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 derivatives

Info

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
Application number
ES09201983A
Other languages
Spanish (es)
Other versions
ES2055656B1 (en
Inventor
Gonzalvez Juan Carlo Carretero
Sanchez Mercedes Vicioso
Ruano Jose Luis Garcia
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Deretil SA
Original Assignee
Derivados del Etilo SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Derivados del Etilo SA filed Critical Derivados del Etilo SA
Priority to ES9201983A priority Critical patent/ES2055656B1/en
Priority to ES9302080A priority patent/ES2069500B1/en
Priority to US08/244,455 priority patent/US5521310A/en
Priority to EP93921930A priority patent/EP0619311A1/en
Priority to AU51118/93A priority patent/AU674542B2/en
Priority to PCT/ES1993/000080 priority patent/WO1994007873A1/en
Priority to JP6508738A priority patent/JPH07501835A/en
Priority to KR1019940701925A priority patent/KR0131914B1/en
Priority to CA002125287A priority patent/CA2125287A1/en
Publication of ES2055656A1 publication Critical patent/ES2055656A1/en
Application granted granted Critical
Publication of ES2055656B1 publication Critical patent/ES2055656B1/en
Priority to AU65878/96A priority patent/AU686955B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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.
ES9201983A 1992-10-07 1992-10-07 PROCEDURE FOR OBTAINING USEFUL BENZOXAZINES FOR SYNTHESIS OF OFLOXACIN, LEVOFLOXACIN AND DERIVATIVES. Expired - Lifetime ES2055656B1 (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (7)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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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