JPH0156065B2 - - Google Patents
Info
- Publication number
- JPH0156065B2 JPH0156065B2 JP4473785A JP4473785A JPH0156065B2 JP H0156065 B2 JPH0156065 B2 JP H0156065B2 JP 4473785 A JP4473785 A JP 4473785A JP 4473785 A JP4473785 A JP 4473785A JP H0156065 B2 JPH0156065 B2 JP H0156065B2
- Authority
- JP
- Japan
- Prior art keywords
- drug
- compound
- group
- general formula
- present
- 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.)
- Expired
Links
- -1 benzoyl urea compound Chemical class 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 25
- 239000003814 drug Substances 0.000 description 24
- 229940079593 drug Drugs 0.000 description 24
- 230000001093 anti-cancer Effects 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 230000004083 survival effect Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 8
- 201000011510 cancer Diseases 0.000 description 8
- 238000001647 drug administration Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 238000007912 intraperitoneal administration Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZZTXGLBRQLEFLX-UHFFFAOYSA-N 2-nitrobenzoyl isocyanate Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)N=C=O ZZTXGLBRQLEFLX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000002054 transplantation Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CFWIOOCJVYJEID-UHFFFAOYSA-N 3-amino-2-chlorophenol Chemical compound NC1=CC=CC(O)=C1Cl CFWIOOCJVYJEID-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- OQPORDRGBPPVJX-UHFFFAOYSA-N 3-chloro-4-(5-chloropyrimidin-2-yl)oxyaniline Chemical compound ClC1=CC(N)=CC=C1OC1=NC=C(Cl)C=N1 OQPORDRGBPPVJX-UHFFFAOYSA-N 0.000 description 1
- WAKXDNJQNFKVJB-UHFFFAOYSA-N 4-(5-bromopyrimidin-2-yl)oxy-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1OC1=NC=C(Br)C=N1 WAKXDNJQNFKVJB-UHFFFAOYSA-N 0.000 description 1
- ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 description 1
- XPGIBDJXEVAVTO-UHFFFAOYSA-N 5-bromo-2-chloropyrimidine Chemical compound ClC1=NC=C(Br)C=N1 XPGIBDJXEVAVTO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 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 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- ZNXMULRAAGIRAL-UHFFFAOYSA-N n-[[3-chloro-4-(5-chloropyrimidin-2-yl)oxyphenyl]carbamoyl]-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NC(=O)NC(C=C1Cl)=CC=C1OC1=NC=C(Cl)C=N1 ZNXMULRAAGIRAL-UHFFFAOYSA-N 0.000 description 1
- IUVXRLRTGJNDIX-UHFFFAOYSA-N n-[[3-chloro-4-(5-iodopyrimidin-2-yl)oxyphenyl]carbamoyl]-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NC(=O)NC(C=C1Cl)=CC=C1OC1=NC=C(I)C=N1 IUVXRLRTGJNDIX-UHFFFAOYSA-N 0.000 description 1
- PSEJEBZWLNYNTB-UHFFFAOYSA-N n-[[3-chloro-4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]carbamoyl]-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NC(=O)NC(C=C1Cl)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 PSEJEBZWLNYNTB-UHFFFAOYSA-N 0.000 description 1
- WKXWMGOTZJGIIK-UHFFFAOYSA-N n-[[4-(5-bromopyrimidin-2-yl)oxy-3-chlorophenyl]carbamoyl]-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NC(=O)NC(C=C1Cl)=CC=C1OC1=NC=C(Br)C=N1 WKXWMGOTZJGIIK-UHFFFAOYSA-N 0.000 description 1
- ZYRQUYCVZFSMPZ-UHFFFAOYSA-N n-phenyl-n-(pyridin-2-yloxycarbamoyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)N(C=1C=CC=CC=1)C(=O)NOC1=CC=CC=N1 ZYRQUYCVZFSMPZ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60044737A JPS61205257A (ja) | 1985-03-08 | 1985-03-08 | ベンゾイルウレア系化合物、その製法及びそれを含有する抗ガン剤 |
| NZ214953A NZ214953A (en) | 1985-02-20 | 1986-01-28 | Pyrimidinyloxy-phenyl ureas; intermediates and pharmaceutical compositions |
| US06/823,521 US4727077A (en) | 1985-02-20 | 1986-01-29 | Benzoyl urea compounds, process for their production, and antitumorous compositions containing them |
| US06/824,088 US4849425A (en) | 1985-02-20 | 1986-01-30 | Readily absorbable pharmaceutical composition |
