ZA200303198B - Phase transfer catalyzed glycosidation of an indolocarbazole. - Google Patents

Phase transfer catalyzed glycosidation of an indolocarbazole. Download PDF

Info

Publication number: ZA200303198B
Authority: ZA; South Africa
Prior art keywords: alkyl; formula; compound; hydroxide; obn
Prior art date: 2000-10-31

Application number

ZA200303198A

Other languages

English (en)

Inventor

Daniel E Petrillo

Steven A Weissman

Kai Rossen

Shouichi Hiraga

Nobuya Satake

Original Assignee

Merck & Co Inc

Banyu Pharma Co Ltd

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.)

2000-10-31

Filing date

2003-04-24

Publication date

2004-04-23

2003-04-24 Application filed by Merck & Co Inc, Banyu Pharma Co Ltd filed Critical Merck & Co Inc

2004-04-23 Publication of ZA200303198B publication Critical patent/ZA200303198B/en

Links

238000005858 glycosidation reaction Methods 0.000 title description 8
238000012546 transfer Methods 0.000 title description 5
VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 title description 3
229960005544 indolocarbazole Drugs 0.000 title description 2
125000000217 alkyl group Chemical group 0.000 claims description 61
150000001875 compounds Chemical class 0.000 claims description 51
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 40
238000000034 method Methods 0.000 claims description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 18
239000007864 aqueous solution Substances 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
150000002243 furanoses Chemical group 0.000 claims description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
-1 9-fluorenylmethylcarbonyl Chemical group 0.000 claims description 14
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 14
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 14
239000003153 chemical reaction reagent Substances 0.000 claims description 11
238000005859 coupling reaction Methods 0.000 claims description 11
GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical group [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
239000003444 phase transfer catalyst Substances 0.000 claims description 9
125000005275 alkylenearyl group Chemical group 0.000 claims description 8
230000002051 biphasic effect Effects 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 8
150000003215 pyranoses Chemical group 0.000 claims description 8
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 7
230000003213 activating effect Effects 0.000 claims description 7
230000008878 coupling Effects 0.000 claims description 7
238000010168 coupling process Methods 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
239000000010 aprotic solvent Substances 0.000 claims description 4
150000008282 halocarbons Chemical class 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims description 3
WUIYQFDCODJYLD-UHFFFAOYSA-N 2-hydrazinylpropane-1,3-diol Chemical compound NNC(CO)CO WUIYQFDCODJYLD-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
229920000180 alkyd Polymers 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
206010028980 Neoplasm Diseases 0.000 description 8
239000000203 mixture Substances 0.000 description 8
150000003214 pyranose derivatives Chemical group 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
201000011510 cancer Diseases 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
239000000543 intermediate Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000003534 dna topoisomerase inhibitor Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
229940044693 topoisomerase inhibitor Drugs 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000011161 development Methods 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
HDEMQQHXNOJATE-NSHGFSBMSA-N (3r,4s,6s)-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound OC[C@@H]1C[C@H](O)[C@@H](O)C(O)O1 HDEMQQHXNOJATE-NSHGFSBMSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 2
FPMICYBCFBLGOZ-UHFFFAOYSA-N 6-phenylmethoxy-1h-indole Chemical compound C=1C=C2C=CNC2=CC=1OCC1=CC=CC=C1 FPMICYBCFBLGOZ-UHFFFAOYSA-N 0.000 description 2
RZIKICIKKLCFEQ-VBQYTDQYSA-N C(C1=CC=CC=C1)[C@@]1(C(O)O[C@@H]([C@]([C@@]1(O)CC1=CC=CC=C1)(O)CC1=CC=CC=C1)COCC1=CC=CC=C1)O Chemical compound C(C1=CC=CC=C1)[C@@]1(C(O)O[C@@H]([C@]([C@@]1(O)CC1=CC=CC=C1)(O)CC1=CC=CC=C1)COCC1=CC=CC=C1)O RZIKICIKKLCFEQ-VBQYTDQYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
238000013459 approach Methods 0.000 description 2
229950005499 carbon tetrachloride Drugs 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229940117389 dichlorobenzene Drugs 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000000746 purification Methods 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
230000004614 tumor growth Effects 0.000 description 2
239000008096 xylene Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 1
