NO326135B1 - Stereoselektiv metode for fremstilling av nukleosider - Google Patents

Stereoselektiv metode for fremstilling av nukleosider Download PDF

Info

Publication number: NO326135B1
Authority: NO; Norway
Prior art keywords: alkyl; formula; optionally substituted; group; bromine
Prior art date: 2001-06-15

Application number

NO20035556A

Other languages

English (en)

Norwegian (no)

Other versions

NO20035556D0 (no

Inventor

Qing Yu

Original Assignee

Shire Canada Inc

Priority date (The priority date 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 date listed.)

2001-06-15

Filing date

2003-12-12

Publication date

2008-10-06

2003-12-12 Application filed by Shire Canada Inc filed Critical Shire Canada Inc

2003-12-12 Publication of NO20035556D0 publication Critical patent/NO20035556D0/no

2008-10-06 Publication of NO326135B1 publication Critical patent/NO326135B1/no

Links

238000000034 method Methods 0.000 title claims description 48
239000002777 nucleoside Substances 0.000 title claims description 25
125000003835 nucleoside group Chemical group 0.000 title claims description 7
230000000707 stereoselective effect Effects 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title description 2
239000000460 chlorine Chemical group 0.000 claims description 49
125000003118 aryl group Chemical group 0.000 claims description 44
229910052794 bromium Inorganic materials 0.000 claims description 44
229910052801 chlorine Inorganic materials 0.000 claims description 44
125000000217 alkyl group Chemical group 0.000 claims description 43
238000005859 coupling reaction Methods 0.000 claims description 42
230000008878 coupling Effects 0.000 claims description 39
238000010168 coupling process Methods 0.000 claims description 39
239000002904 solvent Substances 0.000 claims description 39
-1 C1-ioacyl Chemical group 0.000 claims description 38
229910052731 fluorine Inorganic materials 0.000 claims description 37
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 36
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 36
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 36
238000010511 deprotection reaction Methods 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 35
150000002367 halogens Chemical group 0.000 claims description 34
229910052740 iodine Inorganic materials 0.000 claims description 30
239000011737 fluorine Substances 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 28
125000001153 fluoro group Chemical group F* 0.000 claims description 26
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 22
239000011630 iodine Substances 0.000 claims description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 19
150000003512 tertiary amines Chemical class 0.000 claims description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 16
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 16
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 15
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 14
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 14
239000001301 oxygen Chemical group 0.000 claims description 14
125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 13
239000002841 Lewis acid Substances 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
150000007517 lewis acids Chemical class 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 12
125000004104 aryloxy group Chemical group 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
230000003197 catalytic effect Effects 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
229940127073 nucleoside analogue Drugs 0.000 claims description 10
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 claims description 9
GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 9
229910052717 sulfur Chemical group 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 7
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
229940104302 cytosine Drugs 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 7
125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
239000000908 ammonium hydroxide Substances 0.000 claims description 6
229910052802 copper Inorganic materials 0.000 claims description 6
238000002425 crystallisation Methods 0.000 claims description 6
230000008025 crystallization Effects 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 claims description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 5
DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
150000003833 nucleoside derivatives Chemical class 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
239000011593 sulfur Chemical group 0.000 claims description 5
229940113082 thymine Drugs 0.000 claims description 5
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 5
229940035893 uracil Drugs 0.000 claims description 5
229910052725 zinc Inorganic materials 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 3
MGAXHFMCFLLMNG-UHFFFAOYSA-N 1h-pyrimidine-6-thione Chemical compound SC1=CC=NC=N1 MGAXHFMCFLLMNG-UHFFFAOYSA-N 0.000 claims description 3
150000005696 4-halopyrimidines Chemical class 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000005864 Sulphur Substances 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
150000001413 amino acids Chemical class 0.000 claims description 3
125000005110 aryl thio group Chemical group 0.000 claims description 3
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
229910052793 cadmium Inorganic materials 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
229910052737 gold Inorganic materials 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 claims description 3
229910052709 silver Inorganic materials 0.000 claims description 3
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 claims description 3
125000005389 trialkylsiloxy group Chemical group 0.000 claims description 3
WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical group I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000001340 2-chloroethyl group Chemical class [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000004965 chloroalkyl group Chemical group 0.000 claims description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 claims description 2
ZDHWTWWXCXEGIC-UHFFFAOYSA-N 2-ethenylpyrimidine Chemical compound C=CC1=NC=CC=N1 ZDHWTWWXCXEGIC-UHFFFAOYSA-N 0.000 claims 1
UXIQHYCHEPUAGK-UHFFFAOYSA-N bromo(trimethyl)silane;trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)Br.C[Si](C)(C)OS(=O)(=O)C(F)(F)F UXIQHYCHEPUAGK-UHFFFAOYSA-N 0.000 claims 1
230000000737 periodic effect Effects 0.000 claims 1
NZAMMJKYTYHSHN-UHFFFAOYSA-N trimethyl-[(2-methyl-1,3-oxathiolan-5-yl)methyl]azanium Chemical compound CC1OC(C[N+](C)(C)C)CS1 NZAMMJKYTYHSHN-UHFFFAOYSA-N 0.000 claims 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000012351 deprotecting agent Substances 0.000 description 11
239000000047 product Substances 0.000 description 11
150000003462 sulfoxides Chemical class 0.000 description 11
239000010949 copper Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 5
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 4
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 4
239000013067 intermediate product Substances 0.000 description 4
WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
230000000840 anti-viral effect Effects 0.000 description 3
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000002346 iodo group Chemical group I* 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
LSOHGQXOSJAKNH-UHFFFAOYSA-N (3-oxo-1,3-oxathiolan-2-yl)methyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1OCCS1=O LSOHGQXOSJAKNH-UHFFFAOYSA-N 0.000 description 2
SVXNJCYYMRMXNM-UHFFFAOYSA-N 5-amino-2h-1,2,4-triazin-3-one Chemical compound NC=1C=NNC(=O)N=1 SVXNJCYYMRMXNM-UHFFFAOYSA-N 0.000 description 2
KSPDSMOWMQFPBL-UHFFFAOYSA-N 5-fluoropyrimidine Chemical compound FC1=CN=CN=C1 KSPDSMOWMQFPBL-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
LJJVEZISMNEQRE-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] trifluoromethanesulfonate;[dimethyl-(trimethylsilylamino)silyl]methane Chemical compound C[Si](C)(C)N[Si](C)(C)C.CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F LJJVEZISMNEQRE-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002718 pyrimidine nucleoside Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
229940001584 sodium metabisulfite Drugs 0.000 description 2
235000010262 sodium metabisulphite Nutrition 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-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
PCXPPEVXIKTQGP-UHFFFAOYSA-N 1,3-oxathiolan-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1OCCS1 PCXPPEVXIKTQGP-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
MFEFTTYGMZOIKO-UHFFFAOYSA-N 5-azacytosine Chemical compound NC1=NC=NC(=O)N1 MFEFTTYGMZOIKO-UHFFFAOYSA-N 0.000 description 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
HJBWJAPEBGSQPR-UHFFFAOYSA-N DMCA Natural products COC1=CC=C(C=CC(O)=O)C=C1OC HJBWJAPEBGSQPR-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000725303 Human immunodeficiency virus Species 0.000 description 1
241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
150000005694 halopyrimidines Chemical class 0.000 description 1
208000002672 hepatitis B Diseases 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010410 layer Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000010076 replication Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011701 zinc Substances 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Virology (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Saccharide Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

