KR100343481B1 - N4-아실-5'-데옥시-5-플루오로시티딘유도체의제조방법 - Google Patents
N4-아실-5'-데옥시-5-플루오로시티딘유도체의제조방법 Download PDFInfo
- Publication number
- KR100343481B1 KR100343481B1 KR1019930028167A KR930028167A KR100343481B1 KR 100343481 B1 KR100343481 B1 KR 100343481B1 KR 1019930028167 A KR1019930028167 A KR 1019930028167A KR 930028167 A KR930028167 A KR 930028167A KR 100343481 B1 KR100343481 B1 KR 100343481B1
- Authority
- KR
- South Korea
- Prior art keywords
- radical
- deoxy
- formula
- radicals
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229960004413 flucytosine Drugs 0.000 claims abstract description 25
- -1 amino radicals Chemical class 0.000 claims description 190
- 150000001875 compounds Chemical class 0.000 claims description 87
- 239000002904 solvent Substances 0.000 claims description 33
- 150000003254 radicals Chemical class 0.000 claims description 27
- 150000005840 aryl radicals Chemical class 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 abstract description 5
- 230000010933 acylation Effects 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 238000006243 chemical reaction Methods 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 38
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 34
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 239000002585 base Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- MPLJEMHLBLIUEN-UHFFFAOYSA-N n-(5-fluoro-2-oxo-1h-pyrimidin-6-yl)-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C(=CNC(=O)N=2)F)=C1 MPLJEMHLBLIUEN-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- YSNABXSEHNLERR-ZIYNGMLESA-N 5'-Deoxy-5-fluorocytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)N=C(N)C(F)=C1 YSNABXSEHNLERR-ZIYNGMLESA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 238000006884 silylation reaction Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- STRZQWQNZQMHQR-UAKXSSHOSA-N 5-fluorocytidine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 STRZQWQNZQMHQR-UAKXSSHOSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000005947 deacylation reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- OGOPVNZBIWLOIJ-UHFFFAOYSA-N 1-phenylethyl radical Chemical compound C[CH]C1=CC=CC=C1 OGOPVNZBIWLOIJ-UHFFFAOYSA-N 0.000 description 1
- UZGKAASZIMOAMU-UHFFFAOYSA-N 124177-85-1 Chemical compound NP(=O)=O UZGKAASZIMOAMU-UHFFFAOYSA-N 0.000 description 1
- GJWHXWMUGWZNTO-UHFFFAOYSA-N 2,2-dimethylpropane Chemical compound [CH2]C(C)(C)C GJWHXWMUGWZNTO-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 1
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JATVENGGZWYVAK-GGTFDOENSA-N C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C(NC2=O)(C(=O)C3=CC=C(C=C3)Cl)N)F)O)O Chemical compound C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C(NC2=O)(C(=O)C3=CC=C(C=C3)Cl)N)F)O)O JATVENGGZWYVAK-GGTFDOENSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- BOYVXXFJGPOZSN-UHFFFAOYSA-N OS(=O)(=O)C(F)(F)F.C[Si](C)(C)OS(=O)(=O)C(F)(F)F Chemical compound OS(=O)(=O)C(F)(F)F.C[Si](C)(C)OS(=O)(=O)C(F)(F)F BOYVXXFJGPOZSN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- BFKVXNPJXXJUGQ-UHFFFAOYSA-N [CH2]CCCC Chemical compound [CH2]CCCC BFKVXNPJXXJUGQ-UHFFFAOYSA-N 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- AQMHNCQZLQUNJI-UHFFFAOYSA-N [CH2]CCCCCC Chemical compound [CH2]CCCCCC AQMHNCQZLQUNJI-UHFFFAOYSA-N 0.000 description 1
