BRPI0711529A2 - composto, composição farmacêutica, métodos de tratamento ou redução do risco das doenças ou condições, de tratamento ou redução do risco de distúrbios neuroinflamatórios e de tratamento ou redução do risco de distúrbios ateroscleóticos cardio e cerebrovasculares ou doença arterial periférica, insuficiência cardìaca e distúrbios respiratórios, e, uso de um composto - Google Patents

Info

Publication number

BRPI0711529A2

BRPI0711529A2 BRPI0711529-6A BRPI0711529A BRPI0711529A2 BR PI0711529 A2 BRPI0711529 A2 BR PI0711529A2 BR PI0711529 A BRPI0711529 A BR PI0711529A BR PI0711529 A2 BRPI0711529 A2 BR PI0711529A2

Authority

BR

Brazil

Prior art keywords

alkoxy

alkyl

thioxo

phenoxy

tetrahydro

Prior art date

2006-04-13

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 390
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 46
• 238000000034 method Methods 0.000 title claims abstract description 44
• 201000010099 disease Diseases 0.000 title claims abstract description 35
• 208000036110 Neuroinflammatory disease Diseases 0.000 title claims abstract description 12
• 208000035475 disorder Diseases 0.000 title claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
• 208000023504 respiratory system disease Diseases 0.000 title claims abstract description 10
• 206010019280 Heart failures Diseases 0.000 title claims abstract description 9
• 208000005764 Peripheral Arterial Disease Diseases 0.000 title claims abstract description 8
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 title claims abstract description 8
• 230000003143 atherosclerotic effect Effects 0.000 title claims description 11
• 150000003839 salts Chemical class 0.000 claims abstract description 60
• 238000011282 treatment Methods 0.000 claims abstract description 32
• 238000011321 prophylaxis Methods 0.000 claims abstract description 16
• 102000004190 Enzymes Human genes 0.000 claims abstract description 10
• 108090000790 Enzymes Proteins 0.000 claims abstract description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 254
• 125000000217 alkyl group Chemical group 0.000 claims description 232
• 229910052760 oxygen Inorganic materials 0.000 claims description 182
• 229920006395 saturated elastomer Polymers 0.000 claims description 170
• 229910052717 sulfur Inorganic materials 0.000 claims description 156
• 229910052736 halogen Inorganic materials 0.000 claims description 155
• 150000002367 halogens Chemical class 0.000 claims description 155
• 201000006417 multiple sclerosis Diseases 0.000 claims description 151
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 150
• 125000003118 aryl group Chemical group 0.000 claims description 121
• 125000005842 heteroatom Chemical group 0.000 claims description 84
• -1 OH5 halogen Chemical group 0.000 claims description 61
• 125000004429 atom Chemical group 0.000 claims description 58
• 125000002950 monocyclic group Chemical group 0.000 claims description 58
• 125000001424 substituent group Chemical group 0.000 claims description 51
• 229910052757 nitrogen Inorganic materials 0.000 claims description 46
• 239000000460 chlorine Substances 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 33
• 125000004122 cyclic group Chemical group 0.000 claims description 33
• 239000001301 oxygen Substances 0.000 claims description 33
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 19
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 19
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 239000012453 solvate Substances 0.000 claims description 19
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 18
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 150000002431 hydrogen Chemical group 0.000 claims description 17
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 14
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 201000001320 Atherosclerosis Diseases 0.000 claims description 11
• 208000018737 Parkinson disease Diseases 0.000 claims description 11
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 9
• 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 7
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 6
• 239000002671 adjuvant Substances 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 6
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 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
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• 150000003852 triazoles Chemical class 0.000 claims description 6
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 5
• 230000009286 beneficial effect Effects 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 208000015181 infectious disease Diseases 0.000 claims description 5
• 230000005764 inhibitory process Effects 0.000 claims description 5
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• IIIADLWTNVXNBD-UHFFFAOYSA-N 3-(2-aminopropyl)-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O=C1NC(=S)N(CC(N)C)C2=C1NC=N2 IIIADLWTNVXNBD-UHFFFAOYSA-N 0.000 claims description 4
• 206010014561 Emphysema Diseases 0.000 claims description 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• 206010006451 bronchitis Diseases 0.000 claims description 4
• JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• ATPOLLKTGMVGBH-UHFFFAOYSA-N 3-[2-(pyridin-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CC=N1 ATPOLLKTGMVGBH-UHFFFAOYSA-N 0.000 claims description 3
• ZIWMBSQQYYREIU-UHFFFAOYSA-N 3-[2-[(6-chloropyridin-3-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=C(Cl)N=C1 ZIWMBSQQYYREIU-UHFFFAOYSA-N 0.000 claims description 3
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
• 206010065563 Eosinophilic bronchitis Diseases 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 201000009267 bronchiectasis Diseases 0.000 claims description 3
