EA029272B1 - Пуриновые производные, применимые в качестве ингибиторов hsp90 - Google Patents

Info

Publication number

EA029272B1

EA029272B1 EA201270535A EA201270535A EA029272B1 EA 029272 B1 EA029272 B1 EA 029272B1 EA 201270535 A EA201270535 A EA 201270535A EA 201270535 A EA201270535 A EA 201270535A EA 029272 B1 EA029272 B1 EA 029272B1

Authority

EA

Eurasian Patent Office

Prior art keywords

propyl

ethyl

isopropylamino

methyl

dioxol

Prior art date

2009-10-07

Links

• Espacenet
• Global Dossier
• Discuss

• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title abstract description 3
• 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title abstract 2
• 239000003481 heat shock protein 90 inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 208
• 238000011282 treatment Methods 0.000 claims abstract description 9
• -1 3,3-dimethyl-but-1-ynyl Chemical group 0.000 claims description 1803
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 523
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 418
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 361
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 319
• 229910052757 nitrogen Inorganic materials 0.000 claims description 230
• 125000005605 benzo group Chemical group 0.000 claims description 226
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 208
• 239000000460 chlorine Substances 0.000 claims description 126
• 238000000034 method Methods 0.000 claims description 123
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 93
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 93
• 125000003118 aryl group Chemical group 0.000 claims description 90
• 229960000643 adenine Drugs 0.000 claims description 73
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 72
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 63
• JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims description 60
• 125000000217 alkyl group Chemical group 0.000 claims description 58
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 56
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 49
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 47
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 36
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 34
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 33
• 125000000304 alkynyl group Chemical group 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 31
• 239000001294 propane Substances 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 30
• 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 26
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 125000004122 cyclic group Chemical group 0.000 claims description 24
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 239000001301 oxygen Substances 0.000 claims description 20
• 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
• 239000011593 sulfur Substances 0.000 claims description 19
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 18
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
• 229930192474 thiophene Natural products 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 206010028980 Neoplasm Diseases 0.000 claims description 14
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 13
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
• GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 12
• 125000006308 propyl amino group Chemical group 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 6
• 230000004770 neurodegeneration Effects 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 229930024421 Adenine Natural products 0.000 claims description 5
• 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 4
• CLGUKFNQTOCQDG-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]-8-[[6-(1h-pyrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCNCC(C)C)C=1CC1=CC=2OCCOC=2C=C1C=1C=CNN=1 CLGUKFNQTOCQDG-UHFFFAOYSA-N 0.000 claims description 3
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
• RWDCITLWLGCCJT-UHFFFAOYSA-N 8-(3-iodonaphthalen-2-yl)sulfanyl-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC4=CC=CC=C4C=3)I)=NC2=C1N RWDCITLWLGCCJT-UHFFFAOYSA-N 0.000 claims description 3
• 229920000305 Nylon 6,10 Polymers 0.000 claims description 3
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 3
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• HDFWKQKSLRXFFF-UHFFFAOYSA-N 8-[[6-(2-phenylethynyl)-1,3-benzodioxol-5-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2OCOC=2C=C1C#CC1=CC=CC=C1 HDFWKQKSLRXFFF-UHFFFAOYSA-N 0.000 claims description 2
• QGWBWRZAEAMZCO-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-(5-methoxy-2-thiophen-2-ylphenyl)sulfanylpurin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCNCC(C)(C)C)C=1SC1=CC(OC)=CC=C1C1=CC=CS1 QGWBWRZAEAMZCO-UHFFFAOYSA-N 0.000 claims description 2
• JCHVHNXVRNVJSL-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[(5-thiophen-2-yl-2,3-dihydro-1-benzofuran-6-yl)sulfanyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCNCC(C)(C)C)C=1SC1=CC=2OCCC=2C=C1C1=CC=CS1 JCHVHNXVRNVJSL-UHFFFAOYSA-N 0.000 claims description 2
• GNZBBBFEWKVWLU-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[2-(furan-2-yl)-5-methoxyphenyl]sulfanylpurin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCNCC(C)(C)C)C=1SC1=CC(OC)=CC=C1C1=CC=CO1 GNZBBBFEWKVWLU-UHFFFAOYSA-N 0.000 claims description 2
• LQCCHYJASZQDSG-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[5-methoxy-2-(1h-pyrazol-5-yl)phenyl]sulfanylpurin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCNCC(C)(C)C)C=1SC1=CC(OC)=CC=C1C=1C=CNN=1 LQCCHYJASZQDSG-UHFFFAOYSA-N 0.000 claims description 2
• VSLGCTHNSARJOW-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[[5-(furan-2-yl)-2,3-dihydro-1-benzofuran-6-yl]sulfanyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCNCC(C)(C)C)C=1SC1=CC=2OCCC=2C=C1C1=CC=CO1 VSLGCTHNSARJOW-UHFFFAOYSA-N 0.000 claims description 2
• ROASJEHPZNKHOF-UHFFFAOYSA-N hexyl carbamate Chemical compound CCCCCCOC(N)=O ROASJEHPZNKHOF-UHFFFAOYSA-N 0.000 claims description 2
• 230000002401 inhibitory effect Effects 0.000 claims description 2
• 125000002971 oxazolyl group Chemical group 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 6
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 5
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 5
• 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims 4
• 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 claims 3
• 239000008194 pharmaceutical composition Substances 0.000 claims 3
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
• ZFMJTBHCAGPOJA-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[(6-ethynyl-2,3-dihydro-1h-inden-5-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)(C)C)C(SC=3C(=CC=4CCCC=4C=3)C#C)=NC2=C1N ZFMJTBHCAGPOJA-UHFFFAOYSA-N 0.000 claims 2
• NJNKSCQLKJFJDP-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-(2-ethynyl-5-methoxyphenyl)sulfanylpurin-6-amine Chemical compound COC1=CC=C(C#C)C(SC=2N(C3=NC=NC(N)=C3N=2)CCNCC(C)(C)C)=C1 NJNKSCQLKJFJDP-UHFFFAOYSA-N 0.000 claims 1
• PNBOZZKLKLNHBS-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[(5-ethynyl-2,3-dihydro-1-benzofuran-6-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)(C)C)C(SC=3C(=CC=4CCOC=4C=3)C#C)=NC2=C1N PNBOZZKLKLNHBS-UHFFFAOYSA-N 0.000 claims 1
• 125000002541 furyl group Chemical group 0.000 claims 1
• 125000000335 thiazolyl group Chemical group 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 4
• 201000010099 disease Diseases 0.000 abstract description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
• 101710113864 Heat shock protein 90 Proteins 0.000 abstract 1
• 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 abstract 1
• 238000005481 NMR spectroscopy Methods 0.000 description 187
• 239000011541 reaction mixture Substances 0.000 description 178
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 125
• 230000002829 reductive effect Effects 0.000 description 97
• 239000000203 mixture Substances 0.000 description 76
• 239000002904 solvent Substances 0.000 description 76
• 238000012746 preparative thin layer chromatography Methods 0.000 description 73
• 229910052740 iodine Inorganic materials 0.000 description 72
• 125000006309 butyl amino group Chemical group 0.000 description 68
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 62
• 239000000243 solution Substances 0.000 description 62
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
• 238000004128 high performance liquid chromatography Methods 0.000 description 58
• 239000007787 solid Substances 0.000 description 58
• 102100037580 Sesquipedalian-1 Human genes 0.000 description 49
• 101710169844 Sesquipedalian-1 Proteins 0.000 description 49
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 40
• ZENKESXKWBIZCV-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-1,3-benzodioxin-6-amine Chemical group O1C(F)(F)OC(F)(F)C2=CC(N)=CC=C21 ZENKESXKWBIZCV-UHFFFAOYSA-N 0.000 description 35
• 125000000278 alkyl amino alkyl group Chemical group 0.000 description 31
• 238000003818 flash chromatography Methods 0.000 description 31
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• 125000004103 aminoalkyl group Chemical group 0.000 description 29
• 210000004556 brain Anatomy 0.000 description 29
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 28
• 125000003710 aryl alkyl group Chemical group 0.000 description 28
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 28
• 239000013592 cell lysate Substances 0.000 description 26
• 210000004027 cell Anatomy 0.000 description 25
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 25
• VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 22
• 239000003153 chemical reaction reagent Substances 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 19
• PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 18
• KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 18
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 18
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 18
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 17