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 description 1
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960001887 aminometradine Drugs 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- ZAEBLFKQMDEPDM-UHFFFAOYSA-N cyclobutyl radical Chemical compound [CH]1CCC1 ZAEBLFKQMDEPDM-UHFFFAOYSA-N 0.000 description 1
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical compound [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- DUUPDCPVCHSTFF-UHFFFAOYSA-N nonane Chemical compound [CH2]CCCCCCCC DUUPDCPVCHSTFF-UHFFFAOYSA-N 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- 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
- C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP92121539 | 1992-12-18 | ||
| JP92121539.8 | 1992-12-18 | ||
| EP92121539.8 | 1992-12-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR940014429A KR940014429A (ko) | 1994-07-18 |
| KR100343481B1 true KR100343481B1 (ko) | 2002-11-23 |
Family
ID=8210305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930028167A Expired - Lifetime KR100343481B1 (ko) | 1992-12-18 | 1993-12-17 | N4-아실-5'-데옥시-5-플루오로시티딘유도체의제조방법 |
Country Status (13)
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5476932A (en) * | 1994-08-26 | 1995-12-19 | Hoffmann-La Roche Inc. | Process for producing N4-acyl-5'-deoxy-5-fluorocytidine derivatives |
| NZ330360A (en) * | 1997-06-02 | 1999-03-29 | Hoffmann La Roche | 5'-deoxy-cytidine derivatives, their manufacture and use as antitumoral agents |
| EP0882734B1 (en) * | 1997-06-02 | 2009-08-26 | F. Hoffmann-La Roche Ag | 5'-Deoxy-cytidine derivatives |
| US6005098A (en) * | 1998-02-06 | 1999-12-21 | Hoffmann-La Roche Inc. | 5'deoxycytidine derivatives |
| KR100631754B1 (ko) * | 2000-08-09 | 2006-10-09 | 주식회사 코오롱 | Ｎ-알킬옥시카르보닐-5-플루오로사이토신 유도체 및 그의제조방법 |
| 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 |
| EP1589027A1 (en) * | 2003-01-17 | 2005-10-26 | Ajinomoto Co., Inc. | Processes for production of nucleosides |
| KR100851272B1 (ko) * | 2003-12-22 | 2008-08-08 | 에프. 호프만-라 로슈 아게 | 플루오로시티딘 유도체에 대한 방법 |
| CN100383128C (zh) * | 2004-02-23 | 2008-04-23 | 上海迪赛诺医药发展有限公司 | N4－氧羰基胞嘧啶衍生物及制备方法与应用 |
| US20050192433A1 (en) * | 2004-02-26 | 2005-09-01 | Mitsui Chemicals, Inc. | Metallic salt of N4-acylcytidine derivatives, and a method for producing N4-acylcytidine derivatives using the same |
| JP4627625B2 (ja) * | 2004-03-11 | 2011-02-09 | 三井化学株式会社 | Ｎ−アセチルシチジン類の製造方法 |
| WO2006040645A1 (en) * | 2004-10-11 | 2006-04-20 | Ranbaxy Laboratories Limited | N-(3,5-dichloropyridin-4-yl)-2,4,5-alkoxy and 2,3,4-alkoxy benzamide derivatives as pde-iv (phophodiesterase type-iv) inhibitors for the treatment of inflammatory diseases such as asthma |
| CN113952338A (zh) | 2005-02-03 | 2022-01-21 | 综合医院公司 | 治疗吉非替尼耐药性癌症的方法 |
| WO2006103187A2 (en) * | 2005-04-01 | 2006-10-05 | F. Hoffmann-La Roche Ag | Method for administration of capecitabine |
| RU2451524C2 (ru) | 2005-11-04 | 2012-05-27 | Вайет | Противоопухолевые комбинации с ингибиторами mtor, герцептином и/или hki-272 |
