SE436208B - Sett att framstella 5-fluoro-uracilderivat - Google Patents

Sett att framstella 5-fluoro-uracilderivat

Info

Publication number: SE436208B
Authority: SE; Sweden
Prior art keywords: compound; fluoro; administered; fluorouracil; control
Prior art date: 1976-12-24

Application number

SE7714670A

Other languages

English (en)

Swedish (sv)

Other versions

SE7714670L (sv

Inventor

S Kijima

H Shionoya

K Hamamura

H Arai

N Koyanagi

Original Assignee

Eisai 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.)

1976-12-24

Filing date

1977-12-22

Publication date

1984-11-19

1977-12-22 Application filed by Eisai Co Ltd filed Critical Eisai Co Ltd

1978-06-25 Publication of SE7714670L publication Critical patent/SE7714670L/

1984-11-19 Publication of SE436208B publication Critical patent/SE436208B/sv

Links

GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical class FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 title claims description 37
229960002949 fluorouracil Drugs 0.000 claims description 41
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
238000000034 method Methods 0.000 claims description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
150000001447 alkali salts Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
GZCJJOLJSBCUNR-UHFFFAOYSA-N chroman-6-ol Chemical class O1CCCC2=CC(O)=CC=C21 GZCJJOLJSBCUNR-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
229940126062 Compound A Drugs 0.000 description 31
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 31
WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 20
238000002513 implantation Methods 0.000 description 18
239000000243 solution Substances 0.000 description 15
230000004083 survival effect Effects 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
239000000126 substance Substances 0.000 description 11
241000699670 Mus sp. Species 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
230000000259 anti-tumor effect Effects 0.000 description 9
235000002639 sodium chloride Nutrition 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
230000000694 effects Effects 0.000 description 7
239000000203 mixture Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
208000032839 leukemia Diseases 0.000 description 6
235000012424 soybean oil Nutrition 0.000 description 6
239000003549 soybean oil Substances 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 5
229920002261 Corn starch Polymers 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
230000007059 acute toxicity Effects 0.000 description 4
231100000403 acute toxicity Toxicity 0.000 description 4
239000002246 antineoplastic agent Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
101100005765 Arabidopsis thaliana CDF1 gene Proteins 0.000 description 3
101100007579 Arabidopsis thaliana CPP1 gene Proteins 0.000 description 3
229920000168 Microcrystalline cellulose Polymers 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
229940016286 microcrystalline cellulose Drugs 0.000 description 3
235000019813 microcrystalline cellulose Nutrition 0.000 description 3
239000008108 microcrystalline cellulose Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
230000004614 tumor growth Effects 0.000 description 3
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
244000020518 Carthamus tinctorius Species 0.000 description 2
235000003255 Carthamus tinctorius Nutrition 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
206010058467 Lung neoplasm malignant Diseases 0.000 description 2
235000019759 Maize starch Nutrition 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
208000002495 Uterine Neoplasms Diseases 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
229940099112 cornstarch Drugs 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000003630 growth substance Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
201000005202 lung cancer Diseases 0.000 description 2
208000020816 lung neoplasm Diseases 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
231100000816 toxic dose Toxicity 0.000 description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
206010046766 uterine cancer Diseases 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
206010005003 Bladder cancer Diseases 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
102100034068 Monocarboxylate transporter 1 Human genes 0.000 description 1
108700038057 Monocarboxylate transporter 1 Proteins 0.000 description 1
208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
208000006268 Sarcoma 180 Diseases 0.000 description 1
201000010208 Seminoma Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
208000005718 Stomach Neoplasms Diseases 0.000 description 1
208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
229940041181 antineoplastic drug Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229960005069 calcium Drugs 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
238000002648 combination therapy Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
206010017758 gastric cancer Diseases 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000012010 growth Effects 0.000 description 1
206010073071 hepatocellular carcinoma Diseases 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229960001375 lactose Drugs 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
208000025036 lymphosarcoma Diseases 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
201000011549 stomach cancer Diseases 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000005457 triglyceride group Chemical group 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
201000005112 urinary bladder cancer Diseases 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000004804 winding Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SE7714670A 1976-12-24 1977-12-22 Sett att framstella 5-fluoro-uracilderivat SE436208B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP51154941A JPS6052708B2 (ja)	1976-12-24	1976-12-24	５−フルオロウラシル系化合物およびそれを含有する抗腫瘍剤

Publications (2)

