ES2077497B1 - NEW PROCEDURE FOR OBTAINING THE ACID 9-FLUORO-2,3-DIHIDRO-3-METHYL-10- (N-METHYLPIPERAZINYL -7-OXO-7H-PIRIDO (1,2,3-DE) -1,4-BERNZOXACIN- 6-CARBOXYLLIC. - Google Patents

NEW PROCEDURE FOR OBTAINING THE ACID 9-FLUORO-2,3-DIHIDRO-3-METHYL-10- (N-METHYLPIPERAZINYL -7-OXO-7H-PIRIDO (1,2,3-DE) -1,4-BERNZOXACIN- 6-CARBOXYLLIC.

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Publication number
ES2077497B1
ES2077497B1 ES9301274A ES9301274A ES2077497B1 ES 2077497 B1 ES2077497 B1 ES 2077497B1 ES 9301274 A ES9301274 A ES 9301274A ES 9301274 A ES9301274 A ES 9301274A ES 2077497 B1 ES2077497 B1 ES 2077497B1
Authority
ES
Spain
Prior art keywords
acid
methyl
pirido
dihidro
methylpiperazinyl
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 - Fee Related
Application number
ES9301274A
Other languages
Spanish (es)
Other versions
ES2077497A1 (en
Inventor
Gomez Julio Alvarez-Builla
Garcia Carolina Burgos
Arinero Jose Calatatyud
Navio Jose Luis Garcia
Jimenez Antonio Montoro
Robisco Jose Luis Novella
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.)
BYK LEO LABORATORIO FARMACEUTICO, S.L.
Original Assignee
ELMUQUIMICA FARM SL
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 ELMUQUIMICA FARM SL filed Critical ELMUQUIMICA FARM SL
Priority to ES9301274A priority Critical patent/ES2077497B1/en
Publication of ES2077497A1 publication Critical patent/ES2077497A1/en
Application granted granted Critical
Publication of ES2077497B1 publication Critical patent/ES2077497B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

NUEVO PROCEDIMIENTO DE OBTENCION DEL ACIDO 9-FLUORO-2,3-DIHIDRO-3-METIL-10-(N-METILPIPERAZINIL)-7-OXO7H-PIRIDO[1,2,3-DE]-1,4-BENZOXACIN-6-CARBOXILICO (OFLOXACINO), VERIFICADO EN LOS SIGUIENTES PASOS: PASO 1: REACCION DE 2,3-DIFLUORO-6-NITROFENOL CON CLOROACETONA. PASO 2: PROTECCION DE LA CETONA OBTENIDO POR FORMACION DE UN ACETAL CON ETILENGLICOL. PASO 3: REDUCCION DEL GRUPO NITRO CON ACIDO FORMICO A AMINO E HIDROLISIS DEL ACETAL, CON FORMACION DE UNA IMINA CICLICA. PASO 4: REDUCCION DE DICHA IMINA CON TRIBENZOILOXI-BOROHIDRURO SODICO, PARA PRODUCIR 7,8-DIFLUORO-3,4-DIHIDRO-3-METIL-2H-BENZO[1,4]OXAZINA. PASO 5: LA AMINA OBTENIDA SE HACE REACCIONAR CON ACIDO FORMICO PARA OBTENER LA FORMAMIDA CORRESPONDIENTE. PASO 6: EL PRODUCTO OBTENIDO ANTERIORMENTE SE HACE REACCIONAR CON OXICLORURO DE FOSFORO Y CLORURO DE ETOXIMALONILO PRODUCIENDO, AL BASIFICAR LA MEZCLA, EL ACIDO 4-OXO-3-QUINOLIN-6-CARBOXILICO CORRESPONDIENTE. PASO 7: EL ACIDO OBTENIDO SE HACE REACCIONAR CON 1-METILPIPERAZINA PARA OBTENEREL ACIDO 9-FLUORO-2,3-DIHIDRO-3-METIL-10-(N-METILPIPERAZINIL)-7-OXO-7H-PIRIDO[1,2,3-DE]-1,4-BENZOXACIN-6-CARBOXILICO (OFLOXACINO) OBJETO DE ESTA INVENCION. APLICACIONES: ESTE COMPUESTO TIENE SU APLICACION DENTRO DEL CAMPO DE LA QUIMICA TERAPEUTICA COMO AGENTE ANTIBACTERIANO.NEW PROCEDURE FOR OBTAINING THE ACID 9-FLUORO-2,3-DIHIDRO-3-METHYL-10- (N-METHYLPIPERAZINYL) -7-OXO7H-PIRIDO [1,2,3-DE] -1,4-BENZOXACIN-6 -CARBOXYLIC (OFLOXACINO), VERIFIED IN THE FOLLOWING STEPS: STEP 1: REACTION OF 2,3-DIFLUORO-6-NITROPHENOL WITH CHLOROACETONE. STEP 2: PROTECTION OF THE KETONE OBTAINED BY FORMATION OF AN ACETAL WITH ETHYLENE GLYCOL. STEP 3: REDUCTION OF THE NITRO GROUP WITH FORMIC ACID TO AMINO AND HYDROLYSIS OF ACETAL, WITH FORMATION OF A CYCLICAL IMINE. STEP 4: REDUCTION OF SUCH IMINA WITH SODIUM TRIBENZOILOXI-BOROHIDRIDE, TO PRODUCE 7,8-DIFLUORO-3,4-DIHIDRO-3-METHYL-2H-BENZO [1,4] OXAZINE. STEP 5: THE AMINE OBTAINED IS REACTIONED WITH FORMIC ACID TO OBTAIN THE CORRESPONDING FORMAMIDE. STEP 6: THE PRODUCT OBTAINED ABOVE IS REACTED WITH PHOSPHOR OXYCHLORIDE AND ETHOXIMALONYL CHLORIDE PRODUCING, BY BASIFICATION OF THE MIXTURE, THE CORRESPONDING 4-OXO-3-QUINOLIN-6-CARBOXYLIC ACID. STEP 7: THE ACID OBTAINED IS REACTED WITH 1-METHYLPIPERAZINE TO OBTAIN THE ACID 9-FLUORO-2,3-DIHYDRO-3-METHYL-10- (N-METHYLPIPERAZINYL) -7-OXO-7H-PIRIDO [1,2, 3-DE] -1,4-BENZOXACIN-6-CARBOXILICO (OFLOXACINO) OBJECT OF THIS INVENTION. APPLICATIONS: THIS COMPOUND HAS ITS APPLICATION WITHIN THE FIELD OF THERAPEUTIC CHEMISTRY AS AN ANTIBACTERIAL AGENT.

