We will begin momentarily at 2pm ET · 2014-12-08 · Your source for leadership development,...

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7/31/2014 1 We will begin momentarily at 2pm ET Recordings will be available to ACS members after two weeks http://acswebinars.org 1 Contact ACS Webinars ® at [email protected] Type them into questions box! 2 “Why am I muted?” Don’t worry. Everyone is muted except the presenter and host. Thank you and enjoy the show. Contact ACS Webinars ® at [email protected] Have Questions?

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We will begin momentarily at 2pm ET

Recordings will be available to ACS members after two weeks

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Contact ACS Webinars ® at [email protected]

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Have you discovered the missing element?

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Find the many benefits of ACS membership!

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NEW! ACS Career Navigator Your source for leadership development, professional education, career services, and much more.

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College of Pharmacy, Washington State University

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Beginning in 2014 all recordings of ACS Webinars

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Upcoming ACS Webinars www.acs.org/acswebinars

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®

Contact ACS Webinars ® at [email protected]

Thursday, August 7, 2014

“How to Write Abstracts that Capture

Your Audience”

Celia Elliott, University of Illinois at Urbana-Champaign

Patricia Blum, University of Illinois at Urbana-Champaign

Thursday, August 21, 2014

“Forecasting Chemistry: Predicting

Tomorrow’s Cutting Edge Science, Today”

Dr. Charles Twardy, SciCast Project Principal and Professor

at George Mason University

www.acs.org/content/acs/en/events/acs-webinars/drug-discovery-series-2014.html 12

Did you miss the past recordings

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Next in the Drug Discovery Series!

13

“Pharmacoeconomics and IP Strategies

in Drug Development”

Thursday, September 25, 2014

Contact [email protected] for a copy of today’s slides 14

The Role of Chemistry in Clinical Trials:

The Big Expense & Lessons Learned

Recordings will be available to ACS members after two weeks

www.acswebinars.org

Dr. John Morrison Senior Research Investigator,

Bristol-Myers Squibb

Dr. Graham Johnson President, NuPharmAdvise LLC

Dr. Jay Sisco Founder, JM Sisco Pharma Consulting LLC

Past-President, AAPS

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The Role of Chemistry

in Clinical Trials

An ACS Webinar Presented by:

Dr. Graham Johnson – NuPharmAdvise, LLC

Dr. John M. “Jay” Sisco – JM Sisco Pharma Consulting, LLC

Moderated by Dr. John Morrison – Bristol-Myers Squibb

Our Objective

• Create awareness and understanding of what

happens between lead candidate selection and

NDA submission that translates into better drug

design and lead candidate selection

• A small investment up front can translate into

huge savings later on

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Post-

marketing Safety

Proof of

efficacy

Large safety and

efficacy

Discovery to Launch

Registration Phase 3 Phase 2

Toxicology

Phase 1

Approval

Submission

Launch

Development Discovery/Research

Clinical Trials

• The sole objective of clinical trials are to define

the safety, tolerability/side effects, effectiveness

and dose of a new drug and create the

knowledge base on which the FDA can approve

its use and sale.

• The “chemistry” of a new drug makes up a

critical part of this knowledge base

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Drug Product Development

• Facilitation of repeated safe delivery of the

correct quantity of active substance at the

correct rate to the desired body compartment

• Guaranteed until the expiry date

Every Time

Chemistry, Manufacturing & Controls

• Chemical R&D: reliable, reproducible, scalable synthetic API process

• Pharmaceutical physicochemical properties of the API, drug product

R&D: phase appropriate formulations – stable and deliver the

correct dose

• Analytical R&D: analytical methodologies - release testing and stability

evaluation of API and drug product.

• Quality: ensures compliance - regulations that govern the

manufacture, analysis, packaging, labeling and shipping

of API and drug product.

• Reg.CMC: author CMC section of submissions, interact with

regulatory authorities on matters concerning CMC

• Supply Chain: manufacture, package, label and ship clinical trial material

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What is the Chemistry of a Drug

• To the FDA

– A stable active pharmaceutical ingredient

(API) that can be made in completely defined

and controlled process that produces a

product of consistent purity, chirality, stability

and physical form

• To the Company

– A compound that can be consistently made by

a process that provides the greatest profit

margin or lowest “Cost of Goods”

Bridging the Divide

• Medicinal chemistry - the interface of organic chemistry

with biological systems. The objective is the discovery of

new drugs through the generation of structural diversity

and understanding its relationship to biological activity

• Process chemistry - the interface of organic chemistry

with business. The objective is the manufacture of a

specific molecule and a defined form with a high degree

of quality both cost effectively and with low

environmental impact.

