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“Discovering Vismodegib in the Fight Against Skin Cancer” Session 7 of the 2017 Industry Science Series

Dan Sutherlin Principal Scientist and Director,

Discovery Chemistry, Genentech

Mark Jones Executive External Strategy and

Communications Fellow, Dow Chemical

8/2/2017

8

Discovering Vismodegib in the Fight Against

Skin Cancer: The First Approved Inhibitor of the Hedgehog Pathway

Dan Sutherlin, PhD

Department of Discovery Chemistry

Genentech

15

Outline

• Introduction to the Hedgehog (Hh) pathway and the

biological detective story leading to it’s identification as a

drug target

• Discovery of Vismodegib (Erivedge) and its properties

• Overview of the Clinical Results

• Final thoughts on the pathway as a drug target

16

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Inactive Receptor Ligand-dependent Activation

Hedgehog Pathway Intro: Signaling Through

PATCHED (PTCH) and SMOOTHENED (SMO)

PTCH SMO

No Signal

-

OFF

Signal

Gli2,3

Hh

Gli1

DNA

Growth

Differentiation

Survival

17

Audience Challenge Question ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT

• From the number of lysine amino acids on the protein giving it a “spiky” appearance

• Because the Hh protein burrows into the protein patched like the animal burrows into the ground

• From the way a fly embryo looked in a genetic screen

• Because cells “roll-up” into a ball like shape resembling a hedgehog when treated with the protein

The Hedgehog protein got it’s name…

18

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fly mouse

The hedgehog pathway regulates proliferation

and differentiation during development

• Developmental defects result from pathway inactiviation

• Mainly quiescent in adult - roles in tissue maintenance and repair

Nusslein-Volhard & Weischaus, Nature, 1980 Hui and Angers, Annu Rev Cell Dev Biol, 2011

Polydactyly

19

Inappropriate regulation associated with

developmental disorders in humans

Polydactyly - PHS

Holoprosencephaly

(SHH)

• Loss of signaling in

utero leads to cyclopia in

offspring.

Pallister-Hall

Syndrome (GLI3)

• Polydactyly

• Hypothalamic

Harmatomas

Gorlin Syndrome (PTCH1)

Basal Cell Nevus Syndrome

reduced pathway activity

in fetal development

increased pathway

activity in the adult

20

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Activating pathway mutations are implicated in

most BCCs and up to a third of medulloblastomas

Mutations in the Hedgehog (Hh) pathway

drive unregulated growth in BCC

BCC – Basal Cell Carcinoma (the most

common form of skin cancer)

•Incidence of over a million cases in the US

every year (wear sunscreen and a hat!)

•Most are removed by surgery

•The unmet need: progression to unresectable

locally advanced or metastatic tumors (small

percentage of BCCs)

90% 10%

21

Cyclopamine causes similar birth defects in sheep

• Sheep grazing in mountain ranges of central Idaho

produced offspring with cyclopia

• Birth defect traced to a specific plant – the corn lily,

Veratrum Californicum

• Natural product cyclopamine produced in the corn

lily was found to be the cause

• Appears to have no effect on adult sheep

cyclopamine

22

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Inactive Receptor Ligand-dependent Activation

Cyclopamine identified as a inhibitor of the Hh

signaling pathway – binds to SMO

PTCH SMO

No Signal

Hh Hh

No Signal

X

Cyclopamine

Signal

Gli2,3 Cyclopamine

• small molecules can inhibit the pathway

• not a very good starting point for a drug discovery effort based on poor

solubility, pharmacokinetics (PK), synthetically challenging

Cooper, M. K., Porter, J. A., Young, K. E. & Beachy, P. A. (1998) Science 23

If Cyclopamine is not suitable what

are we looking for in a drug?

Compounds need to be…

•Potent (low dose)

•Selective the target (safe – minimize side effects)

•Metabolically stable (dosing schedule)

•Orally available (convenient)

•Soluble (suitable for dosing strategy)

•Eventually scalable to multi-kilograms

24

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Phase I in BCC

Orally available Hh antagonists

JACS 2008

Curis/Evotec

• HTS with a 79,000 compound library

• Cell based assay using Gli-Luciferase reporter (S12 mouse)

• Follow up with human cell based assay (HEPM human)

Curis Systemic Hedgehog Antagonist Program

topical Hh

antagonist

Lead Discovery Lead Discovery

and Optimization

S12 = 12 nM

HEPM = 3 nM

Proof of Concept Molecules developed prior to Genentech Collaboration:*

CUR-2

Under the Genentech-Curis collaboration agreement, Curis provided broad intellectual property rights

relating to the Hedgehog pathway, including several classes of proprietary small molecule inhibitors.