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 15
• BHVOFCPOXNYVCE-UHFFFAOYSA-N 6-amino-7,9-dihydropurine-8-thione Chemical compound NC1=NC=NC2=C1NC(=S)N2 BHVOFCPOXNYVCE-UHFFFAOYSA-N 0.000 description 15
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 15
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
• 210000004958 brain cell Anatomy 0.000 description 14
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
• FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 13
• 238000004587 chromatography analysis Methods 0.000 description 13
• 101150072179 ATP1 gene Proteins 0.000 description 12
• 101100003366 Arabidopsis thaliana ATPA gene Proteins 0.000 description 12
• 102100021649 Elongator complex protein 6 Human genes 0.000 description 12
• 101100065219 Homo sapiens ELP6 gene Proteins 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000003277 amino group Chemical group 0.000 description 12
• 101150105046 atpI gene Proteins 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
• 125000000623 heterocyclic group Chemical group 0.000 description 11
• 238000010992 reflux Methods 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• 239000011737 fluorine Substances 0.000 description 10
• 229910052731 fluorine Inorganic materials 0.000 description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
• 239000012044 organic layer Substances 0.000 description 10
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 10
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 9
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• 125000004093 cyano group Chemical group *C#N 0.000 description 9
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 9
• ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 8
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• 101100293693 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) STO1 gene Proteins 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 8
• 101150050497 cbc1 gene Proteins 0.000 description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
• XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 7
• BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 7
• 101150116038 AEP2 gene Proteins 0.000 description 7
• 241000699670 Mus sp. Species 0.000 description 7
• 125000003282 alkyl amino group Chemical group 0.000 description 7
• 238000006243 chemical reaction Methods 0.000 description 7
• 125000001309 chloro group Chemical group Cl* 0.000 description 7
• 125000001153 fluoro group Chemical group F* 0.000 description 7
• PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 7
• 239000011630 iodine Substances 0.000 description 7
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 7
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
• IYRGXJIJGHOCFS-UHFFFAOYSA-N neocuproine Chemical compound C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1 IYRGXJIJGHOCFS-UHFFFAOYSA-N 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• NEUWPDLMDVINSN-UHFFFAOYSA-N 1h-pyrazol-5-ylboronic acid Chemical compound OB(O)C=1C=CNN=1 NEUWPDLMDVINSN-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• 206010006187 Breast cancer Diseases 0.000 description 6
• 208000026310 Breast neoplasm Diseases 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 229940124530 sulfonamide Drugs 0.000 description 6
• 239000004215 Carbon black (E152) Substances 0.000 description 5
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
• 150000001412 amines Chemical class 0.000 description 5
• 150000001721 carbon Chemical group 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 125000004966 cyanoalkyl group Chemical group 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 150000002430 hydrocarbons Chemical class 0.000 description 5
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 5
• 238000004809 thin layer chromatography Methods 0.000 description 5
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 5
• LXCICYRNWIGDQA-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CON=C1 LXCICYRNWIGDQA-UHFFFAOYSA-N 0.000 description 4
• PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 4
• LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 4
• UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
• 101100037618 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ant-1 gene Proteins 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 239000012230 colorless oil Substances 0.000 description 4
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 4
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 4
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
• 150000002460 imidazoles Chemical class 0.000 description 4
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
• GGIUUCJLIYQRAE-UHFFFAOYSA-N propyl sulfamate Chemical compound CCCOS(N)(=O)=O GGIUUCJLIYQRAE-UHFFFAOYSA-N 0.000 description 4
• 150000003222 pyridines Chemical class 0.000 description 4
• PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 4
• ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 4
• IKDMREAHMCMBIG-UHFFFAOYSA-N 1,3-dioxole-4-carbonitrile Chemical compound N#CC1=COCO1 IKDMREAHMCMBIG-UHFFFAOYSA-N 0.000 description 3
• FNPZFZKLYGWKLH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane Chemical compound O1C(C)=CC=C1B1OC(C)(C)C(C)(C)O1 FNPZFZKLYGWKLH-UHFFFAOYSA-N 0.000 description 3
• MBLGEUGNABDCDM-UHFFFAOYSA-N 8-[(5-iodo-2,3-dihydro-1-benzofuran-6-yl)sulfanyl]-7h-purin-6-amine Chemical compound N=1C=2C(N)=NC=NC=2NC=1SC(C(=C1)I)=CC2=C1CCO2 MBLGEUGNABDCDM-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 101100456282 Caenorhabditis elegans mcm-4 gene Proteins 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• 101000587820 Homo sapiens Selenide, water dikinase 1 Proteins 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• 102100031163 Selenide, water dikinase 1 Human genes 0.000 description 3
• JTFQDOHHXGSMFC-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrol-3-yl]boronic acid Chemical compound CC(C)(C)OC(=O)N1C=CC(B(O)O)=C1 JTFQDOHHXGSMFC-UHFFFAOYSA-N 0.000 description 3
• 229910052786 argon Inorganic materials 0.000 description 3
• 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 description 3
• 229910052801 chlorine Inorganic materials 0.000 description 3
• 125000004663 dialkyl amino group Chemical group 0.000 description 3
• CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 3
• 125000001072 heteroaryl group Chemical group 0.000 description 3
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 3
• 239000010410 layer Substances 0.000 description 3
• 125000005647 linker group Chemical group 0.000 description 3
• 239000006166 lysate Substances 0.000 description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 239000012299 nitrogen atmosphere Substances 0.000 description 3
• 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 3
• 125000004430 oxygen atom Chemical group O* 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 150000003456 sulfonamides Chemical class 0.000 description 3
• 230000001225 therapeutic effect Effects 0.000 description 3
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 3
• MGNBKNBEZGLHNF-UHFFFAOYSA-N (2-methylpyrazol-3-yl)boronic acid Chemical compound CN1N=CC=C1B(O)O MGNBKNBEZGLHNF-UHFFFAOYSA-N 0.000 description 2
• JUWYQISLQJRRNT-UHFFFAOYSA-N (5-formylfuran-2-yl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)O1 JUWYQISLQJRRNT-UHFFFAOYSA-N 0.000 description 2
• KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 description 2
• ZDLCRJZSWKJVQO-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-6-amine Chemical compound NC1=CC=C2CCOC2=C1 ZDLCRJZSWKJVQO-UHFFFAOYSA-N 0.000 description 2
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
• GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 2
• VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
• INQUEXIWISVGOP-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=C(F)N=C2N(CCNCC(C)C)C=NC2=C1N INQUEXIWISVGOP-UHFFFAOYSA-N 0.000 description 2
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
• SSZKGJHMQYVGOZ-UHFFFAOYSA-N 8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4CCCC=4C=3)I)=NC2=C1N SSZKGJHMQYVGOZ-UHFFFAOYSA-N 0.000 description 2
• LHLCREWLMOTZJB-UHFFFAOYSA-N 8-[[7-(dimethylamino)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound CN(C)c1cc2OCCOc2cc1Sc1nc2c(N)ncnc2n1CCC1CCCN(C1)S(C)(=O)=O LHLCREWLMOTZJB-UHFFFAOYSA-N 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
• 101100021265 Caenorhabditis elegans lin-5 gene Proteins 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• 108010061414 Hepatocyte Nuclear Factor 1-beta Proteins 0.000 description 2
• 102100022123 Hepatocyte nuclear factor 1-beta Human genes 0.000 description 2
• 101000701815 Homo sapiens Spermidine synthase Proteins 0.000 description 2
• 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 2
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 2
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
• 102100029469 WD repeat and HMG-box DNA-binding protein 1 Human genes 0.000 description 2
• 101710097421 WD repeat and HMG-box DNA-binding protein 1 Proteins 0.000 description 2
• IUEPVMMFUSDDBJ-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]pyrazol-4-yl]boronic acid Chemical compound CC(C)(C)OC(=O)N1C=C(B(O)O)C=N1 IUEPVMMFUSDDBJ-UHFFFAOYSA-N 0.000 description 2
• 125000002877 alkyl aryl group Chemical group 0.000 description 2
• 239000012300 argon atmosphere Substances 0.000 description 2
• 239000012298 atmosphere Substances 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• 230000008499 blood brain barrier function Effects 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 238000004891 communication Methods 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• 238000005859 coupling reaction Methods 0.000 description 2
• 230000037029 cross reaction Effects 0.000 description 2
• LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 2
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 238000004896 high resolution mass spectrometry Methods 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