ES9301274A 1993-06-10 1993-06-10 NEW PROCEDURE FOR OBTAINING THE ACID 9-FLUORO-2,3-DIHIDRO-3-METHYL-10- (N-METHYLPIPERAZINYL -7-OXO-7H-PIRIDO (1,2,3-DE) -1,4-BERNZOXACIN- 6-CARBOXYLLIC. Expired - Fee Related ES2077497B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ES9301274A ES2077497B1 (en) 1993-06-10 1993-06-10 NEW PROCEDURE FOR OBTAINING THE ACID 9-FLUORO-2,3-DIHIDRO-3-METHYL-10- (N-METHYLPIPERAZINYL -7-OXO-7H-PIRIDO (1,2,3-DE) -1,4-BERNZOXACIN- 6-CARBOXYLLIC.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES9301274A ES2077497B1 (en) 1993-06-10 1993-06-10 NEW PROCEDURE FOR OBTAINING THE ACID 9-FLUORO-2,3-DIHIDRO-3-METHYL-10- (N-METHYLPIPERAZINYL -7-OXO-7H-PIRIDO (1,2,3-DE) -1,4-BERNZOXACIN- 6-CARBOXYLLIC.

Publications (2)

Publication Number Publication Date
ES2077497A1 ES2077497A1 (en) 1995-11-16
ES2077497B1 true ES2077497B1 (en) 1996-10-16

Family

ID=8282127

Family Applications (1)

Application Number Title Priority Date Filing Date
ES9301274A Expired - Fee Related ES2077497B1 (en) 1993-06-10 1993-06-10 NEW PROCEDURE FOR OBTAINING THE ACID 9-FLUORO-2,3-DIHIDRO-3-METHYL-10- (N-METHYLPIPERAZINYL -7-OXO-7H-PIRIDO (1,2,3-DE) -1,4-BERNZOXACIN- 6-CARBOXYLLIC.

Country Status (1)

Country Link
ES (1) ES2077497B1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100204507A1 (en) * 2007-08-31 2010-08-12 Roeder Jens Acyloxy compounds of elements of the boron group

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4826985A (en) * 1986-04-25 1989-05-02 Abbott Laboratories Intermediates for preparation of racemate and optically active ofloxacin and related derivatives
ATE110061T1 (en) * 1986-12-25 1994-09-15 Daiichi Seiyaku Co OPTICALLY ACTIVE 2,3-DIHYDROBENZOXAZINE DERIVATIVES AND PROCESS FOR THEIR PREPARATION.
NO172846C (en) * 1987-12-25 1993-09-15 Daiichi Seiyaku Co PROCEDURE FOR PREPARING 7,8-DIHALOGEN-3-METHYL-2,3-DIHYDRO-2M-BENZOCSAZINE DERIVATIVES AND PROPOXYBENZEN DERIVATIVES FOR EXERCISING THE PROCEDURE.

Also Published As

Publication number Publication date
ES2077497A1 (en) 1995-11-16

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