JP2004518675A5 - - Google Patents
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- JP2004518675A5 JP2004518675A5 JP2002557964A JP2002557964A JP2004518675A5 JP 2004518675 A5 JP2004518675 A5 JP 2004518675A5 JP 2002557964 A JP2002557964 A JP 2002557964A JP 2002557964 A JP2002557964 A JP 2002557964A JP 2004518675 A5 JP2004518675 A5 JP 2004518675A5
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- JP
- Japan
- Prior art keywords
- methyl
- compound
- amino
- oxy
- purin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 hydroxy, amino Chemical group 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 72
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims description 32
- MHNAKYHTAISYPF-UHFFFAOYSA-N [1-[(2-amino-6-chloropurin-9-yl)methyl]cyclopropyl]oxymethylphosphonic acid Chemical compound C12=NC(N)=NC(Cl)=C2N=CN1CC1(OCP(O)(O)=O)CC1 MHNAKYHTAISYPF-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 36
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 29
- 229950010765 pivalate Drugs 0.000 claims 19
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 6
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- KDNSSKPZBDNJDF-UHFFFAOYSA-N [1-[(2-aminopurin-9-yl)methyl]cyclopropyl]oxymethylphosphonic acid Chemical compound C12=NC(N)=NC=C2N=CN1CC1(OCP(O)(O)=O)CC1 KDNSSKPZBDNJDF-UHFFFAOYSA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 2
- NNQNNHMEFBBMJY-UHFFFAOYSA-N 2-[1-[(2-amino-6-oxo-3h-purin-9-yl)methyl]cyclopropyl]ethylphosphonic acid Chemical compound C12=NC(N)=NC(O)=C2N=CN1CC1(CCP(O)(O)=O)CC1 NNQNNHMEFBBMJY-UHFFFAOYSA-N 0.000 claims 2
- VUDVGFWLOQIDAI-UHFFFAOYSA-N 2-[1-[(2-amino-6-oxo-3h-purin-9-yl)methyl]cyclopropyl]propylphosphonic acid Chemical compound C1=NC2=C(O)N=C(N)N=C2N1CC1(C(CP(O)(O)=O)C)CC1 VUDVGFWLOQIDAI-UHFFFAOYSA-N 0.000 claims 2
- HJGDZNIKQVIHLM-UHFFFAOYSA-N 2-[1-[(2-aminopurin-9-yl)methyl]cyclopropyl]propylphosphonic acid Chemical compound C1=NC2=CN=C(N)N=C2N1CC1(C(CP(O)(O)=O)C)CC1 HJGDZNIKQVIHLM-UHFFFAOYSA-N 0.000 claims 2
- SOZWOLUYZONMNT-UHFFFAOYSA-N 2-[1-[(6-aminopurin-9-yl)methyl]cyclopropyl]ethylphosphonic acid Chemical compound C1=NC=2C(N)=NC=NC=2N1CC1(CCP(O)(O)=O)CC1 SOZWOLUYZONMNT-UHFFFAOYSA-N 0.000 claims 2
- ARKBKBKWZNRBNM-UHFFFAOYSA-N 2-[1-[[2-amino-6-(4-methylphenyl)sulfanylpurin-9-yl]methyl]cyclopropyl]ethylphosphonic acid Chemical compound C1=CC(C)=CC=C1SC1=NC(N)=NC2=C1N=CN2CC1(CCP(O)(O)=O)CC1 ARKBKBKWZNRBNM-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- DJYANLQPSGKNDM-UHFFFAOYSA-N C1CCC(C1)C(=O)OCOP(=O)(COC2(CC2)CN3C=NC4=C(N=CN=C43)N)OCC5(CCCC5)C(=O)O Chemical compound C1CCC(C1)C(=O)OCOP(=O)(COC2(CC2)CN3C=NC4=C(N=CN=C43)N)OCC5(CCCC5)C(=O)O DJYANLQPSGKNDM-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- YQQZFOTZFRQHRK-UHFFFAOYSA-N [[1-[(2-aminopurin-9-yl)methyl]cyclopropyl]oxymethyl-(piperidine-1-carbonyloxymethoxy)phosphoryl]oxymethyl piperidine-1-carboxylate Chemical compound C12=NC(N)=NC=C2N=CN1CC1(OCP(=O)(OCOC(=O)N2CCCCC2)OCOC(=O)N2CCCCC2)CC1 YQQZFOTZFRQHRK-UHFFFAOYSA-N 0.000 claims 2
- LBMGUBIXYLAHIP-UHFFFAOYSA-N [[1-[(2-aminopurin-9-yl)methyl]cyclopropyl]oxymethyl-(pyrrolidine-1-carbonyloxymethoxy)phosphoryl]oxymethyl pyrrolidine-1-carboxylate Chemical compound C12=NC(N)=NC=C2N=CN1CC1(OCP(=O)(OCOC(=O)N2CCCC2)OCOC(=O)N2CCCC2)CC1 LBMGUBIXYLAHIP-UHFFFAOYSA-N 0.000 claims 2
- MUNVPQSEWSFCNO-UHFFFAOYSA-N [[1-[(6-aminopurin-9-yl)methyl]cyclopropyl]oxymethyl-(3-methylbutanoyloxymethoxy)phosphoryl]oxymethyl 3-methylbutanoate Chemical compound C1=NC2=C(N)N=CN=C2N1CC1(OCP(=O)(OCOC(=O)CC(C)C)OCOC(=O)CC(C)C)CC1 MUNVPQSEWSFCNO-UHFFFAOYSA-N 0.000 claims 2