• 229910052698 phosphorus Inorganic materials 0.000 description 2
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 2
• FLKRMXAWABTWSH-UHFFFAOYSA-N piperidine-1-sulfonamide Chemical compound NS(=O)(=O)N1CCCCC1 FLKRMXAWABTWSH-UHFFFAOYSA-N 0.000 description 2
• 229960005235 piperonyl butoxide Drugs 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 description 2
• FGDZQCVHDSGLHJ-UHFFFAOYSA-M rubidium chloride Chemical compound [Cl-].[Rb+] FGDZQCVHDSGLHJ-UHFFFAOYSA-M 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
• 238000001228 spectrum Methods 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• 238000002560 therapeutic procedure Methods 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• 101150011513 yrrT gene Proteins 0.000 description 2
• QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 1
• VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 1
• VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 1
• MNJYZNVROSZZQC-UHFFFAOYSA-N (4-tert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC=C(B(O)O)C=C1 MNJYZNVROSZZQC-UHFFFAOYSA-N 0.000 description 1
• APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
• JNVXRQOSRUDXDY-UHFFFAOYSA-N 1,1-diiodoethane Chemical compound CC(I)I JNVXRQOSRUDXDY-UHFFFAOYSA-N 0.000 description 1
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
• RQMXOMCWRSEQQC-UHFFFAOYSA-N 1,4-dioxine-2-carbonitrile Chemical compound N#CC1=COC=CO1 RQMXOMCWRSEQQC-UHFFFAOYSA-N 0.000 description 1
• HGVWMTAIIYNQSI-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone Chemical compound O1CCOC2=CC(C(=O)C)=CC=C21 HGVWMTAIIYNQSI-UHFFFAOYSA-N 0.000 description 1
• LKRJUEMIWFNXLK-UHFFFAOYSA-N 1-[3-[2-[6-amino-2-fluoro-8-[[6-(1h-pyrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1CCN1C2=NC(F)=NC(N)=C2N=C1CC(C(=C1)C=2NN=CC=2)=CC2=C1OCCO2 LKRJUEMIWFNXLK-UHFFFAOYSA-N 0.000 description 1
• UPIHLCUPAUYKDO-UHFFFAOYSA-N 1-[3-[2-[6-amino-8-[(7-ethynyl-2,3-dihydro-1,4-benzodioxin-6-yl)sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C#C)=CC2=C1OCCO2 UPIHLCUPAUYKDO-UHFFFAOYSA-N 0.000 description 1
• OHRKTDQHSGQTIR-UHFFFAOYSA-N 1-[3-[2-[6-amino-8-[[3-(1,3-oxazol-2-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC(CCn2c(Sc3cc4CCCCc4cc3-c3ncco3)nc3c(N)ncnc23)C1 OHRKTDQHSGQTIR-UHFFFAOYSA-N 0.000 description 1
• MQGYRZIAJUUYMJ-UHFFFAOYSA-N 1-[3-[2-[6-amino-8-[[3-(1H-pyrazol-5-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC(CCn2c(Sc3cc4CCCCc4cc3-c3cc[nH]n3)nc3c(N)ncnc23)C1 MQGYRZIAJUUYMJ-UHFFFAOYSA-N 0.000 description 1
• OSPPUUGTEUJERA-UHFFFAOYSA-N 1-[3-[2-[6-amino-8-[[3-(5-methylfuran-2-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C=2OC(C)=CC=2)=CC2=C1CCCC2 OSPPUUGTEUJERA-UHFFFAOYSA-N 0.000 description 1
• LEQRHKWPGZQONF-UHFFFAOYSA-N 1-[3-[2-[6-amino-8-[[6-(1,3-oxazol-2-yl)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C=2OC=CN=2)=CC2=C1OCC2 LEQRHKWPGZQONF-UHFFFAOYSA-N 0.000 description 1
• NUDTYZDZJYLDSD-UHFFFAOYSA-N 1-[3-[2-[6-amino-8-[[6-(1H-pyrazol-5-yl)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC(CCn2c(Sc3cc4CCOc4cc3-c3cc[nH]n3)nc3c(N)ncnc23)C1 NUDTYZDZJYLDSD-UHFFFAOYSA-N 0.000 description 1
• FWDCBLRZKPKBGC-UHFFFAOYSA-N 1-[3-[2-[6-amino-8-[[6-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1h-inden-5-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C=2OC(C)=CN=2)=CC2=C1CCC2 FWDCBLRZKPKBGC-UHFFFAOYSA-N 0.000 description 1
• RERKCAPAZUTYPT-UHFFFAOYSA-N 1-[3-[2-[6-amino-8-[[7-(5-methylfuran-2-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound NC1=C2N=C(N(C2=NC=N1)CCC1CN(CCC1)C(C)=O)SC1=CC2=C(OCCO2)C=C1C=1OC(=CC1)C RERKCAPAZUTYPT-UHFFFAOYSA-N 0.000 description 1
• KPODTUBWSZCXIG-UHFFFAOYSA-N 1-[3-[2-[6-amino-8-[[7-(ethylamino)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound CCNC1=CC=2OCCOC=2C=C1SC1=NC2=C(N)N=CN=C2N1CCC1CCCN(C(C)=O)C1 KPODTUBWSZCXIG-UHFFFAOYSA-N 0.000 description 1
• KSBNFTJNMCNANC-UHFFFAOYSA-N 1-[3-[6-amino-8-[(3-iodo-5,6,7,8-tetrahydronaphthalen-2-yl)sulfanyl]purin-9-yl]propyl]pyrrolidin-3-one Chemical compound C=1C=2CCCCC=2C=C(I)C=1SC1=NC=2C(N)=NC=NC=2N1CCCN1CCC(=O)C1 KSBNFTJNMCNANC-UHFFFAOYSA-N 0.000 description 1
• KHPOMEQGYGEBAP-UHFFFAOYSA-N 1-[3-[6-amino-8-[[6-(4-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1h-inden-5-yl]sulfanyl]purin-9-yl]propyl]pyrrolidin-3-one Chemical compound CC1=COC(C=2C(=CC=3CCCC=3C=2)SC=2N(C3=NC=NC(N)=C3N=2)CCCN2CC(=O)CC2)=N1 KHPOMEQGYGEBAP-UHFFFAOYSA-N 0.000 description 1
• UPZAPHPORZUWBA-UHFFFAOYSA-N 1-[4-[2-[6-amino-2-chloro-8-[[6-(furan-2-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCC(CCn2c(Cc3cc4OCCOc4cc3-c3ccco3)nc3c(N)nc(Cl)nc23)CC1 UPZAPHPORZUWBA-UHFFFAOYSA-N 0.000 description 1
• ROLYDQLYIMJAIV-UHFFFAOYSA-N 1-[4-[2-[6-amino-2-fluoro-8-[[5-methoxy-2-(5-methylfuran-2-yl)phenyl]methyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound COc1ccc(-c2ccc(C)o2)c(Cc2nc3c(N)nc(F)nc3n2CCC2CCN(CC2)C(C)=O)c1 ROLYDQLYIMJAIV-UHFFFAOYSA-N 0.000 description 1
• ZXYKUJUXTUBDLC-UHFFFAOYSA-N 1-[4-[2-[6-amino-2-fluoro-8-[[6-(1h-pyrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1CCN1C2=NC(F)=NC(N)=C2N=C1CC(C(=C1)C=2NN=CC=2)=CC2=C1OCCO2 ZXYKUJUXTUBDLC-UHFFFAOYSA-N 0.000 description 1
• BXWDDFYSANBWLH-UHFFFAOYSA-N 1-[4-[2-[6-amino-8-[(6-cyclopropyl-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]-2-fluoropurin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1CCN1C2=NC(F)=NC(N)=C2N=C1CC(C(=C1)C2CC2)=CC2=C1OCCO2 BXWDDFYSANBWLH-UHFFFAOYSA-N 0.000 description 1
• VKPJGMJPUDDXOX-UHFFFAOYSA-N 1-[4-[2-[6-amino-8-[(7-cyclopropyl-2,3-dihydro-1,4-benzodioxin-6-yl)sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound NC1=C2N=C(N(C2=NC=N1)CCC1CCN(CC1)C(C)=O)SC1=CC2=C(OCCO2)C=C1C1CC1 VKPJGMJPUDDXOX-UHFFFAOYSA-N 0.000 description 1
• DVPUQNJCKNMDNU-UHFFFAOYSA-N 1-[4-[2-[6-amino-8-[2-[5-(aminomethyl)furan-2-yl]-5-methoxyphenyl]sulfanylpurin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound COc1ccc(-c2ccc(CN)o2)c(Sc2nc3c(N)ncnc3n2CCC2CCN(CC2)C(C)=O)c1 DVPUQNJCKNMDNU-UHFFFAOYSA-N 0.000 description 1
• PJTYPDPBEAVGGJ-UHFFFAOYSA-N 1-[4-[2-[6-amino-8-[[6-(dimethylamino)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound CN(C)C1=CC=2OCCC=2C=C1SC1=NC2=C(N)N=CN=C2N1CCC1CCN(C(C)=O)CC1 PJTYPDPBEAVGGJ-UHFFFAOYSA-N 0.000 description 1
• AWPRXHGVQFMZNI-UHFFFAOYSA-N 1-[4-[2-[6-amino-8-[[7-(5-methylfuran-2-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCC(CCn2c(Sc3cc4OCCOc4cc3-c3ccc(C)o3)nc3c(N)ncnc23)CC1 AWPRXHGVQFMZNI-UHFFFAOYSA-N 0.000 description 1
• DZXQJDGICODJAV-UHFFFAOYSA-N 1-[6-[6-amino-9-[3-(propan-2-ylamino)propyl]purin-8-yl]sulfanyl-5-iodo-2,3-dihydroindol-1-yl]ethanone Chemical compound CC(C)NCCCn1c(Sc2cc3N(CCc3cc2I)C(C)=O)nc2c(N)ncnc12 DZXQJDGICODJAV-UHFFFAOYSA-N 0.000 description 1
• NCZYUYLAYVMACN-UHFFFAOYSA-N 1-[6-amino-8-(2-ethynyl-5-methoxyphenyl)sulfanylpurin-9-yl]-3-(propan-2-ylamino)propan-2-ol Chemical compound COC1=CC=C(C#C)C(SC=2N(C3=NC=NC(N)=C3N=2)CC(O)CNC(C)C)=C1 NCZYUYLAYVMACN-UHFFFAOYSA-N 0.000 description 1
• DROZQIGPUVFXQV-UHFFFAOYSA-N 1-[6-amino-8-(5-methoxy-2-thiophen-2-ylphenyl)sulfanylpurin-9-yl]-3-(propan-2-ylamino)propan-2-ol Chemical compound N=1C2=C(N)N=CN=C2N(CC(O)CNC(C)C)C=1SC1=CC(OC)=CC=C1C1=CC=CS1 DROZQIGPUVFXQV-UHFFFAOYSA-N 0.000 description 1
• QYCLREBFBJUMDT-UHFFFAOYSA-N 1-[6-amino-8-[(6-iodo-3,4-dihydro-2H-chromen-7-yl)sulfanyl]purin-9-yl]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)Cn1c(Sc2cc3OCCCc3cc2I)nc2c(N)ncnc12 QYCLREBFBJUMDT-UHFFFAOYSA-N 0.000 description 1
• SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
• ZHKJHQBOAJQXQR-UHFFFAOYSA-N 1H-azirine Chemical compound N1C=C1 ZHKJHQBOAJQXQR-UHFFFAOYSA-N 0.000 description 1
• HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
• OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
• BZKOZYWGZKRTIB-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-amine Chemical compound O1CCOC2=CC(N)=CC=C21 BZKOZYWGZKRTIB-UHFFFAOYSA-N 0.000 description 1
• LEWZOBYWGWKNCK-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-amine Chemical compound NC1=CC=C2CCCC2=C1 LEWZOBYWGWKNCK-UHFFFAOYSA-N 0.000 description 1
• MFZBSWSCIWCRKS-UHFFFAOYSA-N 2,9-dimethyl-1,10-phenanthroline;hydrate Chemical compound O.C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1 MFZBSWSCIWCRKS-UHFFFAOYSA-N 0.000 description 1
• SFVHZPMQGRFPMM-UHFFFAOYSA-N 2-(1-benzofuran-6-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C=COC2=C1 SFVHZPMQGRFPMM-UHFFFAOYSA-N 0.000 description 1
• BVRNERFWPQRVJB-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)acetic acid Chemical compound O1CCOC2=CC(CC(=O)O)=CC=C21 BVRNERFWPQRVJB-UHFFFAOYSA-N 0.000 description 1
• HBAUAIPLAXNUIM-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-6-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2CCOC2=C1 HBAUAIPLAXNUIM-UHFFFAOYSA-N 0.000 description 1
• VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
• GRSINHCNTVNOCS-UHFFFAOYSA-N 2-[2-(2-methylpropylamino)ethyl]-7H-purin-6-amine Chemical compound C(C(C)C)NCCC1=NC(=C2N=CNC2=N1)N GRSINHCNTVNOCS-UHFFFAOYSA-N 0.000 description 1
• SLTIXJAJFQEDCR-UHFFFAOYSA-N 2-[6-amino-9-[3-(propan-2-ylamino)propyl]purin-8-yl]sulfanyl-4-methoxybenzonitrile Chemical compound NC1=C2N=C(N(C2=NC=N1)CCCNC(C)C)SC1=C(C#N)C=CC(=C1)OC SLTIXJAJFQEDCR-UHFFFAOYSA-N 0.000 description 1
• BFYZIJFYOVRILS-UHFFFAOYSA-N 2-[[6-amino-2-fluoro-9-[3-(propan-2-ylamino)propyl]purin-8-yl]methyl]-4-methoxybenzonitrile Chemical compound NC1=C2N=C(N(C2=NC(=N1)F)CCCNC(C)C)CC1=C(C#N)C=CC(=C1)OC BFYZIJFYOVRILS-UHFFFAOYSA-N 0.000 description 1
• PKWNDMMUPCRIIY-UHFFFAOYSA-N 2-chloro-8-[(5-ethynyl-2,3-dihydro-1-benzofuran-6-yl)methyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=C(Cl)N=C2N(CCNCC(C)C)C(CC=3C(=CC=4CCOC=4C=3)C#C)=NC2=C1N PKWNDMMUPCRIIY-UHFFFAOYSA-N 0.000 description 1
• FTRMFEBGXXDTPT-UHFFFAOYSA-N 2-chloro-8-[(6-ethynyl-2,3-dihydro-1h-inden-5-yl)methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=C(Cl)N=C2N(CCCNC(C)C)C(CC=3C(=CC=4CCCC=4C=3)C#C)=NC2=C1N FTRMFEBGXXDTPT-UHFFFAOYSA-N 0.000 description 1
