Patent
Method for the preparation of pyrido benzoxazine derivatives
| العنوان: | Method for the preparation of pyrido benzoxazine derivatives |
|---|---|
| Patent Number: | 5,952,494 |
| تاريخ النشر: | September 14, 1999 |
| Appl. No: | 08/443,884 |
| Application Filed: | May 26, 1995 |
| مستخلص: | There is disclosed a method for the preparation of pyrido benzoxazine derivative having the following formula I, that is improved in both production coat and yield. The method comprises reacting a compound of the following general formula II with tetraalkyl ammonium fluoride or with a mixture of tetraalkyl ammonium halide and metal fluoride in an organic solvent at a reaction temperature of about 30 to about 100.degree. C. for 1 to 3 hours under stirring; and reacting the resulting solution with a metal hydroxide or a metal carboxylate dissolved in water or in a mixture of water and alcohol, for 1 to 3 hours under heat. ##STR1## wherein X is a fluorine or chlorine atom and X.sub.1 and X.sub.2 each is a halogen atom or a nitro group, R is an alkyl group containing 1 to 4 carbon atoms and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each is an alkyd group or allyl group containing 1 to 8 carbon atoms. |
| Inventors: | Kim, Youseung (Kangnam-ku, KRX); Kang, Soon Bang (Sungdong-ku, KRX); Park, Seonhee (Nowon-ku, KRX) |
| Claim: | What is claimed is |
| Claim: | 1. A method for the preparation of pyrido benzoxazine carboxylic acid derivative having the following formula I: ##STR5## wherein X is a fluorine or chlorine atom and R is an alkyl group containing 1 to 4 carbon atoms, comprising the steps of |
| Claim: | reacting a compound of the following formula II: ##STR6## wherein X is as defined above, X.sub.1 and X.sub.2 each is a halogen atom or a nitro group |
| Claim: | R is as defined above, and |
| Claim: | R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each is an alkyl group or allyl group containing 1 to 8 carbon atoms, with tetraalkyl ammonium fluoride or with a mixture of tetraalkyl ammonium halide and metal fluoride in an organic solvent at a reaction temperature of about 30 to about 100.degree. C. for 1 to 3 hours under stirring; and without isolation of the intermediate produced |
| Claim: | reacting the resulting solution with a metal hydroxide or a metal carbonate dissolved in water or in a mixture of water and alcohol, for 1 to 3 hours under heat. |
| Claim: | 2. A method for the preparation of pyrido benzoxazine carboxylic acid derivative set forth as claim 1, wherein said organic solvent is selected from a group consisting of tetrahydrofuran, acetonitrile, pyridine, dimethylformamide and dioxane. |
| Claim: | 3. A method for the preparation of pyrido benzoxazine carboxylic acid derivative set forth as claim 1, wherein said tetraalkyl ammonium fluoride is selected from a group consisting of tetramethyl ammonium fluoride, tetraethyl ammonium fluoride, and tetrabutyl ammonium fluoride. |
| Claim: | 4. A method for the preparation of pyrido benzoxazine carboxylic acid derivative set forth as claim 1, wherein said tetraalkyl ammonium halide is selected from a group consisting of tetramethyl ammonium chloride, tetramethyl ammonium bromide, tetramethyl ammonium iodide, tetraethyl ammonium chloride, tetraethyl ammonium bromide, tetraethyl ammonium iodide, tetrapropyl ammonium chloride, tetrabutyl ammonium bromide, tetrabutyl ammonium iodide, tetrapentyl ammonium bromide, and tetrapentyl ammonium iodide. |
| Claim: | 5. A method for the preparation of pyrido benzoxazine carboxylic acid derivative set forth as claim 1, wherein said metal fluoride is selected from a group consisting of cesium fluoride, potassium fluoride, calcium fluoride and sodium fluoride. |
| Claim: | 6. A method for the preparation of pyrido benzoxazine carboxylic acid derivative set forth as claim 1, wherein said metal hydroxide is selected from a group consisting of calcium hydroxide, sodium hydroxide, potassium hydroxide and lithium hydroxide, and said metal carbonate is selected from a group consisting of potassium carbonate, sodium carbonate, lithium carbonate and barium carbonate. |
| Current U.S. Class: | 544/101 |
| Current International Class: | C07D49806 |
| Patent References Cited: | 5516926 May 1996 Kim et al. 5516927 May 1996 Kim et al. 5539110 July 1996 Kim et al. |
| Other References: | Bouzard, Chemical Abstract 110:57479 (1988). Bouzard, Tetrahedron Letters, 29(16), pp. 1931-1934 (1988). Egawa, Hiroshi, et al. (1986) "A New synthesis of 7H-Pyridol 1,2,3-de! 1,4! benzoaxazine Derivatives Including an Antibacterial Agent, Ofloxacin", Chem. Pharm. Bull 34 (10):4098-4102. |
| Primary Examiner: | Datlow, Philip I. |
| رقم الانضمام: | edspgr.05952494 |
| قاعدة البيانات: | USPTO Patent Grants |
| الوصف غير متاح. |