In Re Rita S. Jones, Michael T. Chirchirillo and Johnny L. Burns

RICH, Circuit Judge.

Rita S. Jones et al. (collectively Jones) appeal from the April 15, 1991 decision of the Patent and Trademark Office (PTO) Board of Patent Appeals and Interferenсes (Board), Appeal No. 90-1920, sustaining the rejection of claim 1, the only claim of application Ser. No. 07/099,279, titled “The 2-(2'-Aminoethoxy)-Ethanol Salt of Dicam-ba,” as unpatеntable under 35 U.S.C. § 103. We conclude that the PTO has not presented a prima facie case of obviousness, and therefore reverse.

The Invention

The claimed invention is a novel salt of 2-methoxy-3,6-dichlorobenzoic acid, which acid is commonly referred to as “dicamba.” A known herbicide, dicamba has typically been sold in the form of its known dimethy-lamine salt.

The sole claim of the application on appeal reads:

1. The 2-(2'-aminoethoxy) ethanol salt of dicamba. The claimed sаlt has the following structure:

[[Image here]]

The Rejection

Claim 1 stands rejected as obvious in view of the combined teachings of the following references:

Richter U.S. Patent No. 8,013,054 Dec. 12, 1961

Moyle et al. U.S. Patent No. 3,056,669 Oct. 2, 1962

Balassa U.S. Patent No. 3,725,031 Apr. 3, 1973

Zorayan et al. 88 Chem. Abstracts No. 52300j 1978

Wideman 86 Chem. Abstracts No. 43711a 1977

Richter, which all agree is the closest priоr art, discloses dicamba in free acid, ester, and salt forms, for use as a herbicide. Among the salt forms disclosed are substituted ammonium salts, a genus which admittedly encompasses the claimed salt. Richter does not specifically disclose the claimed 2-{2'-aminoethoxy) ethanol salt, however. Most notably, Richter discloses (emphasis and bracketed word ours):

Compositions in which X is substituted ammonium are amine salts of 2-me-thoxy-3,6-dichlorobenzoic acid [dicamba] and are prepared by the addition of thе free acid to various amines. Typical amines which can be used to prepare such amine salts are dimethylamine, trimethylamine, triethylamine, diethanola-mine, triеthanolamine, isopropylamine, morpholine, and the like. The resulting products are, respectively, the dimethylamino, trimethylamino, triethy-lamino, diethanolamino, ‍​‌‌​‌‌​​‌‌​​‌​​‌‌​‌​​​​​​‌​‌​‌‌‌​‌‌‌‌‌​‌​​‌​​‌‌​‍triethanolam-ino, isopropylamino, and morpholino salts of 2-^methoxy-S, 6-dichlorobenzoic acid.

Zorayan teaches the amine (H2N(CH2CH20)2H) used to make the claimed salt, as well as the use of that amine in the preparation of surfactants for shampoos, bath preparations, and emulsifiers.

Wideman also teaches the amine disclosed in Zorayan.

The content of the remaining referenсes is unnecessary to our decision.

The Board upheld the examiner’s rejection of claim 1 as obvious, finding that the claimed 2-(2'-aminoethoxy) ethanol salt of dicamba and the diethanolamine salt of dicamba specifically disclosed by Richter were “closely related in structure,” and that based upon the expectation that “compounds similar in structure will have similar properties,” a prima facie case of obviousness had arisen. The Board found that Jones’ rebuttal evidence (Rule 132 declarations аnd data reported in the specification) failed to “compare the claimed subject matter with the closest prior art,” and accordingly did not serve to rеbut the prima facie case. This appeal followed.

Analysis

The Solicitor contends that the claimed salt falls within the genus of substituted amine salts of dicamba disclosed by Richter, and that, like Richter’s genus, the claimed compound has herbicidal activity. Thus, the Solicitor urges, under the circumstances of this case, (1) the genus/species relationship and (2) the common utility of the claimed and prior art сompounds support the Board’s holding of prima facie obviousness. Moreover, the Solicitor adds, although the claimed compound is neither a homolog nor a position isomer of those salts specifically disclosed in Richter, it is structurally similar thereto, particularly the diethanolamino salt noted by the Board.

The question of “structural similarity” in chemical patent ‍​‌‌​‌‌​​‌‌​​‌​​‌‌​‌​​​​​​‌​‌​‌‌‌​‌‌‌‌‌​‌​​‌​​‌‌​‍cases has generated a body of patent law unto itself. 1 Particular types or categories of structural similarity without more have, in past cases, given rise to prima facie obviousness; see, e.g., In re Dillon, 919 F.2d 688, 692-94, 16 USPQ2d 1897, 1900-02 (Fed.Cir.1990) (tri-orthoes-ters and tetra-orthoesters), cert. denied, — U.S. —, 111 S.Ct. 1682, 114 L.Ed.2d 77 (1991); In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoi-somers); In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977) (adjacent homologs and structural isomers); In re Hoch, 428 F.2d 1341, 166 USPQ 406 (CCPA 1970) (acid and ethyl ester). However, none of these types of structural similarity are involved here. And in any event, this court has previously stated that generalization is to be avoided insofar as specific structures are alleged to be prima facie obvious one from the other. In re Grabiak, 769 F.2d 729, 731, 226 USPQ 870, 872 (Fed.Cir.1985).

