ES2092963B1 - Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1, 4-dihidro-7-(1s,4s)-5-metil-2,5-diazabiciclo(2.2.1) hept-2-il)-4-oxo-3-quinolincarboxilico y sus sales. - Google Patents

Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1, 4-dihidro-7-(1s,4s)-5-metil-2,5-diazabiciclo(2.2.1) hept-2-il)-4-oxo-3-quinolincarboxilico y sus sales.

Info

Publication number
ES2092963B1
ES2092963B1 ES09500782A ES9500782A ES2092963B1 ES 2092963 B1 ES2092963 B1 ES 2092963B1 ES 09500782 A ES09500782 A ES 09500782A ES 9500782 A ES9500782 A ES 9500782A ES 2092963 B1 ES2092963 B1 ES 2092963B1
Authority
ES
Spain
Prior art keywords
ciclopropil
diazabiciclo
methyl
acid
hept
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
ES09500782A
Other languages
English (en)
Other versions
ES2092963A1 (es
Inventor
Darder Carlos Picornell
Harnandez Pedro Gonzalez
Gonzalez M Luisa Salas
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.)
Quimica Sintetica SA
Original Assignee
Quimica Sintetica 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 Quimica Sintetica SA filed Critical Quimica Sintetica SA
Priority to ES09500782A priority Critical patent/ES2092963B1/es
Priority to CZ96974A priority patent/CZ97496A3/cs
Priority to GR960100116A priority patent/GR960100116A/el
Priority to AR33607596A priority patent/AR001560A1/es
Priority to KR1019960010690A priority patent/KR960037676A/ko
Priority to PT101864A priority patent/PT101864B/pt
Priority to FI961583A priority patent/FI961583L/fi
Priority to MX9601351A priority patent/MX9601351A/es
Priority to HU9600941A priority patent/HUP9600941A3/hu
Priority to NO961442A priority patent/NO961442L/no
Priority to AT0065396A priority patent/ATA65396A/de
Priority to PL96313697A priority patent/PL313697A1/xx
Priority to SK468-96A priority patent/SK46896A3/sk
Publication of ES2092963A1 publication Critical patent/ES2092963A1/es
Application granted granted Critical
Publication of ES2092963B1 publication Critical patent/ES2092963B1/es
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

PROCEDIMIENTO PARA LA PREPARACION DEL ACIDO 1- CICLOPROPIL - 6 - FLUORO - 1,4- DIHIDRO - 7 - [(1S,4S)] -5 - METIL - 2,5 - DIAZABICICLO [2.2.1]HEPT-2-IL] - 4-OXO -3 - QUINOLINCARBOXILICO Y SUS SALES. SE CARACTERIZA POR EL TRATAMIENTO DE UN 1 - CICLOPROPIL - 6 - FLUORO - 7 - CLORO - 1,4 - DIHIDRO - 4 - OXOQUINOLIN - 3 - CARBOXILATO DE C1 - C4 - ALQUILO CON ACIDO BORICO EN PRESENCIA DE ANHIDRIDO ACETICO Y CANTIDADES CATALITICAS DE ZINC PARA PROPORCIONAR (1 - CICLOPROPIL - 6 - FLUORO - 7 - CLORO - 1,4 - DIHIDRO - 4 - OXOQUINOLIN - 3 - CARBOXILATO-Q3,-Q4) BIS (ACETATO-O) BORO, POSTERIOR TRATAMIENTO DEL PRODUCTO CON (1S,4S) - 5 - METIL - 2,5 - DIAZABICICLO [2.2.1] HEPTANO O UNA SAL DE ADICION DE ACIDO DEL MISMO, EVENTUALMENTE EN PRESENCIA DE UNA BASE, PARA DAR LUGAR AL INTERMEDIO (1 - CICLOPROPIL - 6 - FLUORURO - 1,4 - DIHIDRO - 7 - [1S,4S) - 5 - METIL - 2,5 - DIAZABICICLO [2.2.1] HEPT - 2- IL] - 4 -OXO - 3- QUINOLINCARBOXILATO - O3, - O4) BIS (ACETATO-O) - BORO, E HIDROLISIS FINAL PARA OBTENER EL PRODUCTO DESEADO, CON ELEVADO RENDIMIENTO Y PUREZA, QUE SE AISLA DEL MEDIO DE REACCION POR LOS PROCEDIMIENTOS CONVENCIONALES.
ES09500782A 1995-04-12 1995-04-12 Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1, 4-dihidro-7-(1s,4s)-5-metil-2,5-diazabiciclo(2.2.1) hept-2-il)-4-oxo-3-quinolincarboxilico y sus sales. Expired - Fee Related ES2092963B1 (es)

