ES2572631T3 - Métodos de tratamiento de infecciones virales - Google Patents
Métodos de tratamiento de infecciones virales Download PDFInfo
- Publication number
- ES2572631T3 ES2572631T3 ES09704809.4T ES09704809T ES2572631T3 ES 2572631 T3 ES2572631 T3 ES 2572631T3 ES 09704809 T ES09704809 T ES 09704809T ES 2572631 T3 ES2572631 T3 ES 2572631T3
- Authority
- ES
- Spain
- Prior art keywords
- virus
- observed
- hiv
- compound
- acid
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title abstract description 8
- 230000009385 viral infection Effects 0.000 title description 3
- 208000036142 Viral infection Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 150000003839 salts Chemical class 0.000 abstract description 12
- 230000000840 anti-viral effect Effects 0.000 abstract description 11
- 239000013543 active substance Substances 0.000 abstract description 10
- 208000015181 infectious disease Diseases 0.000 abstract description 10
- 229960002049 etravirine Drugs 0.000 abstract description 8
- PYGWGZALEOIKDF-UHFFFAOYSA-N etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 abstract description 8
- XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 abstract description 7
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 abstract description 7
- -1 efavirnez Chemical compound 0.000 abstract description 7
- 229960004710 maraviroc Drugs 0.000 abstract description 7
- GSNHKUDZZFZSJB-QYOOZWMWSA-N maraviroc Chemical compound CC(C)C1=NN=C(C)N1[C@@H]1C[C@H](N2CC[C@H](NC(=O)C3CCC(F)(F)CC3)C=3C=CC=CC=3)CC[C@H]2C1 GSNHKUDZZFZSJB-QYOOZWMWSA-N 0.000 abstract description 7
- 229960000311 ritonavir Drugs 0.000 abstract description 7
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 abstract description 7
- AXRYRYVKAWYZBR-UHFFFAOYSA-N Atazanavir Natural products C=1C=C(C=2N=CC=CC=2)C=CC=1CN(NC(=O)C(NC(=O)OC)C(C)(C)C)CC(O)C(NC(=O)C(NC(=O)OC)C(C)(C)C)CC1=CC=CC=C1 AXRYRYVKAWYZBR-UHFFFAOYSA-N 0.000 abstract description 6
- 108010019625 Atazanavir Sulfate Proteins 0.000 abstract description 6
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 abstract description 6
- 208000031886 HIV Infections Diseases 0.000 abstract description 6
- KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 abstract description 6
- SUJUHGSWHZTSEU-UHFFFAOYSA-N Tipranavir Natural products C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 SUJUHGSWHZTSEU-UHFFFAOYSA-N 0.000 abstract description 6
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 abstract description 6
- 229960001830 amprenavir Drugs 0.000 abstract description 6
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 abstract description 6
- 229960003277 atazanavir Drugs 0.000 abstract description 6
- AXRYRYVKAWYZBR-GASGPIRDSA-N atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 abstract description 6
- 229960001936 indinavir Drugs 0.000 abstract description 6
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 abstract description 6
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 abstract description 6
- 229960004525 lopinavir Drugs 0.000 abstract description 6
- 229960000884 nelfinavir Drugs 0.000 abstract description 6
- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 abstract description 6
- 229960000838 tipranavir Drugs 0.000 abstract description 6
- SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 abstract description 6
- 241000725303 Human immunodeficiency virus Species 0.000 abstract description 5
- 229960000366 emtricitabine Drugs 0.000 abstract description 5
- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 abstract description 4
- 229960001627 lamivudine Drugs 0.000 abstract description 4
- 229960000523 zalcitabine Drugs 0.000 abstract description 4
- 239000003443 antiviral agent Substances 0.000 abstract description 3
- 229960005319 delavirdine Drugs 0.000 abstract description 2
- 208000037357 HIV infectious disease Diseases 0.000 abstract 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 abstract 1
- VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical class OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 description 26
- 239000003814 drug Substances 0.000 description 25
- SCTJKHUUZLXJIP-RUZDIDTESA-N [(2r)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(3-hexadecoxypropoxy)phosphinic acid Chemical compound N1=CN=C2N(C[C@@H](C)OCP(O)(=O)OCCCOCCCCCCCCCCCCCCCC)C=NC2=C1N SCTJKHUUZLXJIP-RUZDIDTESA-N 0.000 description 24
- 229960004556 tenofovir Drugs 0.000 description 24
- 229940079593 drug Drugs 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 241000700605 Viruses Species 0.000 description 21
- 230000002195 synergetic effect Effects 0.000 description 18
- 239000000654 additive Substances 0.000 description 15
- 230000000996 additive effect Effects 0.000 description 15
- 230000003993 interaction Effects 0.000 description 14
- 230000029812 viral genome replication Effects 0.000 description 14
- 230000008485 antagonism Effects 0.000 description 12
- 230000035772 mutation Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 230000003042 antagnostic effect Effects 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 description 8
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 8
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 8
- 229960003804 efavirenz Drugs 0.000 description 8
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 8
