JPH0149272B2 - - Google Patents
Info
- Publication number
- JPH0149272B2 JPH0149272B2 JP17674582A JP17674582A JPH0149272B2 JP H0149272 B2 JPH0149272 B2 JP H0149272B2 JP 17674582 A JP17674582 A JP 17674582A JP 17674582 A JP17674582 A JP 17674582A JP H0149272 B2 JPH0149272 B2 JP H0149272B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- benzoxazine
- dihydro
- oxo
- pyrido
- 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
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 229910015900 BF3 Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000013522 chelant Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- NVKWWNNJFKZNJO-UHFFFAOYSA-N 82419-35-0 Chemical compound O1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=C(F)C(F)=C3 NVKWWNNJFKZNJO-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- CHNLPLHJUPMEOI-UHFFFAOYSA-N oxolane;trifluoroborane Chemical compound FB(F)F.C1CCOC1 CHNLPLHJUPMEOI-UHFFFAOYSA-N 0.000 description 5
- XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- CFLBIADORGSMCX-UHFFFAOYSA-N 2h-1,4-benzoxazine-6-carboxylic acid Chemical compound O1CC=NC2=CC(C(=O)O)=CC=C21 CFLBIADORGSMCX-UHFFFAOYSA-N 0.000 description 2
- QDEJGQKJMKXYLM-UHFFFAOYSA-N 2h-pyrido[2,3-h][1,2]benzoxazine Chemical class C1=CC2=NC=CC=C2C2=C1C=CNO2 QDEJGQKJMKXYLM-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- TZSXJUSNOOBBOP-UHFFFAOYSA-N ac1mwmhd Chemical compound CC1COC2=C(F)C(F)=CC3=C2N1C=C(C(=O)OCC)C3=O TZSXJUSNOOBBOP-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- RROQSCBOBBLOOA-UHFFFAOYSA-N C(C)OC(=O)C=1C=CC2=C(C=CNO2)C1 Chemical compound C(C)OC(=O)C=1C=CC2=C(C=CNO2)C1 RROQSCBOBBLOOA-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17674582A JPS5967290A (ja) | 1982-10-07 | 1982-10-07 | ピリドベンズオキサジン誘導体の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17674582A JPS5967290A (ja) | 1982-10-07 | 1982-10-07 | ピリドベンズオキサジン誘導体の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5967290A JPS5967290A (ja) | 1984-04-16 |
| JPH0149272B2 true JPH0149272B2 (en]) | 1989-10-24 |
Family
ID=16019057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17674582A Granted JPS5967290A (ja) | 1982-10-07 | 1982-10-07 | ピリドベンズオキサジン誘導体の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5967290A (en]) |
-
1982
- 1982-10-07 JP JP17674582A patent/JPS5967290A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5967290A (ja) | 1984-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0240066B2 (en]) | ||
| JPH07501835A (ja) | オフロキサジン，レボフロキサジン及び誘導体の合成に使用されるベンゾキサジンの製造法 | |
| CA1123833A (en) | Process for the manufacture of polyalkyl-1-oxa-diaza-oxo-spirodecanes | |
| CS264345B2 (en) | Process for preparing quinolincarboxylic acids | |
| JPH0149272B2 (en]) | ||
| EP0273399B1 (en) | Optically active 2,3-dihydrobenzoaxine derivatives and process for preparing the same | |
| JP2979358B2 (ja) | フェノチアジン誘導体 | |
| CA2276320C (en) | L-tartrate of trans-(-)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine compound and process for preparing the same | |
| JPH0372073B2 (en]) | ||
| JPH0215554B2 (en]) | ||
| JP2549931B2 (ja) | ピリミドベンズイミダゾール誘導体 | |
| JPH0148910B2 (en]) | ||
| JPH0214356B2 (en]) | ||
| JPH04169583A (ja) | フェノチアジン誘導体およびその製造方法 | |
| JPH0332552B2 (en]) | ||
| JP2527769B2 (ja) | キサンチン誘導体およびその製造方法 | |
| JPH0475239B2 (en]) | ||
| EP0199485B1 (en) | Intermediates and process | |
| JPS62294689A (ja) | キノリン−３−カルボン酸誘導体 | |
| JPH0150709B2 (en]) | ||
| JP3454435B2 (ja) | ４−アミノピリジン誘導体の製造方法 | |
| KR0132189B1 (ko) | (-)-3(s)-메틸피리도벤즈옥사진 카르복실산 유도체의 제조방법 | |
| JP2552101B2 (ja) | 新規ピリドンカルボン酸誘導体及びその調製方法 | |
| US6333414B1 (en) | Process for the synthesis of trisubstituted oxazoles | |
| JPH0359904B2 (en]) |