• XZXKBKPDQCCYGG-UHFFFAOYSA-N 2-chloro-8-[(6-iodo-2,3-dihydro-1h-indol-5-yl)methyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=C(Cl)N=C2N(CCNCC(C)C)C(CC=3C(=CC=4NCCC=4C=3)I)=NC2=C1N XZXKBKPDQCCYGG-UHFFFAOYSA-N 0.000 description 1
• MEESSRQRYLAUBS-UHFFFAOYSA-N 2-chloro-8-[[3-(furan-2-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound ClC1=NC(=C2N=C(N(C2=N1)CCCNC(C)C)CC1=CC=2CCCCC=2C=C1C=1OC=CC=1)N MEESSRQRYLAUBS-UHFFFAOYSA-N 0.000 description 1
• HPPOMIJIDVIMTQ-UHFFFAOYSA-N 2-chloro-8-[[5-(5-methylfuran-2-yl)-2,3-dihydro-1-benzofuran-6-yl]methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound CC(C)NCCCn1c(Cc2cc3OCCc3cc2-c2ccc(C)o2)nc2c(N)nc(Cl)nc12 HPPOMIJIDVIMTQ-UHFFFAOYSA-N 0.000 description 1
• LTKBZFAYPFBCCQ-UHFFFAOYSA-N 2-chloro-8-[[6-(furan-2-yl)-2,3-dihydro-1H-inden-5-yl]methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound ClC1=NC(=C2N=C(N(C2=N1)CCCNC(C)C)CC=1C=C2CCCC2=CC1C=1OC=CC1)N LTKBZFAYPFBCCQ-UHFFFAOYSA-N 0.000 description 1
• YDLRCBVDCGGSTC-UHFFFAOYSA-N 2-chloro-9-[2-(2-methylpropylamino)ethyl]-8-[(6-pyrrolidin-1-yl-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(Cl)N=C2N(CCNCC(C)C)C=1CC1=CC=2OCCOC=2C=C1N1CCCC1 YDLRCBVDCGGSTC-UHFFFAOYSA-N 0.000 description 1
• APTVTOQHTTZZOB-UHFFFAOYSA-N 2-fluoro-8-[(5-iodo-2,3-dihydro-1-benzofuran-6-yl)methyl]-7h-purin-6-amine Chemical compound N=1C=2C(N)=NC(F)=NC=2NC=1CC(C(=C1)I)=CC2=C1CCO2 APTVTOQHTTZZOB-UHFFFAOYSA-N 0.000 description 1
• BCQCHTGXLYCEAP-UHFFFAOYSA-N 2-fluoro-8-[(5-iodo-2,3-dihydro-1-benzofuran-6-yl)methyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=C(F)N=C2N(CCNCC(C)C)C(CC=3C(=CC=4CCOC=4C=3)I)=NC2=C1N BCQCHTGXLYCEAP-UHFFFAOYSA-N 0.000 description 1
• NDJSGZXZPFMUSO-UHFFFAOYSA-N 2-fluoro-8-[(5-iodo-2,3-dihydro-1-benzofuran-6-yl)methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=C(F)N=C2N(CCCNC(C)C)C(CC=3C(=CC=4CCOC=4C=3)I)=NC2=C1N NDJSGZXZPFMUSO-UHFFFAOYSA-N 0.000 description 1
• IMBUXATZJUIFLD-UHFFFAOYSA-N 2-fluoro-8-[(5-iodo-2,3-dihydro-1-benzothiophen-6-yl)methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=C(F)N=C2N(CCCNC(C)C)C(CC=3C(=CC=4CCSC=4C=3)I)=NC2=C1N IMBUXATZJUIFLD-UHFFFAOYSA-N 0.000 description 1
• KFNRYMVVPGSPMU-UHFFFAOYSA-N 2-fluoro-8-[(5-methoxy-2-thiophen-2-ylphenyl)methyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCNCC(C)C)C=1CC1=CC(OC)=CC=C1C1=CC=CS1 KFNRYMVVPGSPMU-UHFFFAOYSA-N 0.000 description 1
• HEOKCSNULQGUDC-UHFFFAOYSA-N 2-fluoro-8-[(6-iodo-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]-7h-purin-6-amine Chemical compound O1CCOC(C=C2I)=C1C=C2CC(N1)=NC2=C1N=C(F)N=C2N HEOKCSNULQGUDC-UHFFFAOYSA-N 0.000 description 1
• RKKNHSJUEDMOPU-UHFFFAOYSA-N 2-fluoro-8-[(6-iodo-2,3-dihydro-1-benzofuran-5-yl)methyl]-9-[2-(1-methylsulfonylpyrrolidin-3-yl)ethyl]purin-6-amine Chemical compound FC1=NC(=C2N=C(N(C2=N1)CCC1CN(CC1)S(=O)(=O)C)CC=1C(=CC2=C(CCO2)C1)I)N RKKNHSJUEDMOPU-UHFFFAOYSA-N 0.000 description 1
• FMRQQAUFTXAXOX-UHFFFAOYSA-N 2-fluoro-8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)methyl]-9-[2-(1-methylpiperidin-2-yl)ethyl]purin-6-amine Chemical compound CN1CCCCC1CCN1C2=NC(F)=NC(N)=C2N=C1CC(C(=C1)I)=CC2=C1CCC2 FMRQQAUFTXAXOX-UHFFFAOYSA-N 0.000 description 1
• SPQNBAJLFLRLJF-UHFFFAOYSA-N 2-fluoro-8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)methyl]-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound C1N(S(=O)(=O)C)CCCC1CCN1C2=NC(F)=NC(N)=C2N=C1CC(C(=C1)I)=CC2=C1CCC2 SPQNBAJLFLRLJF-UHFFFAOYSA-N 0.000 description 1
• LLYSOLHUCYZKNG-UHFFFAOYSA-N 2-fluoro-8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)methyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=C(F)N=C2N(CCNCC(C)C)C(CC=3C(=CC=4CCCC=4C=3)I)=NC2=C1N LLYSOLHUCYZKNG-UHFFFAOYSA-N 0.000 description 1
• RNQVDWGZNRPBJQ-UHFFFAOYSA-N 2-fluoro-8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=C(F)N=C2N(CCCNC(C)C)C(CC=3C(=CC=4CCCC=4C=3)I)=NC2=C1N RNQVDWGZNRPBJQ-UHFFFAOYSA-N 0.000 description 1
• UQGPUDCDLHWTHC-UHFFFAOYSA-N 2-fluoro-8-[[5-methoxy-2-(1,2-oxazol-4-yl)phenyl]methyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound COc1ccc(-c2cnoc2)c(Cc2nc3c(N)nc(F)nc3n2CCNCC(C)C)c1 UQGPUDCDLHWTHC-UHFFFAOYSA-N 0.000 description 1
• SXDAACNQLNMFEL-UHFFFAOYSA-N 2-fluoro-8-[[6-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCCNC(C)C)C=1CC1=CC=2OCCOC=2C=C1C1=NC=CO1 SXDAACNQLNMFEL-UHFFFAOYSA-N 0.000 description 1
• WIBRTKIPORDXSV-UHFFFAOYSA-N 2-fluoro-8-[[6-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCCNC(C)C)C=1CC1=CC=2OCCOC=2C=C1C1=NC=C(C)O1 WIBRTKIPORDXSV-UHFFFAOYSA-N 0.000 description 1
• DJRAHOMUECSKSG-UHFFFAOYSA-N 2-fluoro-8-[[6-(5-methylfuran-2-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound CC(C)CNCCn1c(Cc2cc3OCCOc3cc2-c2ccc(C)o2)nc2c(N)nc(F)nc12 DJRAHOMUECSKSG-UHFFFAOYSA-N 0.000 description 1
• OOKRPTWEQVSCDE-UHFFFAOYSA-N 2-fluoro-8-[[6-(furan-2-yl)-1-benzothiophen-5-yl]methyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound FC1=NC(=C2N=C(N(C2=N1)CCCNC(C)C)CC1=CC2=C(SC=C2)C=C1C=1OC=CC1)N OOKRPTWEQVSCDE-UHFFFAOYSA-N 0.000 description 1
• KOMHXZUPKHZEBA-UHFFFAOYSA-N 2-fluoro-8-[[6-(furan-2-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCNCC(C)C)C=1CC1=CC=2OCCOC=2C=C1C1=CC=CO1 KOMHXZUPKHZEBA-UHFFFAOYSA-N 0.000 description 1
• RXYROHNFNCMLEP-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]-8-[(1-methyl-6-pyrrolidin-1-yl-3,4-dihydro-2H-quinolin-7-yl)methyl]purin-6-amine Chemical compound FC1=NC(=C2N=C(N(C2=N1)CCNCC(C)C)CC1=C(C=C2CCCN(C2=C1)C)N1CCCC1)N RXYROHNFNCMLEP-UHFFFAOYSA-N 0.000 description 1
• YZUMOFJLBCWSOY-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]-8-[(6-thiophen-2-yl-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]purin-6-amine Chemical compound FC1=NC(=C2N=C(N(C2=N1)CCNCC(C)C)CC1=CC2=C(OCCO2)C=C1C=1SC=CC=1)N YZUMOFJLBCWSOY-UHFFFAOYSA-N 0.000 description 1
• YKDMHDHNBIRJDO-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]-8-[(6-thiophen-3-yl-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]purin-6-amine Chemical compound FC1=NC(=C2N=C(N(C2=N1)CCNCC(C)C)CC1=CC2=C(OCCO2)C=C1C1=CSC=C1)N YKDMHDHNBIRJDO-UHFFFAOYSA-N 0.000 description 1
• AJLLYQFEZSGBOI-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]-8-[(7-pyrrolidin-1-yl-1,2,3,4-tetrahydroquinolin-6-yl)methyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCNCC(C)C)C=1CC1=CC=2CCCNC=2C=C1N1CCCC1 AJLLYQFEZSGBOI-UHFFFAOYSA-N 0.000 description 1
• KNTDVDXGMWNTSB-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]-8-[(7-pyrrolidin-1-yl-2,3-dihydro-1,4-benzoxathiin-6-yl)methyl]purin-6-amine Chemical compound FC1=NC(=C2N=C(N(C2=N1)CCNCC(C)C)CC1=CC2=C(OCCS2)C=C1N1CCCC1)N KNTDVDXGMWNTSB-UHFFFAOYSA-N 0.000 description 1
• MGHHXQKKRILVGV-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]-8-[[6-(1h-pyrazol-4-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCNCC(C)C)C=1CC1=CC=2OCCOC=2C=C1C=1C=NNC=1 MGHHXQKKRILVGV-UHFFFAOYSA-N 0.000 description 1
• YMBJWEMHCASNCN-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]-8-[[6-(1h-pyrrol-3-yl)-1-benzothiophen-5-yl]methyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCNCC(C)C)C=1CC1=CC=2C=CSC=2C=C1C=1C=CNC=1 YMBJWEMHCASNCN-UHFFFAOYSA-N 0.000 description 1
• FAHQGJGOGNXSMF-UHFFFAOYSA-N 2-fluoro-9-[2-(2-methylpropylamino)ethyl]-8-[[6-(propan-2-ylamino)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-6-amine Chemical compound FC1=NC(=C2N=C(N(C2=N1)CCNCC(C)C)CC1=CC2=C(OCCO2)C=C1NC(C)C)N FAHQGJGOGNXSMF-UHFFFAOYSA-N 0.000 description 1
• UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
• VPOBKLPLJLKYPO-UHFFFAOYSA-N 3-[2-[6-amino-8-[[6-(1H-pyrazol-5-yl)-2,3-dihydro-1H-inden-5-yl]sulfanyl]purin-9-yl]ethyl]piperidine-1-carbaldehyde Chemical compound Nc1ncnc2n(CCC3CCCN(C3)C=O)c(Sc3cc4CCCc4cc3-c3cc[nH]n3)nc12 VPOBKLPLJLKYPO-UHFFFAOYSA-N 0.000 description 1
• ACKXKWUWHXJEDA-UHFFFAOYSA-N 3-[6-amino-9-[3-(propan-2-ylamino)propyl]purin-8-yl]sulfanyl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile Chemical compound NC1=C2N=C(N(C2=NC=N1)CCCNC(C)C)SC=1C(=CC=2CCCCC=2C=1)C#N ACKXKWUWHXJEDA-UHFFFAOYSA-N 0.000 description 1
• FVMDYYGIDFPZAX-UHFFFAOYSA-N 3-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=CC(O)=C1 FVMDYYGIDFPZAX-UHFFFAOYSA-N 0.000 description 1
• KAOTXIGLMDOHJJ-UHFFFAOYSA-N 3-iodonaphthalen-2-amine Chemical compound C1=CC=C2C=C(I)C(N)=CC2=C1 KAOTXIGLMDOHJJ-UHFFFAOYSA-N 0.000 description 1
• PLHJCCHSCFNKCC-UHFFFAOYSA-N 3-methylpent-1-yne Chemical group CCC(C)C#C PLHJCCHSCFNKCC-UHFFFAOYSA-N 0.000 description 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• UNTNRNUQVKDIPV-UHFFFAOYSA-N 3h-dithiazole Chemical compound N1SSC=C1 UNTNRNUQVKDIPV-UHFFFAOYSA-N 0.000 description 1
• SLKTYXFCYMDNID-UHFFFAOYSA-N 4-[2-[6-amino-2-chloro-8-[[6-(1,2-oxazol-4-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-9-yl]ethyl]piperidine-1-carbaldehyde Chemical compound C=1C=2OCCOC=2C=C(C2=CON=C2)C=1CC1=NC=2C(N)=NC(Cl)=NC=2N1CCC1CCN(C=O)CC1 SLKTYXFCYMDNID-UHFFFAOYSA-N 0.000 description 1
• WREWDEMQVZQKOJ-UHFFFAOYSA-N 4-[2-[6-amino-8-[(6-ethynyl-4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)sulfanyl]purin-9-yl]ethyl]piperidine-1-carbaldehyde Chemical compound NC1=C2N=C(N(C2=NC=N1)CCC1CCN(CC1)C=O)SC=1C(=CC2=C(OCCN2C)C=1)C#C WREWDEMQVZQKOJ-UHFFFAOYSA-N 0.000 description 1
• DCHQWGGBFQSJEX-UHFFFAOYSA-N 4-[2-[6-amino-8-[(7-thiophen-3-yl-2,3-dihydro-1,4-benzodioxin-6-yl)sulfanyl]purin-9-yl]ethyl]piperidine-1-carbaldehyde Chemical compound Nc1ncnc2n(CCC3CCN(CC3)C=O)c(Sc3cc4OCCOc4cc3-c3ccsc3)nc12 DCHQWGGBFQSJEX-UHFFFAOYSA-N 0.000 description 1
• OQUNQUNFBBMQLT-UHFFFAOYSA-N 4-[2-[6-amino-8-[[6-(furan-2-yl)-4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl]sulfanyl]purin-9-yl]ethyl]piperidine-1-carbaldehyde Chemical compound C=1C=COC=1C=1C=C2N(C)CCOC2=CC=1SC1=NC2=C(N)N=CN=C2N1CCC1CCN(C=O)CC1 OQUNQUNFBBMQLT-UHFFFAOYSA-N 0.000 description 1
• YUPZQRUUSZQMJT-UHFFFAOYSA-N 4-[2-[6-amino-8-[[7-(furan-2-yl)-1-methyl-3,4-dihydro-2h-quinolin-6-yl]sulfanyl]purin-9-yl]ethyl]piperidine-1-carbaldehyde Chemical compound C=1C=COC=1C=1C=C2N(C)CCCC2=CC=1SC1=NC2=C(N)N=CN=C2N1CCC1CCN(C=O)CC1 YUPZQRUUSZQMJT-UHFFFAOYSA-N 0.000 description 1
• ZTBQQMRMUWBAOB-UHFFFAOYSA-N 4-methyl-2,3-dihydro-1,4-benzoxazin-6-amine Chemical compound C1=C(N)C=C2N(C)CCOC2=C1 ZTBQQMRMUWBAOB-UHFFFAOYSA-N 0.000 description 1