| GB08602792A GB2171695B (en) | 1985-02-20 | 1986-02-05 | Benzoyl urea compounds, process for their production, and antitumorous compositions containing them |
| AU53285/86A AU593233B2 (en) | 1985-02-20 | 1986-02-06 | Benzoyl urea compounds, process for their production and antitumorous compositions containing them |
| CA000501576A CA1266473A (en) | 1985-02-20 | 1986-02-11 | Benzoyl urea compounds, useful as anti-tumor drugs |
| CA000501662A CA1260396A (en) | 1985-02-20 | 1986-02-12 | Readily absorbable pharmaceutical composition |
| AR30315286A AR240557A1 (es) | 1985-02-20 | 1986-02-17 | Procedimiento para preparar compuestos de benzoil urea e intermedarios para uso exclusivo en dicho procedimiento |
| FR8602147A FR2577551B1 (fr) | 1985-02-20 | 1986-02-18 | Derives de benzoyl uree, procede pour les preparer, et compositions antitumorales les contenant |
| EP86102063A EP0192235B1 (en) | 1985-02-20 | 1986-02-18 | Benzoyl urea compounds, process for their production, and antitumorous compositions containing them |
| CH642/86A CH671576A5 (zh) | 1985-02-20 | 1986-02-18 | |
| DE8686102063T DE3667055D1 (en) | 1985-02-20 | 1986-02-18 | Benzoyl urea compounds, process for their production, and antitumorous compositions containing them |
| DD86287134A DD243025A5 (de) | 1985-03-08 | 1986-02-18 | Verfahren zur herstellung von benzoylharnstoff-verbindungen |
| ES552191A ES8707506A1 (es) | 1985-02-20 | 1986-02-19 | Un procedimiento para la produccion de un compuesto de benzoilurea |
| KR1019860001154A KR930004676B1 (ko) | 1985-02-20 | 1986-02-19 | 벤조일우레아 화합물의 제조방법 |
| SU864023808A SU1500156A3 (ru) | 1985-02-20 | 1986-02-19 | Способ получени производных бензоилмочевины |
| CN86101087A CN1013196B (zh) | 1985-02-20 | 1986-02-19 | 苯甲酰脲类化合物的制备方法 |
| EP86102217A EP0192263B1 (en) | 1985-02-20 | 1986-02-20 | Readily absorbable pharmaceutical composition |
| DK080286A DK163124C (da) | 1985-02-20 | 1986-02-20 | N-benzoyl-n'-pyrimidinyloxyphenylurinstofforbindelser, fremgangsmaade til fremstilling heraf samt antitumorpraeparater indeholdende forbindelserne |
| DE8686102217T DE3686177T2 (de) | 1985-02-20 | 1986-02-20 | Gut absorbierende pharmazeutische zusammensetzungen. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60044737A JPS61205257A (ja) | 1985-03-08 | 1985-03-08 | ベンゾイルウレア系化合物、その製法及びそれを含有する抗ガン剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61205257A JPS61205257A (ja) | 1986-09-11 |
| JPH0156065B2 true JPH0156065B2 (zh) | 1989-11-28 |
Family
ID=12699756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60044737A Granted JPS61205257A (ja) | 1985-02-20 | 1985-03-08 | ベンゾイルウレア系化合物、その製法及びそれを含有する抗ガン剤 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS61205257A (zh) |
| DD (1) | DD243025A5 (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02196719A (ja) * | 1989-01-24 | 1990-08-03 | Green Cross Corp:The | 粉末状医薬組成物 |
| NZ701237A (en) * | 2010-03-19 | 2016-04-29 | Boston Biomedical Inc | Novel compounds and compositions for targeting cancer stem cells |
| TWI505828B (zh) * | 2010-12-20 | 2015-11-01 | 葛蘭素史克智慧財產（第二）有限公司 | 新穎醫藥組成物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5731664A (en) * | 1980-07-30 | 1982-02-20 | Ishihara Sangyo Kaisha Ltd | N-benzoyl-n'-pyridyloxyphenylurea derivative |
| JPS57109721A (en) * | 1980-12-27 | 1982-07-08 | Ishihara Sangyo Kaisha Ltd | Carcinostatic agent |
-
1985
- 1985-03-08 JP JP60044737A patent/JPS61205257A/ja active Granted
-
1986
- 1986-02-18 DD DD86287134A patent/DD243025A5/de not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5731664A (en) * | 1980-07-30 | 1982-02-20 | Ishihara Sangyo Kaisha Ltd | N-benzoyl-n'-pyridyloxyphenylurea derivative |
| JPS57109721A (en) * | 1980-12-27 | 1982-07-08 | Ishihara Sangyo Kaisha Ltd | Carcinostatic agent |
Also Published As
| Publication number | Publication date |
|---|---|
| DD243025A5 (de) | 1987-02-18 |
| JPS61205257A (ja) | 1986-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |