WO1997013768A1 - Composes derives d'oxazolidin-2-one, leur procede de preparation et leur application en therapeutique - Google Patents
Composes derives d'oxazolidin-2-one, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- WO1997013768A1 WO1997013768A1 PCT/FR1996/001511 FR9601511W WO9713768A1 WO 1997013768 A1 WO1997013768 A1 WO 1997013768A1 FR 9601511 W FR9601511 W FR 9601511W WO 9713768 A1 WO9713768 A1 WO 9713768A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- oxazolidin
- methoxymethyl
- mixture
- benzofuran
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- the subject of the present invention is compounds derived from oxazolidin-2-one of general formula (I)
- R 1 represents a hydrogen atom, an alkyl group
- R 4 is an alkyl group or a hydrogen atom
- an alkyl group is an aliphatic group, saturated
- an alkoxy group is an OR 5 group, where R 5 is an alkyl group as defined above, a fluoroalkyl group is an alkyl group as defined above, in which at least one of the carbon atoms is substituted by one or more fluorine atoms,
- a hydroxyfluoroalkyl group is a fluoroalkyl group as defined above, one of the carbon atoms of which is substituted by a hydroxy group,
- a cycloalkyl group is a radical derived from a
- cycloalkane comprising from 3 to 6 carbon atoms
- a cyclooxyalkyl group is a cycloalkyl group as defined above in which one of the carbon atoms is replaced by an oxygen atom as the hereroatom; the perhydrofuranyl and perhydropyranyl groups are representative of such a cyclooxyalkyl group,
- a cyanoalkyl group is an alkyl group as defined above, in which at least one of the carbon atoms is substituted by a nitrile group.
- R a has one of the meanings of R x chosen from a hydrogen atom an alkyl, fluoroalkyl, hydroxyfluoroalkyl, cyanoalkyl, R 3 A-, phenyl group substituted or not by a halogen atom, a nitro, nitrile or alkoxy and phenylmethyl group substituted or not by a halogen atom, a nitro, nitrile or alkoxy group.
- R 1 has one of the meanings of R 1 chosen from a hydrogen atom or an alkyl, fluoroalkyl, hydroxyalkyl, hydroxyfluoroalkyl, phenyl substituted or unsubstituted group by a halogen atom, a nitro, nitrile or alkoxy group or a phenylmethyl group substituted or not by a halogen atom, a nitro, nitrile or alkoxy group.
- R b Z is chosen from the group ethenyl, 2-phenylethenyl, 2-phenylethyl, 5,5,5-trifluoropentyl, 5,5,5-trifluoropentenyl, 5,5,5-trifluoro-4-hydroxypentyl and 5 , 5,5-trifluoro-4-hydroxypentenyl.
- the group R 1 Z advantageously represents a group R c O, where R c has one of the meanings of R 1 chosen from an alkyl, hydroxyalkyl, fluoroalkyl, hydroxyfluoroalkyl, phenyl group substituted or not by a halogen atom, a nitro, nitrile or alkoxy group or a phenylmethyl group substituted or not by a halogen atom or by an alkoxy, nitrile or nitro group.
- R c is chosen from the group consisting of butyl, 4,4,4-trifluorobutyl, 4,4,4-trifluoro-3-hydroxybutyl and the phenylmethyl group.
- R 4 is preferably a methyl group and the group R 1 Z advantageously represents a group R d O, where R d has one of the meanings of R 1 chosen from a fluoroalkyl or hydroxyfluoroalkyl group, a phenyl group substituted or not by a halogen atom, a nitro, nitrile or alkoxy group or a phenylmethyl group substituted or not by a halogen atom, a nitro, nitrile or alkoxy group.
- R d is chosen from the group consisting of 4,4,4-trifluorobutyl
- the compounds of formula (I) have one or two asymmetric carbon atoms. They can therefore exist in the form of enantiomers or pure diastereoisomers or as a mixture of these different forms, including as a racemic mixture. These different forms and their mixtures are part of the invention.
- the compounds of formula (I) in which R 1 Z represents a group R 1 -CH CH-, with the exception of the compounds in which R 1 is a hydrogen atom, exist in the form of cis or trans isomers. These forms, as well as their mixtures, form part of the invention.
- the compounds of the invention of formula (I) can be prepared according to the methods described in appendices 1 and 2.
