(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2019/049174 Al 14 March 2019 (14.03.2019) W 1P O PCT (51) International Patent Classification: (Mdl), Sangareddy (Dist), Telangana (State), Hyderabad C07D 239/54 (2006.01) 502307 (IN). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/IN2018/050583 kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, (22) International Filing Date: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, 07 September 2018 (07.09.2018) DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, (25) Filing Language: English HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, (26) Publication Language: English MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (30) Priority Data: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, 20174103 1748 07 September 2017 (07.09.2017) IN SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, 201741033391 20 September 2017 (20.09.2017) IN TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. 201841012427 02 April 2018 (02.04.2018) IN (84) Designated States (unless otherwise indicated, for every 201841015961 27 April 2018 (27.04.2018) IN kind of regional protection available): ARIPO (BW, GH, (71) Applicant: MSN LABORATORIES PRIVATE LIMIT¬ GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, ED, R&D CENTER [IN/IN]; Plot No. 12, Phase-IV, Sy UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, No. 119 to 140, 258, 275 to 280, IDA, Pashamylaram (Vill), TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, Patancheru (Mdl), Sangareddy (Dist), Telangana (State), EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, Hyderabad 502307 (IN). MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, (72) Inventors: SRINIVASAN, Thirumalai Rajan; Plot No. KM, ML, MR, NE, SN, TD, TG). 12, Phase-IV, Sy No. 119 to 140, 258, 275 to 280, IDA, Pashamylaram (Vill), Patancheru (Mdl), Sangareddy Declarations under Rule 4.17: (Dist), Telangana (State), Hyderabad 502307 (IN). SAJJA, — as to applicant's entitlement to apply for and be granted a Eswaraiah; Plot No. 12, Phase-IV, Sy No. 119 to 140, 258, patent (Rule 4.17(H)) 275 to 280, IDA, Pashamylaram (Vill), Patancheru (Mdl), — of inventorship (Rule 4.17(iv)) Sangareddy (Dist), Telangana (State), Hyderabad 502307 (IN). GHOJALA, Venkat Re y; Plot No. 12, Phase-IV, Published: Sy No. 119 to 140, 258, 275 to 280, IDA, Pashamylaram — with international search report (Art. 21(3)) (Vill), Patancheru (Mdl), Sangareddy (Dist), Telangana — in black and white; the international application as filed (State), Hyderabad 502307 (IN). SAGYAM, Rajeshwar contained color or greyscale and is available for download Reddy; Plot No. 12, Phase-IV, Sy No. 119 to 140, 258, 275 from PATENTSCOPE to 280, IDA, Pashamylaram (Vill), Patancheru (Mdl), San¬ gareddy (Dist), Telangana (State), Hyderabad 502307 (IN). RANGINENI, Srinivasulu; Plot No. 12, Phase-IV, Sy No. 119 to 140, 258, 275 to 280, IDA, Pashamylaram (Vill), Patancheru (Mdl), Sangareddy (Dist), Telangana (State), Hyderabad 502307 (IN). KOMMERA, Rajashekar; Plot No. 12, Phase-IV, Sy. No. 119 to 140, 258, 275 to 280, IDA, Pashamylaram (Vil),Patancheru (Mdl), Sangareddy (Dist), Telangana (State), Hyderabad 502 307 (IN). BEKKAM, Markandeya; Plot No. 12, Phase-IV, Sy No. 119 to 140, 258, 275 to 280, IDA, Pashamylaram (Vill), Patancheru (54) Title: SOLID STATE FORMS OF 5-CHLORO-6-[(2-IMmOPYP^OLroiN-l-YL)METHYL]PYRIMlDINE-2,4-(lH,3H)-DIO NE HYDROCHLORIDE AND THEIR PROCESSES FOR THE PREPARATION THEREOF (57) Abstract: The present invention relates to solid state forms of 5-chloro-6-[(2-iminopyrrolidin-l-yl) methyl]pyrimidine-2,4-(lH,3H)-dione hydrochloride compound of formula-la and their processes for the preparation thereof and an improved process for the preparation of 5-chloro-6-[(2-iminopyrro- lidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione hydrochloride. The present inventors also provides an amorphous polymorph of the combination drug consisting of 2'-deoxy-5-(trifluoromethyl) uridine and 5-cMoro-6-[(2-irmnopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione monohydrochloride and its process for the preparation. Solid state forms of 5-chloro-6 -r(2-iminopyrrolidin-l-yl)methyllpyrimidine-2,4- (lH,3H)-dione hydrochloride and their processes for the preparation thereof Related Applications: This application claims priority to Indian patent application numbers 201741031748 filed on September 07, 2017; 201741033391 filed on September 20, 2017; 201841012427 filed on April 02, 2018 and 201841015961 filed on April 27, 2018; the disclosure of which are incorporated herein by reference in its entirety. Field of the Invention: The present invention relates to