| US20080085310A1 (en) * | 2006-10-06 | 2008-04-10 | Maria Oksana Bachynsky | Capecitabine rapidly disintegrating tablets |
| JP2010524960A (ja) * | 2007-04-20 | 2010-07-22 | ドクター・レディーズ・ラボラトリーズ・リミテッド | カペシタビンを調製するためのプロセス |
| US8022216B2 (en) | 2007-10-17 | 2011-09-20 | Wyeth Llc | Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof |
| KR101013312B1 (ko) * | 2007-11-19 | 2011-02-09 | 한미홀딩스 주식회사 | 카페시타빈의 제조방법 및 이에 사용되는 β-아노머가강화된 트리알킬카보네이트 화합물의 제조방법 |
| AR064165A1 (es) * | 2007-12-06 | 2009-03-18 | Richmond Sa Com Ind Y Financie | Un procedimiento para la preparacion de capecitabina e intermediarios utilizables en dicho procedimiento |
| KR20090122955A (ko) * | 2008-01-03 | 2009-12-01 | 플러스 케미칼스, 에스.에이. | 카페시타빈의 제조 방법 |
| EP2562161A1 (en) | 2008-01-22 | 2013-02-27 | Dow AgroSciences LLC | 5-fluoro pyrimidine derivatives as fungicides |
| PL2310011T3 (pl) | 2008-06-17 | 2013-12-31 | Wyeth Llc | Kombinacje przeciwnowotworowe zawierające HKI-272 i vinorelbine |
| MX2011001318A (es) | 2008-08-04 | 2011-03-04 | Wyeth Llc | Combinaciones antineoplasicas de 4-anilino-3-cianoquinolinas y capecitabina. |
| WO2010061402A2 (en) * | 2008-11-25 | 2010-06-03 | Vishwanath Kannan | An improved process for the preparation of capecitabine |
| WO2010065586A2 (en) * | 2008-12-02 | 2010-06-10 | Dr. Reddy's Laboratories Ltd. | Preparation of capecitabine |
| CN101525362B (zh) * | 2009-01-15 | 2011-05-11 | 浙江诚意药业有限公司 | 5’-脱氧-2’,3’-二乙酰-5-氟胞苷的制备方法 |
| ES2941894T3 (es) | 2009-04-06 | 2023-05-26 | Wyeth Llc | Régimen de tratamiento que utiliza neratinib contra el cáncer de mama |
| KR20120037932A (ko) * | 2009-07-23 | 2012-04-20 | 시노팜 타이완 리미티드 | 플루오로시티딘 유도체를 제조하는 방법 |
| CN102190695B (zh) * | 2010-03-18 | 2013-12-18 | 齐鲁制药有限公司 | 5’-脱氧-2’，3’-二乙酰-5-氟胞苷的制备方法 |
| CN101830952A (zh) * | 2010-04-22 | 2010-09-15 | 上海柯林斯堡医药科技有限公司 | 2’,3’-o-二乙酰基-5’-脱氧-5-氟胞苷的制备方法 |
| CN101830953A (zh) * | 2010-05-26 | 2010-09-15 | 南京亚东启天药业有限公司 | 一种卡培他滨及其中间体的制备方法 |
| US20130178614A1 (en) * | 2011-10-25 | 2013-07-11 | Virginia Tech Intellectual Properties, Inc. | Regioselectively substituted cellulose esters and efficient methods of preparing them |
| TWI560195B (en) * | 2012-01-13 | 2016-12-01 | Pharmaessentia Corp | Novel synthesis of 5-deoxy-5'-fluorocytidine compounds |
| CN103570781B (zh) * | 2012-07-02 | 2016-01-13 | 国药一心制药有限公司 | 一种卡培他滨的工业化制备方法 |
| EP2883959A1 (en) | 2013-12-13 | 2015-06-17 | Plasmia Biotech, S.L. | Enzymatic production of cytosinic nucleoside analogues |
| CN103897006A (zh) * | 2013-12-18 | 2014-07-02 | 吉林修正药业新药开发有限公司 | 一种卡培他滨异构体的制备方法 |
| US10858349B2 (en) * | 2016-06-28 | 2020-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of cancer |
| US11584733B2 (en) | 2017-01-09 | 2023-02-21 | Shuttle Pharmaceuticals, Inc. | Selective histone deacetylase inhibitors for the treatment of human disease |
| CA3049435A1 (en) | 2017-01-09 | 2018-07-12 | Scott Grindrod | Selective histone deacetylase inhibitors for the treatment of human disease |
| US11407723B2 (en) | 2018-01-09 | 2022-08-09 | Shuttle Pharmaceuticals, Inc. | Selective histone deacetylase inhibitors for the treatment of human disease |