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Different Strokes for Different Folks

• To the Medicinal Chemist

– The product is the driver! – how it is made and what

goes on in the flask is of less importance

• To the Process Chemist

– The process is the driver – understanding and

controlling every facet of what goes on in the flask is

critical

• To the Formulation Chemist

– The properties are the driver – creating an active

and commercially viable formulation depends on them

Operating in Different Worlds

Discovery Chemistry

– All reaction types, reagents and solvents are on the

table – if you can buy it you can use it!

– Temperatures from -110 to + 300 – no problem!

– Reaction concentration – what is that?

– Specialized equipment – high pressure

hydrogenation, microwave reactors – absolutely

we’ve got that!

– Purification – HPLC does the trick every time!

– Safety – if I am not working with diazomethane or

HF why do I need to worry?

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Operating in Different Worlds

Process Chemistry

– Safety is a primary driver

– Stability, toxicity, disposal and allowed residues limit

choices

– Temperatures outside -20˚ to +120˚C are a challenge

– Most chemistry is bimolecular – concentrated reactions

work better and save on many levels

– Chromatography is expensive - crystalline solids are

the workhorse of isolation and purification

– Controlling crystallization is essential

– Specialized equipment offer options to solve chemical

problems – flow reactors

Continuous Flow Rectors – The Concept

feed tanks

flow reactor

purification

analysis

pressure regulator

product tank

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Continuous Flow Reactors - Expanding

What is Possible

• Flow reactors permit smaller reaction vessels – unlimited

scalability

• Chemistry can be run 24hrs a day

• In line continuous analysis of conditions and product

• Safety is ensured by carefully controlled reactor cross

section and flow rates

• Fast and efficient mixing for rapid reactions

• Highly exothermic reactions become manageable

• Microwave heating, cooling, photolysis, increased

pressure are all possible

• Quality, reproducibility and safety are ensured

Case Study - Naproxcinod

• Collaboration between Nicox, DSM and Corning Glass

• Concern for exothermic breakdown of the product

• Key intermediate nitrated using 65% nitric acid

• Reaction flow continues into quench and neutralization

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Scaling by Parallel Processing

Multiplexed product delivery

= 14kg/hr

1mm reaction

channels

DSM produced 25 metric tons of API under

cGMP conditions!

Crystal Form – Polymorphism

“The ability of a solid material to exist in two or more

crystalline phases with different arrangements or

conformations in the crystal lattice.”

Polymorph Crystalline

Amorphous Non-crystalline

Pseudopolymorphs Hydrate/Solvate

Greek: “poly” = many

“morph” = forms

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α - glycine 𝜸 - glycine

Polymorphism

Same chemical structure

Molecules arranged differently in the unit cell

Different Physical & Chemical Properties

Effects physicochemical and pharmaceutical

properties of the API

Polymorphism

Packing: Density

Thermodynamic: Solubility

Free Energy

Melting Point

Spectroscopic: Vibrational Transitions

Kinetic: Reactivity

Dissolution

Stability

Mechanical: Hardness

Tensile Strength

Pharmaceutical: Flowability

Compatibility

Compressability

API & DP Manufacturing

&

Bioavailability

Quality

Safety

Efficacy

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Biopharmaceutics Classification

System (BCS)

0.1

1

10

100

1 10 100 1000 10000 100000

Volume Required to Dissolve the Highest Dose

(mL)

Perm

eab

ilit

y (

1x10

-6 c

m/s

) Class 1

High Solubility

High Permeability

High Solubility Low Solubility H

igh

Perm

eab

ility

Lo

w

Perm

eab

ility

Class 3

High Solubility

Low Permeability

Class 2

Low Solubility

High Permeability

Class 4

Low Solubility

Low Permeability

250

Case Study Effect of Polymorphism on

the Manufacturing

Process for the Drug Product

Lamivudine (3TC): GSK

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Drug Product Processing - Flow

Class: nRTI

Treatment: HIV 1&2

Hep B

Lamivudine (3TC) – “Pseudopolymorphs”

Note

Scale

Habit: Needles Crystallization Solv’t: Water

Melting Point: 135ºC Sol’y Stable Form: Water & MeOH

Solvate: 0.2 Hydrate

Crystal Class: Orthorhombic

Z: 20

3TC – Form 1

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Habit: bipyrimids Crystallization Solv’t: IMS & iso-PrOH

Melting Point: 178ºC Sol’y Stable Form: EtOH, n-PrOH,

Solvate: non-solvated iso-PrOH, n-BuOH

Crystal Class: tetragonal sec-BuOH, EtOAc

Z: 8 ACN, Acetone

Note

Scale

3TC – Form 2

Case Study Polymorphism Effect on

Bioavailability

Chloramphenicol Palmitate

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+ lipases

3 Polymorphs: A (stable)

B (metastable)

C (unstable)

Chloramphenicol Palmitate

Prodrug of chloramphenicol

Bioavailability of Polymorphic Forms

Comparison of mean blood serum levels of chloramphenicol after dosing

suspensions containing varying ratios of the A and B polymorphs of the

prodrug chloramphenicol palmitate (expressed as %B polymorph).