Priority Applications (13)

Application Number Priority Date Filing Date Title
ES09500782A ES2092963B1 (es) 1995-04-12 1995-04-12 Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1, 4-dihidro-7-(1s,4s)-5-metil-2,5-diazabiciclo(2.2.1) hept-2-il)-4-oxo-3-quinolincarboxilico y sus sales.
CZ96974A CZ97496A3 (en) 1995-04-12 1996-04-03 Process for preparing 1-cyclopropyl-6-fluoro-1, 4-dihydro-7-£(1s, 4s)|-5-methyl-2,5-diazabicyclo £2.2.1|hept-2-yl|-4-oxo-3-quinolinecarboxylic acid and salts thereof
GR960100116A GR960100116A (el) 1995-04-12 1996-04-03 Μεθοδος παρασκευης 1-κυκλοπροπυλο-6-φλουορο-1,4-διυδρο-7-[(1s,4s)-5-μεθυλο-2,5-διαζαβικυκλο[2.2.1]-επτ-2-υλο] -4-οξο-3-κουινολινοκαρβοξυλικο οξυ και αλατα αυτων.
AR33607596A AR001560A1 (es) 1995-04-12 1996-04-08 Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1,4-dihidro-7-7Ä(1S,4S)-5-metil-2,5-diazabiciclo)-Ä2.2.1Ühept-2-ilÜ-4-oxo-3-quinolincarboxilico y sus sales
PT101864A PT101864B (pt) 1995-04-12 1996-04-10 Processo para a preparacao de acido 1-ciclopropil-6-fluoro-1,4-dihidro-7-({1s,4s}-5-metil-2,5-diazabiciclo{2,2,1}-hept-2-il}-4-oxo-3-quinolinocarboxilico e os seus sais
KR1019960010690A KR960037676A (ko) 1995-04-12 1996-04-10 1-사이클로프로필-6-플루오로-1,4-디하이드로-7-[(1s,4s)-5-메틸-2,5-디아자비사이클로[2.2.1]-헵트-2-일]-4-옥소-3-퀴놀린카복실산 및 이의 염의 제조방법
FI961583A FI961583L (fi) 1995-04-12 1996-04-11 Menetelmä 1-syklopropyyli-6-fluori-1,4-dihydro-7-/(1S,4S)-5-metyyli-2,5-diatsabisyklo/2.2.1/-hept-2-yyli/-4-okso-3-kinoliinikarboksyylihapon ja sen suolan valmistamiseksi
MX9601351A MX9601351A (es) 1995-04-12 1996-04-11 Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1,4-dihidro-7-[(1s, 4s)-5-metil-2,5- diazabiciclo[2.2.1]hept-2-il]-4-oxo-3-quinolincarboxilico y sus sales.
HU9600941A HUP9600941A3 (en) 1995-04-12 1996-04-11 Process for the preparation of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-[1s,4s]-5-methyl-2,5-diazabicyclo-[2.2.1]hept-2-yl-4-oxo-3-quinolinecarboxylic acid and its salts
NO961442A NO961442L (no) 1995-04-12 1996-04-11 Fremgangsmåte til fremstilling av 1-cyklopropyl-6-fluor-1,4-dihydro-7-[(1S,4S)-5-metyl-2,5-diazabicyklo[2.2.1Å-hept-2-ylÅ-4-okso-3-kinolinkarboksylsyre og dens salter
AT0065396A ATA65396A (de) 1995-04-12 1996-04-11 Verfahren zur herstellung von 1-cyclopropyl-6-fluor-1,4-dihydro-7-((1s,4s)-5- methyl-2,5-diazabicyclo (2.2.1)hept-2-yl)-4-oxo-3-chinolincarbonsäure und ihren salzen
PL96313697A PL313697A1 (en) 1995-04-12 1996-04-11 Method of obtaining cyclopropylo-6-fluoro-1,4-dihydro-7-/ (1s,4s)-5-methylo-2,5-diazabicyclo /2.2.1)hept-2-yl/ 4-keto-3-quinolinocarboxylic acid and its salts/
SK468-96A SK46896A3 (en) 1995-04-12 1996-04-12 Preperation method of 1-cyclopropyl-6-fluor-1,4-dihydro-7- -£(1s,4s)-5-methyl-2,5-diazabicyclo-£2.2.1.|hept-2-yl|-4-oxo-3- -quinoline-carboxylic acid and its salts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES09500782A ES2092963B1 (es) 1995-04-12 1995-04-12 Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1, 4-dihidro-7-(1s,4s)-5-metil-2,5-diazabiciclo(2.2.1) hept-2-il)-4-oxo-3-quinolincarboxilico y sus sales.

