EA001714B1 - Производные 2-(пурин-9-ил)-тетрагидрофуран-3,4-диола - Google Patents

Info

Publication number

EA001714B1

EA001714B1 EA199900494A EA199900494A EA001714B1 EA 001714 B1 EA001714 B1 EA 001714B1 EA 199900494 A EA199900494 A EA 199900494A EA 199900494 A EA199900494 A EA 199900494A EA 001714 B1 EA001714 B1 EA 001714B1

Authority

EA

Eurasian Patent Office

Prior art keywords

diol

purin

tetrazol

ethylamino

tetrahydrofuran

Prior art date

1996-12-24

Links

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• YQUJSBYIKMQCIT-UHFFFAOYSA-N 2-purin-9-yloxolane-3,4-diol Chemical class OC1C(O)COC1N1C2=NC=NC=C2N=C1 YQUJSBYIKMQCIT-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 377
• -1 N-methylpiperazinyl Chemical group 0.000 claims abstract description 209
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 70
• 125000003118 aryl group Chemical group 0.000 claims abstract description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
• 239000001257 hydrogen Substances 0.000 claims abstract description 32
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 28
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
• 150000002367 halogens Chemical class 0.000 claims abstract description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 16
• 239000012453 solvate Substances 0.000 claims abstract description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
• 125000002785 azepinyl group Chemical group 0.000 claims abstract description 8
• 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 8
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 8
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 6
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
• SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims abstract description 4
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims abstract description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 119
• 239000000203 mixture Substances 0.000 claims description 112
• 238000000034 method Methods 0.000 claims description 83
• 125000000217 alkyl group Chemical group 0.000 claims description 55
• SSYDTHANSGMJTP-UHFFFAOYSA-N oxolane-3,4-diol Chemical compound OC1COCC1O SSYDTHANSGMJTP-UHFFFAOYSA-N 0.000 claims description 34
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 24
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 19
• 239000011737 fluorine Substances 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 125000004911 3,3-dimethylbutylamino group Chemical group CC(CCN*)(C)C 0.000 claims description 9
• 239000000460 chlorine Substances 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 101150065749 Churc1 gene Proteins 0.000 claims description 8
• 102100038239 Protein Churchill Human genes 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 7
• 208000027866 inflammatory disease Diseases 0.000 claims description 7
• 125000004899 1-ethylpropylamino group Chemical group C(C)C(CC)N* 0.000 claims description 6
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 230000002829 reductive effect Effects 0.000 claims description 4
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
• 239000000969 carrier Substances 0.000 claims description 2
• 230000001684 chronic effect Effects 0.000 claims description 2
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims description 2
• LCFFJOYIXJKWRM-UHFFFAOYSA-N 2-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC(C2C(C(O)CO2)O)=N1 LCFFJOYIXJKWRM-UHFFFAOYSA-N 0.000 claims 6
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 4
