WO2004020430A2 - Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique - Google Patents
Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique Download PDFInfo
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- WO2004020430A2 WO2004020430A2 PCT/FR2003/002590 FR0302590W WO2004020430A2 WO 2004020430 A2 WO2004020430 A2 WO 2004020430A2 FR 0302590 W FR0302590 W FR 0302590W WO 2004020430 A2 WO2004020430 A2 WO 2004020430A2
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- dioxan
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Definitions
- the subject of the invention is derivatives of 1,3-dioxan-2-ylalkylcarbamates, their preparation and their therapeutic use.
- Ri represents a phenyl or naphthalenyl group optionally substituted by one or more halogen atoms or hydroxy, cyano, nitro, C ⁇ _ 3 -alkyle, C ⁇ - 3 -alkoxy, trifluoromethyl, trifluoromethoxy, benzyloxy,
- R 2 represents either a group of general formula CHR 3 CONHR 4 in which R 3 represents a hydrogen atom or a methyl group and R 4 represents a hydrogen atom or a C ⁇ _ 3 -alkyle, C 3 - 5 -cycloalkyle group or (pyridin-4-yl) methyl, either a 2, 2, 2-trifluoroethyl group, or a (imidazol-2-yl) methyl group, or a (benzimidazol-2-yl) methyl group, or a phenyl group optionally substituted by one or more halogen atoms or cyano, nitro groups,
- n represents a number ranging from 1 to 3.
- the compounds of general formula (I) may contain one or more asymmetric carbons. They can exist in the form of enanti ers or diastereoisomers. The compounds of general formula (I) can also exist in the form of cis or trans stereoisomers. These enantiomers, diastereoisomers and stereoisomers, as well as their mixtures, including racemic mixtures, form part of the invention.
- the compounds of formula (I) can exist in the form of bases or of addition salts with acids. Such addition salts form part of the invention.
- salts are advantageously prepared with pharmaceutically acceptable acids, but the salts of other acids useful, for example, for the purification or isolation of the compounds of formula (I) also form part of the invention.
- the compounds of general formula (I) can be in the form of hydrates or solvates, namely in the form of associations or combinations with one or more molecules of water or with a solvent. Such hydrates and solvates are also part of the invention.
- a carbon chain can have from t to z carbon atoms, for example C ⁇ _ 3 a carbon chain which can have from 1 to 3 carbon atoms;
- Cycloalkyl, a cyclic alkyl group for example, a group C 3 ⁇ 5 -cycloalkyle represents a cyclic carbon chain of 3 to 5 carbon atoms, more particularly a cyclopropyl, cyclobutyl, cyclopentyl;
- alkoxy an alkyloxy group with a saturated aliphatic chain, linear or branched
- Ri represents a naphthalenyl group, optionally substituted by one or more halogen atoms or hydroxy, cyano, nitro, C ⁇ _ 3 -alkyle, C ⁇ _ 3 -alkoxy, trifluoromethyl, trifluoromethoxy, benzyloxy, C 3 _ 6 -cycloalkyl-0- or C 3 _ 6 -cycloalkylC ⁇ - 3 -alkoxy; and / or R 2 represents either a group of general formula CHR 3 CONHR in which R 3 represents a hydrogen atom and
- R represents a hydrogen atom or a C ⁇ _ 3 -alkyl group, preferably a methyl or an ethyl, or (pyridin-4-yl) methyl, either a 2, 2, 2-trifluoroethyl group, or an optionally substituted phenyl group by one or more halogen atoms or cyano, nitro, C ⁇ _ 3 -alkyle, C ⁇ _ 3 -alkoxy, trifluoromethyl or trifluoromethoxy groups; and / or n represents 2 or 3.
- 2-amino-2-oxoethyl propylcarbamate trans-3- [5- (naphthalen-1-yl) -1, 3-dioxan-2-yl] .
- fcrans-2- [5- (naphthalen-1-yl) -1, 3-dioxan-2-yl] ethylcarbamate of 2- (methylamino) -2-oxoethyl.
- trans-3 [5- (6-hydroxynaphthalen-1-yl) -1, 3-dioxan-2- yljpropylcarbamate of 2- (methylamino) -2-oxoethyl.
- trans-3 [5- (7-methoxynaphthalen-1-yl) -1, 3-dioxan-2-yljpropylcarbamate of 2-amino-2-oxoethyl.
- trans-3 [5- (7-methoxynaphthalen-1-yl) -1, 3-dioxan-2-yljpropylcarbamate of 2- (methylamino) -2-oxoethyl.
- trans-3 [5- (naphthalen-2-yl) -1, 3-dioxan-2-ylj 2- (methylamino) -2-oxoethyl ropylcarbamate.
- trans-3- [5- (naphthalen-2-yl) -1, 3-dioxan-2-yljpropylcarbamate of 2, 2, 2-trifluoroethyl.
- the compounds of the invention can be prepared according to various methods, illustrated by the schemes which follow.
- a preparation method (scheme 1) consists in reacting an amine of general formula (II), in which Ri and n are as defined in general formula (I), with a carbonate of general formula (III), in which U represents a hydrogen atom or a nitro group and R is as defined in general formula (I), in a solvent such as toluene or dichloroethane, at a temperature between 0 and 80 ° C.
- the carbonates of general formula (III) can be prepared according to any method described in the literature, by example by reaction of an alcohol of general formula HOR with phenyl or 4-nitrophenyl chloroformate, in the presence of a base such as triethylamine or diisopropylethylamine.
- the compounds of general formula (I) for which R 2 more particularly represents an optionally substituted phenyl group (Ar) can be prepared by reacting an ine of general formula (II), as defined above, with a chloroformate d aryl of general formula (IIIa) in a solvent such as dichloromethane or dichloroethane in the presence of a base such as triethylamine or diisopropylethylamine, at a temperature between 0 ° C and the reflux temperature of the solvent.
- the compounds of general formula (I) for which R 2 more particularly represents a group of general formula CHR 3 CONHR can be prepared by reacting a compound of general formula (II), as defined above , with carbon dioxide in the presence of a base such as cesium carbonate and a phase transfer agent such as tetra-n-butylammonium iodide, in a solvent such as N, N-dimethylformamide or N-methylpyrrolidone, then with a haloacetamide of general formula (IV) in which V represents a chlorine, bromine or iodine atom and R 3 and R 4 are as defined in the general formula (I).
- Diagram 2
- a variant (scheme 3) for obtaining the compounds of general formula (I) in which R 2 more particularly represents a group of general formula CHR 3 CONHR 4 consists in reacting an amine of general formula (II), as defined above above, with a carbonate of general formula (IIIb) in which U represents a hydrogen atom or a nitro group, R 3 is as defined in the general formula (I) and R5 represents a methyl or ethyl group.
- the carbamate ester of general formula (la) thus obtained is then transformed into compound of general formula (I), either by direct aminolysis using an amine of general formula RNH 2 in which R 4 is as defined in the formula general (I), either by hydrolysis to acid of general formula (la), in which R5 represents a hydrogen atom, followed by coupling with an amine of general formula R 4 NH 2 in which R is as defined in the general formula (I).
- the aminolysis reaction can be carried out in a solvent such as methanol or a mixture of solvents such as methanol and tetrahydrofan.
- the coupling reaction can be carried out according to any method known from the literature, for example with the use of isobutyl chloroformate, in the presence of a base such as diisopropylethylamine.
- the carbonates of general formula (IIIb) can be prepared in a similar manner to the carbonates of formula (III).
- Another variant (scheme 4) for obtaining the compounds of general formula (I) in which R more particularly represents a group of general formula CHR 3 CONHR 4 consists in reacting a derivative of general formula (IIa) in which Z represents a hydroxyl group, mesylate, tosylate, or a chlorine, bromine or iodine atom, Ri and n are as defined in general formula (I), with an oxazolidine-dione of general structure (V) in which R 3 is as defined in the general formula (I), to provide the oxazolidine-dione derivative of general structure (VI).
- the reaction can be carried out according to the Mitsunobu conditions
- the amines of general formula (II) can be prepared according to the preparation methods described in patent applications EP0461958, WO97 / 20836, WO98 / 55474, optionally adapted according to techniques known to those skilled in the art.
- the compounds of general formula (la), in which Ri, R 3 and n are as defined in general formula (I) and R5 represents a hydrogen atom, a methyl or ethyl group, and the compounds of general formula ( VI), in which Ri, R 3 and n are as defined in the general formula (I), are new and also form part of the invention. They are useful as synthesis intermediates for the preparation of the compounds of general formula (I).
