JP2006511490A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006511490A5 JP2006511490A5 JP2004546667A JP2004546667A JP2006511490A5 JP 2006511490 A5 JP2006511490 A5 JP 2006511490A5 JP 2004546667 A JP2004546667 A JP 2004546667A JP 2004546667 A JP2004546667 A JP 2004546667A JP 2006511490 A5 JP2006511490 A5 JP 2006511490A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- adenine
- phosphonylmethoxypropyl
- pyridyl
- phosphonylmethoxyethyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 25
- 229930024421 Adenine Natural products 0.000 claims 24
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 24
- 229960000643 adenine Drugs 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 18
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 17
- SUPKOOSCJHTBAH-UHFFFAOYSA-N adefovir Chemical compound NC1=NC=NC2=C1N=CN2CCOCP(O)(O)=O SUPKOOSCJHTBAH-UHFFFAOYSA-N 0.000 claims 15
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims 14
- 230000009385 viral infection Effects 0.000 claims 12
- 208000036142 Viral infection Diseases 0.000 claims 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 229940124597 therapeutic agent Drugs 0.000 claims 9
- 239000003443 antiviral agent Substances 0.000 claims 8
- -1 coviracyl Chemical compound 0.000 claims 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
- XHXFQGAZAVKMFF-UHFFFAOYSA-N 2-(2,6-diaminopurin-9-yl)ethoxymethylphosphonic acid Chemical compound NC1=NC(N)=C2N=CN(CCOCP(O)(O)=O)C2=N1 XHXFQGAZAVKMFF-UHFFFAOYSA-N 0.000 claims 7
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 7
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 7
- NZVORGQIEFTOQZ-UHFFFAOYSA-N 9-[2-(phosphonomethoxy)ethyl]guanine Chemical compound N1C(N)=NC(=O)C2=C1N(CCOCP(O)(O)=O)C=N2 NZVORGQIEFTOQZ-UHFFFAOYSA-N 0.000 claims 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 6
- 102000006992 Interferon-alpha Human genes 0.000 claims 5
- 108010047761 Interferon-alpha Proteins 0.000 claims 5
- 208000019423 liver disease Diseases 0.000 claims 5
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 229960001627 lamivudine Drugs 0.000 claims 4
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims 4
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims 4
- CKTSBUTUHBMZGZ-CHKWXVPMSA-N 4-amino-1-[(2s,4r,5s)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 CKTSBUTUHBMZGZ-CHKWXVPMSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 3
- RLAHNGKRJJEIJL-RFZPGFLSSA-N [(2r,4r)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methanol Chemical compound C12=NC(N)=NC(N)=C2N=CN1[C@H]1CO[C@@H](CO)O1 RLAHNGKRJJEIJL-RFZPGFLSSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 claims 3
- 229960005338 clevudine Drugs 0.000 claims 3
- 229960000980 entecavir Drugs 0.000 claims 3
- YXPVEXCTPGULBZ-WQYNNSOESA-N entecavir hydrate Chemical compound O.C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)C1=C YXPVEXCTPGULBZ-WQYNNSOESA-N 0.000 claims 3
- 208000002672 hepatitis B Diseases 0.000 claims 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims 3
- IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 claims 3
- GWFOVSGRNGAGDL-FSDSQADBSA-N 2-amino-9-[(1r,2r,3s)-2,3-bis(hydroxymethyl)cyclobutyl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1C[C@H](CO)[C@H]1CO GWFOVSGRNGAGDL-FSDSQADBSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 2
- 229960004316 cisplatin Drugs 0.000 claims 2
- 229960004679 doxorubicin Drugs 0.000 claims 2
- 229960005102 foscarnet Drugs 0.000 claims 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 2
- 229960004768 irinotecan Drugs 0.000 claims 2
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 229950005339 lobucavir Drugs 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 claims 1
