NZ536570A - Methods and compositions for treating flaviviruses and pestiviruses - Google Patents
Methods and compositions for treating flaviviruses and pestivirusesInfo
- Publication number
- NZ536570A NZ536570A NZ536570A NZ53657001A NZ536570A NZ 536570 A NZ536570 A NZ 536570A NZ 536570 A NZ536570 A NZ 536570A NZ 53657001 A NZ53657001 A NZ 53657001A NZ 536570 A NZ536570 A NZ 536570A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- compound
- pharmaceutically acceptable
- monophosphate
- acyl
- Prior art date
Links
- 241000710831 Flavivirus Species 0.000 title claims abstract description 54
- 241000710778 Pestivirus Species 0.000 title claims description 38
- 238000000034 method Methods 0.000 title description 55
- 239000000203 mixture Substances 0.000 title description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 510
- -1 nucleoside compounds Chemical class 0.000 claims abstract description 240
- 125000002252 acyl group Chemical group 0.000 claims abstract description 211
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 190
- 239000010452 phosphate Substances 0.000 claims abstract description 189
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 185
- 239000001177 diphosphate Substances 0.000 claims abstract description 162
- 235000011180 diphosphates Nutrition 0.000 claims abstract description 162
- 235000011178 triphosphate Nutrition 0.000 claims abstract description 154
- 239000001226 triphosphate Substances 0.000 claims abstract description 153
- 229940002612 prodrug Drugs 0.000 claims abstract description 152
- 239000000651 prodrug Substances 0.000 claims abstract description 152
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims abstract description 130
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims abstract description 118
- 150000004712 monophosphates Chemical class 0.000 claims abstract description 100
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims abstract description 94
- 239000002777 nucleoside Substances 0.000 claims abstract description 92
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 89
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 87
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 71
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 66
- IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 claims abstract description 64
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 61
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 56
- 238000011282 treatment Methods 0.000 claims abstract description 48
- 239000003814 drug Substances 0.000 claims abstract description 34
- 208000004571 Pestivirus Infections Diseases 0.000 claims abstract description 31
- 206010054261 Flavivirus infection Diseases 0.000 claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims description 229
- 229910052739 hydrogen Inorganic materials 0.000 claims description 156
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 147
- 239000001257 hydrogen Substances 0.000 claims description 144
- 150000003839 salts Chemical class 0.000 claims description 124
- 229940104302 cytosine Drugs 0.000 claims description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 62
- 229960000643 adenine Drugs 0.000 claims description 61
- 238000001727 in vivo Methods 0.000 claims description 54
- 229940024606 amino acid Drugs 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 229930024421 Adenine Natural products 0.000 claims description 44
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 43
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 38
- 208000005176 Hepatitis C Diseases 0.000 claims description 36
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 34
- 208000015181 infectious disease Diseases 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 25
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical group CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 24
- 239000003085 diluting agent Substances 0.000 claims description 23
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 22
- 239000003937 drug carrier Substances 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 229940113082 thymine Drugs 0.000 claims description 12
- 230000003441 anti-flavivirus Effects 0.000 claims description 11
- 229940035893 uracil Drugs 0.000 claims description 11
- 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 claims description 8
- 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 claims description 8
- 229960000329 ribavirin Drugs 0.000 claims description 8
- 241000282414 Homo sapiens Species 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000002718 pyrimidine nucleoside Substances 0.000 claims description 6
- 102000014150 Interferons Human genes 0.000 claims description 5
- 108010050904 Interferons Proteins 0.000 claims description 5
- 229940079322 interferon Drugs 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 4
- 239000002212 purine nucleoside Substances 0.000 claims description 4
- CRWLATSHAHNVOV-XDTPYFJJSA-N (2r,3s,4r)-2-(hydroxymethyl)-5-(7h-purin-2-yl)oxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)OC1C1=NC=C(NC=N2)C2=N1 CRWLATSHAHNVOV-XDTPYFJJSA-N 0.000 claims description 2
- LRSASMSXMSNRBT-UHFFFAOYSA-N 5-methylcytosine Chemical group CC1=CNC(=O)N=C1N LRSASMSXMSNRBT-UHFFFAOYSA-N 0.000 claims description 2
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical group NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims description 2
- 229960004413 flucytosine Drugs 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 229940121759 Helicase inhibitor Drugs 0.000 claims 2
- 229940123066 Polymerase inhibitor Drugs 0.000 claims 2
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract description 5
- 235000021317 phosphate Nutrition 0.000 description 187
- 239000002585 base Substances 0.000 description 170
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 112
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 106
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 78
- 125000003118 aryl group Chemical group 0.000 description 61
- 150000002431 hydrogen Chemical group 0.000 description 61