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
• YQGADULPCIXSJV-UHFFFAOYSA-N 5-iodo-2,3-dihydro-1-benzofuran-6-amine Chemical compound C1=C(I)C(N)=CC2=C1CCO2 YQGADULPCIXSJV-UHFFFAOYSA-N 0.000 description 1
• XGGFGVBDRQQERB-UHFFFAOYSA-N 6-[6-amino-9-[2-(2-methylpropylamino)ethyl]purin-8-yl]sulfanyl-5-iodo-2,3-dihydroinden-1-one Chemical compound N1=CN=C2N(CCNCC(C)C)C(SC=3C(=CC=4CCC(=O)C=4C=3)I)=NC2=C1N XGGFGVBDRQQERB-UHFFFAOYSA-N 0.000 description 1
• GYNZCMPPAAIVND-UHFFFAOYSA-N 6-[6-amino-9-[2-(2-methylpropylamino)ethyl]purin-8-yl]sulfanyl-5-iodo-2,3-dihydroindene-1-thione Chemical compound CC(C)CNCCn1c(Sc2cc3C(=S)CCc3cc2I)nc2c(N)ncnc12 GYNZCMPPAAIVND-UHFFFAOYSA-N 0.000 description 1
• DRWASPXCHAZFAI-UHFFFAOYSA-N 6-[6-amino-9-[3-(propan-2-ylamino)propyl]purin-8-yl]sulfanyl-2,3-dihydro-1h-indole-5-carbonitrile Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4CCNC=4C=3)C#N)=NC2=C1N DRWASPXCHAZFAI-UHFFFAOYSA-N 0.000 description 1
• GFWXKEOIVDAOBG-UHFFFAOYSA-N 6-[6-amino-9-[3-(propan-2-ylamino)propyl]purin-8-yl]sulfanyl-5-cyclopropyl-2,3-dihydroinden-1-one Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2C(=O)CCC=2C=C1C1CC1 GFWXKEOIVDAOBG-UHFFFAOYSA-N 0.000 description 1
• LZZBEUQNJFBTEZ-UHFFFAOYSA-N 6-[6-amino-9-[3-(propan-2-ylamino)propyl]purin-8-yl]sulfanyl-5-iodo-2,3-dihydroinden-1-one Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4CCC(=O)C=4C=3)I)=NC2=C1N LZZBEUQNJFBTEZ-UHFFFAOYSA-N 0.000 description 1
• ZFXQTYAHIQFBNG-UHFFFAOYSA-N 6-[6-amino-9-[3-(tert-butylamino)propyl]purin-8-yl]sulfanyl-5-iodo-2,3-dihydroinden-1-one Chemical compound N1=CN=C2N(CCCNC(C)(C)C)C(SC=3C(=CC=4CCC(=O)C=4C=3)I)=NC2=C1N ZFXQTYAHIQFBNG-UHFFFAOYSA-N 0.000 description 1
• JYZVDGQFWOSVHT-UHFFFAOYSA-N 6-[[6-amino-2-fluoro-9-[2-(2-methylpropylamino)ethyl]purin-8-yl]methyl]-5-ethynyl-2,3-dihydroinden-1-one Chemical compound N1=C(F)N=C2N(CCNCC(C)C)C(CC=3C(=CC=4CCC(=O)C=4C=3)C#C)=NC2=C1N JYZVDGQFWOSVHT-UHFFFAOYSA-N 0.000 description 1
• VYNLYXAINVRGLE-UHFFFAOYSA-N 6-[[6-amino-2-fluoro-9-[3-(propan-2-ylamino)propyl]purin-8-yl]methyl]-2,3-dihydro-1-benzothiophene-5-carbonitrile Chemical compound N1=C(F)N=C2N(CCCNC(C)C)C(CC=3C(=CC=4CCSC=4C=3)C#N)=NC2=C1N VYNLYXAINVRGLE-UHFFFAOYSA-N 0.000 description 1
• HZTMYTXWFHBHDC-UHFFFAOYSA-N 6-iodo-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=CC(I)=CC=C21 HZTMYTXWFHBHDC-UHFFFAOYSA-N 0.000 description 1
• UPHIJLSUBXGZDN-UHFFFAOYSA-N 6-iodo-2,3-dihydro-1h-inden-5-amine Chemical compound C1=C(I)C(N)=CC2=C1CCC2 UPHIJLSUBXGZDN-UHFFFAOYSA-N 0.000 description 1
• WFHLBXBWGXRUFO-UHFFFAOYSA-N 6-iodo-4-methyl-2,3-dihydro-1,4-benzoxazine Chemical compound C1=C(I)C=C2N(C)CCOC2=C1 WFHLBXBWGXRUFO-UHFFFAOYSA-N 0.000 description 1
• HLUYEDQKIFUIIP-UHFFFAOYSA-N 6-nitro-2,3-dihydro-1h-inden-5-amine Chemical compound C1=C([N+]([O-])=O)C(N)=CC2=C1CCC2 HLUYEDQKIFUIIP-UHFFFAOYSA-N 0.000 description 1
• GZAJZBARYACGSO-UHFFFAOYSA-N 6-nitro-3,4-dihydro-2h-1,4-benzoxazine Chemical compound O1CCNC2=CC([N+](=O)[O-])=CC=C21 GZAJZBARYACGSO-UHFFFAOYSA-N 0.000 description 1
• SKNSJXBJCQTNEA-UHFFFAOYSA-N 7-[[6-amino-2-chloro-9-[2-(2-methylpropylamino)ethyl]purin-8-yl]methyl]-2,3-dihydro-1,4-benzodioxine-6-carbonitrile Chemical compound N1=C(Cl)N=C2N(CCNCC(C)C)C(CC=3C(=CC=4OCCOC=4C=3)C#N)=NC2=C1N SKNSJXBJCQTNEA-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• BSOSYDPCRDZIPG-UHFFFAOYSA-N 8-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-2-fluoro-7h-purin-6-amine Chemical compound O1CCOC2=CC(CC=3NC=4N=C(F)N=C(C=4N=3)N)=CC=C21 BSOSYDPCRDZIPG-UHFFFAOYSA-N 0.000 description 1
• MYIXDYQABWOTGD-UHFFFAOYSA-N 8-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-7h-purine-2,6-diamine Chemical compound O1CCOC2=CC(CC3=NC4=C(N)N=C(N=C4N3)N)=CC=C21 MYIXDYQABWOTGD-UHFFFAOYSA-N 0.000 description 1
• IJGNXHMGSHWYMI-UHFFFAOYSA-N 8-(2,3-dihydro-1-benzofuran-6-ylmethyl)-2-fluoro-7h-purin-6-amine Chemical compound C1=C2CCOC2=CC(CC=2NC=3N=C(F)N=C(C=3N=2)N)=C1 IJGNXHMGSHWYMI-UHFFFAOYSA-N 0.000 description 1
• DSPTXZGHDKLHKT-UHFFFAOYSA-N 8-(2,3-dihydro-1-benzofuran-6-ylmethyl)-7h-purine-2,6-diamine Chemical compound C1=C2CCOC2=CC(CC2=NC3=C(N)N=C(N=C3N2)N)=C1 DSPTXZGHDKLHKT-UHFFFAOYSA-N 0.000 description 1
• QBDIWVWILFTKMA-UHFFFAOYSA-N 8-(2,3-dihydro-1-benzofuran-6-ylsulfanyl)-7h-purin-6-amine Chemical compound C1=C2CCOC2=CC(SC=2NC=3N=CN=C(C=3N=2)N)=C1 QBDIWVWILFTKMA-UHFFFAOYSA-N 0.000 description 1
• KLMFUVMHWUPKHW-UHFFFAOYSA-N 8-(2-ethynyl-5-methoxyphenyl)sulfanyl-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound COC1=CC=C(C#C)C(SC=2N(C3=NC=NC(N)=C3N=2)CCNCC(C)C)=C1 KLMFUVMHWUPKHW-UHFFFAOYSA-N 0.000 description 1
• HBTAVDQMKRPVHE-UHFFFAOYSA-N 8-(2-ethynyl-5-methoxyphenyl)sulfanyl-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound COC1=CC=C(C#C)C(SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)C)=C1 HBTAVDQMKRPVHE-UHFFFAOYSA-N 0.000 description 1
• JJMVOSZFKUVWDI-UHFFFAOYSA-N 8-(3-aminonaphthalen-2-yl)sulfanyl-7h-purin-6-amine Chemical compound N1=CN=C2NC(SC3=CC4=CC=CC=C4C=C3N)=NC2=C1N JJMVOSZFKUVWDI-UHFFFAOYSA-N 0.000 description 1
• TYPMZTJRNARGNL-UHFFFAOYSA-N 8-(3-ethynylnaphthalen-2-yl)sulfanyl-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC4=CC=CC=C4C=3)C#C)=NC2=C1N TYPMZTJRNARGNL-UHFFFAOYSA-N 0.000 description 1
• SQLMTMCDBGCHEF-UHFFFAOYSA-N 8-(3-iodonaphthalen-2-yl)sulfanyl-7h-purin-6-amine Chemical compound C1=CC=C2C=C(I)C(SC=3NC=4N=CN=C(C=4N=3)N)=CC2=C1 SQLMTMCDBGCHEF-UHFFFAOYSA-N 0.000 description 1
• KAAKYCMZWOXTJG-UHFFFAOYSA-N 8-(5-methoxy-2-thiophen-3-ylphenyl)sulfanyl-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC(OC)=CC=C1C=1C=CSC=1 KAAKYCMZWOXTJG-UHFFFAOYSA-N 0.000 description 1
• HDSHZLGIUMZWSB-UHFFFAOYSA-N 8-[(3-ethynyl-5,6,7,8-tetrahydronaphthalen-2-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4CCCCC=4C=3)C#C)=NC2=C1N HDSHZLGIUMZWSB-UHFFFAOYSA-N 0.000 description 1
• XTQRXKNWJNNOND-UHFFFAOYSA-N 8-[(3-iodo-5,6,7,8-tetrahydronaphthalen-2-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound IC=1C(=CC=2CCCCC=2C=1)SC=1N(C2=NC=NC(=C2N=1)N)CCCNC(C)C XTQRXKNWJNNOND-UHFFFAOYSA-N 0.000 description 1
• NUUUCQLVMGYZGS-UHFFFAOYSA-N 8-[(4-methyl-6-thiophen-2-yl-2,3-dihydro-1,4-benzoxazin-7-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound C(C)(C)NCCCN1C2=NC=NC(=C2N=C1SC=1C(=CC2=C(OCCN2C)C=1)C=1SC=CC=1)N NUUUCQLVMGYZGS-UHFFFAOYSA-N 0.000 description 1
• YXHHEVCURMCQEO-UHFFFAOYSA-N 8-[(5-ethynyl-1h-indol-6-yl)sulfanyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)C)C(SC=3C(=CC=4C=CNC=4C=3)C#C)=NC2=C1N YXHHEVCURMCQEO-UHFFFAOYSA-N 0.000 description 1
• YXJWGLAMUNDZBL-UHFFFAOYSA-N 8-[(5-ethynyl-2,3-dihydro-1-benzofuran-6-yl)methyl]-2-fluoro-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=C(F)N=C2N(CCNCC(C)C)C(CC=3C(=CC=4CCOC=4C=3)C#C)=NC2=C1N YXJWGLAMUNDZBL-UHFFFAOYSA-N 0.000 description 1
• QZFVWMWGRKKLLQ-UHFFFAOYSA-N 8-[(5-iodo-1-benzofuran-6-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound CC(C)NCCCn1c(Sc2cc3occc3cc2I)nc2c(N)ncnc12 QZFVWMWGRKKLLQ-UHFFFAOYSA-N 0.000 description 1
• PTJPWVWSBBXEOC-UHFFFAOYSA-N 8-[(5-iodo-1-benzothiophen-6-yl)sulfanyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)C)C(SC=3C(=CC=4C=CSC=4C=3)I)=NC2=C1N PTJPWVWSBBXEOC-UHFFFAOYSA-N 0.000 description 1
• LWIYELFYGFDKKQ-UHFFFAOYSA-N 8-[(5-iodo-1-methyl-2,3-dihydroindol-6-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4CCN(C)C=4C=3)I)=NC2=C1N LWIYELFYGFDKKQ-UHFFFAOYSA-N 0.000 description 1
• QTCOVPRGVVTMJX-UHFFFAOYSA-N 8-[(5-iodo-2,3-dihydro-1-benzofuran-6-yl)sulfanyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)C)C(SC=3C(=CC=4CCOC=4C=3)I)=NC2=C1N QTCOVPRGVVTMJX-UHFFFAOYSA-N 0.000 description 1
• MZWFMXHWZJGGMO-UHFFFAOYSA-N 8-[(5-iodo-2,3-dihydro-1-benzofuran-6-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4CCOC=4C=3)I)=NC2=C1N MZWFMXHWZJGGMO-UHFFFAOYSA-N 0.000 description 1
• XJOVJTWGCIDQQC-UHFFFAOYSA-N 8-[(5-iodo-2,3-dihydro-1-benzothiophen-6-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4CCSC=4C=3)I)=NC2=C1N XJOVJTWGCIDQQC-UHFFFAOYSA-N 0.000 description 1
• XPFTXWUUMGLYEB-UHFFFAOYSA-N 8-[(6-amino-2,3-dihydro-1-benzofuran-5-yl)sulfanyl]-7h-purin-6-amine Chemical compound N1=CN=C2NC(SC3=CC=4CCOC=4C=C3N)=NC2=C1N XPFTXWUUMGLYEB-UHFFFAOYSA-N 0.000 description 1
• JGZZQCJAAZNYPG-UHFFFAOYSA-N 8-[(6-cyclobutyl-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]-2-fluoro-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound C1(CCC1)C=1C(=CC2=C(OCCO2)C1)CC=1N(C2=NC(=NC(=C2N1)N)F)CCNCC(C)C JGZZQCJAAZNYPG-UHFFFAOYSA-N 0.000 description 1
• GLEFJNSPLRHGFO-UHFFFAOYSA-N 8-[(6-ethynyl-1,3-benzodioxol-5-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4OCOC=4C=3)C#C)=NC2=C1N GLEFJNSPLRHGFO-UHFFFAOYSA-N 0.000 description 1
• AEKAFBSTUWORMU-UHFFFAOYSA-N 8-[(6-ethynyl-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]-2-fluoro-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound C(#C)C=1C(=CC2=C(OCCO2)C1)CC=1N(C2=NC(=NC(=C2N1)N)F)CCC1CN(CCC1)S(=O)(=O)C AEKAFBSTUWORMU-UHFFFAOYSA-N 0.000 description 1
• STDQCFFHUJXNKM-UHFFFAOYSA-N 8-[(6-ethynyl-2,3-dihydro-1h-inden-5-yl)methyl]-2-fluoro-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=C(F)N=C2N(CCCNC(C)C)C(CC=3C(=CC=4CCCC=4C=3)C#C)=NC2=C1N STDQCFFHUJXNKM-UHFFFAOYSA-N 0.000 description 1
• ZWFYLHNKBFJUAO-UHFFFAOYSA-N 8-[(6-ethynyl-2,3-dihydro-1h-inden-5-yl)sulfanyl]-9-[2-(1-methylpiperidin-2-yl)ethyl]purin-6-amine Chemical compound CN1CCCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C#C)=CC2=C1CCC2 ZWFYLHNKBFJUAO-UHFFFAOYSA-N 0.000 description 1
• YHQSVNZDCAAXBV-UHFFFAOYSA-N 8-[(6-ethynyl-2,3-dihydro-1h-inden-5-yl)sulfanyl]-9-[2-(1-methylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound C1N(C)CCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C#C)=CC2=C1CCC2 YHQSVNZDCAAXBV-UHFFFAOYSA-N 0.000 description 1
• YHLAVTCZFZVGCX-UHFFFAOYSA-N 8-[(6-ethynyl-2,3-dihydro-1h-inden-5-yl)sulfanyl]-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound C1N(S(=O)(=O)C)CCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C#C)=CC2=C1CCC2 YHLAVTCZFZVGCX-UHFFFAOYSA-N 0.000 description 1