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 8
- 230000010076 replication Effects 0.000 description 8
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 7
- 239000003623 enhancer Substances 0.000 description 7
- 102220638483 Protein PML_K65R_mutation Human genes 0.000 description 6
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000000798 anti-retroviral effect Effects 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- CZFFBEXEKNGXKS-UHFFFAOYSA-N raltegravir Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C CZFFBEXEKNGXKS-UHFFFAOYSA-N 0.000 description 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 5
- 101001007415 Homo sapiens LEM domain-containing protein 1 Proteins 0.000 description 5
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 5
- 102100028300 LEM domain-containing protein 1 Human genes 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 5
- 229960002555 zidovudine Drugs 0.000 description 5
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
- 229960004748 abacavir Drugs 0.000 description 4
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229960000689 nevirapine Drugs 0.000 description 4
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 4
- 229960004742 raltegravir Drugs 0.000 description 4
- 229960000329 ribavirin Drugs 0.000 description 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 4
- 229960001852 saquinavir Drugs 0.000 description 4
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 4
- 229960001203 stavudine Drugs 0.000 description 4
- 230000009044 synergistic interaction Effects 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000013270 controlled release Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000004404 heteroalkyl group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 3
- 231100000337 synergistic cytotoxicity Toxicity 0.000 description 3
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- 206010001513 AIDS related complex Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102100034343 Integrase Human genes 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
- CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 208000002672 hepatitis B Diseases 0.000 description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229940124524 integrase inhibitor Drugs 0.000 description 2
- 239000002850 integrase inhibitor Substances 0.000 description 2
- 229940111682 isentress Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 2
- 201000000317 pneumocystosis Diseases 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- YIBOMRUWOWDFLG-ONEGZZNKSA-N rilpivirine Chemical compound CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-ONEGZZNKSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 125000001831 (C6-C10) heteroaryl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- WYDKPTZGVLTYPG-UHFFFAOYSA-N 2,8-diamino-3,7-dihydropurin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N=C(N)N2 WYDKPTZGVLTYPG-UHFFFAOYSA-N 0.000 description 1
- CRYCZDRIXVHNQB-UHFFFAOYSA-N 2-amino-8-bromo-3,7-dihydropurin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N=C(Br)N2 CRYCZDRIXVHNQB-UHFFFAOYSA-N 0.000 description 1
- YCFWZXAEOXKNHL-UHFFFAOYSA-N 2-amino-8-chloro-3,7-dihydropurin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N=C(Cl)N2 YCFWZXAEOXKNHL-UHFFFAOYSA-N 0.000 description 1
- TXGWTBFCLADKKR-UHFFFAOYSA-N 2-amino-8-hydrazinyl-3,7-dihydropurin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N=C(NN)N2 TXGWTBFCLADKKR-UHFFFAOYSA-N 0.000 description 1
- DJGMEMUXTWZGIC-UHFFFAOYSA-N 2-amino-8-methyl-3,7-dihydropurin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N=C(C)N2 DJGMEMUXTWZGIC-UHFFFAOYSA-N 0.000 description 1
- MWBWWFOAEOYUST-UHFFFAOYSA-N 2-aminopurine Chemical compound NC1=NC=C2N=CNC2=N1 MWBWWFOAEOYUST-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BLXGZIDBSXVMLU-OWOJBTEDSA-N 5-[(e)-2-bromoethenyl]-1h-pyrimidine-2,4-dione Chemical compound Br\C=C\C1=CNC(=O)NC1=O BLXGZIDBSXVMLU-OWOJBTEDSA-N 0.000 description 1
- LQLQRFGHAALLLE-UHFFFAOYSA-N 5-bromouracil Chemical compound BrC1=CNC(=O)NC1=O LQLQRFGHAALLLE-UHFFFAOYSA-N 0.000 description 1
- ZRYZBEQILKESAW-UHFFFAOYSA-N 5-ethenyl-1h-pyrimidine-2,4-dione Chemical compound C=CC1=CNC(=O)NC1=O ZRYZBEQILKESAW-UHFFFAOYSA-N 0.000 description 1
- RHIULBJJKFDJPR-UHFFFAOYSA-N 5-ethyl-1h-pyrimidine-2,4-dione Chemical compound CCC1=CNC(=O)NC1=O RHIULBJJKFDJPR-UHFFFAOYSA-N 0.000 description 1
- KSNXJLQDQOIRIP-UHFFFAOYSA-N 5-iodouracil Chemical compound IC1=CNC(=O)NC1=O KSNXJLQDQOIRIP-UHFFFAOYSA-N 0.000 description 1
- UJBCLAXPPIDQEE-UHFFFAOYSA-N 5-prop-1-ynyl-1h-pyrimidine-2,4-dione Chemical compound CC#CC1=CNC(=O)NC1=O UJBCLAXPPIDQEE-UHFFFAOYSA-N 0.000 description 1
- JHEKLAXXCHLMNM-UHFFFAOYSA-N 5-propyl-1h-pyrimidine-2,4-dione Chemical compound CCCC1=CNC(=O)NC1=O JHEKLAXXCHLMNM-UHFFFAOYSA-N 0.000 description 1
- ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 1
- CLGFIVUFZRGQRP-UHFFFAOYSA-N 7,8-dihydro-8-oxoguanine Chemical compound O=C1NC(N)=NC2=C1NC(=O)N2 CLGFIVUFZRGQRP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XQUFBGFRRPVSOR-XMMPIXPASA-N C(CCCCCCCCCCCCCCC)OCCCC1=NC(=C2N=CN(C2=N1)C[C@@H](C)OCP(=O)(O)O)N Chemical compound C(CCCCCCCCCCCCCCC)OCCCC1=NC(=C2N=CN(C2=N1)C[C@@H](C)OCP(=O)(O)O)N XQUFBGFRRPVSOR-XMMPIXPASA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 108091026890 Coding region Proteins 0.000 description 1
- 206010048843 Cytomegalovirus chorioretinitis Diseases 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 229940124602 FDA-approved drug Drugs 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- 229940126656 GS-4224 Drugs 0.000 description 1
- 108010002459 HIV Integrase Proteins 0.000 description 1
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 241000224016 Plasmodium Species 0.000 description 1
- 241000233870 Pneumocystis Species 0.000 description 1
- 208000005384 Pneumocystis Pneumonia Diseases 0.000 description 1
- 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 description 1
- 108010020346 Polyglutamic Acid Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 206010037075 Protozoal infections Diseases 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 206010038997 Retroviral infections Diseases 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 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 description 1
- 206010044696 Tropical spastic paresis Diseases 0.000 description 1
- 241000347391 Umbrina cirrosa Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 229940124522 antiretrovirals Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000004556 brain Anatomy 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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004452 carbocyclyl group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 208000001763 cytomegalovirus retinitis Diseases 0.000 description 1
- 229940104302 cytosine Drugs 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- JOZGNYDSEBIJDH-UHFFFAOYSA-N eniluracil Chemical compound O=C1NC=C(C#C)C(=O)N1 JOZGNYDSEBIJDH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
- 229960004413 flucytosine Drugs 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000004030 hiv protease inhibitor Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- KHASNRBNVBIREH-IZEXYCQBSA-N methyl n-[(2s)-1-[[(5s)-5-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-6-phosphonooxyhexyl]amino]-1-oxo-3,3-diphenylpropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C([C@H](NC(=O)OC)C(=O)NCCCC[C@@H](COP(O)(O)=O)N(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)C1=CC=CC=C1 KHASNRBNVBIREH-IZEXYCQBSA-N 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000000274 microglia Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 229940098695 palmitic acid Drugs 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229960001355 tenofovir disoproxil Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 208000006961 tropical spastic paraparesis Diseases 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biotechnology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2363308P | 2008-01-25 | 2008-01-25 | |
| US23633 | 2008-01-25 | ||
| US10181008P | 2008-10-01 | 2008-10-01 | |
| US101810 | 2008-10-01 | ||
| PCT/US2009/000447 WO2009094190A2 (en) | 2008-01-25 | 2009-01-23 | Methods of treating viral infections |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2572631T3 true ES2572631T3 (es) | 2016-06-01 |
Family
ID=40901582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09704809.4T Active ES2572631T3 (es) | 2008-01-25 | 2009-01-23 | Métodos de tratamiento de infecciones virales |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8993542B2 (enExample) |
| EP (2) | EP3085377A1 (enExample) |
| JP (1) | JP5562255B2 (enExample) |
| CN (3) | CN102670628B (enExample) |
| AU (1) | AU2009206673B2 (enExample) |
| CA (1) | CA2713105C (enExample) |
| ES (1) | ES2572631T3 (enExample) |
| HK (1) | HK1225316A1 (enExample) |
| IL (2) | IL207170A (enExample) |
| MX (1) | MX2010008148A (enExample) |
| WO (2) | WO2009094191A2 (enExample) |
| ZA (1) | ZA201005737B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE032860T2 (en) | 2010-02-12 | 2017-11-28 | Chimerix Inc | A method for treating a virus infection |
| US9278135B2 (en) | 2010-04-26 | 2016-03-08 | Chimerix Inc. | Methods of treating retroviral infections and related dosage regimes |
| US8580294B2 (en) | 2010-10-19 | 2013-11-12 | International Partnership For Microbicides | Platinum-catalyzed intravaginal rings |
| CA2857490C (en) | 2011-12-22 | 2020-03-31 | Geron Corporation | Guanine analogs as telomerase substrates and telomere length affectors |
| EP2869823A4 (en) * | 2012-07-03 | 2016-03-16 | Chimerix Inc | METHOD FOR THE TREATMENT OF RETROVIRUS INFECTIONS AND RELATED DOSING PLANS |
| CN107312039B (zh) | 2012-08-30 | 2019-06-25 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药的制备方法 |
| WO2014085568A2 (en) * | 2012-11-27 | 2014-06-05 | Saint Louis University | Hbv rnase h purification and enzyme inhbitors |
| EP3401320B1 (en) | 2013-03-15 | 2020-05-13 | The Regents of the University of California | Acyclic nucleoside phosphonate diesters for use in treating human papilloma virus, cervical intraepithelial neoplasia, anal intraepithelial neoplasia, or vulvar intraepithelial neoplasia |
| US10137031B2 (en) | 2013-11-14 | 2018-11-27 | International Partnership For Microbicides, Inc. | Combination therapy intravaginal rings |
| EP3077403A4 (en) * | 2013-12-05 | 2017-08-02 | Chimerix, Inc. | Branched chain acyclic nucleoside phosphonate esters and methods of synthesis and uses thereof |
| RS63250B1 (sr) | 2014-09-15 | 2022-06-30 | Univ California | Nukleotidni analozi |