NO20035556A 2001-06-15 2003-12-12 Stereoselektiv metode for fremstilling av nukleosider NO326135B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US29807901P	2001-06-15	2001-06-15
PCT/CA2002/000899 WO2002102796A1 (en)	2001-06-15	2002-06-14	Stereoselective method for the preparation of nucleoside analogues

Publications (2)

Publication Number	Publication Date
NO20035556D0 NO20035556D0 (no)	2003-12-12
NO326135B1 true NO326135B1 (no)	2008-10-06

Family

ID=23148927

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20035556A NO326135B1 (no)	2001-06-15	2003-12-12	Stereoselektiv metode for fremstilling av nukleosider

Country Status (29)

Country	Link
US (2)	US7109334B2 (ko)
EP (2)	EP1632490B1 (ko)
JP (1)	JP4542776B2 (ko)
KR (1)	KR100832617B1 (ko)
CN (1)	CN1297553C (ko)
AP (1)	AP1559A (ko)
AT (2)	ATE313542T1 (ko)
AU (2)	AU2002344862C1 (ko)
BR (2)	BRPI0210444B1 (ko)
CA (1)	CA2449338C (ko)
CO (1)	CO5550497A2 (ko)
CY (1)	CY1107805T1 (ko)
DE (2)	DE60208202T2 (ko)
DK (2)	DK1632490T3 (ko)
EA (1)	EA006372B1 (ko)
ES (2)	ES2254695T3 (ko)
HK (1)	HK1070652A1 (ko)
HR (1)	HRP20031021B1 (ko)
IL (2)	IL159139A0 (ko)
MX (1)	MXPA03011627A (ko)
NO (1)	NO326135B1 (ko)
NZ (1)	NZ529906A (ko)
OA (1)	OA12628A (ko)
PL (2)	PL215267B1 (ko)
PT (1)	PT1632490E (ko)
RS (1)	RS50868B (ko)
SI (2)	SI1406896T1 (ko)
WO (1)	WO2002102796A1 (ko)
ZA (1)	ZA200309307B (ko)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7501514B1 (en)	2003-10-15	2009-03-10	Shire Biochem, Inc.	Enantiomeric resolution of 2-substituted 4-substituted 1,3-oxathiolanes nucleosides
JP4653966B2 (ja) *	2004-04-19	2011-03-16	ダイセル化学工業株式会社	２−ベンゾイルオキシアセトアルデヒド誘導体の製造法
IN2015DN02599A (ko) *	2007-09-28	2015-09-18	Avexa Ltd
US20130165350A1 (en) *	2011-12-22	2013-06-27	Affymetrix, Inc.	Surface linkers for array synthesis