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- 108010092160 Dactinomycin Proteins 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 claims 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
- 229930192392 Mitomycin Natural products 0.000 claims 1
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 229930012538 Paclitaxel Natural products 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 claims 1
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims 1
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 230000000840 anti-viral effect Effects 0.000 claims 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims 1
- 229960002092 busulfan Drugs 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229960004562 carboplatin Drugs 0.000 claims 1
- 229960004630 chlorambucil Drugs 0.000 claims 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims 1
- LRCTTYSATZVTRI-UHFFFAOYSA-L cyclohexane-1,2-diamine;platinum(4+);tetradecanoate Chemical compound [Pt+4].NC1CCCCC1N.CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O LRCTTYSATZVTRI-UHFFFAOYSA-L 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 229960000640 dactinomycin Drugs 0.000 claims 1
- 229960003668 docetaxel Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229960001904 epirubicin Drugs 0.000 claims 1
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 1
- 229960005420 etoposide Drugs 0.000 claims 1
- 229960002949 fluorouracil Drugs 0.000 claims 1
- 229960005277 gemcitabine Drugs 0.000 claims 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims 1
- 229960000908 idarubicin Drugs 0.000 claims 1
- 229960001101 ifosfamide Drugs 0.000 claims 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 229960001924 melphalan Drugs 0.000 claims 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 1
- 229960001428 mercaptopurine Drugs 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 229950004962 miriplatin Drugs 0.000 claims 1
- 229960004857 mitomycin Drugs 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 1
- 229960004964 temozolomide Drugs 0.000 claims 1
- 231100001274 therapeutic index Toxicity 0.000 claims 1
- 229960001196 thiotepa Drugs 0.000 claims 1
- 229960003087 tioguanine Drugs 0.000 claims 1
- MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims 1
- 229960000303 topotecan Drugs 0.000 claims 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 229960000653 valrubicin Drugs 0.000 claims 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38054502P | 2002-05-13 | 2002-05-13 | |
| PCT/US2003/014821 WO2004037161A2 (en) | 2002-05-13 | 2003-05-12 | Cyclic prodrugs of pmea one of its analogues |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006511490A JP2006511490A (ja) | 2006-04-06 |
| JP2006511490A5 true JP2006511490A5 (enExample) | 2006-06-29 |
| JP4476811B2 JP4476811B2 (ja) | 2010-06-09 |
Family
ID=32176361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004546667A Expired - Fee Related JP4476811B2 (ja) | 2002-05-13 | 2003-05-12 | Ｐｍｅａおよびそのアナログの新規ホスホン酸系プロドラッグ |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7214668B2 (enExample) |
| EP (2) | EP1532157A4 (enExample) |
| JP (1) | JP4476811B2 (enExample) |
| AU (1) | AU2003299492B2 (enExample) |
| CA (1) | CA2485702C (enExample) |
| IL (2) | IL164809A0 (enExample) |
| NZ (1) | NZ536328A (enExample) |
| TW (1) | TWI347325B (enExample) |
| WO (1) | WO2004037161A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6312662B1 (en) * | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| NZ536328A (en) | 2002-05-13 | 2007-11-30 | Metabasis Therapeutics Inc | Novel phosphonic acid based prodrugs of PMEA and its analogues |
| AU2003235501A1 (en) * | 2002-05-13 | 2003-11-11 | Metabasis Therapeutics, Inc. | PMEA and PMPA cyclic producing synthesis |
