ES2055656A1 - Procedure for obtaining benzoxazines useful for the synthesis of ofloxacin, levofloxacin and derivatives - Google Patents
Procedure for obtaining benzoxazines useful for the synthesis of ofloxacin, levofloxacin and derivativesInfo
- Publication number
- ES2055656A1 ES2055656A1 ES09201983A ES9201983A ES2055656A1 ES 2055656 A1 ES2055656 A1 ES 2055656A1 ES 09201983 A ES09201983 A ES 09201983A ES 9201983 A ES9201983 A ES 9201983A ES 2055656 A1 ES2055656 A1 ES 2055656A1
- Authority
- ES
- Spain
- Prior art keywords
- levofloxacin
- synthesis
- ofloxacin
- derivatives
- procedure
- 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
Abstract
Procedure for obtaining benzoxazines useful for the synthesis of ofloxacin, levofloxacin and derivatives. Procedure for obtaining benzoxazines useful for the synthesis of Ofloxacin, Levofloxacin and derivatives. The benzoxazines (I), where Xb is a halogen and R1 is H, alkyl or alkylene of up to 6 C atoms or aryl, can be obtained by cyclization of a compound of formula (II) by reaction with triphenylphosphine and ethyl azodicarboxylate. The compounds of formula (II) can be obtained by reaction of a compound (III) with a suitable epoxide. The enantiomerically desired intermediate can be obtained by use of the appropriate chiral epoxide, and consequently the desired final product can be obtained selectively with the appropriate enantiomeric form without the need to perform any resolution step. The compounds (I) are valuable intermediates and keys for the synthesis of the antimicrobials Oflaxacin and Levofloxacin.
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9201983A ES2055656B1 (en) | 1992-10-07 | 1992-10-07 | PROCEDURE FOR OBTAINING USEFUL BENZOXAZINES FOR SYNTHESIS OF OFLOXACIN, LEVOFLOXACIN AND DERIVATIVES. |
ES9302080A ES2069500B1 (en) | 1992-10-07 | 1993-10-04 | IMPROVEMENTS INTRODUCED IN THE PURPOSE OF THE SPANISH PATENT N 9201983 FOR "PROCEDURE TO OBTAIN USEFUL BENZOXAZINES FOR THE SYNTHESIS OF OFLEXACINE, LEVOFLOXACIN AND DERIVATIVES. |
EP93921930A EP0619311A1 (en) | 1992-10-07 | 1993-10-06 | Process for obtaining benzoxazines useful for the synthesis of ofloxacin, levofloxacin and derivatives thereof |
AU51118/93A AU674542B2 (en) | 1992-10-07 | 1993-10-06 | Process for obtaining benzoxazines useful for the synthesis of ofloxacin, levofloxacin and derivatives thereof |
PCT/ES1993/000080 WO1994007873A1 (en) | 1992-10-07 | 1993-10-06 | Process for obtaining benzoxazines useful for the synthesis of ofloxacin, levofloxacin and derivatives thereof |
JP6508738A JPH07501835A (en) | 1992-10-07 | 1993-10-06 | Process for producing benzoxazine used in the synthesis of ofloxazine, levofloxazine and derivatives |
US08/244,455 US5521310A (en) | 1992-10-07 | 1993-10-06 | Process to obtain benzoxazines to be used for the synthesis of ofloxazine, levofloxazine and derivatives |
KR1019940701925A KR0131914B1 (en) | 1992-10-07 | 1993-10-06 | Process for obtaining benzoxanines useful for the synthesis of ofloxacin, levofloxacin and derivatives and derivatives thereof |
CA002125287A CA2125287A1 (en) | 1992-10-07 | 1993-10-06 | Process to obtain benzoxazines to be used for the synthesis of ofloxazine, levofloxazine and derivatives |
AU65878/96A AU686955B2 (en) | 1992-10-07 | 1996-09-27 | Process to obtain benzoxazines to be used for the synthesis of ofloxazine, levofloxazine and derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9201983A ES2055656B1 (en) | 1992-10-07 | 1992-10-07 | PROCEDURE FOR OBTAINING USEFUL BENZOXAZINES FOR SYNTHESIS OF OFLOXACIN, LEVOFLOXACIN AND DERIVATIVES. |
Publications (2)
Publication Number | Publication Date |
---|---|
ES2055656A1 true ES2055656A1 (en) | 1994-08-16 |
