Fields v. Conover

Citation443 F.2d 1386,170 USPQ 276
Decision Date01 July 1971
Docket NumberPatent Appeal No. 8516.
PartiesThomas Lynn FIELDS, et al., Appellants, v. Lloyd H. CONOVER and Robert B. Woodward, Appellees.
CourtUnited States Court of Customs and Patent Appeals

Edward A. Conroy, Jr., Stamford, Conn., attorney of record, for appellants. Harry H. Kline, Stamford, Conn., of counsel.

Nicholas E. Oglesby, Jr., Wilmington, Del. (Connolly & Hutz), Wilmington, Del., attorneys of record, for appellees.

Before RICH, ALMOND, BALDWIN, LANE, Associate Judges, and LANDIS, Judge, United States Customs Court, sitting by designation.

RICH, Judge.

This appeal is from the decision of the Board of Patent Interferences awarding priority to Conover and Woodward (hereinafter Conover), the senior party. Fields, Wilkinson and Kende (hereinafter Fields) appeal solely on the ground that Conover's application, serial No. 209,269, filed July 11, 1962, does not support the counts, which were copied from Fields' patent No. 3,167,579, issued January 26, 1965, on an application filed October 22, 1962. Neither party took testimony. We reverse.

THE INVENTION

The subject matter of this interference is substituted 4, 10-dioxo-5-hydroxy-1, 2, 3, 4, 4a, 9, 9a, 10-octahydroanthracenes. Count 1 is as follows subparagraphing and numbering of the relevant carbon atoms supplied):

A compound selected from the group consisting of those of the formula
wherein
X is selected from the group consisting of hydrogen, chlorine and bromine,
R is selected from the group consisting of hydrogen, carboxy, lower carbalkoxy and phenyl lower carbalkoxy,
R1 is selected from the group consisting of hydrogen and methyl,
R2 is selected from the group consisting of hydrogen, methyl and formyl,
Z is selected from the group consisting of cyano, carboxy, and lower carbalkoxy and
Y is selected from the group consisting of hydrogen and cyano.

Count 2 is for 8-chloro-1, 2, 3, 4, 4a, 9, 9a, 10-octahydro-4, 10-dioxo-5-hydroxy-2-anthraceneglycine, a species encompassed within the genus of count 1 which may be represented by the following structural formula:

Appellant Fields' patent discloses that "The novel compounds of the present invention are particularly useful as chelating, complexing or sequestering agents for polyvalent metallic ions," that they are also "biologically active and have been found to possess antibacterial activity," and that they "may also be useful in the synthesis of physiologically active antibiotics of the tetracycline series." Fields' patent is assigned to American Cyanamid Co., while Conover's application seems to be assigned to Chas. Pfizer & Co., Inc.

Conover relies on an enormous application having 196 typed pages of specification which in the words of its introductory paragraph,

* * * relates to a process of preparation of antibacterial agents. More particularly, it is concerned with the discovery of new and novel sic synthetic routes for the preparation of known as well as new tetracycline products. It is also concerned with the new and useful tetracycline products obtained thereby, as well as with the new intermediates of the process.

The Conover process starts with known 3, 4, 10-trioxo-1, 2, 3, 4, 4a, 9, 9a, 10-octahydroanthracenes and converts them to tetracyclines by means of a multi-step reaction sequence in which several alternative routes exist for the conversion of various of the starting materials to various of the end products. This reaction sequence is illustrated by a flow sheet on which there are eleven structural formulae, one of which is number XXII:

On the following pages, the substituents in the above formula are defined as follows:

* * * X is selected from the group consisting of hydrogen, chloro, fluoro, trifluoromethyl, amino, lower alkylamino, alkanoylamino containing 2 to 4 carbon atoms, lower alkyl and monosubstituted lower alkyl wherein the substituent is selected from the group consisting of fluoro, lower alkylmercapto, lower alkoxy, amino, lower alkanoylamino, and alkanoyloxy and alkanoylamino each containing 2 to 4 carbon atoms; and YR wherein Y is selected from the group consisting of oxygen and sulfur; and R is selected from the group consisting of lower alkyl, benzyl and alkanoyl containing 2 to 4 carbon atoms;
X1 is selected from the group consisting of hydrogen, chloro, lower alkyl, mono fluoro substituted lower alkyl, and YR wherein Y and R are as previously defined;
X2 is selected from the group consisting of hydrogen, lower alkyl, hydroxy, mercapto, and YR in which Y and R are as previously defined;
A is selected from the group consisting of hydrogen, lower alkyl, fluoro and B2OCHB3 — wherein B2 is lower alkyl and B3 is selected from the group consisting of hydrogen and lower alkyl;
A1 is selected from the group consisting of hydrogen, lower alkyl and fluoro;
* * * * * *
R2 is selected from the group consisting of X3 and CO2X6 (mixed anhydride) in which X3 is selected from the group consisting of hydrogen, lower alkyl and benzyl and X6 is lower alkyl;
R3 and R4 when taken together with the nitrogen atom to which they are attached form a nitrogen heterocyclic ring selected from the group consisting of piperazyl, piperidyl, morpholinyl, pyrryl, pyrrolidyl, 2-(lower carbalkoxy) pyrrolidyl, and thiomorpholinly;
R3 and R4 when taken separately are each selected from the group consisting of hydrogen, aralkyl containing a total of up to 10 carbon atoms, amino, mono- and di-lower-alkylamino, acyl containing 1 to 4 carbon atoms, phenyl and mono-substituted phenyl wherein the substituent is selected from the group consisting of lower alkyl and lower alkoxy; and CH2B1 wherein B1 is selected from the group consisting of hydrogen, lower alkyl, lower carbalkoxy, and mono-substituted lower alkyl said substituent being selected from the group consisting of fluoro, hydroxy, lower alkoxy, amino, mono-and di-lower-alkylamino, lower carbalkoxy, and acylamino (preferably acetylamino), and acyloxy (preferably acetoxy) each containing 2 to 4 carbon atoms;
Provided that only one of said R3 and R4 substituents is selected from the group consisting of acyl containing 1 to 4 carbon atoms; and when one of said R3 and R4 substituents is monolower-alkylamino the other is lower alkyl; and when one of said R3 and R4 substitutents is selected from the group consisting of amino, di-lower-alkylamino, phenyl, mono-substituted phenyl, lower carbalkoxyalkyl, the other of said R3 and R4 substitutents is selected from the group consisting of hydrogen and lower alkyl;
* * * * * *
X5 is selected from the group consisting of —CH2, —CHOH, —CH

We have set forth the above definitions at length to emphasize the scope of the Conover teaching. However, it is conceded by Fields that the counts "find support" in the Conover application in the sense that "the particular group of compounds defined by the counts" may be arrived at by "a judicious choice from among the incredibly large number of possible substituents * * * assigned to formula XXII * * * of the Conover et al. application." Specifically, compounds defined by formula XXII lie within count 1 if (1) Conover's X is hydrogen or chloro at the 8-position, (2) X1 is hydrogen, (3) X2 is hydroxy at the 5-position, (4) A is hydrogen, (5) A1 is hydrogen, (6) R2 is hydrogen or lower alkyl, (7) R3 is hydrogen or methyl, (8) R4 is hydrogen or methyl, and (9) X5 is CH2 or CH (carboxy).1

THE BOARD'S OPINION

The board, starting with one of the 100 substituted amino acetates listed in Conover's Example LXIII,2 traced its way through Example LXV, Example LXXXVI, and the first sentence of the last paragraph of Example LXXXVII to arrive at a chemical differing from that recited in count 2 only in that it contains a 5-methoxy group in place of the 5-hydroxy group recital in that count. For the final reaction, the board relied on the last two sentences of the last paragraph of Example LXXXVII, which state:

The ether * * * groups present are converted to hydroxy * * * groups by treatment with hydrogen bromide in accordance with known procedures. The amphoteric products are obtained by careful neutralization with NaHCO3.

The board specifically found that "procedures for converting aromatic ethers to aromatic hydroxy compounds are well within the skill of the art," relying on "A well known textbook of organic chemistry" published in 1950 which states that 48% hydrobromic acid is a superior reagent for ether cleavage and on two working examples in Conover which teach analogous reactions with other compounds. In the particular reaction sequence traced by the board, this final reaction is said to result in the compound recited in count 2, and, on this basis, the board held that "the disclosures of these examples i. e., Examples LXIII, LXV, LXXXVI, and LXXXVII are linked so that by following out these processes the compound of count 2 must inevitably be formed." Accordingly, the board awarded priority to Conover on both counts.

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