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Wo 2010/148314 A2 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date 23 December 2010 (23.12.2010) WO 2010/148314 A2 (51) International Patent Classification: Vijaya Bhaskar [IN/IN]; Flat No. 209, S. V. Sumithra C07D 401/12 (2006.01) A61P 1/04 (2006.01) Apartments, Sumithra Nagar, Kukatpally, Hyderabad, 500 A61K 31/4439 (2006.01) 072, Andhra Pradesh (IN). (21) International Application Number: (74) Agent: FRANKS, Robert A.; Dr. Reddy's Laboratories, PCT/US2010/039187 Inc., 200 Somerset Corporate Boulevard 7th Floor, Bridgewater, New Jersey 08807 (US). (22) International Filing Date: 18 June 2010 (18.06.2010) (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (25) Filing Language: English AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (26) Publication Language: English CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (30) Priority Data: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 1452/CHE/2009 19 June 2009 (19.06 .2009) IN KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, 61/292,6 17 6 January 2010 (06.01 .2010) US ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, 573/CHE/2010 5 March 2010 (05.03 .2010) IN NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (71) Applicants (for all designated States except US): DR. SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, REDDY S LABORATORIES LTD. [IN/IN]; 7-1-27 TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. Ameerpet, Hyderabad, 500 016, Andhra Pradesh (IN). (84) Designated States (unless otherwise indicated, for every DR. REDDY S LABORATORIES, INC. [US/US]; 200 kind of regional protection available): ARIPO (BW, GH, Somerset Corporate Boulevard 7th Floor, Bridgewater, GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, New Jersey 08807 (US). ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, (72) Inventors; and TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (75) Inventors/Applicants (for US only): BHIMAVARAPU, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, Srinivasa Reddy [IN/IN]; H. No. 16/9 A. B/h New Bus LV, MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, Stop, Kollipara (Mandal), Guntur (District), 522 304, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Andhra Pradesh (IN). VAKAMUDI, Sree Naga Venkata GW, ML, MR, NE, SN, TD, TG). Lakshmi Vara Prasad [IN/IN]; H. No. 13-33, Pathapeta, Published: Nuzvid, Krishna (District), 521 201, Andhra Pradesh — to (IN). ELATI, Ravi Ram Chandra Sekhar [IN/IN]; H. without international search report and be republished upon receipt of that report (Rule 48.2(g)) No. 515, Near Ramalayam, HMT Hills, KPHB, Hyder abad, 500 072, Andhra Pradesh (IN). BOLUGODDU, (54) Title: PREPARATION OF ESOMEPRAZOLE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS (57) Abstract: Processes for the preparation of esomeprazole and its pharmaceutically acceptable salts. PREPARATION OF ESOMEPRAZOLE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS INTRODUCTION The present application relates to processes for the preparation of esomeprazole and its pharmaceutically acceptable salts. The drug compound having the adopted name "esomeprazole magnesium," in its anhydrous form, has a chemical name bis(5-methoxy-2-[(S)- [(4-methoxy-3,5-dimethyl-2-pyhdinyl)methyl]sulfinyl]-1 /-/-benzimidazole-1 -yl) magnesium, and has the structure of formula (Ia). 2 (Ia) Esomeprazole magnesium is a proton pump inhibitor, developed as an oral treatment for peptic ulcer, gastroesophangeal reflux disease (GERD), duodenal ulcer, and esophagitis. Esomeprazole magnesium thhydrate is the active ingredient in products sold by AstraZeneca Pharmaceuticals as NEXIUM™, in the form of delayed- release capsules for oral administration. Each delayed-release capsule contains 20 mg or 40 mg of esomeprazole (present as 22.3 mg or 44.5 mg of esomeprazole magnesium trihydrate) in enteric-coated pellets. U.S. Patent No. 5,948,789 discloses a process for enantioselective synthesis of 2-(2-pyridinylmethylsulphinyl)-1 H-benzimidazoles or an alkaline salt thereof, in the form of a single enantiomer or in an enantiomerically enriched form, by oxidizing a pro-chiral sulfide with an oxidizing agent in the presence of a chiral titanium complex and a base in an organic solvent. International Application Publication No. WO 2005/054228 A 1 discloses a process for making 2-(2-pyhdinylmethylsulphinyl)-1 H-benzimidazoles, either as a single enantiomer or in an enantiomerically enriched form by asymmetric oxidation of the corresponding prochiral 4-chloro or 4-nitro analog of 2-(2-pyridinylmethyl- sulphanyl)-1 H-benzimidazole with an oxidizing agent and a chiral titanium complex in an organic solvent, followed by reaction of the 4-chloro or 4-nitro analog of 