WO1992015574A1 - Nouvelles quinolones, leur procede de preparation et les compositions pharmaceutiques en renfermant - Google Patents
Nouvelles quinolones, leur procede de preparation et les compositions pharmaceutiques en renfermant Download PDFInfo
- Publication number
- WO1992015574A1 WO1992015574A1 PCT/FR1992/000177 FR9200177W WO9215574A1 WO 1992015574 A1 WO1992015574 A1 WO 1992015574A1 FR 9200177 W FR9200177 W FR 9200177W WO 9215574 A1 WO9215574 A1 WO 9215574A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- radical
- general formula
- acid
- formula
- mineral
- Prior art date
Links
- 0 C*C(CC(C)(*1CCCCCC1)C(C)=C1)C1C(C(*)=CC)=O Chemical compound C*C(CC(C)(*1CCCCCC1)C(C)=C1)C1C(C(*)=CC)=O 0.000 description 1
- JGCHMGURKQSAKW-QLKAYGNNSA-N C/C=C(\C(c(cc1F)c(C)cc1N1CCC(CN)CC1)=O)/C(O)=O Chemical compound C/C=C(\C(c(cc1F)c(C)cc1N1CCC(CN)CC1)=O)/C(O)=O JGCHMGURKQSAKW-QLKAYGNNSA-N 0.000 description 1
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
-
- 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
Definitions
- the subject of the present invention is new quinolones and more particularly quinolones substituted by a piperidine cycle.
- Z represents an amino radical
- RI represents a radical (lower alkyl optionally hydroxylated)
- an acyl radical derived from an organic carboxylic acid, from an alkyl carbonic acid, or from an alkylsulphonic acid, or an arylamino carbonyl radical of shape :
- Ar represents a mono or bicyclic aromatic radical optionally substituted by one, two or three substituents chosen from lower alkyl, halogens and trifluoromethyl.
- X represents oxygen or sulfur.
- R2 represents oxygen bound by a semi-polar valence and n is zero or one.
- n is zero or one.
- RI represents hydrogen or a lower alkyl radical, linear or branched, optionally substituted with a hydroxyl.
- NH AC in which Ac represents the remainder of an aliphatic, aromatic or cyclanic carboxylic acid having from I to 10 carbon atoms, the remainder of an alkylcarbonic acid or else the remainder of an alkylsulfonic acid optionally substituted by a hydroxyl or a trifluoromethyl radical.
- W is a C-H or N group
- B is hydrogen or an aromatic structure with 5 or 6 links.
- Z is hydrogen, a lower alkyl radical, a trifluoromethyl radical or a halogen, and p is 1, 2 or 3
- the compounds for which ZRI is a ureido function are those which are currently preferred.
- the compounds according to the invention can be salified by adding a mineral or organic base.
- the main salts which can be used are those of alkali metals, alkaline earth metals, ammonium, iron, aluminum, the alkylamine salts, the hydroxyalkylamine salts, the phenylalkylamine salts, the pyridylalkylamine salts, the salts of cyclanylamines, dicyclanylalkoylamine salts ...
- the sodium, lithium, ammonium, N-methylglucamine and tromethanol salts are those presently preferred.
- These compounds can also be salified with a strong mineral or organic acid when RI represents hydrogen, a lower alkyl radical or a lower (hydroxyalkyl) radical.
- the compounds according to the invention have very marked anti-bacterial properties, in particular against Gram positive bacteria.
- They can therefore be used effectively as drugs for bacterial infections of the digestive tract for the treatment of bacterial dysentria, travelers' diarrhea, or intestinal infections. They can also be used topically for the treatment of eye infections or infections of the ear canal.
- the compounds according to the invention will be used in the form of pharmaceutical compositions in which the active principle of general formula I or one of its salts, is added or mixed with an excipient or an inert non-toxic pharmaceutically acceptable vehicle.
- the most suitable pharmaceutical forms are those intended for administration by the digestive route such as oral solutions or suspensions, granules, capsules, naked or coated tablets, sugar-coated powders, flavored or not flavored powder sachets, sweetened or not, pills or cachets. Solutions, creams, ointments, salts can also be used for topical application as an external antibacterial agent.
- the average dosage depends mainly on the severity of the infection and the sensitivity of the microbial germ to the antibacterial agent.
- the unit dosage ranges from 100 to 600 mg per dose.
- the daily dosage ranges from 200 to 1200 mg divided into 2 to 4 doses.
- the invention also relates to a process for obtaining the compounds of general formula I which consists in reacting 6-fluoro T-chloro 1-ethyl 4-oxo 1,4-dihydroquinoIeine 3-carboxylic acid of formula II,
- the invention also relates to a process for converting the amino compound of formula III into urea or thiourea which consists in subjecting the compound of formula III to the action of an aryl isocyanate or isothiocyanate of formula
- the crystals formed are separated, which are drained and which are crystallized from a dimethylformamide-ethanol mixture.
- the inoculation is done by adding to each capsule 10 ⁇ l of a dilution in physiological water of an 18 H broth in brain heart broth such that each cup contains approximately 10 bacteria / ml.
- the minimum inhibitory concentration is read as the first concentration of non-culture-giving antibiotic, macroscopically visible after 18 H of incubation at 37 °.
- Example II The compound of Example II was found to be the most active. In particular with regard to Staphycococcus aureus:
- the MIC is 0.2 mcg / ml
- the CMB is 0.5 mcg / ml.
