Allergan, Inc. v. Barr Laboratories, Inc. (Fed. Cir. 2013)

by McDonnell Boehnen Hulbert & Berghoff LLP
Contact

AllerganThose of you who dabble with chemical structures while prosecuting or litigating pharmaceutical patents may find Allergan v. Barr Laboratories, Inc., interesting.  In this ANDA litigation brought by Allergan against Barr, Teva, and Sandoz ("Barr"), the Federal Circuit opined on issues of claim construction and obviousness with respect to Allergan's Lumigan®, an ophthalmic solution used to treat high eye pressure in people with open-angle glaucoma or ocular hypertension.  The active ingredient in Lumigan® is bimatoprost (cyclopentane N-ethyl heptenamide-5-cis-2-(3a-hydroxy-5-phenyl-1-trans-pentenyl)-3, 5-dihydroxy, [1a,2ß,3a,5a]): FIG1(The ethyl amide moiety in the red square is where all the action was focused in the case.)  Allergan asserted claim 10 of U.S. Patent No. 5,688,819 ("the '819 patent"), which recited a method of treating ocular hypertension or glaucoma with a compound selected from a Marksuh group of five compounds listed by their chemical name.  Bimatoprost was one of them.

Claim Constructions

Barr had argued that bimatoprost did not fall within the scope of claim 5, from which claim 10 ultimately depended.  Claim 5 recited a method of treating ocular hypertension or glaucoma using a compound of formula FIG2where Z can be =O and X can be –N(R4)2, "wherein R4 is selected from the group consisting of hydrogen, a lower alkyl radical having from one to six carbon atoms . . . ."  The issue was framed as whether claim 5 encompassed compounds in which the two R4 moieties of "-N(R4)2" must be identical or could differ (as required by bimatoprost, where one R4 moiety must be hydrogen and the other C2-alkyl).  Both the District Court and the Federal Circuit held that claim 5 encompassed compounds in which the R4 moieties were non-identical.

Barr PharmaceuticalsBarr argued that the plain meaning of "-N(R4)2" required identical R4 moieties, relying on extrinsic evidence such as, for example, expert testimony that "[t]he (X)y nomenclature" was "commonly used" to represent identical substituents.  The Federal Circuit was unpersuaded, relying heavily on Phillips v. AWH Corp. for the proposition that claim terms are to be given the meaning as one of ordinary skill in the art would understand them in the context of how they are used in the patent at issue and concluding, "[t]he inventor's lexicography governs when the specification reveals a special definition given to a claim term by the patentee that differs from the meaning it would otherwise possess."

In arriving at the conclusion that "-N(R4)2" encompassed compounds in which the R4 moieties were non-identical, the Court pointed to the fact that of the five compounds recited in claim 10 (which, you'll remember, depended from claim 5), three (including bimatoprost) possessed an "-N(R4)2" moiety having non-identical R4 moieties.  The Court also noted that same relationship between claim 18 (which recited the same three compounds) and claim 11 (which recited a method of treating other diseases using compounds defined in the same manner as claim 5.  (It's of some interest to note that the specification used the exact same language at issue in the claims.)  And, finally, the Court noted that the specification disclosed the same three compounds as useful in the pharmaceutical compositions and methods of the invention.  The Court held that in this context the patent clearly manifested that "-N(R4)2" encompassed compounds with non-identical R4 moieties.

Practice tip:  Save yourself a lot of heartache and your client a lot of money, and in these situations define R4 more clearly, such as, "each R4 is independently selected from . . . ."

Obviousness

The Federal Circuit next considered the Barr's assertion that claim 10 (the method of treating glaucoma using one of bimatoprost or four other compounds) was obvious, first (a) dismissing the credibility of the defendants' expert, who was described as being "eviscerated" (ouch!) on cross examination and whose testimony was "flawed on a fundamental level" and (b) determining that the nature of the involved technology did not lend itself to lay interpretation, but required expert testimony.  This appears to have left Barr in the position of having to rely on the plaintiff's experts, an uncomfortable position, one imagines, at best.  As explained below, and not surprisingly, the defendants were unable to extract the support they needed to carry their burden of proving the claim obvious.

Barr asserted that bimatroprost was obvious over the isopropyl ester analog of compound 2 of Stjernschantz (WO 90/02253 [sic, WO 90/02553]), FIG3which was disclosed as useful for treating the very same conditions as bimatoprost.  The defendants argued that the plaintiff's expert testimony supported three facts necessary to establish obviousness:

(1)    Stjernschantz taught that bimatoprost-free acid lowered intraocular pressure;
(2)    Stjernschantz's compound 2 hydrolyzed into bimatoprost-free acid when placed in the eye; and
(3)    a skilled artisan would have known that substituting an amide for the ester at the C-1 position would result in a prodrug that hydrolyzed into bimatoprost-free acid in the eye.

In not so many words, the Federal Circuit held, "close, but no cigar," finding that although Allergan's expert testimony supported the first two points, the testimony in fact contradicted the third point.  Allergan's expert testified that an amide (such as found in bimatoprost) converts into a carboxylic acid at such a low rate ("500-year half life" of an amide in water) that one of ordinary skill in the art would not have considered it as a prodrug.  With Barr left empty-handed expert-wise, Allergan's expert opinion prevailed, and the Federal Circuit upheld the District Court's finding that claim 10 was not invalid as obvious.

