JPH0437832B2 - - Google Patents

Info

Publication number: JPH0437832B2
Authority: JP; Japan
Prior art keywords: compound; fluorouracil; bis; acid; solvent
Prior art date: 1984-03-21
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

JP5239884A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60197675A (ja

Inventor

Mikio Suzuki

Nihei Inomata

Tetsuo Ikegawa

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.)

Nippon Kasei Chemical Co Ltd

Original Assignee

Nippon Kasei Chemical 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.)

1984-03-21

Filing date

1984-03-21

Publication date

1992-06-22

1984-03-21 Application filed by Nippon Kasei Chemical Co Ltd filed Critical Nippon Kasei Chemical Co Ltd

1984-03-21 Priority to JP5239884A priority Critical patent/JPS60197675A/ja

1985-10-07 Publication of JPS60197675A publication Critical patent/JPS60197675A/ja

1992-06-22 Publication of JPH0437832B2 publication Critical patent/JPH0437832B2/ja

Status Granted legal-status Critical Current

Links

-1 1,3-bis(3,4-epoxybutyl)-5-fluorouracil Chemical compound 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
239000002246 antineoplastic agent Substances 0.000 claims description 6
229960002949 fluorouracil Drugs 0.000 claims description 5
150000004967 organic peroxy acids Chemical class 0.000 claims description 5
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
230000001590 oxidative effect Effects 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 35
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 9
239000007788 liquid Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
230000001093 anti-cancer Effects 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000007810 chemical reaction solvent Substances 0.000 description 4
238000010586 diagram Methods 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
230000004083 survival effect Effects 0.000 description 4
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
238000000034 method Methods 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000004593 Epoxy Substances 0.000 description 2
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 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000010255 intramuscular injection Methods 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
235000019345 sodium thiosulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
IUXHPSPHPKXTPA-UHFFFAOYSA-N 1-bromobut-1-ene Chemical compound CCC=CBr IUXHPSPHPKXTPA-UHFFFAOYSA-N 0.000 description 1
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
WBOQHFMXKCEWSQ-UHFFFAOYSA-N 4-hydroperoxy-4-oxobutanoic acid Chemical compound OOC(=O)CCC(O)=O WBOQHFMXKCEWSQ-UHFFFAOYSA-N 0.000 description 1
ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 4-nitrobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000003560 cancer drug Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
BRDYCNFHFWUBCZ-UHFFFAOYSA-N dodecaneperoxoic acid Chemical compound CCCCCCCCCCCC(=O)OO BRDYCNFHFWUBCZ-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000008151 electrolyte solution Substances 0.000 description 1
229940021013 electrolyte solution Drugs 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229960004393 lidocaine hydrochloride Drugs 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP5239884A 1984-03-21 1984-03-21 ５−フルオロウラシル誘導体，その製造法及び抗ガン剤 Granted JPS60197675A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP5239884A JPS60197675A (ja)	1984-03-21	1984-03-21	５−フルオロウラシル誘導体，その製造法及び抗ガン剤

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP5239884A JPS60197675A (ja)	1984-03-21	1984-03-21	５−フルオロウラシル誘導体，その製造法及び抗ガン剤

Publications (2)

Publication Number	Publication Date
JPS60197675A JPS60197675A (ja)	1985-10-07
JPH0437832B2 true JPH0437832B2 (ko)	1992-06-22

Family

ID=12913698

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5239884A Granted JPS60197675A (ja)	1984-03-21	1984-03-21	５−フルオロウラシル誘導体，その製造法及び抗ガン剤

Country Status (1)

Country	Link
JP (1)	JPS60197675A (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR101334321B1 (ko) *	2012-05-15	2013-11-28	현대중공업 주식회사	복사 차단막이 설치된 극저온 냉동기

1984
- 1984-03-21 JP JP5239884A patent/JPS60197675A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR101334321B1 (ko) *	2012-05-15	2013-11-28	현대중공업 주식회사	복사 차단막이 설치된 극저온 냉동기

Also Published As

Publication number	Publication date
JPS60197675A (ja)	1985-10-07

Publication	Publication Date	Title
US3987177A (en)	1976-10-19	Vincaminic acid esters
WO1993007114A1 (en)	1993-04-15	Oxygen substituted derivatives of nucleophile-nitric oxide adducts as nitric oxide donor prodrugs
JPS60139619A (ja)	1985-07-24	Ｏ−ベンジリデン−アスコルビン酸又はその塩よりなる抗腫瘍剤
US3268582A (en)	1966-08-23	Phenylalkyl-carboxylic acid amides
CA1331464C (en)	1994-08-16	Anti-tumor method and compounds
EP0318392B1 (fr)	1992-04-15	Nouveaux dérivés N-(vinblastinoyl-23) d'acide amino-1 méthylphosphonique, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent
JPH0437832B2 (ko)	1992-06-22
US4585589A (en)	1986-04-29	Water-soluble alkanoyloxy and alkoxycarbonyloxy rifampicin derivatives, process for its preparation, intermediates, and its pharmaceutical composition as antibacterials
SU1053749A3 (ru)	1983-11-07	Способ получени 1,2-бис-(никотинамидо)-пропана или его солей с фармацевтически приемлемой кислотой
US3474097A (en)	1969-10-21	Preparation of quinoxaline-n,n'-dioxides
JPS60197674A (ja)	1985-10-07	イソシアヌル酸誘導体、その製造法及び抗ガン剤
US3671583A (en)	1972-06-20	Glutaric acid derivatives
JPS5940400B2 (ja)	1984-09-29	新規ｄ−アロ−ス誘導体及びこれを有効成分とする抗腫瘍剤
US3041333A (en)	1962-06-26	Substituted cyclopropylcarboxyamido derivatives of penicillanic acid
WO2004089965A2 (en)	2004-10-21	Topiramate and processes for the preparation thereof
US3976646A (en)	1976-08-24	Process for preparing equimolecular salt of piperazine and 1,2-diphenyl-4-butyl-3,5-dioxo pyrazolidine
KR940003292B1 (ko)	1994-04-20	광학적 활성 2-메틸-1-(4-트리플루오로메틸페닐)-3-피롤리디노-1-프로파논 및 그 제조방법
US3546208A (en)	1970-12-08	Proscillaridin ketals
US3079402A (en)	1963-02-26	Cero-chromonamino compounds
KR950005737B1 (ko)	1995-05-30	징코라이드 혼합물로부터 단성분의 분리방법
FR2508032A1 (fr)	1982-12-24	Nouveaux derives amino-3 aryloxymethyl-2 propanol-1, leur procede de preparation et leurs applications en therapeutique
CN117946122A (zh)	2024-04-30	一种螺环哌嗪氧化吲哚类化合物及其制备方法
US3183246A (en)	1965-05-11	1, 1-dioxothienylcarbamates
US3446821A (en)	1969-05-27	Intermediates useful in preparation of butenolides and process therefor
JPS60199887A (ja)	1985-10-09	５−フルオロウラシル誘導体、その製造法及び腫瘍抑制剤

JPH0437832B2 - - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=12913698

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

Also Published As

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