EP1019376A1 - Pyridon-derivate, ihre herstellung und verwendung als zwischenprodukte in der synthese - Google Patents

Pyridon-derivate, ihre herstellung und verwendung als zwischenprodukte in der synthese

Info

Publication number
EP1019376A1
EP1019376A1 EP98902060A EP98902060A EP1019376A1 EP 1019376 A1 EP1019376 A1 EP 1019376A1 EP 98902060 A EP98902060 A EP 98902060A EP 98902060 A EP98902060 A EP 98902060A EP 1019376 A1 EP1019376 A1 EP 1019376A1
Authority
EP
European Patent Office
Prior art keywords
group
compound
formula
alkyl
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.)
Ceased
Application number
EP98902060A
Other languages
English (en)
French (fr)
Inventor
Gilbert Lassalle
Patrice Bellevergue
Jean-Claude Bourbier
Daniel Galtier
Valérie Martin
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.)
Sanofi Aventis France
Original Assignee
Sanofi Synthelabo 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 Sanofi Synthelabo SA filed Critical Sanofi Synthelabo SA
Publication of EP1019376A1 publication Critical patent/EP1019376A1/de
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to pyridone derivatives, their preparation and their use as synthesis intermediates.
  • the compounds according to the invention correspond to formula (I)
  • R represents either a group -N0 2 or a group -NHR 3 , R 3 being a hydrogen atom, a group -C0R 4 (where R 4 is chosen from (C 1 -C 4 ) alkyl, aryl and aryl (C 1 -C 4 ) alkyl), a group -COOR 5 (where R 5 is chosen from the groups (C 1 -C 4 ) alkyl and aryl (C;] _- C 4 ) alkyl), a group - CONHR 6 a group -S0 2 R 6 (where R 6 is chosen from (C 1 -C 5 ) alkyl, aryl and aryl (C 1 -C 4 ) alkyl groups), a group -S0 2 NR 7 R 8 ( where R 7 and R 8 are each independently of one another a hydrogen atom or a (C 1 -C 4 ) alkyl group or form with the nitrogen atom which carries them a morpholine group),
  • R 2 represents either a hydrogen atom, or a (C 1 -C) alkyl group, or an arylmethyl group
  • X represents either an oxygen or sulfur atom, or a group -CH 2 -, -S0 2 _ or -NR X - where R is as defined above and
  • Y represents either a hydrogen atom or a (C 1 -C 6 ) straight or branched alkyl group.
  • the aryl groups are aromatic carbon rings, for example phenyl, naphthyl or anthracenyl, and the heteroaryl groups are aromatic heterocycles, for example pyridine or thiophene.
  • the compounds can exist in the form of pure racemates or enantiomers or as a mixture of enantiomers which also form part of the invention.
  • R x represents either a (C] _- C 4 ) straight or branched alkyl group, or a cyclo (C 3 -C 8 ) alkyl group
  • X an atom of oxygen
  • R 2 a hydrogen atom or a (C 1 -C 4 ) alkyl group
  • R 3 and Y are as defined above
  • compound of formula (Ib) corresponding either with a compound R 3 -Hal where Hal represents a halogen atom, or with a compound of formula R 6 NCO, or it is subjected to a reductive amination when R 3 represents an aryl group ( C 1 -C 4 ) alkyl.
  • R 3 represents an aryl group ( C 1 -C 4 ) alkyl.
  • R x represents either an aryl group optionally substituted by a halogen atom, a (C 1 -C 5 ) straight or branched alkyl group, a trifluoromethyl group, a cyano group or a (C 1 -C 4 ) acylamino group, either an aryl (C 1 -C 4 ) alkyl group optionally substituted as above, or a heteroaryl group
  • X represents either a sulfur atom or a group - CH 2 -, -S0 2 - or -NR ⁇
  • R 2 represents a hydrogen atom or a (C 3 _-C 4 ) alkyl group
  • R 3 and Y are as defined above or in which R x represents either a (C 1 -C 4 ) straight or branched alkyl group, either a cyclo (C 3 -C 8 ) alkyl group, X a sulfur atom or
  • R 6 NCO for R 3 - C0NHR 6
  • R 3 CH ⁇ / NaBH 3 CN for R 3 arylalkyl
  • organometallic of formula R 1 CH 2 Cu (CN) ZnHal where Hal represents a halogen atom (for X -CH 2 -) and a compound of formula (le) is obtained which corresponds to a compound of formula (I) in which R represents a group -N0 2 .
  • a compound of formula (If) which corresponds to a compound of formula (I) in which R represents a group -NH 2 then we submit the compound of formula (le) corresponding to a hydrogenation, when X represents an atom of oxygen or a group -CH 2 -, -S0 2 - or -NR X -, or to a treatment with zinc in an acid medium when X represents a sulfur atom.