• 230000002458 infectious effect Effects 0.000 claims description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
• UYLWKSJTHLRFBX-UHFFFAOYSA-N purin-6-one Chemical compound O=C1N=CN=C2N=CN=C12 UYLWKSJTHLRFBX-UHFFFAOYSA-N 0.000 claims description 3
• WIOYFBDCQDDCTI-UHFFFAOYSA-N 2-sulfanylidene-3-[2-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]propyl]-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=C(C(F)(F)F)N=C1 WIOYFBDCQDDCTI-UHFFFAOYSA-N 0.000 claims description 2
• SKAUBHPJNDJLBF-UHFFFAOYSA-N 3-[2-(quinolin-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=CC2=NC(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 SKAUBHPJNDJLBF-UHFFFAOYSA-N 0.000 claims description 2
• DSUIOKUNQXSQHF-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]-1,8-naphthyridine-2-carboxamide Chemical compound C1=CC=NC2=NC(C(=O)NC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 DSUIOKUNQXSQHF-UHFFFAOYSA-N 0.000 claims description 2
• SMBFHTPOCAIXGA-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]pyridine-2-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=CC=CC=N1 SMBFHTPOCAIXGA-UHFFFAOYSA-N 0.000 claims description 2
• CVVVWYUXSNNDLD-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)NC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 CVVVWYUXSNNDLD-UHFFFAOYSA-N 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 125000002252 acyl group Chemical group 0.000 claims 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
• 125000004171 alkoxy aryl group Chemical group 0.000 claims 1
• FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims 1
• 230000029058 respiratory gaseous exchange Effects 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 91
• 238000002360 preparation method Methods 0.000 abstract description 11
• 230000008569 process Effects 0.000 abstract description 8
• 230000009467 reduction Effects 0.000 abstract description 8
• 238000002560 therapeutic procedure Methods 0.000 abstract description 8
• 239000003112 inhibitor Substances 0.000 abstract description 6
• 230000002093 peripheral effect Effects 0.000 abstract description 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 264
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 155
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 149
• 238000005160 1H NMR spectroscopy Methods 0.000 description 113
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 80
• 239000000243 solution Substances 0.000 description 74
• 239000007787 solid Substances 0.000 description 73
• 238000007429 general method Methods 0.000 description 66
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
• 239000011541 reaction mixture Substances 0.000 description 54
• 102000003896 Myeloperoxidases Human genes 0.000 description 51
• 108090000235 Myeloperoxidases Proteins 0.000 description 51
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 50
• 235000019439 ethyl acetate Nutrition 0.000 description 50
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
• 238000006243 chemical reaction Methods 0.000 description 42
• 238000000746 purification Methods 0.000 description 42
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 37
• 239000002904 solvent Substances 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 32
• 239000012043 crude product Substances 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
• 238000001914 filtration Methods 0.000 description 29
• 239000000047 product Substances 0.000 description 28
• 229960000583 acetic acid Drugs 0.000 description 27
• 238000002953 preparative HPLC Methods 0.000 description 27
• 238000010992 reflux Methods 0.000 description 25
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
• 229910021529 ammonia Inorganic materials 0.000 description 24
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 22
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
• 239000012044 organic layer Substances 0.000 description 20
• 238000005481 NMR spectroscopy Methods 0.000 description 17
• CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 17
• 239000012074 organic phase Substances 0.000 description 17
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 16
• 239000000543 intermediate Substances 0.000 description 16
• DVNYTAVYBRSTGK-UHFFFAOYSA-N 5-aminoimidazole-4-carboxamide Chemical compound NC(=O)C=1N=CNC=1N DVNYTAVYBRSTGK-UHFFFAOYSA-N 0.000 description 14
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 125000002947 alkylene group Chemical group 0.000 description 14
• 238000001816 cooling Methods 0.000 description 14
• ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 14
• 239000000463 material Substances 0.000 description 14
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 14
• 239000003643 water by type Substances 0.000 description 14
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
• 229910052938 sodium sulfate Inorganic materials 0.000 description 13
• 235000011152 sodium sulphate Nutrition 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
• 238000010438 heat treatment Methods 0.000 description 12
• 230000003902 lesion Effects 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• 239000008346 aqueous phase Substances 0.000 description 11
• 238000003818 flash chromatography Methods 0.000 description 11
• 238000010898 silica gel chromatography Methods 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 235000010288 sodium nitrite Nutrition 0.000 description 11
• 206010012289 Dementia Diseases 0.000 description 10
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 10
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
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