
| US9676713B2 (en) | Crystal of pyrrole derivative and method for producing the same | |
| EA007953B1 (ru) | Способы получения 4-[[4-[[4-(2-цианоэтенил)-2,6-диметилфенил]амино]-2-пиримидинил]амино]бензонитрила | |
| JPH11209366A (ja) | クロマン誘導体及び心不全治療薬 | |
| WO1997002259A1 (en) | 1,6-disubstituted isochromans for treatment of migraine headaches | |
| JP4129601B2 (ja) | クロマン誘導体 | |
| JP2016503812A (ja) | １−（［１，３］ジオキソラン−４−イルメチル）−１ｈ−ピラゾール−３−イルアミンを調製するための方法 | |
| KR900004929B1 (ko) | 메틸플라본 유도체의 제조방법 | |
| JPH09506885A (ja) | ５ｈｔ▲下１ｄ▼（抗うつ作用）活性を有するインドール、インドリンおよびキノリン誘導体 | |
| CN112939988A (zh) | 茚并吡唑并吡唑啉酮类化合物的合成方法及抗癌活性研究 | |
| EA002633B1 (ru) | Способ синтеза производных хинолина | |
| KR100323166B1 (ko) | 인터류킨-1 억제제의 합성에 유용한 푸란 설폰아미드 화합물의효율적인 합성방법 | |
| JPH0641105A (ja) | グリシド誘導体の製造方法 | |
| US5440036A (en) | 1,4-benzoxazine derivatives | |
| JP2001521498A (ja) | Ｏ−（３−アミノ−２−ヒドロキシ−プロピル）−ヒドロキシミック酸ハロゲン化物の製造方法 | |
| JP5044562B2 (ja) | オキセピン誘導体 | |
| CN107935881B (zh) | 一种n-[(2,4-二氟苯基)甲基]-4-甲氧基-3-氧代丁酰胺的制备方法 | |
| DE69415745T2 (de) | 5-Aminoflavon Derivate, deren Herstellung und deren Verwendung als antibakterielle und/oder anti-östrogene Mittel und/oder Antitumormittel | |
| CN114560862A (zh) | 一种吡咯并[1,2-a]喹喔啉-4(5h)-酮及其衍生物的合成方法 | |
| JP2023537436A (ja) | ３，６－ジクロロシアノピラジン、３，６－ジオキソピペラジン誘導体の調製のためのプロセス及びそれらを経由するファビピラビルの製造のためのプロセス | |
| CN116375703A (zh) | 一种阿哌沙班的合成工艺 | |
| JP3535565B2 (ja) | ベンゾピラン誘導体 | |
| JPH08188571A (ja) | ピロリジン誘導体 | |
| JP2006176490A (ja) | ５−フタランカルボニトリル及びシタロプラムの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 20010725 |