AP879A - Method and compositions for the synthesis of dioxolane nucleosides with b-configuration. - Google Patents
Method and compositions for the synthesis of dioxolane nucleosides with b-configuration. Download PDFInfo
- Publication number
- AP879A AP879A APAP/P/1998/001252A AP9801252A AP879A AP 879 A AP879 A AP 879A AP 9801252 A AP9801252 A AP 9801252A AP 879 A AP879 A AP 879A
- Authority
- AP
- ARIPO
- Prior art keywords
- group
- hydrogen
- formula
- process according
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 239000002777 nucleoside Substances 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 title abstract description 25
- 230000015572 biosynthetic process Effects 0.000 title abstract description 12
- 238000003786 synthesis reaction Methods 0.000 title abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 22
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 20
- -1 cyano, carboxy Chemical group 0.000 claims description 19
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 230000001279 glycosylating effect Effects 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000002346 iodo group Chemical group I* 0.000 claims description 12
- 239000002841 Lewis acid Substances 0.000 claims description 11
- 150000007517 lewis acids Chemical class 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 claims description 10
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 235000000346 sugar Nutrition 0.000 abstract description 15
- 229940127073 nucleoside analogue Drugs 0.000 abstract description 13
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract description 6
- 230000000707 stereoselective effect Effects 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 125000003835 nucleoside group Chemical group 0.000 description 12
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 238000006206 glycosylation reaction Methods 0.000 description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 6
- 150000003833 nucleoside derivatives Chemical class 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 229960001866 silicon dioxide Drugs 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 229940104302 cytosine Drugs 0.000 description 5
- 230000013595 glycosylation Effects 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910003445 palladium oxide Inorganic materials 0.000 description 3
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 230000006340 racemization Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 3
- WEMMEBUBCZJOBG-UHFFFAOYSA-N 1,3-dioxolan-2-yl acetate Chemical compound CC(=O)OC1OCCO1 WEMMEBUBCZJOBG-UHFFFAOYSA-N 0.000 description 2
- LLKFNPUXQZHIAE-UHFFFAOYSA-N 5-(3-aminopropyl)-8-bromo-3-methyl-2h-pyrazolo[4,3-c]quinolin-4-one Chemical compound O=C1N(CCCN)C2=CC=C(Br)C=C2C2=C1C(C)=NN2 LLKFNPUXQZHIAE-UHFFFAOYSA-N 0.000 description 2
- PEHVGBZKEYRQSX-UHFFFAOYSA-N 7-deaza-adenine Chemical compound NC1=NC=NC2=C1C=CN2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- IJCKBIINTQEGLY-UHFFFAOYSA-N N(4)-acetylcytosine Chemical compound CC(=O)NC1=CC=NC(=O)N1 IJCKBIINTQEGLY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002253 acid Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical class N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000006392 deoxygenation reaction Methods 0.000 description 2
- AIHCVGFMFDEUMO-UHFFFAOYSA-N diiodosilane Chemical compound I[SiH2]I AIHCVGFMFDEUMO-UHFFFAOYSA-N 0.000 description 2
- RNRZLEZABHZRSX-UHFFFAOYSA-N diiodosilicon Chemical compound I[Si]I RNRZLEZABHZRSX-UHFFFAOYSA-N 0.000 description 2
