GB2245562A - Process for the preparation of quinoline carboxylic acid derivatives - Google Patents

Process for the preparation of quinoline carboxylic acid derivatives

Info

Publication number
GB2245562A
GB2245562A GB9018360A GB9018360A GB2245562A GB 2245562 A GB2245562 A GB 2245562A GB 9018360 A GB9018360 A GB 9018360A GB 9018360 A GB9018360 A GB 9018360A GB 2245562 A GB2245562 A GB 2245562A
Authority
GB
United Kingdom
Prior art keywords
general formula
salt
compound
compounds
preparation
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
GB9018360A
Other versions
GB2245562B (en
GB9018360D0 (en
Inventor
Istvan Hermecz
Geza Kereszturi
Lelle Vasvari
Agnes Horvath
Maria Balogh
Judit Sipos
Aniko Pajor
Peter Ritli
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.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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 Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Publication of GB9018360D0 publication Critical patent/GB9018360D0/en
Publication of GB2245562A publication Critical patent/GB2245562A/en
Application granted granted Critical
Publication of GB2245562B publication Critical patent/GB2245562B/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/022—Boron compounds without C-boron linkages

Abstract

The invention relates to a new process for the preparation of compounds of general formula (I) (wherein R<1> and R<3> stand for hydrogen or C1-4 alkyl, R<2> stands for C1-4 alkyl, R<4>, R<5> and R<6> stand for hydrogen or halogen) and pharmaceutically acceptable salts thereof, which comprises reacting a compound of general formula (II) (wherein R stands for halogen or an aliphatic acyloxy group containing 2 to 6 carbon atoms or an aromatic acyloxy group containing 7 to 11 carbon atoms, and R<4>, R<5>, R<6> have the meanings defined above) with a piperazine derivative of general formula (III) (wherein R<1>, R<2> and R<3> have the meanings defined above) or a salt thereof and subjecting the compound of general formula (IV) thus obtained (wherein R, R<1>, R<2> and R<3> are as stated above) to hydrolysis after or without isolation and if desired converting the compound of general formula (I) thus obtained into a salt thereof or setting free the same from its salt. The compounds of general formula (I) are known antibacterial agents. The advantage of the process of the present invention is that it makes the desired compounds of general formula (I) available in a simple manner, with high yields and in a short reaction time.
GB9018360A 1988-12-22 1989-12-15 Process for the preparation of quinoline carboxylic acid derivatives Expired - Lifetime GB2245562B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU886560A HU203746B (en) 1988-12-22 1988-12-22 Process for producing quinoline-carboxylic acid derivatives
PCT/HU1989/000063 WO1990006922A1 (en) 1988-12-22 1989-12-15 Process for the preparation of quinoline carboxylic acid derivatives

Publications (3)

Publication Number Publication Date
GB9018360D0 GB9018360D0 (en) 1990-10-24
GB2245562A true GB2245562A (en) 1992-01-08
GB2245562B GB2245562B (en) 1992-12-23

Family

ID=10971814

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9018360A Expired - Lifetime GB2245562B (en) 1988-12-22 1989-12-15 Process for the preparation of quinoline carboxylic acid derivatives

Country Status (11)

Country Link
JP (1) JP2825641B2 (en)
KR (1) KR0146335B1 (en)
CN (1) CN1031190C (en)
AT (1) AT397385B (en)
AU (1) AU622256B2 (en)
FR (1) FR2640974B1 (en)
GB (1) GB2245562B (en)
HU (1) HU203746B (en)
IL (1) IL92821A0 (en)
WO (1) WO1990006922A1 (en)
YU (1) YU47215B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2077490B1 (en) * 1992-11-18 1996-10-16 Marga Investigacion TRIMETILSILILIC ESTERS AND SOLVATES OF CHELATES OF QUINOLIN-3-CARBOXYL ACIDS. PREPARATION AND APPLICATION TO THE QUINOLON PROCESS.
NZ260530A (en) * 1994-05-16 1997-06-24 Nigel Paul Maynard Organoborate complexes of divalent metal; use as timber treament agents
ES2092963B1 (en) * 1995-04-12 1997-12-16 Sint Quimica Sa PROCEDURE FOR THE PREPARATION OF ACID 1-CICLOPROPIL-6-FLUORO-1, 4-DIHIDRO-7- (1S, 4S) -5-METHYL-2,5-DIAZABICICLO (2.2.1) HEPT-2-IL) -4 -OXO-3-QUINOLINCARBOXILICO AND ITS SALTS.

