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WO 2014/064706 Al 1 May 2014 (01.05.2014) W P O PCT

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WO 2014/064706 Al 1 May 2014 (01.05.2014) W P O PCT (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 WO 2014/064706 Al 1 May 2014 (01.05.2014) W P O PCT (51) International Patent Classification: DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, C07C 233/00 (2006.01) C07C 237/00 (2006.01) HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, C07C 235/00 (2006.01) C07C 239/00 (2006.01) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (21) International Application Number: NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, PCT/IN20 12/000694 RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, (22) International Filing Date: TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, 22 October 2012 (22.10.2012) ZM, ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (71) Applicant: SYMED LABS LIMITED [IN/IN]; 8-3- UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, 166/6&7, II Floor, Sree Arcade, Erragadda, Andhra Pra TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, desh, Hyderabad 50001 8 (IN). EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, (72) Inventors; and TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, (71) Applicants : MOHAN RAO, Dodda [IN/IN]; 8-2- ML, MR, NE, SN, TD, TG). 293/82/A/202, D. No. 202, Opp. Jubilee International Club, Road No. 14, Jubilee Hills, Andhra Pradesh, Hydera Declarations under Rule 4.17 : bad 500033 (IN). ANNA REDDY, Ambati [IN/IN]; H. — as to applicant's entitlement to apply for and be granted a No. 1-1 18, Kachapur, Shankarapatnam, Karimnagar, patent (Rule 4.1 7(H)) Andhra Pradesh, 505470 (IN). — of inventorship (Rule 4.17(iv)) (81) Designated States (unless otherwise indicated, for every Published: kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, — with international search report (Art. 21(3)) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, (54) Title: PROCESSES FOR THE PREPARATION OF AGOMELATINE USING NOVEL INTERMEDIATES (57) Abstract: Provided herein are novel, commercially viable and industrially advantageous processes for the preparation of Agomelatine or a salt thereof, in high yield and purity, using novel intermediates. PROCESSES FOR THE PREPARATION OF AGOMELATINE USING NOVEL INTERMEDIATES FIELD OF THE INVENTION The present invention relates to novel, commercially viable and industrially advantageous processes for the preparation of agomelatine or a salt thereof, in high yield and purity, using novel intermediates. BACKGROUND OF THE INVENTION U.S. Patent No. 5,225,442 (hereinafter referred to as the '442 patent) discloses 1- alkoxy-2-(acylaminoethyl)naphthalene derivatives, processes for their preparation, pharmaceutical compositions comprising the derivatives, and method of use thereof. These compounds possess valuable pharmacological properties with regard to the central nervous system, particularly anxiolytic, antipsychotic and analgesic properties, and with regard to ovulation, cerebral circulation and immunomodulation. Among them, Agomelatine, chemically named N-[2-(7-methoxy-l-naphthalenyl)ethyl]acetamide, is an important antidepressant and useful for the treatment of major depressive episodes in adults. Agomelatine has dual pharmacological effects, which is not only the agonist of melatonergic system receptor, but also the antagonist of 5HT2c receptor. Agomelatine is represented by the following structural formula I: Agomelatine is marketed by Servier (Ireland) Industries Ltd. in Europe under the brand names VALDOXAN ® and THYMANAX®, and it is orally administered as tablets containing 25 mg of agomelatine. The synthesis of agomelatine was first described in the '442 patent and its corresponding European equivalent Patent No. EP 0447285 Bl. Various pjOcesses_fot-the--- preparation of agomelatine, its intermediates, and related compounds are described in U.S. Patent Nos. US 5,420,158, US 7,476,751, US 7,544,839, US 7,999,129, US 8,212,077 and US 8,143,449; PCT Publication Nos. WO 201 1/054917, WO 201 1/153939, WO 201 1/154140, WO20 12/046253, WO2012/093402, WO2012/127483, WO 2012/093225, WO 2012/1 13999 and WO 2012/070025; and Journal of Medicinal Chemistry 1992, 35(8), 1484-1486; and Synthetic Communications 2001, 31(4), 621-629. According to the '442 patent, N-[2-(7-methoxy-l-naphthalenyl)ethyl]acetamide (Agomelatine) is prepared by a process as depicted in scheme : Scheme 1: 7- et ox -1-tetrlone Ethylbromo acetate CI , 0 Ethyl (7-methoxy-1 ,2,3,4-tetrahydro- 1-naphthylidene)acetate Ethyl (7-methoxy- 1-naphthyl)acetate (7-Methoxy-1 -naphthyl) acetic acid (7-Methoxy-1 -naphthyl) (7-Methoxy-1-naphthyl) (7-Methoxy-1 -naphthyl) acetonitrile acetyl chloride acetamide Ethanolic ammonia Raney Ni, H 2-(7-Methoxy-1 -naphthyl) N-[2-(7-Methoxynaphth-1-yl) ethylamine ethyrjacetamide (Agomelatine) As per the process