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR840001591A (ko) *	1981-09-29	1984-05-07	구라바야시 이꾸시로	당케탈류의 제조방법
AU8864191A (en) *	1990-11-13	1992-06-11	Biochem Pharma Inc.	Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties
US5587480A (en) *	1990-11-13	1996-12-24	Biochem Pharma, Inc.	Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties
US5532349A (en) *	1993-07-20	1996-07-02	Mitsui Toatsu Chemicals, Inc.	Process for producing 1-(2'-deoxy-β-D-erythro-pentofuranosyl)-5-trifluoromethyluracil derivatives
CA2714085C (en) *	1998-08-12	2013-02-05	Emory University	Method of manufacture of 1,3-oxathiolane nucleosides

2002
- 2002-06-14 AP APAP/P/2003/002948A patent/AP1559A/en active
- 2002-06-14 AU AU2002344862A patent/AU2002344862C1/en not_active Ceased
- 2002-06-14 EP EP05017130A patent/EP1632490B1/en not_active Expired - Lifetime
- 2002-06-14 EA EA200400042A patent/EA006372B1/ru not_active IP Right Cessation
- 2002-06-14 BR BRPI0210444-0A patent/BRPI0210444B1/pt unknown
- 2002-06-14 IL IL15913902A patent/IL159139A0/xx unknown
- 2002-06-14 SI SI200230273T patent/SI1406896T1/sl unknown
- 2002-06-14 DE DE60208202T patent/DE60208202T2/de not_active Expired - Lifetime
- 2002-06-14 NZ NZ529906A patent/NZ529906A/xx not_active IP Right Cessation
- 2002-06-14 CA CA2449338A patent/CA2449338C/en not_active Expired - Fee Related
- 2002-06-14 JP JP2003506269A patent/JP4542776B2/ja not_active Expired - Fee Related
- 2002-06-14 US US10/170,418 patent/US7109334B2/en not_active Expired - Fee Related
- 2002-06-14 ES ES02742572T patent/ES2254695T3/es not_active Expired - Lifetime
- 2002-06-14 CN CNB028159624A patent/CN1297553C/zh not_active Expired - Fee Related
- 2002-06-14 PL PL366907A patent/PL215267B1/pl unknown
- 2002-06-14 SI SI200230631T patent/SI1632490T1/sl unknown
- 2002-06-14 WO PCT/CA2002/000899 patent/WO2002102796A1/en active IP Right Grant
- 2002-06-14 MX MXPA03011627A patent/MXPA03011627A/es active IP Right Grant
- 2002-06-14 KR KR1020037016301A patent/KR100832617B1/ko not_active IP Right Cessation
- 2002-06-14 AT AT02742572T patent/ATE313542T1/de active
- 2002-06-14 DK DK05017130T patent/DK1632490T3/da active
- 2002-06-14 RS YUP-975/03A patent/RS50868B/sr unknown
- 2002-06-14 PT PT05017130T patent/PT1632490E/pt unknown
- 2002-06-14 ES ES05017130T patent/ES2293445T3/es not_active Expired - Lifetime
- 2002-06-14 EP EP02742572A patent/EP1406896B8/en not_active Expired - Lifetime
- 2002-06-14 AT AT05017130T patent/ATE370945T1/de active
- 2002-06-14 DK DK02742572T patent/DK1406896T3/da active
- 2002-06-14 OA OA1200300329A patent/OA12628A/en unknown
- 2002-06-14 DE DE60222031T patent/DE60222031T2/de not_active Expired - Lifetime
- 2002-06-14 BR BR0210444-0A patent/BR0210444A/pt not_active IP Right Cessation
- 2002-06-14 PL PL401835A patent/PL218777B1/pl unknown
2003
- 2003-11-28 ZA ZA2003/09307A patent/ZA200309307B/en unknown
- 2003-12-01 IL IL159139A patent/IL159139A/en not_active IP Right Cessation
- 2003-12-09 HR HR20031021A patent/HRP20031021B1/xx not_active IP Right Cessation
- 2003-12-12 NO NO20035556A patent/NO326135B1/no not_active IP Right Cessation
2004
- 2004-01-14 CO CO04002061A patent/CO5550497A2/es active IP Right Grant
2005
- 2005-04-18 HK HK05103299A patent/HK1070652A1/xx not_active IP Right Cessation
2006
- 2006-04-07 US US11/399,502 patent/US7230100B2/en not_active Expired - Fee Related
2007
- 2007-11-15 CY CY20071101481T patent/CY1107805T1/el unknown
2008
- 2008-08-01 AU AU2008203443A patent/AU2008203443B2/en not_active Ceased