- Example 1 (Compound No. 61). trans-3- [5- (6-methoxynaphthalen-1-yl) -1, 3-dioxan-2- yljpropylcarbamate of 2- (cyclopropylamino) -2-oxoethyl.
- Example 2 (Compound No. 49). trans-3- [5- (6-methoxynaphthalen-1-yl) -1, 3-dioxan-2-y1] 2-amino-2-oxoethyl propyl carbamate.
- Example 5 (Compound No. 46). fcrans-3- [5- (4-chloronaphthalen-1-yl) -1, 3-dioxan-2-yl] 2-amino-2-oxoethyl propylcarbamate.
- the residue is taken up in 100 ml of ethyl acetate and 25 ml of water. We decant. The organic phase is washed with 25 ml of water and then 25 ml of a saturated aqueous solution of sodium chloride. The aqueous phases are re-extracted with 50 ml of ethyl acetate. The organic phases are combined, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by chromatography on silica gel, eluting with a 70/30 then 60/40 mixture of cyclohexane and ethyl acetate to obtain 0.483 g of product in the form of a white solid. Melting point: 125-127 ° C.
- Example 6 (Compound No. 67) fcrans-3- [5- (6-cyclopropylmethoxy-naphthalen-1-yl) -1, 3-dioxan-
- the following table illustrates the chemical structures and the physical properties of some compounds according to the invention.
- the compounds in the table show the relative configuration trans on the dioxane ring with the exception of compounds n ° 37 and 50 which has the relative cis configuration and the compounds n ° 6, 9, 11, 13, 18, 20, 21 and 43 which are in the form of a mixture cis and trans stereoisomers. All of the compounds in the table are in the form of bases.
- the compounds of the invention have been the subject of pharmacological tests which make it possible to determine their inhibitory effect on the enzyme FAAH (Fatty Acid Amido Hydrolase).
- the inhibitory activity was demonstrated in a radioenzymatic test based on the measurement of the hydrolysis product (ethanolamine [1- 3 H]) of anandamide [ethanolamine 1- 3 H] by FAAH (Life Sciences (1995 ), 56, 1999-2005 and Journal of Pharmacology and Experimented Therapeutics (1997), 283, 729-734).
- mouse brains minus the cerebellum
- the membrane homogenates are prepared extemporaneously by homogenization of the tissues with Polytron in a Tris-HCl 10 M buffer (pH 8.0) containing 150 mM NaCl and 1 mM EDTA.
- the enzymatic reaction is then carried out in 70 ⁇ l of buffer containing bovine serum albumin without fatty acids (1 mg / ml).
- the compounds tested at different concentrations are successively added, anandamide [ethanolamine 1 - 3 H] (specific activity of 15-20 Ci / mmol) diluted to 10 ⁇ M with non-radiolabelled anandamide and the membrane preparation (400 ⁇ g tissue frozen by test).
- anandamide [ethanolamine 1 - 3 H] (specific activity of 15-20 Ci / mmol) diluted to 10 ⁇ M with non-radiolabelled anandamide and the membrane preparation (400 ⁇ g tissue frozen by test).
- the enzymatic reaction is stopped by adding 140 ⁇ L of chloroform / methanol (2: 1). The mixture is stirred for 10 minutes and then centrifuged for 15 minutes at 3500 g.
- the in vivo activity of the compounds of the invention was evaluated in an analgesia test.
- PBQ phenylbenzoquinone, 2 g / kg in a 0.9% NaCl solution containing 5% ethanol
- the test compounds are administered orally or i.p. suspended in 0.5% Tween 80, 30 minutes, 60 minutes or 120 minutes before administration of PBQ.
- Tween 80 0.5% Tween 80
- the most powerful compounds of the invention reduce from 50 to 70% the number of stretches induced by PBQ, in a range of doses between 1 and 30 mg / kg.
- the FAAH enzyme (Chemistry and Physics of Lipids, (2000), 108, 107-121) catalyzes the hydrolysis of endogenous derivatives of amides and esters of different fatty acids such as N-arachidonoylethanolamine (anandamide), N-palmitoylethanolamine, N-oleoylethanolamine, oleamide or 2-arachidonoylglycerol. These derivatives exercise different pharmacological activities by interacting, among others, with the cannabinoid and vanilloid receptors.
- the compounds of the invention block this degradation pathway and increase the tissue level of these endogenous substances. They can be used as such in the prevention and treatment of any pathology in which endogenous cannabinoids and / or any other substrate metabolized by the enzyme FAAH, are involved.