- PSNTZKJYCNHIOZ-UHFFFAOYSA-N [[1-[(6-aminopurin-9-yl)methyl]cyclopropyl]peroxy-methylphosphoryl]oxymethyl propan-2-yl carbonate Chemical compound CP(OCOC(=O)OC(C)C)(OOC1(CC1)CN1C2=NC=NC(=C2N=C1)N)=O PSNTZKJYCNHIOZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims 1
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 1
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims 1
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 claims 1
- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 claims 1
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims 1
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 claims 1
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 claims 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 claims 1
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 claims 1
- AZEVYGFOCGBUTB-UHFFFAOYSA-N 2-[1-[(2-aminopurin-9-yl)methyl]cyclopropyl]ethylphosphonic acid Chemical compound C12=NC(N)=NC=C2N=CN1CC1(CCP(O)(O)=O)CC1 AZEVYGFOCGBUTB-UHFFFAOYSA-N 0.000 claims 1
- QIFRUBOFZRICFI-UHFFFAOYSA-N 2-[1-[(6-aminopurin-9-yl)methyl]cyclopropyl]propylphosphonic acid Chemical compound C1=NC2=C(N)N=CN=C2N1CC1(C(CP(O)(O)=O)C)CC1 QIFRUBOFZRICFI-UHFFFAOYSA-N 0.000 claims 1
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims 1
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims 1
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 claims 1
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims 1
- MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 claims 1
- VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 claims 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 claims 1
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- 229940125846 compound 25 Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| KR20010003087 | 2001-01-19 | ||
| PCT/KR2002/000086 WO2002057288A1 (en) | 2001-01-19 | 2002-01-18 | Novel acyclic nucleoside phosphonate derivatives, salts thereof and process for the preparation of the same |
Publications (3)
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| JP2004518675A JP2004518675A (ja) | 2004-06-24 |
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| JP (1) | JP3959348B2 (https=) |
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| AR (1) | AR035933A1 (https=) |
| AT (1) | ATE478887T1 (https=) |
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| WO (1) | WO2002057288A1 (https=) |
| ZA (1) | ZA200304181B (https=) |
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| CA2440809A1 (en) * | 2001-03-01 | 2002-09-12 | Conforma Therapeutics Corp. | Methods for treating genetically-defined proliferative disorders with hsp90 inhibitors |
| WO2003037860A2 (en) | 2001-10-30 | 2003-05-08 | Conforma Therapeutics Corporation | Purine analogs having hsp90-inhibiting activity |
| RU2005108601A (ru) * | 2002-09-26 | 2006-01-20 | Эл Джи Лайф Сайенсиз Лтд. (Kr) | (+)-транс-изомеры(1-фосфонометокси-2-алкилциклопропил)метилнуклеозидные производные, способ получения их стереоизомеров и применение указанных соединений в качестве противовирусных средств |
| MXPA06002997A (es) * | 2003-09-18 | 2007-02-08 | Conforma Therapeutics Corp | Novedosos compuestos heterociclicos como inhibidores- hsp90. |
| KR20050062944A (ko) * | 2003-12-19 | 2005-06-28 | 주식회사 엘지생명과학 | 디이소프로필((1-((2-아미노-6-클로로-9ｈ-퓨린-9-일)메틸)사이클로프로필)옥시)-메틸포스포네이트의 새로운 제조방법 |
| KR20050062940A (ko) * | 2003-12-19 | 2005-06-28 | 주식회사 엘지생명과학 | 디이소프로필((1-((2-아미노-6-할로-9ｈ-퓨린-9-일)메틸)사이클로프로필)옥시)-메틸포스포네이트의 새로운 제조방법 |
