Eastman Chemical Co. v. BASF Aktiengesellschaft

47 F. App'x 566
CourtCourt of Appeals for the Federal Circuit
DecidedSeptember 17, 2002
DocketNo. 01-1101
StatusPublished
Cited by1 cases

This text of 47 F. App'x 566 (Eastman Chemical Co. v. BASF Aktiengesellschaft) 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
Eastman Chemical Co. v. BASF Aktiengesellschaft, 47 F. App'x 566 (Fed. Cir. 2002).

Opinion

GAJARSA, Circuit Judge.

This is an appeal from a decision by the United States District Court for the Eastern District of Tennessee granting the plaintiffs, Eastman Chemical Company (“Eastman”), Tomen Agro, Inc. (“Tomen”), and Valent U.S.A. Corporation (“Valent”) (collectively “plaintiffs”), summary judgment of noninfringement of U.S. Patent No. 5,118,856 (“the ’856 patent”) assigned to BASF Aktiengesellschaft and BASF Corporation (collectively “BASF”). Because the district court did not err in concluding that Eastman’s process could not infringe BASF’s patent as a matter of law, we affirm.

BACKGROUND

A The Patent Prosecution

BASF is the assignee of the ’856 patent, directed to a process for producing certain cyclohexanedione derivatives. The patent claims particular cyclohexanedione derivatives known as “triones.” Triones have the following chemical structure:

[[Image here]]

where “R” represents substituent groups.

The ’856 patent teaches a process of forming cyclohexanedione derivatives using five specific steps: a cyelization, a distillation, an acylation, a rearrangement, and a hydrolysis and decarboxylation. The patented process allows multiple reaction steps to be carried out in the same initial solvent, thereby eliminating isolations, purifications, and solvent swaps between steps. The ’856 patent has three claims. Claim 1 states in pertinent part:

1. In a process for the preparation of cyclohexanedione derivatives of the formula I
[[Image here]]
... by reaction of an alpha-beta unsaturated ketone with a dialkyl malonate in the presence of a solvent, which process includes the addition of a base, a decarboxylation step, a hydrolyzation step and an acylation step, the improvement com[568]*568prising: the reaction of an alpha,beta-unsaturated ketone of the formula II
with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcydohexenolone or its salt (III)
and acylation, hydrolysis and decarboxylation of (III), ... the process steps comprising
(a) reacting the alpha,beta-unsaturated ketone (II) in the presence of a base, with the dialkyl malonate in a solvent from which the alcohol liberated from the malonate can be distilled off,
(b) distilling to eliminate the alcohol,
(c) reacting the salt of the alkoxycarbonylcydohexenolone with a carboxylic acid halide having the structural formula RfCOHal, where R2 is alkyl of not more than 6 carbon atoms to form a product,
(d) treating the product of step (c), where appropriate, after removal of excess acyl halide, with an acylation catalyst, to form a further product, and
(e) hydrolyzing and decarboxylating the product of step (d) to form the compound of formula I.

’856 Patent, col. 7 I. 29 to col. 8 I. 29 (emphasis added). The differences between independent claims 1 and 2 are not relevant to this appeal. The only other claim in the patent, claim 3, depends from claim 2.

During prosecution, the patent was rejected multiple times before it ultimately issued. The first time the claims were rejected, they were rejected because, inter alia, the “salt of the intermediate of compound (III) is not defined in the claims or the specification.” (emphasis in original). In the same rejection, the examiner found the claims obvious in light of Sawaki et al., U.S. Patent No. 3,950,420 (“Sawaki”), which discloses the same basic process, and Murtha et al., U.S. Patent No. 4,115,-204 (“Murtha”), which discloses a process for isolating alcohol from its azeotrope by extractive distillation. In response the applicants attached the declaration of Dr. Richarz, one of the inventors, explaining that the applicant’s process is different from the prior art because unlike the application, the Sawaki prior art requires the intermediates to be isolated, which is a significant disadvantage. The applicants further argued that one skilled in the art would have no trouble practicing the invention based on the disclosure.

The application was again rejected because most of the earlier grounds for rejection had not been corrected, and the examiner did not find Dr. Richarz’s explanation sufficient to overcome the obviousness rejection. In response, the applicant amended the specification and claims. The claims were again rejected for many of the same reasons, including that the “salt of the intermediate compound (III) is not defined in the claims or the specification” and that the claims were unpatentable over Sawaki and Murtha. The applicant redrafted the claims and attached a declaration of co-inventor Dr. Reissenweber. The claims were again rejected as being unpatentable over Sawaki and Murtha. In response, applicants amended their claims and explained that “[i]n the third step of the process, the reaction product (III) from the first step, absent alcohol, [569]*569is reacted with an acid halide at a temperature of from 40-200°C, preferably 80-160°C to give a mixture of esters (Va and Vb).” (emphasis added). In addition, applicants filed a declaration from Dr. Kaczmarek, explaining that the reaction disclosed in the application results in a higher yield than the prior art and is simpler because there is no need to isolate an intermediate. In addition, Dr. Kaczmarek explained that Sawaki requires an additional base for the acylation step. As support for his conclusion that the process is distinctly superior to the prior art, his declaration includes the following statements:

2. The novel process is much simpler, because there is no need to isolate an intermediate. The process of Sawaki et al. requires an expensive isolating operation at the cyclohexanedione stage.
3. Sawaki et al. require an additional base (pyridine at the same time serving as solvent) for the acylation step, which means additional expense for the subsequent isolation of the product of value, since the pyridine has to be removed either by distillation or extraction.

The examiner rejected the claims again, asserting that the Kaczmarek declaration was not helpful because the claims are sufficiently broad in scope so as not to distinguish over the prior art. After further interactions, the Examiner, during an interview, recommended that the applicant put the claims in Jepson format. The interview summary states: “[t]he Examiner indicated that applicants file a continuing application, place the claims in Jepson form, and list the perceived differences of steps 2-4 of original claim one or steps (b), (e) and (d) of claim 2 as the improvement. If applicants follow this constructive suggestion of the undersigned examiner, he will allow the case on reconsideration.” At that point, the applicant canceled the old claims and submitted newly drafted claims in Jepson form. The examiner in a final rejection, rejected the new claims on the ground that inter alia, they were obvious in light of Sawaki. Applicants thereafter amended the claims again, in a way not relevant to this appeal, and they were allowed.

B. The Patent Litigation

Eastman filed a complaint for declaratory judgment alleging that it did not infringe the ’856 patent.

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Bluebook (online)
47 F. App'x 566, Counsel Stack Legal Research, https://law.counselstack.com/opinion/eastman-chemical-co-v-basf-aktiengesellschaft-cafc-2002.