| WO2017048956A1 (en) | 2015-09-15 | 2017-03-23 | The Regents Of The University Of California | Nucleotide analogs |
| 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 |
| US11400186B2 (en) * | 2016-05-12 | 2022-08-02 | Merck Sharp & Dohme Llc | Drug delivery system for the delivery of antiviral agents |
| AR111464A1 (es) | 2017-04-14 | 2019-07-17 | Contravir Pharmaceuticals Inc | Terapia combinada para el tratamiento de infecciones virales |
| TW201912153A (zh) * | 2017-08-30 | 2019-04-01 | 加拿大商愛彼特生物製藥公司 | 用於治療ｂ型肝炎的化合物、醫藥組合物及方法 |
| CA3262284A1 (en) | 2022-07-21 | 2024-01-25 | Antiva Biosciences, Inc. | Pharmaceutical compositions and forms for the treatment of human papillomavirus (HPV) infection and HPV-induced neoplasm |
Family Cites Families (161)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1944530A (en) * | 1929-04-08 | 1934-01-23 | Ig Farbenindustrie Ag | Phosphoric acid esters |
| CA777769A (en) * | 1963-03-18 | 1968-02-06 | H. Roy Clarence | Substituted methylene diphosphonic acid compounds and detergent compositions |
| DE1248654B (de) * | 1964-11-11 | 1967-08-31 | Albright & Wilson (Mf g) Limited, Oldbury, Warwickshire (Großbritannien) | Verfahren zur Herstellung von Phosphonsäuren und deren Salzen |
| DE2009341C3 (de) | 1970-02-27 | 1979-06-21 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | 3-Octadecyloxy-propanol-(l)-phosphorsäure-monocholinester und Verfahren zu dessen Herstellung |
| DE2943498C2 (de) * | 1979-10-27 | 1983-01-27 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur Herstellung von 3-Amino-1-hydroxypropan-1,1-diphosphonsäure |
| DE3164332D1 (en) * | 1980-10-21 | 1984-07-26 | Boehringer Mannheim Gmbh | Phospholipids that contain sulphur, process for their preparation and medicines containing these compounds |
| CS220713B1 (cs) | 1981-06-02 | 1983-04-29 | Antonin Holy | Dialkylestery kyseliny p-toluensulfonyloxymethanfosfonové a způsob jejich přípravy |
| DE3374837D1 (en) * | 1982-02-17 | 1988-01-21 | Ciba Geigy Ag | Lipids in the aqueous phase |
| US4562179A (en) | 1982-04-19 | 1985-12-31 | Fujisawa Pharmaceutical Co., Ltd. | Phospholipid derivatives, and pharmaceutical composition of the same |
| US5047533A (en) * | 1983-05-24 | 1991-09-10 | Sri International | Acyclic purine phosphonate nucleotide analogs |
| IT1196315B (it) * | 1984-10-29 | 1988-11-16 | Gentili Ist Spa | Procedimento per la preparazione di acidi difosfonici |
| IL77243A (en) | 1984-12-21 | 1996-11-14 | Procter & Gamble | Pharmaceutical compositions containing geminal diphosphonic acid compounds and certain such novel compounds |
| JPS61152694A (ja) | 1984-12-27 | 1986-07-11 | Toyama Chem Co Ltd | 新規な５−フルオロ−２′−デオキシウリジン−５′−ホスフエ−ト誘導体およびその塩 |
| US5223263A (en) * | 1988-07-07 | 1993-06-29 | Vical, Inc. | Liponucleotide-containing liposomes |
| US6448392B1 (en) * | 1985-03-06 | 2002-09-10 | Chimerix, Inc. | Lipid derivatives of antiviral nucleosides: liposomal incorporation and method of use |
| GB8530603D0 (en) * | 1985-12-12 | 1986-01-22 | Leo Pharm Prod Ltd | Chemical compounds |
| DE3623397A1 (de) * | 1986-07-11 | 1988-01-14 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| CS264222B1 (en) * | 1986-07-18 | 1989-06-13 | Holy Antonin | N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them |
| US5650510A (en) | 1986-11-18 | 1997-07-22 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Antiviral phosphonomethoxyalkylene purine and pyrimidine derivatives |
| US5247085A (en) * | 1987-11-30 | 1993-09-21 | Beecham Group P.L.C. | Antiviral purine compounds |
| SU1548182A1 (ru) * | 1987-12-29 | 1990-03-07 | Институт молекулярной биологии АН СССР | 5 @ -Фосфонаты 3 @ -азидо-2 @ ,3 @ -дидезоксинуклеозидов, вл ющиес специфическими ингибиторами вируса СПИД в культуре лимфоцитов человека Н9/ШВ |
| US5817638A (en) * | 1988-07-07 | 1998-10-06 | Nexstar Pharmaceuticals, Inc. | Antiviral liponucleosides: treatment of hepatitis B |
| US6252060B1 (en) * | 1988-07-07 | 2001-06-26 | Nexstar Pharmaceuticals, Inc. | Antiviral liponucleosides: treatment of hepatitis B |
| CA2001401A1 (en) * | 1988-10-25 | 1990-04-25 | Claude Piantadosi | Quaternary amine containing ether or ester lipid derivatives and therapeutic compositions |
| US5411947A (en) * | 1989-06-28 | 1995-05-02 | Vestar, Inc. | Method of converting a drug to an orally available form by covalently bonding a lipid to the drug |
| US5194654A (en) * | 1989-11-22 | 1993-03-16 | Vical, Inc. | Lipid derivatives of phosphonoacids for liposomal incorporation and method of use |
| US5196409A (en) * | 1989-08-20 | 1993-03-23 | Yissum, Research Development Company Of The Hebrew University Of Jerusalem | Bisphosphonates, pharmaceutical compositions, and process for the treatment of irregularities in calcium metabolism |
| IL91362A0 (en) * | 1989-08-20 | 1990-03-19 | Yissum Res Dev Co | Bisphosphonates,process for preparing them and pharmaceutical compositions containing them |
| IT1241674B (it) * | 1989-10-12 | 1994-01-27 | Boehringer Biochemia Srl | Acidi gem-difosfonici, un processo per la loro preparazione e composizioni farmaceutiche che li contengono. |
| DE3934820A1 (de) | 1989-10-19 | 1991-04-25 | Boehringer Mannheim Gmbh | Verwendung von lecithin-analoga als antivirale arzneimittel und neue derivate |
| US5463092A (en) * | 1989-11-22 | 1995-10-31 | Vestar, Inc. | Lipid derivatives of phosphonacids for liposomal incorporation and method of use |
