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WO 2008/122988 Al (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 PCT 16 October 2008 (16.10.2008) WO 2008/122988 Al (51) International Patent Classification: (74) Agents: SUBRAMANIAM, Hariharan et al; SUBRA- C07C 46/10 (2006.01) C07C 50/32 (2006.01) MANIAM, NATARAJ & ASSOCIATES, Patent & Trade mark Attorneys, E 556, Greater Kailash-II, New Dehli 110 (21) International Application Number: 048 (IN). PCT/IN2008/000216 (81) Designated States (unless otherwise indicated, for every (22) International Filing Date: 3 April 2008 (03.04.2008) kind of national protection available): AE, AG, AL, AM, AO, AT,AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, (25) Filing Language: English CH, 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, (26) Publication Language: English IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, (30) Priority Data: MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, 686/MUM/2007 5 April 2007 (05.04.2007) IN PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, (71) Applicant and ZA, ZM, ZW (72) Inventor: CADILA HEALTHCARE LIMITED (84) Designated States (unless otherwise indicated, for every [IN/IN]; Zydus Tower, Satellite Cross Roads, Amedad- kind of regional protection available): ARIPO (BW, GH, abad 380 015, Gujara (IN). GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (72) Inventors; and European (AT,BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, (75) Inventors/Applicants (for US only): VERMA, Shyam, FR, GB, GR, HR, HU, IE, IS, IT, LT,LU, LV,MC, MT, NL, Sunder [IN/IN]; Zydus Tower, Satellite Cross Roads, NO, PL, PT, RO, SE, SI, SK, TR), OAPI (BF, BJ, CF, CG, Ahmedabad 380 015, Gujarat (IN). PATEL, Dhi- CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG). πiant, Jasubhai [IN/IN]; Zydus Tower, Satellite Cross Roads, Ahmedabad 380 015, Gujarat (IN). DWIVEDI, Declaration under Rule 4.17: Shriprakash, Dhar [IN/IN]; Zydus Tower, Satellite Cross — as to applicant's entitlement to applyfor and be granted a Roads, Ahmedabad 380 015, Gujarat (IN). patent (Rule 4.17(U)) [Continued on next page] (54) Title: PROCESS FOR PREPARATION OF ATOVAQUONE AND THE CONVERSION OF CIS-ISOMER TO TRANS- ISO MER FIGURE I (57) Abstract: Substantially pure atovaquone and parocess for the preparation thereof is disclosed. Published: PROCESS FOR PREPARATION OF ATOVAQUONE AND THE CONVERSION OF CIS-ISOMER TO TRANS- ISOMER The present invention relates a process for the preparation of Atovaquone of formula (I). More particularly, the present invention relates to the process for the preparation of Atovaquone substantially free from its cis isomer. The present invention also provides the process for the preparation of purification of Atovaquone. BACKGROUND OF THE INVENTION Pneumocystis carinii is a parasite, which has a natural habitat in lung tissue, in a host with normal immune system. Without treatment Pneumocystis carinii pneumonia is almost always fatal in immune compromised host. U.S. Pat. No. 4,981,874 discloses the process of preparation and the activity of the Atovaquone. U.S. Pat. No. 5053432 disclosed route of synthesis of atovaquone. In condensation of 2-chloro-l, 4-naphthoquinone and 4-(4-chlorophenyl) cyclohexane-1- carboxylic acid in presence of silver nitrate and ammonium persulphate then extracted with chloroform also treated with acetonitrile gives a poor yield 35%. Here cis-isomer more generated, another disadvantage is last steps treated with KOH give 57% yield. Thus obtained Atovaquone so in this patent several disadvantages. The process for the preparation of Atovaquone was also reported in Tetrahedron Letters, Vol. 39, 7629-7632 (1998), article as shown in below scheme: As above disclosed process suffers with several drawbacks, as it requires to purification by recrystallization from acetonitrile. The solubility of Atovaquone in acetonitrile is very less and the high amount acetonitrile required. Moreover, it provides crystalline floppy material, which is difficult to handle at formulation development end. WO2006008752 discloses three polymorphic forms of Atovaquone designated as Form-I, Form-II and Form-Ill. The patent application discloses that Form-I is prior art form. OBJECTS OF THE INVENTION It is an important object of the present invention to provide a process for the preparation of Atovaquone of formula (I). Another object of the present invention is to provide a process for the preparation of Atovaquone substantially free of its c/s-ismer. Yet another object of the present invention is to provide a process for the purification of Atovaquone of formula (I). Another embodiment of invention cis-isomer converted to trans-isomer. BRIEF DESCRIPTION OF THE DRAWINGS FIG. I XRPD of cis-isomer of 2-Chloro-3-[4-(4-chloro-phenyl)-cyclohexyI]- [1,4]naphthoquinone. FIG. π DSC of cis-isomer