MX2007000959A - Derivados de 1-alfa-halo-2,2-difluoro-2-desoxi-d-ribofuranosa y proceso para la preparacion de los mismos. - Google Patents

Derivados de 1-alfa-halo-2,2-difluoro-2-desoxi-d-ribofuranosa y proceso para la preparacion de los mismos.

Info

Publication number: MX2007000959A
Authority: MX; Mexico
Prior art keywords: formula; compound; derivative; mixture; iii
Prior art date: 2004-07-29

Application number

MX2007000959A

Other languages

English (en)

Spanish (es)

Inventor

Young-Kil Chang

Gwan Sun Lee

Han Kyong Kim

Jaeheon Lee

Moonsub Lee

Gha Seung Park

Hyo-Jeong Bang

Original Assignee

Hanmi Pharm Ind 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.)

2004-07-29

Filing date

2005-06-21

Publication date

2007-04-16

2005-06-21 Application filed by Hanmi Pharm Ind Co Ltd filed Critical Hanmi Pharm Ind Co Ltd

2005-06-21 Priority claimed from PCT/KR2005/001922 external-priority patent/WO2006011713A1/en

2007-04-16 Publication of MX2007000959A publication Critical patent/MX2007000959A/es

Links

238000000034 method Methods 0.000 title claims abstract description 30
238000002360 preparation method Methods 0.000 title abstract description 28
150000001875 compounds Chemical class 0.000 claims abstract description 71
-1 biphenylcarbonyl group Chemical group 0.000 claims abstract description 43
239000007787 solid Substances 0.000 claims abstract description 25
238000001953 recrystallisation Methods 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 48
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
229910019142 PO4 Inorganic materials 0.000 claims description 29
239000010452 phosphate Substances 0.000 claims description 29
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
229910052794 bromium Inorganic materials 0.000 claims description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
150000004820 halides Chemical class 0.000 claims description 11
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
235000019260 propionic acid Nutrition 0.000 claims description 5
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 2
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims description 2
229910052792 caesium Inorganic materials 0.000 claims description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 1
SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 abstract description 11
229960005277 gemcitabine Drugs 0.000 abstract description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 18
239000010410 layer Substances 0.000 description 18
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
125000001475 halogen functional group Chemical group 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
101150041968 CDC13 gene Proteins 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
238000006206 glycosylation reaction Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000012259 ether extract Substances 0.000 description 5
239000011630 iodine Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
238000007796 conventional method Methods 0.000 description 4
229940104302 cytosine Drugs 0.000 description 4
230000013595 glycosylation Effects 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 3
239000000872 buffer Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
238000002955 isolation Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000002777 nucleoside Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
208000002154 non-small cell lung carcinoma Diseases 0.000 description 2
239000007858 starting material Substances 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 2
RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
SWJBITNFDYHWBU-UHFFFAOYSA-N [I].[I] Chemical compound [I].[I] SWJBITNFDYHWBU-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002243 furanoses Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
150000003833 nucleoside derivatives Chemical class 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
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/08—Deoxysugars; Unsaturated sugars; Osones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

MX2007000959A 2004-07-29 2005-06-21 Derivados de 1-alfa-halo-2,2-difluoro-2-desoxi-d-ribofuranosa y proceso para la preparacion de los mismos. MX2007000959A (es)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
KR20040059623		2004-07-29
KR1020050041278A KR100699099B1 (ko)	2004-07-29	2005-05-17	1-α-할로-2,2-다이플루오로-2-데옥시-Ｄ-라이보퓨라노스유도체 및 이의 제조방법
PCT/KR2005/001922 WO2006011713A1 (en)	2004-07-29	2005-06-21	1-α-HALO-2,2-DIFLUORO-2-DEOXY-D-RIBOFURANOSE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF

Publications (1)

Publication Number	Publication Date
MX2007000959A true MX2007000959A (es)	2007-04-16

Family

ID=37149831

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
MX2007000959A MX2007000959A (es)	2004-07-29	2005-06-21	Derivados de 1-alfa-halo-2,2-difluoro-2-desoxi-d-ribofuranosa y proceso para la preparacion de los mismos.