| DE3942933A1 (de) | 1989-12-23 | 1991-06-27 | Boehringer Mannheim Gmbh | Verwendung von alkylphospholipiden als antivirale arzneimittel und neue phospholipid-derivate |
| US5914331A (en) | 1990-02-01 | 1999-06-22 | Emory University | Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane |
| CA2083961A1 (en) * | 1990-05-29 | 1991-11-30 | Henk Van Den Bosch | Synthesis of glycerol di- and triphosphate derivatives |
| WO1992002511A1 (en) | 1990-08-10 | 1992-02-20 | Bristol-Myers Squibb Company | Novel process for the preparation of nucleotides |
| DE4026265A1 (de) * | 1990-08-20 | 1992-02-27 | Boehringer Mannheim Gmbh | Neue phospholipid-derivate von nucleosiden, deren herstellung sowie deren verwendung als antivirale arzneimittel |
| ES2118069T3 (es) * | 1990-09-14 | 1998-09-16 | Acad Of Science Czech Republic | Profarmacos de fosfonatos. |
| FI89365C (fi) * | 1990-12-20 | 1993-09-27 | Leiras Oy | Foerfarande foer framstaellning av nya farmakologiskt anvaendbara metylenbisfosfonsyraderivat |
| US5183815A (en) * | 1991-01-22 | 1993-02-02 | Merck & Co., Inc. | Bone acting agents |
| US5672697A (en) * | 1991-02-08 | 1997-09-30 | Gilead Sciences, Inc. | Nucleoside 5'-methylene phosphonates |
| US5300687A (en) * | 1991-07-18 | 1994-04-05 | Ortho Pharmaceutical Corporation | Trifluoromethylbenzylphosphonates useful in treating osteoporosis |
| US5879700A (en) | 1991-10-15 | 1999-03-09 | Hostetler; Karl Y. | Nucleoside analogue phosphates for topical use |
| JP3141053B2 (ja) * | 1991-12-26 | 2001-03-05 | アベンティス ファーマ株式会社 | ビスホスホン酸誘導体 |
| JPH07507317A (ja) * | 1992-05-29 | 1995-08-10 | プロクター、エンド、ギャンブル、ファーマスーティカルズ、インコーポレーテッド | 異常なカルシウムおよびホスフェート代謝を治療するためのチオ置換窒素含有複素環式ホスホネート化合物 |
| US5519021A (en) | 1992-08-07 | 1996-05-21 | Merck & Co., Inc. | Benzoxazinones as inhibitors of HIV reverse transcriptase |
| DE59309360D1 (de) * | 1992-12-02 | 1999-03-18 | Hoechst Ag | Guanidinalkyl-1, 1-bisphosphonsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US5512671A (en) * | 1993-02-16 | 1996-04-30 | Wake Forest University | Ether lipid-nucleoside covalent conjugates |
| US5817647A (en) * | 1993-04-01 | 1998-10-06 | Merrell Pharmaceuticals Inc. | Unsaturated acetylene phosphonate derivatives of purines |
| US5484911A (en) * | 1993-04-01 | 1996-01-16 | Health Research, Inc. | Nucleoside 5'-diphosphate conjugates of ether lipids |
| EP0702556B1 (en) * | 1993-06-10 | 2002-10-23 | Wake Forest University | (phospho)lipids for combatting hepatitis b virus infection |
| EP0632048B1 (en) | 1993-06-29 | 2001-03-21 | Mitsubishi Chemical Corporation | Phosphonate-nucleotide ester derivatives |
| US5798340A (en) * | 1993-09-17 | 1998-08-25 | Gilead Sciences, Inc. | Nucleotide analogs |
| US5656745A (en) * | 1993-09-17 | 1997-08-12 | Gilead Sciences, Inc. | Nucleotide analogs |
| WO1995007919A1 (en) * | 1993-09-17 | 1995-03-23 | Gilead Sciences, Inc. | Method for dosing therapeutic compounds |
| 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 |
| CA2185699A1 (en) * | 1994-04-04 | 1995-10-12 | William R. Freeman | Use of phosphonylmethoxyalkyl nucleosides for the treatment of raised intraocular pressure |
| US6207646B1 (en) * | 1994-07-15 | 2001-03-27 | University Of Iowa Research Foundation | Immunostimulatory nucleic acid molecules |
| US6239116B1 (en) * | 1994-07-15 | 2001-05-29 | University Of Iowa Research Foundation | Immunostimulatory nucleic acid molecules |
| JP3468773B2 (ja) * | 1994-07-15 | 2003-11-17 | ザ ユニバーシティ オブ アイオワ リサーチ ファウンデーション | 免疫調節オリゴヌクレオチド |
| DE69535758D1 (de) * | 1994-08-29 | 2008-07-03 | Univ Wake Forest | Lipid-analoge zur behandlung von viralen infektionen |
| US7135584B2 (en) | 1995-08-07 | 2006-11-14 | Wake Forest University | Lipid analogs for treating viral infections |
| US5696277A (en) | 1994-11-15 | 1997-12-09 | Karl Y. Hostetler | Antiviral prodrugs |
| US5627185A (en) * | 1994-11-23 | 1997-05-06 | Gosselin; Gilles | Acyclovir derivatives as antiviral agents |
| 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 |
| EP0753523A1 (en) | 1995-07-10 | 1997-01-15 | Gador S.A. | Amino-substituted bisphosphonic acids |
| US5885973A (en) * | 1995-12-27 | 1999-03-23 | Gador, S.A. | Bone mass anabolic composition comprising olpadronate |
| US5717095A (en) * | 1995-12-29 | 1998-02-10 | Gilead Sciences, Inc. | Nucleotide analogs |
| CA2195262C (en) * | 1996-01-18 | 2005-08-09 | Masaru Ubasawa | Phosphonate nucleotide compounds |
| FR2746801B1 (fr) | 1996-03-27 | 1998-05-07 | Ceca Sa | Esters phosphoriques d'alkyl ou d'acyl dianhydro-1,4:3,6-d- glucitol, procede de preparation et utilisations |
| 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 |
| US5760013A (en) * | 1996-08-21 | 1998-06-02 | National Science Council | Thymidylate analogs and the use thereof |
| DE69737385T2 (de) | 1996-12-19 | 2007-10-25 | Kao Corp. | Zusammensetzung für die beschichtung von zähnen |
| US6818629B2 (en) | 1997-02-10 | 2004-11-16 | Inspire Pharmaceuticals, Inc. | Pharmaceutical formulation comprising P1-(2'-deoxycytidine 5'-)P4-(uridine 5'-) tetraphosphate |
| US6686462B2 (en) | 1997-02-28 | 2004-02-03 | The Regents Of The University Of California | Antiviral compounds and methods of administration |
| US6589940B1 (en) * | 1997-06-06 | 2003-07-08 | Dynavax Technologies Corporation | Immunostimulatory oligonucleotides, compositions thereof and methods of use thereof |
