ES2092963A1 - 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
- ES2092963A1 ES2092963A1 ES09500782A ES9500782A ES2092963A1 ES 2092963 A1 ES2092963 A1 ES 2092963A1 ES 09500782 A ES09500782 A ES 09500782A ES 9500782 A ES9500782 A ES 9500782A ES 2092963 A1 ES2092963 A1 ES 2092963A1
- Authority
- ES
- Spain
- Prior art keywords
- cyclopropyl
- dihydro
- fluoro
- diazabicyclo
- methyl
- 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
- 238000000034 method Methods 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 title abstract 3
- QMLVECGLEOSESV-RYUDHWBXSA-N Danofloxacin Chemical compound C([C@@H]1C[C@H]2CN1C)N2C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=CC=1N2C1CC1 QMLVECGLEOSESV-RYUDHWBXSA-N 0.000 title abstract 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 2
- 229910052796 boron Inorganic materials 0.000 abstract 2
- YFDRYBUJCGOYCQ-WDSKDSINSA-N (1s,4s)-2-methyl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1N(C)[C@]2([H])CN[C@@]1([H])C2 YFDRYBUJCGOYCQ-WDSKDSINSA-N 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
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.
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. |
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. |
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 |
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 |
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 |
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 |
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 |
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. |
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/ |
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 |
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 |
FI961583A FI961583A (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 |
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 true ES2092963A1 (es) | 1996-12-01 |
ES2092963B1 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) | FI961583A (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) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2001428A6 (es) * | 1985-09-18 | 1988-05-16 | Pfizer | Un procedimiento para la preparacion de acidos diazabiciclo-alquil-puenteado-quinolon-carboxilicos sustituidos y sus derivados acidos. |
ES2006881A6 (es) * | 1987-04-08 | 1989-05-16 | Chinoin Gyogyszer Es Vegyeszet | Procedimiento de preparar nuevos derivados anhidrido de acido quinolincarboxilicoacido borico. |
ES2006882A6 (es) * | 1987-04-08 | 1989-05-16 | Chinoin Gyogyszer Es Vegyeszet | Procedimiento para la preparacion de acidos quinolincarboxilicos. |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1306750C (en) * | 1985-12-09 | 1992-08-25 | Istvan Hermecz | Process for the preparation of quinoline carboxylic acide |
HU196218B (en) * | 1985-12-09 | 1988-10-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing quinoline carboxylic acid boric acid anhydrides |
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 |
HU198709B (en) * | 1987-04-08 | 1989-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing quinoline-carboxylic acid derivatives |
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 |
-
1995
- 1995-04-12 ES ES09500782A patent/ES2092963B1/es not_active Expired - Fee Related
-
1996
- 1996-04-03 CZ CZ96974A patent/CZ97496A3/cs unknown
- 1996-04-03 GR GR960100116A patent/GR960100116A/el unknown
- 1996-04-08 AR AR33607596A patent/AR001560A1/es unknown
- 1996-04-10 PT PT101864A patent/PT101864B/pt not_active IP Right Cessation
- 1996-04-10 KR KR1019960010690A patent/KR960037676A/ko not_active Application Discontinuation
- 1996-04-11 AT AT0065396A patent/ATA65396A/de not_active Application Discontinuation
- 1996-04-11 NO NO961442A patent/NO961442L/no unknown
- 1996-04-11 HU HU9600941A patent/HUP9600941A3/hu unknown
- 1996-04-11 MX MX9601351A patent/MX9601351A/es unknown
- 1996-04-11 PL PL96313697A patent/PL313697A1/xx unknown
- 1996-04-11 FI FI961583A patent/FI961583A/fi not_active Application Discontinuation
- 1996-04-12 SK SK468-96A patent/SK46896A3/sk unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2001428A6 (es) * | 1985-09-18 | 1988-05-16 | Pfizer | Un procedimiento para la preparacion de acidos diazabiciclo-alquil-puenteado-quinolon-carboxilicos sustituidos y sus derivados acidos. |
ES2006881A6 (es) * | 1987-04-08 | 1989-05-16 | Chinoin Gyogyszer Es Vegyeszet | Procedimiento de preparar nuevos derivados anhidrido de acido quinolincarboxilicoacido borico. |
ES2006882A6 (es) * | 1987-04-08 | 1989-05-16 | Chinoin Gyogyszer Es Vegyeszet | Procedimiento para la preparacion de acidos quinolincarboxilicos. |
Non-Patent Citations (1)
Title |
---|
McGUIRK, P.R. y col. Synthesis and Structure-Activity Relationships of 7-Diazabicycloalkylquinolones, Including Danofloxacin, a New Quinolone Antibacterial Agent for Veterinary Medicine. Febrero 1992, Vol. 35, N 4, pßginas 611-620 * Esquema I * * |
Also Published As
Publication number | Publication date |
---|---|
ATA65396A (de) | 1998-09-15 |
KR960037676A (ko) | 1996-11-19 |
NO961442D0 (no) | 1996-04-11 |
PT101864A (pt) | 1997-01-31 |
PT101864B (pt) | 1997-12-31 |
PL313697A1 (en) | 1996-10-14 |
MX9601351A (es) | 1997-04-30 |
HU9600941D0 (en) | 1996-06-28 |
HUP9600941A2 (en) | 1997-06-30 |
AR001560A1 (es) | 1997-11-26 |
GR960100116A (el) | 1996-12-31 |
FI961583A0 (fi) | 1996-04-11 |
FI961583A (fi) | 1996-10-13 |
ES2092963B1 (es) | 1997-12-16 |
SK46896A3 (en) | 1997-07-09 |
NO961442L (no) | 1996-10-14 |
HUP9600941A3 (en) | 1998-01-28 |
CZ97496A3 (en) | 1996-10-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EC2A | Search report published |
Date of ref document: 19961201 Kind code of ref document: A1 Effective date: 19961201 |
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FD1A | Patent lapsed |
Effective date: 20020401 |