2-(2-pyridinylmethylsulphanyl)-1 H-benzimidazole with an alkali metal or alkaline earth metal alkoxide. International Application Publication No. WO 2005/080374 A 1 discloses a process for preparation of 2-[[(4-X-3,5-dimethylpyridin-2-yl)methyl]thio]-5- methoxy-1 H-benzimidazole or 2-[[(4-X-3,5-dimethyl-1 -oxidopyridin-2- yl)methyl]thio]-5-methoxy-1 H-benzimidazole, either as a single enantiomer or in an enantiomehcally enriched form, wherein X is a leaving group such as a + halogen (F, Cl, Br, or I), NO2, N2 , or OSO2R (where R is CH3, CF3, p-toluene, m- chlorobenzene, or p-chlorobenzene), by asymmetric oxidation of the corresponding prochiral sulfide with an oxidizing agent and a chiral titanium complex in an organic solvent. The obtained 2-[[(4-X-3,5-dimethylpyridin-2- yl)methyl]thio]-5-methoxy-1 H-benzimidazole or 2-[[(4-X-3,5-dimethyl-1 - oxidopyridin-2-yl)methyl]thio]-5-methoxy-1 H-benzimidazole, either as a single enantiomer or in an enantiomerically enriched form, is further converted to esomeprazole. These processes suffer from one or more drawbacks such as low enantiomeric purity, low yield, and high levels of sulfide and sulfone impurities. Hence, there is a need to provide simple, economical and robust processes for the preparation of esomeprazole and its pharmaceutically acceptable salts. SUMMARY In an aspect, the present invention relates to processes for the preparation of esomeprazole of formula I, or pharmaceutically acceptable salts thereof, embodiments including one or more of the following steps: (a) reacting the pro-chiral sulfide of formula (II), (H) with an oxidizing agent, in the presence of a chiral auxiliary, to provide a compound of formula (III) or a salt thereof, in the form of a single enantiomer or in an enantiomerically enriched form; (b) converting a compound of formula (III) or a salt thereof, in the form of a single enantiomer or in an enantiomerically enriched form, to esomeprazole free base of formula (I), (I) or a pharmaceutically acceptable salt thereof; and (c) optionally, when a salt is formed in (b), converting the salt of esomeprazole into a second salt of esomeprazole. The present invention also includes a piperidine salt of 5-methoxy-2-[(S)- [(4-nitro-3,5-dimethylpyridin-2-yl)methyl] sulfinyl]-1 H-benzimidazole having formula (IV). BRIEF DESCRIPTION O F THE DRAWING Fig. 1 is an illustration of an X-ray powder diffraction (PXRD) pattern for a piperidine salt of 5-methoxy-2-[(S)-[(4-nitro-3,5-dimethylpyridin-2- yl)methyl]sulfinyl]-1 H-benzimidazole. DETAILED DESCRIPTION Percentages herein are expressed on a weight basis, unless the context indicates otherwise. In an aspect, the present invention relates to processes for the preparation of esomeprazole of formula (I), or a pharmaceutically acceptable salt thereof, embodiments including one or more of the following steps: (a) reacting the pro-chiral sulfide of formula (II), (H) with an oxidizing agent, in the presence of a chiral auxiliary, to provide a compound of formula (III) or a salt thereof, in the form of a single enantiomer or in an enantiomerically enriched form; (ill) (b) converting a compound of formula (III) or a salt thereof, in the form of a single enantiomer or in an enantiomerically enriched form, to esomeprazole free base of formula (I), (I) or a pharmaceutically acceptable salt thereof; and (c) optionally, when a salt is formed in (b), converting the salt of esomeprazole into a second salt of esomeprazole. Step (a) involves reacting the pro-chiral sulfide of formula (II) with an oxidizing agent. The pro-chiral sulphide compound can have a significant moisture content, as synthesized or received from a supplier. For example, the pro-chiral sulphide compound can be a hydrate, having an amount of water that can be about 5% by weight, or higher. In embodiments, the pro-chiral sulphide of formula (II) can first be subjected to a water removal procedure, using methods such as azeotropic distillation, fractional distillation, or any other techniques, to reduce its water content before reacting with an oxidizing agent. For example, the pro-chiral sulphide of formula (II) may be combined with an organic solvent, such as, but not limited to, a solvent that forms an azeotrope with water, then heated to reflux temperature, removing the water from the mixture by techniques such as azeotropic distillation, simple distillation, and the like, at atmospheric pressure or under reduced pressure, until water is substantially completely removed from the mixture. In embodiments, a substantially anhydrous pro-chiral sulphide of formula (II) having less than about 1% by weight, such as about 0.01 to 1%, or about 0.1 to 1%, of water is used for the reaction of step (a).
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