- the MIC is 8 mcg / ml
- the CMB is 8 mcg / ml
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4506544A JPH06503094A (ja) | 1991-03-01 | 1992-02-27 | 新規にキノロンと、その製造方法と、それを含む医薬組成物 |
US07/946,315 US5332749A (en) | 1991-03-01 | 1992-02-27 | Quinolones, process for their preparation and pharmaceutical compositions containing same |
FI924939A FI924939A0 (fi) | 1991-03-01 | 1992-10-30 | Nya kinoloner, foerfarande foer framstaellning daerav och farmaceutiska kompositioner innehaollande dessa |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9102585A FR2673426B1 (fr) | 1991-03-01 | 1991-03-01 | Nouvelles quinolones, leur procede de preparation et les compositions en refermant. |
FR91/02585 | 1991-03-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992015574A1 true WO1992015574A1 (fr) | 1992-09-17 |
Family
ID=9410326
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1992/000177 WO1992015574A1 (fr) | 1991-03-01 | 1992-02-27 | Nouvelles quinolones, leur procede de preparation et les compositions pharmaceutiques en renfermant |
Country Status (7)
Country | Link |
---|---|
US (1) | US5332749A (fr) |
EP (1) | EP0535184A1 (fr) |
JP (1) | JPH06503094A (fr) |
AU (1) | AU1413292A (fr) |
FI (1) | FI924939A0 (fr) |
FR (1) | FR2673426B1 (fr) |
WO (1) | WO1992015574A1 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2692577B1 (fr) * | 1992-05-26 | 1996-02-02 | Bouchara Sa | Nouvelles quinolones fluorees, leur procede de preparation et les compositions pharmaceutiques en renfermant. |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0153163A2 (fr) * | 1984-02-17 | 1985-08-28 | Warner-Lambert Company | Acides 1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoléine carboxyliques substitués en 7; acides 1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphtyridine-3-naphtyridine carboxyliques substitués en 7, leurs dérivés et procédé pour leur préparation |
EP0183129A1 (fr) * | 1984-11-13 | 1986-06-04 | Kyorin Pharmaceutical Co., Ltd. | Dérivés de l'acide quinolonecarboxylique |
EP0326916A2 (fr) * | 1988-02-05 | 1989-08-09 | Bayer Ag | Dérivés des acides quinolone- et naphthyridone-carboxyliques, procédé de leur préparation et agents antibactériens et additifs pour l'alimentation les contenant |
EP0342675A2 (fr) * | 1988-05-19 | 1989-11-23 | Chugai Seiyaku Kabushiki Kaisha | Dérivés de l'acide quinolonecarboxylique |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5630964A (en) * | 1979-08-22 | 1981-03-28 | Kyorin Pharmaceut Co Ltd | Novel substituted quinolinecarboxylic acid and its preparation |
DE3606698A1 (de) * | 1986-03-01 | 1987-09-03 | Bayer Ag | 7-(1-pyrrolidinyl)-chinoloncarbonsaeure -derivate |
JPS62215572A (ja) * | 1986-03-17 | 1987-09-22 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体 |
US4851418A (en) * | 1987-08-21 | 1989-07-25 | Warner-Lambert Company | Naphthyridine antibacterial agents containing an α-amino acid in the side chain of the 7-substituent |
-
1991
- 1991-03-01 FR FR9102585A patent/FR2673426B1/fr not_active Expired - Fee Related
-
1992
- 1992-02-27 JP JP4506544A patent/JPH06503094A/ja active Pending
- 1992-02-27 EP EP92907142A patent/EP0535184A1/fr not_active Withdrawn
- 1992-02-27 WO PCT/FR1992/000177 patent/WO1992015574A1/fr not_active Application Discontinuation
- 1992-02-27 US US07/946,315 patent/US5332749A/en not_active Expired - Fee Related
- 1992-02-27 AU AU14132/92A patent/AU1413292A/en not_active Abandoned
- 1992-10-30 FI FI924939A patent/FI924939A0/fi not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0153163A2 (fr) * | 1984-02-17 | 1985-08-28 | Warner-Lambert Company | Acides 1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoléine carboxyliques substitués en 7; acides 1-cyclopropyl-1,4-dihydro-6-fluoro-4-oxo-1,8-naphtyridine-3-naphtyridine carboxyliques substitués en 7, leurs dérivés et procédé pour leur préparation |
EP0183129A1 (fr) * | 1984-11-13 | 1986-06-04 | Kyorin Pharmaceutical Co., Ltd. | Dérivés de l'acide quinolonecarboxylique |
EP0326916A2 (fr) * | 1988-02-05 | 1989-08-09 | Bayer Ag | Dérivés des acides quinolone- et naphthyridone-carboxyliques, procédé de leur préparation et agents antibactériens et additifs pour l'alimentation les contenant |
EP0342675A2 (fr) * | 1988-05-19 | 1989-11-23 | Chugai Seiyaku Kabushiki Kaisha | Dérivés de l'acide quinolonecarboxylique |
Non-Patent Citations (1)
Title |
---|
CHEMICAL ABSTRACTS, vol. 115, 1991, Columbus, Ohio, US; abstract no. 49434B, H. NAGANO ET AL.: '1-cyclopropyl-6,8-difluoro-7 (1-piperidinyl)-1,4-dihydro-4-oxoquinoline-3-car boxylic acid derivatives as bactericides' page 821 ; * |
Also Published As
Publication number | Publication date |
---|---|
JPH06503094A (ja) | 1994-04-07 |
FR2673426B1 (fr) | 1993-07-16 |
FI924939A (fi) | 1992-10-30 |
FI924939A0 (fi) | 1992-10-30 |
FR2673426A1 (fr) | 1992-09-04 |
US5332749A (en) | 1994-07-26 |
AU1413292A (en) | 1992-10-06 |
EP0535184A1 (fr) | 1993-04-07 |
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