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CAS indexed 396 chemical substances from this document.
CAS subject entries for this document include: Chemokine receptors; Anti-AIDS agents; Human; and 2 additional concepts. | |
CAPLUS COPYRIGHT 2003 ACS on STN
| TITLE:
| Preparation of tertiary N-(5,6,7,8-tetrahydro-8-quinolinyl)-N-(1H-benzimidazol-2-ylmethyl)amines and analogs as chemokine receptor modulators for treatment of HIV or FIV |
| INVENTOR(S):
| Bridger, Gary; Skerlj, Renato; Kaller, Al; Harwig, Curtis; Bogucki, David; Wilson, Trevor R.; Crawford, Jason; Mceachern, Ernest J.; Atsman, Berm; Nan, Siqiao; Zhou, Yuanxi; Schols, Dominique; Smith, Christopher Dennis; Di Fluri, Rosaria Maria |
| PATENT ASSIGNEE(S):
| Anormed Inc., Can. |
| SOURCE:
| PCT Int. Appl., 187 pp. CODEN: PIXXD2 |
| LANGUAGE:
| English |
PATENT INFORMATION: PATENT NO. KIND DATE APPLICATION NO. DATE
--------------- ---- -------- --------------- --------
WO 2002034745 A1 20020502 WO 2001-US29590 20010919
WO 2002034745 C1 20030918
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN,
CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH,
GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR,
LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, PH, PL,
PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, TZ, UA, UG,
US, UZ, VN, YU, ZA, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM
RW: GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZW, AT, BE, CH, CY,
DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF,
BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG
EP 1317451 A1 20030611 EP 2001-975290 20010917
R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT,
IE, SI, LT, LV, FI, RO, MK, CY, AL, TR
BR 2001013932 A 20030624 BR 2001-13932 20010917
AU 2001094628 A5 20020506 AU 2001-94628 20010919
US 2003028022 A1 20030206 US 2002-31812 20020328
NO 2003001161 A 20030313 NO 2003-1161 20030313
ABSTRACT:
Title compds. I [wherein ring A optionally comprises a heteroatom selected from N, O, or S; R1-R3 = non-interfering substituents; R4 and R5 = independently H or (un)substituted alkyl, alkenyl, alkynyl, or acyl; or 2 R5 may form a cyclic amine, optionally contg. 1 or more N, O, and/or S; R = independently H or alkyl; X = O or S or (un)substituted C or N; Y = independently halo, OH, SH, SO, SO2, non-N contg. org. moiety, (CH2)xCN, (CR2)xNR52, (CR2)xNR(CR2)xNRR4, (CR2)xNR(CR2)xNR(CR2)xNR52, (CR2)xCO(CR2)xNR52, (CR2)xCO(CR2)xNR(CR2)xNRR4, (CR2)xCO(CR2)xNR(CR2)xNR(CR2)xNR52, (CR2)xNRCO(CR2)xNRR4, (CR2)xNRCO(CR2)xNR(CR2)xNR52, (CR2)xNRCO(CR2)xNR(CR2)xNR(CR2)xNR(CR2)xNR52, CH:NZ, (CR2)xZ, NR(CR2)xZ, (CR2)xNROH, (CR2)xCONROH, or (CR2)xCR:NOH; or 2 Y groups may be connected to form a fused ring with Ar; Z = (un)substituted (hetero)aryl; Ar = (hetero)aryl; m = 0-2; n = 0-2; p = 0-4; q = 0-3; x = 0-4; with provisos; and pharmaceutically acceptable salts and pro-drugs thereof] were prepd. as modulators of chemokine receptor activities. For example, reductive addn. of 3-cyanobenzaldehyde to 8-amino-5,6,7,8-tetrahydroquinoline using sodium triacetoxyborohydride in CH2Cl2 afforded N-(5,6,7,8-tetrahydro-8-quinolinyl)-3-cyanobenzylamine (81%). Alkylation with N-(tert-butoxycarbonyl)-2-chloromethylbenzimidazole using N,N-diisopropylethylamine and KI in MeCN (88%), followed by hydrogenation in the presence of Raney nickel (79%), gave the tertiary amine II (AMD9679). Compds. of the invention tested for inhibition of HIV-1 NL4.3 or IIIB replication in MT-4 cells exhibited EC50 values of 0.002 .mu.M/mL to 20.0 .mu.M/mL. Thus, I are useful for the treatment of human immunodeficiency virus (HIV) and/or feline immunodeficiency virus (FIV).
Updated 5/9/2007 12:54:01 PM