- pain in particular acute or chronic pain of the neurogenic type: migraine, neuropathic pain including the forms associated with the herpes virus and with diabetes; acute or chronic pain associated with inflammatory diseases: arthritis, rheumatoid arthritis, osteoarthritis, spondylitis, gout, vasculitis, Crohn's disease, irritable bowel syndrome; acute or chronic peripheral pain; dizziness, vomiting, nausea especially those following chemotherapy; eating disorders, in particular anorexia and cachexia of various kinds; neurological and psychiatric pathologies: tremors, dyskinesias, dystonias, spasticity, compulsive and obsessive behaviors, Tourette syndrome, all forms of depression and anxiety of any kind and origin, mood disorders, psychoses; acute or chronic neurodegenerative diseases: Parkinson's disease, Alzheimer's disease, senile dementia, Huntington's chorea, lesions linked to cerebral ischemia and to head and spinal cord injuries; epilepsy; sleep
- the invention also relates to medicaments which comprise a compound of formula (I), or a salt, or alternatively a hydrate or a pharmaceutically acceptable solvate of the compound of formula (I). These drugs find their use in therapy, especially in the prevention and treatment of the pathologies mentioned above.
- the present invention relates to pharmaceutical compositions containing, as active principle, at least one compound according to the invention.
- These pharmaceutical compositions contain an effective dose of a compound according to the invention, or a salt, or a hydrate, or a pharmaceutically acceptable solvate of said compound, and optionally one or more pharmaceutically acceptable excipients.
- Said excipients are chosen according to the pharmaceutical form and the desired mode of administration, from the usual excipients which are known to those skilled in the art.
- compositions of the present invention for oral, sublingual, subcutaneous, intramuscular, intravenous, topical, local, intrathecal, intranasal, transdermal, pulmonary, ocular or rectal administration the active principle of formula (I) above, or its salt, solvate or optional hydrate, can be administered in unit administration form, in admixture with conventional pharmaceutical excipients, to animals and humans for the prevention or treatment of the above disorders or diseases above mentioned.
- Suitable unit dosage forms include oral forms such as tablets, soft or hard capsules, powders, granules, chewing gum and oral solutions or suspensions, sublingual, buccal forms of administration, intratracheal, intraocular, intranasal, inhalation, subcutaneous, intramuscular, intravenous or intrathecal administration forms and rectal or vaginal administration forms.
- oral forms such as tablets, soft or hard capsules, powders, granules, chewing gum and oral solutions or suspensions, sublingual, buccal forms of administration, intratracheal, intraocular, intranasal, inhalation, subcutaneous, intramuscular, intravenous or intrathecal administration forms and rectal or vaginal administration forms.
- the compounds according to the invention can be used in creams, ointments or lotions.
- a unit form of administration of a compound according to the invention in tablet form can comprise the following components:
- Said unit forms are dosed to allow daily administration of 0.01 to 20 mg of active principle per kg of body weight, depending on the dosage form.
- the appropriate dosage for each patient is determined by the doctor according to the method of administration, the weight and the response of said patient.
- the invention according to another of its aspects, also relates to a method of treatment of the pathologies indicated above which comprises the administration of an effective dose of a compound according to the invention, of one of these pharmaceutically acceptable salts, a solvate or a hydrate of said compound.