| AU2019313484A1 (en) * | 2018-08-03 | 2021-02-18 | Cellix Bio Private Limited | Compositions and methods for the treatment of cancer |
| CN109651467A (zh) * | 2019-01-15 | 2019-04-19 | 齐鲁天和惠世制药有限公司 | 一种卡培他滨杂质及其制备方法 |
| CN111100172B (zh) * | 2019-12-11 | 2023-03-17 | 中国科学院昆明植物研究所 | 一种胞嘧啶核苷衍生物及该衍生物制备卡培他滨药物的方法 |
| WO2022049462A1 (en) * | 2020-09-05 | 2022-03-10 | Cellix Bio Private Limited | Process for the preparation of derivatives of 5-fluoro pyrimidines used as anti cancer agents |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1327358C (en) * | 1987-11-17 | 1994-03-01 | Morio Fujiu | Fluoro cytidine derivatives |
| DE68922899T2 (de) * | 1988-12-07 | 1995-10-12 | Yamasa Shoyu Kk | Verbindungen von Pyrimidin 2'-Methylidin Nukleosiden. |
| JPH0576898A (ja) * | 1991-09-20 | 1993-03-30 | Hitachi Kiden Kogyo Ltd | スクリーン渣の破砕洗浄装置 |
| FR2684997A1 (fr) | 1991-12-12 | 1993-06-18 | Centre Nat Rech Scient | Derives de la 9-(beta-d-xylofurannosyl) adenine et de la 1-(beta-d-xylofurannosyl) cytosine, leur preparation et leur application en therapeutique. |
-
1993
- 1993-11-24 TW TW082109917A patent/TW254946B/zh not_active IP Right Cessation
- 1993-11-30 CA CA002110335A patent/CA2110335C/en not_active Expired - Lifetime
- 1993-12-03 DK DK93119528.3T patent/DK0602478T3/da active
- 1993-12-03 AT AT93119528T patent/ATE140923T1/de active
- 1993-12-03 DE DE69303879T patent/DE69303879T2/de not_active Expired - Lifetime
- 1993-12-03 EP EP93119528A patent/EP0602478B1/en not_active Expired - Lifetime
- 1993-12-03 ES ES93119528T patent/ES2093905T3/es not_active Expired - Lifetime
- 1993-12-16 RU RU93055875A patent/RU2131879C1/ru active
- 1993-12-16 JP JP34953593A patent/JP3530218B2/ja not_active Expired - Lifetime
- 1993-12-16 US US08/168,608 patent/US5453497A/en not_active Expired - Lifetime
- 1993-12-17 KR KR1019930028167A patent/KR100343481B1/ko not_active Expired - Lifetime
- 1993-12-17 CN CN93112894A patent/CN1035675C/zh not_active Expired - Lifetime
-
1999
- 1999-07-26 CY CY9900019A patent/CY2154B1/xx unknown
-
2004
- 2004-01-08 JP JP2004002807A patent/JP4202274B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0602478B1 (en) | 1996-07-31 |
| CA2110335C (en) | 2004-01-20 |
| JP2004123758A (ja) | 2004-04-22 |
| US5453497A (en) | 1995-09-26 |
| DE69303879T2 (de) | 1997-01-30 |
| CA2110335A1 (en) | 1994-06-19 |
| JP3530218B2 (ja) | 2004-05-24 |
| JPH07300492A (ja) | 1995-11-14 |
| CN1095070A (zh) | 1994-11-16 |
| CN1035675C (zh) | 1997-08-20 |
| ES2093905T3 (es) | 1997-01-01 |
| EP0602478A1 (en) | 1994-06-22 |
| CY2154B1 (en) | 2002-08-23 |
| ATE140923T1 (de) | 1996-08-15 |
| DE69303879D1 (de) | 1996-09-05 |
| JP4202274B2 (ja) | 2008-12-24 |
| KR940014429A (ko) | 1994-07-18 |
| DK0602478T3 (da) | 1996-09-30 |
| RU2131879C1 (ru) | 1999-06-20 |
| TW254946B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-08-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100343481B1 (ko) | N4-아실-5'-데옥시-5-플루오로시티딘유도체의제조방법 | |
| US6090932A (en) | Method of preparation of known and novel 2'-modified nucleosides by intramolecular nucleophilic displacement | |
| US5208327A (en) | Intermediates useful in a synthesis of 2-chloro-2'-deoxyadenosine | |