Also Published As

Publication number	Publication date
WO2002102796A1 (en)	2002-12-27
EP1632490A1 (en)	2006-03-08
US7109334B2 (en)	2006-09-19
EA006372B1 (ru)	2005-12-29
RS50868B (sr)	2010-08-31
ATE313542T1 (de)	2006-01-15
ES2293445T3 (es)	2008-03-16
HRP20031021A2 (en)	2004-06-30
JP4542776B2 (ja)	2010-09-15
US7230100B2 (en)	2007-06-12
HRP20031021B1 (en)	2007-09-30
EP1406896A1 (en)	2004-04-14
CA2449338C (en)	2012-02-07
IL159139A (en)	2010-04-15
PL218777B1 (pl)	2015-01-30
DK1632490T3 (da)	2008-01-28
AU2008203443B2 (en)	2011-06-16
YU97503A (sh)	2006-05-25
AU2002344862C1 (en)	2009-02-19
AU2008203443A1 (en)	2008-08-21
KR20040017233A (ko)	2004-02-26
EP1632490B1 (en)	2007-08-22
ES2254695T3 (es)	2006-06-16
ATE370945T1 (de)	2007-09-15
MXPA03011627A (es)	2005-03-07
CO5550497A2 (es)	2005-08-31
HK1070652A1 (en)	2005-06-24
EP1406896B8 (en)	2006-11-15
KR100832617B1 (ko)	2008-05-27
SI1632490T1 (sl)	2008-02-29
PT1632490E (pt)	2007-11-07
OA12628A (en)	2006-06-13
CA2449338A1 (en)	2002-12-27
NO20035556D0 (no)	2003-12-12
DE60208202T2 (de)	2006-08-17
DE60222031D1 (de)	2007-10-04
ZA200309307B (en)	2005-02-23
JP2004535428A (ja)	2004-11-25
IL159139A0 (en)	2004-06-01
DE60208202D1 (de)	2006-01-26
CY1107805T1 (el)	2013-06-19
PL401835A1 (pl)	2013-02-18
DE60222031T2 (de)	2008-05-21
SI1406896T1 (sl)	2006-04-30
WO2002102796A8 (en)	2003-09-18
BRPI0210444B1 (pt)	2017-06-20
NZ529906A (en)	2006-03-31
CN1297553C (zh)	2007-01-31
US20030135048A1 (en)	2003-07-17
AP1559A (en)	2006-01-24
AU2002344862B2 (en)	2008-05-01
EA200400042A1 (ru)	2004-06-24
EP1406896B1 (en)	2005-12-21
DK1406896T3 (da)	2006-05-08
BR0210444A (pt)	2004-08-17
PL215267B1 (pl)	2013-11-29
PL366907A1 (en)	2005-02-07
CN1543463A (zh)	2004-11-03
US20060183899A1 (en)	2006-08-17

Legal Events

Date	Code	Title	Description
2018-01-22	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US6215004B1 (en)	2001-04-10	Method of manufacture of 1,3-oxathiolane nucleosides
US20110257397A1 (en)	2011-10-20	Process and methods for the preparation of optically active cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-oxathiolane or pharmaceutically acceptable salts thereof
NO326135B1 (no)	2008-10-06	Stereoselektiv metode for fremstilling av nukleosider
CA2599825C (en)	2012-06-19	Process and methods for the preparation of optically active cis-2-hydroxymethyl-4-(cytosin-1'-yl)-1,3-oxathiolane or pharmaceutically acceptable salts thereof
AU2008331166B2 (en)	2013-10-10	Process for the preparation of substituted 1,3-oxathiolanes
AU2002344862A1 (en)	2003-05-15	Stereoselective method for the preparation of nucleoside analogues
WO2009069012A1 (en)	2009-06-04	Process and intermediates for the preparation of substituted 1, 3-oxathiolanes, especially lamivudine
CA2736163C (en)	2016-08-02	Enantiomeric resolution of 2,4-disubstituted 1,3-oxathiolane nucleosides
CA2700653A1 (en)	2009-04-02	A process for chiral resolution of 2-substituted 4-substituted 1,3-oxathiolanes