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Case Study

Polymorphism Effect on Solubility

Ritonavir: Abbott

Protease Inhibitor: HIV1&2

Marketed by Abbott: 1996

Ritonavir

• Not bioavailable from the solid state

• Solution and capsule formulations:

Soft-gel capsules: ritonavir in EtOH/water

• Single crystal form identified during development

• 240 lots of capsules manufactured

• No stability issues

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The Rest of the Story

• Mid-1998 batches of capsules failed dissolution

• Capsules analyzed by microscopy and XRD

– New polymorph – Form II

– Greatly reduced solubility

• Once seed crystals appeared - new polymorph everywhere

• Hydro-alcoholic capsule formulation:

– Not saturated with respect to Form 1

– 400% supersaturated with respect to Form II

• Formulation could no longer be manufactured

• Seriously threatened the supply of a life saving drug

Ritonavir Polymorphs

Form I Form II

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Case Study Insoluble and Permeability

Limited Absorption

Torcetrapib: Pfizer

Cholesteryl-ester transfer protein inhibtor (CETP-inhibitor)

Combination product: torcetripib & atorvastatin

"Second coming of Lipitor"

• Poorly solubility

• Highly liphophilic Log P ~7.5

• Absorption - highly variable

• Significant food effect

Torcetrapib

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• Development started in 1990

- Torcetrapib SDD:

torcetrapib: hydroxypropyl methylcellulose acetate-succinate

(1:3 w/w)

spray-dried from solution in acetone

stable amorphous spray-dried dispersion

- Torcetrapib SDD – CR:

torcetrapib SDD in an osmotic-pump controlled-release tablet

- Torcetrapib Drug Product:

torcetrapib SDD – CR coated with IR layer of atorvastatin

Torcetrapib/Atorvastatin Combination

Torcetripib Clinical Program

• Clinical trials started in 1999

• December, 2006 - Independent Data Safety Monitoring Board

﹣Recommended termination of a 15,000 patient Phase 3

clinical study

﹣ “Imbalance of mortality and cardiovascular events”

patients taking torcetripib/atorvastatin experienced excess

deaths compared to those taking Lipitor alone.

• Early in 2007 development stopped on the “Prized Asset”

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The Result:

One of Pharma’s Biggest Flops

GOOD: Developed a new area of formulation science:

“Spray-Dried Dispersions”

BAD: Took 9 years to get into the clinic with the SDD

formulation

BAD: Invested heavily - commercial manufacturing plant for

API and SDD in Ireland

BAD: Very late Phase 3 failure

BAD: Estimated spend to failure > $800 million

BAD: Two weeks after failure announced, 10,000 jobs cut

Case Study Time to Market:

Amorphous vs Crystalline API

Atorvastatin Calcium: Parke-Davis/Pfizer

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“For every day a drug is delayed coming to market,

a million dollars of revenue may be lost.”

“How many life-hours are lost for every day a drug

is delayed coming to market?”

Time to Market

? Thinking another way ?

Atorvastatin Calcium – Lipitor

• Initial Development:

– amorphous atorvastatin calcium Form B (later Form 23)

• No crystalline forms were known to exist

• Amorphous atorvastatin calcium

– intrinsically unstable

– can be stabilized through various additives to the formulation

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The Rest of the Story

• Crystallized: trihydrate form - during late stage clinical trials

• Tablets were reformulated using crystalline API

• Extensive bioequivalence testing conducted:

– Crystalline tablets – slower rate of absorption

– However, the extent of absorption was the same

• FDA reviewed the clinical data relating to the two forms

– Concluded that approval of the crystalline tablets was appropriate

Crystalline Amorphous

Today: at least 47 known polymorphs

various amorphous forms

1.5 Year Delay to Market

Lipitor Peak Yearly Sales (2006): $13.7 billion

Lost Revenue ~ $20.6 billion

or

~ $37.6 million/day

Number of life-hours lost:

? Indeterminate ?

The Moral of the Story

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Final Words

Quality

Safe Pure Effective

Every Time

Further Reading Flow Reactors

Chemica Oggi/Chemistry Today 2011, 29, (3), 47-49

Chemica Oggi/Chemistry Today 2012, 30, (4), 42-44

Chemica Oggi/Chemistry Today 2012, 30, (4), 51-54

Chemica Oggi/Chemistry Today 2009, 27, (1), 26-29

C&E News 2009, 87, (11), 17-19

C&E News 2014, 92, (21), 13-21

Organic Process Research and Development 2011, 15, 1477-1453

Organic Process Research and Development 2012, 16, 1069-1081

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Further Reading Crystalline & Amorphous Solids

• Jozwiakowski MJ, Nguyen, N-AT, Sisco JM, Spancake CW, “Solubility Behavior of

Lamivudine Crystal Forms in Recrystallization Solvents,” J. Pharm. Sci., 85 (2): 193-

199, 1996.