| EP1556398B1 (en) | 2002-10-31 | 2009-09-09 | Metabasis Therapeutics, Inc. | Novel cytarabine monophosphate prodrugs |
| US20050239753A1 (en) * | 2004-01-21 | 2005-10-27 | Gilead Sciences, Inc. | Methods of inhibition of MMTV-like viruses |
| US20050182252A1 (en) * | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| MXPA06014013A (es) | 2004-06-08 | 2007-03-15 | Metabasis Therapeutics Inc | Sintesis mediada por acidos de lewis de esteres ciclicos. |
| CA2586363A1 (en) * | 2004-11-15 | 2006-05-26 | Ceptyr, Inc. | Protein tyrosine phosphatase inhibitors and methods of use thereof |
| WO2007013085A1 (en) * | 2005-07-26 | 2007-02-01 | Hetero Drugs Limited | Novel process for acyclic phosphonate nucleotide analogs |
| US20070042501A1 (en) * | 2005-08-20 | 2007-02-22 | Institute Of Nuclear Energy Research | A novel technology for the purity assay of TRODAT-1 raw material |
| KR101424832B1 (ko) * | 2006-05-16 | 2014-08-06 | 길리애드 사이언시즈, 인코포레이티드 | 악성 혈액 종양 치료 방법 및 악성 혈액 종양 치료용 조성물 |
| CN101371841A (zh) * | 2007-08-23 | 2009-02-25 | 浙江医药股份有限公司新昌制药厂 | 结晶型恩替卡韦制剂及其制备方法和应用 |
| JP2009196959A (ja) * | 2008-02-25 | 2009-09-03 | Yamaguchi Univ | がん治療用医薬組成物 |
| CN101475594B (zh) * | 2009-02-06 | 2012-05-30 | 廖国超 | 肝靶向抗病毒前体药物环状磷酸酯及其应用 |
| CN101659676B (zh) * | 2009-09-07 | 2012-06-20 | 徐奎 | 一种硫代阿德福韦、替诺福韦肝靶向酯前体药物 |
| WO2011133963A2 (en) * | 2010-04-23 | 2011-10-27 | University Of Southern California | Tyrosine-based prodrugs of antiviral agents |
| US8884027B2 (en) | 2010-10-22 | 2014-11-11 | University Of Rochester | Melampomagnolide B derivatives as antileukemic and cytotoxic agents |
| CN103221037A (zh) * | 2010-11-12 | 2013-07-24 | 葛兰素惠尔康制造业私人有限公司 | 新药物组合物 |
| RU2606845C2 (ru) | 2010-12-10 | 2017-01-10 | СИГМАФАРМ ЛЭБОРЭТОРИЗ, ЭлЭлСи | Высокостабильные композиции перорально активных аналогов нуклеотидов или перорально активных пролекарств аналогов нуклеотидов |
| WO2012154698A2 (en) | 2011-05-06 | 2012-11-15 | Mckenna Charles E | Method to improve antiviral activity of nucleotide analogue drugs |
| EP2794624B1 (en) | 2011-12-22 | 2019-05-15 | Geron Corporation | Guanine analogs as telomerase substrates and telomere length affectors |
| 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 |
| CN103333209B (zh) * | 2013-07-05 | 2015-09-30 | 西安新通药物研究有限公司 | 替诺福韦前药(hts)新晶体 |
| CN104710477A (zh) * | 2013-12-16 | 2015-06-17 | 安徽贝克联合制药有限公司 | 替诺福韦环膦酸酯化合物及其药学上可接受的盐和其制备方法及应用 |
| US10449210B2 (en) | 2014-02-13 | 2019-10-22 | Ligand Pharmaceuticals Inc. | Prodrug compounds and their uses |
| DK3116511T3 (da) | 2014-03-14 | 2020-11-23 | Alltech Inc | Sammensætninger af selenoorganiske forbindelser og fremgangsmåder til anvendelse deraf |
| CN106687118A (zh) | 2014-07-02 | 2017-05-17 | 配体药物公司 | 前药化合物及其用途 |
| WO2017048252A1 (en) | 2015-09-15 | 2017-03-23 | Alltech, Inc. | Compositions of selenoorganic compounds and methods of use thereof |
| CN107540710B (zh) * | 2016-06-24 | 2020-10-16 | 浙江柏拉阿图医药科技有限公司 | 肝递送抗病毒前体药物核苷环磷酸酯化合物及应用 |
| WO2017220028A1 (zh) | 2016-06-24 | 2017-12-28 | 浙江柏拉阿图医药科技有限公司 | 肝递送抗病毒前体药物核苷环磷酸酯化合物及应用 |
| CN111788196A (zh) | 2018-01-09 | 2020-10-16 | 配体药物公司 | 缩醛化合物及其治疗用途 |
| CN108863797B (zh) * | 2018-07-02 | 2021-01-15 | 吉首大学 | 一类3-(取代/非取代苯基)-3-羟基丙酰氧肟酸的制备方法 |
| CN116178440B (zh) * | 2022-12-23 | 2025-12-30 | 杏林中医药科技(广州)有限公司 | 一种肝脏靶向烷化剂及其应用 |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR75178E (enExample) * | 1956-12-20 | 1961-09-08 | ||
| CS233665B1 (en) * | 1983-01-06 | 1985-03-14 | Antonin Holy | Processing of isomere o-phosphonylmethylderivative of anantiomere racemic vicinal diene |
| US4579849A (en) | 1984-04-06 | 1986-04-01 | Merck & Co., Inc. | N-alkylguanine acyclonucleosides as antiviral agents |
