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Wo 2008/035381 A2

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Wo 2008/035381 A2 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date PCT (10) International Publication Number 27 March 2008 (27.03.2008) WO 2008/035381 A2 (51) International Patent Classification: (74) Agent: AGGARWAL, Asha; Ind-Swift Laboratories C07C 209/50 (2006.01) Limited, E-5, Phase- ϋ , Industrial Area, Phase II, S.A.S Nagar, Mohali 160 055, Punjab (IN). (21) International Application Number: PCT/IN2007/000416 (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, (22) International Filing Date: AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, 18 September 2007 (18.09.2007) CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, (25) Filing Language: English IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, (26) Publication Language: English MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, (30) Priority Data: TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, 2104/DEL/2006 22 September 2006 (22.09.2006) IN ZM, ZW 2458/DEL/2006 15 November 2006 (15.11.2006) IN (71) Applicant (for all designated States except US): (84) Designated States (unless otherwise indicated, for every IND-SWIFT LABORATORIES LIMITED [IN/IN]; kind of regional protection available): ARIPO (BW, GH, E-5, Industrial Area, Phace-II, S.A.S. Nagar, Mohali 160 GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, 055, Punjab (IN). ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, (72) Inventors; and FR, GB, GR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, PL, (75) Inventors/Applicants (for US only): SRINIVASAN, Chi¬ PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, CI, CM, dambaram, Venkateswaran [IN/IN]; Ind-Swift Labora GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). tories Limited, E-5, Industrial Area, Phace-II, S.A.S. N a gar, Mohali 160 055, Punjab (IN). JOHAR, Perminder, Declaration under Rule 4.17: Singh [IN/IN] ;Ind-Swift Laboratories Limited, E-5, Indus — of inventorship (Rule 4.17(iv)) trial Area, Phace-II, S.A.S. Nagar, Mohali 160 055, Pun jab (IN). WADHWA, Lalit [IN/IN]; Ind-Swift Laborato Published: ries Limited, E-5, Industrial Area, Phace-II, S.A.S. Nagar, — without international search report and to be republished Mohali 160 055, Punjab (IN). upon receipt of that report (54) Title: PROCESS FOR THE PREPARATION OF AMINE DERIVATIVES AS CALCIMIMETICS . π (57) Abstract: The present invention relates to a novel process for preparing amine derivatives of formula (I), and pharmaceutically acceptable salts and complexes thereof, wherein Ar1OrAr2 is either naphthyl orphenyl optionally substituted with 0 to 5 subslituents each independently selectedfrom the group consisting of lower alkyl, halogen, lower alkoxy lower thioalkyl, methylene dioxy lower haloalkyl, lower haloalkoxy, OH, CH2OH, CONH2, CN, acetoxy; q is 0-2; and R is H, by reducing novel amide intermediates of formula (II) wherein Ar1, Ar2 andqare same as described above. Particularly the present invention relates to an industrially advan tageous process for the preparation of cinacalcet hydrochloride of formula (III) using novel amide intermediate of formula (VIII), wherein X is H, halo like chloro, bromo or iodo. PROCESS FOR THE PREPARATION OF AMBSTE DERIVATIVES AS CALCIMIMETICS FIELD OF THE INVENTION The present invention relates to a novel process for preparing amine derivatives of formula I, as calcimimetics, Formula I wherein Ar\ or Ar2 is either naphthyl or phenyl optionally substituted with 0 to 5 substitiienls each independently selected from the group consisting of lower alkyl, halogen, lower alkoxy, lower thioalkyl, methylene dioxy, lower haloalkyl, lower haloalkoxy, OH, CH2OH, CONH2,, CN, acetoxy; q is 0-2; and R is H and pharmaceutically acceptable salts and complexes thereof, by reducing novel amide intermediates of formula II Formula II wherein Ar , Ar and q are same as described above. Particularly the present invention relates to an industrially advantageous process for the preparation of cinacalcet hydrochloride. The present invention also relates to novel synthetic intermediates useful in the process of the present invention. The present invention also relates to novel crystalline forms of cinacalcet hydrochloride and processes for preparing the same. BACKGROUND OF THE INVENTION Calcimimetics are small organic molecules that act as allosteric activators of the calcium sensing receptor (CaSR) in the parathyroid glands and other tissues. They lower the threshold for CaSR activation by extracellular calcium ions and diminish parathyroid hormone (PTH) release from parathyroid cells. By targeting the molecular mechanism that modulates PTH secretion on a minute-to-minute basis, calcimimetic compounds offer a novel approach to managing excess PTH secretion in several clinical