NO831950L - Farmasoeytiske preparater inneholdende (+)-cyanidan-3-ol-derivater, deres anvendelse, nye substituerte (+)-cyanidan-3-ol-derivater og fremgangsmaater til deres fremstilling - Google Patents

Info

Publication number

NO831950L

NO831950L NO831950A NO831950A NO831950L NO 831950 L NO831950 L NO 831950L NO 831950 A NO831950 A NO 831950A NO 831950 A NO831950 A NO 831950A NO 831950 L NO831950 L NO 831950L

Authority

NO

Norway

Prior art keywords

compounds

hydrogen

formula

benzyl

cyanidan

Prior art date

1982-06-01

Links

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• 238000002360 preparation method Methods 0.000 title claims abstract description 4
• 238000000034 method Methods 0.000 title claims description 97
• 239000000825 pharmaceutical preparation Substances 0.000 title abstract description 16
• PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical class C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 title abstract description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 282
• -1 heterocyclic radical Chemical class 0.000 claims abstract description 282
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 148
• 239000001257 hydrogen Substances 0.000 claims abstract description 148
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 89
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 73
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 72
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 62
• 150000002367 halogens Chemical class 0.000 claims abstract description 60
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 58
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 52
• 150000003839 salts Chemical class 0.000 claims abstract description 50
• 125000002252 acyl group Chemical group 0.000 claims abstract description 49
• 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 25
• 229930195733 hydrocarbon Natural products 0.000 claims abstract description 25
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 92
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 65
• 125000000217 alkyl group Chemical group 0.000 claims description 62
• 239000002253 acid Substances 0.000 claims description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 35
• 150000003254 radicals Chemical class 0.000 claims description 34
• 230000008569 process Effects 0.000 claims description 33
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
• 229910052794 bromium Inorganic materials 0.000 claims description 29
• 229910052740 iodine Inorganic materials 0.000 claims description 29
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 28
• 239000003795 chemical substances by application Substances 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 125000001931 aliphatic group Chemical group 0.000 claims description 19
• 238000006460 hydrolysis reaction Methods 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000004423 acyloxy group Chemical group 0.000 claims description 16
• 230000007062 hydrolysis Effects 0.000 claims description 16
• 125000001033 ether group Chemical group 0.000 claims description 15
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
• 230000009467 reduction Effects 0.000 claims description 15
• 239000007858 starting material Substances 0.000 claims description 15
• 125000003282 alkyl amino group Chemical group 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 12
• 238000003797 solvolysis reaction Methods 0.000 claims description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
• 125000003277 amino group Chemical group 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 7
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 7
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 230000002829 reductive effect Effects 0.000 claims description 5
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 4
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• 150000007522 mineralic acids Chemical class 0.000 claims description 4
• 125000001302 tertiary amino group Chemical group 0.000 claims description 4
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
• 239000004593 Epoxy Substances 0.000 claims description 3
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
• 238000006114 decarboxylation reaction Methods 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 125000006239 protecting group Chemical group 0.000 claims description 3
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
• 125000004442 acylamino group Chemical group 0.000 claims description 2
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 229960003237 betaine Drugs 0.000 claims description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
• 125000006277 halobenzyl group Chemical group 0.000 claims description 2
• JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 2
• KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims 1
• KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
• 239000012954 diazonium Substances 0.000 claims 1
• 210000004185 liver Anatomy 0.000 abstract description 4
• 208000019423 liver disease Diseases 0.000 abstract description 3
• 208000037997 venous disease Diseases 0.000 abstract description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract description 2
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 210
• 239000000243 solution Substances 0.000 description 203
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 155
• 239000000203 mixture Substances 0.000 description 140
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 127
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 120
• 238000002844 melting Methods 0.000 description 112
• 230000008018 melting Effects 0.000 description 110
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 96
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 94
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 65
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 64
