Reference

Piperidine derivatives having gastrointestinal activity

Piperidine derivatives having gastrointestinal activity. Stemp, Jean Anne; Miller, David; Martin, Roger Thomas (Beecham Group PLC, UK). Eur. Pat. Appl. EP 190496 A2 13 Aug 1986, 92 pp. DESIGNATED STATES: R: BE, CH, DE, FR, GB, IT, LI, LU, NL, SE. (European Patent Organization) CODEN: EPXXDW. CLASS: ICM: C07D211-22. 105813-26-1 and 105812-81-5 which are cas registry numbers are also used here. ICS: C07D405-12. APPLICATION: EP 85-308936 9 Dec 1985. PRIORITY: GB 84-31478 13 Dec 1984; GB 85-20619 16 Aug 1985. DOCUMENT TYPE: Patent CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Section cross-reference(s): 1 Title compds. I [R1, R2 = H, R1R2 = bond; R3, R4 = (un)substituted Ph, naphthyl; R5 = (CH2)nR6; R6 = (un)substituted Ph or naphthyl; n = 1, 2] and their salts, useful as antiulcer agents and for treatment of impaired gastrointestinal motility, were prepd. Thus, (-)-trans-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperi dine in DMF was reacted with PhCH2Cl to give (-)-trans-1-benzyl-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymeth yl)piperidine (II). In antiulcer tests on rats, II at 10.5 mg/kg orally showed 53% inhibition of gastric erosions. .

Process for the preparation of (-)-trans-4-(p-fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]pipe ridine

All Rights Reserved. Process for the preparation of (-)-trans-4-(p-fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]pipe ridine. Mistry, Ankur Bhupendrakumar; Pillai, Mandakini Mutthukumaran; Patel, Vijaykumar Muljibhai; Chitturi, Trinadha Rao; Thennati, Rajamannar (Sun Pharmaceutical Industries Limited, India). PCT Int. Appl. WO 2007015262 A2 8 Feb 2007, 24pp. DESIGNATED STATES: 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, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, 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; RW: AT, BE, BF, BJ, CF, CG, CH, CI, CM, CY, DE, DK, ES, FI, FR, GA, GB, GR, IE, IS, IT, LU, MC, ML, MR, NE, NL, PT, SE, SN, TD, TG, TR. 67-68-5 and 105812-81-5 are cas registry numbers. These chemicals are also mentioned in this article. (English). (World Intellectual Property Organization). CODEN: PIXXD2. APPLICATION: WO 2006-IN138 24 Apr 2006. PRIORITY: IN 2005-MU506 25 Apr 2005. DOCUMENT TYPE: Patent CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Process for producing compd. I or pharmaceutically acceptable salts thereof, comprising hydrolysis of a compd. II [R = halo, (un)substituted linear, branched or cyclic alkyl, aryl, etc.] by treatment with a base in a solvent system comprising a polar aprotic water miscible solvent and a hydrocarbon solvent wherein the polar aprotic water miscible solvent is selected from a sulfoxide solvent, an amide solvent or mixt. thereof, was provided. For example, a mixt. of (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidin e-1-carboxylic acid Ph ester (50 g) and KOH (30 g) in toluene (250 mL) and dimethylsulfoxide (50 mL) was stirred at 80-85° for 4 h. Aq. work-up followed by treatment with HCl afforded compd. I×HCl in 92.1% yield. Of note, the present invention employs a polar aprotic water miscible solvent/hydrocarbon solvent system, e.g, toluene-dimethylsulfoxide, etc., instead of the prior art usage of alc. solvent. .