JPH0428266B2 - - Google Patents
Info
- Publication number
- JPH0428266B2 JPH0428266B2 JP9333386A JP9333386A JPH0428266B2 JP H0428266 B2 JPH0428266 B2 JP H0428266B2 JP 9333386 A JP9333386 A JP 9333386A JP 9333386 A JP9333386 A JP 9333386A JP H0428266 B2 JPH0428266 B2 JP H0428266B2
- Authority
- JP
- Japan
- Prior art keywords
- quinazolinone
- phenyl
- following formula
- formula
- represented
- 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 quinazolinone compound Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 4
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 4
- FQQLGGVOVRCRBE-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethenyl]-3-phenylquinazolin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C=CC1=NC2=CC=CC=C2C(=O)N1C1=CC=CC=C1 FQQLGGVOVRCRBE-UHFFFAOYSA-N 0.000 description 4
- LGNHCOKGKIUFDW-UHFFFAOYSA-N 2-methyl-3-phenylquinazolin-4-one Chemical compound CC1=NC2=CC=CC=C2C(=O)N1C1=CC=CC=C1 LGNHCOKGKIUFDW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000398 anti-amebic effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 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
- 238000000034 method Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9333386A JPS62252778A (ja) | 1986-04-24 | 1986-04-24 | 新規キナゾリノン化合物およびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9333386A JPS62252778A (ja) | 1986-04-24 | 1986-04-24 | 新規キナゾリノン化合物およびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62252778A JPS62252778A (ja) | 1987-11-04 |
| JPH0428266B2 true JPH0428266B2 (cs) | 1992-05-13 |
Family
ID=14079340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9333386A Granted JPS62252778A (ja) | 1986-04-24 | 1986-04-24 | 新規キナゾリノン化合物およびその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62252778A (cs) |
-
1986
- 1986-04-24 JP JP9333386A patent/JPS62252778A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62252778A (ja) | 1987-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2004074264A1 (ja) | キナゾリンジオン骨格を有するフェニルアラニン誘導体の製造方法及び製造中間体 | |
| JPS61251650A (ja) | （ｚ）−１−フエニル−１−ジエチルアミノカルボニル−２−アミノメチルシクロプロパン塩酸塩の製造方法 | |
| JPH1171351A (ja) | 置換キノロン誘導体及びこれを含有する医薬 | |
| JPH0148911B2 (cs) | ||
| JPH0615527B2 (ja) | アルキルジアミン誘導体、その製造法および抗不整脈剤 | |
| SU722481A3 (ru) | Способ получени производных аминокетона или их солей | |
| CN107698571B (zh) | 萘酰亚胺-香豆素类dna靶向双嵌入剂及其合成和应用 | |
| JPH0428266B2 (cs) | ||
| JPH07108904B2 (ja) | 新規なアシルベンゾキサゾリノン類、及びその製造法 | |
| JPS63165362A (ja) | 置換アミノチメル−５，６，７，８−テトラヒドロナフチルオキシ酢酸類、中間体類、それらの製造法および薬物におけるそれらの使用 | |
| RU2708243C1 (ru) | Способ получения фенилаланинового соединения | |
| JPH0584314B2 (cs) | ||
| RU2155765C2 (ru) | Производные 1,4-дигидропиридина с циклическим мостиком в положениях 1,2 в форме смеси их изомеров | |
| JPH0121828B2 (cs) | ||
| JPS61197558A (ja) | 新規なキナルジン酸アミド誘導体およびその製造法 | |
| JPS6310955B2 (cs) | ||
| JP2002540109A (ja) | 形態ａと指定された結晶変態のメシル酸ドキサゾシンの新規な調製方法 | |
| CN110317171A (zh) | 4-二硫代甲酸哌嗪-1,8-萘酰亚胺衍生物及其制备方法和应用 | |
| JPH041746B2 (cs) | ||
| JPH01110676A (ja) | キナゾリノン化合物の製造方法 | |
| JP3037980B2 (ja) | ベンゾピラン誘導体 | |
| JP2809972B2 (ja) | ５−トリフルオロメチルウラシルの製造法 | |
| JPS60246384A (ja) | クロモン−８−カルポキサミド誘導体 | |
| KR800001248B1 (ko) | 1-알킬-2-(페녹시메틸)-5-니트로-이미다졸의 제조방법 | |
| JP2563864B2 (ja) | ２−（３，４−ジメトキシスチリル）−３，１−ベンゾオキサジン−４−オンの製造方法 |