- 150000004862 dioxolanes Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- QVYCPSLFHSYJLC-UHFFFAOYSA-N n-(5-fluoro-2-oxo-1h-pyrimidin-6-yl)acetamide Chemical compound CC(=O)NC=1NC(=O)N=CC=1F QVYCPSLFHSYJLC-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- AENKMCZLEKTGRU-INIZCTEOSA-N (4s)-4,5-dihydroxy-2,2-diphenylpentanethial Chemical compound C=1C=CC=CC=1C(C=S)(C[C@H](O)CO)C1=CC=CC=C1 AENKMCZLEKTGRU-INIZCTEOSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- 125000006091 1,3-dioxolane group Chemical class 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- FNHOXBWIFBRJKI-UHFFFAOYSA-N 2-sulfonyl-1,3-dihydroimidazole Chemical class O=S(=O)=C1NC=CN1 FNHOXBWIFBRJKI-UHFFFAOYSA-N 0.000 description 1
- VNDWQCSOSCCWIP-UHFFFAOYSA-N 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one Chemical compound C1=2C=CNC(=O)C=2C2=CC(F)=CC=C2C2=C1NC(C(C)(C)C)=N2 VNDWQCSOSCCWIP-UHFFFAOYSA-N 0.000 description 1
- GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical class N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 description 1
- PANPMNGUWWTDHB-PHDIDXHHSA-N 4-amino-5-fluoro-1-[(2r,4r)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1S[C@H](CO)OC1 PANPMNGUWWTDHB-PHDIDXHHSA-N 0.000 description 1
- YNWUIBSEOAWSHW-HIQWKFPQSA-N 5-[(e)-2-bromoethenyl]-1-[(2s,4s)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]pyrimidine-2,4-dione Chemical class O1[C@@H](CO)OC[C@H]1N1C(=O)NC(=O)C(\C=C\Br)=C1 YNWUIBSEOAWSHW-HIQWKFPQSA-N 0.000 description 1
- TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 description 1
- ASUCSHXLTWZYBA-UMMCILCDSA-N 8-Bromoguanosine Chemical compound C1=2NC(N)=NC(=O)C=2N=C(Br)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O ASUCSHXLTWZYBA-UMMCILCDSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical class OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical class 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 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 239000002211 L-ascorbic acid Substances 0.000 description 1
- 235000000069 L-ascorbic acid Nutrition 0.000 description 1
- NIDVTARKFBZMOT-PEBGCTIMSA-N N(4)-acetylcytidine Chemical compound O=C1N=C(NC(=O)C)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NIDVTARKFBZMOT-PEBGCTIMSA-N 0.000 description 1
- UGJBHEZMOKVTIM-UHFFFAOYSA-N N-formylglycine Chemical compound OC(=O)CNC=O UGJBHEZMOKVTIM-UHFFFAOYSA-N 0.000 description 1
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical class IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- RYMCFYKJDVMSIR-RNFRBKRXSA-N apricitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1S[C@H](CO)OC1 RYMCFYKJDVMSIR-RNFRBKRXSA-N 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229960002656 didanosine Drugs 0.000 description 1
- 235000010300 dimethyl dicarbonate Nutrition 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000007337 electrophilic addition reaction Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 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
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- LUCZRURMVMAGFM-AAQQEJRNSA-N n-[1-[(2s,3r,4s,5r)-2-fluoro-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide Chemical compound O=C1N=C(NC(=O)C)C=CN1[C@@]1(F)[C@H](O)[C@H](O)[C@@H](CO)O1 LUCZRURMVMAGFM-AAQQEJRNSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005880 oxathiolanyl group Chemical group 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 239000002718 pyrimidine nucleoside Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9525606.1A GB9525606D0 (en) | 1995-12-14 | 1995-12-14 | Method and compositions for the synthesis of dioxolane nucleosides with - configuration |
| PCT/CA1996/000845 WO1997021706A1 (en) | 1995-12-14 | 1996-12-13 | METHOD AND COMPOSITIONS FOR THE SYNTHESIS OF DIOXOLANE NUCLEOSIDES WITH β-CONFIGURATION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9801252A0 AP9801252A0 (en) | 1998-06-30 |
| AP879A true AP879A (en) | 2000-10-02 |
Family