NFNSCJBDSVECIZ-AQWYAALZSA-N (3r,4r,5r,6r)-6-(hydroxymethyl)-5-methoxyoxane-2,3,4,5-tetrol Chemical compound CO[C@]1(O)[C@H](O)[C@@H](O)C(O)O[C@@H]1CO NFNSCJBDSVECIZ-AQWYAALZSA-N 0.000 description 1
FXVPOMKTIZKCTJ-GASJEMHNSA-N (3r,4s,5s,6r)-6-(aminomethyl)oxane-2,3,4,5-tetrol Chemical compound NC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O FXVPOMKTIZKCTJ-GASJEMHNSA-N 0.000 description 1
CMLRUUHRGSJVMD-GASJEMHNSA-N (3r,4s,5s,6r)-6-(azidomethyl)oxane-2,3,4,5-tetrol Chemical compound OC1O[C@H](CN=[N+]=[N-])[C@@H](O)[C@H](O)[C@H]1O CMLRUUHRGSJVMD-GASJEMHNSA-N 0.000 description 1
CSWKRWZKIUAKKR-AQKNRBDQSA-N (3r,4s,5s,6s)-6-(difluoromethyl)oxane-2,3,4,5-tetrol Chemical compound OC1O[C@H](C(F)F)[C@@H](O)[C@H](O)[C@H]1O CSWKRWZKIUAKKR-AQKNRBDQSA-N 0.000 description 1
NGMXFJBRMSEJIO-IGBKFWFVSA-N (3r,4s,5s,6s)-6-[amino(hydroxy)methyl]oxane-2,3,4,5-tetrol Chemical compound NC(O)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O NGMXFJBRMSEJIO-IGBKFWFVSA-N 0.000 description 1
YEHSYXLCIYFVLZ-IGBKFWFVSA-N (3r,4s,5s,6s)-6-[azido(hydroxy)methyl]oxane-2,3,4,5-tetrol Chemical compound [N-]=[N+]=NC(O)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O YEHSYXLCIYFVLZ-IGBKFWFVSA-N 0.000 description 1
PWKRGOPUVNGKKZ-RCSKTBSMSA-N (3s,4s,5s,6r)-3-fluoro-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1OC(O)[C@@](O)(F)[C@@H](O)[C@@H]1O PWKRGOPUVNGKKZ-RCSKTBSMSA-N 0.000 description 1
PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
CKITYUQKOJMMOI-UHFFFAOYSA-N 3,4-dibromo-1-methylpyrrole-2,5-dione Chemical compound CN1C(=O)C(Br)=C(Br)C1=O CKITYUQKOJMMOI-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
AVVWPBAENSWJCB-CBPJZXOFSA-N D-allofuranose Chemical compound OC[C@@H](O)[C@H]1OC(O)[C@H](O)[C@@H]1O AVVWPBAENSWJCB-CBPJZXOFSA-N 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
HMFHBZSHGGEWLO-IOVATXLUSA-N D-xylofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H]1O HMFHBZSHGGEWLO-IOVATXLUSA-N 0.000 description 1
102100028701 General vesicular transport factor p115 Human genes 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
101000767151 Homo sapiens General vesicular transport factor p115 Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
HMFHBZSHGGEWLO-HWQSCIPKSA-N L-arabinofuranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@H]1O HMFHBZSHGGEWLO-HWQSCIPKSA-N 0.000 description 1
241000283986 Lepus Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
101500025412 Mus musculus Processed cyclic AMP-responsive element-binding protein 3-like protein 1 Proteins 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
SLSKZXFHTNGVJQ-UHFFFAOYSA-N OC.CC(C)=O.CCCCCC.CCOC(C)=O Chemical compound OC.CC(C)=O.CCCCCC.CCOC(C)=O SLSKZXFHTNGVJQ-UHFFFAOYSA-N 0.000 description 1
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229910020667 PBr3 Inorganic materials 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229910019201 POBr3 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910006121 SOBr2 Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000004450 alkenylene group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 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
239000006227 byproduct Substances 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
QFDRKNYLQVKPEE-UHFFFAOYSA-N chloroform ethanol methanol hydrate Chemical compound O.OC.CCO.ClC(Cl)Cl QFDRKNYLQVKPEE-UHFFFAOYSA-N 0.000 description 1
RDOVFNRYRPOOMG-UHFFFAOYSA-N chloroform;ethanol;methanol;oxolane Chemical compound OC.CCO.ClC(Cl)Cl.C1CCOC1 RDOVFNRYRPOOMG-UHFFFAOYSA-N 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000000470 constituent Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
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
LBOZPYNUPOEJDO-UHFFFAOYSA-N dichloromethane;hexane;propan-2-one Chemical compound ClCCl.CC(C)=O.CCCCCC LBOZPYNUPOEJDO-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000001035 drying Methods 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
JYGYEBCBALMPDC-UHFFFAOYSA-N heptane;propan-2-one Chemical compound CC(C)=O.CCCCCCC JYGYEBCBALMPDC-UHFFFAOYSA-N 0.000 description 1
SYYYTWUJLCMOQF-UHFFFAOYSA-N hexane;methanol;propan-2-one Chemical compound OC.CC(C)=O.CCCCCC SYYYTWUJLCMOQF-UHFFFAOYSA-N 0.000 description 1
RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 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
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000005017 substituted alkenyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
- 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
- C07H19/23—Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biotechnology (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ZA200303198A 2000-10-31 2003-04-24 Phase transfer catalyzed glycosidation of an indolocarbazole. ZA200303198B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US24467500P	2000-10-31	2000-10-31