• PBADZXDQQDMYCL-UHFFFAOYSA-N 8-[(6-ethynyl-2,3-dihydro-1h-inden-5-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4CCCC=4C=3)C#C)=NC2=C1N PBADZXDQQDMYCL-UHFFFAOYSA-N 0.000 description 1
• OTGVQCGPYKIZSN-UHFFFAOYSA-N 8-[(6-ethynyl-3,4-dihydro-2h-thiochromen-7-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4CCCSC=4C=3)C#C)=NC2=C1N OTGVQCGPYKIZSN-UHFFFAOYSA-N 0.000 description 1
• WQSGPJCMKZBDNJ-UHFFFAOYSA-N 8-[(6-iodo-2,3-dihydro-1,4-benzodioxin-7-yl)sulfanyl]-7h-purin-6-amine Chemical compound O1CCOC(C=C2I)=C1C=C2SC(N1)=NC2=C1N=CN=C2N WQSGPJCMKZBDNJ-UHFFFAOYSA-N 0.000 description 1
• OGVPPEHQZFHZET-UHFFFAOYSA-N 8-[(6-iodo-2,3-dihydro-1,4-benzodioxin-7-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4OCCOC=4C=3)I)=NC2=C1N OGVPPEHQZFHZET-UHFFFAOYSA-N 0.000 description 1
• AGPIGMGCFKFFFQ-UHFFFAOYSA-N 8-[(6-iodo-2,3-dihydro-1-benzofuran-5-yl)sulfanyl]-7h-purin-6-amine Chemical compound N=1C=2C(N)=NC=NC=2NC=1SC(C(=C1)I)=CC2=C1OCC2 AGPIGMGCFKFFFQ-UHFFFAOYSA-N 0.000 description 1
• NUZQGTULLXBAPU-UHFFFAOYSA-N 8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)sulfanyl]-7h-purin-6-amine Chemical compound N=1C=2C(N)=NC=NC=2NC=1SC(C(=C1)I)=CC2=C1CCC2 NUZQGTULLXBAPU-UHFFFAOYSA-N 0.000 description 1
• CULDUFHOZXWPGC-UHFFFAOYSA-N 8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)sulfanyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)C)C(SC=3C(=CC=4CCCC=4C=3)I)=NC2=C1N CULDUFHOZXWPGC-UHFFFAOYSA-N 0.000 description 1
• BKFKGZDLYGZNDB-UHFFFAOYSA-N 8-[(6-iodo-2,3-dihydro-1h-indol-5-yl)sulfanyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)C)C(SC=3C(=CC=4NCCC=4C=3)I)=NC2=C1N BKFKGZDLYGZNDB-UHFFFAOYSA-N 0.000 description 1
• NJUNNPVXVQSUEV-UHFFFAOYSA-N 8-[(7-ethynyl-2,3-dihydro-1,4-benzodioxin-6-yl)sulfanyl]-9-[2-(1-methylpiperidin-2-yl)ethyl]purin-6-amine Chemical compound CN1CCCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C#C)=CC2=C1OCCO2 NJUNNPVXVQSUEV-UHFFFAOYSA-N 0.000 description 1
• OCBAMJRUQRBHKQ-UHFFFAOYSA-N 8-[(7-ethynyl-2,3-dihydro-1,4-benzodioxin-6-yl)sulfanyl]-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound C1N(S(=O)(=O)C)CCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C#C)=CC2=C1OCCO2 OCBAMJRUQRBHKQ-UHFFFAOYSA-N 0.000 description 1
• GAZBXNGSFSYIIK-UHFFFAOYSA-N 8-[(7-ethynyl-2,3-dihydro-1,4-benzoxathiin-6-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4OCCSC=4C=3)C#C)=NC2=C1N GAZBXNGSFSYIIK-UHFFFAOYSA-N 0.000 description 1
• LPKXDAFUMBTXAK-UHFFFAOYSA-N 8-[(7-iodo-2,3-dihydro-1,4-benzoxathiin-6-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4OCCSC=4C=3)I)=NC2=C1N LPKXDAFUMBTXAK-UHFFFAOYSA-N 0.000 description 1
• XSUYWIWBQHYGOR-UHFFFAOYSA-N 8-[(7-iodo-3,4-dihydro-2H-chromen-6-yl)sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4OCCCC=4C=3)I)=NC2=C1N XSUYWIWBQHYGOR-UHFFFAOYSA-N 0.000 description 1
• IFFUEBJXJSVBHL-UHFFFAOYSA-N 8-[2-[5-(aminomethyl)furan-2-yl]-5-methoxyphenyl]sulfanyl-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound NCC1=CC=C(O1)C1=C(C=C(C=C1)OC)SC=1N(C2=NC=NC(=C2N=1)N)CCCNC(C)C IFFUEBJXJSVBHL-UHFFFAOYSA-N 0.000 description 1
• FBFUCSWYZQQTOW-UHFFFAOYSA-N 8-[3-(5-methyl-1,3-oxazol-2-yl)naphthalen-2-yl]sulfanyl-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound O1C(C)=CN=C1C1=CC2=CC=CC=C2C=C1SC1=NC2=C(N)N=CN=C2N1CCC1CN(S(C)(=O)=O)CCC1 FBFUCSWYZQQTOW-UHFFFAOYSA-N 0.000 description 1
• TVNKNXVPDSZRIG-UHFFFAOYSA-N 8-[5-methoxy-2-(1,2-oxazol-4-yl)phenyl]sulfanyl-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound C(C)(C)NCCCN1C2=NC=NC(=C2N=C1SC1=C(C=CC(=C1)OC)C=1C=NOC=1)N TVNKNXVPDSZRIG-UHFFFAOYSA-N 0.000 description 1
• BZBGPUSZYPZVHJ-UHFFFAOYSA-N 8-[5-methoxy-2-(2-phenylethynyl)phenyl]sulfanyl-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound COc1ccc(C#Cc2ccccc2)c(Sc2nc3c(N)ncnc3n2CCCNC(C)C)c1 BZBGPUSZYPZVHJ-UHFFFAOYSA-N 0.000 description 1
• ZIYPFZVRTLLCGW-UHFFFAOYSA-N 8-[5-methoxy-2-(5-methylfuran-2-yl)phenyl]sulfanyl-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound COc1ccc(-c2ccc(C)o2)c(Sc2nc3c(N)ncnc3n2CCC2CCCN(C2)S(C)(=O)=O)c1 ZIYPFZVRTLLCGW-UHFFFAOYSA-N 0.000 description 1
• OJSIRSOQNBUVBR-UHFFFAOYSA-N 8-[5-methoxy-2-(5-methylthiophen-2-yl)phenyl]sulfanyl-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCC2CN(CCC2)S(C)(=O)=O)C=1SC1=CC(OC)=CC=C1C1=CC=C(C)S1 OJSIRSOQNBUVBR-UHFFFAOYSA-N 0.000 description 1
• HQBHYYBULDVODB-UHFFFAOYSA-N 8-[6-(furan-2-yl)-1-methylindol-5-yl]sulfanyl-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2C=CN(C)C=2C=C1C1=CC=CO1 HQBHYYBULDVODB-UHFFFAOYSA-N 0.000 description 1
• XDKWSVYHTXTMQT-UHFFFAOYSA-N 8-[[3-(dimethylamino)-5,6,7,8-tetrahydronaphthalen-2-yl]sulfanyl]-9-[2-(2,2-dimethylpropylamino)ethyl]purin-6-amine Chemical compound CN(C=1C(=CC=2CCCCC=2C=1)SC=1N(C2=NC=NC(=C2N=1)N)CCNCC(C)(C)C)C XDKWSVYHTXTMQT-UHFFFAOYSA-N 0.000 description 1
• ZNGKFDSBGRNRGT-UHFFFAOYSA-N 8-[[5-(azetidin-1-yl)-1-benzofuran-6-yl]sulfanyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCNCC(C)C)C=1SC1=CC=2OC=CC=2C=C1N1CCC1 ZNGKFDSBGRNRGT-UHFFFAOYSA-N 0.000 description 1
• GEVDPJAKJKBPCV-UHFFFAOYSA-N 8-[[5-(furan-2-yl)-1-methyl-2,3-dihydroindol-6-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2N(C)CCC=2C=C1C1=CC=CO1 GEVDPJAKJKBPCV-UHFFFAOYSA-N 0.000 description 1
• HMPHCWKSKTWAJL-UHFFFAOYSA-N 8-[[5-(furan-2-yl)-2,3-dihydro-1-benzothiophen-6-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2SCCC=2C=C1C1=CC=CO1 HMPHCWKSKTWAJL-UHFFFAOYSA-N 0.000 description 1
• DWJAASBVGZLXTI-UHFFFAOYSA-N 8-[[6-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1h-inden-5-yl]sulfanyl]-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound O1C(C)=CN=C1C(C(=C1)SC=2N(C3=NC=NC(N)=C3N=2)CCC2CN(CCC2)S(C)(=O)=O)=CC2=C1CCC2 DWJAASBVGZLXTI-UHFFFAOYSA-N 0.000 description 1
• SWPGGAYUTFURMR-UHFFFAOYSA-N 8-[[6-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1h-inden-5-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2CCCC=2C=C1C1=NC=C(C)O1 SWPGGAYUTFURMR-UHFFFAOYSA-N 0.000 description 1
• GKZPTDAGXPRHGO-UHFFFAOYSA-N 8-[[6-(5-methylfuran-2-yl)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound C(C)(C)NCCCN1C2=NC=NC(=C2N=C1SC=1C(=CC2=C(CCO2)C=1)C=1OC(=CC=1)C)N GKZPTDAGXPRHGO-UHFFFAOYSA-N 0.000 description 1
• IJYXAPXQQUNNPH-UHFFFAOYSA-N 8-[[6-(aziridin-1-yl)-2,3-dihydro-1h-inden-5-yl]sulfanyl]-9-[3-(1-methylsulfonylpyrrolidin-3-yl)propyl]purin-6-amine Chemical compound C1N(S(=O)(=O)C)CCC1CCCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)N2CC2)=CC2=C1CCC2 IJYXAPXQQUNNPH-UHFFFAOYSA-N 0.000 description 1
• QBKWGGUJUXOAJI-UHFFFAOYSA-N 8-[[6-(dimethylamino)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound CN(C)C1=CC=2OCCC=2C=C1SC1=NC2=C(N)N=CN=C2N1CCC1CCCN(S(C)(=O)=O)C1 QBKWGGUJUXOAJI-UHFFFAOYSA-N 0.000 description 1
• VTDGIAKKUGATJS-UHFFFAOYSA-N 8-[[6-(furan-2-yl)-1-methyl-2,3-dihydroindol-5-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2CCN(C)C=2C=C1C1=CC=CO1 VTDGIAKKUGATJS-UHFFFAOYSA-N 0.000 description 1
• LXGGEZUWOZFYJJ-UHFFFAOYSA-N 8-[[6-(furan-2-yl)-2,3-dihydro-1,4-benzoxathiin-7-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2OCCSC=2C=C1C1=CC=CO1 LXGGEZUWOZFYJJ-UHFFFAOYSA-N 0.000 description 1
• IMQGFDCXFBQAPC-UHFFFAOYSA-N 8-[[6-(furan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound C1N(S(=O)(=O)C)CCCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)C=2OC=CC=2)=CC2=C1OCC2 IMQGFDCXFBQAPC-UHFFFAOYSA-N 0.000 description 1
• KRXKYEIIXSRGCU-UHFFFAOYSA-N 8-[[6-(furan-2-yl)-2,3-dihydro-1H-inden-5-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound CC(C)NCCCn1c(Sc2cc3CCCc3cc2-c2ccco2)nc2c(N)ncnc12 KRXKYEIIXSRGCU-UHFFFAOYSA-N 0.000 description 1
• MUGGGVXWICQHOU-UHFFFAOYSA-N 8-[[7-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2OCCOC=2C=C1C1=NC=CO1 MUGGGVXWICQHOU-UHFFFAOYSA-N 0.000 description 1
• CLEHINJCGAOGHE-UHFFFAOYSA-N 8-[[7-(1h-imidazol-5-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2OCCOC=2C=C1C1=CN=CN1 CLEHINJCGAOGHE-UHFFFAOYSA-N 0.000 description 1
• UYOVTBUSTPCHKR-UHFFFAOYSA-N 8-[[7-(5-methyl-1h-pyrazol-3-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2OCCOC=2C=C1C=1C=C(C)NN=1 UYOVTBUSTPCHKR-UHFFFAOYSA-N 0.000 description 1
• XOPYRYPWSGYTNS-UHFFFAOYSA-N 8-[[7-(azetidin-1-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]-9-[2-(2-methylpropylamino)ethyl]purin-6-amine Chemical compound N1(CCC1)C=1C(=CC2=C(OCCO2)C=1)SC=1N(C2=NC=NC(=C2N=1)N)CCNCC(C)C XOPYRYPWSGYTNS-UHFFFAOYSA-N 0.000 description 1
• AMHJZMVHWYRESC-UHFFFAOYSA-N 8-[[7-(dimethylamino)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4OCCOC=4C=3)N(C)C)=NC2=C1N AMHJZMVHWYRESC-UHFFFAOYSA-N 0.000 description 1
• SFPHHBCWGMJHDU-UHFFFAOYSA-N 8-[[7-(ethylamino)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]-9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]purin-6-amine Chemical compound CCNC1=CC=2OCCOC=2C=C1SC1=NC2=C(N)N=CN=C2N1CCC1CCCN(S(C)(=O)=O)C1 SFPHHBCWGMJHDU-UHFFFAOYSA-N 0.000 description 1
• AZSXXMOJXHASGY-UHFFFAOYSA-N 8-[[7-(furan-2-yl)-2,3-dihydro-1,4-benzoxathiin-6-yl]sulfanyl]-9-[3-(propan-2-ylamino)propyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2SCCOC=2C=C1C1=CC=CO1 AZSXXMOJXHASGY-UHFFFAOYSA-N 0.000 description 1
• SHQAZVGKHVPSMC-UHFFFAOYSA-N 9-(2-aminoethyl)-2-fluoro-8-[[6-(1h-pyrazol-5-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCN)C=1CC1=CC=2OCCOC=2C=C1C1=CC=NN1 SHQAZVGKHVPSMC-UHFFFAOYSA-N 0.000 description 1
• UYOFMNBRDKMOFB-UHFFFAOYSA-N 9-(2-aminoethyl)-8-[(5-iodo-1-benzofuran-6-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCN)C(SC=3C(=CC=4C=COC=4C=3)I)=NC2=C1N UYOFMNBRDKMOFB-UHFFFAOYSA-N 0.000 description 1
• QRDITXFUELRFTL-UHFFFAOYSA-N 9-(2-aminoethyl)-8-[(6-iodo-1-benzofuran-5-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCN)C(SC=3C(=CC=4OC=CC=4C=3)I)=NC2=C1N QRDITXFUELRFTL-UHFFFAOYSA-N 0.000 description 1
• ZTMCFEKXHPYMKI-UHFFFAOYSA-N 9-(2-aminoethyl)-8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCN)C(SC=3C(=CC=4CCCC=4C=3)I)=NC2=C1N ZTMCFEKXHPYMKI-UHFFFAOYSA-N 0.000 description 1
