ZA200505461B - Pyridine derivatives usefl for inhibiting sodium/calcium exchange system - Google Patents

Info

Publication number

ZA200505461B

ZA200505461B ZA200505461A ZA200505461A ZA200505461B ZA 200505461 B ZA200505461 B ZA 200505461B ZA 200505461 A ZA200505461 A ZA 200505461A ZA 200505461 A ZA200505461 A ZA 200505461A ZA 200505461 B ZA200505461 B ZA 200505461B

Authority

ZA

South Africa

Prior art keywords

yloxy

chroman

pyridin

nmr

mhz

Prior art date

2003-01-09

Links

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• 230000002401 inhibitory effect Effects 0.000 title claims description 7
• 239000011734 sodium Substances 0.000 title description 17
• 239000011575 calcium Substances 0.000 title description 14
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title description 5
• 229910052791 calcium Inorganic materials 0.000 title description 5
• 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 4
• 150000003222 pyridines Chemical class 0.000 title description 4
• 229910052708 sodium Inorganic materials 0.000 title description 3
• 239000000203 mixture Substances 0.000 claims description 78
• 150000001875 compounds Chemical class 0.000 claims description 60
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 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 26
• 150000003839 salts Chemical class 0.000 claims description 18
• 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
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 230000007246 mechanism Effects 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 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
• 102000007399 Nuclear hormone receptor Human genes 0.000 claims description 6
• 108020005497 Nuclear hormone receptor Proteins 0.000 claims description 6
• 206010003119 arrhythmia Diseases 0.000 claims description 6
• 230000006793 arrhythmia Effects 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 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
• 229910052727 yttrium 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
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 239000000126 substance Substances 0.000 claims 3
• 238000004519 manufacturing process Methods 0.000 claims 2
• LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical group CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims 1
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 225
• 238000005481 NMR spectroscopy Methods 0.000 description 221
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
• 239000000243 solution Substances 0.000 description 86
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 74
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 61
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
• 239000011541 reaction mixture Substances 0.000 description 44
• 238000005160 1H NMR spectroscopy Methods 0.000 description 40
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• -1 Pyridin-2-yloxy Chemical class 0.000 description 37
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
• 229940093499 ethyl acetate Drugs 0.000 description 32
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
• 239000000047 product Substances 0.000 description 27
• 239000000543 intermediate Substances 0.000 description 26
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
• 230000002829 reductive effect Effects 0.000 description 22
• 238000004440 column chromatography Methods 0.000 description 21
• 229910000027 potassium carbonate Inorganic materials 0.000 description 18
• 235000011181 potassium carbonates Nutrition 0.000 description 18
• 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 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 16
• 239000000284 extract Substances 0.000 description 16
• 239000002904 solvent Substances 0.000 description 16
• 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
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
• 238000001816 cooling Methods 0.000 description 13
• 229940073584 methylene chloride Drugs 0.000 description 13
• 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 12
• 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 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 230000000875 corresponding effect Effects 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• XYHWPQUEOOBIOW-UHFFFAOYSA-N 6-hydroxyflavanone Chemical class C1C(=O)C2=CC(O)=CC=C2OC1C1=CC=CC=C1 XYHWPQUEOOBIOW-UHFFFAOYSA-N 0.000 description 11
• 239000002253 acid Substances 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 10
• LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 10
• 244000166550 Strophanthus gratus Species 0.000 description 10
• 229960000583 acetic acid Drugs 0.000 description 10
• SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 10
• 239000012044 organic layer Substances 0.000 description 10
• LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 10
• 229960003343 ouabain Drugs 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 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 8