Publications (1)

Publication Number	Publication Date
ZA200303198B true ZA200303198B (en)	2004-04-23

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ID=22923680

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200303198A ZA200303198B (en)	2000-10-31	2003-04-24	Phase transfer catalyzed glycosidation of an indolocarbazole.

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US (2)	US6555677B2 (ru)
EP (1)	EP1333826A2 (ru)
JP (1)	JP3554560B2 (ru)
KR (1)	KR100813086B1 (ru)
CN (1)	CN1240380C (ru)
AU (2)	AU2894502A (ru)
BG (1)	BG107737A (ru)
BR (1)	BR0115036A (ru)
CA (1)	CA2426815A1 (ru)
CZ (1)	CZ20031209A3 (ru)
EA (1)	EA005209B1 (ru)
HK (1)	HK1064053A1 (ru)
HU (1)	HUP0302923A3 (ru)
IL (1)	IL155543A0 (ru)
IS (1)	IS6791A (ru)
MX (1)	MXPA03003871A (ru)
NO (1)	NO20031922L (ru)
NZ (1)	NZ525398A (ru)
PL (1)	PL365574A1 (ru)
WO (1)	WO2002036601A2 (ru)
ZA (1)	ZA200303198B (ru)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6555677B2 (en) *	2000-10-31	2003-04-29	Merck & Co., Inc.	Phase transfer catalyzed glycosidation of an indolocarbazole
US7429572B2 (en) *	2003-05-30	2008-09-30	Pharmasset, Inc.	Modified fluorinated nucleoside analogues
JPWO2005026185A1 (ja) *	2003-09-16	2006-11-16	萬有製薬株式会社	抗腫瘍性新規インドロピロロカルバゾール誘導体
WO2005116044A1 (ja) *	2004-05-28	2005-12-08	Banyu Pharmaceutical Co.,Ltd	インドロピロロカルバゾール誘導体の製造法
CN101023094B (zh) *	2004-07-21	2011-05-18	法莫赛特股份有限公司	烷基取代的2-脱氧-2-氟代-d-呋喃核糖基嘧啶和嘌呤及其衍生物的制备
SI3109244T1 (sl) *	2004-09-14	2019-06-28	Gilead Pharmasset Llc	Priprava 2'fluoro-2'-alkil-substituiranih ali drugih neobvezno substituiranih ribofuranozil pirimidinov in purinov in njihovih derivatov
US7537774B2 (en) *	2005-12-23	2009-05-26	Orion Therapeautics, Llc	Therapeutic formulation
US7964580B2 (en)	2007-03-30	2011-06-21	Pharmasset, Inc.	Nucleoside phosphoramidate prodrugs
US8173621B2 (en)	2008-06-11	2012-05-08	Gilead Pharmasset Llc	Nucleoside cyclicphosphates
EA019341B1 (ru)	2008-12-23	2014-02-28	Джилид Фармассет, Ллс.	Фосфорамидаты нуклеозидов
WO2010075554A1 (en)	2008-12-23	2010-07-01	Pharmasset, Inc.	Synthesis of purine nucleosides
PA8855701A1 (es)	2008-12-23	2010-07-27		Análogos de nucleósidos
US8618076B2 (en)	2009-05-20	2013-12-31	Gilead Pharmasset Llc	Nucleoside phosphoramidates
TWI583692B (zh)	2009-05-20	2017-05-21	基利法瑪席特有限責任公司	核苷磷醯胺
BR112012024884A2 (pt)	2010-03-31	2016-10-18	Gilead Pharmasset Llc	síntese estereosseletiva de ativos contendo fósforo
PL3290428T3 (pl)	2010-03-31	2022-02-07	Gilead Pharmasset Llc	Tabletka zawierająca krystaliczny (S)-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-diokso-3,4-dihydropirymidyn-1(2H)-ylo)-4-fluoro-3-hydroksy-4-metylotetrahydrofuran-2-ylo)metoksy)(fenoksy)fosforylo)amino)propanian izopropylu
EP2646453A1 (en)	2010-11-30	2013-10-09	Gilead Pharmasset LLC	Compounds
US8889159B2 (en)	2011-11-29	2014-11-18	Gilead Pharmasset Llc	Compositions and methods for treating hepatitis C virus
PT3650014T (pt)	2013-08-27	2021-12-27	Gilead Pharmasset Llc	Formulação combinada de dois compostos antivirais