  • the compounds of formula (I) in which X represents a group -SO 2 - can also be prepared from the corresponding compound of formula (I) in which X represents a sulfur atom by treatment with 3-chloroperoxy-benzoic acid .
  • the starting compounds are commercially available or described in the literature or can be prepared according to methods which are described therein or which are known to those skilled in the art.
  • organometallics of formula R 1 CH 2 Cu (CN) ZnHal are prepared according to the method described by P. Knochel et al., Chemical Reviews, (1993), H, 2117.
  • the product obtained is hydrolyzed according to the procedure of Example 3 using 4.8 ml of a 1N aqueous sodium hydroxide solution. 1.1 g of product are obtained.
  • This compound is prepared from 5 g (13.4 mmol) of 6-methyl-3-nitro-2-oxo-4- [[(trifluoromethyl) sulfonyl] oxy] - 1,2-dihydropyridine-1-acetate methyl and 2.9 g (16.4 mmol) of 3-bromomethylthiophene according to the method described in 1.5.
  • This compound is prepared from 3.2 g (11 mmol) of
  • This compound is prepared from 5 g (13.4 mmol) of
  • Example 12 (Compound No. 42) 4- [[4- (1, 1-dimethylethyl) phenyl] methyl] -6-methyl -2 -oxo-3- [[(phenylmethoxy) carbonyl] amino] -1,2 -dihydropyridine-l- acetic
  • This compound is prepared from 11 g (29.4 mmol) of 6-methyl-3-nitro-2-oxo-4- [[(trifluoromethyl) sulfonyl] oxy] - 1, 2-dihydropyridine-1-acetate methyl and 10 g (52.9 mmol) of (4-fluorophenyl) methyl bromide according to the method described in 1.5.
  • Example 17 6-methyl-3-nitro-2-oxo-4- [[4- (trifluoromethyl) phenyl] methyl] -1,2-dihydropyridine-1-acetic acid
  • Example 19 (Compound No. 33) 4- [(4 -cyanophenyl) methyl] -3- [(methoxycarbonyl) amino] -6- methyl -2 -oxo-1,2-dihydropyridine- 1-acetic acid
  • This compound is prepared from 3 g (8 mmol) of 6-methyl -
  • Example 21 (compound 38) 4- (cyclohexylmethyl) -6-methyl-2 -oxo-3- [[(phenylmethoxy) carbonyl] amino] -1,2-dihydropyridine-1-acetic acid
  • 2-oxo-1,2-dihydropyridine-1-phenylmethyl acetate It is prepared from 6.6 g (14.6 mmol) of 6-methyl-3-nitro-2-oxo-4- [[(trifluoromethyl ) suifonyl] oxy] -1,2-dihydropyridin-1-phenylmethyl acetate and 4.58 g (20 mmol) of (4-methoxycarbonyl) phenylmethyl bromide according to the method described in Example 1.5, the addition of the intermediate zinc compound being carried out at -30 ° C.
  • Example 30 6-methyl-2-oxo-3- [[(phenylmethoxy) carbonyl] amino] -4- (phenylthio) -1,2-dihydropyridine-1-acetic acid
  • reaction medium is concentrated under vacuum and 8 ml of water and 5.8 ml of a 1N aqueous hydrochloric acid solution are added.
  • the precipitate is filtered, rinsed with water and dried under vacuum. . 1.39 g of product are obtained in the form of a pale yellow powder.
  • Example 33 (Compound No. 31) 3- [(methoxycarbonyl) amino] -6-methyl-2-oxo-4- (phenylsul-fonyl) -1,2-dihydropyridine-l-acetic acid
  • the compounds of formula (I) according to the invention are useful as synthesis intermediates.
  • R, R x and X are as defined above and R 9 and R ' 9 each independently of one another represent a hydrogen atom or a (C 1 -C 4 ) alkyl group.
  • R 9 and R ' 9 each independently of one another represent a hydrogen atom or a (C 1 -C 4 ) alkyl group.
  • a compound of formula (I) is reacted in which R, R ⁇ and X are as defined above and R 2 represents a hydrogen atom with N-hydroxysuccinimide in the presence of a coupling agent such as for example 1, 3-dicyclohexylcar-bodiimide to prepare a compound of formula (VII) which is condensed with a compound of formula (VIII) in which R 10 and R X1 together represent the residue of a dihydroxylated compound such as for example butane-2 , 3-diol, 2,3-dimethylbutane-2, 3-diol or (la, 3a, 5a) -2,6,6- trimethylbicyclo [3.1.1] heptane-2, 3-diol [(+) - ⁇ -pinanediol], in the presence of a base such as for example triethylamine and an intermediate compound is obtained which is treated with phenylboronic acid.
  • a base such as for example triethylamine and