• GCTFDMFLLBCLPF-UHFFFAOYSA-N 2,5-dichloropyridine Chemical compound ClC1=CC=C(Cl)N=C1 GCTFDMFLLBCLPF-UHFFFAOYSA-N 0.000 description 8
• 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
• BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 8
• NFAWYKUUWDFTHZ-UHFFFAOYSA-N 2-phenyl-3,4-dihydro-2h-chromen-6-ol Chemical compound C1CC2=CC(O)=CC=C2OC1C1=CC=CC=C1 NFAWYKUUWDFTHZ-UHFFFAOYSA-N 0.000 description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
• 150000003927 aminopyridines Chemical class 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
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
• 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 7
• 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 7
• SWAJPHCXKPCPQZ-UHFFFAOYSA-N 7-hydroxyflavanone Chemical class O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=CC=C1 SWAJPHCXKPCPQZ-UHFFFAOYSA-N 0.000 description 7
• 241000700199 Cavia porcellus Species 0.000 description 7
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
• 235000011054 acetic acid Nutrition 0.000 description 7
• 239000012043 crude product Substances 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 210000003540 papillary muscle Anatomy 0.000 description 7
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 7
• 229920006395 saturated elastomer Polymers 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
• 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 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 5
• 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 5
• BHJGJIOVSSSXDF-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1h-inden-5-ol Chemical class C1C2=CC(O)=CC=C2CC1C1=CC=CC=C1 BHJGJIOVSSSXDF-UHFFFAOYSA-N 0.000 description 5
• 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
• ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 5
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• 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 5
• 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 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 5
• 229930182821 L-proline Natural products 0.000 description 5
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
• 150000003869 acetamides Chemical class 0.000 description 5
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 230000008034 disappearance Effects 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 229960004592 isopropanol Drugs 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
• 238000003756 stirring Methods 0.000 description 5
• GFDFZTFQPIBNSQ-UHFFFAOYSA-N (+)-homo-18-epiormosanine Natural products C1C(C23)CCCN3CN3CCCCC3C32CN2CCCCC2C1C3 GFDFZTFQPIBNSQ-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
• UHRFABAQBKFMNK-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1,4-benzodioxin-6-ol Chemical class C1OC2=CC(O)=CC=C2OC1C1=CC=CC=C1 UHRFABAQBKFMNK-UHFFFAOYSA-N 0.000 description 4
• CPSFUCYWQUYUPC-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1,4-benzoxathiin-6-ol Chemical compound C1SC2=CC(O)=CC=C2OC1C1=CC=CC=C1 CPSFUCYWQUYUPC-UHFFFAOYSA-N 0.000 description 4
• GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 4
• QOWAWWLGBCNRSP-UHFFFAOYSA-N 6-hydroxy-2-phenyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC2=CC(O)=CC=C2C(=O)C1C1=CC=CC=C1 QOWAWWLGBCNRSP-UHFFFAOYSA-N 0.000 description 4
• XSTDIWNKASNIET-UHFFFAOYSA-N 6-methoxy-2-phenyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC2=CC(OC)=CC=C2C(=O)C1C1=CC=CC=C1 XSTDIWNKASNIET-UHFFFAOYSA-N 0.000 description 4
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• DTNIOAYHINWROM-LFHRXCRSSA-N tert-butyl n-[(2r)-3-methyl-1-oxo-1-[[6-[(2-phenyl-3,4-dihydro-2h-chromen-6-yl)oxy]pyridin-3-yl]amino]butan-2-yl]carbamate Chemical compound N1=CC(NC(=O)[C@H](NC(=O)OC(C)(C)C)C(C)C)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 DTNIOAYHINWROM-LFHRXCRSSA-N 0.000 description 1
• KAWHULVGZCZFGF-XNUZUHMRSA-N tert-butyl n-[(2s)-1-oxo-1-[[6-[(2-phenyl-3,4-dihydro-2h-chromen-6-yl)oxy]pyridin-3-yl]amino]propan-2-yl]carbamate Chemical compound N1=CC(NC(=O)[C@@H](NC(=O)OC(C)(C)C)C)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 KAWHULVGZCZFGF-XNUZUHMRSA-N 0.000 description 1
• ZHYUIFDQYPRZPN-NQCNTLBGSA-N tert-butyl n-[(2s)-3-hydroxy-1-oxo-1-[[6-[(2-phenyl-3,4-dihydro-2h-chromen-6-yl)oxy]pyridin-3-yl]amino]propan-2-yl]carbamate Chemical compound N1=CC(NC(=O)[C@H](CO)NC(=O)OC(C)(C)C)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 ZHYUIFDQYPRZPN-NQCNTLBGSA-N 0.000 description 1
• DTNIOAYHINWROM-WKDCXCOVSA-N tert-butyl n-[(2s)-3-methyl-1-oxo-1-[[6-[(2-phenyl-3,4-dihydro-2h-chromen-6-yl)oxy]pyridin-3-yl]amino]butan-2-yl]carbamate Chemical compound N1=CC(NC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 DTNIOAYHINWROM-WKDCXCOVSA-N 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 230000002537 thrombolytic effect Effects 0.000 description 1
• 238000002054 transplantation Methods 0.000 description 1
• 238000009736 wetting Methods 0.000 description 1