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1 Supplement Custom Synthesis Your Source for igh Quality Products & Services Multiplicity Flexibility Partnership Trust Service Speed PharmaZell offers Active Pharmaceutical Ingredients (API) Advanced Intermediates Custom Synthesis (Development & Manufacturing) Analytical and Regulatory Services from laboratory scale to commercialization
2 Custom Synthesis at PharmaZell PharmaZell draws upon a long history of successful custom synthesis projects, performed on a proprietary basis for fine chemical and pharmaceutical companies worldwide. In addition to advanced intermediates (cgmp and non-cgmp), PharmaZell specializes in production of kilogram to multi-ton quantities of active pharmaceutical ingredients (APIs) for all stages of clinical trials through commercialization. Custom Synthesis
3 PharmaZell is now active on four sites Raubling, Germany Copenhagen, Denmark Chennai, India Vizag, India Site founded Production scale Pilot & commercial Pilot & commercial kg-lab & commercial Kg-Lab & commercial Employees* Compliance cgmp cgmp cgmp cgmp Total reactor volume (m 3 ) > expandable Key characteristics Group ead ffice Production of Controlled Substances Attractive labor & raw material cost structures Gradually expandable R&D center * umber of employees as per 31 st of December 2007
4 PharmaZell Site Raubling, Germany (close to Munich) API Production since 1947 Fully Integrated Site: - R&D, Pilot Plant, Commercial Production - QA/QC, Sales & Marketing - Project Assessment & Management Site Raubling FDA Inspected (1979,,,,,2004, 2007) Activities: Process Development Custom Manufacturing - of new APIs - of advanced Intermediates Analytical Method Development
5 Pilot plant at site Raubling, Germany (I) 900 m 2 working area on 3 levels, established in 2000, operates under cgmp (typical batch sizes kg) About 4,000 L total glass lined reactor capacity (from 70 L to 2,000 L reactor sizes) further expandable Pilot Plant Raubling Electrochemical & Electrodialysis plant (on demand) Distillation Unit, centrifuges, filter dryers, double cone dryer, tray dryer Pressure range 5 mbar vacuum to 10 bar pressure Temperature range -15 C to 230 C Controlled areas (class 100,000) for drying and handling of APIs
6 Equipment list Pilot Plant Raubling Pilot plant at site Raubling, Germany (II) Reactors (all reactors carry distillation heads) 70 L glass lined 100 L glass lined for hydrogenation and pressure reactions 350 L glass lined 500 L glass lined 800 L glass lined 2,000 L glass lined 200 L Stainless Steel Continous Plug Flow Reactor Filtration, Drying 0,25 m 2 Stainless Steel Agitated Filter Dryer 0,4 m 2 astelloy Agitated Filter Dryer Polypropylene Filter Press Stainless Steel Filter Press Basket Centrifuge, Stainless Steel ( 50 cm drum diameter) Basket Centrifuge, Corrosion Resistant, (80 cm drum diameter) Double Cone Dryer (400 L) Vacuum Tray Dryer Distillation: Distillation Column (3 m) with Fall Film Evaporator
7 Multi Purpose Equipment at site Raubling, Germany 44 m³ multi purpose stainless steel reactor capacity (800 L 5,000 L reactor sizes). 53 m³ multi purpose glass lined reactor capacity (2,000 L 14,000 L reactor sizes). Multi Purpose Plant Raubling 6 Multi purpose Basket Centrifuges, Automatic einkel Centrifuge, Filter presses, Stainless Steel Agitated Filter Dryer. Double cone dryers (1 m 3 ), 2 paddle dryers, Wyssmont dryer. Air Jet Mill, Micronization Unit. Pressure range 30 mbar vacuum to 10 bar pressure. Temperature range -10 C to 180 C
8 Finishing plant at site Raubling, Germany Completed in June separate production lines for crystallization, centrifugation, drying and milling Controlled areas for product handling Finishing Plant Raubling
9 GEA Pharmaceutical A/S Copenhagen, Denmark a PharmaZell company API Production since 1927 Fully Integrated Site: R&D, Pilot Plant, Commercial Production QA/QC/RA, Project Management cgmp compliant (product specific certificates) Site Copenhagen Activities: Process Development Custom Manufacturing - of new APIs - of Advanced Intermediates - including controlled substances (e.g. Amphetamines, pioids) Analytical Method Development
10 Multi Purpose Equipment at GEA site Copenhagen, Denmark Working area on 3 levels, pilot plant included in the plant, operates under cgmp (typical batch sizes kg) 16 reactors with about 29,000 L total capacity, 2/3 of which is glass lined (from 100 L to 5,000 L reactor sizes) Multi Purpose Plant Copenhagen 300 L ydrogenation reactor (up to 6 bar) 4 closed agitated filter dryers 1 fluidised bed opposed jet mill for micronizing Temperature range -40 C to 180 C Utility systems: -steam, cooling systems, pressurised air, nitrogen -solvent tank farm with direct pipeline to reactors.
