JPS621399B2 - - Google Patents

Info

Publication number: JPS621399B2
Authority: JP; Japan
Prior art keywords: fluorouridine; isopropylidene; proton; mmol; chloroform
Prior art date: 1979-11-28
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

Application number

JP15292279A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5677298A (en

Inventor

Takeshi Endo

Katsumi Sakai

Kyoaki Cho

Yoshitaka Inamoto

Haruhiko Teshigahara

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fuji Chemical Industries Co Ltd

Original Assignee

Fuji Chemical Industries 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.)

1979-11-28

Filing date

1979-11-28

Publication date

1987-01-13

1979-11-28 Application filed by Fuji Chemical Industries Co Ltd filed Critical Fuji Chemical Industries Co Ltd

1979-11-28 Priority to JP15292279A priority Critical patent/JPS5677298A/ja

1980-11-26 Priority to US06/210,796 priority patent/US4340728A/en

1980-11-27 Priority to IT26289/80A priority patent/IT1141100B/it

1980-11-27 Priority to DE19803044740 priority patent/DE3044740A1/de

1980-11-28 Priority to FR8025348A priority patent/FR2470774A1/fr

1980-11-28 Priority to CH883380A priority patent/CH646441A5/de

1980-11-28 Priority to GB8038211A priority patent/GB2066812B/en

1981-06-25 Publication of JPS5677298A publication Critical patent/JPS5677298A/ja

1987-01-13 Publication of JPS621399B2 publication Critical patent/JPS621399B2/ja

Status Granted legal-status Critical Current

Links

FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 claims description 17
238000005886 esterification reaction Methods 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
-1 phenylacetyl Chemical group 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 24
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
239000002904 solvent Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 14
238000004458 analytical method Methods 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
238000000921 elemental analysis Methods 0.000 description 12
150000002148 esters Chemical class 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 10
LHTMLCXJMYPWGR-NPDIDSPYSA-N 5-fluoro-1-[(4r,6r)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione Chemical compound N1([C@@H]2O[C@H](CO)C3OC(OC32)(C)C)C=C(F)C(=O)NC1=O LHTMLCXJMYPWGR-NPDIDSPYSA-N 0.000 description 10
235000013736 caramel Nutrition 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
239000000126 substance Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
238000000034 method Methods 0.000 description 7
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
150000001408 amides Chemical group 0.000 description 5
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000001118 alkylidene group Chemical group 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
MVGLBXWFOSHCCP-UHFFFAOYSA-N chloroform;tetrachloromethane Chemical compound ClC(Cl)Cl.ClC(Cl)(Cl)Cl MVGLBXWFOSHCCP-UHFFFAOYSA-N 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
238000004949 mass spectrometry Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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239000003054 catalyst Substances 0.000 description 3
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230000000694 effects Effects 0.000 description 3
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
OEAFZNRGZZNREY-SEFVSHJNSA-N 1-o-benzyl 2-o-[[(2r,3s,4r,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl] (2s)-pyrrolidine-1,2-dicarboxylate Chemical compound C([C@H]1C(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C(NC(=O)C(F)=C2)=O)CCN1C(=O)OCC1=CC=CC=C1 OEAFZNRGZZNREY-SEFVSHJNSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
HRBGUGQWTMBDTR-UHFFFAOYSA-N 2,3,4-tri(propan-2-yl)benzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C(C(C)C)=C1C(C)C HRBGUGQWTMBDTR-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 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
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 2
ZCXMFBUYRUWFAQ-PBEGBBSFSA-N [(2r,3s,4r,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2s)-2-(butanoylamino)-3-methylbutanoate Chemical compound O[C@@H]1[C@H](O)[C@@H](COC(=O)[C@H](C(C)C)NC(=O)CCC)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ZCXMFBUYRUWFAQ-PBEGBBSFSA-N 0.000 description 2
FKEFWONOONUTEI-FSNPWBFUSA-N [(2r,3s,4r,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2s)-3-methyl-2-(phenylmethoxycarbonylamino)butanoate Chemical compound N([C@@H](C(C)C)C(=O)OC[C@@H]1[C@H]([C@@H](O)[C@@H](O1)N1C(NC(=O)C(F)=C1)=O)O)C(=O)OCC1=CC=CC=C1 FKEFWONOONUTEI-FSNPWBFUSA-N 0.000 description 2
GLPMXIIHERHMQE-QBRBXANFSA-N [(2r,3s,4r,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate Chemical compound C([C@@H](C(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C(NC(=O)C(F)=C1)=O)O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 GLPMXIIHERHMQE-QBRBXANFSA-N 0.000 description 2
125000004448 alkyl carbonyl group Chemical group 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
