Title:
ARYL ALKYL CARBAMATE DERIVATIVES PRODUCTION AND USE THEREOF IN THERAPY
Document Type and Number:
WIPO Patent Application WO2004067498
Kind Code:
A3
Abstract:
2-Amino-2-oxoethyl phenylalkylcarbamate derivatives (I) are new. Also new are certain alkyl ester and oxazolidine-dione derivative intermediates. Carbamates of formula (I) and their acid addition salts, hydrates and solvates are new. n = 1-6; A = one or more groups X, Y and/or Z; X = 1-2C alkylene (optionally substituted (os) by one or more of 1-12C alkyl, cycloalkyl or cycloalkyl-(1-6C) alkyl; Y = 1-2C alkenylene (os by one or more of 1-12C alkyl, cycloalkyl or cycloalkyl-(1-6C) alkyl; Z = 3-7C cycloalkylidene or 3-7C cycloalkylene; R1 = H, halo, OH, CN, NO2, alkyl, alkoxy, alkylthio, fluoroalkyl, fluoroalkoxy or fluoroalkylthio; R2 = as R1; or phenyl, naphthyl, biphenylyl, phenylethenyl, naphthylethenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, indanyl, indenyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalzinyl, cinnolinyl, thienyl, furanyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, triazolyl, benzothienyl, benzofuranyl, dibenzofuranyl, benzimidazolyl, benzotriazolyl, indolyl, isoindolyl, indazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, dihydroindolyl, pyrrolopyridinyl, thienopyridinyl, furopyridinyl, imidazopyridinyl, oxazolopyridinyl, thiazolopyridinyl, pyrazolopyridinyl, isoxazolopyridinyl, isothiazolopyridinyl, tetrahydroquinolinyl, isotetrahydroquinolinyl, phenoxy, phenylthio, phenylsulfonyl, benzoyl, phenylmethoxy, phenylethoxy, naphthylmethoxy, naphthylethoxy, naphthylpropoxy, quinolinyloxy or isoquinolinyl (all os by one or more of halo, CN, NO2, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio, fluoroalkyl, fluoroalkoxy, fluoroalkylthio, phenoxy, benzyloxy, piperidinyl, pyrrolidinyl, morpholinyl, NR6R7, NHCOR6, COR6COOR6, SO2R6, 1-3C alkylenedioxy or piperazino (os by alkyl or benzyl); R6, R7 = alkyl or phenyl; R3 = -CHR4-CO-NHR5; R4 = H or alkyl; and R5 = H, alkyl, 3-5C cycloalkyl or cycloalkyl-(1-6C) alkyl; Unless specified otherwise, alkyl moieties have 1-3C and cycloalkyl moieties 3-7C. Independent claims are also included for: (1) Preparation of (I); and (2) New intermediates comprising: (a) ester compounds (I'), of formula as for (I) but having R3 replaced by -CHR4-COOR; (b) trifluoromethanesulfonated ester compounds (I''), of formula as for (I) but having R3 replaced by -CHR4-COOR and R2 replaced by R8; (c) oxazoline-diones of formula (V); and (d) trifluoromethanesulfonated oxazoline-diones (V'), of formula as for (V) but having R3 = -CHR4-COOR and R2 replaced by R8. R = Me or Et; and R8 = triflate.
Inventors:
ABOUABDELLAH AHMED (FR)
ALMARIO GARCIA ANTONIO (FR)
HOORNAERT CHRISTIAN (FR)
RAVET ANTOINE (FR)
ALMARIO GARCIA ANTONIO (FR)
HOORNAERT CHRISTIAN (FR)
RAVET ANTOINE (FR)
Application Number:
PCT/FR2004/000139
Publication Date:
November 04, 2004
Filing Date:
January 22, 2004
Export Citation:
Assignee:
SANOFI AVENTIS (FR)
ABOUABDELLAH AHMED (FR)
ALMARIO GARCIA ANTONIO (FR)
HOORNAERT CHRISTIAN (FR)
RAVET ANTOINE (FR)
ABOUABDELLAH AHMED (FR)
ALMARIO GARCIA ANTONIO (FR)
HOORNAERT CHRISTIAN (FR)
RAVET ANTOINE (FR)
International Classes:
A61K31/27; A61K31/33; A61P1/00; A61P9/00; A61P11/00; A61P13/10; A61P25/00; A61P35/00; A61P37/08; C07C269/00; C07C269/06; C07C271/10; C07C271/12; C07C271/14; C07C271/16; C07C271/18; C07C271/20; C07D213/40; C07D215/12; C07D217/18; C07D241/12; C07D261/08; C07D263/44; C07D285/06; C07D307/91; C07D333/20; C07D333/58; (IPC1-7): C07C271/10; C07C269/06; C07C269/00; C07D263/44; A61K31/27; A61K31/33
Domestic Patent References:
| WO2002087569A1 | 2002-11-07 | |||
| WO2003065989A2 | 2003-08-14 |
Foreign References:
| US6462054B1 | 2002-10-08 |
Other References:
CHEMICAL ABSTRACTS, vol. 73, no. 3, 20 July 1970, Columbus, Ohio, US; abstract no. 14748u, DOVLATYAN, V. V. ET AL.: "Synthesis of pesticides." page 358; column 1; XP002257138
GIORGIO TARZIA ET AL.: "Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of Fatty Acid Amide Hydrolase inhibitors", JOURNAL OF MEDICINAL CHEMISTRY., vol. 46, no. 12, 2003, AMERICAN CHEMICAL SOCIETY. WASHINGTON., US, pages 2352 - 2360, XP002257137, ISSN: 0022-2623
GIORGIO TARZIA ET AL.: "Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of Fatty Acid Amide Hydrolase inhibitors", JOURNAL OF MEDICINAL CHEMISTRY., vol. 46, no. 12, 2003, AMERICAN CHEMICAL SOCIETY. WASHINGTON., US, pages 2352 - 2360, XP002257137, ISSN: 0022-2623
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