JPS6256157B2 - - Google Patents

Info

Publication number: JPS6256157B2
Authority: JP; Japan
Prior art keywords: isopropylidene; fluorouracil; added; methanol; compound
Prior art date: 1982-06-24
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

JP10896282A

Other languages

English (en)

Japanese (ja)

Other versions

JPS591498A (ja

Inventor

Tatsuro Oochi

Minoru Imoto

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.)

JNC Corp

Original Assignee

Chisso Corp

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.)

1982-06-24

Filing date

1982-06-24

Publication date

1987-11-24

1982-06-24 Application filed by Chisso Corp filed Critical Chisso Corp

1982-06-24 Priority to JP10896282A priority Critical patent/JPS591498A/ja

1984-01-06 Publication of JPS591498A publication Critical patent/JPS591498A/ja

1987-11-24 Publication of JPS6256157B2 publication Critical patent/JPS6256157B2/ja

Status Granted legal-status Critical Current

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
150000001875 compounds Chemical class 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
229960002949 fluorouracil Drugs 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000000034 method Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
KEJGAYKWRDILTF-JDDHQFAOSA-N (3ar,5s,6s,6ar)-5-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol Chemical compound O1C(C)(C)OC[C@@H]1[C@@H]1[C@H](O)[C@H]2OC(C)(C)O[C@H]2O1 KEJGAYKWRDILTF-JDDHQFAOSA-N 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
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 2
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
229940045803 cuprous chloride Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
AVVWPBAENSWJCB-IVMDWMLBSA-N D-glucofuranose Chemical compound OC[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O AVVWPBAENSWJCB-IVMDWMLBSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
WFWLQNSHRPWKFK-UHFFFAOYSA-N Tegafur Chemical compound O=C1NC(=O)C(F)=CN1C1OCCC1 WFWLQNSHRPWKFK-UHFFFAOYSA-N 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000000340 anti-metabolite Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940100197 antimetabolite Drugs 0.000 description 1
239000002256 antimetabolite Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
229960004857 mitomycin Drugs 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229940035893 uracil Drugs 0.000 description 1

Landscapes

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

JP10896282A 1982-06-24 1982-06-24 １，２：５，６−ジ−０−イソプロピリデン−３−０〔３−（５−フルオロウラシル−１−イル）プロピオノイル〕α−Ｄ−グルコフラノ−ス Granted JPS591498A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP10896282A JPS591498A (ja)	1982-06-24	1982-06-24	１，２：５，６−ジ−０−イソプロピリデン−３−０〔３−（５−フルオロウラシル−１−イル）プロピオノイル〕α−Ｄ−グルコフラノ−ス

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP10896282A JPS591498A (ja)	1982-06-24	1982-06-24	１，２：５，６−ジ−０−イソプロピリデン−３−０〔３−（５−フルオロウラシル−１−イル）プロピオノイル〕α−Ｄ−グルコフラノ−ス

Publications (2)

Publication Number	Publication Date
JPS591498A JPS591498A (ja)	1984-01-06
JPS6256157B2 true JPS6256157B2 (2)	1987-11-24

Family

ID=14498065

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10896282A Granted JPS591498A (ja)	1982-06-24	1982-06-24	１，２：５，６−ジ−０−イソプロピリデン−３−０〔３−（５−フルオロウラシル−１−イル）プロピオノイル〕α−Ｄ−グルコフラノ−ス

Country Status (1)

Country	Link
JP (1)	JPS591498A (2)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU1235864A1 (ru) *	1983-03-11	1986-06-07	Отделение ордена Ленина института химической физики АН СССР	Нитроксильные производные 5-фторурацила,обладающие противоопухолевой активностью

1982
- 1982-06-24 JP JP10896282A patent/JPS591498A/ja active Granted

Also Published As

Publication number	Publication date
JPS591498A (ja)	1984-01-06

Similar Documents

Publication	Publication Date	Title
US4620008A (en)	1986-10-28	Processes for the preparation of omeprazole and intermediates therefore
Neilson et al.	1971	Oligoribonucleotide Synthesis. II. Preparation of 2′-O-tetrahydropyranyl Derivatives of Adenosine and Cytidine Necessary for Insertion in Stepwise Synthesis
US4111958A (en)	1978-09-05	Ascorbic acid synthesis
US3349095A (en)	1967-10-24	1-(5'-nitrofuryl)-1, 3-diketopropane derivatives and their preparation
DK170233B1 (da)	1995-07-10	Fremgangsmåde til fremstilling af alkoxymethylether- og alkoxymethylesterderivater af glyceroler
EP2149577B1 (en)	2011-04-27	New stereospecific method for the preparation of dioxa-bicyclooctane compounds
EP0072977A1 (en)	1983-03-02	Process for the production of 2-beta-D-ribofuranosylthiazole-4-carboxamide
HU208533B (en)	1993-11-29	Process for selective etherification of ascorbinic acid derivatives
US4588824A (en)	1986-05-13	Preparation of epihalohydrin enantiomers
JP3989997B2 (ja)	2007-10-10	放射線増感剤の製造方法
Kaats-Richters et al.	1994	Large Scale Monotritylation of Water Soluble Compounds Containing Multiple Hydroxyl Groups
JP3259191B2 (ja)	2002-02-25	２，２′−アンヒドロアラビノシルチミン誘導体の合成法
JPH0798833B2 (ja)	1995-10-25	２′−ブロモ−２′，３′−ジデヒドロ−２′，３′−ジデオキシシチジン及びその製造法
US4249006A (en)	1981-02-03	Method of producing 5-fluorouracil derivatives
DD250206A1 (de)	1987-09-30	Verfahren zur herstellung von 5-vinylpyrimidinen
EP0806425A1 (en)	1997-11-12	An improved regiospecific process for synthesis of acyclic nucleosides
JPH013194A (ja)	1989-01-06	２′−ブロモ−２′，３′−ジデヒドロ−２′，３′−ジデオキシシチジン及びその製造法
JPH0692394B2 (ja)	1994-11-16	２’，３’−ジデオキシシチジンの製造方法
JP2547125B2 (ja)	1996-10-23	２’，３’−ジデオキシ−２’，３’−ジ置換−ヌクレオシド類とその製造方法
JPS591498A (ja)	1984-01-06	１，２：５，６−ジ−０−イソプロピリデン−３−０〔３−（５−フルオロウラシル−１−イル）プロピオノイル〕α−Ｄ−グルコフラノ−ス
JPH0469156B2 (2)	1992-11-05
HU198949B (en)	1989-12-28	Process for producing 5-substituted-3'azido-2',3'-dideoxyribonucleosides
JPH0248594A (ja)	1990-02-19	Ｄ−グルコフラノース又はｄ−キシロフラノース誘導体の製法
JPH05339264A (ja)	1993-12-21	１−（２，３−ジデオキシ−ｄ−グリセロ−ペントフラノシル）チミン誘導体の製造方法
JPS6029396B2 (ja)	1985-07-10	５↓−フルオロウラシル誘導体の製法