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216000000 Malaria Events/106 Countries 655000 Deaths/Y 1 216,000,000Malariaevents/106countries216,000,000Malariaevents/106countries 655,000deaths/y,86%<5y655,000deaths/y,86%<5y EURARTESIM® aninternationalstory with anItalian plot EURARTESIM® aninternationalstory with anItalian plot AjourneyfromArtemisia’sFieldstoDHA/PQPinpatients AjourneyfromArtemisia’sFieldstoDHA/PQPinpatients Corporate Preclinical Development Page 2 TheScientiststhatunderstoodthediseaseTheScientiststhatunderstoodthedisease Alphonse Laveran Ettore Marchiafava Angelo Celli Camillo Golgi THECULPRIT THERESULT Giovan Battista Grassi Amico Bignami Giuseppe Bastianelli THEVECTOR Sir Patrick Manson Sir Ronald Ross Corporate Preclinical Development Page 3 Corporate Preclinical Development Page 4 Italy:EradicationItaly:Eradication of of Malaria Malaria Italy&MalariaItaly&Malaria DeathsxmillionDeathsxmillion StateQuininedistributionStateQuininedistribution educationeducation Frank M. Snowden 2006, YaleUniversity Press, NewHaven AgroPontinoAgroPontino reclamationreclamation DDTDDT Corporate Preclinical Development Page 5 Corporate Preclinical Development Page 6 SigmatauSigmatau contribution contribution MedicineforMedicinefor MalariaVenturetarget MalariaVenturetarget SeveremalariaUncomplicated malaria IVARTESUNATEEurartesim® FDA EMA Validation batches comlpeted REGISTERED Corporate Preclinical Development Page 7 Corporate Preclinical Development 2-6 July 2012 Page 8 Drug Discovery &Development RepositioningRepositioning Drug Discovery &Development PfizerAzithromycin based combination. ProcessDevelopment&Lifecyclemanagement NewChemical Entities MedicinalChemistry Microdosing NewChemical Entities DrugDiscovery Early GSKTafenoquine Phase II/III Genomic Lead to Phase IV DELAY Target Screen Hit to Candidate Clinical Clinical Clinical & Target Early Launch & GENERIC to Drug Phase I identification Validation to Hit Lead Candidate Phase II Phase III COMPETITION Candidate PMS Rambaxy Arterolane registered only inIndia… Candidate: A compound that has demonstrated in vivo efficacy & safety, whose synthesis can be scaled up economically Shin Poong Pharm.Pyramax ,EMAdecision based onarticle Lead: A compound with appropriate potency, selectivity, 58on17/2/201 pharmacokinetics, physical properties, novelty and acceptable toxicity profileforfulloptimisation Hit:Acompoundwithcleardoseresponseactivityinaprimaryscreen,known VaccineVaccine confirmedstructureandpreliminarySARinformation Protection efficiency? Validatedtarget:Aproteinoraclearbiologicaltargetwithknownfunction,disease GSKSuccesfull phaseIIItrials. associationandinvolvement. Corporate Preclinical Development Page 9 Corporate Preclinical Development Page 10 Combinations!!!Better use of theavailable weapons 2010FDAAPPROVAL2010FDAAPPROVAL Combinations!!!Better use of theavailable weapons ArtemisininbasedArtemisininbased Combination Combination Therapies Therapies Combinations Vaccines Artemisinins Quinine Pyrimethamine Piperaquine Mefloquine 12 5 2010 NatureReview inDrug Discovery 2011, 10,82. Corporate Preclinical Development Page 11 Corporate Preclinical Development Page 12 Combinations!!!Combinations!!! BetterBetter use use of of the the availableavailable