ES2055656B1 ES2055656B1 (en) | 1995-11-16 |
Family
ID=8278329
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES9201983A Expired - Lifetime ES2055656B1 (en) | 1992-10-07 | 1992-10-07 | PROCEDURE FOR OBTAINING USEFUL BENZOXAZINES FOR SYNTHESIS OF OFLOXACIN, LEVOFLOXACIN AND DERIVATIVES. |
ES9302080A Expired - Lifetime ES2069500B1 (en) | 1992-10-07 | 1993-10-04 | IMPROVEMENTS INTRODUCED IN THE PURPOSE OF THE SPANISH PATENT N 9201983 FOR "PROCEDURE TO OBTAIN USEFUL BENZOXAZINES FOR THE SYNTHESIS OF OFLEXACINE, LEVOFLOXACIN AND DERIVATIVES. |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES9302080A Expired - Lifetime ES2069500B1 (en) | 1992-10-07 | 1993-10-04 | IMPROVEMENTS INTRODUCED IN THE PURPOSE OF THE SPANISH PATENT N 9201983 FOR "PROCEDURE TO OBTAIN USEFUL BENZOXAZINES FOR THE SYNTHESIS OF OFLEXACINE, LEVOFLOXACIN AND DERIVATIVES. |
Country Status (1)
Country | Link |
---|---|
ES (2) | ES2055656B1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7629458B2 (en) | 2001-10-03 | 2009-12-08 | Teva Pharmaceutical Industries Ltd. | Preparation of levofloxacin and hemihydrate thereof |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES8801210A1 (en) * | 1985-06-22 | 1987-12-16 | Bayer Ag | Process for the preparation of 1,8-bridged 4-quinolone-3-carboxylic acids. |
ES8801251A1 (en) * | 1985-06-20 | 1988-01-01 | Daiichi Seiyaku Co | Optically active pyridobenzoxazine derivatives. |
EP0268223A2 (en) * | 1986-11-18 | 1988-05-25 | Hoechst Aktiengesellschaft | Optically active gyrase inhibitors, their preparation and use as antibiotics |
EP0273399A1 (en) * | 1986-12-25 | 1988-07-06 | Daiichi Pharmaceutical Co., Ltd. | Optically active 2,3-dihydrobenzoaxine derivatives and process for preparing the same |
US4826985A (en) * | 1986-04-25 | 1989-05-02 | Abbott Laboratories | Intermediates for preparation of racemate and optically active ofloxacin and related derivatives |
EP0322815A2 (en) * | 1987-12-25 | 1989-07-05 | Daiichi Pharmaceutical Co., Ltd. | Propoxybenzene derivatives and process for preparing the same |
-
1992
- 1992-10-07 ES ES9201983A patent/ES2055656B1/en not_active Expired - Lifetime
-
1993
- 1993-10-04 ES ES9302080A patent/ES2069500B1/en not_active Expired - Lifetime
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES8801251A1 (en) * | 1985-06-20 | 1988-01-01 | Daiichi Seiyaku Co | Optically active pyridobenzoxazine derivatives. |
ES8801210A1 (en) * | 1985-06-22 | 1987-12-16 | Bayer Ag | Process for the preparation of 1,8-bridged 4-quinolone-3-carboxylic acids. |
ES8801920A1 (en) * | 1985-06-22 | 1988-03-01 | Bayer Ag | Process for the preparation of 1,8-bridged 4-quinolone-3-carboxylic acids. |
US4826985A (en) * | 1986-04-25 | 1989-05-02 | Abbott Laboratories | Intermediates for preparation of racemate and optically active ofloxacin and related derivatives |
EP0268223A2 (en) * | 1986-11-18 | 1988-05-25 | Hoechst Aktiengesellschaft | Optically active gyrase inhibitors, their preparation and use as antibiotics |
EP0273399A1 (en) * | 1986-12-25 | 1988-07-06 | Daiichi Pharmaceutical Co., Ltd. | Optically active 2,3-dihydrobenzoaxine derivatives and process for preparing the same |
EP0322815A2 (en) * | 1987-12-25 | 1989-07-05 | Daiichi Pharmaceutical Co., Ltd. | Propoxybenzene derivatives and process for preparing the same |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7629458B2 (en) | 2001-10-03 | 2009-12-08 | Teva Pharmaceutical Industries Ltd. | Preparation of levofloxacin and hemihydrate thereof |
Also Published As
Publication number | Publication date |
---|---|
ES2055656B1 (en) | 1995-11-16 |
ES2069500A1 (en) | 1995-05-01 |
ES2069500B1 (en) | 1996-03-01 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PC2A | Transfer of patent |