Hamari Chemicals, Ltd.
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1 amari Chemicals, Ltd. Technology for Life 1
2 Agenda What amari can offer your company amari s Technology The amari Advantage Core Technology unnatural amino acids and peptides; reduction; chiral technologies; oxidation; alkylation and arylation; nucleic acid derivatives Limitations igh Potency Laboratory 2
3 amari can offer your company Cost performance, high quality, and environmentally friendly services More than 60 years of experience in custom manufacturing More than 60 reactions on commercial scale (500L to 5000 L) cgmp manufacturing facilities Process development, method validation and stability testing FTE: Full Time Equivalent study API development service for ID and DA 3
4 API Development Service Pre- Clinical Pre-ID ID Ph I Ph III DA PAI FDA/EMA Approval API is provided API is provided API is provided Stage 1 Stage 2 Stage 3 Stage 4 Stage 5 Stage 6 Stage 7 Inquiry Initial Study Process Development Pilot GLP Lot Process ptimization Manufacturing GMP Lot Validation Lot Commercial Analytical Development Stability Testing Method Validation 5 days 1-4 weeks 1-6 months 2 months Fastest case:glp pilot production started within 3 months 4
5 Timeline of ID Project Actual Example ID Project (Total 5 steps, GLP-API 2 Lot & GMP-API 1 Lot) Customer GMP audits Kg-Lab 1kg Analytical study 20g 3 GLP-API 1st 20Kg GLP-API 2nd 20Kg GMP-API 20Kg months Technical feasibility study, Raw material availability and Price idea Small samples for determining specification Analytical development Process development and Firm quotation for pilot quantities GLP Production and Reports Analytical method Validation Laboratory Kg-scale production Process optimization and Establishing specification GMP Production and Reports 5
6 amari s Core Technology Unnatural Amino Acids and Peptides Reduction Chiral Technology xidation Alkylation and Arylation Unnatural amino acid manufacture; liquid and solid phase peptide synthesis Reductive amination using metal catalysts Asymmetric Transfer ydrogenation Swern, XE,TEMP, Sharpless egishi, Suzuki-Miyaura, Mizoroki-eck, Mitsunobu reactions, lefin Metathesis ucleic Acid Derivatives API for antiviral agents or intermediates eterocyclics Indoles and Quinolines using itration alogenation Chlorination (PCl 3 ), Bromination (BS, Br 2 ) Etherification Phase transfer catalyst such as TBAB 6
7 Unnatural Amino Acids & Peptides (1) ACE Inhibitor Lisinopril ester (Europe) Anti-Ulcer Agent (in Japan) Polaprezinc (a amari original) Capacity: 20 tons / year Zn 2 Capacity: 30 tons / year Purity SSS isomer: > 99% RSS isomer: < 0.5% cgmp Intermediates for Anticancer Agents exa-peptide 150 kg / year Tri-peptide 30 kg / year 7
8 Unnatural Amino Acids & Peptides (2) Unnatural Amino Acid Derivatives Soloshonok Method V. Soloshonok et al. J. Am. Chem. Soc. 2009, 131,
9 Unnatural Amino Acids & Peptides (3) Ac Unnatural Amino Acid Derivatives for ovel Peptide Development Cl 2 2 Me S C 2 Ciluprevir (Macrocyclic epatitis C Virus S3 Protease Inhibitor) Degarelix (L-R antagonist) Vaniprevir (Macrocyclic epatitis C Virus S3 Protease Inhibitor) 9
10 Reduction Asymmetric Schiff Base Reduction ( 2 / Raney i, 30 tons / year) Reduction with DIBA at Commercial Scale 10
11 Chiral Technology (1) Asymmetric Transfer ydrogenation Me R Me R 1 R 2 R 1 R 2 85%ee R 1 R 2 R 1 S 95%ee R 2 Advantages R R R F F Me F 92%ee F 93%ee S Me 1) Remarkably high enantioselectivity 2) Simple structure 3) Easy handling 4) Unsusceptible to many contaminants 5) o special equipment needed 11
12 Chiral Technology (2) Application to API Synthesis S R Et 2 Me Cl tamsulosin Cl (arnal TM ) selective R 2 silodosin (Urief TM ) 1-adrenergic antagonist CF 3 Me F S C 2 levofloxacin (Clavit TM ) fluoroquinolone antibacterial agent CF 3 Me R arformoterol tartrate (Brovana TM ) 2-adrenergic agonist C C 2 C 2 R Cl selegiline Cl (EmsamTM ) selective MA-B inhibitor R F 3 C CF 2 CF 2 CETP inhibitor (drug candidate, J&J) 12
13 xidation amari has the Know-ow to safely handle xidative Reagents and Conditions CA ( 4 ) 2 Ce( 3 ) 6 TEMP Swern and related oxidations 13
14 Alkylation and Arylation (1) egishi Cross Coupling Manufacture Pilot plant: saka Manufacturing: 50 kg / Batch Residual Pd: MT 1 ppm level In accordance with cgmp Suzuki-Miyaura Cross Coupling Manufacture Commercial: Yonezawa Manufacturing: 100 kg / Batch Residual Pd: MT 1 ppm level In accordance with cgmp Mizoroki-eck Reaction Manufacture Commercial: Yonezawa Manufacturing: 100 kg / Batch Residual Pd: MT 1 ppm level In accordance with cgmp 14
15 Alkylation and Arylation (2) lefin Metathesis Vaniprevir (Macrocyclic epatitis C Virus S3 Protease Inhibitor) 15
16 ucleic Acid Derivatives API and Intermediates Me R Commercial Scale 16
17 Limitations Types of Chemistry that amari is Unable to Perform Precise Distillations for Purification igh temperature reactions (160 to 300 ) Phosgene Chemistry Reductions using Diborane xidations using zone Photo-Reactive Chemistry 17
18 igh Potency Laboratory saka Facility EL4 ccupational Exposure Limit 18
19 igh Quality Custom Manufacture: Pharmaceuticals, utriceuticals, Cosmeceuticals Weekly development reports and monthly teleconferences Thank you very much for your time and attention Your Partner for the Future 19
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