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4808613A (en)	1986-11-21	1989-02-28	Bristol-Myers Company	Rebeccamycin derivative containing pharmaceutical composition
GB8818430D0 (en) *	1988-08-03	1988-09-07	Tate & Lyle Plc	Process
US5668271A (en)	1991-11-29	1997-09-16	Banyu Pharmaceutical Co., Ltd.	Indolopyrrolocarbazole derivatives
US5591842A (en)	1991-11-29	1997-01-07	Banyu Pharmaceutical Co., Ltd.	Indolopyrrolocarbazole derivatives
NZ245203A (en)	1991-11-29	1997-07-27	Banyu Pharma Co Ltd	5h-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6h)-dione derivatives substituted in position-13 by a pentose or hexose group; corresponding indolo-furano(anhydride)intermediates
US5437996A (en)	1992-11-24	1995-08-01	Banyu Pharmaceutical Co., Ltd.	Microtetraspora strain for preparation of indolopyrrolocarbazole derivatives
US5589365A (en)	1991-11-29	1996-12-31	Banyu Pharmaceutical Co., Ltd.	Process for producing glycosylated indolopyrrolocarbazole derivatives by culturing certain microorganisms
US5468872A (en)	1993-09-16	1995-11-21	Cephalon, Inc.	K-252a functional derivatives potentiate neurotrophin-3 for the treatment of neurological disorders
EP0675125A1 (en)	1994-03-18	1995-10-04	Kyowa Hakko Kogyo Co., Ltd.	A therapeutic agent for thrombocytopenia and indolocarbazole derivatives
US5922860A (en) *	1994-05-09	1999-07-13	Banyu Pharmaceutical Co., Ltd.	Antitumor indolopyrrolocarbazole derivatives
US5804564A (en)	1994-05-09	1998-09-08	Banyu Pharmaceutical Co., Ltd.	Antitumor indolopyrrolocarbazole derivatives
FR2750135B1 (fr) *	1996-06-20	1998-08-14	Ceca Sa	Acides fluoroalkyl glycosides uroniques et lactones-6(3) correspondantes, preparation et utilisations
EP0971717B1 (en)	1996-08-22	2001-12-19	Bristol-Myers Squibb Company	Cytotoxic amino sugar and related sugar derivatives of indolopyrrolocarbazoles
US6555677B2 (en) *	2000-10-31	2003-04-29	Merck & Co., Inc.	Phase transfer catalyzed glycosidation of an indolocarbazole

2001
- 2001-10-22 US US10/002,061 patent/US6555677B2/en not_active Expired - Fee Related
- 2001-10-26 CA CA002426815A patent/CA2426815A1/en not_active Abandoned
- 2001-10-26 CN CNB018214029A patent/CN1240380C/zh not_active Expired - Fee Related
- 2001-10-26 AU AU2894502A patent/AU2894502A/xx active Pending
- 2001-10-26 CZ CZ20031209A patent/CZ20031209A3/cs unknown
- 2001-10-26 HU HU0302923A patent/HUP0302923A3/hu unknown
- 2001-10-26 BR BR0115036-7A patent/BR0115036A/pt not_active Withdrawn
- 2001-10-26 KR KR1020037005897A patent/KR100813086B1/ko not_active IP Right Cessation
- 2001-10-26 NZ NZ525398A patent/NZ525398A/xx unknown
- 2001-10-26 EP EP01990074A patent/EP1333826A2/en not_active Withdrawn
- 2001-10-26 IL IL15554301A patent/IL155543A0/xx unknown
- 2001-10-26 US US10/415,509 patent/US20040024196A1/en not_active Abandoned
- 2001-10-26 MX MXPA03003871A patent/MXPA03003871A/es active IP Right Grant
- 2001-10-26 PL PL01365574A patent/PL365574A1/xx not_active Application Discontinuation
- 2001-10-26 WO PCT/US2001/047603 patent/WO2002036601A2/en active IP Right Grant
- 2001-10-26 JP JP2002539359A patent/JP3554560B2/ja not_active Expired - Fee Related
- 2001-10-26 EA EA200300525A patent/EA005209B1/ru not_active IP Right Cessation
- 2001-10-26 AU AU2002228945A patent/AU2002228945B2/en not_active Ceased
2003
- 2003-04-16 IS IS6791A patent/IS6791A/is unknown
- 2003-04-17 BG BG107737A patent/BG107737A/bg unknown
- 2003-04-24 ZA ZA200303198A patent/ZA200303198B/en unknown
- 2003-04-29 NO NO20031922A patent/NO20031922L/no not_active Application Discontinuation
2004
- 2004-09-10 HK HK04106904A patent/HK1064053A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUP0302923A2 (hu)	2003-12-29
AU2894502A (en)	2002-05-15
NO20031922L (no)	2003-06-27
IL155543A0 (en)	2003-11-23
CZ20031209A3 (cs)	2003-10-15
PL365574A1 (en)	2005-01-10
NO20031922D0 (no)	2003-04-29
EA200300525A1 (ru)	2003-08-28
JP3554560B2 (ja)	2004-08-18
AU2002228945B2 (en)	2006-02-02
KR20030082545A (ko)	2003-10-22
CN1240380C (zh)	2006-02-08
IS6791A (is)	2003-04-16
US20040024196A1 (en)	2004-02-05
KR100813086B1 (ko)	2008-03-17
US20020058803A1 (en)	2002-05-16
HK1064053A1 (en)	2005-01-21
EA005209B1 (ru)	2004-12-30
CA2426815A1 (en)	2002-05-10
MXPA03003871A (es)	2003-07-28
US6555677B2 (en)	2003-04-29
CN1482908A (zh)	2004-03-17
EP1333826A2 (en)	2003-08-13
BG107737A (bg)	2004-01-30
HUP0302923A3 (en)	2005-02-28
WO2002036601A3 (en)	2002-11-28
BR0115036A (pt)	2004-02-25
JP2004513131A (ja)	2004-04-30
WO2002036601A2 (en)	2002-05-10
NZ525398A (en)	2004-12-24