*

Luciferase gene

Luciferase

Demonstrated Efficacy in a

Medulloblastoma Allograft Efficacy Model

-fresh suspension made daily

(mg/kg QID) Dose response w/ Curis leads

0 1 2 3 4 5 6 7 8 9 10 11 12 13 50

75

100

125

150

175

200

225

250

275

300 CUR-0199691 100

CUR-0200929 100

CUR-0199691 25

CUR-0200929 25

Vehicle

Days

% T

um

or

Gro

wth

CUR-1 100

CUR-1 25

CUR-2 100

CUR-2 25

CUR-1

CUR-2

Passage in vivo Ptch (+/-)

26 Tumors regress at maximum efficacious dose

8/2/2017

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A Lead but not a drug: concerns with

metabolic stability and solubility

Species Microsomal

CLhep

ml/min/kg

Measured

CLp ml/min/kg

Mouse 2 16

Rat 17 3

Dog 22 145

Cyno 41 25

Human 9 ???

Potency HEPM 3 nM

S12 12 nM

Solubility (pH 6.5) 0.3 ug/ml CUR-2

Color code

T1/2 = V * 0.693

Cl

Clearance =

(Cl)

dose

AUC

Some PK parameters

In vitro In vivo

27

Medicinal Chemistry Program Goals

1. Improve predicted PK in human measured by…

• in vitro (predicted) and in vivo (actual) stability in higher species

• in vitro stability in human

2. Increase Solubility measured by…

• Thermodynamic solubility at pH 6.5 (crystalline material)

• Oral PK as a solution and suspension

Chemistry Plans:

A. Explore SAR of the the heterocycle

(benzimidazole)

B. Then focus on the amide

A.

B.

28

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General Synthetic Scheme

Benzimidazoles

Imidazoles

Amides

benzothiazoles

Qunoxalines

Pyridazines

Indolizines

Imidazolethiazoles

Pyrazines

Indazoles

Pyrazoles

Pyridines

Pyrimidines

Pyrazolopyridine

29

Summary of A ring SAR (Structure Activity Relationship)

1 (CUR-

2)

30

8/2/2017

16

✔

✗

H-bond acceptor

H-bond donor

H-bond acceptor is important for potency

1 (CUR-

2)

31

H-bond acceptor preferred in the

2-position of the heterocycle

1 (CUR-

2)

32

8/2/2017

17

2-pyridiyl biphenyl docked into a public

structure of SMO helps to explain SAR

2-pyridyl biphenyl

docked into the

Smoothened structure

Trp

Tyr

Arg

33

New Heterocycles have Improved

Stability Relative to Benzimidazole

R group

Gli S12

IC50

(mouse)

Predicted Microsomal

Clearance mL/min/kg

Measured Cl

mL/min/kg

rat dog human rat dog

12 nM 19 22 9 3 120

80 nM 32 17 8 99 -

52 nM 9 16 7 11 7

42 nM 6 10 1 5 2

34

8/2/2017

18

Pyridine has Improved Stability and Solubility

Relative to Benzimidazole and Quinoxaline

R group

Gli S12

IC50

(mouse)

Predicted Microsomal

Clearance mL/min/kg

Measured Cl

mL/min/kg

Solubility

ug/mL

rat dog human rat dog pH 1 pH 6.5

12 nM 19 22 9 3 120 300 0.3

80 nM 32 17 8 99 - - -

52 nM 9 16 7 11 7 0.1 0.1

42 nM 6 10 1 5 2 1000 2

35

SAR Summary for C Ring Aryls

Cl

NH

O

R

N

36

8/2/2017

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Cl

NH

O

R

N

S(12) = 20 nM

HEPM = 3 nM

Further Improvement in

Potency Following SAR Trends

37

In Vivo Clearance Predicted Well by Microsomes

Suggests Low Clearance in Humans

Species Predicted

Clearance

Measured

Clearance Vss

Rat 2 5 0.5

Cyno 26 19 1.0

Dog 0.7 0.3 1.0

Human 4.6 predict low

38

8/2/2017

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What about solubility?