| JP2007523180A (ja) * | 2004-02-17 | 2007-08-16 | エルジー・ライフ・サイエンシーズ・リミテッド | Ｈｉｖ感染治療に有用なヌクレオシドホスホネート誘導体 |
| KR101033290B1 (ko) * | 2004-07-02 | 2011-05-09 | 주식회사 엘지생명과학 | 다이아이소프로필((1-(하이드록시메틸)-사이클로프로필)옥시)메틸포스포네이트의 새로운 제조 방법 |
| ES2401285T3 (es) | 2004-12-16 | 2013-04-18 | The Regents Of The University Of California | Fármacos con el pulmón como diana |
| AU2006230447A1 (en) | 2005-03-30 | 2006-10-05 | Conforma Therapeutics Corporation | Alkynyl pyrrolopyrimidines and related analogs as HSP90-inhibitors |
| US8434912B2 (en) * | 2006-02-27 | 2013-05-07 | Illumination Management Solutions, Inc. | LED device for wide beam generation |
| JP2009528556A (ja) * | 2006-02-27 | 2009-08-06 | イルミネーション マネジメント ソリューションズ インコーポレイテッド | 幅広ビーム生成のための改良ｌｅｄデバイス |
| GB0623493D0 (en) * | 2006-11-24 | 2007-01-03 | Univ Cardiff | Chemical compounds |
| CL2008000070A1 (es) | 2007-01-17 | 2008-07-25 | Lg Life Sciences Ltd | Monosal del acido maleico (3-[({1-[(2-amino-9h-purin-9-il)metil]ciclopropil}oxi)metil]-8,8-dimetil-3,7-dioxo-2,4,6-trioxa-3 lambda 5-fosfanon-1-il-pivalato; composicion farmaceutica que comprende a dicha monosal; y uso para el tratamiento del virus h |
| CA2683316A1 (en) | 2007-04-13 | 2009-02-19 | Southern Research Institute | Anti-angiogenic agents and methods of use |
| AU2008254676B2 (en) * | 2007-05-21 | 2012-03-22 | Illumination Management Solutions, Inc. | An improved LED device for wide beam generation and method of making the same |
| EP2326870B1 (en) * | 2008-08-14 | 2017-01-25 | Cooper Technologies Company | Led devices for offset wide beam generation |
| US8256919B2 (en) * | 2008-12-03 | 2012-09-04 | Illumination Management Solutions, Inc. | LED replacement lamp and a method of replacing preexisting luminaires with LED lighting assemblies |
| CN102093422B (zh) * | 2009-12-10 | 2015-02-25 | 中国人民解放军军事医学科学院毒物药物研究所 | 无环核苷膦酸酯衍生物及其医药用途 |
| CN102286026B (zh) * | 2010-06-18 | 2014-07-02 | 中国人民解放军军事医学科学院毒物药物研究所 | 无环核苷酸类似物的盐及其晶型和药物组合物 |
| WO2012079035A1 (en) | 2010-12-10 | 2012-06-14 | Sigmapharm Laboratories, Llc | Highly stable compositions of orally active nucleotide analogues or orally active nucleotide analogue prodrugs |
| CN103665043B (zh) | 2012-08-30 | 2017-11-10 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药及其在医药上的应用 |
| SG10201800188SA (en) | 2013-03-15 | 2018-02-27 | Univ California | Acyclic nucleoside phosphonate diesters |
| CN104119385B (zh) * | 2014-07-24 | 2017-04-05 | 廖国超 | 核苷类似物的磷酸酯前药及其应用 |
| CN111808136B (zh) | 2014-09-15 | 2024-06-11 | 加利福尼亚大学董事会 | 核苷酸类似物 |
| CN106432330B (zh) * | 2015-08-11 | 2019-02-01 | 天津科伦药物研究有限公司 | Lb80380药物的中间体化合物及其制备方法和用途 |
| EP3350191B9 (en) | 2015-09-15 | 2021-12-22 | The Regents of the University of California | Nucleotide analogs |
| CN106977548A (zh) * | 2016-01-19 | 2017-07-25 | 四川海思科制药有限公司 | 倍司福韦复合物及其制备方法和用途 |
| CN107849074A (zh) * | 2016-01-19 | 2018-03-27 | 四川海思科制药有限公司 | 一种核苷类似物的烷氧烷基酯前药及其应用 |
| KR102623581B1 (ko) * | 2016-07-18 | 2024-01-11 | 일동제약(주) | 항바이러스성 약물의 오로트산염, 이의 제조 방법 및 상기 염을 포함하는 약제학적 조성물 |
| CN108276443A (zh) * | 2017-01-06 | 2018-07-13 | 米文君 | 一种新的化合物及其用途 |
| KR102096144B1 (ko) * | 2017-07-03 | 2020-04-01 | 주식회사 엘지화학 | 포스포네이트 뉴클레오사이드계 b형 간염 치료제 합성용 중간체 화합물의 연속식 제조방법 |
| CN108997429B (zh) * | 2018-07-27 | 2020-10-30 | 广州粤美医药科技有限公司 | 一种制备贝西福韦的方法 |
| CN113735863A (zh) * | 2021-09-29 | 2021-12-03 | 武汉九州钰民医药科技有限公司 | Wee1抑制剂adavosertib的制备工艺 |
| CN113880883A (zh) * | 2021-11-11 | 2022-01-04 | 奥锐特药业股份有限公司 | 核苷类磷酸酯前药的制备方法 |