- 229920002554 vinyl polymer Polymers 0.000 description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 56
- 125000001424 substituent group Chemical group 0.000 description 56
- 150000002632 lipids Chemical class 0.000 description 55
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 54
- 235000014633 carbohydrates Nutrition 0.000 description 54
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 54
- 235000012000 cholesterol Nutrition 0.000 description 53
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 52
- 150000003904 phospholipids Chemical class 0.000 description 52
- 150000001413 amino acids Chemical class 0.000 description 51
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 51
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 50
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 50
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 50
- 229910052794 bromium Inorganic materials 0.000 description 50
- 239000000460 chlorine Substances 0.000 description 50
- 229910052801 chlorine Inorganic materials 0.000 description 50
- 229910003204 NH2 Inorganic materials 0.000 description 49
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 49
- 229910052760 oxygen Inorganic materials 0.000 description 35
- 125000003835 nucleoside group Chemical group 0.000 description 33
- 235000000346 sugar Nutrition 0.000 description 33
- 229910052717 sulfur Inorganic materials 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 31
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 30
- DEMJYWYZJFNNNB-UHFFFAOYSA-N OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O Chemical compound OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O DEMJYWYZJFNNNB-UHFFFAOYSA-N 0.000 description 28
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 26
- 230000009467 reduction Effects 0.000 description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 25
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 25
- 125000006239 protecting group Chemical group 0.000 description 25
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 24
- 239000003112 inhibitor Substances 0.000 description 24
- 229910052740 iodine Inorganic materials 0.000 description 24
- 239000011630 iodine Substances 0.000 description 24
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 21
- 125000004093 cyano group Chemical group *C#N 0.000 description 21
- 239000002342 ribonucleoside Substances 0.000 description 21
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Natural products C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
- 230000000840 anti-viral effect Effects 0.000 description 18
- 125000003729 nucleotide group Chemical group 0.000 description 18
- QVLTXCYWHPZMCA-UHFFFAOYSA-N po4-po4 Chemical compound OP(O)(O)=O.OP(O)(O)=O QVLTXCYWHPZMCA-UHFFFAOYSA-N 0.000 description 18
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 14
- 239000002773 nucleotide Substances 0.000 description 14
- WYVPBFVWZCTMPP-UHFFFAOYSA-N OP(O)(=O)OP(=O)(O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)OP(=O)(O)O Chemical compound OP(O)(=O)OP(=O)(O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)OP(=O)(O)O WYVPBFVWZCTMPP-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 12
- CSSIWXFUZVBFND-UHFFFAOYSA-N OP(O)(=O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)O Chemical compound OP(O)(=O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)O CSSIWXFUZVBFND-UHFFFAOYSA-N 0.000 description 12
- 238000010511 deprotection reaction Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 241000700605 Viruses Species 0.000 description 11
- 238000003556 assay Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 108091092724 Noncoding DNA Proteins 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000003443 antiviral agent Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 229960002949 fluorouracil Drugs 0.000 description 8
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 8
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 238000011160 research Methods 0.000 description 8
- 241000710780 Bovine viral diarrhea virus 1 Species 0.000 description 7
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 7
- 229960001456 adenosine triphosphate Drugs 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 6
- LFGGWVMUILESJS-UHFFFAOYSA-N 1,7-dihydropurin-6-one phosphono dihydrogen phosphate Chemical compound OP(O)(=O)OP(=O)(O)O.N1C=NC=2N=CNC2C1=O LFGGWVMUILESJS-UHFFFAOYSA-N 0.000 description 6
- WKMPTBDYDNUJLF-UHFFFAOYSA-N 2-fluoroadenine Chemical compound NC1=NC(F)=NC2=C1N=CN2 WKMPTBDYDNUJLF-UHFFFAOYSA-N 0.000 description 6
- RDMGMZAMWLSHNS-UHFFFAOYSA-N 3,7-dihydropurin-6-one;phosphoric acid Chemical compound OP(O)(O)=O.O=C1NC=NC2=C1NC=N2 RDMGMZAMWLSHNS-UHFFFAOYSA-N 0.000 description 6
- YJQYHFMKGAVKDP-UHFFFAOYSA-N 3-butanoyl-1,8-dihydroxy-2-methylphenanthrene-9,10-dione Chemical compound C12=CC=CC(O)=C2C(=O)C(=O)C2=C1C=C(C(=O)CCC)C(C)=C2O YJQYHFMKGAVKDP-UHFFFAOYSA-N 0.000 description 6
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
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- MRZDHXLJHIMNOR-UHFFFAOYSA-N 8-fluoro-7h-purin-6-amine Chemical compound NC1=NC=NC2=C1NC(F)=N2 MRZDHXLJHIMNOR-UHFFFAOYSA-N 0.000 description 5
- 206010012310 Dengue fever Diseases 0.000 description 5
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- 150000002596 lactones Chemical class 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- HXERRKOZCLQLFP-UHFFFAOYSA-N 1,7-dihydropurin-6-one diphosphono hydrogen phosphate Chemical compound OP(O)(=O)OP(=O)(O)OP(=O)(O)O.N1C=NC=2N=CNC2C1=O HXERRKOZCLQLFP-UHFFFAOYSA-N 0.000 description 4
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Applications Claiming Priority (2)
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|---|---|---|---|
| US20767400P | 2000-05-26 | 2000-05-26 | |
| US28327601P | 2001-04-11 | 2001-04-11 |
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| NZ536570A true NZ536570A (en) | 2006-08-31 |
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- 2001-05-23 AU AU2001272923A patent/AU2001272923A1/en not_active Abandoned
- 2001-05-23 AP APAP/P/2002/002705A patent/AP1727A/en active
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