- the compounds of formula (la), (Ib), (le), (Id) and (le), which are compounds of formula (I) according to the invention where Z represents an oxygen atom, can be prepared according to the process represented in appendix 1.
- X has one of the meanings given in formula (I ).
- an ethyl carbamate derivative of formula (II) is reacted with 4- (methoxymethyl) -1,3-dioxolan-2-one of formula (III) in the presence of potassium carbonate.
- R 1 and X have one of the meanings given in formula (I) with the exception, as regards R 1 , of hydrogen.
- This reaction makes it possible to obtain a compound of formula (la), which is a compound of formula (I) for which R 2 represents a methyl group and R 1 has one of the meanings given for formula (I), with the exception of hydrogen.
- the compounds of formula (la) where R 1 represents a phenylmethyl group can be used to prepare the compounds of formula (Ib).
- the latter are compounds of formula (I) for which R 2 represents a hydrogen atom and R 2 represents a methyl group.
- the phenylmethyl group is removed from said compound of formula (la), for example by means of dimethylphenylamine and aluminum chloride or by catalytic hydrogenation in the presence of palladium on carbon.
- the compounds of formula (Ib) can be used to prepare the compounds of formula (Ic).
- the latter are compounds of formula (I) for which R 1 and R 2 each represent a hydrogen atom.
- demethylation of a compound of formula (Ib) is carried out using a Lewis acid, such as boron tribromide, in a solvent such as dichloromethane.
- the compounds of formula (Ic) can in turn be used to prepare the compounds of formula (Id).
- the latter are compounds of formula (I) for which R 1 has one of the meanings given in formula (I), with the exception of the hydrogen atom, and R 2 is a hydrogen atom.
- reaction temperature may be the reflux temperature of the solvent.
- the compounds of formula (Ib) can be used to obtain compounds of formula (le) according to the invention for which R 1 has one of the meanings given in formula (I), except for the meaning hydrogen atom.
- a compound of formula (Ib) is reacted with a compound of formula R 1 Y, where R 1 has one of the meanings given in formula (I), with the exception of an atom of hydrogen, and Y is as defined above.
- This reaction can be carried out in the presence of a base such as potassium carbonate, in a solvent such as acetonitrile.
- the reaction temperature can be the reflux temperature of the solvent.
- the compound of formula (Ie) thus obtained can then be demethylated to prepare a compound of formula (Id).
- Demethylation can be carried out under the conditions indicated above as regards the demethylation of the compound of formula (Ib).
- the compounds of formula (I) for which the group R 1 is a group comprising a hydroxyl function can be prepared by reacting a compound of formula (II) comprising such a group R 1 with a compound of formula (III), said hydroxyl function being previously protected in a conventional manner for a person skilled in the art, by a protective group such as t-butyldimethylsilyl.
- a protective group such as t-butyldimethylsilyl.
- the protective group of the hydroxyl function can be eliminated by means, for example, of tetra-n-butylammonium fluoride, in an organic solvent such as tetrahydrofuran.
- a group -CH CH or -CH 2 -CH 2 , can be prepared according to the process represented in appendix 2.
- X has one of the meanings indicated in formula (I).
- the compound of formula (IV) can then be reacted with palladium acetate in the presence of carbon monoxide and methanol to prepare a methoxycarbonyl derivative of formula (V), which is in turn treated using 'a
- triphenylphosphonium such as a triphenylphosphonium bromide, where R 1 has one of the meanings given in formula (I) and W- represents the anion of a halogen atom.
- the compound of formula (If) can then be reduced to prepare a compound according to the invention of formula (Ig). This reduction can be carried out using hydrogen in the presence of a catalyst such as palladium on carbon.
- the compounds of formula (If) and (Ig) can be demethylated to yield the corresponding compounds of formula (I) where R 2 represents a hydrogen atom. This demethylation can be done using a Lewis acid such as boron tribromide.
- the compounds of formula (II) can be prepared according to the process represented in appendix 3, by reacting a compound of formula (VIII) with a compound of formula R 1 Y, in which R 1 is defined as in formula (I) and Y is a halogen atom, in particular bromine, or a labile group such as methylsulfonyloxy (mesyloxy) or p-toluenesulfonyloxy (tosyloxy).
- This reaction can be carried out in the presence a base such as potassium carbonate, in a solvent such as acetonitrile.
- the reaction temperature can be the reflux temperature of the solvent.
- the compound of formula (VIII) can be prepared from a compound of formula (IX), where R 6 is a protecting group for the hydroxy group, in particular a methyl or phenylmethyl group.