• SERDKQSFCYHJER-UHFFFAOYSA-N 9-(2-bromoethyl)-2-fluoro-8-[(6-iodo-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]purin-6-amine Chemical compound O1CCOC(C=C2I)=C1C=C2CC(N1CCBr)=NC2=C1N=C(F)N=C2N SERDKQSFCYHJER-UHFFFAOYSA-N 0.000 description 1
• HQDYUQMYJMUVOC-UHFFFAOYSA-N 9-(2-bromoethyl)-8-[(6-iodo-2,3-dihydro-1,4-benzodioxin-7-yl)sulfanyl]purin-6-amine Chemical compound O1CCOC(C=C2I)=C1C=C2SC(N1CCBr)=NC2=C1N=CN=C2N HQDYUQMYJMUVOC-UHFFFAOYSA-N 0.000 description 1
• WBJHBCYKTBUULP-UHFFFAOYSA-N 9-(2-bromoethyl)-8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)sulfanyl]purin-6-amine Chemical compound N=1C=2C(N)=NC=NC=2N(CCBr)C=1SC(C(=C1)I)=CC2=C1CCC2 WBJHBCYKTBUULP-UHFFFAOYSA-N 0.000 description 1
• ZWTUZOCDDIACIA-UHFFFAOYSA-N 9-(3-aminopropyl)-2-fluoro-8-[[6-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-6-amine Chemical compound O1C(C)=CN=C1C(C(=C1)CC=2N(C3=NC(F)=NC(N)=C3N=2)CCCN)=CC2=C1OCCO2 ZWTUZOCDDIACIA-UHFFFAOYSA-N 0.000 description 1
• BACXBYWHORYCAF-UHFFFAOYSA-N 9-(3-aminopropyl)-8-[(5-iodo-1-benzofuran-6-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCCN)C(SC=3C(=CC=4C=COC=4C=3)I)=NC2=C1N BACXBYWHORYCAF-UHFFFAOYSA-N 0.000 description 1
• FGHXODPFIQASKW-UHFFFAOYSA-N 9-(3-aminopropyl)-8-[(6-iodo-1-benzofuran-5-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCCN)C(SC=3C(=CC=4OC=CC=4C=3)I)=NC2=C1N FGHXODPFIQASKW-UHFFFAOYSA-N 0.000 description 1
• ZSKLUCJWRDEVER-UHFFFAOYSA-N 9-(3-aminopropyl)-8-[(6-iodo-2,3-dihydro-1h-indol-5-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCCN)C(SC=3C(=CC=4NCCC=4C=3)I)=NC2=C1N ZSKLUCJWRDEVER-UHFFFAOYSA-N 0.000 description 1
• PGHGYYKIVAHEBB-UHFFFAOYSA-N 9-(3-aminopropyl)-8-[5-methoxy-2-(5-methylfuran-2-yl)phenyl]sulfanylpurin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCN)C=1SC1=CC(OC)=CC=C1C1=CC=C(C)O1 PGHGYYKIVAHEBB-UHFFFAOYSA-N 0.000 description 1
• QYJDQMHSZJKJSM-UHFFFAOYSA-N 9-(3-aminopropyl)-8-[[6-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1h-inden-5-yl]sulfanyl]purin-6-amine Chemical compound O1C(C)=CN=C1C(C(=C1)SC=2N(C3=NC=NC(N)=C3N=2)CCCN)=CC2=C1CCC2 QYJDQMHSZJKJSM-UHFFFAOYSA-N 0.000 description 1
• SUSAUXQZMLMQGA-UHFFFAOYSA-N 9-(3-aminopropyl)-8-[[7-(5-methylfuran-2-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]purin-6-amine Chemical compound O1C(C)=CC=C1C(C(=C1)SC=2N(C3=NC=NC(N)=C3N=2)CCCN)=CC2=C1OCCO2 SUSAUXQZMLMQGA-UHFFFAOYSA-N 0.000 description 1
• FTGHFXMKOIQFOU-UHFFFAOYSA-N 9-(3-bromopropyl)-2-fluoro-8-[(5-iodo-2,3-dihydro-1-benzofuran-6-yl)methyl]purin-6-amine Chemical compound N=1C=2C(N)=NC(F)=NC=2N(CCCBr)C=1CC(C(=C1)I)=CC2=C1CCO2 FTGHFXMKOIQFOU-UHFFFAOYSA-N 0.000 description 1
• QAVZGIJLJYXDOQ-UHFFFAOYSA-N 9-(3-bromopropyl)-8-(3-iodonaphthalen-2-yl)sulfanylpurin-6-amine Chemical compound C1=CC=C2C=C(I)C(SC=3N(CCCBr)C=4N=CN=C(C=4N=3)N)=CC2=C1 QAVZGIJLJYXDOQ-UHFFFAOYSA-N 0.000 description 1
• SYNIUTMQOGFIOZ-UHFFFAOYSA-N 9-(3-bromopropyl)-8-[(6-iodo-2,3-dihydro-1,4-benzodioxin-7-yl)sulfanyl]purin-6-amine Chemical compound O1CCOC(C=C2I)=C1C=C2SC(N1CCCBr)=NC2=C1N=CN=C2N SYNIUTMQOGFIOZ-UHFFFAOYSA-N 0.000 description 1
• RMIANEPUQOPXQF-UHFFFAOYSA-N 9-(3-bromopropyl)-8-[(6-iodo-2,3-dihydro-1-benzofuran-5-yl)sulfanyl]purin-6-amine Chemical compound N=1C=2C(N)=NC=NC=2N(CCCBr)C=1SC(C(=C1)I)=CC2=C1OCC2 RMIANEPUQOPXQF-UHFFFAOYSA-N 0.000 description 1
• OEOBTHBDOCZSQX-UHFFFAOYSA-N 9-(3-bromopropyl)-8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)sulfanyl]purin-6-amine Chemical compound N=1C=2C(N)=NC=NC=2N(CCCBr)C=1SC(C(=C1)I)=CC2=C1CCC2 OEOBTHBDOCZSQX-UHFFFAOYSA-N 0.000 description 1
• MTVGSEGTXGSRHT-UHFFFAOYSA-N 9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]-8-[3-(5-methyl-1,3-thiazol-2-yl)naphthalen-2-yl]sulfanylpurin-6-amine Chemical compound Cc1cnc(s1)-c1cc2ccccc2cc1Sc1nc2c(N)ncnc2n1CCC1CCCN(C1)S(C)(=O)=O MTVGSEGTXGSRHT-UHFFFAOYSA-N 0.000 description 1
• OIYMCHZGLOFSKR-UHFFFAOYSA-N 9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]-8-[[3-(5-methyl-1,3-thiazol-2-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]sulfanyl]purin-6-amine Chemical compound CS(=O)(=O)N1CC(CCC1)CCN1C2=NC=NC(=C2N=C1SC1=CC=2CCCCC=2C=C1C=1SC(=CN=1)C)N OIYMCHZGLOFSKR-UHFFFAOYSA-N 0.000 description 1
• XDZYMLXLMPMIDK-UHFFFAOYSA-N 9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]-8-[[5-(1H-pyrazol-5-yl)-2,3-dihydro-1H-indol-6-yl]sulfanyl]purin-6-amine Chemical compound CS(=O)(=O)N1CCCC(CCn2c(Sc3cc4NCCc4cc3-c3cc[nH]n3)nc3c(N)ncnc23)C1 XDZYMLXLMPMIDK-UHFFFAOYSA-N 0.000 description 1
• IEYDHPNTDZXKPC-UHFFFAOYSA-N 9-[2-(1-methylsulfonylpiperidin-3-yl)ethyl]-8-[[7-(propan-2-ylamino)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]purin-6-amine Chemical compound C(C)(C)NC=1C(=CC2=C(OCCO2)C=1)SC=1N(C2=NC=NC(=C2N=1)N)CCC1CN(CCC1)S(=O)(=O)C IEYDHPNTDZXKPC-UHFFFAOYSA-N 0.000 description 1
• DIBMXFJVQGNKAJ-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-2-fluoro-8-[(5-iodo-2,3-dihydro-1-benzofuran-6-yl)methyl]purin-6-amine Chemical compound N1=C(F)N=C2N(CCNCC(C)(C)C)C(CC=3C(=CC=4CCOC=4C=3)I)=NC2=C1N DIBMXFJVQGNKAJ-UHFFFAOYSA-N 0.000 description 1
• UMYVCGUOGVLPMM-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-2-fluoro-8-[[6-(furan-2-yl)-1h-indol-5-yl]methyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCNCC(C)(C)C)C=1CC1=CC=2C=CNC=2C=C1C1=CC=CO1 UMYVCGUOGVLPMM-UHFFFAOYSA-N 0.000 description 1
• IIBJEKOJGQUWKB-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[(3-iodo-5,6,7,8-tetrahydronaphthalen-2-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)(C)C)C(SC=3C(=CC=4CCCCC=4C=3)I)=NC2=C1N IIBJEKOJGQUWKB-UHFFFAOYSA-N 0.000 description 1
• YVMQDVQLTUCVFQ-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[(5-iodo-2,3-dihydro-1-benzofuran-6-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)(C)C)C(SC=3C(=CC=4CCOC=4C=3)I)=NC2=C1N YVMQDVQLTUCVFQ-UHFFFAOYSA-N 0.000 description 1
• UODSJUKFKYVCTI-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[(6-iodo-2,3-dihydro-1,4-benzodioxin-7-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)(C)C)C(SC=3C(=CC=4OCCOC=4C=3)I)=NC2=C1N UODSJUKFKYVCTI-UHFFFAOYSA-N 0.000 description 1
• HIHAAXIARJFGSG-UHFFFAOYSA-N 9-[2-(2,2-dimethylpropylamino)ethyl]-8-[(6-iodo-2,3-dihydro-1h-inden-5-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCNCC(C)(C)C)C(SC=3C(=CC=4CCCC=4C=3)I)=NC2=C1N HIHAAXIARJFGSG-UHFFFAOYSA-N 0.000 description 1
• YLAMCXRJROOFCK-UHFFFAOYSA-N 9-[2-(2-methylpropylamino)ethyl]-8-[(5-thiophen-2-yl-2,3-dihydro-1-benzofuran-6-yl)sulfanyl]purin-6-amine Chemical compound C(C(C)C)NCCN1C2=NC=NC(=C2N=C1SC1=CC2=C(CCO2)C=C1C=1SC=CC=1)N YLAMCXRJROOFCK-UHFFFAOYSA-N 0.000 description 1
• VKHZTFIFPAGOKL-UHFFFAOYSA-N 9-[2-(2-methylpropylamino)ethyl]-8-[(7-pyrrolidin-1-yl-2,3-dihydro-1,4-benzodioxin-6-yl)sulfanyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCNCC(C)C)C=1SC1=CC=2OCCOC=2C=C1N1CCCC1 VKHZTFIFPAGOKL-UHFFFAOYSA-N 0.000 description 1
• MZKZZZFJSYPWTP-UHFFFAOYSA-N 9-[2-(2-methylpropylamino)ethyl]-8-[[5-(1h-pyrazol-5-yl)-2,3-dihydro-1-benzofuran-6-yl]sulfanyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCNCC(C)C)C=1SC1=CC=2OCCC=2C=C1C1=CC=NN1 MZKZZZFJSYPWTP-UHFFFAOYSA-N 0.000 description 1
• FBDWMAIBQGTLJK-UHFFFAOYSA-N 9-[2-(2-methylpropylamino)ethyl]-8-[[5-(1h-pyrazol-5-yl)-2,3-dihydro-1-benzothiophen-6-yl]sulfanyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCNCC(C)C)C=1SC1=CC=2SCCC=2C=C1C1=CC=NN1 FBDWMAIBQGTLJK-UHFFFAOYSA-N 0.000 description 1
• YQORFHKVEAVTDF-UHFFFAOYSA-N 9-[3-(propan-2-ylamino)propyl]-8-[3-(1H-pyrazol-5-yl)naphthalen-2-yl]sulfanylpurin-6-amine Chemical compound CC(C)NCCCn1c(Sc2cc3ccccc3cc2-c2cc[nH]n2)nc2c(N)ncnc12 YQORFHKVEAVTDF-UHFFFAOYSA-N 0.000 description 1
• ULLRAZAROTVMGA-UHFFFAOYSA-N 9-[3-(propan-2-ylamino)propyl]-8-[[5-(1h-pyrazol-5-yl)-1h-indol-6-yl]sulfanyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)C)C=1SC1=CC=2NC=CC=2C=C1C1=CC=NN1 ULLRAZAROTVMGA-UHFFFAOYSA-N 0.000 description 1
• DCRJMRMEJAAGQM-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-2-fluoro-8-[[6-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-6-amine Chemical compound N=1C2=C(N)N=C(F)N=C2N(CCCNC(C)(C)C)C=1CC1=CC=2OCCOC=2C=C1C1=NC=CO1 DCRJMRMEJAAGQM-UHFFFAOYSA-N 0.000 description 1
• BABUTETYSPYIFM-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-2-fluoro-8-[[6-(4-methyl-1,3-thiazol-2-yl)-2,3-dihydro-1h-inden-5-yl]methyl]purin-6-amine Chemical compound CC1=CSC(C=2C(=CC=3CCCC=3C=2)CC=2N(C3=NC(F)=NC(N)=C3N=2)CCCNC(C)(C)C)=N1 BABUTETYSPYIFM-UHFFFAOYSA-N 0.000 description 1
• QDLDYNRHGYEMER-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-2-fluoro-8-[[6-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzodioxin-7-yl]methyl]purin-6-amine Chemical compound O1C(C)=CN=C1C(C(=C1)CC=2N(C3=NC(F)=NC(N)=C3N=2)CCCNC(C)(C)C)=CC2=C1OCCO2 QDLDYNRHGYEMER-UHFFFAOYSA-N 0.000 description 1
• GUACVABMNQGULP-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[(5-ethynyl-2,3-dihydro-1-benzofuran-6-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)(C)C)C(SC=3C(=CC=4CCOC=4C=3)C#C)=NC2=C1N GUACVABMNQGULP-UHFFFAOYSA-N 0.000 description 1
• CEDJPNVSLCCROV-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[(6-ethynyl-1-benzofuran-5-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)(C)C)C(SC=3C(=CC=4OC=CC=4C=3)C#C)=NC2=C1N CEDJPNVSLCCROV-UHFFFAOYSA-N 0.000 description 1
• BJLHSPSEFPRGOB-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[(6-ethynyl-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]-2-fluoropurin-6-amine Chemical compound N1=C(F)N=C2N(CCCNC(C)(C)C)C(CC=3C(=CC=4OCCOC=4C=3)C#C)=NC2=C1N BJLHSPSEFPRGOB-UHFFFAOYSA-N 0.000 description 1
• HTKMVETXQLTXOD-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[(6-ethynyl-4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)(C)C)C(SC=3C=C4OCCN(C4=CC=3C#C)C)=NC2=C1N HTKMVETXQLTXOD-UHFFFAOYSA-N 0.000 description 1
• WCEKUKMBCPOEPZ-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[(6-iodo-3,4-dihydro-2h-chromen-7-yl)sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)(C)C)C(SC=3C(=CC=4CCCOC=4C=3)I)=NC2=C1N WCEKUKMBCPOEPZ-UHFFFAOYSA-N 0.000 description 1
• YEXOWVMUERSDKU-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[(7-cyclopropyl-2,3-dihydro-1,4-benzodioxin-6-yl)sulfanyl]purin-6-amine Chemical compound CC(C)(C)NCCCn1c(Sc2cc3OCCOc3cc2C2CC2)nc2c(N)ncnc12 YEXOWVMUERSDKU-UHFFFAOYSA-N 0.000 description 1