| FR2562543B1 (fr) * | 1984-04-10 | 1987-09-25 | Elf Aquitaine | Nouveaux phosphonites cycliques, leur preparation et applications |
| NL8403224A (nl) | 1984-10-24 | 1986-05-16 | Oce Andeno Bv | Dioxafosforinanen, de bereiding ervan en de toepassing voor het splitsen van optisch actieve verbindingen. |
| CS263951B1 (en) | 1985-04-25 | 1989-05-12 | Antonin Holy | 9-(phosponylmethoxyalkyl)adenines and method of their preparation |
| CS263952B1 (en) * | 1985-04-25 | 1989-05-12 | Holy Antonin | Remedy with antiviral effect |
| CS264222B1 (en) | 1986-07-18 | 1989-06-13 | Holy Antonin | N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them |
| EP0338372A3 (en) | 1988-04-22 | 1991-10-09 | American Cyanamid Company | Solubilized pro-drugs |
| ATE128623T1 (de) | 1988-08-02 | 1995-10-15 | Nissan Chemical Ind Ltd | Mittel zur verbesserung von arzneimitteleffekten für antitumormittel. |
| US5658889A (en) * | 1989-01-24 | 1997-08-19 | Gensia Pharmaceuticals, Inc. | Method and compounds for aica riboside delivery and for lowering blood glucose |
| CS276072B6 (en) * | 1990-08-06 | 1992-03-18 | Ustav Organicke Chemie A Bioch | (2R)-2-/DI(2-PROPYL)PHOSPHONYLMETHOXY/-3-p-TOLUENESULFONYLOXY -1- TRIMETHYLACETOXYPROPANE AND PROCESS FOR PREPARING THEREOF |
| EP0481214B1 (en) | 1990-09-14 | 1998-06-24 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Prodrugs of phosphonates |
| US5157027A (en) * | 1991-05-13 | 1992-10-20 | E. R. Squibb & Sons, Inc. | Bisphosphonate squalene synthetase inhibitors and method |
| GB9205917D0 (en) | 1992-03-18 | 1992-04-29 | Smithkline Beecham Plc | Pharmaceuticals |
| US5514798A (en) * | 1993-06-02 | 1996-05-07 | Gilead Sciences, Inc. | Method and cyclic carbonates for nucleotide analogues |
| ATE199906T1 (de) * | 1993-06-29 | 2001-04-15 | Mitsubishi Chem Corp | Phosphonat-nukleotid ester-derivate |
| EP0719273B1 (en) | 1993-09-17 | 2010-11-03 | Gilead Sciences, Inc. | Nucleotide analogs |
| US5567592A (en) | 1994-02-02 | 1996-10-22 | Regents Of The University Of California | Screening method for the identification of bioenhancers through the inhibition of P-glycoprotein transport in the gut of a mammal |
| ATE199721T1 (de) | 1994-07-04 | 2001-03-15 | Takeda Chemical Industries Ltd | Phosphonsäure verbindungen imre herstellung und verwendung |
| DE4445829A1 (de) | 1994-12-22 | 1996-06-27 | Leybold Ag | Gegenstrom-Schnüffellecksucher |
| US5665386A (en) | 1995-06-07 | 1997-09-09 | Avmax, Inc. | Use of essential oils to increase bioavailability of oral pharmaceutical compounds |
| US5716928A (en) | 1995-06-07 | 1998-02-10 | Avmax, Inc. | Use of essential oils to increase bioavailability of oral pharmaceutical compounds |
| CA2226414A1 (en) | 1995-07-17 | 1997-02-06 | Cephalon, Inc. | Phosphorous-containing cysteine and serine protease inhibitors |
| US5962440A (en) * | 1996-05-09 | 1999-10-05 | Bristol-Myers Squibb Company | Cyclic phosphonate ester inhibitors of microsomal triglyceride transfer protein and method |
| ZA981936B (en) * | 1997-03-07 | 1999-09-06 | Metabasis Therapeutics Inc | Novel benzimidazole inhibitors of fructose 1,6-bisphosphatase. |
| WO1998039344A1 (en) | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel purine inhibitors of fructose-1,6-bisphosphatase |
| WO1998039342A1 (en) * | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel indole and azaindole inhibitors of fructose-1,6-bisphosphatase |
| TR200200137T2 (tr) | 1997-07-25 | 2002-09-23 | Gilead Sciences, Inc. | Nükleotid analog kompozisyonlar. |
| US5962522A (en) * | 1997-09-05 | 1999-10-05 | Avmax, Inc. | Propyl gallate to increase bioavailability of orally administered pharmaceutical compounds |
| US6180666B1 (en) * | 1997-09-05 | 2001-01-30 | Anmax, Inc. | Use of gallic acid esters to increase bioavailability of orally administered pharmaceutical compounds |