Addition of chlorine increases cLogP

Improved solubility at both pH’s

S(12) = 20 nM

HEPM = 3 nM R cLogP

H 3.3

Cl 3.9

39

Audience Challenge Question ANSWER THE QUESTION ON BLUE SCREEN IN ONE MOMENT

• a decrease in solubility

• an increase in solubility

• other properties but solubility is not one of them

Increasing LogP is expected to correlate with…

40

8/2/2017

21

Orthochloro - Improves Solubility

Despite Higher cLogP


S(12) = 20 nM

HEPM = 3 nM

41

R cLogP Solubility ug/mL

pH 1 pH 6.5

H 3.3 420 0.5

Cl 3.9 >3800 ~25

cLogP vs. solubility

Hill and Young, Drug Discovery

Today 2010, Vol 15, p. 648

41

Orthochloro - Improves Solubility

Despite Higher cLogP


S(12) = 20 nM

HEPM = 3 nM

H Cl

42

R cLogP Solubility ug/mL

pH 1 pH 6.5

H 3.3 420 0.5

Cl 3.9 >3800 ~25

8/2/2017

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High Exposure Contributes to Good PD Response

% G

li S

up

pre

ss

ion

(SD

) vs

. C

on

tro

l

0

20

40

60

80

100

0.86 0.21 uM 14 6.6 uM 23 7.9 uM Plasma Conc.

Calu-6 tumor PK/PD

• 200-400 mm3

• bid, 2.5 days, 75 mg/kg

• sample plasma 4 hrs.

• harvest tumor 6 hrs.

Vismodegib

Gli

expression

43

Solubility Affects Oral Bioavailability

When Dosed as a Suspension in Dog

G-025638 Dog PK - Average (N=3)

0.001

0.01

0.1

1

10

100

0 120 240 360 480 600 720 840 960 1080 1200 1320 1440

Time (min)

Plas

ma C

on

c. (

uM

)

Average- G-025638 Dog IV 1 mg/kg (N=3)

Average- G-025638 Dog PO 2 mg/kg Soln (N=3)

Average- G-025638 Dog PO 2 mg/kg Susp (N=3)

G-025897 Dog IV 1mg/kg and PO 2 mg/kg (Soln and Susp)

0.001

0.01

0.1

1

10

100

0 120 240 360 480 600 720 840 960 1080 1200 1320 1440

Time (min)

Pla

sm

a C

on

c (

uM

)

G-025897 IV 1 mg/kg Dog TKRG-025897 IV 1 mg/kg Dog CXVG-025897 IV 1 mg/kg Dog IGTG-025897 PO 2 mg/kg Soln Dog TKRG-025897 PO 2 mg/kg Soln Dog CXVG-025897 PO 2 mg/kg Soln Dog IGTG-025897 PO 2 mg/kg Susp Dog TKRG-025897 PO 2 mg/kg Susp Dog CXVG-025897 PO 2 mg/kg Susp Dog IGT

PO 2mg/kg solution

PO 2mg/kg suspension

PO solution and suspension

curves are equivalent to IV

GDC-0449

Vismodegib

IV dose

44

8/2/2017

23

Vismodegib is Efficacious in

Medulloblastoma Allograft Model

0

500

1000

1500

2000

2500

3000

3500

0 1 2 3 4 5 6 7 8

time (days)

tum

or

vo

lum

e (

mm

3)

Vehicle (MCT)

50

25

12.5

6.25

BID

45

Favorable In Vitro ADME Properties

Metabolic Stability

Hepatocytes

Cl projected (ml/min/kg)

Human – 4.6 (S)

Mouse – 3.3 (S)

Cyno – 26 (L)

Dog – 0.73 (S)

Rat – 1.8 (S)

CYP IC50 (µM)

1A2 36.5

2C8 24.1

2C9 29.3

2C19 26.7

2D6 42.9

3A4 >50.0

Plasma Protein Binding

Mouse 91%

Rat 97%

Cyno 98%

Dog 95%

Human 97%

Permeability (Caco)

Papp A to B (cm/s) = 39.5 E-06

Papp B to A (cm/s) = 39.1 E-06

(B to A)/(A to B) ratio = 0.99

MW = 412 g/mol

cLogP = 3.0

Potency

IC50 (HEPM) = 3 nM

IC50 (S12) = 20 nM

GDC-0449

(Vismodegib)