solid state forms of 5-chloro-6-[(2-iminopyrrolidin-l- yl)methyl]pyrimidine-2,4-(lH,3H)-dione hydrochloride compound of formula- l a and their processes for the preparation thereof. Formula- 1a The present invention also provides an improved process for the preparation of 5- chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione hydrochloride. The present inventors also provides an amorphous polymorph of the combination drug consisting of 2'-deoxy-5-(trifluoromethyl) uridine and 5-chloro-6-[(2-iminopyrrolidin- l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione monohydrochloride and its process for the preparation. Background of the Invention: 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione hydrochloride, commonly known as Tipiracil hydrochloride has an inhibitory action on human thymidine phosphorylase and an enhancing action on the antitumor effect of Trifluridine. Tipiracil prevents rapid metabolism of Trifluridine, increasing the bioavailability of Trifluridine. An antitumor agent "TAS-102" composed of a mixture of Trifluridine and Tipiracil hydrochloride with a molar ratio of 1:0.5 was approved by United States Food and Drug administration (USFDA) on Sep 22, 2015 and by European medicines agency on April 25, 2016 as a therapeutic agent indicated for the treatment of patients with metastatic colorectal cancer. The said combination product is marketed under the trade name Lonsurf®. TAS-102 is structurally shown as follows: TAS-102 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione hydrochloride also known as 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4- (lH,3H)-dione monohydrochloride. Trifluridine is chemically known as 2'-deoxy-5-(trifluoromethyl) uridine and is first described in US3201387. US5744475 patent discloses the combination of 2'-deoxy-5-(trifluoromethyl) uridine and 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione mono hydrochloride in 1:0.5 molar ratio. The present inventors also have developed an amorphous polymorph of the combination drug consisting of 2'-deoxy-5-(trifluoromethyl) uridine and 5-chloro-6-[(2- iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione monohydrochloride and its process for the preparation. US5744475A describes 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4- (lH,3H)-dione hydrochloride, its analogs and process for their preparation. US9527833B2 of Taiho pharmaceuticals has described three crystalline polymorphic forms of 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione hydrochloride namely crystalline form-I, II and III and processes for their preparation. The present invention provides an improved process for the preparation of Tipiracil hydrochloride and its polymorphs. The present invention also provides a process for the purification of Tipiracil and its intermediate compound. Brief description of the invention: The first aspect of the present invention is to provide a novel crystalline polymorph of 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione hydrochloride compound of formula-la. The second aspect of the present invention is to provide a process for the preparation of novel crystalline polymorph of compound of formula- l a of the present invention. The third aspect of the present invention is to provide pure amorphous form of compound of formula-la. The fourth aspect of the present invention is to provide a process for the preparation of pure amorphous form of compound of formula- la. The fifth aspect of the present invention is to provide amorphous solid dispersion comprising compound of formula- l a and at least one pharmaceutically acceptable excipient. The sixth aspect of the present invention is to provide a process for the preparation of amorphous solid dispersion comprising compound of formula- l a and at least one pharmaceutically acceptable excipient. The seventh aspect of the present invention is to provide an improved process for the preparation of 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione hydrochloride compound of formula-la. The eighth aspect of the present invention is to provide a process for the purification of 5-chloro-6-(chloromethyl)pyrimidine-2,4(lH,3H)-dione compound of formula-3a, which is an useful intermediate for the preparation of compound of formula-la. The ninth aspect of the present invention is to provide a process for the purification of 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)-dione compound of formula- 1. The tenth aspect of the present invention is to provide a process for the preparation of crystalline form-I of 5-chloro-6-[(2-iminopyrrolidin-l-yl)methyl]pyrimidine-2,4-(lH,3H)- dione hydrochloride compound of formula-la.