| US5521294A (en) | 2,2-difluoro-3-carbamoyl ribose sulfonate compounds and process for the preparation of beta nucleosides | |
| US4082911A (en) | Process for the preparation of nucleosides | |
| CA2085345C (en) | Pyrimidine nucleoside derivatives | |
| AU602909B2 (en) | Pyrimidine derivatives | |
| JPH06102655B2 (ja) | ジフルオロ抗ウイルス剤の中間体 | |
| EP0285884A2 (en) | Process to produce 2', 3'-Dideoxynucleosides | |
| US5459254A (en) | Process for preparing synthetic intermediates of 2-alkynyladenosines and 2-alkynyladenosines | |
| EP0222192A2 (en) | Nucleosides of 5-monofluoromethyluracil and 5-difluoromethyluracil | |
| EP0193903B1 (en) | Production of cytosine nucleosides | |
| Eger et al. | Steric fixation of bromovinyluracil: Synthesis of furo [2, 3‐d] pyrimidine nucleosides | |
| JPH075626B2 (ja) | ０▲上２▼，２′‐アンヒドロ‐１‐（β‐Ｄ‐アラビノフラノシル）チミンの製造方法 | |
| US4751293A (en) | Process for preparation of N6 -substituted 3',5'-cyclic adenosine monophosphate and salt thereof | |
| JPH05294964A (ja) | 炭素環式ヌクレオシドの製法及び中間体類 | |
| EP1554298A1 (en) | Process for the preparation of 9-beta-anomeric nucleoside analogs | |
| KR100247734B1 (ko) | 디-펜토푸라노오즈유도체및그의제조방법 | |
| Arita et al. | Enantioselective synthesis of new analogs of neplanocin A and their biological activity | |
| JP3165420B2 (ja) | Ｄ−ペントフラノース誘導体及びその製造法 | |
| US5621086A (en) | Sialic acid derivative and method of manufacturing it | |
| JPH07157496A (ja) | デオキシヌクレオシドの製造法 | |
| EP1654270B1 (en) | Process for preparing 2',3'-didehydro-2',3'-dideoxynucleosides and 2',3'-dideoxynucleosides | |
| JPH08119989A (ja) | ６−置換アミノプリン誘導体の新規な製法およびその中間体 | |
| JPH0157118B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19931217 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19981215 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19931217 Comment text: Patent Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20010516 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20020401 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20020625 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20020626 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20050418 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20060509 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20070413 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20080414 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20090415 Start annual number: 8 End annual number: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20100531 Start annual number: 9 End annual number: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20110530 Start annual number: 10 End annual number: 10 |
|
| FPAY | Annual fee payment |
Payment date: 20120530 Year of fee payment: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20120530 Start annual number: 11 End annual number: 11 |
|
| FPAY | Annual fee payment |
Payment date: 20130531 Year of fee payment: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20130531 Start annual number: 12 End annual number: 12 |
|
| EXPY | Expiration of term | ||
| PC1801 | Expiration of term |
Termination date: 20140617 Termination category: Expiration of duration |