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Abstract
Description
Claims
Priority Applications (31)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EA200500268A EA008218B1 (ru) | 2002-08-29 | 2003-08-27 | Производные диоксан-2-алкилкарбамата, способ их получения и применение в терапии |
AU2003274292A AU2003274292B2 (en) | 2002-08-29 | 2003-08-27 | Derivatives of dioxane-2-alkyl carbamates, preparation method thereof and application of same in therapeutics |
MEP-242/08A MEP24208A (en) | 2002-08-29 | 2003-08-27 | Derivatives of dioxane-2-alkyl carbamates, preparation method thereof and application of same in therapeutics |
JP2004532233A JP4585854B2 (ja) | 2002-08-29 | 2003-08-27 | ジオキサン−2−アルキルカルバメート誘導体、その製造法および治療における適用 |
KR1020057003244A KR101051192B1 (ko) | 2002-08-29 | 2003-08-27 | 디옥산-2-알킬 카르바메이트의 유도체, 그의 제조 방법 및치료법에서의 그의 적용 |
MXPA05002319A MXPA05002319A (es) | 2002-08-29 | 2003-08-27 | Derivados de dioxan-2-alquilcarbamatos, su preparacion y su aplicacion en terapeutica. |
DK07013954T DK1840125T3 (da) | 2002-08-29 | 2003-08-27 | Mellemprodukter til fremstilling af dioxan-2-alkylcarbamater |
YUP-2005/0182A RS51085B (sr) | 2002-08-29 | 2003-08-27 | Derivati dioksan-2-alkilkarbamata, postupak za njihovo dobijanje i primena istih u terapeuticima |
CA2496040A CA2496040C (fr) | 2002-08-29 | 2003-08-27 | Derives de carbamates de dioxan-2-alkyle, methode de preparation connexe et utilisation desdits derives en therapeutique |
SI200331438T SI1537096T1 (sl) | 2002-08-29 | 2003-08-27 | Dioksan-2-alkilkarbamatni derivati, njihova priprava in njihova terapevtska uporaba |
UAA200501766A UA82847C2 (en) | 2002-08-29 | 2003-08-27 | Derivatives of dioxane-2-alkyl carbamates, method for the preparation thereof and application of same in therapeutics |
BR0313846-1A BR0313846A (pt) | 2002-08-29 | 2003-08-27 | Derivados de dioxano-2-alquilcarbamatos, sua preparação e sua aplicação em terapêutica |
EP03758282A EP1537096B1 (fr) | 2002-08-29 | 2003-08-27 | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
DE60323754T DE60323754D1 (de) | 2002-08-29 | 2003-08-27 | Dioxan-2-alkylkarbamaten derivaten, deren herstellung und deren therapeutischen verwendung |
DK03758282T DK1537096T3 (da) | 2002-08-29 | 2003-08-27 | Derivater af dioxan-2-alkylcarbamater, fremstilling og terapeutisk anvendelse heraf |
KR1020107028059A KR101139160B1 (ko) | 2002-08-29 | 2003-08-27 | 디옥산-2-알킬 카르바메이트의 유도체, 그의 제조 방법 및 치료법에서의 그의 적용 |
NZ538404A NZ538404A (en) | 2002-08-29 | 2003-08-27 | Derivatives of dioxane-2-alkyl carbamates, preparation method thereof and application of same in therapeutics |
MEP-2008-242A ME00108B (fr) | 2002-08-29 | 2004-03-11 | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
IL166882A IL166882A (en) | 2002-08-29 | 2005-02-14 | Derivatives of dioxane-2-alkyl carbamates, preparation method thereof and application of same in therapeutics |
IS7699A IS2733B (is) | 2002-08-29 | 2005-02-17 | Afleiður af díoxan-2-alkýlkarbamötum, framleiðsluaðferð þeirra, milliefni notuð við framleiðsluna, og notkun þeirra í meðferð. |
US11/062,541 US7119116B2 (en) | 2002-08-29 | 2005-02-22 | Derivatives of dioxane-2-alkyl carbamates, preparation thereof and application thereof in therapeutics |
NO20051051A NO331165B1 (no) | 2002-08-29 | 2005-02-25 | Derivater av dioksan-2-alkylkarbamater, fremgangsmate for fremstilling derav og anvendelse av de samme for fremstilling av medikamenter |
TNP2005000057A TNSN05057A1 (fr) | 2002-08-29 | 2005-02-25 | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
HRP20050190AA HRP20050190B1 (hr) | 2002-08-29 | 2005-02-28 | Derivati dioksan-2-alkil karbamata, metoda njihove pripreme i primjena istih u terapeutske svrhe |
HK05108400A HK1074445A1 (en) | 2002-08-29 | 2005-09-23 | Derivatives of dioxane-2-alkyl carbamates, preparation method thereof and application of same in therapeutics |