46

8/2/2017

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Medchem Synthesis of Vismodegib

Robarge, K. D.; et al. Bioorg. Med. Chem. Lett. 2009, 19, 5576. 47

Primary Objectives

• Evaluate the safety, tolerability, pharmacokinetics (PK),

pharmacodynamics (PD), and maximum tolerated dose (MTD) of GDC-0449

administered orally on a continuous once-daily schedule in patients with

advanced solid malignancies

• Determine the recommended Phase II dose and schedule of GDC-0449

Secondary Objective

• Make a preliminary assessment of tumor response

Vismodegib Phase I Trial

GDC-0449 is being developed under collaboration agreements between Genentech, Curis, and Roche. 48

8/2/2017

25

Mean ± SD Concentration - Time Profiles

After a Single Dose of GDC-0449

Day of Study T i m e ( D a y )

0 1 2 3 4 5 6 7

0

2

4

6

8

1 0

1 5 0 m g ( N = 7 ) 2 7 0 m g ( N = 9 ) 5 4 0 m g ( N = 4 )

Vis

modegib

Tota

l P

lasm

a

Concentr

ation (

uM

)

49

50

Median Concentration: Time Profiles of Stage 1 Patients (multi-dose)

Stage 1- Median Plot

Time (Day)

0 7 14 21 28 35 42 49 56 63

GD

C-0

44

9 C

once

ntra

tion

(µM

)

0

10

20

30

40

50

60

150 mg (N=7)

270 mg (N=9)

540 mg (N=4)

(Error bars represent 25th and 75th percentiles)

Vis

modegib

Concentr

atio

n (

μM

)

50

8/2/2017

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51

Vismodegib Adverse Events from Phase I

As reported by 01 April 2008

• No dose-limiting toxicities were observed with Vismodegib

• The most frequently observed AEs (regardless of relationship to drug):

Fatigue, dysgeusia (altered taste), nausea, anorexia, cough, abdominal pain, diarrhea, hyponatremia, decreased weight, back pain, and decreased appetite

• Grade 3 drug-related AEs consisted of reversible

Fatigue (n=2)

Asymptomatic hyponatremia (n=1)

Rudin et al., EORTC-NCI-AACR 2008

Data cutoff 6/1/08 51

52

49 year old with Multiple Large,

Invasive Lesions of Skin

Baseline After 3 months

52

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27

Vismodegib in locally advanced BCC

Week 24 Baseline

Week 24: no residual BCC on biopsy

53

54

67 year old with BCC Metastatic to Lung, Liver, and Bone

Baseline At 8 months (confirmed PR)

54

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55

Pivotal Phase 2 Study of Metastatic and Locally Advanced BCC Patients

Locally Advanced BCC Metastatic BCC

mBCC (n=33) laBCC (n=63)

ORR by Indep Rev 30.3% 42.3%

ORR by Investigator 45.5% 60.3%

PFS by Investigator 9.2 m 11.3 m

Sekulic et al. NEJM. 2012 55

• Investigator-initiated, randomized, placebo controlled trial

• 41 patients with Basal cell nevus syndrome randomized 2:1 (active:placebo)

• Vismodegib at 150mg per day for 18 months

Month 9

Baseline

-300

-200

-100

0

100

200

300

GDC-0449 Placebo

BC

C d

iam

ete

r (m

m)

P<0.001

Reduction in Existing BCC size

GDC-0449 Placebo0

5

10

15

20

25

30

P<0.001

Num

ber

of new

BC

Cs

GDC-0449 prevents BCCs

E. Epstein, J. Tang et al. NEJM 2012

Vismodegib efficacy in Gorlin patients

56

8/2/2017

29

GDC-0449-A potent inhibitor of the

hedgehog pathway

Robarge, K. D.; et al.

Bioorg. Med. Chem. Lett. 2009, 19, 5576.

Discovery and preclinical development

of vismodegib

Gould, S.E.; et al.

Expert Opin. Drug Discov. 2014, 9, 969.

16 Patient

Signatures

Additional References:

57

What makes the Hh pathways such a great drug target?

• Genetic link to disease – translation

• Inhibition in models results in tumor regression - efficacy

• Major role in development, less active in the adult – safety

• SMO drug target is GPCR like – drugability

• …with few homologs – safety / selectivity

• Defects in pathway accounts for most BCCs – patient

selection

And for the drug discovery of vismodegib?

