JPS61246171A - ベンゾオキサジン誘導体 - Google Patents
ベンゾオキサジン誘導体Info
- Publication number
- JPS61246171A JPS61246171A JP18763785A JP18763785A JPS61246171A JP S61246171 A JPS61246171 A JP S61246171A JP 18763785 A JP18763785 A JP 18763785A JP 18763785 A JP18763785 A JP 18763785A JP S61246171 A JPS61246171 A JP S61246171A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound expressed
- methyl
- dihydro
- difluoro
- 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
- 150000005130 benzoxazines Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- BVHSAZFNVBBGNX-UHFFFAOYSA-N 7,8-difluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC(F)=C(F)C2=C1NC(C)CO2 BVHSAZFNVBBGNX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 7
- 239000002904 solvent Substances 0.000 abstract description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 6
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007868 Raney catalyst Substances 0.000 abstract description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000564 Raney nickel Inorganic materials 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- 229960001699 ofloxacin Drugs 0.000 abstract description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 abstract description 2
- 208000036366 Sensation of pressure Diseases 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- -1 inorganic acid salt Chemical class 0.000 description 4
- ARCACZWMYGILNI-UHFFFAOYSA-N 1,2,3-trifluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1F ARCACZWMYGILNI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-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
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KEGOHDCHURMFKX-UHFFFAOYSA-N 2,3-difluoro-6-nitrophenol Chemical compound OC1=C(F)C(F)=CC=C1[N+]([O-])=O KEGOHDCHURMFKX-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102100033636 Histone H3.2 Human genes 0.000 description 1
- 101000871895 Homo sapiens Histone H3.2 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18763785A JPS61246171A (ja) | 1985-08-27 | 1985-08-27 | ベンゾオキサジン誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18763785A JPS61246171A (ja) | 1985-08-27 | 1985-08-27 | ベンゾオキサジン誘導体 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17162181A Division JPS5872588A (ja) | 1981-10-27 | 1981-10-27 | ピリド〔１，２，３−ｄｅ〕−１，４−ベンゾオキサジン誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61246171A true JPS61246171A (ja) | 1986-11-01 |
| JPH0158186B2 JPH0158186B2 (enrdf_load_stackoverflow) | 1989-12-11 |
Family
ID=16209597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18763785A Granted JPS61246171A (ja) | 1985-08-27 | 1985-08-27 | ベンゾオキサジン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61246171A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63264468A (ja) * | 1986-12-25 | 1988-11-01 | Dai Ichi Seiyaku Co Ltd | 光学活性ベンゾオキサジン |
-
1985
- 1985-08-27 JP JP18763785A patent/JPS61246171A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63264468A (ja) * | 1986-12-25 | 1988-11-01 | Dai Ichi Seiyaku Co Ltd | 光学活性ベンゾオキサジン |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0158186B2 (enrdf_load_stackoverflow) | 1989-12-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR840002141B1 (ko) | 벤즈옥사진 유도체의 제조방법 | |
| EP1664004B1 (de) | Verfahren zur herstellung von 4-(4-aminophenyl)-3-morpholinon | |
| Perez-Medina et al. | The Preparation and Reactions of Some Polysubstituted Pyridines. 2-Methyl-3-hydroxy-5-hydroxymethylpyridine (4-Deshydroxymethylpyridoxin) | |
| JPH0692371B2 (ja) | 新規複素環誘導体、その製法およびこれらを含有し、アルド−ス還元酵素抑制剤として特に有用な医薬の製法 | |
| Vaughan et al. | Triazolo and imidiazopyridines | |
| JPS61246171A (ja) | ベンゾオキサジン誘導体 | |
| JPS591489A (ja) | ピリドベンゾオキサジン誘導体 | |
| Loudon et al. | 2: 3-Dihydro-3-oxobenz-1: 4-oxazines | |
| US3352877A (en) | Process for preparing 5-halo-2-aminophenyl-3-aryl ketones | |
| JPS61246151A (ja) | アセトニルオキシニトロベンゼン誘導体 | |
| ELDERFIELD et al. | SYNTHESIS OF 1-AMINOPHENAZINES AND CONVERSION OF THEM TO POTENTIAL ANTIMALARIALS1 | |
| JPS61246188A (ja) | ピリド−１，４−ベンゾオキサジン誘導体 | |
| JPH02223542A (ja) | ヒドロアトロパ酸誘導体およびそのエステルの製造方法 | |
| JPS621953B2 (enrdf_load_stackoverflow) | ||
| CN111196770B (zh) | 一种溴芬酸钠的简便制备方法 | |
| Den Otter | The preparation of symmetric and asymmetric aminopropanediol and of some of their derivatives | |
| Bon et al. | The synthesis of 2-substituted imino-3-amino-4-thiazolidones | |
| JPH04169583A (ja) | フェノチアジン誘導体およびその製造方法 | |
| CLAPP et al. | Properties of dinitroölefins: Reactions with bases, chlorine, and hydrogen | |
| JPH0153861B2 (enrdf_load_stackoverflow) | ||
| US2302903A (en) | Pyridine dicarboxylic acids | |
| FRISCH et al. | THE SEARCH FOR SUPERIOR ANTIMALARIALS. I. EXPERIMENTS IN THE VERATROLE GROUP1 | |
| JPS63264468A (ja) | 光学活性ベンゾオキサジン | |
| JPS61246172A (ja) | ベンゾオキサジニルマロン酸誘導体 | |
| Skinner et al. | Benzoylcyanamide from Ethyl Benzoylthioncarbamate |