JPS6316395B2 - - Google Patents

Info

Publication number: JPS6316395B2
Authority: JP; Japan
Prior art keywords: fluorine; formula; uridine; general formula; group
Prior art date: 1982-12-09
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

JP21574882A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59106498A (ja

Inventor

Takao Takahara

Yorisato Hisanaga

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.)

Daikin Industries Ltd

Original Assignee

Daikin Kogyo 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.)

1982-12-09

Filing date

1982-12-09

Publication date

1988-04-08

1982-12-09 Application filed by Daikin Kogyo Co Ltd filed Critical Daikin Kogyo Co Ltd

1982-12-09 Priority to JP21574882A priority Critical patent/JPS59106498A/ja

1983-12-07 Priority to DE8383112293T priority patent/DE3362821D1/de

1983-12-07 Priority to US06/558,913 priority patent/US4542209A/en

1983-12-07 Priority to EP83112293A priority patent/EP0111299B1/en

1984-06-20 Publication of JPS59106498A publication Critical patent/JPS59106498A/ja

1988-04-08 Publication of JPS6316395B2 publication Critical patent/JPS6316395B2/ja

Status Granted legal-status Critical Current

Links

YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 32
229910052731 fluorine Inorganic materials 0.000 claims description 32
239000011737 fluorine Substances 0.000 claims description 32
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 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 10
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 claims description 8
DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 claims description 8
229940045145 uridine Drugs 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
GFDUSNQQMOENLR-PEBGCTIMSA-N 1-[(3ar,4r,6r,6ar)-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)[C@H]3OC(O[C@H]32)(C)C)C=CC(=O)NC1=O GFDUSNQQMOENLR-PEBGCTIMSA-N 0.000 claims 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 8
239000002246 antineoplastic agent Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
229960002949 fluorouracil Drugs 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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 description 3
229960000583 acetic acid Drugs 0.000 description 3
230000001093 anti-cancer Effects 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000002994 raw material Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
238000003682 fluorination reaction Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
-1 uridine compound Chemical class 0.000 description 2
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000000034 method Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
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 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229940035893 uracil Drugs 0.000 description 1

Landscapes

Saccharide Compounds (AREA)

JP21574882A 1982-12-09 1982-12-09 含フツ素ウリジン類及びその製法 Granted JPS59106498A (ja)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
JP21574882A JPS59106498A (ja)	1982-12-09	1982-12-09	含フツ素ウリジン類及びその製法
DE8383112293T DE3362821D1 (en)	1982-12-09	1983-12-07	Fluorine-containing uridine derivative and preparation and use thereof
US06/558,913 US4542209A (en)	1982-12-09	1983-12-07	Fluorine-containing uridine derivative and preparation and use thereof
EP83112293A EP0111299B1 (en)	1982-12-09	1983-12-07	Fluorine-containing uridine derivative and preparation and use thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP21574882A JPS59106498A (ja)	1982-12-09	1982-12-09	含フツ素ウリジン類及びその製法

Publications (2)

Publication Number	Publication Date
JPS59106498A JPS59106498A (ja)	1984-06-20
JPS6316395B2 true JPS6316395B2 (pl)	1988-04-08

Family

ID=16677555

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP21574882A Granted JPS59106498A (ja)	1982-12-09	1982-12-09	含フツ素ウリジン類及びその製法

Country Status (1)

Country	Link
JP (1)	JPS59106498A (pl)

1982
- 1982-12-09 JP JP21574882A patent/JPS59106498A/ja active Granted

Also Published As

Publication number	Publication date
JPS59106498A (ja)	1984-06-20

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