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4550167A (en) * 1983-05-23 1985-10-29 Ethyl Corporation Preparation of 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinoline carboxylic acid
JPS6165882A (en) * 1984-09-06 1986-04-04 Hokuriku Seiyaku Co Ltd 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-piperazinyquinoline-3-carboxylic ester derivative and its preparation
JPS6185381A (en) * 1984-10-04 1986-04-30 Hokuriku Seiyaku Co Ltd Preparation of 1-ethyl-6, 8-difluoro-1, 4-dihydro-4-oxo-7-piperazinylquinoline-3-carboxylic acid derivative
WO1987003586A1 (en) * 1985-12-09 1987-06-18 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. Process for the preparation of 1-methylamino-quinoline-carboxylic acid derivatives
JPS6419069A (en) * 1987-07-14 1989-01-23 Dainippon Pharmaceutical Co Production of polyhalogenoquinoline derivative

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59122470A (en) * 1982-12-27 1984-07-14 Dai Ichi Seiyaku Co Ltd Preparation of quinoline-3-carboxylic acid derivative
JPS6078986A (en) * 1983-10-07 1985-05-04 Dai Ichi Seiyaku Co Ltd Preparation of oxazine derivative
CA1306750C (en) * 1985-12-09 1992-08-25 Istvan Hermecz Process for the preparation of quinoline carboxylic acide
US4738800A (en) * 1986-03-26 1988-04-19 Ciba-Geigy Corporation Process for the preparation of 1,4-diamino-2,3-dicyanoanthraquinones
HU198709B (en) * 1987-04-08 1989-11-28 Chinoin Gyogyszer Es Vegyeszet Process for producing quinoline-carboxylic acid derivatives

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4550167A (en) * 1983-05-23 1985-10-29 Ethyl Corporation Preparation of 1-alkyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinoline carboxylic acid
JPS6165882A (en) * 1984-09-06 1986-04-04 Hokuriku Seiyaku Co Ltd 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-piperazinyquinoline-3-carboxylic ester derivative and its preparation
JPS6185381A (en) * 1984-10-04 1986-04-30 Hokuriku Seiyaku Co Ltd Preparation of 1-ethyl-6, 8-difluoro-1, 4-dihydro-4-oxo-7-piperazinylquinoline-3-carboxylic acid derivative
WO1987003586A1 (en) * 1985-12-09 1987-06-18 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. Process for the preparation of 1-methylamino-quinoline-carboxylic acid derivatives
JPS6419069A (en) * 1987-07-14 1989-01-23 Dainippon Pharmaceutical Co Production of polyhalogenoquinoline derivative

Also Published As

Publication number Publication date
FR2640974B1 (en) 1994-02-18
YU243789A (en) 1991-02-28
ATA902489A (en) 1993-08-15
KR910700245A (en) 1991-03-14
GB2245562B (en) 1992-12-23
KR0146335B1 (en) 1998-08-17
HU203746B (en) 1991-09-30
JP2825641B2 (en) 1998-11-18
CN1043712A (en) 1990-07-11
AU4748090A (en) 1990-07-10
AU622256B2 (en) 1992-04-02
AT397385B (en) 1994-03-25
CN1031190C (en) 1996-03-06
YU47215B (en) 1995-01-31
WO1990006922A1 (en) 1990-06-28
IL92821A0 (en) 1990-09-17
HUT52086A (en) 1990-06-28
GB9018360D0 (en) 1990-10-24
FR2640974A1 (en) 1990-06-29
JPH03502803A (en) 1991-06-27

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Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19991215