11 PharmaZell Site Chennai, India Site Chennai Inauguration in % owned by PharmaZell German Management Attractive labor and raw material cost structure Fully Integrated Site (R&D, Kilo-Lab, Production, QA/QC) Activities: Process Development Custom Manufacturing Production - of mature APIs - and Intermediates Analytical Method Development
12 Kilo-Laboratory at site Chennai, India 200 m 2 working area, start-up 2004, (typical batch sizes 1-20 kg) 500 L total glass lined reactor capacity (50, 100 & 200 L reactor sizes) further expandable Kg-Plant Chennai Additional reactors: 2 glass (10L & 20 L) and 1 Stainless Steel 200 L 10 mbar vacuum Temperature range 10 C 150 C Centrifuges, double cone dryer, tray dryer Segregated area (controlled area) for drying and handling of finished products
13 Multi Purpose Equipment at site Chennai, India 23 m 3 glass lined reactor capacity (reactor volumes: 1,000 L 6,000 L) 41 m 3 stainless steel reactor capacity (reactor volumes: 500 L 6,000 L) Multi Purpose Plant Chennai 6 Centrifuges; between cm drum diameter, top and bottom discharge 3 Filter presses, 1 Sparkler Filter 2 Cone dryers; 2 Fluid Bed Dryers Stainless Steel 2 Blender/Stainless Steel Various Mills
14 Chemical Capabilities In general: Large toolbox of chemical reactions suitable for multi-step syntheses. Particular expertise in the field of: Chemical Capabilities verview Electrochemical Reactions Diazotization itration (100% itric Acid) ydrogenation alogenation Epichlorohydrine Chemistry Reactions with Acid Chlorides Amino Acid Chemistry Carbohydrate Chemistry Pyrimidines GEA specials Crystallization Milling and Micronization Controlled Substances (synthetic and opioid)
15 Chemical Capabilities Electrochemical Reactions - igh yields - Less waste compared to classical chemistry - igh selectivity - Low investment cost Chemical Capabilities e.g. Electrolysis with divided cell type Electrochemical reactions Cathode Anode S-S bonds -=-diazo compounds 2 -reduction/nitrocompounds
16 Chemical Capabilities Electrochemical Reactions e.g. Electrodialysis Chemical Capabilities Electrochemical reactions Anion Exchange Membrane Cation Exchange Membrane Separation of water soluble molecules and salts desalination of sugar solutions desalination of amino acids and derivatives
17 Chemical Capabilities Diazotization Technical expertise or the handling of Diazonium Salts as Suspensions and Solutions Chemical Capabilities 2 R C 2 / a 2 water, Cl R C 2 Diazotization C2 C2 2 + a2 3 S 3 S
18 Chemical Capabilities itration (100% 3 ) 3 100% 2 Chemical Capabilities C itration CF 3 CF % 2
19 Chemical Capabilities ydrogenation Pd/ 2 C2 C2 Chemical Capabilities 2 Pd/ 2 2 ydrogenation 2 Rai/ ydrazine 2 C2 C2 R2 R2 Rai/ 2 ee 96% R1 R1
20 + Chemical Capabilities Epichlorohydrine Chemistry Cl 2 C 3 Chemical Capabilities C 3 C 3 Epichlorohydrine Cl + 2 Cl 1.Epichlorohydrine 2. iso-propylamine 2
21 Chemical Capabilities Reactions with Acid Chlorides Cbz Chloride - Thionylchloride - Acetylchloride - Arylchlorides Chemical Capabilities R Arylchloride Aryl R Aryl Acetyl Chloride stereocontrolled Aryl Cl Aryl Acid Chlorides 3 C 2 S S 2 C 3 Cbz Chloride 3 C S S C R R 1 SCl 2 / R- R 1