| US6312662B1 (en) * | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| WO2000014095A1 (en) * | 1998-09-09 | 2000-03-16 | Metabasis Therapeutics, Inc. | Novel heteroaromatic inhibitors of fructose 1,6-bisphosphatase |
| RU2227749C2 (ru) | 1998-12-24 | 2004-04-27 | Метабэйсис Терапьютикс, Инк. | Комбинация ингибиторов fbpазы и сенсибилизаторов инсулина для лечения диабета |
| IL145052A0 (en) | 1999-03-05 | 2002-06-30 | Metabasis Therapeutics Inc | Novel phosphorus-containing prodrugs |
| EP1210354A1 (en) * | 1999-09-08 | 2002-06-05 | Metabasis Therapeutics, Inc. | Prodrugs for liver specific drug delivery |
| CN1291994C (zh) | 2000-07-21 | 2006-12-27 | 吉里德科学公司 | 核苷酸膦酸酯类似物前药及其筛选和制备方法 |
| AU2003235501A1 (en) * | 2002-05-13 | 2003-11-11 | Metabasis Therapeutics, Inc. | PMEA and PMPA cyclic producing synthesis |
| NZ536328A (en) | 2002-05-13 | 2007-11-30 | Metabasis Therapeutics Inc | Novel phosphonic acid based prodrugs of PMEA and its analogues |
| EP1556398B1 (en) * | 2002-10-31 | 2009-09-09 | Metabasis Therapeutics, Inc. | Novel cytarabine monophosphate prodrugs |
| HRP20100626T1 (hr) * | 2003-12-30 | 2011-03-31 | Gilead Sciences | Fosfonati, monofosfonamidati, bisfosfonamidati za liječenje virusnih bolesti |
| MXPA06014013A (es) * | 2004-06-08 | 2007-03-15 | Metabasis Therapeutics Inc | Sintesis mediada por acidos de lewis de esteres ciclicos. |
-
2003
- 2003-05-12 NZ NZ536328A patent/NZ536328A/en not_active IP Right Cessation
- 2003-05-12 US US10/436,922 patent/US7214668B2/en not_active Expired - Lifetime
- 2003-05-12 AU AU2003299492A patent/AU2003299492B2/en not_active Ceased
- 2003-05-12 IL IL16480903A patent/IL164809A0/xx unknown
- 2003-05-12 EP EP03799779A patent/EP1532157A4/en not_active Withdrawn
- 2003-05-12 EP EP10005037.6A patent/EP2223927B1/en not_active Expired - Lifetime
- 2003-05-12 JP JP2004546667A patent/JP4476811B2/ja not_active Expired - Fee Related
- 2003-05-12 CA CA2485702A patent/CA2485702C/en not_active Expired - Lifetime
- 2003-05-12 WO PCT/US2003/014821 patent/WO2004037161A2/en not_active Ceased
- 2003-11-18 TW TW092132408A patent/TWI347325B/zh not_active IP Right Cessation
-
2004
- 2004-10-25 IL IL164809A patent/IL164809A/en active IP Right Grant
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2485702A1 (en) | Novel phosphonic acid based prodrugs of pmea and its analogues | |
| JP5142716B2 (ja) | サイクリックエステルのルイス酸介在合成法 | |
| TWI494309B (zh) | Ｃ型肝炎病毒（ｈｃｖ）nｓ５ａ抑制劑 | |
| JP2024534526A (ja) | ピリジン系誘導体及びその使用 | |
| JP2006507254A5 (enExample) | ||
| JP2021523159A5 (enExample) | ||
| JP2005508967A5 (enExample) | ||
| AU2017302635A1 (en) | Chemokine receptor modulators and uses thereof | |
| JP2010522765A5 (enExample) | ||
| JP2006503838A5 (enExample) | ||
| RU2007146669A (ru) | Пролекарства антагонистов a2b рецептора аденозина | |
| CN111315744B (zh) | 杂芳基并四氢吡啶类化合物、其制备方法、药物组合物及应用 | |
| JP2009541225A5 (enExample) | ||
| JP2006507355A5 (enExample) | ||
| ES2785409T3 (es) | Formas sólidas de un compuesto antiviral | |
| JP7381602B2 (ja) | 二環式及び三環式化合物 | |
| AU2017389818B2 (en) | Quinazoline compound and preparation method, application, and pharmaceutical compostion thereof | |
| JP2020502116A5 (enExample) | ||
| JP2019535644A (ja) | ジヒドロピリミジン化合物並びにその調製方法及び使用 | |
| JP2019516688A (ja) | プロテインキナーゼ阻害剤としてのアデニン誘導体 | |
| JP2007532628A5 (enExample) | ||
| KR102750159B1 (ko) | Rip-1 키나아제 억제제인 바이사이클릭 화합물 및 이의 응용 | |
| RU2011108485A (ru) | Новые (поли)аминоалкиламиноалкиламидные, алкилмочевинные или алкилсульфонамидные производные эпиподофиллотоксина, способ их получения и их применение в терапии в качестве противораковых средств | |
| JP2014518870A5 (enExample) | ||
| CN108601785A (zh) | 嘧啶并哒嗪酮在治疗癌症中的用途 |