• NXUMAGWWQLDDAR-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[5-(1,3-oxazol-2-yl)-2,3-dihydro-1-benzofuran-6-yl]sulfanyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)(C)C)C=1SC1=CC=2OCCC=2C=C1C1=NC=CO1 NXUMAGWWQLDDAR-UHFFFAOYSA-N 0.000 description 1
• JCTBHJDXYVQMND-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[5-(1,3-thiazol-2-yl)-2,3-dihydro-1-benzofuran-6-yl]sulfanyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)(C)C)C=1SC1=CC=2OCCC=2C=C1C1=NC=CS1 JCTBHJDXYVQMND-UHFFFAOYSA-N 0.000 description 1
• UIQJHLGIRXLKIY-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[5-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1-benzofuran-6-yl]sulfanyl]purin-6-amine Chemical compound O1C(C)=CN=C1C(C(=C1)SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)(C)C)=CC2=C1OCC2 UIQJHLGIRXLKIY-UHFFFAOYSA-N 0.000 description 1
• UTQZMRYLJVEVHM-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[5-(5-methyl-1,3-thiazol-2-yl)-2,3-dihydro-1-benzofuran-6-yl]sulfanyl]purin-6-amine Chemical compound S1C(C)=CN=C1C(C(=C1)SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)(C)C)=CC2=C1OCC2 UTQZMRYLJVEVHM-UHFFFAOYSA-N 0.000 description 1
• GXNBUVINYQGGHB-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[5-(dimethylamino)-1-benzofuran-6-yl]sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)(C)C)C(SC3=CC=4OC=CC=4C=C3N(C)C)=NC2=C1N GXNBUVINYQGGHB-UHFFFAOYSA-N 0.000 description 1
• WYVFSHHPVMHLRC-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[6-(1,3-thiazol-2-yl)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]purin-6-amine Chemical compound N=1C2=C(N)N=CN=C2N(CCCNC(C)(C)C)C=1SC1=CC=2CCOC=2C=C1C1=NC=CS1 WYVFSHHPVMHLRC-UHFFFAOYSA-N 0.000 description 1
• JUDWGZHYSWBFCR-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[6-(4-methyl-1,3-thiazol-2-yl)-2,3-dihydro-1h-inden-5-yl]sulfanyl]purin-6-amine Chemical compound CC1=CSC(C=2C(=CC=3CCCC=3C=2)SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)(C)C)=N1 JUDWGZHYSWBFCR-UHFFFAOYSA-N 0.000 description 1
• WNOCIAXTBJNJJP-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[6-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]purin-6-amine Chemical compound O1C(C)=CN=C1C(C(=C1)SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)(C)C)=CC2=C1CCO2 WNOCIAXTBJNJJP-UHFFFAOYSA-N 0.000 description 1
• ADNHXKAJNVTEMB-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[6-(5-methyl-1,3-oxazol-2-yl)-2,3-dihydro-1h-inden-5-yl]sulfanyl]purin-6-amine Chemical compound O1C(C)=CN=C1C(C(=C1)SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)(C)C)=CC2=C1CCC2 ADNHXKAJNVTEMB-UHFFFAOYSA-N 0.000 description 1
• PHRAWFATGOOKBQ-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[6-(5-methyl-1,3-thiazol-2-yl)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]purin-6-amine Chemical compound S1C(C)=CN=C1C(C(=C1)SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)(C)C)=CC2=C1CCO2 PHRAWFATGOOKBQ-UHFFFAOYSA-N 0.000 description 1
• OFKSCCKHJQADFE-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[6-(5-methylfuran-2-yl)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]purin-6-amine Chemical compound C(C)(C)(C)NCCCN1C2=NC=NC(=C2N=C1SC=1C(=CC2=C(CCO2)C=1)C=1OC(=CC=1)C)N OFKSCCKHJQADFE-UHFFFAOYSA-N 0.000 description 1
• WXUJAHPGDHQPFL-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[6-(dimethylamino)-1-benzofuran-5-yl]sulfanyl]purin-6-amine Chemical compound C(C)(C)(C)NCCCN1C2=NC=NC(=C2N=C1SC=1C(=CC2=C(C=CO2)C1)N(C)C)N WXUJAHPGDHQPFL-UHFFFAOYSA-N 0.000 description 1
• CHFJGWUKTLJFQG-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[6-(dimethylamino)-2,3-dihydro-1-benzofuran-5-yl]sulfanyl]purin-6-amine Chemical compound N1=CN=C2N(CCCNC(C)(C)C)C(SC3=CC=4CCOC=4C=C3N(C)C)=NC2=C1N CHFJGWUKTLJFQG-UHFFFAOYSA-N 0.000 description 1
• IRJKCOGYDDNCRW-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[7-(5-methylfuran-2-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]purin-6-amine Chemical compound O1C(C)=CC=C1C(C(=C1)SC=2N(C3=NC=NC(N)=C3N=2)CCCNC(C)(C)C)=CC2=C1OCCO2 IRJKCOGYDDNCRW-UHFFFAOYSA-N 0.000 description 1
• FKILFXAEKYYQAX-UHFFFAOYSA-N 9-[3-(tert-butylamino)propyl]-8-[[7-(dimethylamino)-2,3-dihydro-1,4-benzodioxin-6-yl]sulfanyl]purin-6-amine Chemical compound CN(C)c1cc2OCCOc2cc1Sc1nc2c(N)ncnc2n1CCCNC(C)(C)C FKILFXAEKYYQAX-UHFFFAOYSA-N 0.000 description 1
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
• 208000003174 Brain Neoplasms Diseases 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
• HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
• 206010015548 Euthanasia Diseases 0.000 description 1
• HNYVDIURSBJSAG-UHFFFAOYSA-N FC1=NC(=C2N=CN(C2=N1)CCNCC(C)(C)C)N Chemical compound FC1=NC(=C2N=CN(C2=N1)CCNCC(C)(C)C)N HNYVDIURSBJSAG-UHFFFAOYSA-N 0.000 description 1
• 101000711796 Homo sapiens Sclerostin Proteins 0.000 description 1
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
• 229910013470 LiC1 Inorganic materials 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
• 208000009905 Neurofibromatoses Diseases 0.000 description 1
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
• 229930040373 Paraformaldehyde Natural products 0.000 description 1
• 102100034201 Sclerostin Human genes 0.000 description 1
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
• 102100036980 Talin-2 Human genes 0.000 description 1
• 101710142305 Talin-2 Proteins 0.000 description 1
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
• AHWZCYVXODSVGD-UHFFFAOYSA-N [2,3-bis(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C(F)(F)F)=C1C(F)(F)F AHWZCYVXODSVGD-UHFFFAOYSA-N 0.000 description 1
• BPTABBGLHGBJQR-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BPTABBGLHGBJQR-UHFFFAOYSA-N 0.000 description 1
• RIIPFHVHLXPMHQ-UHFFFAOYSA-N [4-(dimethylamino)phenyl]boronic acid Chemical compound CN(C)C1=CC=C(B(O)O)C=C1 RIIPFHVHLXPMHQ-UHFFFAOYSA-N 0.000 description 1
• XAXXTYXMWOFKLW-UHFFFAOYSA-N [C-]1=CC=[NH+]1 Chemical compound [C-]1=CC=[NH+]1 XAXXTYXMWOFKLW-UHFFFAOYSA-N 0.000 description 1
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
• RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical class C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 150000001336 alkenes Chemical class 0.000 description 1
• 125000006323 alkenyl amino group Chemical group 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
• LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
• 229960003022 amoxicillin Drugs 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
• 229940098164 augmentin Drugs 0.000 description 1
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
• 210000001218 blood-brain barrier Anatomy 0.000 description 1
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 150000001649 bromium compounds Chemical class 0.000 description 1
• BQXQGZPYHWWCEB-UHFFFAOYSA-N carazolol Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2OCC(O)CNC(C)C BQXQGZPYHWWCEB-UHFFFAOYSA-N 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 239000013256 coordination polymer Substances 0.000 description 1
• 238000006880 cross-coupling reaction Methods 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• 239000003651 drinking water Substances 0.000 description 1
• 235000020188 drinking water Nutrition 0.000 description 1
• 238000000132 electrospray ionisation Methods 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• NSQBADKMIYCCSC-UHFFFAOYSA-N ethyl 2-(3-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(O)=C1 NSQBADKMIYCCSC-UHFFFAOYSA-N 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 150000003949 imides Chemical class 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 230000010354 integration Effects 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• 150000002545 isoxazoles Chemical class 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 231100000682 maximum tolerated dose Toxicity 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 201000004931 neurofibromatosis Diseases 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• 125000004433 nitrogen atom Chemical group N* 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 239000003921 oil Substances 0.000 description 1
• QDTOWROMMFMKDC-UHFFFAOYSA-N oxadiazole-5-carbonitrile Chemical compound N#CC1=CN=NO1 QDTOWROMMFMKDC-UHFFFAOYSA-N 0.000 description 1
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
• LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
• 229920002866 paraformaldehyde Polymers 0.000 description 1
• ICFQGMYPBURXAZ-UHFFFAOYSA-N pentane-1-sulfonamide Chemical compound CCCCCS(N)(=O)=O ICFQGMYPBURXAZ-UHFFFAOYSA-N 0.000 description 1
• 125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
• 229920000137 polyphosphoric acid Polymers 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
• QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 238000010791 quenching Methods 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• 238000004007 reversed phase HPLC Methods 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
• 235000019345 sodium thiosulphate Nutrition 0.000 description 1
• WOGMLDNCNBLDCA-JSYANWSFSA-M sodium;(2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [Na+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 WOGMLDNCNBLDCA-JSYANWSFSA-M 0.000 description 1
• SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
• IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
• HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• DCVICHWBECIALB-UHFFFAOYSA-N tert-butyl 2,3-dihydropyrrole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC=C1 DCVICHWBECIALB-UHFFFAOYSA-N 0.000 description 1
• AZFIXUGFEFRFQJ-UHFFFAOYSA-N tert-butyl n-naphthalen-2-ylcarbamate Chemical compound C1=CC=CC2=CC(NC(=O)OC(C)(C)C)=CC=C21 AZFIXUGFEFRFQJ-UHFFFAOYSA-N 0.000 description 1
• YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
• JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
• 125000004001 thioalkyl group Chemical group 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1