ID=10785435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1998/001252A AP879A (en) | 1995-12-14 | 1996-12-13 | Method and compositions for the synthesis of dioxolane nucleosides with b-configuration. |
Country Status (27)
| Country | Link |
|---|---|
| US (4) | US5922867A (enExample) |
| EP (1) | EP0970074B1 (enExample) |
| JP (1) | JP3229990B2 (enExample) |
| KR (1) | KR100406159B1 (enExample) |
| CN (1) | CN1080263C (enExample) |
| AP (1) | AP879A (enExample) |
| AT (1) | ATE214699T1 (enExample) |
| AU (1) | AU706328B2 (enExample) |
| BR (1) | BR9612351A (enExample) |
| CA (1) | CA2237730C (enExample) |
| DE (1) | DE69620042T2 (enExample) |
| DK (1) | DK0970074T3 (enExample) |
| EA (1) | EA000844B1 (enExample) |
| ES (1) | ES2172697T3 (enExample) |
| GB (1) | GB9525606D0 (enExample) |
| HU (1) | HU224076B1 (enExample) |
| IL (3) | IL124663A (enExample) |
| IN (1) | IN187349B (enExample) |
| MX (1) | MX9804701A (enExample) |
| NO (1) | NO309901B1 (enExample) |
| NZ (1) | NZ323855A (enExample) |
| OA (1) | OA11094A (enExample) |
| PL (1) | PL188447B1 (enExample) |
| PT (1) | PT970074E (enExample) |
| TW (1) | TW341574B (enExample) |
| WO (1) | WO1997021706A1 (enExample) |
| ZA (1) | ZA9610544B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001518899A (ja) | 1997-04-07 | 2001-10-16 | トライアングル ファーマシューティカルズ，インコーポレイティド | 他の抗ウイルス剤との組合せにおけるｍｋｃ−４４２の使用 |
| EP1535921A1 (en) | 1998-08-12 | 2005-06-01 | Gilead Sciences, Inc. | Method of manufacture of 1,3-oxathiolane nucleosides |
| US6979561B1 (en) * | 1998-10-09 | 2005-12-27 | Gilead Sciences, Inc. | Non-homogeneous systems for the resolution of enantiomeric mixtures |
| EA004767B1 (ru) * | 1998-12-23 | 2004-08-26 | Шайре Байокем Инк. | Аналоги нуклеозида (варианты) и их применение, комбинация и способ лечения вирусных инфекций, фармацевтическая композиция |
| JP2002538780A (ja) * | 1999-02-11 | 2002-11-19 | シェア バイオケム インコーポレーテッド | ヌクレオシド類似体の立体選択的合成 |
| DE60011637T2 (de) * | 1999-09-24 | 2004-11-11 | Shire Biochem Inc., Laval | Dioxolan nukleosidanalogen zur behandlung und vorbeugung von viralen infektionen |
| CA2389745C (en) * | 1999-11-04 | 2010-03-23 | Shire Biochem Inc. | Method for the treatment or prevention of flaviviridae viral infection using nucleoside analogues |
| US7038039B2 (en) * | 2000-02-10 | 2006-05-02 | Mitsui Chemicals, Inc. | Process for selectively producing 1-phosphorylated sugar derivative anomer and process for producing nucleoside |
| AU3144801A (en) * | 2000-02-11 | 2001-08-20 | Shire Biochem Inc. | Stereoselective synthesis of nucleoside analogues |
| WO2002051852A1 (fr) * | 2000-12-27 | 2002-07-04 | Mitsui Chemicals, Inc. | Procede de production d'un derive de saccharide non naturel |
| CA2867970A1 (en) * | 2001-03-01 | 2002-09-12 | Gilead Sciences, Inc. | Polymorphic and other crystalline forms of cis-ftc |
| AU2002329970A1 (en) * | 2001-09-04 | 2003-03-18 | Isis Pharmaceuticals, Inc. | Pyrrolo(2,3-d)pyrimidines for inhibiting rna-dependent rna viral polymerase |
| EP1441733A1 (en) * | 2001-11-02 | 2004-08-04 | Shire Biochem Inc. | Pharmaceutical compositions for the treatment of leukemia comprising dioxolane nucleosides analogs |
| CN100560073C (zh) * | 2001-12-14 | 2009-11-18 | 法玛塞特公司 | 用于治疗病毒感染的n4-酰基胞嘧啶核苷 |
| EP1467990B1 (en) * | 2002-01-25 | 2012-03-07 | Shire BioChem Inc. | Process for producing dioxolane nucleoside analogue precursors |
| IL166682A0 (en) | 2002-08-06 | 2006-01-15 | Pharmasset Ltd | Processes for preparing 1,3-dioxolane nucleosides |
| AU2003304716A1 (en) | 2002-10-15 | 2005-11-25 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| DE10335061B4 (de) | 2003-07-31 | 2005-11-17 | Wacker-Chemie Gmbh | Verfahren zur Herstellung von OH-geschützten [4-(2,6-damino-9H-purin-9-yl)-1,3-dioxolan-2-yl]methanol-Derivaten |
| KR101157468B1 (ko) * | 2004-02-03 | 2012-07-06 | 에모리 유니버시티 | 1,3-디옥솔란 뉴클레오시드 제조방법 |
