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(12) United States Patent (10) Patent No.: US 9.233,966 B2 Dahanukar Et Al

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(12) United States Patent (10) Patent No.: US 9.233,966 B2 Dahanukar Et Al USOO9233966B2 (12) United States Patent (10) Patent No.: US 9.233,966 B2 Dahanukar et al. (45) Date of Patent: Jan. 12, 2016 (54) PREPARATION OF TICAGRELOR (2013.01); C07C 209/.44 (2013.01); C07C 209/48 (2013.01); C07C 253/30 (2013.01); (71) Applicant: DR. REDDY'S LABORATORIES C07C 255/46 (2013.01); C07B 2.200/07 LIMITED, Hyderabad (IN) (2013.01); C07C 2101/02 (2013.01) (72) Inventors: Vilas Hareshwar Dahanukar, (58) Field of Classification Search Hyderabad (IN); Goverdhan Gilla, None Hyderabad (IN); Sreenivasulu Kurella, See application file for complete search history. Hyderabad (IN); Shweta Mahajan Kulkarni, Hyderabad (IN); Raghupathi (56) References Cited Reddy Anumula, Hyderabad (IN); U.S. PATENT DOCUMENTS Sampath Aalla, Hyderabad (IN); Yakambram Boja, Hyderabad (IN); 6,525,060 B1 2/2003 Hardern et al. Ravi Ram Chandra Sekhar Elati, 7,067,663 B2 6/2006 Larsson et al. 7,122,695 B2 10/2006 Clarket al. Hyderabad (IN); Veerender Murki, 7,799,914 B2 9/2010 Larsson et al. Hyderabad (IN); Venkata Annapurna 7,863,469 B2 1/2011 Dejonghe et al. Sasikala Cheemalapati, Hyderabad (IN) 8,278.475 B2 10/2012 Mitsuda et al. 8,563,755 B2 10/2013 Bohlin et al. (73) Assignee: DR. REDDY'S LABORATORIES 2007/0173518 A1 7/2007 Bohlin et al. 2013,004O970 A1 2/2013 Cosgrove et al. LIMITED, Hyderabad (IN) 2013/O150577 A1 6, 2013 Khile et al. 2013,016.5696 A1 6, 2013 Khile et al. (*) Notice: Subject to any disclaimer, the term of this 2013,0317220 A1 11/2013 Nair et al. patent is extended or adjusted under 35 2014/0094.604 A1 4/2014 Kansal et al. U.S.C. 154(b) by 0 days. 2014/0148403 A1 5/2014 Cosgrove et al. (21) Appl. No.: 14/389,669 FOREIGN PATENT DOCUMENTS CN 102.249929. A 11, 2011 (22) PCT Filed: Apr. 5, 2013 WO 99.05.143 2, 1999 (86). PCT No.: PCT/B2013/052733 WO 2013,037.942 A1 3, 2013 S371 (c)(1), OTHER PUBLICATIONS (2) Date: Sep. 30, 2014 Disclosed Anonymously, "Amorphous Forms of (1S,2S,3R,5S)-3- I7-II(1R,2S)-2(3,4-difluorophenyl) cyclopropylamino-5- (87) PCT Pub. No.: WO2013/150495 (propylthio)-3H-1,2,3-triazolo 4.5.dpyrimidine-3-yl)-5-(2- PCT Pub. Date: Oct. 10, 2013 hydroxyethoxy)-1,2-cyclopentanediol. IP.com Prior Art Database online, IP.com No. IPCOMO00207885D retrieved on (65) Prior Publication Data Aug. 30, 2013). Electronic Publication Jun. 15, 2011, pp. 1 to 3. US 2015/OO73146 A1 Mar. 12, 2015 Retrieved from the Internet: http://ip.com/IPCOM/000207885. Written Opinion dated Sep. 26, 2013, for corresponding International (30) Foreign Application Priority Data Patent Application No. PCT/IB2013/052733. International Preliminary Reporton Patentability issued Oct. 7, 2014, Apr. 5, 2012 (IN) ... ... 1389/CHFA2012 for corresponding International Patent Application No. PCT/IB2013/ Jun. 5, 2012 (IN) ... ... 2254ACHEA2012 O52733. Jan. 4, 2013 (IN) ............................... 41 CHEA2013 International Search Report dated Sep. 26, 2013, for corresponding International Patent Application No. PCT/IB2013/052733. (51) Int. Cl. CO7D 47L/00 (2006.01) Primary Examiner — Jeffrey H Murray CO7D 487/00 (2006.01) (74) Attorney, Agent, or Firm — Pergament & Cepeda LLP: CO7D 49/00 (2006.01) Edward D. Pergament; Milagros A. Cepeda CO7D 487/04 (2006.01) CD7C 255/46 (2006.01) (57) ABSTRACT CD7C 209/244 (2006.01) Provided are processes for preparing Ticagrelor and its inter CD7C 209/248 (2006.01) mediates that are useful in the processes. Also provided are C07C 253/30 (2006.01) salts of Ticagrelor, their processes and Solid dispersion of A6 IK 9/14 (2006.01) Ticagrelor having Ticagrelor in amorphous form. (52) U.S. Cl. CPC .............. C07D 487/04 (2013.01); A61 K9/146 10 Claims, 13 Drawing Sheets U.S. Patent Jan. 12, 2016 Sheet 1 of 13 US 9.233,966 B2 -----it rrrrrt rrrrrr ; tri-rry - tri---'Tri-r-Trry-- -----,irrrrr! -i.-- & 3. E S; 3 r AISueu U.S. Patent Jan. 12, 2016 Sheet 2 of 13 US 9.233,966 B2 es 8 rur t N 3. d - st " Tss--- ... s. b N. -- rural......- r". it it it it TTF tit;rtrpriterrrrrrrrrrrrrrrrritpitfit infirm inimiprit Tirit Titir first r S Sg g a . Xix s: - ". 3 w t ^ r A Sueu U.S. Patent Jan. 12, 2016 Sheet 3 of 13 US 9.233,966 B2 3 r ry Tri-jiriiti rii - frry y q r y rr irrrrrrrrrrrrrt" tr. r s & w Asueu U.S. Patent Jan. 12, 2016 Sheet 4 of 13 US 9.233,966 B2 r l & -“E -- .." -asse. Y. CX tes -- re es. s". "-i". ". T-s e s es frt-t-per-fil-fi is --...