of 2-Chloro-3-[4-(4-chloro-phenyl)-cyclohexyl]- [1,4]naphthoquinone. FIG. π i XRPD of trans-isomer of 2-Chloro-3-[4-(4-chloro-phenyl)-cyclohexyl]- [1,4]naphthoquinone. FIG. IV DSC of trans-isomer of 2-Chloro-3-[4-(4-chloro-phenyl)-cyclohexyl]- [1,4]naphthoquinone. FIG. V XRPD of Cis-isomer of Atovaquone. FIG. VI DSC of Cis-isomer of Atovaquone. FIG. VII XRPD of trans-isomer of Atovaquone. FIG. Vi π DSC of trans-isomer of Atovaquone. FIG. IX particle size of trans-isomer of 2-Chloro-3-[4-(4-chloro-phenyl)-cyclohexyl]- [l,4]naphthoquinone. FIG. X Particle size of Cis-isomer of Atovaquone. FIG. XI Particle size of trans-isomer of Atovaquone. FIG. XII HPLC graph of free from cis-isomer. DETAILED DESCRIPTION OF THE INVENTION As used herein the term "substantially pure atovaquone" means it contains less than about 0.1% of individual impurity. As used here in the term "atovaquone substantially Pure" means it atovaquone containing less than about 0.1% of cis-atovaquone. According to the present invention, there is provided a process for the preparation of Atovaquone of formula (I), which comprises the steps of (i) condensing 2-chloro-l,4-naphthoquinone of formula (II) with 4-(4- chlorophenyl)cyclohexane-l-carboxylic acid of formula (III) in presence of silver nitrate and ammonium persulfate to provide 2-[4-(4- chlorophenyl)cyclohexyl]-3-chloro-1,4-naphthoquinone of formula (IV) (II) (III) (ii) treating 2-[4-(4-chlorophenyl)cyclohexyl]-3-chloro-l,4-naphthoquinone of formula (IV) with alkali base in mixture of alcoholic solvent and halogenated solvent followed by treatment with mineral acid to provide Atovaquone of formula (I). (IV) The step of preparing the compound of formula (IV) by reacting 2-chloro-l,4- naphthoquinone of formula (II) with 4-(4-chlorophenyl)cyclohexane-l-carboxylic acid of formula (III) is carried out at a temperature in the range of 70-1000C, preferably, temperature range of 75-85°C. It is preferable to avoid solvent like sulpholane. This reaction condition gives high yield and purity. According to an embodiment of the present invention, 2-chloro-l,4-naphthoquinone of formula (II) is reacted with 4-(4-chlorophenyl)cyclohexane-l-carboxylic acid of formula (III) in the presence of silver nitrate and ammonium persulfate to provide 2-[4- (4-chlorophenyl)cyclohexyl]-3-chloro-l,4-naphthoquinone of formula (IV). The reaction is preferably carried out in polar solvent such as acetonitrile. Thus obtained 2- [4-(4-chlorophenyl)cyclohexyl]-3-chloro-l,4-naphthoquinone of formula (IV) may contain a mixture of cis and trans isomer. The ratio of trans: cis isomer may be in the range of 99:1 to about 1:99, preferably it may be in the range of 70:30 to 60:40 In another embodiment of present invention is formula (IV), any cis-isomer produced is converted to trans-isomer by dissolving it in organic solvent and heating it to reflux temperature. The organic solventa are selected from group comprising of ketones like acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl isopropyl ketone and methyl tert-butyl ketone; alcohols like methanol, ethanol, isopropyl alcohol and tert- butyl alcohol etc., esters like methyl acetate, ethyl acetate, n-butyl acetate, tert-butyl acetate, halogenated alkanes like dichloromethane, aromatic hydrocarbons like toluene, xylene etc., preferably xylene. The alkali metal base is selected from sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium tert-butoxide. The preferred alkali metal base is potassium hydroxide. According to an embodiment of the present invention, the solvent system of step (i) comprises of a mixture of alcoholic solvent and halogenated solvent. The preferred alcoholic solvent is selected from methanol, ethanol, n-propanol, isopropanol, n-butanol and halogenated solvent selected from methylene dichloride, ethylene dichloride, chloroform, carbon tetrachloride. An another embodiment of the invention is treating 2-[4-(4-chlorophenyl) cyclohexyl]-3-chloro-l,4-naphthoquinone of formula (IV) with alkali base in mixture of alcoholic solvent and halogenated solvent followed by treatment with mineral acid to provide Atovaquone of formula (I). In another embodiment of present invention is formula (IV), any cis-isomer produced is converted to trans-isomer by dissolving it in organic solvent and heating it to reflux temperature. m-Atovaquone rαns-Atovaquone The organic solvents are selected from group comprising of ketones like acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl isopropyl ketone and methyl tert-butyl ketone; alcohols like methanol, ethanol, isopropyl alcohol and tert- butyl alcohol etc., esters like methyl acetate, ethyl acetate, n-butyl acetate, tert-butyl acetate, halogenated alkanes like dichloromethane, aromatic hydrocarbons like toluene, xylene etc., preferably xylene.
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