CHAU BUIUC BERKELEY

NOVEMBER 3, 2008IEOR 190G

Sanofi-Aventis vs. ApotexPlavix® Patent Case

Plavix® Patent CaseOutline

1. Introduction2. Plavix® Patent3. Patent litigations4. Court decision5. Opinion6. Questions

1. Introduction

Plavix® a prescription medication for heart attacks, stroke,

peripheral vascular disease the second highest selling pharmaceutical the largest market share In 2005, $5.9 billion was sold

Cloridrogel Active ingredient for Plavix The dextro-rotatory enatiomer of methyl alpha

tetrahydro thiano pyradyl chlorophenyl acetate (MATTPCA)

The enantiomer is bisulfate salt The patent of producing cloridrogel is held by Bristol in

the US, and Sanofi-Aventis in the other countries Sanofi-Aventis

A multinational pharmaceutical company The fourth largest pharmaceutical company Research, develop, manufacture and market

pharmaceutical products , including Plavix® Apotex

Founded in 1974 The largest producer of generic drugs in Canada Produces over 300 generic pharmaceuticals Market generic clopidogrel in 2006

2. Plavix® Patent

2. Plavix® Patent (cont’)

2. Plavix® Patent (cont’)

What are enantiomers?Enantiomers are molecules that have the same

molecular formula and sequence of bonded atom, but different spatial arrangements.

Enantiomers are capable of rotating plane-polarized light. Dextro-rotatory enantiomers rotate polarized light to

the right. Levo-rotatory enantiomers rotate polarized light to the

left

Racemate is mixture of equal amount of dextro and levo enanatiomers, exhibiting no optical activity.

2. Plavix® Patent (cont’)

Process of preparation of dextro-rotatory enantiomer from the

racemate

Racemate Solution salt Crystalline Salt

acetone Recrystallisation

acetone Alkaline With

AqueousNaHCO3

Dextro-rotatory

enatiomer

PrecipitateHydrogen SulfateOf

Dextro-rotatoryenantiomer

3. Patent litigation

Timeline Racemate of was first identified prior US patent was filed in 1983 Dextro-rotatory enantiomer of was carried forward US patent was filed in 1988 In 2006, generic cloridogrel was marketed by Apotex In 2006, Bristol-Myers Squibb filed a suit to Apotex for

patent infrigement.

3. Patent litigation (cont’)

Apotex’s position Anticipation

The bisulfate salt was invalid over the previous patent. The patent ‘596 disclosed the method of producing

MATTPC where bisulfate salt was stated as preference. F.3d at 1376.

Obviousness A person of ordinary skill in the art is able to separate

dextro-rotatory MATTPC based on the patent ‘596. 470 F.3d at 1378.

3. Patent litigation (cont’)

Sanofi’s claims Influence of levo-rotatory enantiomer Influence of bisulfate of enantiomer

There are over 50 salts to choose from Experiment is needed to determine the suitable salt

Influence of salt form crystalline form

The difference in solubility of enantiomer

4. Court decision

In 2006, Federal Circuit affirmed Apotex’s generic clopidogrel bisulfate product infringes the ‘265 patent

In 2007, generic cloridogrel was halted in retail pharmaceuticals in the U.S.

In 2008, Sanofi wins protection for Plavix patent in Canada.

5. Opinion

“Intellectual property rights are essential for

the research-based pharmaceutical and

biotech industry to continue to develop

innovative medicines to treat serious

diseases.”

6. Questions ??

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Bibliography

US patent 4,847,265US patent 4,529,596http://www.fr.com/news/2007/July/

Sanofivapotex.pdfhttp://patentdocs.typepad.com/patent_docs/

2006/12/sanofisynthelab.htmlhttp://www.google.com/patents?

id=Vbk4AAAAEBAJ&dq=4,847,265http://www.google.com/patents?

id=zeA7AAAAEBAJhttp://www.pubs.acs.org/cen/news/84/i37/8437plavix.html