• 230000003993 interaction Effects 0.000 claims 2
• HIUJHNNCBNJKGX-UHFFFAOYSA-N 2-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1N=NC(C2C(C(O)CO2)O)=N1 HIUJHNNCBNJKGX-UHFFFAOYSA-N 0.000 claims 1
• BKJJATGKMNJRBW-UHFFFAOYSA-N 2-(2-propan-2-yltetrazol-5-yl)oxolane-3,4-diol Chemical compound CC(C)N1N=NC(C2C(C(O)CO2)O)=N1 BKJJATGKMNJRBW-UHFFFAOYSA-N 0.000 claims 1
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
• 230000000414 obstructive effect Effects 0.000 claims 1
• 201000004193 respiratory failure Diseases 0.000 claims 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract description 3
• 229910052760 oxygen Inorganic materials 0.000 abstract description 2
• USVQYAKJZJPSRK-GRXQJBFDSA-N (2r,3r,4s,5r)-2-[2-[2-(1-methylimidazol-4-yl)ethylamino]-6-(pentan-3-ylamino)purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C3=NN(C)N=N3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CN(C)C=N1 USVQYAKJZJPSRK-GRXQJBFDSA-N 0.000 abstract 2
• ZTPZBTREIAVWRZ-CMCWBKRRSA-N (2r,3r,4s,5r)-2-[2-[2-(1-methylimidazol-4-yl)ethylamino]-6-(2-phenylethylamino)purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1C=NC(CCNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@H](O4)C4=NN(C)N=N4)O)C=NC3=C(NCCC=3C=CC=CC=3)N=2)=C1 ZTPZBTREIAVWRZ-CMCWBKRRSA-N 0.000 abstract 1
• HOXQRVLGKMUTKR-CKXMCULTSA-N (2r,3r,4s,5r)-2-[2-[2-(6-aminopyridin-2-yl)ethylamino]-6-(2,2-diphenylethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=C(N)C=CC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 HOXQRVLGKMUTKR-CKXMCULTSA-N 0.000 abstract 1
• CCYUSUQOSHABQD-OVDFTCDZSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-morpholin-4-ylethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCOCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 CCYUSUQOSHABQD-OVDFTCDZSA-N 0.000 abstract 1
• RTXZDJRVDCPRJU-OVDFTCDZSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 RTXZDJRVDCPRJU-OVDFTCDZSA-N 0.000 abstract 1
• RLUQLDFOCWLMSH-OVDFTCDZSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-pyrrolidin-1-ylethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 RLUQLDFOCWLMSH-OVDFTCDZSA-N 0.000 abstract 1
• RFZYXTIQPZEWFB-YRIIQKNPSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1C=NC(CCNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@H](O4)C4=NN(C)N=N4)O)C=NC3=C(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)N=2)=C1 RFZYXTIQPZEWFB-YRIIQKNPSA-N 0.000 abstract 1
• RPTLPICWRONXMP-CMCWBKRRSA-N (2r,3r,4s,5r)-2-[6-(2-cyclohexylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1C=NC(CCNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@H](O4)C4=NN(C)N=N4)O)C=NC3=C(NCCC3CCCCC3)N=2)=C1 RPTLPICWRONXMP-CMCWBKRRSA-N 0.000 abstract 1
• CMJVPOARTDAFBV-RQXXJAGISA-N (2r,3r,4s,5r)-2-[6-(3,3-dimethylbutylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCCC(C)(C)C)=C3N=C2)O)=N1 CMJVPOARTDAFBV-RQXXJAGISA-N 0.000 abstract 1
• RRRUGHUZMCTUPJ-GRXQJBFDSA-N (2r,3r,4s,5r)-2-[6-(3,3-dimethylbutylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1C=NC(CCNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@H](O4)C4=NN(C)N=N4)O)C=NC3=C(NCCC(C)(C)C)N=2)=C1 RRRUGHUZMCTUPJ-GRXQJBFDSA-N 0.000 abstract 1
• SWJQFNZODOMOSK-CMCWBKRRSA-N (2r,3r,4s,5r)-2-[6-(benzylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCC=4C=CC=CC=4)=C3N=C2)O)=N1 SWJQFNZODOMOSK-CMCWBKRRSA-N 0.000 abstract 1
• UFGDNNTWISONPP-QPXQOZNCSA-N (2r,3r,4s,5r)-2-[6-(benzylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1C=NC(CCNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@H](O4)C4=NN(C)N=N4)O)C=NC3=C(NCC=3C=CC=CC=3)N=2)=C1 UFGDNNTWISONPP-QPXQOZNCSA-N 0.000 abstract 1