Country Status (6)

Country	Link
JP (1)	JP4691101B2 (ja)
KR (1)	KR100699099B1 (ja)
CN (1)	CN1989148B (ja)
IL (1)	IL180894A (ja)
MX (1)	MX2007000959A (ja)
RU (1)	RU2346948C2 (ja)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7994310B2 (en)	2007-03-23	2011-08-09	Dongwoo Syntech Co., Ltd.	Process for preparing 2′-deoxy-2′, 2′-difluorocytidine
KR100858842B1 (ko) *	2007-03-23	2008-09-22	동우신테크 주식회사	키랄아민을 이용한 광학활성 옥소라이보스유도체의제조방법
CN101628927B (zh) *	2009-08-07	2012-10-10	卡硼瑞（北京）科技有限公司	以1,3,5-三-O-苯甲酰基-α-D-呋喃核糖为原料立体选择性制备β-二氟胞苷盐酸盐的方法
CN103897008A (zh) *	2012-12-28	2014-07-02	石药集团中奇制药技术（石家庄）有限公司	一种地西他滨及其中间体的制备方法

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US5223608A (en) *	1987-08-28	1993-06-29	Eli Lilly And Company	Process for and intermediates of 2',2'-difluoronucleosides
CA2039403A1 (en) *	1990-04-04	1991-10-05	Gerald Saischek	Process for the manufacture of 2-deoxy-d-threo-pentofuranosides, intermediates for their manufacture and their use
HU214030B (en) *	1992-06-22	1997-12-29	Lilly Co Eli	Process for preparing alpha-anomer enriched 1-halogen-2-deoxy-2,2-difluoro-d-ribofuranosyl derivatives
RU2131880C1 (ru) *	1992-06-22	1999-06-20	Эли Лилли Энд Компани	Способ получения обогащенных бета-аномером нуклеозидов
NZ247936A (en) *	1992-06-22	1995-05-26	Lilly Co Eli	Stereoselective anion glycosylation process for the preparation of a beta anomer enriched nucleoside
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JP2003055364A (ja) *	2001-06-07	2003-02-26	Mitsui Chemicals Inc	２，３−ジデオキシ−２，３−デヒドロペントフラノース誘導体に関する新規製造法

2005
- 2005-05-17 KR KR1020050041278A patent/KR100699099B1/ko not_active Expired - Lifetime
- 2005-06-21 CN CN2005800251579A patent/CN1989148B/zh not_active Expired - Fee Related
- 2005-06-21 MX MX2007000959A patent/MX2007000959A/es active IP Right Grant
- 2005-06-21 JP JP2007523465A patent/JP4691101B2/ja not_active Expired - Fee Related
- 2005-06-21 RU RU2007107607/04A patent/RU2346948C2/ru not_active IP Right Cessation
2007
- 2007-01-23 IL IL180894A patent/IL180894A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
JP4691101B2 (ja)	2011-06-01
RU2346948C2 (ru)	2009-02-20
KR20060047970A (ko)	2006-05-18
RU2007107607A (ru)	2008-09-10
IL180894A (en)	2011-09-27
CN1989148B (zh)	2010-05-12
KR100699099B1 (ko)	2007-03-22
HK1100946A1 (en)	2007-10-05
CN1989148A (zh)	2007-06-27
IL180894A0 (en)	2007-07-04
JP2008508261A (ja)	2008-03-21

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EP2160397B1 (en)	2014-03-26	A novel and highly stereoselective process for preparing gemcitabine and intermediates thereof
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US5633366A (en)	1997-05-27	Pyrimidine nucleoside derivatives and methods for producing them
IL180894A (en)	2011-09-27	1-alpha-halo-2,2-difluoro-2-deoxy-d-ribofuranose derivatives and processes for the preparation thereof
EP1781677A1 (en)	2007-05-09	Method for the preparation of d-erythro-2,2-difluoro-2-deoxy-1-oxoribose derivative
US5262531A (en)	1993-11-16	Process for preparing 2'-deoxy-β-adenosine
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CA2574954C (en)	2010-04-20	1-.alpha.-halo-2,2-difluoro-2-deoxy-d-ribofuranose derivatives and process for the preparation thereof
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JP6898323B2 (ja)	2021-07-07	６−アジド−２，４−ジアセトアミド−２，４，６−トリデオキシ−ｄ−マンノースの調製方法
HK1100946B (en)	2010-09-30	1-α-HALO-2,2-DIFLUORO-2-DEOXY-D-RIBOFURANOSE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF
KR100957756B1 (ko)	2010-05-12	2'-데옥시-2',2'-다이플루오로사이티딘의 제조 방법
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JPH0570473A (ja)	1993-03-23	β−グリコシドの製造法
KR20070119422A (ko)	2007-12-20	신규한 ｄ-에리트로-2-데옥시-2,2-디플루오로-1-옥소리보스화합물 및 그 제조방법

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2009-10-23	FG	Grant or registration
2011-09-08	GB	Transfer or rights
2012-12-04	HC	Change of company name or juridical status