TW528755B - 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives - Google Patents

Info

Publication number

TW528755B

TW528755B TW086118941A TW86118941A TW528755B TW 528755 B TW528755 B TW 528755B TW 086118941 A TW086118941 A TW 086118941A TW 86118941 A TW86118941 A TW 86118941A TW 528755 B TW528755 B TW 528755B

Authority

TW

Taiwan

Prior art keywords

ethylamino

diol

ethyl

tetrahydro

purine

Prior art date

1996-12-24

Links

• Espacenet
• Global Dossier
• Discuss

• YQUJSBYIKMQCIT-UHFFFAOYSA-N 2-purin-9-yloxolane-3,4-diol Chemical class OC1C(O)COC1N1C2=NC=NC=C2N=C1 YQUJSBYIKMQCIT-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 271
• 238000000034 method Methods 0.000 claims abstract description 39
• -1 oxo- Chemical class 0.000 claims description 234
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 107
• 229910052757 nitrogen Inorganic materials 0.000 claims description 61
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 31
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 238000006243 chemical reaction Methods 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 13
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 239000003795 chemical substances by application Substances 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• SSYDTHANSGMJTP-UHFFFAOYSA-N oxolane-3,4-diol Chemical compound OC1COCC1O SSYDTHANSGMJTP-UHFFFAOYSA-N 0.000 claims description 11
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
• 239000011737 fluorine Substances 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 10
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• GPWHFPWZAPOYNO-UHFFFAOYSA-N 3,3-dimethylbutan-1-amine Chemical compound CC(C)(C)CCN GPWHFPWZAPOYNO-UHFFFAOYSA-N 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 239000004305 biphenyl Substances 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000004911 3,3-dimethylbutylamino group Chemical group CC(CCN*)(C)C 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 239000000463 material Substances 0.000 claims description 6
• 101150009274 nhr-1 gene Proteins 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• ULYSABNRLLVZCE-UHFFFAOYSA-N furan-3,4-diol Chemical compound OC1=COC=C1O ULYSABNRLLVZCE-UHFFFAOYSA-N 0.000 claims description 5
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 5
• 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 claims description 5
• CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 claims description 4
• ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 claims description 4
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 150000002431 hydrogen Chemical group 0.000 claims description 4
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 238000010511 deprotection reaction Methods 0.000 claims description 3
• 150000007857 hydrazones Chemical class 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 239000000460 chlorine Substances 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• 239000011630 iodine Substances 0.000 claims description 2
• SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 2
• 125000004899 1-ethylpropylamino group Chemical group C(C)C(CC)N* 0.000 claims 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
• LCFFJOYIXJKWRM-UHFFFAOYSA-N 2-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC(C2C(C(O)CO2)O)=N1 LCFFJOYIXJKWRM-UHFFFAOYSA-N 0.000 claims 2
• PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
• QFHBJRRQXVLZDI-OSKDKKHNSA-N (2r,3r,4s,5r)-2-[2-[(1-benzylpyrrolidin-3-yl)amino]-6-(pentan-3-ylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C3=NN(CC)N=N3)O)C=NC=2C(NC(CC)CC)=NC=1NC(C1)CCN1CC1=CC=CC=C1 QFHBJRRQXVLZDI-OSKDKKHNSA-N 0.000 claims 1
• QAYVJQBVKUEKEC-NBCVKUGOSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-hydroxyethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCO)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 QAYVJQBVKUEKEC-NBCVKUGOSA-N 0.000 claims 1
• BDVIOVSMFHLQFB-IMIIHFCZSA-N (2r,3s,4r,5r)-2-(2-ethyltetrazol-5-yl)-5-[6-(2-phenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCCC4)=NC(NCCC=4C=CC=CC=4)=C3N=C2)O)=N1 BDVIOVSMFHLQFB-IMIIHFCZSA-N 0.000 claims 1
• KUWWEKZFRBGGDO-CMCWBKRRSA-N (2r,3s,4r,5r)-2-(2-ethyltetrazol-5-yl)-5-[6-[(3-iodophenyl)methylamino]-2-(2-morpholin-4-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCOCC4)=NC(NCC=4C=C(I)C=CC=4)=C3N=C2)O)=N1 KUWWEKZFRBGGDO-CMCWBKRRSA-N 0.000 claims 1
• AWKWFPJUWHYSGJ-GRXQJBFDSA-N (2r,3s,4r,5r)-2-(2-methyltetrazol-5-yl)-5-[6-(pentan-3-ylamino)-2-(2-pyrrolidin-1-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C3=NN(C)N=N3)O)C=NC=2C(NC(CC)CC)=NC=1NCCN1CCCC1 AWKWFPJUWHYSGJ-GRXQJBFDSA-N 0.000 claims 1
• BKJJATGKMNJRBW-UHFFFAOYSA-N 2-(2-propan-2-yltetrazol-5-yl)oxolane-3,4-diol Chemical compound CC(C)N1N=NC(C2C(C(O)CO2)O)=N1 BKJJATGKMNJRBW-UHFFFAOYSA-N 0.000 claims 1
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
