JPS6092217A - フルオロデオキシウリジン誘導体とチミジンとを含有する抗腫瘍剤 - Google Patents
フルオロデオキシウリジン誘導体とチミジンとを含有する抗腫瘍剤Info
- Publication number
- JPS6092217A JPS6092217A JP20177883A JP20177883A JPS6092217A JP S6092217 A JPS6092217 A JP S6092217A JP 20177883 A JP20177883 A JP 20177883A JP 20177883 A JP20177883 A JP 20177883A JP S6092217 A JPS6092217 A JP S6092217A
- Authority
- JP
- Japan
- Prior art keywords
- group
- thymidine
- substituted
- unsubstituted
- fluorodeoxyuridine
- Prior art date
- 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.)
- Granted
Links
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 title claims abstract description 46
- 229940104230 thymidine Drugs 0.000 title claims abstract description 24
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 title claims abstract description 23
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 title claims abstract description 23
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical class C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 title claims abstract description 16
- 239000002246 antineoplastic agent Substances 0.000 title claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229940041181 antineoplastic drug Drugs 0.000 claims 2
- 101150072531 10 gene Proteins 0.000 claims 1
- 125000004989 dicarbonyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 230000001988 toxicity Effects 0.000 abstract description 23
- 231100000419 toxicity Toxicity 0.000 abstract description 23
- 230000000694 effects Effects 0.000 abstract description 15
- 210000000265 leukocyte Anatomy 0.000 abstract description 10
- 230000037396 body weight Effects 0.000 abstract description 9
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract description 6
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical class ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 230000000259 anti-tumor effect Effects 0.000 description 23
- 238000012360 testing method Methods 0.000 description 20
- 230000001225 therapeutic effect Effects 0.000 description 12
- 238000005259 measurement Methods 0.000 description 11
- -1 furobil Chemical group 0.000 description 10
- 206010028980 Neoplasm Diseases 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 208000018522 Gastrointestinal disease Diseases 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 208000010643 digestive system disease Diseases 0.000 description 5
- 231100000673 dose–response relationship Toxicity 0.000 description 5
- 208000018685 gastrointestinal system disease Diseases 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000004820 blood count Methods 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 238000013517 stratification Methods 0.000 description 4
- 231100001274 therapeutic index Toxicity 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000022534 cell killing Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 208000006268 Sarcoma 180 Diseases 0.000 description 2
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical group 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
- 230000000340 anti-metabolite Effects 0.000 description 2
- 229940100197 antimetabolite Drugs 0.000 description 2
- 239000002256 antimetabolite Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000252983 Caecum Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010015719 Exsanguination Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004534 cecum Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 230000013872 defecation Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20177883A JPS6092217A (ja) | 1983-10-26 | 1983-10-26 | フルオロデオキシウリジン誘導体とチミジンとを含有する抗腫瘍剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20177883A JPS6092217A (ja) | 1983-10-26 | 1983-10-26 | フルオロデオキシウリジン誘導体とチミジンとを含有する抗腫瘍剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6092217A true JPS6092217A (ja) | 1985-05-23 |
| JPH0456009B2 JPH0456009B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-09-07 |
Family
ID=16446783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20177883A Granted JPS6092217A (ja) | 1983-10-26 | 1983-10-26 | フルオロデオキシウリジン誘導体とチミジンとを含有する抗腫瘍剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6092217A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0588317A1 (en) * | 1992-09-17 | 1994-03-23 | Tanabe Seiyaku Co., Ltd. | Uridine derivative and process for preparing the same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56123917A (en) * | 1980-03-04 | 1981-09-29 | Funai Corp | Antiulcer composition |
| JPS5718618A (en) * | 1980-07-09 | 1982-01-30 | Taiho Yakuhin Kogyo Kk | Antitumor agent |
-
1983
- 1983-10-26 JP JP20177883A patent/JPS6092217A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56123917A (en) * | 1980-03-04 | 1981-09-29 | Funai Corp | Antiulcer composition |
| JPS5718618A (en) * | 1980-07-09 | 1982-01-30 | Taiho Yakuhin Kogyo Kk | Antitumor agent |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0588317A1 (en) * | 1992-09-17 | 1994-03-23 | Tanabe Seiyaku Co., Ltd. | Uridine derivative and process for preparing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0456009B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-09-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5839622A (ja) | 胃酸分泌抑制剤 | |
| NL8204126A (nl) | Werkwijze voor het bereiden van een farmaceutisch preparaat met locaal-anesthetische werking dat een dialylamino-2',6'acetoxylidide en/of een farmaceutisch aanvaardbaar zout daarvan bevat, alsmede de onder toepassing van deze werkwijze verkregen gevormde farmaceutische preparaten en werkwijze voor het bereiden van dialkylamino-2',6'acetoxylididen en de farmaceutisch aanvaardbare zouten daarvan. | |
| EP1031569B1 (en) | Salt of a 7-isoindolinequinolonecarboxylic acid derivative, monohydrate thereof and composition containing the same as active ingredient | |
| JPH0559119B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| KR100207356B1 (ko) | 암 전이 억제제 | |
| EP0500953B1 (en) | Antineoplastic effect potentiator and antineoplastic agent | |
| JPS6092217A (ja) | フルオロデオキシウリジン誘導体とチミジンとを含有する抗腫瘍剤 | |
| JPH029894A (ja) | ニツコマイシン誘導体とアゾールからなる抗真菌剤 | |
| US5534513A (en) | Antitumor potentiator and antitumor composition | |
| US6037357A (en) | N-benzoyl-α-alkylated azatyrosines as anticancer agents | |
| US3143469A (en) | Anti-cholesterol nicotinic acid nu-oxide | |
| JPS63104960A (ja) | α−［（フェニルメトキシ）メチル］ピリジンアルカノール誘導体 | |
| EP0315434A2 (en) | Pyridoxal hydrazone derivatives their production and use and pharmaceutical compositions containing the same | |
| JPS62919B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JP2528370B2 (ja) | 抗腫瘍剤 | |
| DE3730542A1 (de) | Arzneimittel mit einem gehalt an bestimmten 6-mercaptopurin-derivaten, verwendung dieser 6-mercaptopurin-derivate, verfahren zur herstellung der arzneimittel sowie einige neue 6-mercaptopurin-derivate und verfahren zu deren herstellung | |
| JPS6056996A (ja) | ２′―デオキシ―５―トリフルオロメチルウリジン誘導体及びそれを含有する抗腫瘍剤 | |
| JPS62158216A (ja) | 薬物の製造方法 | |
| US5182294A (en) | Imidazolyl propyl guanidine derivative and a pharmaceutical composition containing this compound | |
| JPH07101860A (ja) | 抗悪性腫瘍剤 | |
| CN117229147A (zh) | 一类3,4-二羟基苯甲酸酯化合物及其制备方法与用途 | |
| JPS6366287B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CN117229146A (zh) | 一种咖啡酸苯乙酯衍生物及其制备方法与用途 | |
| JPS60126221A (ja) | 抗腫瘍組成物 | |
| CN117247319A (zh) | 一类5,6-二羟基萘甲酸酯化合物及其制备方法与用途 |