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CAPLUS COPYRIGHT 2007 ACS on STN
| TITLE:
| Preparation of heterocycle-containing alkynyl derivatives as modulators of metabotropic glutamate receptors |
| INVENTOR(S):
| Bessis, Anne-Sophie; Bolea, Christelle; Bonnet, Beatrice; Epping-Jordan, Mark; Poirier, Nicholas; Poli, Sonia-Maria; Rocher, Jean-Philippe; Thollon, Yves |
| PATENT ASSIGNEE(S):
| Addex Pharmaceuticals SA, Switz. |
| SOURCE:
| PCT Int. Appl., 308 pp. CODEN: PIXXD2 |
| LANGUAGE:
| English |
PATENT INFORMATION: PATENT NO. KIND DATE APPLICATION NO. DATE
--------------- ---- -------- -------------------- --------
WO 2005123703 A2 20051229 WO 2005-IB2390 20050617
WO 2005123703 A3 20061012
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH,
CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD,
GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ,
LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA,
NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK,
SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU,
ZA, ZM, ZW
RW: BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM,
AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK,
EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, MC, NL, PL, PT,
RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML,
MR, NE, SN, TD, TG
AU 2005254808 A1 20051229 AU 2005-254808 20050617
CA 2570987 A1 20051229 CA 2005-2570987 20050617
EP 1765795 A2 20070328 EP 2005-766895 20050617
R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE,
IS, IT, LI, LT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR, AL, BA,
HR, LV, MK, YU
CN 101001846 A 20070718 CN 2005-80026025 20050617
IN 2006CN04639 A 20070629 IN 2006-CN4639 20061218
NO 2007000288 A 20070116 NO 2007-288 20070116
ABSTRACT:
The present invention relates to heterocycle-contg. alkynyl derivs. (WC.tplbond.C(CH2)nXW' (I); variables defined below; e.g. 1-methyl-2-[4-(pyridin-2-yl)-3-butynyl]-1H-benzo[d]imidazole (shown as II)) that are modulators of metabotropic glutamate receptors - subtype 5 ("mGluR5") and are therefore useful for the treatment of central nervous system disorders as well as other disorders modulated by mGluR5 receptors. Methods of prepn. are claimed and prepns. and/or characterization data for .apprx.250 examples of I are included. For example, II was prepd. in 4 steps (not stated, 23, 70 and 31 % yields, resp.) starting with chlorination of (1-methyl-1H-benzimidazol-2-yl)methanol to give 2-chloromethyl-1-methyl-1H-benzimidazole, which was coupled with trimethylprop-1-ynylsilane to give 1-methyl-2-[4-(trimethylsilanyl)-3-butynyl]-1H-benzimidazole, which was deprotected to give 2-(3-butynyl)-1-methyl-1H-benzimidazole, which was coupled with 2-iodopyridine to give II. For I: W is a 5-, 6-heterocyclic ring contg. a N adjacent to the ethynyl bond, which ring may optionally be fused with a 5- or 6-membered ring contg. .gtoreq.1 atoms independently C, N, O and S; X = an (un)substituted C1-C6-alkyl, C1-C6-alkylhalo, C2-C6-alkynyl, C2-C6-alkenyl, O-C0-C6-alkyl, O-C1-C6-alkylhalo, O-C3-C6-alkynyl, O-C3-C6-alkenyl, O-C3-C7-cycloalkyl, C1-C6-alkyl-O, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C0-C6-alkyl, et al.; W' = a 5- or 6-membered ring contg. .gtoreq.1 atoms = C, N, O and S, which ring may optionally be fused with a 5- or 6-membered ring contg. .gtoreq.1 atoms = C, N, O and S; addnl. details including provisos are given in the claims. Results of a mGluR5 binding assay for >200 examples of I are tabulated; also test results of a marble burying model of anxiety in mice and Vogel conflict drinking model of anxiety in rats are discussed.
Updated 8/24/2007 12:51:55 PM