| US7749531B2 (en) * | 2005-06-08 | 2010-07-06 | Indicator Systems International | Apparatus and method for detecting bacterial growth beneath a wound dressing |
| BRPI0813036A2 (pt) * | 2007-07-30 | 2017-10-24 | Rfs Pharma Llc | processo estereosseletivo para preparar derivados do nucleosídeo dioxolana de purina. |
| CN101862676B (zh) * | 2009-04-17 | 2012-01-25 | 中国石油化工股份有限公司 | 大孔径sba-15介孔材料-三氟甲磺酸铜复合催化剂、制备方法及应用 |
| CN103288806A (zh) * | 2013-07-02 | 2013-09-11 | 山东大学 | 一种曲沙他滨的合成方法 |
| WO2018022263A1 (en) | 2016-07-29 | 2018-02-01 | Exxonmobil Chemical Patents Inc. | Polymerization processes using high molecular weight polyhydric quenching agents |
| WO2019245444A1 (en) | 2018-06-21 | 2019-12-26 | Medivir Ab | Base-modified cytidine nucleotides for leukemia therapy |
| JP7337539B2 (ja) | 2018-06-21 | 2023-09-04 | メディヴィル・アクチエボラーグ | 白血病療法のための塩基修飾シチジンヌクレオチド |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992014729A1 (en) * | 1991-02-22 | 1992-09-03 | Emory University | Antiviral 1,3-dioxolane nucleosides and synthesis thereof |
| EP0577304A1 (en) * | 1992-06-22 | 1994-01-05 | Eli Lilly And Company | Stereoselective anion glycosylation process |
-
1995
- 1995-12-14 GB GBGB9525606.1A patent/GB9525606D0/en active Pending
-
1996
- 1996-12-13 WO PCT/CA1996/000845 patent/WO1997021706A1/en not_active Ceased
- 1996-12-13 IL IL12466396A patent/IL124663A/en not_active IP Right Cessation
- 1996-12-13 IN IN2810DE1996 patent/IN187349B/en unknown
- 1996-12-13 NZ NZ323855A patent/NZ323855A/xx unknown
- 1996-12-13 JP JP52157397A patent/JP3229990B2/ja not_active Expired - Lifetime
- 1996-12-13 US US08/849,722 patent/US5922867A/en not_active Expired - Lifetime
- 1996-12-13 AU AU10893/97A patent/AU706328B2/en not_active Expired
- 1996-12-13 PT PT96941539T patent/PT970074E/pt unknown
- 1996-12-13 AT AT96941539T patent/ATE214699T1/de not_active IP Right Cessation
- 1996-12-13 AP APAP/P/1998/001252A patent/AP879A/en active
- 1996-12-13 PL PL96327443A patent/PL188447B1/pl not_active IP Right Cessation
- 1996-12-13 ES ES96941539T patent/ES2172697T3/es not_active Expired - Lifetime
- 1996-12-13 CA CA002237730A patent/CA2237730C/en not_active Expired - Lifetime
- 1996-12-13 DK DK96941539T patent/DK0970074T3/da active
- 1996-12-13 TW TW085115392A patent/TW341574B/zh active
- 1996-12-13 DE DE69620042T patent/DE69620042T2/de not_active Expired - Lifetime
- 1996-12-13 EA EA199800555A patent/EA000844B1/ru not_active IP Right Cessation
- 1996-12-13 HU HU9901050A patent/HU224076B1/hu active IP Right Grant
- 1996-12-13 EP EP96941539A patent/EP0970074B1/en not_active Expired - Lifetime
- 1996-12-13 KR KR10-1998-0704473A patent/KR100406159B1/ko not_active Expired - Fee Related
- 1996-12-13 CN CN96199879A patent/CN1080263C/zh not_active Expired - Lifetime
- 1996-12-13 ZA ZA9610544A patent/ZA9610544B/xx unknown
- 1996-12-13 BR BR9612351A patent/BR9612351A/pt not_active Application Discontinuation
- 1996-12-13 IL IL14415596A patent/IL144155A/xx not_active IP Right Cessation
-
1998
- 1998-06-09 OA OA9800077A patent/OA11094A/en unknown
- 1998-06-11 MX MX9804701A patent/MX9804701A/es unknown
- 1998-06-12 NO NO982716A patent/NO309901B1/no unknown
-
1999
- 1999-02-17 US US09/251,431 patent/US6069250A/en not_active Expired - Lifetime
-
2001
- 2001-07-05 IL IL14415501A patent/IL144155A0/xx unknown
- 2001-11-16 US US09/987,845 patent/US20020058670A1/en not_active Abandoned
-
2002
- 2002-10-02 US US10/262,107 patent/US20030060476A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992014729A1 (en) * | 1991-02-22 | 1992-09-03 | Emory University | Antiviral 1,3-dioxolane nucleosides and synthesis thereof |
| EP0577304A1 (en) * | 1992-06-22 | 1994-01-05 | Eli Lilly And Company | Stereoselective anion glycosylation process |
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