| ATE432348T1 (de) * | 1997-06-06 | 2009-06-15 | Univ California | Inhibitoren von immunstimulatorischen dna sequenz aktivität |
| US5935946A (en) * | 1997-07-25 | 1999-08-10 | Gilead Sciences, Inc. | Nucleotide analog composition and synthesis method |
| WO1999009139A1 (en) * | 1997-08-15 | 1999-02-25 | Rubicon Laboratory, Inc. | Retrovirus and viral vectors |
| NZ550116A (en) | 1997-08-18 | 2008-03-28 | Neurochem Int Ltd | Phosphono-carboxylate compounds for treating amyloidosis |
| CA2323929C (en) * | 1998-04-03 | 2004-03-09 | University Of Iowa Research Foundation | Methods and products for stimulating the immune system using immunotherapeutic oligonucleotides and cytokines |
| EP1083897A4 (en) | 1998-06-03 | 2003-01-02 | Merck & Co Inc | HIV INTEGRASE INHIBITORS |
| EP1082121A4 (en) | 1998-06-03 | 2003-02-05 | Merck & Co Inc | HIV integrase |
| US6562798B1 (en) * | 1998-06-05 | 2003-05-13 | Dynavax Technologies Corp. | Immunostimulatory oligonucleotides with modified bases and methods of use thereof |
| FR2781228B1 (fr) | 1998-07-16 | 2000-09-29 | Pf Medicament | Phosphonates insatures derives d'indole |
| WO2000006588A1 (en) | 1998-07-27 | 2000-02-10 | University Of Iowa Research Foundation | STEREOISOMERS OF CpG OLIGONUCLEOTIDES AND RELATED METHODS |
| AU6425999A (en) | 1998-10-09 | 2000-05-01 | Dynavax Technologies Corporation | Anti hiv compositions comprising immunostimulatory polynucleotides and hiv antigens |
| AU3118200A (en) | 1998-12-14 | 2000-07-03 | Merck & Co., Inc. | Hiv integrase inhibitors |
| DE19859426A1 (de) | 1998-12-22 | 2000-07-06 | Hassan Jomaa | Verwendung von phosphororganischen Verbindungen zur therapeutischen und prophylaktischen Behandlung von Infektionen |
| RU2225860C2 (ru) | 1998-12-25 | 2004-03-20 | Шионоги & Ко., Лтд. | Ароматические гетероциклические соединения, обладающие активностью в отношении вич-интегразы |
| TR200202129T2 (tr) | 1999-06-02 | 2003-03-21 | Shionogi & Co., Ltd. | Yeni ikameli propenon türevlerinin hazırlanması için prosesler. |
| WO2001000578A1 (en) | 1999-06-25 | 2001-01-04 | Merck & Co., Inc. | 1-(aromatic- or heteroaromatic-substituted)-3-(heteroaromatic substituted)-1,3-propanediones and uses thereof |
| US6245806B1 (en) | 1999-08-03 | 2001-06-12 | Merck & Co., Inc. | HIV integrase inhibitors |
| US7479285B1 (en) | 1999-08-19 | 2009-01-20 | Dynavax Technologies Corporation | Methods of modulating an immune response using immunostimulatory sequences and compositions for use therein |
| ES2218216T3 (es) | 1999-09-24 | 2004-11-16 | Shire Biochem Inc. | Analogos de nucleosidos de dioxolano para el tratamiento o la prevencion de infecciones viricas. |
| SK287400B6 (sk) | 1999-09-25 | 2010-08-09 | University Of Iowa Research Foundation | Prostriedok s obsahom imunostimulačnej nukleovej kyseliny a jeho použitie na stimuláciu imunitnej reakcie |
| AU783118B2 (en) | 1999-09-27 | 2005-09-29 | Coley Pharmaceutical Gmbh | Methods related to immunostimulatory nucleic acid-induced interferon |
| WO2001027309A1 (en) | 1999-10-13 | 2001-04-19 | Merck & Co., Inc. | Hiv integrase inhibitors |
| US6670341B1 (en) | 1999-10-28 | 2003-12-30 | Wake Forest University Health Sciences | Compositions and methods for double-targeting virus infections and targeting cancer cells |
| US7026469B2 (en) * | 2000-10-19 | 2006-04-11 | Wake Forest University School Of Medicine | Compositions and methods of double-targeting virus infections and cancer cells |
| BR0016058A (pt) * | 1999-12-03 | 2003-07-15 | Univ California San Diego | Compostos de fosfonato |
| EP1914237B1 (en) | 1999-12-03 | 2014-06-18 | The Regents of The University of California | Phosphonate ester antiviral compounds |
| EP1118333A1 (en) | 2000-01-18 | 2001-07-25 | Eurand International S.P.A. | Compositions with enhanced oral bioavailability |
| US20020136757A1 (en) * | 2000-01-28 | 2002-09-26 | Samuel Baron | Methods and devices for preventing transmission of sexually transmitted diseases |
| EP1253894A4 (en) * | 2000-01-28 | 2005-01-26 | Univ Texas | Methods and devices for preventing transmission of sexually transmitted diseases |
| DK1301519T4 (da) * | 2000-07-21 | 2021-12-20 | Gilead Sciences Inc | Prodrugs af phosphonatnukleotidanaloger og fremgangsmåder til udvælgelse og fremstilling heraf |
| EP1326611B1 (en) | 2000-10-12 | 2007-06-13 | Merck & Co., Inc. | Aza- and polyaza-naphthalenyl-carboxamides useful as hiv integrase inhibitors |
| IL155089A0 (en) | 2000-10-12 | 2003-10-31 | Merck & Co Inc | Aza and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| CA2425625A1 (en) | 2000-10-12 | 2002-07-18 | Merck & Co., Inc. | Aza-and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| US20050010048A1 (en) | 2000-10-12 | 2005-01-13 | Linghang Zhuang | Aza-and polyaza-naphthalenly ketones useful as hiv integrase inhibitors |
| US7288265B1 (en) * | 2000-10-16 | 2007-10-30 | Lectec Corporation | Treating viral infection at smallpox vaccination site |
| US7309696B2 (en) * | 2000-10-19 | 2007-12-18 | Wake Forest University | Compositions and methods for targeting cancer cells |
| WO2002040021A2 (en) | 2000-11-17 | 2002-05-23 | Idenix (Cayman) Limited | Methods for inhibiting the transmission of hiv using topically applied substituted 6-benzyl-4-oxopyrimidines |
| US6605602B1 (en) * | 2001-09-28 | 2003-08-12 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Method of treating BK virus nephropathy |
