HRP20050703A2 - Pyridine derivatives useful for inhibiting sodium/calcium exchange system - Google Patents

Info

Publication number

HRP20050703A2

HRP20050703A2 HR20050703A HRP20050703A HRP20050703A2 HR P20050703 A2 HRP20050703 A2 HR P20050703A2 HR 20050703 A HR20050703 A HR 20050703A HR P20050703 A HRP20050703 A HR P20050703A HR P20050703 A2 HRP20050703 A2 HR P20050703A2

Authority

HR

Croatia

Prior art keywords

yloxy

pyridin

chroman

nmr

mhz

Prior art date

2003-01-09

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• 230000002401 inhibitory effect Effects 0.000 title claims description 4
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title description 4
• 239000011575 calcium Substances 0.000 title description 4
• 229910052791 calcium Inorganic materials 0.000 title description 4
• 150000003222 pyridines Chemical class 0.000 title description 4
• 239000011734 sodium Substances 0.000 title description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 title description 2
• 229910052708 sodium Inorganic materials 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 59
• -1 -OH Chemical group 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 33
• 238000000034 method Methods 0.000 claims description 30
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 150000002148 esters Chemical class 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 230000007246 mechanism Effects 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 125000002252 acyl group Chemical group 0.000 claims description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
• 206010003119 arrhythmia Diseases 0.000 claims description 6
• 230000006793 arrhythmia Effects 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 101100240522 Caenorhabditis elegans nhr-18 gene Proteins 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 229910052727 yttrium Inorganic materials 0.000 claims description 3
• 101100240526 Caenorhabditis elegans nhr-20 gene Proteins 0.000 claims description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 238000005160 1H NMR spectroscopy Methods 0.000 description 265
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 236
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
• 239000000203 mixture Substances 0.000 description 77
• 239000000243 solution Substances 0.000 description 69
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
• 239000011541 reaction mixture Substances 0.000 description 44
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 37
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
• 239000002904 solvent Substances 0.000 description 31
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 30
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
• 239000000047 product Substances 0.000 description 24
• 230000002829 reductive effect Effects 0.000 description 22
• 238000004440 column chromatography Methods 0.000 description 21
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 239000003480 eluent Substances 0.000 description 19
• UCPDMDGWCCESMP-UHFFFAOYSA-N 6-[(2-phenyl-3,4-dihydro-2h-chromen-6-yl)oxy]pyridin-3-amine Chemical compound N1=CC(N)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 UCPDMDGWCCESMP-UHFFFAOYSA-N 0.000 description 18
• 229910000027 potassium carbonate Inorganic materials 0.000 description 18
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
• GZONLGPIHCCJOI-UHFFFAOYSA-N 5-nitro-2-[(2-phenyl-3,4-dihydro-2h-chromen-6-yl)oxy]pyridine Chemical compound N1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 GZONLGPIHCCJOI-UHFFFAOYSA-N 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 16
• 239000000284 extract Substances 0.000 description 16