Allergan, Inc. v. Barr Laboratories, Inc. (Fed. Cir. 2013)
Panel: Chief Judge Rader and Circuit Judges Bryson and Wallach
Opinion by Circuit Judge Wallach

 

DISCLAIMER: Because of the generality of this update, the information provided herein may not be applicable in all situations and should not be acted upon without specific legal advice based on particular situations.

© McDonnell Boehnen Hulbert & Berghoff LLP | Attorney Advertising

Written by:

McDonnell Boehnen Hulbert & Berghoff LLP
Contact
more
less

McDonnell Boehnen Hulbert & Berghoff LLP on:

Readers' Choice 2017
Reporters on Deadline

"My best business intelligence, in one easy email…"

Your first step to building a free, personalized, morning email brief covering pertinent authors and topics on JD Supra:
Sign up using*

Already signed up? Log in here

*By using the service, you signify your acceptance of JD Supra's Privacy Policy.
Custom Email Digest
Privacy Policy (Updated: October 8, 2015):
hide

JD Supra provides users with access to its legal industry publishing services (the "Service") through its website (the "Website") as well as through other sources. Our policies with regard to data collection and use of personal information of users of the Service, regardless of the manner in which users access the Service, and visitors to the Website are set forth in this statement ("Policy"). By using the Service, you signify your acceptance of this Policy.

Information Collection and Use by JD Supra

JD Supra collects users' names, companies, titles, e-mail address and industry. JD Supra also tracks the pages that users visit, logs IP addresses and aggregates non-personally identifiable user data and browser type. This data is gathered using cookies and other technologies.

The information and data collected is used to authenticate users and to send notifications relating to the Service, including email alerts to which users have subscribed; to manage the Service and Website, to improve the Service and to customize the user's experience. This information is also provided to the authors of the content to give them insight into their readership and help them to improve their content, so that it is most useful for our users.

JD Supra does not sell, rent or otherwise provide your details to third parties, other than to the authors of the content on JD Supra.

If you prefer not to enable cookies, you may change your browser settings to disable cookies; however, please note that rejecting cookies while visiting the Website may result in certain parts of the Website not operating correctly or as efficiently as if cookies were allowed.

Email Choice/Opt-out

Users who opt in to receive emails may choose to no longer receive e-mail updates and newsletters by selecting the "opt-out of future email" option in the email they receive from JD Supra or in their JD Supra account management screen.

Security

JD Supra takes reasonable precautions to insure that user information is kept private. We restrict access to user information to those individuals who reasonably need access to perform their job functions, such as our third party email service, customer service personnel and technical staff. However, please note that no method of transmitting or storing data is completely secure and we cannot guarantee the security of user information. Unauthorized entry or use, hardware or software failure, and other factors may compromise the security of user information at any time.

If you have reason to believe that your interaction with us is no longer secure, you must immediately notify us of the problem by contacting us at info@jdsupra.com. In the unlikely event that we believe that the security of your user information in our possession or control may have been compromised, we may seek to notify you of that development and, if so, will endeavor to do so as promptly as practicable under the circumstances.

Sharing and Disclosure of Information JD Supra Collects

Except as otherwise described in this privacy statement, JD Supra will not disclose personal information to any third party unless we believe that disclosure is necessary to: (1) comply with applicable laws; (2) respond to governmental inquiries or requests; (3) comply with valid legal process; (4) protect the rights, privacy, safety or property of JD Supra, users of the Service, Website visitors or the public; (5) permit us to pursue available remedies or limit the damages that we may sustain; and (6) enforce our Terms & Conditions of Use.

In the event there is a change in the corporate structure of JD Supra such as, but not limited to, merger, consolidation, sale, liquidation or transfer of substantial assets, JD Supra may, in its sole discretion, transfer, sell or assign information collected on and through the Service to one or more affiliated or unaffiliated third parties.

Links to Other Websites

This Website and the Service may contain links to other websites. The operator of such other websites may collect information about you, including through cookies or other technologies. If you are using the Service through the Website and link to another site, you will leave the Website and this Policy will not apply to your use of and activity on those other sites. We encourage you to read the legal notices posted on those sites, including their privacy policies. We shall have no responsibility or liability for your visitation to, and the data collection and use practices of, such other sites. This Policy applies solely to the information collected in connection with your use of this Website and does not apply to any practices conducted offline or in connection with any other websites.

Changes in Our Privacy Policy

We reserve the right to change this Policy at any time. Please refer to the date at the top of this page to determine when this Policy was last revised. Any changes to our privacy policy will become effective upon posting of the revised policy on the Website. By continuing to use the Service or Website following such changes, you will be deemed to have agreed to such changes. If you do not agree with the terms of this Policy, as it may be amended from time to time, in whole or part, please do not continue using the Service or the Website.

Contacting JD Supra

If you have any questions about this privacy statement, the practices of this site, your dealings with this Web site, or if you would like to change any of the information you have provided to us, please contact us at: info@jdsupra.com.

- hide
*With LinkedIn, you don't need to create a separate login to manage your free JD Supra account, and we can make suggestions based on your needs and interests. We will not post anything on LinkedIn in your name. Or, sign up using your email address.