• Robust and relevant models (meduloblastoma allograft)

• Potent, drug-like starting point with a modular synthetic

scheme allowed the team to focus on ADME properties

• Combination of favorable PK and safety profile ensures

maximum coverage of target throughout dosing

58

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30

Acknowledgements – it takes a village / small town

Chemistry (Genentech)

Jim Marsters

Kirk Robarge

Vickie Tsui

Janet Gunzner

Mike Koehler

Mark Stanley

Shumei Wang

Georgette Castanedo

Rich Goldsmith

Kim Malesky

Kevin Lau

Liang Bao

Michael Dina

Rebecca La Londe

Chemistry (Evotec)

Shirley Brunton

Andy Boyd

Colin Mackinnon

Assays, PK and

Informatics (Curis)

Chang Qian

Oivin Guicherit

Alysia Parkes

Biology (Genentech)

Fred de Sauvage

Stephen Gould

Tracy Tang

Hua Tian

Suzie Scales

Derek Marshall

Lesley Murray

Leslie Lee

Michelle Nannini

Beth Blackwood

Biology (Curis)

Lee Rubin

Karen Kotkow

Christian Dibble

Melissa Chenard

Guizhi Yang

Assays (Genentech)

Dave Peterson

Christine Chang

Susan Keating

Brooke Hashimoto

James Ernst

Chemistry Process Dev (Genentech)

Mark Reynolds

Scott Savage

Shrinivasan Babu

Remy Angelaud

PK/Metab (Genentech)

Cyrus Khojasteh

Harvey Wong

Bilin Chou

Jason Halladay

Laurent Salphati

Young Shin

Hank La

Susan Wong

Savita Ubhayaker

Emile Plise

Sharmin Merchant

Mike Reich

Formulations (Genentech)

Minli Xie

Zedong Dong

Yong Cui

Toxicology (Genentech)

Hong Wang

Kelly Flagella

Eric Morinello

Clinical PK (Genentech)

Sravanthi Cheeti

Rick Graham

Laurent Vernillet

Bert Lum

Diagnostics (Genentech)

Bob Yauch

Ling Fu

Chris Callahan

Walter Darbonne

Ward Kadel

Kelly DuPree

Thomas Holcomb

Regulatory (Genentech)

Bao Truong

Miki Yamamoto

Project Management (Genentech)

Amel Lamrad

Emily Leong

59

Acknowledgements

Special thanks to all our patients and their families.

Translational Genomics Research Institute (TGen) and Scottsdale Healthcare

Daniel Von Hoff, Steve Anthony, Lisa Blaydorn, Mitesh Borad, Molly Downhour, Gayle Jameson,

Ronald Korn, Katy Schroeder, Raoul Tibes, Glenn Weiss, Erica White

Johns Hopkins University

Charles Rudin, Barbara Coleman, Christine Hann, Rosalyn Juergens, Heather Schneitzinger

Karmanos Cancer Institute, Wayne State University

Patricia LoRusso, Elisabeth Heath, Lisa Malburg, MaryJo Pilat, Carolyn Shearer, Andrea

Smoots, Denise Weiss, Jie Zhang

Genentech BioOncology

Jennifer Low, Josina Reddy, Lisa Nelson, Howard Mackey, Amita Joshi, Kenn Zerivitz, Jorge

DiMartino, Brandon Arnieri, Joanne Benedict, Alexandra Carrillo, Ilsung Chang, Susan Eng,

Rachael Garlick, Chris Hendricks, Sho-Rong Lee, Harald Loeffler, Hilary Nelson, Dale Posner,

Danny Shih, Dana Shriver, Tamar Steinmann, Annabel Vaghar, Janice Warner

60

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61








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What is the Heroes of Chemistry Award?

Heroes of Chemistry is an annual award sponsored by the American Chemical Society that recognizes talented industrial chemical scientists whose work has led to the development of successful commercialized products ingrained with chemistry for the benefit of humankind.

Email [email protected] or Visit www.acs.org/heroes

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

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youtube.com/acswebinars


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Benefits of ACS Membership


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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Documents

Discovering Vismodegib in the Fight Against Skin Cancer: … · senior undergraduates and graduate students through a national competition. Awardees receive three years of funding