------...------------ii "." fir?t Frt r r 1-rritory-tri-ry --r 3 c y S. S. KN w Asue, La U.S. Patent Jan. 12, 2016 Sheet 5 of 13 US 9.233,966 B2 t S. wn 9 c N garse --- ...-- ... as -it-1 first firri Tirit Ti-Trit rrrr rrrrrrrrrrrrri. In S.2 s co - c. - c. c. 3 4.v- s s $2 S r .2 e5 & is if it; i. 3 & C Asueu U.S. Patent Jan. 12, 2016 Sheet 6 of 13 US 9.233,966 B2 g ... ? - - : s ... g s O r O L roa SE: & c. - - irrtty, a gritt intr; -- ir irrrrris tii "Trri it in "T" i? if f IT" m Asueu U.S. Patent Jan. 12, 2016 Sheet 7 of 13 US 9.233,966 B2 s 3 ris acticialist-ir-user Iow" o N 9. d also - assic- se . -new " ". r: ". N N --- s asse" . Trrrrrrrri. It it it it it. It It in it trTrittrity trypt firfirirrt Y 3 g 3 3 3. 3 S t .. x w ASLeu U.S. Patent Jan. 12, 2016 Sheet 8 of 13 US 9.233,966 B2 S. O 1 Trrit triliittitt trirrtrirrty" t trfrt Trittni Trrrrrrrrrrrt firgin c c) c & s {} & k c d X a) s -- ca y k w w AISueu U.S. Patent Jan. 12, 2016 Sheet 9 of 13 US 9.233,966 B2 ...-------- "T"---it-isorsrtill it in Trimr irrirf fir?t r in -----------trir rift it tilti-Trymvrrrroww. rrrrrrrr,--- 4. w & R S; 3 S. 3 3. SR A Sueu U.S. Patent Jan. 12, 2016 Sheet 10 of 13 US 9.233,966 B2 y 3. r:: s sks. mitriri riterrittfritt. It It littitt irrirrirrtti titmirriTi Thirty tririt prrrrrrtti cs s Cs c c d k c s & s s s S3 3 s d Asue, u U.S. Patent Jan. 12, 2016 Sheet 11 of 13 US 9.233,966 B2 -i-riter Trrrrrrty-----, for r- - - - - - - - - ----- . 3 3 g w: - r Asueu U.S. Patent Jan. 12, 2016 Sheet 12 of 13 US 9.233,966 B2 3. R A Sueu U.S. Patent Jan. 12, 2016 Sheet 13 of 13 US 9.233,966 B2 f g o ul c w C P h N 1 - Irrrrrrrit Titirri"Frfirin-irrirrrrrrrrrturity try-rrrrrr, l P d o s K X s W- k Alsuou US 9,233,966 B2 1. 2 PREPARATION OF TICAGRELOR in the prior art does not have satisfactory purity and unaccept able amounts of impurities are formed along with Ticagrelor This application is a National Stage Application under 35 at various stages of the processes that are difficult to purify U.S.C. S371 of PCT International Application No. PCT/ and thus get carried forward in the Subsequent steps thus IB2013/052733, filed Apr. 5, 2013, which claims the benefit affecting the purity of final compound. of Indian Provisional Application Nos. 1389/CHF/2012, filed Processes for the preparation of the cyclopropyl based Apr. 5, 2012, 2254/CHF/2012, filed Jun. 5, 2012 and intermediate compound of Formula VIIa are described in 41/CHF/2013, filed Jan. 4, 2013, all of which are hereby Patent Application Publications. WO 01/92200 A1, WO incorporated by reference in their entireties. 2008/018823 A1, WO 2008/018822 A1, WO 2011/132083 10 A2 and WO 2012/001531 A2. These publications involve use INTRODUCTION of multi-step synthesis and/or use of chiral auxiliary for the preparation of the compound of Formula VIIa. The reported Aspects of the present application relate to processes for methods results in low yields, involve use of expensive chiral preparingticagrelor and its intermediates that are useful in the compounds, and further do not directly result in desired puri processes. The present application further relates to novel 15 ties of the intermediate compound of Formula VIIa. Thus salts of Ticagrelor, processes for their preparation and isola these processes may require an additional step of purification. tion. In addition, present application provides Ticagrelor Since the purity of intermediate compound play a major role salts, its solvates and hydrates thereof in crystalline form in deciding the efficiency of the process for final compound, and/or amorphous form. The application further relates to therefore there remains a need to prepare compounds of For Solid dispersions and compositions of Ticagrelor. mula VIIa of high purity and in good yield. Despite the efforts The drug compound having the adopted name “ticagrelor' of the research aimed at finding alternative routes, it would be has chemical names: 1S-(1C.2C.3 B(1S,2R).5 B)-3-7-2- desirable to study methods for preparing intermediate com (3,4-difluorophenyl-cyclopropylamino-5-(propylthio)-3H pound of Formula VIIa, which allow overcoming the draw 1,2,3-triazolo 4.5-dpyrimidin-3-yl)-5-(2-hydroxyethoxy)- backs presented by the processes described in the art.
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