| CN114560463B (zh) * | 2022-03-23 | 2023-10-20 | 福州大学 | 一种核壳结构的氮掺杂碳壳包裹碳化钼核微米球材料的制备方法 |
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| US5977061A (en) * | 1995-04-21 | 1999-11-02 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | N6 - substituted nucleotide analagues and their use |
| US5874577A (en) * | 1996-04-03 | 1999-02-23 | Medichem Research, Inc. | Method for the preparing 9-12-(Diethoxyphosphonomethoxy)ethyl!adenine and analogues thereof |
| US5877166A (en) * | 1996-04-29 | 1999-03-02 | Sri International | Enantiomerically pure 2-aminopurine phosphonate nucleotide analogs as antiviral agents |
| US5922695A (en) * | 1996-07-26 | 1999-07-13 | Gilead Sciences, Inc. | Antiviral phosphonomethyoxy nucleotide analogs having increased oral bioavarilability |
| US5935946A (en) * | 1997-07-25 | 1999-08-10 | Gilead Sciences, Inc. | Nucleotide analog composition and synthesis method |
| PT988304E (pt) | 1997-08-15 | 2001-10-31 | Medivir Ab | Analogos de nucleosidos tais como os antivirais que contem inibidores de transcritase reversa retroviral e de adn-polimerase do virus da hepatite b (hbv) |
| MY141789A (en) * | 2001-01-19 | 2010-06-30 | Lg Chem Investment Ltd | Novel acyclic nucleoside phosphonate derivatives, salts thereof and process for the preparation of the same. |
| CA2479037C (en) * | 2002-03-15 | 2010-11-09 | Jiri Zemlicka | 2-amino-9[(2-hydroxymethyl)cyclopropylidenemethyl]purines as antiviral agents |
| RU2005108601A (ru) * | 2002-09-26 | 2006-01-20 | Эл Джи Лайф Сайенсиз Лтд. (Kr) | (+)-транс-изомеры(1-фосфонометокси-2-алкилциклопропил)метилнуклеозидные производные, способ получения их стереоизомеров и применение указанных соединений в качестве противовирусных средств |
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- 2002-01-16 MY MYPI20020143A patent/MY141789A/en unknown
- 2002-01-18 PL PL373670A patent/PL212730B1/pl not_active IP Right Cessation
- 2002-01-18 EP EP02711484A patent/EP1358198B1/en not_active Expired - Lifetime
- 2002-01-18 DE DE60237429T patent/DE60237429D1/de not_active Expired - Lifetime
- 2002-01-18 RU RU2003125372/04A patent/RU2266294C2/ru not_active IP Right Cessation
- 2002-01-18 ES ES02711484T patent/ES2350197T3/es not_active Expired - Lifetime
- 2002-01-18 NZ NZ526632A patent/NZ526632A/en not_active IP Right Cessation
- 2002-01-18 MX MXPA03006001A patent/MXPA03006001A/es active IP Right Grant
- 2002-01-18 DK DK02711484.2T patent/DK1358198T3/da active
- 2002-01-18 WO PCT/KR2002/000086 patent/WO2002057288A1/en not_active Ceased
- 2002-01-18 BR BR0206165-1A patent/BR0206165A/pt not_active IP Right Cessation
- 2002-01-18 PT PT02711484T patent/PT1358198E/pt unknown
- 2002-01-18 CN CNB028037774A patent/CN100347185C/zh not_active Expired - Lifetime
- 2002-01-18 AT AT02711484T patent/ATE478887T1/de active
- 2002-01-18 CA CA002433591A patent/CA2433591C/en not_active Expired - Fee Related
- 2002-01-18 US US10/450,780 patent/US7157448B2/en not_active Expired - Fee Related
- 2002-01-18 AU AU2002230230A patent/AU2002230230B2/en not_active Ceased
- 2002-01-18 KR KR10-2002-0003051A patent/KR100441638B1/ko not_active Expired - Fee Related
- 2002-01-18 JP JP2002557964A patent/JP3959348B2/ja not_active Expired - Fee Related
- 2002-01-19 EG EG20020063A patent/EG24382A/xx active
- 2002-01-21 AR ARP020100197A patent/AR035933A1/es active IP Right Grant
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- 2009-09-09 US US12/585,229 patent/US7723319B2/en not_active Expired - Fee Related
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