• RDPUMBLBDZVNOK-RQXXJAGISA-N (2r,3r,4s,5r)-2-[6-(cyclopentylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCCC4)=NC(NC4CCCC4)=C3N=C2)O)=N1 RDPUMBLBDZVNOK-RQXXJAGISA-N 0.000 abstract 1
• SZODFKMAMZSVDY-QPXQOZNCSA-N (2r,3r,4s,5r)-2-[6-(cyclopentylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-propan-2-yltetrazol-5-yl)oxolane-3,4-diol Chemical compound CC(C)N1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NC4CCCC4)=C3N=C2)O)=N1 SZODFKMAMZSVDY-QPXQOZNCSA-N 0.000 abstract 1
• YKTTVPKKAZXAJT-QPXQOZNCSA-N (2r,3r,4s,5r)-2-[6-[(3-iodophenyl)methylamino]-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1C=NC(CCNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@H](O4)C4=NN(C)N=N4)O)C=NC3=C(NCC=3C=C(I)C=CC=3)N=2)=C1 YKTTVPKKAZXAJT-QPXQOZNCSA-N 0.000 abstract 1
• WJKYPZJVAFYKCH-OVBHRPIXSA-N (2r,3r,4s,5r)-2-[6-amino-2-(3-bicyclo[2.2.1]heptanylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC4C5CCC(C5)C4)=NC(N)=C3N=C2)O)=N1 WJKYPZJVAFYKCH-OVBHRPIXSA-N 0.000 abstract 1
• IESAABKRXITHNB-WVBPYUMHSA-N (2r,3r,4s,5r)-2-[6-amino-2-(3-bicyclo[2.2.1]heptanylamino)purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC4C5CCC(C5)C4)=NC(N)=C3N=C2)O)=N1 IESAABKRXITHNB-WVBPYUMHSA-N 0.000 abstract 1
• ZVWLPTPKFNQGIR-PFHKOEEOSA-N (2r,3r,4s,5r)-2-[6-amino-2-(4-fluoroanilino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC=4C=CC(F)=CC=4)=NC(N)=C3N=C2)O)=N1 ZVWLPTPKFNQGIR-PFHKOEEOSA-N 0.000 abstract 1
• UTUSSRLIPLRJOY-MEQWQQMJSA-N (2r,3r,4s,5r)-2-[6-amino-2-(cyclopentylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC4CCCC4)=NC(N)=C3N=C2)O)=N1 UTUSSRLIPLRJOY-MEQWQQMJSA-N 0.000 abstract 1
• QXQLNOXHJDYQKA-QCUYGVNKSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(3,4-dihydroxyphenyl)ethylamino]purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4C=C(O)C(O)=CC=4)=NC(N)=C3N=C2)O)=N1 QXQLNOXHJDYQKA-QCUYGVNKSA-N 0.000 abstract 1
• JYSVYQLWXGLBHN-GRXQJBFDSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(3,4-dimethoxyphenyl)ethylamino]purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4C=C(OC)C(OC)=CC=4)=NC(N)=C3N=C2)O)=N1 JYSVYQLWXGLBHN-GRXQJBFDSA-N 0.000 abstract 1
• GQMRWKNFINBDRU-KSVNGYGVSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(3,4-dimethoxyphenyl)ethylamino]purin-9-yl]-5-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@H](O3)C3=NN(C)N=N3)O)C2=N1 GQMRWKNFINBDRU-KSVNGYGVSA-N 0.000 abstract 1
• VLFNMYSVSZTCML-RQXXJAGISA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(3,4-dimethoxyphenyl)ethylamino]purin-9-yl]-5-(2-propan-2-yltetrazol-5-yl)oxolane-3,4-diol Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@H](O3)C3=NN(N=N3)C(C)C)O)C2=N1 VLFNMYSVSZTCML-RQXXJAGISA-N 0.000 abstract 1
• GDXKXZAWXACNOQ-QCUYGVNKSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(4-aminophenyl)ethylamino]purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4C=CC(N)=CC=4)=NC(N)=C3N=C2)O)=N1 GDXKXZAWXACNOQ-QCUYGVNKSA-N 0.000 abstract 1
• WDCFPKWWXCKFES-QCUYGVNKSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(4-hydroxyphenyl)ethylamino]purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4C=CC(O)=CC=4)=NC(N)=C3N=C2)O)=N1 WDCFPKWWXCKFES-QCUYGVNKSA-N 0.000 abstract 1
• FNMQHSFUGUCVGC-KSVNGYGVSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(4-methoxyphenyl)ethylamino]purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4C=CC(OC)=CC=4)=NC(N)=C3N=C2)O)=N1 FNMQHSFUGUCVGC-KSVNGYGVSA-N 0.000 abstract 1
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