• HNNVEYLZESPTPQ-UHFFFAOYSA-N 2-chloro-n-[6-[(2-phenyl-3,4-dihydro-2h-chromen-6-yl)oxy]pyridin-3-yl]acetamide Chemical compound N1=CC(NC(=O)CCl)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 HNNVEYLZESPTPQ-UHFFFAOYSA-N 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 239000000543 intermediate Substances 0.000 description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
• 238000001816 cooling Methods 0.000 description 13
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 12
• NFAWYKUUWDFTHZ-UHFFFAOYSA-N 2-phenyl-3,4-dihydro-2h-chromen-6-ol Chemical class C1CC2=CC(O)=CC=C2OC1C1=CC=CC=C1 NFAWYKUUWDFTHZ-UHFFFAOYSA-N 0.000 description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• XYHWPQUEOOBIOW-UHFFFAOYSA-N 6-hydroxyflavanone Chemical class C1C(=O)C2=CC(O)=CC=C2OC1C1=CC=CC=C1 XYHWPQUEOOBIOW-UHFFFAOYSA-N 0.000 description 10
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 229960000583 acetic acid Drugs 0.000 description 10
• 239000012044 organic layer Substances 0.000 description 10
• JWOHBPPVVDQMKB-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-4-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC(C(O)=O)CC1 JWOHBPPVVDQMKB-UHFFFAOYSA-N 0.000 description 9
• BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 9
• KYSUJMHYJQLLLO-UHFFFAOYSA-N 6-[(2-phenyl-3,4-dihydro-2h-chromen-6-yl)oxy]pyridin-3-amine;piperidine-4-carboxylic acid Chemical compound OC(=O)C1CCNCC1.N1=CC(N)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 KYSUJMHYJQLLLO-UHFFFAOYSA-N 0.000 description 9
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
• 235000011152 sodium sulphate Nutrition 0.000 description 9
• HRVBYTVYJAPLHB-UHFFFAOYSA-N 2-(4-fluorophenyl)-3,4-dihydro-2h-chromen-6-ol Chemical compound C1CC2=CC(O)=CC=C2OC1C1=CC=C(F)C=C1 HRVBYTVYJAPLHB-UHFFFAOYSA-N 0.000 description 8
• KFUMHIDDQQILEL-UHFFFAOYSA-N 2-phenyl-3,4-dihydro-2h-chromen-7-ol Chemical class O1C2=CC(O)=CC=C2CCC1C1=CC=CC=C1 KFUMHIDDQQILEL-UHFFFAOYSA-N 0.000 description 8
• ZJUXJQSYXBYFFO-UHFFFAOYSA-N 4-[(4-methylpiperazin-4-ium-1-yl)methyl]benzoate Chemical compound C1CN(C)CCN1CC1=CC=C(C(O)=O)C=C1 ZJUXJQSYXBYFFO-UHFFFAOYSA-N 0.000 description 8
• 239000007832 Na2SO4 Substances 0.000 description 8
• 150000003927 aminopyridines Chemical class 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 8
• NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
• CTNPHHZPAJYPFO-PDXBGNJTSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-3-[(2r,4s,5r,6r)-5-[(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2h-furan Chemical compound C1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C=O)CC[C@@H](C[C@@]5(O)CC[C@H]4[C@@]3(O)CC2)O[C@H]2C[C@@H]([C@@H]([C@@H](C)O2)O[C@@H]2[C@H]([C@H](O)[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@H](CO)O2)O)OC)=CC(=O)OC1 CTNPHHZPAJYPFO-PDXBGNJTSA-N 0.000 description 7
• GCTFDMFLLBCLPF-UHFFFAOYSA-N 2,5-dichloropyridine Chemical compound ClC1=CC=C(Cl)N=C1 GCTFDMFLLBCLPF-UHFFFAOYSA-N 0.000 description 7
• FFEOOGDQASYIMF-UHFFFAOYSA-N 5-chloro-2-[(2-phenyl-3,4-dihydro-2h-chromen-6-yl)oxy]pyridine Chemical compound N1=CC(Cl)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 FFEOOGDQASYIMF-UHFFFAOYSA-N 0.000 description 7
• 241000700199 Cavia porcellus Species 0.000 description 7
• FHIREUBIEIPPMC-UHFFFAOYSA-N K-Strophanthin-beta Natural products O1C(C)C(OC2C(C(O)C(O)C(CO)O2)O)C(OC)CC1OC(CC1(O)CCC2C3(O)CC4)CCC1(C=O)C2CCC3(C)C4C1=CC(=O)OC1 FHIREUBIEIPPMC-UHFFFAOYSA-N 0.000 description 7
• 235000011054 acetic acid Nutrition 0.000 description 7
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• SUIHNCCYZMUFEH-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-3,4-dihydro-2h-chromen-6-ol Chemical compound OC1=CC=CC(C2OC3=CC=C(O)C=C3CC2)=C1 SUIHNCCYZMUFEH-UHFFFAOYSA-N 0.000 description 6
• CXFCPHACGDFVOB-UHFFFAOYSA-N 2-(4-fluorophenyl)-3,4-dihydro-2h-chromene-4,6-diol Chemical compound O1C2=CC=C(O)C=C2C(O)CC1C1=CC=C(F)C=C1 CXFCPHACGDFVOB-UHFFFAOYSA-N 0.000 description 6
