JPS58225092A - ピリド〔１，２，３−ｄｅ〕〔１，４〕ベンゾオキサジン−６−カルボン酸誘導体 - Google Patents
ピリド〔１，２，３−ｄｅ〕〔１，４〕ベンゾオキサジン−６−カルボン酸誘導体Info
- Publication number
- JPS58225092A JPS58225092A JP10918182A JP10918182A JPS58225092A JP S58225092 A JPS58225092 A JP S58225092A JP 10918182 A JP10918182 A JP 10918182A JP 10918182 A JP10918182 A JP 10918182A JP S58225092 A JPS58225092 A JP S58225092A
- Authority
- JP
- Japan
- Prior art keywords
- pyrido
- benzoxazine
- carboxylic acid
- dihydro
- oxo
- 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
- XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical class O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- CFLBIADORGSMCX-UHFFFAOYSA-N 2h-1,4-benzoxazine-6-carboxylic acid Chemical class O1CC=NC2=CC(C(=O)O)=CC=C21 CFLBIADORGSMCX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 8
- -1 bicyclic amine Chemical class 0.000 abstract description 5
- 241000894006 Bacteria Species 0.000 abstract description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 239000002798 polar solvent Substances 0.000 abstract description 2
- CLAOJJNNKVPOPT-UHFFFAOYSA-N 7-fluoro-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13),11-tetraene-11-carboxylic acid Chemical class C1COC2=CC(F)=CC3=C2N1C=C(C(=O)O)C3=O CLAOJJNNKVPOPT-UHFFFAOYSA-N 0.000 abstract 1
- 241000192125 Firmicutes Species 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- FOMVTXNAHHOMJK-UHFFFAOYSA-N 2,3,4,4a,5,6,7,8-octahydro-1h-pyrido[1,2-b]pyridazine Chemical compound N1CCCC2CCCCN21 FOMVTXNAHHOMJK-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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 description 1
- 229960001732 pipemidic acid Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 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 |
|---|---|---|---|
| JP10918182A JPS58225092A (ja) | 1982-06-25 | 1982-06-25 | ピリド〔１，２，３−ｄｅ〕〔１，４〕ベンゾオキサジン−６−カルボン酸誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10918182A JPS58225092A (ja) | 1982-06-25 | 1982-06-25 | ピリド〔１，２，３−ｄｅ〕〔１，４〕ベンゾオキサジン−６−カルボン酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58225092A true JPS58225092A (ja) | 1983-12-27 |
| JPH0355477B2 JPH0355477B2 (enrdf_load_stackoverflow) | 1991-08-23 |
Family
ID=14503700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10918182A Granted JPS58225092A (ja) | 1982-06-25 | 1982-06-25 | ピリド〔１，２，３−ｄｅ〕〔１，４〕ベンゾオキサジン−６−カルボン酸誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58225092A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0159174B1 (en) * | 1984-04-16 | 1991-10-23 | Warner-Lambert Company | Substituted naphthyridine-, quinoline- and benzoxazine- carboxylic acids as antibacterial agents and processes for their production |
| WO2009131973A1 (en) * | 2008-04-23 | 2009-10-29 | Janssen Pharmaceutica Nv | Quinolone derivatives useful as antibacterial agents |
| CN109251211A (zh) * | 2016-12-21 | 2019-01-22 | 广东省中医院（广州中医药大学第二附属医院、广州中医药大学第二临床医学院、广东省中医药科学院） | 一类喹诺酮羧酸化合物及其中间体、制备方法以及应用 |
-
1982
- 1982-06-25 JP JP10918182A patent/JPS58225092A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0159174B1 (en) * | 1984-04-16 | 1991-10-23 | Warner-Lambert Company | Substituted naphthyridine-, quinoline- and benzoxazine- carboxylic acids as antibacterial agents and processes for their production |
| WO2009131973A1 (en) * | 2008-04-23 | 2009-10-29 | Janssen Pharmaceutica Nv | Quinolone derivatives useful as antibacterial agents |
| CN109251211A (zh) * | 2016-12-21 | 2019-01-22 | 广东省中医院（广州中医药大学第二附属医院、广州中医药大学第二临床医学院、广东省中医药科学院） | 一类喹诺酮羧酸化合物及其中间体、制备方法以及应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0355477B2 (enrdf_load_stackoverflow) | 1991-08-23 |
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