Publication Number	Publication Date
SE7714670L SE7714670L (sv)	1978-06-25
SE436208B true SE436208B (sv)	1984-11-19

Family

ID=15595270

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7714670A SE436208B (sv)	1976-12-24	1977-12-22	Sett att framstella 5-fluoro-uracilderivat

Country Status (14)

Country	Link
US (1)	US4130648A (fr)
JP (1)	JPS6052708B2 (fr)
AU (1)	AU519524B2 (fr)
BE (1)	BE862213A (fr)
CA (1)	CA1077483A (fr)
CH (1)	CH636874A5 (fr)
DE (1)	DE2757431A1 (fr)
ES (1)	ES465406A1 (fr)
FR (1)	FR2378779A1 (fr)
GB (1)	GB1594840A (fr)
NL (1)	NL7714205A (fr)
PH (1)	PH12700A (fr)
SE (1)	SE436208B (fr)
SU (2)	SU827489A1 (fr)

Families Citing this family (7)

* 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
US4727077A (en) *	1985-02-20	1988-02-23	Ishihara Sangyo Kaisha Ltd.	Benzoyl urea compounds, process for their production, and antitumorous compositions containing them
DK197486A (da) *	1986-04-30	1987-10-31	Ferring Farma Lab	5-fluoruracilprodug
RU2191581C1 (ru) *	2001-11-16	2002-10-27	Нестерук Владимир Викторович	Способ получения раствора фторурацила
US11584733B2 (en)	2017-01-09	2023-02-21	Shuttle Pharmaceuticals, Inc.	Selective histone deacetylase inhibitors for the treatment of human disease
ES2914123T3 (es)	2017-01-09	2022-06-07	Shuttle Pharmaceuticals Inc	Inhibidores selectivos de la histona desacetilasa para el tratamiento de una enfermedad humana
CN112004537A (zh)	2018-01-09	2020-11-27	穿梭药业公司	用于治疗人疾病的选择性组蛋白去乙酰化酶抑制剂

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5324952B2 (fr) *	1973-11-28	1978-07-24

1976
- 1976-12-24 JP JP51154941A patent/JPS6052708B2/ja not_active Expired
1977
- 1977-12-14 US US05/860,319 patent/US4130648A/en not_active Expired - Lifetime
- 1977-12-20 FR FR7738495A patent/FR2378779A1/fr active Granted
- 1977-12-21 AU AU31825/77A patent/AU519524B2/en not_active Expired
- 1977-12-21 CH CH1581377A patent/CH636874A5/de not_active IP Right Cessation
- 1977-12-21 NL NL7714205A patent/NL7714205A/xx not_active Application Discontinuation
- 1977-12-22 DE DE19772757431 patent/DE2757431A1/de not_active Withdrawn
- 1977-12-22 BE BE183769A patent/BE862213A/fr not_active IP Right Cessation
- 1977-12-22 SE SE7714670A patent/SE436208B/sv not_active IP Right Cessation
- 1977-12-22 GB GB53541/77A patent/GB1594840A/en not_active Expired
- 1977-12-23 PH PH20592A patent/PH12700A/en unknown
- 1977-12-23 ES ES465406A patent/ES465406A1/es not_active Expired
- 1977-12-23 CA CA293,822A patent/CA1077483A/fr not_active Expired
- 1977-12-23 SU SU772559705A patent/SU827489A1/ru active
1979
- 1979-06-18 SU SU792778129A patent/SU795469A3/ru active

Also Published As

Publication number	Publication date
BE862213A (fr)	1978-04-14
PH12700A (en)	1979-07-20
SU827489A1 (ru)	1981-05-07
FR2378779A1 (fr)	1978-08-25
SE7714670L (sv)	1978-06-25
US4130648A (en)	1978-12-19
NL7714205A (nl)	1978-06-27
JPS6052708B2 (ja)	1985-11-20
AU519524B2 (en)	1981-12-10
SU795469A3 (ru)	1981-01-07
ES465406A1 (es)	1978-09-16
FR2378779B1 (fr)	1980-08-22
GB1594840A (en)	1981-08-05
DE2757431A1 (de)	1978-06-29
AU3182577A (en)	1979-06-28
JPS5379880A (en)	1978-07-14
CA1077483A (fr)	1980-05-13
CH636874A5 (de)	1983-06-30

Legal Events

Date

Code

Title

Description

1995-01-31

NUG

Patent has lapsed

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Effective date: 19880927

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