US11/426,964 US20060247290A1 (en) | 2002-08-29 | 2006-06-28 | Derivatives of dioxan-2-alkyl carbamates, preparation thereof and application thereof in therapeutics |
HRP20090270AA HRP20090270B1 (hr) | 2002-08-29 | 2009-05-14 | Derivati dioksan-2-alkil karbamata, metoda njihove pripreme i primjena istih u terapeutske svrhe |
US12/510,326 US7777057B2 (en) | 2002-08-29 | 2009-07-28 | Derivatives of dioxan-2-alkyl carbamates, preparation thereof and application thereof in therapeutics |
IL201472A IL201472A (en) | 2003-08-27 | 2009-10-12 | Intermediates for the preparation of dioxane-2-alkyl carbamates |
US12/834,268 US8119687B2 (en) | 2002-08-29 | 2010-07-12 | Derivatives of dioxan-2-alkyl carbamates, preparation thereof and application thereof in therapeutics |
NO20110598A NO335866B1 (no) | 2002-08-29 | 2011-04-15 | Karbonatforbindelse |
Applications Claiming Priority (2)
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FR0210707A FR2843964B1 (fr) | 2002-08-29 | 2002-08-29 | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
FR02/10707 | 2002-08-29 |
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WO2004020430A3 WO2004020430A3 (fr) | 2004-04-22 |
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PCT/FR2003/002590 WO2004020430A2 (fr) | 2002-08-29 | 2003-08-27 | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
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US (4) | US7119116B2 (fr) |
EP (2) | EP1537096B1 (fr) |
JP (2) | JP4585854B2 (fr) |
KR (2) | KR101139160B1 (fr) |
CN (3) | CN101906071A (fr) |
AR (1) | AR041053A1 (fr) |
AT (2) | ATE409184T1 (fr) |
AU (1) | AU2003274292B2 (fr) |
BR (1) | BR0313846A (fr) |
CA (2) | CA2496040C (fr) |
CO (1) | CO5700820A2 (fr) |
CY (2) | CY1108792T1 (fr) |
DE (2) | DE60328138D1 (fr) |
DK (2) | DK1537096T3 (fr) |
EA (1) | EA008218B1 (fr) |
ES (2) | ES2312808T3 (fr) |
FR (1) | FR2843964B1 (fr) |
HK (2) | HK1108157A1 (fr) |
HR (2) | HRP20050190B1 (fr) |
IL (1) | IL166882A (fr) |
IS (1) | IS2733B (fr) |
MA (1) | MA27390A1 (fr) |
ME (2) | MEP24208A (fr) |
MX (1) | MXPA05002319A (fr) |
NO (2) | NO331165B1 (fr) |
NZ (1) | NZ538404A (fr) |
PL (1) | PL209339B1 (fr) |
PT (2) | PT1537096E (fr) |
RS (2) | RS20100169A (fr) |
SI (2) | SI1840125T1 (fr) |
TN (1) | TNSN05057A1 (fr) |
TW (2) | TWI294878B (fr) |
UA (1) | UA82847C2 (fr) |
WO (1) | WO2004020430A2 (fr) |
ZA (1) | ZA200501537B (fr) |
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US5173506A (en) * | 1990-08-16 | 1992-12-22 | Schering Corporation | N-(mercaptoalkyl)ureas and carbamates |
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CA2290695A1 (fr) * | 1997-06-05 | 1998-12-10 | Patrick Lardenois | Derives de 5-naphtalen-1-yl-1,3-dioxane, leur preparation et leur application en therapeutique |
CA2328234C (fr) * | 1998-04-16 | 2009-03-17 | Texas Biotechnology Corporation | Composes inhibant la fixation d'integrines a leurs recepteurs |
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FR2843964B1 (fr) * | 2002-08-29 | 2004-10-01 | Sanofi Synthelabo | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
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2002
- 2002-08-29 FR FR0210707A patent/FR2843964B1/fr not_active Expired - Fee Related
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2003
- 2003-08-26 AR ARP030103063A patent/AR041053A1/es active IP Right Grant
- 2003-08-27 RS RSP-2010/0169A patent/RS20100169A/en unknown
- 2003-08-27 NZ NZ538404A patent/NZ538404A/en not_active IP Right Cessation
- 2003-08-27 EP EP03758282A patent/EP1537096B1/fr not_active Expired - Lifetime
- 2003-08-27 KR KR1020107028059A patent/KR101139160B1/ko not_active IP Right Cessation
- 2003-08-27 WO PCT/FR2003/002590 patent/WO2004020430A2/fr active Application Filing