• 239000002904 solvent Substances 0.000 description 64
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 62
• 238000006243 chemical reaction Methods 0.000 description 61
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
• 235000019441 ethanol Nutrition 0.000 description 57
• 239000007787 solid Substances 0.000 description 52
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 50
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 48
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 46
• 235000019341 magnesium sulphate Nutrition 0.000 description 46
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 45
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
• 238000001035 drying Methods 0.000 description 37
• 238000001704 evaporation Methods 0.000 description 35
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
• 238000001816 cooling Methods 0.000 description 31
• 229910052763 palladium Inorganic materials 0.000 description 31
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
• 239000003054 catalyst Substances 0.000 description 30
• 239000000741 silica gel Substances 0.000 description 29
• 229910002027 silica gel Inorganic materials 0.000 description 29
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
• 230000008020 evaporation Effects 0.000 description 28
• 229910052757 nitrogen Inorganic materials 0.000 description 28
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
• 238000003756 stirring Methods 0.000 description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
• 238000010438 heat treatment Methods 0.000 description 21
• 239000000725 suspension Substances 0.000 description 21
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
• 239000000126 substance Substances 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 150000007513 acids Chemical class 0.000 description 18
• 239000012074 organic phase Substances 0.000 description 18
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 17
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 17
• 150000002148 esters Chemical class 0.000 description 17
• 239000002244 precipitate Substances 0.000 description 17
• 239000000047 product Substances 0.000 description 17
• 239000013078 crystal Substances 0.000 description 16
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 16
• 238000005984 hydrogenation reaction Methods 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
• 239000003480 eluent Substances 0.000 description 15
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
• 239000013543 active substance Substances 0.000 description 14
• 125000005907 alkyl ester group Chemical group 0.000 description 14
• 239000002585 base Substances 0.000 description 14
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
• 238000006722 reduction reaction Methods 0.000 description 14
• 229910021529 ammonia Inorganic materials 0.000 description 13
• 150000001735 carboxylic acids Chemical class 0.000 description 13
• 238000001914 filtration Methods 0.000 description 13
• 238000001953 recrystallisation Methods 0.000 description 13
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• 238000007792 addition Methods 0.000 description 12
• 229910052783 alkali metal Inorganic materials 0.000 description 12
• 239000012442 inert solvent Substances 0.000 description 11
• 229910052749 magnesium Inorganic materials 0.000 description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
• 150000003335 secondary amines Chemical class 0.000 description 11
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 10
• 229960000583 acetic acid Drugs 0.000 description 10
• 239000003153 chemical reaction reagent Substances 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• 230000008025 crystallization Effects 0.000 description 10
• 229910052500 inorganic mineral Inorganic materials 0.000 description 10
• 239000011777 magnesium Substances 0.000 description 10
• 235000010755 mineral Nutrition 0.000 description 10
• 239000011707 mineral Substances 0.000 description 10
• 239000012071 phase Substances 0.000 description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
• 206010028980 Neoplasm Diseases 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 238000002425 crystallisation Methods 0.000 description 9
• 238000010828 elution Methods 0.000 description 9
• 238000000605 extraction Methods 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• 235000017557 sodium bicarbonate Nutrition 0.000 description 9
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
• 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 8
• 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 8
• 241001465754 Metazoa Species 0.000 description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 150000001340 alkali metals Chemical class 0.000 description 8
• 150000008064 anhydrides Chemical class 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 8
• 235000019253 formic acid Nutrition 0.000 description 8
• LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 8
• 239000011630 iodine Substances 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• 150000002825 nitriles Chemical class 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
• DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
• 241000699670 Mus sp. Species 0.000 description 7
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
• 238000009835 boiling Methods 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 238000004440 column chromatography Methods 0.000 description 7
• 201000010099 disease Diseases 0.000 description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 7
• 150000003141 primary amines Chemical class 0.000 description 7
• 239000011347 resin Substances 0.000 description 7
• 229920005989 resin Polymers 0.000 description 7
• 239000012047 saturated solution Substances 0.000 description 7
• 238000005406 washing Methods 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
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