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1. (WO2009141533) PYRROLE DERIVATIVES, PREPARATION OF SAME AND THERAPEUTIC APPLICATION THEREOF AS CANNABINOID CB1 RECEPTOR ANTAGONISTS
Latest bibliographic data on file with the International Bureau   

Pub. No.:    WO/2009/141533    International Application No.:    PCT/FR2009/000536
Publication Date: 26.11.2009 International Filing Date: 07.05.2009
IPC:
C07D 401/12 (2006.01), C07D 401/14 (2006.01), A61K 31/4025 (2006.01), A61P 25/00 (2006.01), A61P 29/00 (2006.01), A61P 3/00 (2006.01), A61P 1/00 (2006.01)
Applicants: SANOFI-AVENTIS [FR/FR]; 174, avenue de France F-75013 Paris (FR) (For All Designated States Except US).
BARTH, Francis [FR/FR]; (FR) (For US Only).
CONGY, Christian [FR/FR]; (FR) (For US Only).
JEANJEAN, Audrey [FR/FR]; (FR) (For US Only).
RINALDI-CARMONA, Murielle [FR/FR]; (FR) (For US Only)
Inventors: BARTH, Francis; (FR).
CONGY, Christian; (FR).
JEANJEAN, Audrey; (FR).
RINALDI-CARMONA, Murielle; (FR)
Agent: KUGEL, Dominique; Sanofi-Aventis Département Brevets 174, avenue de France F-75013 Paris (FR)
Priority Data:
08/02553 09.05.2008 FR
Title (EN) PYRROLE DERIVATIVES, PREPARATION OF SAME AND THERAPEUTIC APPLICATION THEREOF AS CANNABINOID CB1 RECEPTOR ANTAGONISTS
(FR) DERIVES DE 4,5-DIPHENYLEPYRROLE-2-YLCARBOXAMIDE, LEUR PREPARATION ET LEUR UTILISATION COMME ANTAGONISTES DES RECEPTEURS CB1 DES CANNABINOIDES
Abstract: front page image
(EN)The subject of the invention is compounds corresponding to the formula (I): in which: - R1 represents a hydrogen atom or a (C1-C4)alkyl group; - R2 represents a homopiperidin-1-yl, piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl radical, or an amino (C1-C6)alkyl group; - or R1 and R2, together with the nitrogen atom to which they are attached, constitute a piperazin-1-yl, 1,4-diazepan-1-yl, homopiperidin-1-yl, piperidin-1-yl, pyrrolidin-1-yl or azetidin-1-yl radical; - one of the two substituents R3, R6 represents a Y-A-R9 group; - Y represents an oxygen atom, or an -S(O)n-, -OSO2- or-N(R18)- group; ‑ A represents an unsubstituted (C1-C4)alkylene group; - R9 represents an -OR12, -CN, ‑CO2H, NR12R13, -CONR12R13, -NR15COR12,-CONHNH2, -CONHOH, -CONHSO2R14, ‑S(O)nR14, -SO2NR12R13, -NR18SO2R14, or-NR15SO2NR12R13 group, or an aromatic heterocycle. The present invention also relates to the methods of preparation and the therapeutic applications of the compounds of formula (I) as cannabinoid CB1 receptor antagonists.
(FR)L'invention a pour objet des composés répondant à la formule (I) dans laquelle : R1 représente un atome d'hydrogène ou un groupe (C1-C4)alkyle; R2 représente un radical homopipéridin-1-yle, pipéridin-1-yle, pyrrolidin-1-yle, azétidin-1-yle, ou un groupe amino (C1-C6)alkyle; ou R1 et R2 ensemble avec l'atome d'azote auquel ils sont liés constituent un radical pipérazin-1-yle ou 1,4-diazépan-1-yle, homopipéridin-1-yle, pipéridin-1-yle, pyrrolidin-1-yle ou azétidin-1-yle; un des deux substituants R3, R6 représente un groupe Y-A-R9; Y représente un atome d'oxygène, un groupe -S(O)n-, -OSO2- ou -N(R18)-; A représente un groupe alkylène en (C1-C4) non substitué; R9 représente un groupe -OR12, -CN, -CO2H, NR12R13, -CONR12R13, -NR15COR12, -CONHNH2, -CONHOH, -CONHSO2R14, -S(O)nR14, -SO2NR12R13, -NR18SO2R14, -NR15SO2NR12R13, ou un hétérocycle aromatique. La présente invention concerne également les procédés de préparation et les applications thérapeutiques des composés de formule (I) en tant qu'antagonistes des récepteurs CB1 des cannabinoïdes.
Designated States: AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW.
African Regional Intellectual Property Organization (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG).
Publication Language: French (FR)
Filing Language: French (FR)