- 2003-08-27 CA CA2496040A patent/CA2496040C/fr not_active Expired - Fee Related
- 2003-08-27 DE DE60328138T patent/DE60328138D1/de not_active Expired - Lifetime
- 2003-08-27 BR BR0313846-1A patent/BR0313846A/pt not_active Application Discontinuation
- 2003-08-27 EA EA200500268A patent/EA008218B1/ru not_active IP Right Cessation
- 2003-08-27 PT PT03758282T patent/PT1537096E/pt unknown
- 2003-08-27 AU AU2003274292A patent/AU2003274292B2/en not_active Ceased
- 2003-08-27 CA CA2700319A patent/CA2700319C/fr not_active Expired - Fee Related
- 2003-08-27 ES ES03758282T patent/ES2312808T3/es not_active Expired - Lifetime
- 2003-08-27 SI SI200331666T patent/SI1840125T1/sl unknown
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JP2006525293A (ja) * | 2003-05-07 | 2006-11-09 | サノフィ−アベンティス | ピペリジニル−およびピペラジニル−アルキルカルバメート誘導体、その製造法および治療用途 |
US7645757B2 (en) | 2004-02-26 | 2010-01-12 | Sanofi-Aventis | Derivatives of heteroaryl-alkylcarbamates, methods for their preparation and use thereof as fatty acid amido hydrolase enzyme inhibitors |
WO2005090347A1 (fr) * | 2004-02-26 | 2005-09-29 | Sanofi-Aventis | Derives d’aryl- et d’heteroaryl-piperidinecarboxylates, leur preparation et leur application comme inhibiteurs de l'enzyme faah |
EP2251324A1 (fr) | 2004-02-26 | 2010-11-17 | Sanofi-Aventis | Dérivés d'heteroaryl-alkylcarbamates, leur preparation et leur application comme inhibiteurs de l'enzyme faah |
US7781590B2 (en) | 2004-02-26 | 2010-08-24 | Sanofi-Aventis | Piperidinylalkylcarbamate derivatives, methods for their preparation and the therapeutic use thereof as fatty acid amido hydrolase enzyme inhibitors |
WO2005090292A1 (fr) * | 2004-02-26 | 2005-09-29 | Sanofi-Aventis | Derives d’heteroaryl-alkylcarbamates, leur preparation et leur application comme inhibiteurs de l’enzyme faah |
FR2866886A1 (fr) * | 2004-02-26 | 2005-09-02 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-akylcarbamates, leur preparation et leur application en therapeutique |
FR2866884A1 (fr) * | 2004-02-26 | 2005-09-02 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-piperidinecarboxylates, leur preparation et leur application en therapeutique |
FR2866885A1 (fr) * | 2004-02-26 | 2005-09-02 | Sanofi Synthelabo | Derives de piperidinylalkylcarbamates, leur prepation et leur application en therapeutique |
WO2005089759A1 (fr) * | 2004-02-26 | 2005-09-29 | Sanofi-Aventis | Derives de piperidinylalkylcarbamates, leur preparation et leur application comme inhibiteurs de l’enzyme faah |
DE102004039326A1 (de) * | 2004-08-12 | 2006-02-16 | Abbott Gmbh & Co. Kg | Neue medizinische Verwendungen und Verfahren |
US7915261B2 (en) | 2005-02-17 | 2011-03-29 | Astellas Pharma, Inc. | Pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound |
US7919494B2 (en) | 2005-02-17 | 2011-04-05 | Astellas Pharma, Inc. | Pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound |
US7919495B2 (en) | 2005-02-17 | 2011-04-05 | Astellas Pharma, Inc. | Pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound |
JP4857332B2 (ja) * | 2005-05-03 | 2012-01-18 | サノフイ | アルキル、アルケニルおよびアルキニルカルバメート誘導体、この製剤および治療上の使用 |
US8207226B1 (en) | 2008-06-03 | 2012-06-26 | Alcon Research, Ltd. | Use of FAAH antagonists for treating dry eye and ocular pain |
WO2011030798A1 (fr) | 2009-09-09 | 2011-03-17 | 大日本住友製薬株式会社 | Dérivés de 8-oxodihydropurine |
EP2545915A1 (fr) | 2011-07-11 | 2013-01-16 | Sanofi | 2-amino-2-oxoéthyle trans-3-[5-(6-méthoxy-naphtalène-1-yl)-1,3-dioxan-2-yl]propyl-carbamate pour l'utilisation dans le traitement de la douleur persistante du cancer |
EP2545914A1 (fr) | 2011-07-11 | 2013-01-16 | Sanofi | 2-amino-2-oxoéthyle trans-3-[5-(6-méthoxy-naphtalène-1-yl)-1,3-dioxan-2-yl]propyl-carbamate pour l' utilisation dans le traitement de la douleur persistante du cancer |
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