- R 6 is a protecting group for the hydroxy group, in particular a methyl or phenylmethyl group.
- said protective group R 6 is eliminated by conventional means for those skilled in the art.
- the compound of formula (IX) is demethylated using a Lewis acid such as boron tribromide, in an organic solvent such as dichloromethane.
- the temperature used during this treatment can be between -20 ° C and 20 ° C.
- R 6 is a phenylmethyl group
- this protective group can be removed by catalytic hydrogenation.
- the compound of formula (IX) can be prepared by
- the compound of formula (X) can be prepared by
- the saponification reaction can be carried out at a base such as potassium hydroxide in an alcoholic medium.
- the saponification reaction can be carried out at a base such as potassium hydroxide in an alcoholic medium.
- R 7 represents a methyl or ethyl group.
- the compound of formula (XI) can be prepared by reacting a compound of formula (XII), where R 7 represents a methyl or ethyl group, with ethyl chloroformate. This reaction can be carried out in the presence of a base such as potassium carbonate, in a solvent such as toluene. This reaction can be carried out at the reflux temperature of the solvent.
- a base such as potassium carbonate
- X has one of the meanings given in formula (I).
- the compounds of formula (XII) can be prepared according to various synthetic routes according to the nature of X. These synthetic routes are represented in Annex 4.
- the compounds of formula (XII) where X is a sulfur atom and R 6 and R 7 each represent a methyl group can be prepared by reacting 3-nitro-4-cyanoanisole with methyl thioglycolate. This reaction can be carried out in the presence of a base such as potassium hydroxide, in a solvent such as N, N-dimethylformamide. This reaction can be carried out at 0oC.
- 3-nitro-4-cyanoanisole is a known compound. It can be prepared according to the method described by A.H. Cook et al., J.
- the compounds of formula (XII) for which X is an oxygen atom or ⁇ R 4 can be prepared by a process according to which a compound of formula (XIII) is treated, either by sodium ethylate when X represents an oxygen atom, or by potassium tert-butoxide when X represents NR 4 .
- the compound of formula (XIII) can be prepared by reacting a compound of formula (XIV), where X is an oxygen atom or NR 4 , with sodium hydride then bromoacetate
- a compound of formula (XIV) where X is an oxygen atom can be prepared by reacting 2-hydroxy-4- (phenylmethoxy) benzaldehyde with nitroethane or hydroxylamine and ethyl formate.
- 2-hydroxy-4- (phenylmethoxy) benzaldehyde is a known compound, which can be prepared according to JSH Davies (J. Chem. Soc. 1950, 3206).
- a compound of formula (XIV) where X is an NR 4 group can be prepared by reacting a compound of formula (XV) with a compound of formula R 4 NH 2 , such as methylamine.
- the compound of formula (XV) can itself be obtained by reacting commercially available 2-fluoro-4- (hydroxy) benzonitrile with benzyl bromide.
- R 4 has one of the meanings given for formula (I).
- the enantiomers 5 (R) and 5 (S) of the compounds of formula (I) are prepared respectively from the enantiomers (S) and (R) of 4-methoxymethyl-1,3-dioxolane-2-one of formula ( III), according to the method described above.
- (R) -4-methoxymethyl-1,3-dioxolane-2-one is prepared according to the same method, starting from (R) -2,2-dimethyl-1,3-dioxolan-4-methanol.
- the dash "-" is part of the word, and the dash “-” is only used for the break at the end of the line; it must be deleted in the absence of a break, and must not be replaced either by a normal dash or by a space.
- Example 3 (R) -5- (hydroxymethyl) -3- (6-hydroxybenzofuran-3-yl) oxazolidin-2-one To a solution of 1.5 g (5.7 mol) of (R) -5- (methoxymethyl) -3- (6-hydroxybenzofuran-3-yl) oxazolidin-2-one in 100 ml of dichloromethane cooled to 0 ° C, 17 ml of a 1M solution of boron tribromide in dichloromethane are added. The reaction medium is stirred for 2 hours then it is poured into an ammonia solution. The product is then extracted with dichloromethane, then the organic phase is washed with water, dried over sodium sulfate and concentrated under reduced pressure. After chromatography of the residue on a silica column with a mixture of 4% methanol in dichloromethane and trituration in diethyl ether, 0.80 g of product is obtained.
