In Re Michael P. Doyle

293 F.3d 1355, 63 U.S.P.Q. 2d (BNA) 1161, 2002 U.S. App. LEXIS 11635
CourtCourt of Appeals for the Federal Circuit
DecidedJune 12, 2002
Docket01-1439 (Serial no. 08/601,101)
StatusPublished
Cited by9 cases

This text of 293 F.3d 1355 (In Re Michael P. Doyle) is published on Counsel Stack Legal Research, covering Court of Appeals for the Federal Circuit primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
In Re Michael P. Doyle, 293 F.3d 1355, 63 U.S.P.Q. 2d (BNA) 1161, 2002 U.S. App. LEXIS 11635 (Fed. Cir. 2002).

Opinion

CLEVENGER, Circuit Judge.

Michael P. Doyle appeals the decision of the Board of Patent Appeals and Interferences (“Board”) affirming the final rejection of claims 54 through 71 of his Reissue Application No, 08/601,101 based on the doctrine of In re Orita, 550 F.2d 1277, 193 U.S.P.Q. 145 (CCPA 1977). Ex parte Doyle, No.2000-0601, slip op. at 12 (December 29, 2000), request for reh’g denied (March 22, 2001). Because the Board erred in extending Orita to affirm the rejection of the pending claims, we reverse and remand.

I

The invention at issue in this case is a method of using chiral catalysts to catalyze enantioselectively particular classes of chemical reactions. Chiral compounds possess one or more chiral centers-centers that are asymmetric in all dimensions. Like a human hand, a chiral molecule cannot be superimposed on its mirror image, otherwise known as its enantiomer. Altering the relative orientation of the groups bonded to the various chiral centers of a molecule (i.e., creating a different stereoi-somer 1 of the compound) can have profound effects on the compound’s properties, especially with respect to how the compound interacts with other chiral molecules. These effects are important in pharmaceutical chemistry, among other areas of chemical endeavor, because often only one of the stereoisomers of a particular target compound possesses the desired pharmacological activity. Unfortunately, it is difficult to synthesize only one possible stereoisomer because most reactions produce what is known as a racemic mixture, which is an equal mixture of enan-tiomers. A category of reactions known as enantioselective reactions, however, will produce either (ideally) one enantiomer or (somewhat less ideally) a mixture that is enriched in a target enantiomer.

The inventor, Michael Doyle, developed a genus of chiral transition metal catalysts and a method of using them to perform enantioselective reactions with prochiral starting materials. 2 Dr. Doyle originally filed an application that, according to the examiner, attempted to claim nine different inventions, and included both composition of matter claims and method claims. The examiner imposed a nine-way restriction requirement. Dr. Doyle elected group VI, a group of method claims directed towards using the genus of catalysts to insert carbenes 3 into carbon-hydrogen, oxygen-hydrogen, nitrogen-hydrogen, and silicon-hydrogen bonds. He cancelled the other pending claims. The groups that he did not elect and that are relevant for purposes of this appeal include the following: (1) Group VII, drawn to a method of forming metal stabilized ylides using a chiral catalyst; (2) Group VIII, drawn to a method of adding a hydrogen atom using a chiral catalyst; and (3) Group IX, drawn to methods of adding silicon and hydrogen or boron and hydrogen using a chiral catalyst. The application eventually issued as U.S. Patent No. 5,296,595 on March 22, 1994. Dr. Doyle did not file any divisional applications directed towards the nonelect-ed groups during the pendency of the application that matured into the '595 patent.

*1357 On February 14, 1996, approximately one month before the running of the two-year clock for broadening reissues, see 35 U.S.C. § 251 (1994), Dr. Doyle filed a request for reissue of the '595 patent. He gave as his reason for requesting reissue that

[t]he 595 patent is partially defective because the claims are narrower than they should be in view of the 595 patent’s disclosure and the prior art. In particular, all 53 claims of the 595 patent are drawn to a method of enantioselec-tively inserting a carbene with a chiral catalyst. I now believe that the claims should have been broader in order to cover the use of the defined catalysts to enantioselectively catalyze reactions with a prochiral compound.

Thus, Dr. Doyle seeks to broaden his claims to cover the reaction of his catalysts with a genus of prochiral molecules, ie., not just insertion of a carbene. As Dr. Doyle concedes, the proposed reissue genus claims read on (but are broader than) the claims of nonelected Groups VII-IX.

All of the relevant claims at issue are new claims — not amendments to issued claims. Proposed claim 54 is illustrative of the reissue claims Dr. Doyle seeks:

A method of enantioselectively catalyzing a reaction comprising the steps of:
providing a prochiral compound, providing a chiral catalyst comprising a nucleus with a first and second atom of the same metal aligned on an axis, said metal selected from the group consisting of rhodium, ruthenium, chromium, molybdenum, tungsten, rhenium and osmium; and first, second, third and fourth bridging ligands oriented radially to the axis, each ligand having a first and second complexing atom, the first complexing atom of each of said bridging ligands being complexed with said first metal atom, and the second com-plexing atom of each of said bridging ligands being complexed to said second metal atom, said first bridging ligand further comprising a ring including said first complexing atom and attached to said second complexing atom, said ring also including a chiral center attached through a first bonding site to said first complexing atom, attached through a second bonding site to said ring, having a third bonding site occupied by a first substituent, and having a fourth bonding site occupied by a second substi-tuent, and said second bridging ligand further comprising a ring including said second complexing atom and attached to said first complexing atom, said ring also including a chiral center attached through a first bonding site to said second complexing atom, attached through a second bonding site to said ring, having a third bonding site occupied by a first substituent, and having a fourth bonding site occupied by a second sub-stituent, and wherein the R/S configuration of the chiral center on the second bridging ligand is the same as the R/S configuration of the chiral center on the first bridging ligand, and reacting said prochiral compound and said chiral catalyst under conditions sufficient [sic, to] cause the reaction.

The examiner allowed claims 1-53 of the reissue application, which were identical to the claims of the issued patent, but rejected new claims 54-71. Ex Parte Doyle, slip op. at 1. The examiner based his rejection on three grounds: (1) defective reissue declaration based on failure to specify an error correctable by reissue under the Ori-ta doctrine; (2) recapture; and (3) obviousness-type double patenting over claims 1-13 of U.S. Patent No. 5,175,311. Dr. Doyle appealed the first two grounds to the Board. 4 The Board agreed with Dr. *1358

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293 F.3d 1355, 63 U.S.P.Q. 2d (BNA) 1161, 2002 U.S. App. LEXIS 11635, Counsel Stack Legal Research, https://law.counselstack.com/opinion/in-re-michael-p-doyle-cafc-2002.