Publication	Publication Date	Title
ZA200303198B (en)	2004-04-23	Phase transfer catalyzed glycosidation of an indolocarbazole.
AU2002228945A1 (en)	2002-07-18	Phase transfer catalyzed glycosidation of an indolocarbazole
DK172636B1 (en)	1999-03-22	6-o-methylerythromycin a derivative
EP1501848A1 (en)	2005-02-02	Synthesis of locked nucleic acid derivatives
CA2192950A1 (en)	1995-12-28	Novel method of preparation of known and novel 2'-modified nucleosides by intramolecular nucleophilic displacement
AU720721B2 (en)	2000-06-08	New isomerization process for the methyl radical at 10 of erythromycin derivatives
JPS6247196B2 (ru)	1987-10-06
WO2006119347A1 (en)	2006-11-09	STEREOSELECTIVE SYNTHESIS OF β-NUCLEOSIDES
WO2004106352A1 (ja)	2004-12-09	アルドヘキソピラノース中間体の製造法
EP1812457A1 (en)	2007-08-01	STEREOSELECTIVE SYNTHESIS OF ß-NUCLEOSIDES
KR900006217B1 (ko)	1990-08-25	에피포도필로톡신 배당체의 질소함유 유도체
KR960014102B1 (ko)	1996-10-14	타이로신유도체 및 그 제조법
Jurczak et al.	1996	Isoxazolidin-5-one-isoxazolidine rearrangement, an entry to 3-amino-3-deoxy sugars
Moura et al.	2018	Synthesis of phosphorus analogs of TSAO-T
US5061791A (en)	1991-10-29	4-bromo-4'-demethylepipodophyllotoxin derivatives
CA2359967C (en)	2011-08-30	Method for preparing an aza-macrolide with 4"(r)nh2
JP2010024213A (ja)	2010-02-04	糖１−リン酸化合物の製造方法
AU653788B2 (en)	1994-10-13	Process for the preparation of 4'-demethylepipodophyllotoxin glucoside 4'-phosphates
AU2006325622A1 (en)	2007-06-21	A manufacturing process of 2',2'-difluoronucleoside and intermediate
KR100834711B1 (ko)	2008-06-02	엔-아실-5'-데옥시-5-플루오로시티딘 유도체의 제조 방법
KR900004218B1 (ko)	1990-06-18	아미노글리코사이드계 항생물질 유도체의 제조방법
KR0161351B1 (ko)	1998-12-01	신규 티아(디아)졸 초산의 반응성 포스페이트 유도체 및 그의 제조방법
JPWO2003068792A1 (ja)	2005-06-02	エリスロマイシンａ誘導体の製造方法
JPH0529237B2 (ru)	1993-04-28
KR20020013081A (ko)	2002-02-20	안트라싸이클린계 항암제인 에피루비신 및 약학적으로허용되는 그 염의 제조방법