disorders. Amine derivative of formula I were disclosed in PCT application WO 94/18959, United States patent nos. 6,21 1,244, 6,313,146, 6,031,003, 6,001,068, 6,01 1,884, 5,962,314, 5,858,684, 5,841,368, 5,763,569, 5,688,938 etc. T Formula I wherein Ar or Ar2 is either naphthyl or phenyl optionally substituted with 0 to 5; q is 0-2; and R is H, q is 0-2; and R is H, lower alkyl. The method disclosed in the above patents for the preparation of these compounds includes the reductive amination of a commercially available aldehyde or ketone with a primary amine in the presence of sodium cyanoborohydride or sodium triacetoxyborohydride and titanium isopropoxide. Alternatively some compounds were prepared from the condensation of a primary amine with an aldehyde or ketone in the presence of titanium (IV) isopropoxide. The resulting intermediate imines were then reduced in situ by the action of sodium cyanoborohydride, sodium borohydride, or sodium triacetoxyborohydride. Optionally the intermediate enamine was catalytically reduced using palladium dihydroxide on carbon. Various compounds were prepared by a diisobiitylaliiminum hydride (DIBAL-H) mediated condensation of an amine with a nitrile. The resulting intermediate imine is reduced in situ by the action of sodium cyanoborohydride or sodium borohydride. The intermediate alkenes were reduced by catalytic hydrogenation in ethanol using palladium on carbon. Further the compounds obtained were converted to their corresponding salts by treatment of the free base with acid in a suitable solvent. The prior art processes use expensive reagents and are not amenable to an industrial scale up. An important drug that acts as a calcimimetic agent is cinacalcet hydrochloride of formula III and is chemically known as -(l-naphthaIen-l-yIethyl)-3-[3-(trifIuoromethyl)phenyl]-propa π- 1-amine hydrochloride. Formula HI Cinacalcet hydrochloride is used to treat hyperparathyroidism (elevated parathyroid hormone levels), a consequence of parathyroid tumors and chronic renal failure. The above patents are completely silent about the specific process for the preparation of cinacalcet. Further, the above patents provide only the mass spectral data; otherwise the patents are unable to touch upon the physicochemical characterization data of cinacalcet and its salts thereof. The patents do not disclose any possibility or observation that the compound exists in different polymorphic forms. Consequently, there is an ongoing search for new polymorphic forms of drugs, which may provide for improved performance thereof. ' A single molecule, such as cinacalcet hydrochloride, may give rise to a variety of crystalline forms having distinct crystal structures and physical properties, such as melting point, X-ray diffraction pattern, infrared absorption fingerprint, and solid state NMR spectrum. There is a widely recognized need for, and it would be highly advantageous to have new and distinct crystalline forms of cinacalcet hydrochloride. In view of this, it is the principal object of the present invention to provide an efficient and novel process for the preparation of pure amine derivatives of formula I, which is unique with respect to its simplicity, cost effectiveness and convenience to operate on industrial scale. Another object of the present invention is to provide novel intermediates that play a crucial role in the preparation of amine derivatives as calcimimetics. Another main object of the present invention is to provide an efficient and cost-effective method for the preparation of highly pure cinacalcet hydrochloride in high yield. Yet another object of the present invention is to provide novel crystalline forms of cinacalcet hydrochloride and processes for preparing the same. SUMMARY OF THE INVENTION Accordingly, the present invention teaches an efficient and industrially advantageous process for the preparation of amine derivative of formula 1 L Formula I wherein Ar/ and A r is either naphthyl or phenyl optionally substituted with Oto 5 substitiients each independently selected from the group consisting of lower alkyl, halogen, lower alkoxy, lower thioalkyl, methylene dioxy, lower haloalkyl, lower haloalkoxy, OH, CFLOH, CONH2,, CN, acetoxy; q is 0-2; and R is H, and pharmaceutically acceptable salts and complexes thereof by reducing novel amide intermediate of formula II, N Ar2 l Formula II wherein Ari, Ar2 and q are as described above. Another object of the present invention is to provide a process for the preparation of amide intermediate of formula II F θ l lπ ula wherein Ar], Ar and q are as described above, which comprises introducing an acyl group of the formula IV, o— Ar 1- Formula IV wherein X = H or halo, wherein halo can be chloro, bromo or the like; is as described above, into the amino group of molecule of formula V or a salt thereof.
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