weapons weapons FixedFixed DoseCombinations!!!! DoseCombinations!!!! PRODUCT COMPANY FIRSTAPPROVAL Artemisinin-basedArtemisinin-based Combination Combination Therapies Therapies Coartem® Novartis Switzerland Artemisinins Quinine Artemether &Lumefantrine Pyrimethamine Piperaquine 1980/1970 Mefloquine Coarsucam® Sanofi Morocco Artesunate &Amodiaquine 1980/1946 Eurartesim® Sigmatau EMA DHA&Piperaquine 1980/1960 Corporate Preclinical Development Page 13 Corporate Preclinical Development Page 14 TraditionalChineseMedicineTraditionalChineseMedicine OnlyOnly 541Scientists 541Scientists Were Were Exempt Exempt FromFrom theReeducation theReeducation Process Process Qng Ho ArtemisiaAnnua Beijing: Project523HeadOffice Biophysics CASInst. 1971-1974 Traditional Chinese MateriaMedicaInst. Jinan: MateriaMedicaInst. QUINGHAOSU Parasitic Diseases Inst. Artemisinin 哴 㣡 㫯 Shanghai: MateriaMedicaCASInst. Organic Chemistry Inst. H Chongqing: SichuanMateriaMedicaInst. O O 1977 Jiansu Province: Gaoyou Country Health Dept. O H Guangzhou: Univ.of Chinese Traditional Medicine O Kunming: Yunnan MateriaMedicaInst. O Guilin: Guiling Pharmaceutical Factory Corporate Preclinical Development Page 15 Corporate Preclinical Development Page 16 THEFIRSTTODISCOVERANDSHARETHEFIRSTTODISCOVERANDSHARE Milutin Stefanovic Corporate Preclinical Development Page 17 Corporate Preclinical Development Page 18 EURARTESIM® ArtemisininArtemisinin derivatives derivatives EURARTESIM® O O P P H HO OH HO OH OH OH Cl O Cl PIPERAQUINEPOSPHATE N N O (PQP) O artemether N N H O O 5 H 7 H 4 O N 2 Coartem N 3 O 8 O O P 1 P HO OH O 9 O HO OH OH O O cGMP OH H H cGMP O O H O OH O H O artemisinin DHA O O H artesunate DIHYDROARTEMISININ O O (DHA) O O H O thedrug HO H O O Eurartesim Coarsucam OH Corporate Preclinical Development 2-6 July 2012 Page 19 Corporate Preclinical Development Page 20 TheThe MalariaCycle MalariaCycle PotentialTargetsArtemisininPotentialTargetsArtemisinin Derivatives Derivatives N Heme N N Cl Protein Mitochondria schizogony alkylation N Cl N t O 2 H ½ N 22d 1 O O O O O 3 H O H O O Erythrocites O schizogony O H H Parasite O PfATP6 (SERCA) membranes OR t ½ 1h Corporate Preclinical Development 2-6 July 2012 Page 21 Corporate Preclinical Development Page 22 ParasitaemiaandfeverclearanceParasitaemiaandfeverclearance TotalQualityTotalQuality Preclinical Development GLPGLP Clinical Development GCPGCP DS/DP GMPGMP EH&SEH&S GREENCHEMISTRYGREENCHEMISTRY Corporate Preclinical Development 2-6 July 2012 Page 23 Corporate Preclinical Development Page 24 EURARTESIMLOGISTICSEURARTESIMLOGISTICS ArtemisiaannuaArtemisiaannuaFIELDSFIELDS China Vietnam Collaboration with the Kenya InternationalPharmacopoeia Artemisinin Collaboration with theInternational GMP Pharmacopoeia andtheUSP Supplier 1 Suppliers 2 DHA PQP SigmaTau Drug Product Corporate Preclinical Development Page 25 Corporate Preclinical Development Page 26 ArtemisininArtemisinin WW THEKEYPHARMACOPHORICTHEKEYPHARMACOPHORIC ArtemisininArtemisinin WW 1972.Artemisinin isolation.Milutin Stefanovic 1979.Artemisinin identification.Chinese Research Group Pharmacophoric mojety 2007. Identification and isolation of all the impurities by O2 + light Sigmatau .J.Chromatogr.A 2011,1218, 6838. Artemisiaannua glandular