described in the '442 patent, agomelatine is prepared by reacting 7-methoxy-l-tetralone with ethylbromo acetate in the presence of activated zinc filings and benzene to produce ethyl (7-methoxy-l,2,3,4-tetrahydro-l-naphthylidene)acetate,_which_is- then subjected to dehydro-aromatization with sulfur at 5°C to produce ethyl (7-methoxy- l-naphthyl)acetate, followed by hydrolysis and subsequent acyl chlorination with thionyl chloride in chloroform to produce (7-methoxy-l-naphthyl)acetyl chloride, and then ammonification with aqueous ammonia to produce (7-methoxy-l-naphthyl)acetamide, which is then reacted with triflic anhydride in the presence of triethylamine to produce (7- methoxy-l-naphthyl)acetonitrile, followed by reduction with Raney Nickel under hydrogen pressure to produce 2-(7-methoxy-l-naphthyl)ethyl amine, which is finally acetylated with acetyl chloride in pyridine to produce agomelatine. The process for the preparation of agomelatine disclosed in the '442 patent suffers from various disadvantages such as the use of highly corrosive and toxic reagents like thionyl chloride, benzene, chloroform and pyridine; and involves the use of tedious and cumbersome procedures since it requires eight steps to synthesize agomelatine, thereby rendering the overall yield being less than 30% and making the process commercially unfeasible. Agomelatine obtained by the process described in the '442 patent does not have the satisfactory purity for pharmaceutical use. Unacceptable amounts of impurities are generally formed along with agomelatine. Most of the methoxy intermediates compounds, obtained according to the process described in the '442 patent, exist in the form of residues, which are not isolated as solids, and thus leading to the formation of unacceptable amounts of impurities which are persistent impurities and cannot be removed at final stage. According to U.S. Patent No. 7,544,839 (hereinafter referred to as the '839 patent), Agomelatine is prepared by a process as depicted in scheme 2: Scheme 2: As per the process described in the '839 patent, agomelatine is prepared by reacting 7-methoxy-l-tetralone with cyanoacetic acid in the presence of heptanoic acid and benzylamine to produce (7-methoxy-3,4-dihydro-l-naphthalenyl)acetonitrile, followed by dehydrogenation in the presence of hydrogenation catalyst Pd/C with allyl methacrylate as the dehydrogenating agent to produce (7-methoxy-l-naphthyl)acetonitrile, which is then subjected to reduction with Raney Nickel under hydrogen pressure in the presence of ammonium hydroxide to produce 2-(7-methoxy-l-naphthyl)ethanamine hydrochloride, followed by acetylation to produce agomelatine. The reported overall yield of the product is 72%. The process described in the '839 patent requires the use of expensive noble metal catalysts like Palladium on carbon and hazardous reagents like allyl methacrylate, which causes a lot of environmental pollution, for dehydrogenation of (7-methoxy-3,4-dihydro-l- naphthalenyl)acetonitrile to produce (7-methoxy-l-naphthyl)acetonitrile. Moreover, this step of dehydrogenation is difficult to reproduce and the yield of the resulting amine compound is very low. Furthermore, the methoxy intermediates obtained according to the process described in the '839 patent suffer from disadvantages since these methoxy intermediates are characterized by having low melting points. For example, the reported melting point for (7-methoxy-3,4-dihydro-l-naphthalenyl)acetonitrile is 48-50°C, and the reported melting point for (7-methoxy-i-naphthyl)acetonitrile is 83°C. Hence, the known methoxy intermediate compounds are not stable and they decompose at higher temperatures due to their low melting points, for example, when sulfur (which is a cheaper aromatizing agent) is employed as reagent for aromatization of (7-methoxy-3,4-dihydro-l- naphthalenyl)acetonitrile (this reaction requires heating the reactants at higher temperature 180-200°C) to produce (7-methoxy-l-naphthyl)acetonitrile, thus leading to the formation of unacceptable amounts of impurities, thereby decreasing the yield and purity of the product. Hence, the aromatization of (7-methoxy-3,4-dihydro-l-naphthalenyl)acetonitrile must be carried out at low temperatures and requires the use of expensive noble metal catalysts like palladium on carbon and additional hazardous reagents like allyl methacrylate. Therefore, the cheaper aromatizing agents like sulfur cannot be used for aromatization of known methoxy intennedjate _compounds The—time—periods—for completion of the reaction between 7-methoxy-l-tetralone and cyanoacetic acid takes around 30 hours at reflux temperature. According to U.S. Patent No. 8,212,077 (hereinafter referred to as the Ό 77 patent), Agomelatine is prepared by a process as depicted in scheme 3: Scheme 3: 2-(7-Methoxy-1 -naphthyl) Agomelatine ethanamine According to PCT Publication No.
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