• NTHKEMDHJFZMRT-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-hydroxy-2,3-dihydrochromen-4-one Chemical compound C1C(=O)C2=CC(O)=CC=C2OC1C1=CC=C(F)C=C1 NTHKEMDHJFZMRT-UHFFFAOYSA-N 0.000 description 6
• UHRFABAQBKFMNK-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1,4-benzodioxin-6-ol Chemical compound C1OC2=CC(O)=CC=C2OC1C1=CC=CC=C1 UHRFABAQBKFMNK-UHFFFAOYSA-N 0.000 description 6
• BHJGJIOVSSSXDF-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1h-inden-5-ol Chemical compound C1C2=CC(O)=CC=C2CC1C1=CC=CC=C1 BHJGJIOVSSSXDF-UHFFFAOYSA-N 0.000 description 6
• UTVSNCZURCQGEV-UHFFFAOYSA-N 6-phenyl-5,6,7,8-tetrahydronaphthalen-2-ol Chemical compound C1CC2=CC(O)=CC=C2CC1C1=CC=CC=C1 UTVSNCZURCQGEV-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 150000004702 methyl esters Chemical class 0.000 description 6
• 210000003540 papillary muscle Anatomy 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• 239000001384 succinic acid Substances 0.000 description 6
• UPOFPJMROJNPAW-UHFFFAOYSA-N 3-(3-fluorophenyl)-3,4-dihydro-2h-chromen-7-ol Chemical compound C1OC2=CC(O)=CC=C2CC1C1=CC=CC(F)=C1 UPOFPJMROJNPAW-UHFFFAOYSA-N 0.000 description 5
• FJUORDALKHVXDF-UHFFFAOYSA-N 3-(3-fluorophenyl)-7-hydroxychromen-4-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC=C2C1=CC=CC(F)=C1 FJUORDALKHVXDF-UHFFFAOYSA-N 0.000 description 5
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
• OUYPJKIKPBDKMY-UHFFFAOYSA-N 5-nitro-2-[(2-phenyl-2,3-dihydro-1h-inden-5-yl)oxy]pyridine Chemical compound N1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(CC(C2)C=3C=CC=CC=3)C2=C1 OUYPJKIKPBDKMY-UHFFFAOYSA-N 0.000 description 5
• SWAJPHCXKPCPQZ-UHFFFAOYSA-N 7-hydroxyflavanone Chemical class O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=CC=C1 SWAJPHCXKPCPQZ-UHFFFAOYSA-N 0.000 description 5
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
• 150000003869 acetamides Chemical class 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 239000012267 brine Substances 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 230000002349 favourable effect Effects 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 239000004615 ingredient Substances 0.000 description 5
• 210000003205 muscle Anatomy 0.000 description 5
• ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 5
• 150000002989 phenols Chemical class 0.000 description 5
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
• WLDWSGZHNBANIO-UHFFFAOYSA-N 2',5'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC(O)=CC=C1O WLDWSGZHNBANIO-UHFFFAOYSA-N 0.000 description 4
• XATOFSIUMVTTJN-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-3,4-dihydro-2h-chromene-4,6-diol Chemical compound O1C2=CC=C(O)C=C2C(O)CC1C1=CC=CC(O)=C1 XATOFSIUMVTTJN-UHFFFAOYSA-N 0.000 description 4
• MXJZJVWVHUGNLF-UHFFFAOYSA-N 2-[[3-(3-fluorophenyl)-3,4-dihydro-2h-chromen-7-yl]oxy]-5-nitropyridine Chemical compound N1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(CC(CO2)C=3C=C(F)C=CC=3)C2=C1 MXJZJVWVHUGNLF-UHFFFAOYSA-N 0.000 description 4
• IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
• ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical class COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 4
• LKMWTIGVJAWQHQ-UHFFFAOYSA-N 3-phenyl-3,4-dihydro-2h-chromen-7-ol Chemical compound C1OC2=CC(O)=CC=C2CC1C1=CC=CC=C1 LKMWTIGVJAWQHQ-UHFFFAOYSA-N 0.000 description 4
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• GODPLEVRIKBDCU-UHFFFAOYSA-N 5-nitro-2-[(6-phenyl-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]pyridine Chemical compound N1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(CC(CC2)C=3C=CC=CC=3)C2=C1 GODPLEVRIKBDCU-UHFFFAOYSA-N 0.000 description 4
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