| CA2471968C (en) | 2001-10-06 | 2013-07-23 | Merial Limited | Immunostimulatory nucleic acids and use thereof |
| HUP0500028A2 (hu) | 2001-10-23 | 2005-04-28 | Ono Pharmaceutical Co., Ltd. | Triaza-spiro[5.5]undekán-azármazék citokróm P450 izozim 3A4 inhibitorral és/vagy P-glikoprotein inhibitorral való kombinációját tartalmazó gyógyszer |
| US20040022873A1 (en) * | 2001-11-09 | 2004-02-05 | Guilford F. Timothy | Systemic administration of NAC as an adjunct in the treatment of bioterror exposures such as anthrax, smallpox or radiation and for vaccination prophylaxis, and use in combination with DHEA for the treatment of smallpox and other viruses |
| US20040071757A1 (en) * | 2001-11-20 | 2004-04-15 | David Rolf | Inhalation antiviral patch |
| TWI286476B (en) | 2001-12-12 | 2007-09-11 | Tibotec Pharm Ltd | Combination of cytochrome P450 dependent protease inhibitors |
| AU2003210659A1 (en) | 2002-01-24 | 2003-09-02 | Sangstat Medical Corporation | Combination therapy for treatment of hiv infection |
| JP4942915B2 (ja) * | 2002-04-26 | 2012-05-30 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｉｖプロテアーゼ阻害剤化合物のホスホネートアナログの細胞蓄積 |
| AU2003301439A1 (en) | 2002-10-16 | 2004-05-04 | Gilead Sciences, Inc. | Pre-organized tricyclic integrase inhibitor compounds |
| WO2004062600A2 (en) * | 2003-01-08 | 2004-07-29 | Lectec Corporation | Antiviral patch |
| NZ540728A (en) | 2003-01-14 | 2008-08-29 | Gilead Sciences Inc | Compositions and methods for combination antiviral therapy |
| US20050261237A1 (en) | 2003-04-25 | 2005-11-24 | Boojamra Constantine G | Nucleoside phosphonate analogs |
| AP2005003451A0 (en) | 2003-04-28 | 2005-12-31 | Tibotec Pharm Ltd | HIV integrase inhibitors. |
| DK1638938T3 (en) | 2003-06-20 | 2017-07-31 | Siga Tech Inc | Compounds, Compositions and Methods for the Treatment and Prevention of Orthopox Virus Infections and Related Diseases |
| TW200510425A (en) | 2003-08-13 | 2005-03-16 | Japan Tobacco Inc | Nitrogen-containing fused ring compound and use thereof as HIV integrase inhibitor |
| WO2005090370A1 (en) * | 2004-02-05 | 2005-09-29 | The Regents Of The University Of California | Pharmacologically active agents containing esterified phosphonates and methods for use thereof |
| US20060052346A1 (en) | 2004-02-17 | 2006-03-09 | Averett Devron R | Nucleoside phosphonate derivatives useful in the treatment of HIV infections |
| US20050187192A1 (en) * | 2004-02-20 | 2005-08-25 | Kucera Pharmaceutical Company | Phospholipids for the treatment of infection by togaviruses, herpes viruses and coronaviruses |
| WO2005087788A2 (en) | 2004-03-04 | 2005-09-22 | The Regents Of The University Of California | Methods for preparation of nucleoside phosphonate esters |
| WO2006076015A2 (en) * | 2004-04-30 | 2006-07-20 | The Regents Of The University Of California | 1-[2-(phosphonomethoxy)ethyl]-cytosine and analogs thereof |
| WO2005121378A2 (en) | 2004-06-03 | 2005-12-22 | Saint Louis University | Methods and compositions for vaccination |
| UA93354C2 (ru) | 2004-07-09 | 2011-02-10 | Гилиад Сайенсиз, Инк. | Местный противовирусный препарат |
| US20080020018A1 (en) * | 2004-09-27 | 2008-01-24 | Joey Moodley | Combination Products |
| EP1831235B1 (en) | 2004-12-16 | 2013-02-20 | The Regents of The University of California | Lung-targeted drugs |
| US7250421B2 (en) | 2005-01-31 | 2007-07-31 | University Of Georgia Research Foundation, Inc. | Diketo acids with nucleobase scaffolds: anti-HIV replication inhibitors targeted at HIV integrase |
| TW200714289A (en) | 2005-02-28 | 2007-04-16 | Genentech Inc | Treatment of bone disorders |
| US20090156545A1 (en) * | 2005-04-01 | 2009-06-18 | Hostetler Karl Y | Substituted Phosphate Esters of Nucleoside Phosphonates |
| US8642577B2 (en) | 2005-04-08 | 2014-02-04 | Chimerix, Inc. | Compounds, compositions and methods for the treatment of poxvirus infections |
| JP2008538354A (ja) * | 2005-04-08 | 2008-10-23 | キメリクス，インコーポレイテッド | ウイルス感染症およびその他の内科疾患を治療するための化合物、組成物および方法 |
| EP1888581A2 (en) | 2005-05-16 | 2008-02-20 | Gilead Sciences, Inc. | Hiv-integrase inhibitor compounds |
| TWI471145B (zh) | 2005-06-13 | 2015-02-01 | Bristol Myers Squibb & Gilead Sciences Llc | 單一式藥學劑量型 |
| US9044509B2 (en) | 2006-02-03 | 2015-06-02 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Inhibition of HIV infection through chemoprophylaxis |
| CN100396689C (zh) * | 2006-03-07 | 2008-06-25 | 中国医学科学院医药生物技术研究所 | 一组具有抑制hiv-1/hbv病毒复制活性的替诺福韦单酯化合物 |
| WO2007130783A2 (en) | 2006-05-03 | 2007-11-15 | Chimerix, Inc. | Metabolically stable alkoxyalkyl esters of antiviral or antiproliferative phosphonates, nucleoside phosphonates and nucleoside phosphates |
| AP2985A (en) | 2006-07-07 | 2014-09-30 | Gilead Sciences Inc | Modulators of pharmacokinetic properties of therapeutics |
| EP2046792B1 (en) | 2006-07-12 | 2015-02-25 | Mylan Laboratories Limited | Process for the preparation of tenofovir |
| US20080161324A1 (en) * | 2006-09-14 | 2008-07-03 | Johansen Lisa M | Compositions and methods for treatment of viral diseases |
| EP2125024B1 (en) | 2007-03-23 | 2013-02-13 | TO-BBB Holding B.V. | Targeted intracellular delivery of antiviral agents |
| WO2008133982A2 (en) | 2007-04-27 | 2008-11-06 | Lectec Corporation | Adhesive patch with aversive agent |