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FAIZHAKOWDWMMK-ZAPJKBGESA-N [(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoate Chemical compound C(C1=CC=CC=C1)OC(=O)N[C@@H](CO)C(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C(=O)NC(=O)C(=C1)F)O)O FAIZHAKOWDWMMK-ZAPJKBGESA-N 0.000 description 1
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LZDZKYWQWUCFNC-PJDYVGSDSA-N [(2r,3s,4r,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2s)-3-(4-hydroxyphenyl)-2-(pentanoylamino)propanoate Chemical compound C([C@H](NC(=O)CCCC)C(=O)OC[C@@H]1[C@H]([C@@H](O)[C@@H](O1)N1C(NC(=O)C(F)=C1)=O)O)C1=CC=C(O)C=C1 LZDZKYWQWUCFNC-PJDYVGSDSA-N 0.000 description 1
XOLYMOAEPXAVGQ-PJDYVGSDSA-N [(2r,3s,4r,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2s)-4-methylsulfanyl-2-(3-phenylpropanoylamino)butanoate Chemical compound N([C@@H](CCSC)C(=O)OC[C@@H]1[C@H]([C@@H](O)[C@@H](O1)N1C(NC(=O)C(F)=C1)=O)O)C(=O)CCC1=CC=CC=C1 XOLYMOAEPXAVGQ-PJDYVGSDSA-N 0.000 description 1
DYADTGFGLFIFLN-LMWHNAIISA-N [(2r,3s,4r,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2s)-4-methylsulfanyl-2-(pentanoylamino)butanoate Chemical compound O[C@@H]1[C@H](O)[C@@H](COC(=O)[C@H](CCSC)NC(=O)CCCC)O[C@H]1N1C(=O)NC(=O)C(F)=C1 DYADTGFGLFIFLN-LMWHNAIISA-N 0.000 description 1
ZCGHCZMVDSJOFI-SEFVSHJNSA-N [(2r,3s,4r,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2s)-4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoate Chemical compound N([C@@H](CCSC)C(=O)OC[C@@H]1[C@H]([C@@H](O)[C@@H](O1)N1C(NC(=O)C(F)=C1)=O)O)C(=O)OCC1=CC=CC=C1 ZCGHCZMVDSJOFI-SEFVSHJNSA-N 0.000 description 1
NYJHRXPVSDZAFU-DNNBLBMLSA-N [(2r,3s,4r,5r)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl 2-(phenylmethoxycarbonylamino)acetate Chemical compound C([C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C(NC(=O)C(F)=C1)=O)OC(=O)CNC(=O)OCC1=CC=CC=C1 NYJHRXPVSDZAFU-DNNBLBMLSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
235000008206 alpha-amino acids Nutrition 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 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
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
229960003444 immunosuppressant agent Drugs 0.000 description 1
230000001861 immunosuppressant effect Effects 0.000 description 1
239000003018 immunosuppressive agent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
229960004452 methionine Drugs 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([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
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
229960005190 phenylalanine Drugs 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229960002429 proline Drugs 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
229960004799 tryptophan Drugs 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
229940045145 uridine Drugs 0.000 description 1
239000004474 valine Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP15292279A 1979-11-28 1979-11-28 Movel 5-fluorouridine derivative and its preparation Granted JPS5677298A (en)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
JP15292279A JPS5677298A (en)	1979-11-28	1979-11-28	Movel 5-fluorouridine derivative and its preparation
US06/210,796 US4340728A (en)	1979-11-28	1980-11-26	Nucleoside derivatives and process for preparing same
IT26289/80A IT1141100B (it)	1979-11-28	1980-11-27	Derivati nucleosidici e processo per la loro preparazione
DE19803044740 DE3044740A1 (de)	1979-11-28	1980-11-27	Nucleosidderivate, ihre herstellung und pharmazeutische mittel
FR8025348A FR2470774A1 (fr)	1979-11-28	1980-11-28	Derives de nucleosides, leur preparation et leurs utilisations therapeutiques
CH883380A CH646441A5 (de)	1979-11-28	1980-11-28	Nucleosidderivate, ihre herstellung und diese enthaltende pharmazeutische mittel.
GB8038211A GB2066812B (en)	1979-11-28	1980-11-28	5'-acyl-uridine derivatives and processes for the preparation thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP15292279A JPS5677298A (en)	1979-11-28	1979-11-28	Movel 5-fluorouridine derivative and its preparation

Publications (2)

Publication Number	Publication Date
JPS5677298A JPS5677298A (en)	1981-06-25
JPS621399B2 true JPS621399B2 (fr)	1987-01-13

Family

ID=15551073

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15292279A Granted JPS5677298A (en)	1979-11-28	1979-11-28	Movel 5-fluorouridine derivative and its preparation

Country Status (1)

Country	Link
JP (1)	JPS5677298A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61134397A (ja) *	1984-12-01	1986-06-21	Fuji Kagaku Kogyo Kk	５’−０−オリゴペプチジル−５−フルオロウリジン及びその製造方法
JPS61246196A (ja) *	1985-04-22	1986-11-01	Fuji Kagaku Kogyo Kk	５′−０−アシル−５−フルオロウリジン及びその製造方法
DE268678T1 (de) *	1986-05-30	1988-11-24	Fuji Kagaku Kogyo K.K., Toyama	Neue 5-fluoruridin-verbindungen und deren herstellung.

1979
- 1979-11-28 JP JP15292279A patent/JPS5677298A/ja active Granted

Also Published As

Publication number	Publication date
JPS5677298A (en)	1981-06-25

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US5401838A (en)	1995-03-28	Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
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