- the product is purified by chromatography on silica gel with a mixture of dichloromethane and methanol 99/1.
- Example 11 (R) -5- (methoxymethyl) -3- [6- (5,5,5-trifluoro pentyl) benzofuran-3-yl] oxazolidin-2-one
- dichloromethane 46 ml of a 1M solution of boron tribromide (0.046 mole) in dichloromethane, while maintaining the temperature at 0 ° C.
- the mixture is allowed to return to ambient temperature and 15 ml of a 1M solution of boron tribromide (0.015 mol) in dichloromethane are added.
- the mixture is stirred for 180 min., Then it is neutralized with a dilute ammonium hydroxide solution and the precipitate obtained is filtered. The latter is washed with water and dried. Purified by chromatography on a column of silica gel with
- the mixture is heated at 140 ° C. for five hours, a mixture
- Example 17 ⁇ R) -5- (methoxymethyl) -3- [1-methyl-6- (phenylmethoxy) -1H-indol-3-yl] oxazolidin-2-one
- the mixture is brought to reflux temperature for two hours, a mixture of 40.8 g (0.297 mole) of 2-fluoro-4-hydroxybenzonitrile, 61.06 g (0.357 mole) of benzyl bromide and 82 g (0.594 mole) of potassium carbonate in 400 ml of acetonitrile.
- the mixture is filtered, the solvent is evaporated off under reduced pressure and the evaporation residue is triturated with diisopropyl ether.
- reaction mixture is taken up with dichloromethane, the organic phase is washed three times with water and dried over sodium sulfate. The solvent is then evaporated off under reduced pressure and 32.9 g of product are recovered.
- the catalytic hydrogenation is carried out of a solution of 1 g (0.0027 mol) of (S) -5- (methoxymethyl) -3- [1-methyl-6- (phenylmethoxy) -1H-indol-3- yl] oxazolidin-2-one, obtained in Example 17, in a mixture of 15 ml of N, N-dimethylformamide and 15 ml of ethanol.
- the hydrogenation is carried out in 18 hours, under normal hydrogen pressure, in presence of 0.2 g of palladium on carbon.
- reaction medium is filtered to remove the palladium on carbon, the solvent is evaporated off under reduced pressure and 0.53 g of product in the form of a gum is recovered.
- the compounds of the invention have been the subject of pharmacological tests making it possible to determine their inhibitory power of monoamine oxidase A and of monoamine oxidase B.
- the reaction is
- radioactive metabolites resulting from oxidative deamination are then separated from the untransformed substrate, by extraction in organic phase, and quantified by counting the radioactivity.
- the inhibitory activities with respect to MAO-A and MAO-B are given respectively by the inhibition constants Ki (MAO-A) and Ki (MAO-B).
- the Ki (MAO-A) vary between 1.2 nM and values greater than 1000 nM, while the Ki (MAO-B) vary between 0.3 nM and values
- Certain compounds of the invention are selective MAO-B inhibitors, the Ki (MAO-A) / Ki (MAO-B) ratio possibly being greater than 10 3 .
- Certain compounds of the invention are selective MAO-A inhibitors, the Ki (MAO-B) / Ki (MAO-A) ratio may be greater than 10 3 .
- Ki (MAO-A) / Ki (MAO-B) ratio can be between 0.1 and 10.
- the invention can be used for the preparation of drugs which are selective inhibitors of MAO-A or MAO-B or mixed inhibitors of MAO-A and MAO-B, these drugs finding their use in therapeutics in particular in the treatment depressive states of any kind, senile depressive psychoses, hypobulia, social phobias, mood disorders, in improving general brain performance, in preventing and treating neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease and all memory disorders, in anxiety, panic attacks, treatment of dependence and withdrawal related to
- the compounds of the invention may be presented, in combination with excipients, in the form of compositions formulated for oral administration,
- parenteral or rectal for example in the form of tablets, dragees, capsules, solutions, suspensions or suppositories.
- the dose of active ingredient administered is generally between 0.01 and 50 mg / kg / day, in one or more doses.