| EP2155257B1 (en) | 2007-04-27 | 2016-10-05 | Chimerix, Inc. | Methods of reducing nephrotoxicity in subjects administered with nucleoside |
| EP2160468B1 (en) | 2007-05-21 | 2012-01-11 | Saint Louis University | Screening tool for antiviral agents |
| US20090111774A1 (en) * | 2007-06-01 | 2009-04-30 | Luitpold Pharmaceuticals, Inc. | Pmea lipid conjugates |
| JP2011508747A (ja) * | 2008-01-03 | 2011-03-17 | バイロケム ファーマ インコーポレイテッド | 新規のｃ−２１ケトルパン誘導体、それらの調製および使用 |
| CN101981047A (zh) * | 2008-01-03 | 2011-02-23 | Viro化学制药公司 | 新的羽扇烷衍生物 |
| WO2011011519A1 (en) | 2009-07-21 | 2011-01-27 | Chimerix, Inc. | Compounds, compositions and methods for treating ocular conditions |
| EP2462152A4 (en) | 2009-08-03 | 2013-02-13 | Chimerix Inc | COMPOSITION AND METHOD FOR THE TREATMENT OF VIRUS INFECTIONS AND TEMPORED VIRUSES |
| CA2779473C (en) | 2009-10-30 | 2016-08-16 | Chimerix, Inc. | Methods of treating viral associated diseases |
| HUE032860T2 (en) * | 2010-02-12 | 2017-11-28 | Chimerix Inc | A method for treating a virus infection |
-
2009
- 2009-01-23 CN CN201210080173.XA patent/CN102670628B/zh not_active Expired - Fee Related
- 2009-01-23 ES ES09704809.4T patent/ES2572631T3/es active Active
- 2009-01-23 WO PCT/US2009/000448 patent/WO2009094191A2/en not_active Ceased
- 2009-01-23 JP JP2010544347A patent/JP5562255B2/ja not_active Expired - Fee Related
- 2009-01-23 CN CN2009801097904A patent/CN101977610B/zh not_active Expired - Fee Related
- 2009-01-23 CA CA2713105A patent/CA2713105C/en not_active Expired - Fee Related
- 2009-01-23 EP EP16151475.7A patent/EP3085377A1/en not_active Withdrawn
- 2009-01-23 US US12/864,431 patent/US8993542B2/en active Active
- 2009-01-23 EP EP09704809.4A patent/EP2254582B1/en not_active Not-in-force
- 2009-01-23 WO PCT/US2009/000447 patent/WO2009094190A2/en not_active Ceased
- 2009-01-23 AU AU2009206673A patent/AU2009206673B2/en not_active Ceased
- 2009-01-23 MX MX2010008148A patent/MX2010008148A/es active IP Right Grant
- 2009-01-23 CN CN201510598946.7A patent/CN105055432A/zh active Pending
-
2010
- 2010-07-22 IL IL207170A patent/IL207170A/en active IP Right Grant
- 2010-08-11 ZA ZA2010/05737A patent/ZA201005737B/en unknown
-
2015
- 2015-11-09 IL IL242518A patent/IL242518A/en not_active IP Right Cessation
-
2016
- 2016-12-01 HK HK16113767.6A patent/HK1225316A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN105055432A (zh) | 2015-11-18 |
| EP2254582B1 (en) | 2016-01-20 |
| AU2009206673B2 (en) | 2015-04-23 |
| CN102670628A (zh) | 2012-09-19 |
| MX2010008148A (es) | 2010-10-20 |
| CN101977610B (zh) | 2012-05-16 |
| CN102670628B (zh) | 2015-11-25 |
| JP2011510077A (ja) | 2011-03-31 |
| CA2713105C (en) | 2016-06-07 |
| IL242518A (en) | 2017-07-31 |
| US8993542B2 (en) | 2015-03-31 |
| WO2009094190A2 (en) | 2009-07-30 |
| WO2009094191A3 (en) | 2009-10-01 |
| EP2254582A2 (en) | 2010-12-01 |
| ZA201005737B (en) | 2012-04-25 |
| IL207170A0 (en) | 2010-12-30 |
| CA2713105A1 (en) | 2009-07-30 |
| AU2009206673A1 (en) | 2009-07-30 |
| US20110021464A1 (en) | 2011-01-27 |
| WO2009094190A3 (en) | 2009-10-01 |
| CN101977610A (zh) | 2011-02-16 |
| EP3085377A1 (en) | 2016-10-26 |
| EP2254582A4 (en) | 2011-07-20 |
| HK1151237A1 (zh) | 2012-01-27 |
| WO2009094191A2 (en) | 2009-07-30 |
| JP5562255B2 (ja) | 2014-07-30 |
| IL207170A (en) | 2016-11-30 |
| HK1225316A1 (en) | 2017-09-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2572631T3 (es) | Métodos de tratamiento de infecciones virales | |
| De Clercq | The clinical potential of the acyclic (and cyclic) nucleoside phosphonates. The magic of the phosphonate bond | |
| TWI807399B (zh) | 磷脂化合物及其用途 | |
| AU2024205205A1 (en) | Methods for treating SARS CoV-2 infections | |
| ES2941240T3 (es) | Inhibidores de la replicación del virus de la inmunodeficiencia humana | |
| JP2006524711A5 (enExample) | ||
| HRP20210732T1 (hr) | Supstituirani spojevi 8-oksetan-3-il-3,8-diazabiciklo[3.2.1]oktan-3-ila kao inhibitori hiv-a | |
| JP2025526742A (ja) | ステロール系イオン化脂質及びそれを含む脂質ナノ粒子 | |
| PL408254A1 (pl) | Kompozycje i i sposoby wykorzystywane w skojarzonej terapii przeciwwirusowej | |
| De Clercq | The Holý Trinity: the acyclic nucleoside phosphonates | |
| US20240165143A1 (en) | 4'-halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto | |
| US20250281519A1 (en) | Nucleotide and nucleoside therapeutic compositions, combinations and uses related thereto | |
| CN104797259A (zh) | 治疗逆转录病毒感染的方法和相关剂量方案 | |
| JPWO2023102529A5 (enExample) | ||
| Krovi et al. | Injectable long-acting human immunodeficiency virus antiretroviral prodrugs with improved pharmacokinetic profiles | |
| JPWO2023102523A5 (enExample) | ||
| EA049672B1 (ru) | Фосфолипидные соединения и варианты их применения | |
| Prichard et al. | Cyclopropavir inhibits the normal function of the human cytomegalovirus UL97 kinase | |
| AU2024267852A1 (en) | 4'-halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto | |
| Cardin et al. | In vivo efficacy of N-methanocarbathymidine (N-MCT) against herpes simplex virus type 2 in neonatal guinea pigs | |
| Nadal et al. | Structural and functional characterization of human cytomegalovirus terminase leads to a new antiviral target | |
| HK1151237B (en) | Methods of treating viral infections | |
| Lou | Development of Tivantinib as Treatment for Hepatocellular Carcinoma | |
| EA047160B1 (ru) | Терапевтические композиции 4'-галогенсодержащих нуклеотидов и нуклеозидов и их применение |