• Lin, S-Y, “An Overview of Famotidine Polymorphs: Solid-State Characteristics,

Thermodynamics, Polymorphic Transformation and Quality Control,” Pharm. Res.,

31 (7): 1619 -1631, 2014.

• Ku S, “Use of the Biopharmaceutical Classification System in Early Drug

Development,” AAPS J., 10 (1): 208-212, 2008.

• Butler JM, Dressman JB, “The Developability Classification System: Application of

Biopharmaceutics Concepts to Formulation Development,” J. Pharm. Sci, 99 (12):

4940-4954, 2010.

• Aguiar AJ, Krc J Jr, Kinkel AW, Samyn JC, “Effect of Polymorphism on the Absorption

of Chloramphenicol from Chloramphenicol Palmitate,” J. Pharm. Sci, 56 (7): 847-

853, 1967.

• Bauer J, Spanton S, Henry R, Quick J, Dziki W, Porter W, Morris J, “Ritonavir: An

Extraordinary Example of Conformational Polymorphism,” Pharm. Res., 18 (6): 859-

866, 2001.

• Friesen DT, et al., “Hydroxypropyl Methylcellulose Acetate Succinate-Based Spray-

Dried Dispersions: An Overview,” Mol. Pharm., 5 (6): 903-1444, 2008.

Contact [email protected] for a copy of today’s slides 58

The Role of Chemistry in Clinical Trials:

The Big Expense & Lessons Learned

Recordings will be available to ACS members after two weeks

www.acswebinars.org

Dr. John Morrison Senior Research Investigator,

Bristol-Myers Squibb

Dr. Graham Johnson President, NuPharmAdvise LLC

Dr. Jay Sisco Founder, JM Sisco Pharma Consulting LLC

Past-President, AAPS

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30

Upcoming ACS Webinars www.acs.org/acswebinars

59

®

Contact ACS Webinars ® at [email protected]

Thursday, August 7, 2014

“How to Write Abstracts that Capture

Your Audience”

Celia Elliott, University of Illinois at Urbana-Champaign

Patricia Blum, University of Illinois at Urbana-Champaign

Thursday, August 21, 2014

“Forecasting Chemistry: Predicting

Tomorrow’s Cutting Edge Science, Today”

Dr. Charles Twardy, SciCast Project Principal and Professor

at George Mason University

Contact [email protected] for a copy of today’s slides 60

The Role of Chemistry in Clinical Trials:

The Big Expense & Lessons Learned

Recordings will be available to ACS members after two weeks

www.acswebinars.org

Dr. John Morrison Senior Research Investigator,

Bristol-Myers Squibb

Dr. Graham Johnson President, NuPharmAdvise LLC

Dr. Jay Sisco Founder, JM Sisco Pharma Consulting LLC

Past President, AAPS

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Next in the Drug Discovery Series!

61

“Pharmacoeconomics and IP Strategies

in Drug Development”

Thursday, September 25, 2014

Be a featured fan on an upcoming webinar! Write to us @ [email protected] 62

How has ACS Webinars benefited you?

®

“I have learned a lot of what I am

interested in during the Drug Discovery

Series. For example, I have obtained the

new information about the drug discovery

process from both academics and

industries.”

Fan of the Week Zuping Xia, Ph.D. Research Associate Professor,

and Director of NMR Core,

College of Pharmacy, Washington State University

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63

facebook.com/acswebinars

@acswebinars

youtube.com/acswebinars

Benefits of ACS Membership

64 www.acs.org/2joinACS

Chemical & Engineering News (C&EN) The preeminent weekly news source.

NEW! Free Access to ACS Presentations on Demand® ACS Member only access to over 1,000 presentation recordings from recent ACS meetings and select events.

NEW! ACS Career Navigator Your source for leadership development, professional education, career services, and much more.

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ACS Webinars does not endorse any products or

services. The views expressed in this presentation

are those of the presenter and do not necessarily

reflect the views or policies of the American

Chemical Society.

65

®

Contact ACS Webinars ® at [email protected]

Upcoming ACS Webinars www.acs.org/acswebinars

66

®

Contact ACS Webinars ® at [email protected]

Thursday, August 7, 2014

“How to Write Abstracts that Capture

Your Audience”

Celia Elliott, University of Illinois at Urbana-Champaign

Patricia Blum, University of Illinois at Urbana-Champaign

Thursday, August 21, 2014

“Forecasting Chemistry: Predicting

Tomorrow’s Cutting Edge Science, Today”

Dr. Charles Twardy, SciCast Project Principal and Professor

at George Mason University