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96932663A EP0891358A1 (fr) | 1995-10-11 | 1996-10-08 | Composes derives d'oxazolidin-2-one, leur procede de preparation et leur application en therapeutique |
JP9514756A JPH11513400A (ja) | 1995-10-11 | 1996-10-08 | オキサゾリジン−2−オンから誘導される化合物、それらの製造法およびそれらの治療への応用 |
US09/051,539 US5969146A (en) | 1995-10-11 | 1996-10-08 | Oxazolidin-2-one derivatives, preparation method therefor and therapeutical use thereof |
AU71359/96A AU7135996A (en) | 1995-10-11 | 1996-10-08 | Oxazolidin-2-one derivatives, preparation method therefor and therapeutical use thereof |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9511902A FR2739856B1 (fr) | 1995-10-11 | 1995-10-11 | Derives de 3-benzofuranyloxazolidin-2-one, leur procede de preparation et leur application en therapeutique |
FR95/11902 | 1995-10-11 | ||
FR9609361A FR2751651B1 (fr) | 1996-07-25 | 1996-07-25 | Derives de 3-(benzo[b]thien-3-yl)oxazolidin-2-one, leur procede de preparation et leur application en therapeutique |
FR9609362A FR2751653B1 (fr) | 1996-07-25 | 1996-07-25 | Derives de 3-benzofuranyloxazolidin-2-one, leur procede de preparation et leur application en therapeutique |
FR96/09362 | 1996-07-25 | ||
FR96/09361 | 1996-07-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997013768A1 true WO1997013768A1 (fr) | 1997-04-17 |
Family
ID=27253110
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1996/001511 WO1997013768A1 (fr) | 1995-10-11 | 1996-10-08 | Composes derives d'oxazolidin-2-one, leur procede de preparation et leur application en therapeutique |
Country Status (6)
Country | Link |
---|---|
US (1) | US5969146A (fr) |
EP (1) | EP0891358A1 (fr) |
JP (1) | JPH11513400A (fr) |
AU (1) | AU7135996A (fr) |
TW (1) | TW336234B (fr) |
WO (1) | WO1997013768A1 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001012176A2 (fr) * | 1999-08-16 | 2001-02-22 | Sanofi-Synthelabo | Utilisation d'inhibiteurs de la monoamine oxidase dans la fabrication de medicaments destines a traiter l'obesite |
FR2823208A1 (fr) * | 2001-04-10 | 2002-10-11 | Sod Conseils Rech Applic | Derives d'heterocycles a 5 chainons, leur preparation et leur application a titre de medicaments |
WO2002083656A2 (fr) * | 2001-04-10 | 2002-10-24 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Derives d'heterocycles a 5 chainons et leur utilisation en tant qu'inhibiteurs de la mao et/ou peroxydation lipidique, leur preparation et leur application comme medicaments |
WO2003091215A1 (fr) * | 2002-04-23 | 2003-11-06 | Aventis Pharmaceuticals Inc. | Acide amino-1h-indole-2-carboxylique 3-substitue et derives d'acide amino-benzo' b! thiophene-2-carboxylique substitue utilises comme inhibiteurs d'expression genique d'interleukine 4 |
US7169925B2 (en) | 2002-04-23 | 2007-01-30 | Aventis Pharmaceuticals Inc. | Indole derivatives as interleukin-4 gene expression inhibitors |
CN102267990A (zh) * | 2011-06-03 | 2011-12-07 | 浙江工业大学 | 一种2,3-二氢苯并呋喃类衍生物及其制备与应用 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3334595B2 (ja) | 1998-03-10 | 2002-10-15 | ダイソー株式会社 | オキサゾリジン−2−オン誘導体の製造法 |
Citations (3)
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EP0006524A1 (fr) * | 1978-06-22 | 1980-01-09 | Ciba-Geigy Ag | Dérivés de tétrahydropyridine et de tétrahydropipéridine, leurs sels d'addition acides, procédés pour leur préparation et compositions pharmaceutiques les contenant |
EP0657440A1 (fr) * | 1993-12-13 | 1995-06-14 | F. Hoffmann-La Roche Ag | Dérivés d'oxazolidine-2-one |
DE4425609A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Benzofuranyl- und Benzothienyloxazolidinone |
Family Cites Families (1)
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US5347013A (en) * | 1991-03-28 | 1994-09-13 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles |
-
1996
- 1996-10-08 WO PCT/FR1996/001511 patent/WO1997013768A1/fr not_active Application Discontinuation
- 1996-10-08 US US09/051,539 patent/US5969146A/en not_active Expired - Fee Related
- 1996-10-08 JP JP9514756A patent/JPH11513400A/ja active Pending
- 1996-10-08 AU AU71359/96A patent/AU7135996A/en not_active Abandoned
- 1996-10-08 EP EP96932663A patent/EP0891358A1/fr not_active Withdrawn
- 1996-10-09 TW TW085112325A patent/TW336234B/zh active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0006524A1 (fr) * | 1978-06-22 | 1980-01-09 | Ciba-Geigy Ag | Dérivés de tétrahydropyridine et de tétrahydropipéridine, leurs sels d'addition acides, procédés pour leur préparation et compositions pharmaceutiques les contenant |
EP0657440A1 (fr) * | 1993-12-13 | 1995-06-14 | F. Hoffmann-La Roche Ag | Dérivés d'oxazolidine-2-one |
DE4425609A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Benzofuranyl- und Benzothienyloxazolidinone |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1078632A1 (fr) * | 1999-08-16 | 2001-02-28 | Sanofi-Synthelabo | Utilisation des inhibiteurs de monoamine oxydases dans la fabrication d'un médicament contre l'obésité |
WO2001012176A3 (fr) * | 1999-08-16 | 2002-03-21 | Sanofi Synthelabo | Utilisation d'inhibiteurs de la monoamine oxidase dans la fabrication de medicaments destines a traiter l'obesite |
WO2001012176A2 (fr) * | 1999-08-16 | 2001-02-22 | Sanofi-Synthelabo | Utilisation d'inhibiteurs de la monoamine oxidase dans la fabrication de medicaments destines a traiter l'obesite |
KR100865809B1 (ko) * | 2001-04-10 | 2008-10-28 | 소시에떼 드 꽁세이으 드 르세르세 에 따블리까시옹 시앙띠피끄 (에스.세.에르.아.에스.) | 5-원 헤테로사이클, 이의 제조 방법 및 의약으로서의 이의용도 |
FR2823208A1 (fr) * | 2001-04-10 | 2002-10-11 | Sod Conseils Rech Applic | Derives d'heterocycles a 5 chainons, leur preparation et leur application a titre de medicaments |
WO2002083656A2 (fr) * | 2001-04-10 | 2002-10-24 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Derives d'heterocycles a 5 chainons et leur utilisation en tant qu'inhibiteurs de la mao et/ou peroxydation lipidique, leur preparation et leur application comme medicaments |
WO2002083656A3 (fr) * | 2001-04-10 | 2003-01-03 | Sod Conseils Rech Applic | Derives d'heterocycles a 5 chainons et leur utilisation en tant qu'inhibiteurs de la mao et/ou peroxydation lipidique, leur preparation et leur application comme medicaments |
WO2003091215A1 (fr) * | 2002-04-23 | 2003-11-06 | Aventis Pharmaceuticals Inc. | Acide amino-1h-indole-2-carboxylique 3-substitue et derives d'acide amino-benzo' b! thiophene-2-carboxylique substitue utilises comme inhibiteurs d'expression genique d'interleukine 4 |
EP1834947A2 (fr) * | 2002-04-23 | 2007-09-19 | Aventis Pharmaceuticals, Inc. | Dérivés d'acide 3-amino-1H-indole-2-carboxylique et d'acide 3-amino-benzo[B]thiophène-2-carboxylique utiles comme inhibiteurs de l'expression du gène de l'interleukine-4 |
EP1834947A3 (fr) * | 2002-04-23 | 2008-05-28 | Aventis Pharmaceuticals, Inc. | Dérivés d'acide 3-amino-1h-indole-2-carboxylique et d'acide 3-amino-benzo[b]thiophène-2-carboxylique utiles comme inhibiteurs de l' expression du gène de l' interleukine-4 |
US7169925B2 (en) | 2002-04-23 | 2007-01-30 | Aventis Pharmaceuticals Inc. | Indole derivatives as interleukin-4 gene expression inhibitors |
CN102267990A (zh) * | 2011-06-03 | 2011-12-07 | 浙江工业大学 | 一种2,3-二氢苯并呋喃类衍生物及其制备与应用 |
CN102267990B (zh) * | 2011-06-03 | 2013-11-13 | 浙江工业大学 | 一种2,3-二氢苯并呋喃类衍生物及其制备与应用 |
Also Published As
Publication number | Publication date |
---|---|
AU7135996A (en) | 1997-04-30 |
TW336234B (en) | 1998-07-11 |
JPH11513400A (ja) | 1999-11-16 |
EP0891358A1 (fr) | 1999-01-20 |
US5969146A (en) | 1999-10-19 |
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