Publications (2)

Publication Number Publication Date
ES2092963A1 ES2092963A1 (es) 1996-12-01
ES2092963B1 true ES2092963B1 (es) 1997-12-16

Family

ID=8290154

Family Applications (1)

Application Number Title Priority Date Filing Date
ES09500782A Expired - Fee Related ES2092963B1 (es) 1995-04-12 1995-04-12 Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1, 4-dihidro-7-(1s,4s)-5-metil-2,5-diazabiciclo(2.2.1) hept-2-il)-4-oxo-3-quinolincarboxilico y sus sales.

Country Status (13)

Country Link
KR (1) KR960037676A (es)
AR (1) AR001560A1 (es)
AT (1) ATA65396A (es)
CZ (1) CZ97496A3 (es)
ES (1) ES2092963B1 (es)
FI (1) FI961583L (es)
GR (1) GR960100116A (es)
HU (1) HUP9600941A3 (es)
MX (1) MX9601351A (es)
NO (1) NO961442L (es)
PL (1) PL313697A1 (es)
PT (1) PT101864B (es)
SK (1) SK46896A3 (es)

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN166416B (es) * 1985-09-18 1990-05-05 Pfizer
HU196218B (en) * 1985-12-09 1988-10-28 Chinoin Gyogyszer Es Vegyeszet Process for preparing quinoline carboxylic acid boric acid anhydrides
CA1306750C (en) * 1985-12-09 1992-08-25 Istvan Hermecz Process for the preparation of quinoline carboxylic acide
EP0251308B1 (de) * 1986-07-04 1990-11-22 Chemie Linz Gesellschaft m.b.H. 4-Chinolon-3-carbonsäurederivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
GR1000469B (el) * 1987-04-08 1992-07-30 Chinoin Gyogyszer Es Vegyeszet Mεθοδος παρασκευης κινολινοκαρβοξυλικων οξεων.
HU198709B (en) * 1987-04-08 1989-11-28 Chinoin Gyogyszer Es Vegyeszet Process for producing quinoline-carboxylic acid derivatives
YU46451B (sh) * 1987-04-08 1993-10-20 Chinoin Gyogyszer Es Vegyeszeti Ter Mekek Gyara Rt. Postupak za dobivanje mešovitih anhidrida hinolin-karboksilne i borne kiseline
EP0329719A1 (en) * 1987-06-24 1989-08-30 CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. Process for the preparation of quinoline carboxylic acid derivatives
HU203746B (en) * 1988-12-22 1991-09-30 Chinoin Gyogyszer Es Vegyeszet Process for producing quinoline-carboxylic acid derivatives
JPH0778065B2 (ja) * 1990-07-06 1995-08-23 杏林製薬株式会社 （６，７―置換―８―アルコキシ―１―シクロプロピル―１，４―ジヒドロ―４―オキソ―３―キノリンカルボン酸―ｏ▲上３▼，ｏ▲上４▼）ビス（アシルオキシ―ｏ）ホウ素化合物及びその塩並びにその製造方法

Also Published As

Publication number Publication date
PT101864A (pt) 1997-01-31
HUP9600941A3 (en) 1998-01-28
PT101864B (pt) 1997-12-31
NO961442L (no) 1996-10-14
FI961583A0 (fi) 1996-04-11
FI961583A7 (fi) 1996-10-13
MX9601351A (es) 1997-04-30
HU9600941D0 (en) 1996-06-28
CZ97496A3 (en) 1996-10-16
AR001560A1 (es) 1997-11-26
KR960037676A (ko) 1996-11-19
PL313697A1 (en) 1996-10-14
ATA65396A (de) 1998-09-15
HUP9600941A2 (en) 1997-06-30
FI961583L (fi) 1996-10-13
ES2092963A1 (es) 1996-12-01
NO961442D0 (no) 1996-04-11
SK46896A3 (en) 1997-07-09
GR960100116A (el) 1996-12-31

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