22 Chemical Capabilities Amino acid chemistry: Cysteine and Derivatives Chemical Capabilities Amino acids S Thiazolidine-carboxylic acid-methylester Arg S Thiazolidine-carboxylic acid (D) S 2 L-Cysteine S 2 S D-Cysteine 2 Carbocysteinate S Thiazolidine-carboxylic acid-arginine-salt Lysin-Carbocysteinate Lysine--Acetylcysteinate S AC S 2 S-Methylcysteine
23 Chemical Capabilities Amino acid chemistry: Protected/activated Amino acids Examples Chemical Capabilities Amino acids Amino acids: Cysteine Tryptophan Tyrosine Arginine Asparagine Glutamine orleucine Lysine Protection/Activation: Boc (t-butyloxycarbonyl) Fmoc (9-Fluorenylmethyloxycarbonyl) Cbz (Carbobenzyloxy) pys-cl (3-itropyridinyl-2-sulfonylchlorid Z (Benzyloxycarbonyl) -SU (-hydroxysuccinimide) DCC (dicyclohexylcarbodiimide)
24 Chemical Capabilities Amino acid chemistry: Short Chain Peptides (liquid ph.), selected examples a.) Cholecystokinine (CCK) Fragments for modified CCK -Arg-Asp-Tyr(S3)-Thr-Gly-Trp-le-Asp-Phe-2 Chemical Capabilities Amino acids b.) Sweetener 2 C 2 c.) Fragments for Somatostatine PS-Lys-Thr-Phe-Thr-Ser-Cys-tBu PS-Lys-Asn-Phe-Phe-Trp- BC-Ala-Gly-Cys
25 Chemical Capabilities Carbohydrates Chemical Capabilities Carbohydrate chemistry Ms Mesylglucose 3 C 3 C Ms 3 C C 3 Glucose 3 C 3 C 3 C Diacetoneglucose C 3 Fructose C 3 C 3 3 C C 3 Diacetonefructose R R R:, Toluoyl Deosyribose -Alkyl R -Alkyl R R Cl R: Toluoyl Ribosides R R: Toluoyl
26 Chemical Capabilities Chemical Capabilities Pyrimidines Pyrimidines 5-Amino-orotic Acid 2 2 SKA 2 K R 1 R 2 6-Methyluracile - rotic Acid Salts M + 5-itrouracile 5-Aminouracile 2 rotic Acid 5-Methyluracile
27 Chemical Capabilities GEA specials Pd R Cl R Chemical Capabilities C 2 C 2 Cu Cl 2 Cl Cl GEA specials R ClS 3 R S 2 Cl R C 2 PCl 3 3 P 3 P R P
28 Process/Process Development Electrochemical Cells (Lab, pilot and commercial scale) Electrodialysis cells (Lab, pilot and commercial scale) Plug flow reactor (Lab & pilot scale) Processes Batch, Semi-batch and Continuous perations (all scales) Mettler Lab Max for Process development & Calorimetric data generation (lab scale) Micro-reactor (lab scale) Milling and Micronization (commercial scale) Crystal morphology and particle size control (all scales)
29 Client cooperation Close Customer Interaction in all Phases of Process Development Max. 4 L Scale Process Design Process ptimization Lab procedure Critical Parameters L Scale Scale up & Technical Adaptions Supply of Materials for Clinical Trials Stability Testing L Scale Process Validation Cleaning Validation DMF Filing (CTD Format)
30 KG Manufacturing in Europe and Asia: At your service over the lifecycle of an API riginator Generic Loss of share to Generics Reformulation/Extension Production sites on two continents European Sites Market launch Indian Sites ADA Patent expiry Years
31 Custom Synthesis at PharmaZell Depending on the needs of our customers, our services can be provided as comprehensive solutions or in modular form and it is up to our customers to decide for either distinctive parts or package solutions. We do believe in open and transparent communication; from Custom Synthesis ur Service Approach Consulting our customers in the early phases in order to offer optimum service packages to Establishing regular project related means of communication (e.g. reports, teleconferences) and to Finalization of the projects with the deliverables as agreed upon.
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