trichomes ArtemisininArtemisinin artemisinin epi-artemisinin artemisitene Response factor 11 37 Corporate Preclinical Development Page27 27 Corporate Preclinical Development Page 28 DHAThe Process DHAThe Process Molecules 2010,15, 13091323 Review Stereodynamic InvestigationofLabileStereogenic Centres inDihydroartemisinin IlariaD’Acquarica 1,*,FrancescoGasparrini 1,*,Dorina Kotoni 1,MarcoPierini 1, NaBH4 ClaudioVillani1,WalterCabri2,MichelaDiMattia2andFabrizioGiorgi2 1DipartimentodiChimicaeTecnologiedelFarmaco,SapienzaUniversità diRoma,P.leAldoMoro5 methanol 00185Roma,Italy 2Analytical Development,R&D Department,sigmatauS.p.A.,ViaPontinakm30,400,00040 Pomezia,Italy Artemisinin DHA crude crystallization DHA pure Corporate Preclinical Development Page 29 Corporate Preclinical Development 2-6 July 2012 Page 30 JOC 2011,76, 1751–1758 JOC 2011,76, 4831–4840 Corporate Preclinical Development 2-6 July 2012 Page 31 Corporate Preclinical Development 2-6 July 2012 Page 32 PQPTHEPROCESSPQPTHEPROCESS H+ H+ Ref lux 7-Chloro-4-[4- (3-piperazin-1-yl- propyl)-piperazin- 1-yl]-quinoline 1-Br-3-Cl-propane MW 157.44 7-Cl-4-[4-(3-Cl-propyl)- Piperaquine tetraphosphate tetrahydrate 4,7-DI Chloro-quinolin piperazine Piperaquine tetraphosphate tetrahydrate 4-piperazinyl 7-Cl-quinoline piperazin-1-yl]-quinoline MW =198.05 MW 86.14 MW 247.73 H3PO4, H2O 90 30° ° 4,4'-(propane-1,3-diylpiperazine-4,1-diyl)bis(7-chloroquinoline) tetrakis (phosphate) tetrahydrate PQP MW 999.56 4 X H2O Corporate Preclinical Development Page 33 Corporate Preclinical Development Page 34 Cl Cl N N WeWe Achieved Achieved : : N N N N Cl N N N N Complete control of the processes, the logistic. N N N Cl Cl Identification and control of all decomposition pathways. N N All impurities have been qualified from a toxicological N Cl O point of view. Genotoxic evaluation was generated Piperaquine HPLCmethod N according to the more recent ICH, EMA and FDA Cl N N OH guidelines. N N Our suppliers have established a complete N Cl N Environmental, Health and Safety control. Cl N Satisfactory 2y stability data at 30㼻 Cl N Cl Cl N N N N 0 5 10 15 20 25 30 Eurartesim®Eurartesim® is is free free from from genotoxic genotoxic impurities impurities minutes Corporate Preclinical Development Page 35 Corporate Preclinical Development Page 36 PhaseIIItrialinAfrica:5countriesPhaseIIItrialinAfrica:5countries Manhiça,MozambicoManhiça,Mozambico 278patientsi 301patients 223patients 304patients 447 patients Corporate Preclinical Development Page 37 Corporate Preclinical Development Page 38 DoseRegimensDoseRegimens for for children children EurartesimisequivalenttoCoartem28dEurartesimisequivalenttoCoartem28d Coartem (6doseregimenforchildren>15<25Kg:12tabletsover56hours) 100 94.7 95.3 92.0 Population “ Per Protocol” 08 Morning Evening Morning Evening 90 81.0 Day 1 Day 2 Day 3 80 70 p<0.001 p=NS Eurartesim (3doseregimenforchildren>13<23Kg:3tabletsover48hours) 60 97.5%CI>7. 97.5%CI> -3.0 6 50 0 24 48 uncorrected PCR-corrected Day 1 Day 2 Day 3 Eurartesim Coartem Corporate Preclinical Development Page 39 Corporate Preclinical Development Page 40 EurartesimprotectthepatientbetterthenCoartemfromEurartesimprotectthepatientbetterthenCoartemfrom
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