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
EP98902060A 1997-01-16 1998-01-13 Pyridon-derivate, ihre herstellung und verwendung als zwischenprodukte in der synthese Ceased EP1019376A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9700378A FR2758326B1 (fr) 1997-01-16 1997-01-16 Derives de pyridone, leur prepaparation et leur utilisation comme intermediaires de synthese
FR9700378 1997-01-16
PCT/FR1998/000044 WO1998031671A1 (fr) 1997-01-16 1998-01-13 Derives de pyridone, leur preparation et leur utilisation comme intermediaires de synthese

Publications (1)

Publication Number Publication Date
EP1019376A1 true EP1019376A1 (de) 2000-07-19

Family

ID=9502640

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98902060A Ceased EP1019376A1 (de) 1997-01-16 1998-01-13 Pyridon-derivate, ihre herstellung und verwendung als zwischenprodukte in der synthese

Country Status (5)

Country Link
US (1) US6252082B1 (de)
EP (1) EP1019376A1 (de)
JP (1) JP2001513079A (de)
FR (1) FR2758326B1 (de)
WO (1) WO1998031671A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6867217B1 (en) * 1999-05-19 2005-03-15 Pharmacia Corporation Substituted polycyclic aryl and heteroaryl pyridones useful for selective inhibition of the coagulation cascade
US8034822B2 (en) * 2006-03-08 2011-10-11 Takeda San Diego, Inc. Glucokinase activators
JP5419706B2 (ja) * 2006-12-20 2014-02-19 タケダ カリフォルニア インコーポレイテッド グルコキナーゼアクチベーター
WO2008116107A2 (en) 2007-03-21 2008-09-25 Takeda San Diego, Inc. Piperazine derivatives as glucokinase activators

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2718448B3 (fr) * 1994-04-12 1996-02-09 Synthelabo Dérivés d'acides aminoboroniques, leur préparation et leur utilisation comme intermédiaires de synthèse.
FR2728570B1 (fr) * 1994-12-23 1997-04-11 Synthelabo Derives de 1-oxo-2-(phenylsulfonylamino)pentylpiperidine, leur preparation et leur application en therapeutique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9831671A1 *

Also Published As

Publication number Publication date
US6252082B1 (en) 2001-06-26
JP2001513079A (ja) 2001-08-28
WO1998031671A1 (fr) 1998-07-23
FR2758326B1 (fr) 1999-02-12
FR2758326A1 (fr) 1998-07-17

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