Application of Lewis H. Sarett

327 F.2d 1005
CourtCourt of Customs and Patent Appeals
DecidedMay 8, 1964
DocketPatent Appeal 7051
StatusPublished
Cited by12 cases

This text of 327 F.2d 1005 (Application of Lewis H. Sarett) is published on Counsel Stack Legal Research, covering Court of Customs and Patent Appeals primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Application of Lewis H. Sarett, 327 F.2d 1005 (ccpa 1964).

Opinion

RICH, Judge.

This appeal is from the decision of the Patent Office Board of Appeals, affirming the rejection of claims 8-19 in Sarett’s application serial No. 600,163, filed July 26, 1956, entitled “Chemical Compounds and Process for Preparing the Same.” 1

The invention relates to the oxidizing of primary and secondary alcohols to corresponding carbonyl compounds. In essence, mild oxidizing agents are used, *1006 thus preventing oxidation of unsaturated bonds in the alcohol and also preventing oxidation beyond the desired stage. Alkaline medium is used to avoid undesirable side reactions at acid-sensitive portions of alcohol molecules.

With respect to the naming of the alcohols to be oxidized, there are two groups of claims: (1) claims 8-14 which define the process of oxidizing specific complex alcohols using “pyridine-chromium trioxide complex” as oxidizing agent; and (2) claims 15-19 which define the process of so oxidizing primary and secondary alcohols broadly. In this group the oxidizing agent is defined as in group (1) except for claim 15 in which it is more broadly defined as “a tertiary amine-chromium trioxide complex,” pyridine being a tertiary amine, the tertiary amines being further restricted to “pyridine, lower alkyl substituted pyri-dines, and benzosubstituted pyridines.” Claims 17-19, dependent on claim 16, specify, respectively, that the alcohol is aliphatic, or a phenanthrene compound, or a eyclopentanopolyhydrophenanthrene compound.

Claims 8 and 16 are representative of groups (1) and (2) respectively and read (our emphasis):

“8. A process for preparing 3-acetoxy-ll,20-diketopregnane which comprises intimately contacting 3-acetoxy-ll-keto-20-hydroxy-pregnane with pyridine chromium trioxide complex at a pH in excess of 7.0 and recovering 3-acetoxy-ll, 20-diketopregnane from the resulting reaction mixture.
“16. In the process of oxidizing an alcohol having at least one hydrogen atom attached to the carbon atom bearing the hydroxyl substit-uent to the corresponding carbonyl compound, the improvement which comprises intimately contacting said alcohol at a pH in excess of 7 with a pyridine-chromium trioxide complex, and recovering the carbonyl compound from the resulting reaction mixture.”

The definition of the alcohol in claim 16 means, in plain English (the use of which is often prevented by Patent Office practice), a primary or secondary alcohol.

There are two grounds of rejection: (1) all claims, double patenting over Arth et al., a commonly-assigned patent in which appellant is one co-inventor; 2 and (2) claims 15-19, indefiniteness in their broad definitions of the alcohols, under 35 U.S.C. § 112. 3

The complexity of issues requires that we outline briefly the disclosure and claims of appellant’s application and of the Arth et al. patent and set the legal problem in its factual background.

Appellant’s Disclosure

Appellant asserts as his broad invention the oxidizing of primary and secondary alcohols, particularly unsaturated alcohols, in alkaline medium with organic base-chromium trioxide complexes. Preferred bases are pyridine, gamma-pico-line, beta-picoline, lutidines, quinoline, diethyl formamide and the like. Oxidation is effected by intimately contacting the alcohol with oxidizing agent in inert solvent. Primary alcohols are oxidized to aldehydes, secondary alcohols to ketones. The specification includes many types of alcohols to which the process is applicable. Over sixty types are disclosed including aliphatic, aralkyl, aral-kenyl, aralkinyl alcohols, to name a few, as well as steroid alcohols and steroid derivatives such as pregnanes, cholanes, etc.

Appellant says his process is especially useful in oxidizing certain hydroxy *1007 (-OH) functional groups on steroids to their corresponding keto (=0) groups. For example, 17-position hydroxys may be oxidized to 17-ketos without affecting unsaturated bonds elsewhere in the molecule. The specification includes thirty-one specific examples in which alcohols ranging from cyelopentanopolyhydro-phenanthrene derivatives to n-butyl alcohol (allowed claim 7) are oxidized. Included are pregnanes, ergosterols, phenanthrenes, pyrans, benzyl alcohols, propene alcohols, etc.

Claims 8-14, defining appellant’s process, set forth specific complex alcohols as follows: 4 claim 8 — 3-acetoxy-ll-keto-20-hydroxypregnane; claim 9 — 3,21-diacetoxy - ll-keto-17,20-dihydroxypregnane; claim 10— ÁSCT,22-3-acetoxy-7,11-dihydroxyergostadiene; claim 11 — 4b-methyl-7-ethylene-dioxy - 1,2,3,4,4a,4b,5, 6,7,8,10,10a - dodeeahydrophenanthrene1,4-diol; claim 12 — 4b-methyl-7-ethy-lenedioxy - l,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene - 1,4-diol-l-ace-tate; claim 13 — 4b-methyl-7-ethylenedi-oxy - l,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-l-one-4-ol; claim 14 —4b-methyl - 7-ethylenedioxy-l,2,3,4,4a, 4b,5,6,7,8,10,l0a - dodecahydrophenanthrene-l-ol-4-one. In all the aforementioned alcohols, hydroxy groups are oxidized to keto groups in the claimed process.

Claim 16, supra, is the broadest of claims 15-19. It is inclusive of all primary and secondary alcohols. Claim 15 differs from 16 only in its definition of the complex formerly used in preparing the oxidizing agent. It too, therefore, includes all primary and secondary alcohols.

The Arth et al. Patent Disclosure

Although on the double patenting rejection here involved we are concerned only with what this patent claims, in order to understand what it does claim and discuss the opposing arguments on this question, it is necessary to give some consideration to the disclosure of the specification, bearing in mind always that the teachings of that specification (inclusive of its claims) are not prior art with reference to appellant’s invention as defined in the claims on appeal, since the application on appeal and the patent have the same effective filing date. In re Coleman et al., 189 F.2d 976, 38 CCPA 1156. We preface this consideration by quoting the Patent Office position as stated in the solicitor’s brief:

“The position of the Patent Office with respect to this ground of rejection is that the instant claims are directed to essentially the same invention as that recited in any of Arth’s process claims 9, 10, 11, 12 and 16, and that the two groups of claims differ only in scope.” [Emphasis added.]

Arth et al., as does appellant, disclose processes for oxidizing specifically 4b-methyl-dodeeahydrophenanthrene-l,4-diol-7-one to 1,4,7-triones. 5 In addition, however, Arth et al. teach processes for isomerizing various triones by alkali treatment to form stereoisomers thereof.

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327 F.2d 1005, Counsel Stack Legal Research, https://law.counselstack.com/opinion/application-of-lewis-h-sarett-ccpa-1964.