On the basis of the record before us, we cannot sustain the Board’s conclusion that the claimed salt and the diethanolamino salt disclosed by Richter are so “closely related in structure” as to render the former prima facie obvious in view of the latter. The claimed salt is a primary amine with an ether linkage. The diethanolamino salt disclosed by Richter is a secondary amine, without an ether linkage:

[[Image here]]

In addition, the оnly substituted ammonium salt of dicamba expressly disclosed by Richter having an ether linkage is the mor-pholino salt, which is cyclic in structure:

[[Image here]]

The claimed salt is, plainly, acyclic; i.e., linear. Lastly, while the isopropylamino salt disclosed ‍​‌‌​‌‌​​‌‌​​‌​​‌‌​‌​​​​​​‌​‌​‌‌‌​‌‌‌‌‌​‌​​‌​​‌‌​‍by Richter is a primary amine, as is the claimed salt, its iso- structure is quite different:

[[Image here]]

The lack of close similarity of structure is not negated by the fаct that the claimed salt is a member of Richter’s broadly disclosed genus of substituted ammonium salts of dicamba. The Solicitor contends that “[t]he relative size of the genus disclosed by the prior art would not appear to be a controlling factor in determining whether a prima facie case of obviousness exists for a species encompassеd within the described genus,” citing Merck & Co. v. Biocraft Labs., Inc., 874 F.2d 804, 806-09, 10 USPQ2d 1843, 1845-48 (Fed.Cir.), cert. denied, 493 U.S. 975, 110 S.Ct. 498, 107 L.Ed.2d 502 (1989). We decline to extract from Merck the rule that the Solicitor appears to suggest — that regardless of how broad, a disclosure of a chemical genus renders obvious any spеcies that happens to fall within it. In Merck, at issue on appeal was whether claims to a composition of two diuretics, amiloride and hydrochlo-rothiazide, presеnt in a particular “medically synergistic” weight ratio, would have been obvious in view of a specific prior art disclosure of amiloride in combination with hydrochlorothiazide, one of 1200 such combinations disclosed in the prior art reference. Id. at 806, 10 USPQ2d at 1845. Based on the facts before it, including evidence at trial that the experimentаtion needed to arrive at the claimed dosage was “nothing more than routine,” id. at 809, 10 USPQ2d at 1847, the court held that the claimed invention would have been obvious. In contrast, thоugh Richter discloses the potentially infinite genus of “substituted ammonium salts” of dicamba, and lists several such salts, the salt claimed here is not specifically disclosed. Nor, as wе have explained above, is the claimed salt sufficiently similar in structure to those specifically disclosed in Richter as to render it prima facie obvious. Every case, particulаrly those raising the issue of obviousness ‍​‌‌​‌‌​​‌‌​​‌​​‌‌​‌​​​​​​‌​‌​‌‌‌​‌‌‌‌‌​‌​​‌​​‌‌​‍under section 103, must necessarily be decided upon its own facts.

The Solicitor points out that, given the breadth of forms of dicamba (freе acid, ester, or salt) disclosed by Richter as having herbicidal utility, one of ordinary skill in the art would appreciate that the dicamba group has significance with respect to imparting herbicidal activity to dicamba compounds. Thus, the Solicitor contends, one skilled in the art would have been motivated to use, with dicamba, substituted ammonium sаlts made from a known amine, such as the amine disclosed by Zorayan and Wideman, and would have expected such a salt to have herbicidal activity. Before the PTO may combine the disclosures of two or more prior art references in order to establish prima facie obviousness, there must be some suggestion for doing so, found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art. In re Fine, 837 F.2d 1071, 1074, 5 USPQ2d 1596, 1598-99 (Fed.Cir.1988). We see no such suggestion in Zorayan, which is directed to shampoo additivеs, nor in Wideman, which teaches that the amine used to make the claimed compound is a byproduct of the production of morpholine. Nor does the broad disclosure of Richter fill the gap, for the reasons discussed above.

Conspicuously missing from this record is any evidence, other than the PTO’s speculation (if it be called evidence) that one of ordinary skill in the herbicidal art would have been motivated to make the modifications of the prior art salts necessary to arrive at the claimed 2-(2'-aminoethoxy) ethanol salt. See Grabiak, 769 F.2d at 731-32, 226 USPQ at 872 (“[I]n the casе before us there must be adequate support in the prior art for the [prior art] ester/[claimed] thioester change in structure, in order to complete the PTO’s prima facie cаse and shift the burden of going forward to the applicant.”); In re Lalu, 747 F.2d 703, 705, 223 USPQ 1257, 1258 (Fed.Cir.1984) (“The prior art must provide one of ordinary skill in the art the motivation ‍​‌‌​‌‌​​‌‌​​‌​​‌‌​‌​​​​​​‌​‌​‌‌‌​‌‌‌‌‌​‌​​‌​​‌‌​‍to make the proposed molecular modifications needed to arrive at the claimed compound.”)

Conclusion

We conclude that the PTO did not establish a prima facie case of obviousness, and thus did not shift to Jones the burden of coming forward with unexpected results or other objective evidence of non-obviousness. Accordingly, the decision of the Board is

REVERSED.

Notes

1

. See generally Helmuth A. Wegner, "Prima Fa-cie Obviousness of Chemical Compounds,” 6 Am.Pat.L.Assoc.Q.J. 271 (1978).

Case Details

Case Name: In Re Rita S. Jones, Michael T. Chirchirillo and Johnny L. Burns

Court Name: Court of Appeals for the Federal Circuit

Date Published: Feb 28, 1992

Citation: 958 F.2d 347

Docket Number: 91-1380

Court Abbreviation: Fed. Cir.