• QENKRUUMKMXSHL-VLJMVEFDSA-N CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(N[C@@H]4CC[C@@H](N)CC4)=NC(NC4CCCC4)=C3N=C2)O)=N1 Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(N[C@@H]4CC[C@@H](N)CC4)=NC(NC4CCCC4)=C3N=C2)O)=N1 QENKRUUMKMXSHL-VLJMVEFDSA-N 0.000 claims 1
• 239000005864 Sulphur Substances 0.000 claims 1
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
• 229940049706 benzodiazepine Drugs 0.000 claims 1
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
• 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
• 125000003884 phenylalkyl group Chemical group 0.000 claims 1
• XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Inorganic materials S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 92
• 238000009472 formulation Methods 0.000 abstract description 6
• 208000027866 inflammatory disease Diseases 0.000 abstract description 5
• 238000002560 therapeutic procedure Methods 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 226
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 213
• 239000007787 solid Substances 0.000 description 137
• 239000000543 intermediate Substances 0.000 description 119
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 110
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 109
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 106
• 239000011541 reaction mixture Substances 0.000 description 92
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 91
• 239000000243 solution Substances 0.000 description 69
• 238000004108 freeze drying Methods 0.000 description 66
• 239000002904 solvent Substances 0.000 description 66
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
• 230000002079 cooperative effect Effects 0.000 description 46
• 238000011049 filling Methods 0.000 description 41
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 38
• 239000000047 product Substances 0.000 description 36
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 35
• 238000004809 thin layer chromatography Methods 0.000 description 34
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 30
• 125000003118 aryl group Chemical group 0.000 description 30
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
• 239000003921 oil Substances 0.000 description 26
• 235000019198 oils Nutrition 0.000 description 26
• 239000002253 acid Substances 0.000 description 22
• 229910052681 coesite Inorganic materials 0.000 description 22
• 229910052906 cristobalite Inorganic materials 0.000 description 22
• 229910052682 stishovite Inorganic materials 0.000 description 22
• 229910052905 tridymite Inorganic materials 0.000 description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
• 239000006260 foam Substances 0.000 description 20
• 239000010410 layer Substances 0.000 description 20
• 239000002585 base Substances 0.000 description 19
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• 150000001298 alcohols Chemical class 0.000 description 17
• 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 15
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
• 150000002009 diols Chemical class 0.000 description 15
• 238000001819 mass spectrum Methods 0.000 description 15
• FHQDWPCFSJMNCT-UHFFFAOYSA-N N(tele)-methylhistamine Chemical compound CN1C=NC(CCN)=C1 FHQDWPCFSJMNCT-UHFFFAOYSA-N 0.000 description 14
• BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 14
• 238000004440 column chromatography Methods 0.000 description 14
• 239000006196 drop Substances 0.000 description 14
• 239000000706 filtrate Substances 0.000 description 14
• 238000004128 high performance liquid chromatography Methods 0.000 description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
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• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 13
• 238000002953 preparative HPLC Methods 0.000 description 13
• 108020003175 receptors Proteins 0.000 description 13
• 102000005962 receptors Human genes 0.000 description 13
• 238000012360 testing method Methods 0.000 description 13
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• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
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• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• 238000002414 normal-phase solid-phase extraction Methods 0.000 description 12
• 238000003756 stirring Methods 0.000 description 12
• RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
• 210000001519 tissue Anatomy 0.000 description 11
• LQLOGZQVKUNBRX-UHFFFAOYSA-N (3-iodophenyl)methanamine Chemical compound NCC1=CC=CC(I)=C1 LQLOGZQVKUNBRX-UHFFFAOYSA-N 0.000 description 10
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
• PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 10
• 229910021529 ammonia Inorganic materials 0.000 description 10
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
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