Application of Rosselet
| Decision Date | 01 July 1965 |
| Docket Number | Patent Appeal No. 7334. |
| Citation | 347 F.2d 847,52 CCPA 1533 |
| Parties | Application of Jean P. ROSSELET, Oldrich K. Sebek and George B. Spero. |
| Court | U.S. Court of Customs and Patent Appeals (CCPA) |
Eugene Retter, Gerard A. Blaufarb, Kalamazoo, Mich., for appellants.
Clarence W. Moore, Washington, D. C. (J. E. Armore, Washington, D. C., of counsel), for Commissioner of Patents.
Before WORLEY, Chief Judge, and RICH, MARTIN, SMITH and ALMOND, Judges.
This appeal is from the decision of the Patent Office Board of Appeals affirming the examiner's rejection of product claims 3 and 5 in application serial No. 701,967, filed December 11, 1957, for "Organic Compounds and Process." No claims have been allowed.
The invention relates to steroid compounds and, according to the application, is "particularly concerned with 6-methyl-16a-hydroxyhydrocortisone, 1-dehydro-6-methyl-16a-hydroxyhydrocortisone, 6-methyl - 9a - fluoro - 16a - hydroxyhydrocortisone, 1-dehydro-6-methyl-9a - fluoro-16a - hydroxyhydrocortisone, the 16, 21-diesters thereof, the 11-keto analogues and the esters thereof and a method for the production thereof." The application further says:
The new compounds * * * are highly active adrenocortical hormones having greater glucocorticoid activity than hydrocortisone or cortisone. In addition these compounds have diuretic activity and have saltlosing properties which make them especially well suited in the management of chronic congestive heart failure and in the treatment of cirrhosis of the liver, the nephrotic and adrenogenital syndromes and the treatment of eclampsia and preeclampsia.
The claimed invention, however, is narrower than the above broad description, the two claims reading:
Thus, claim 5 defines the compound of the formula
and claim 3 defines the compound of the same formula except that the 9a-fluoro atom is replaced by hydrogen.
The references relied on are:
Bernstein (IV) 2,789,118 Apr. 16, 1957
Bernstein (V) J. Am. Chem. Soc. Nov. 5, 1956
78, 5693-4
Spero (I) J. Am. Chem. Soc. Dec. 5, 1956
78, 6213-4
Spero (II) J. Am. Chem. Soc. Mar. 20, 1957
79, 1515-6
There are four separate rejections: The rejection of claim 3 "as unpatentable over Spero (I) in combination with Bernstein (IV)"; the rejection of claim 5 "as unpatentable over Spero (II) in combination with Bernstein (V)"; and the rejection of claim 5 "as unpatentable over each of the two Bernstein references * * *."
Spero (I) reports the results of studies on the 6-methylation of various steroids. The reference discloses 1-dehydro-6a-methyl-hydrocortisone which was found to be "sixteen times as active as hydrocortisone" in the "glycogen deposition (glucocorticoid) assay" without showing "salt retaining (mineralocorticoid) activity." This compound differs from the compound of claim 3 in lacking the 16a-hydroxy substituent. The reference says:
* * * demonstration of the absence of mineralocorticoid activity in the presence of high glucocorticoid activity for 6-methylhydrocortisone, the synthesis of which is presently described, was unpredictable and is of considerable interest. Extension of the study to the 1-dehydro series has resulted in the most pronounced selective enhancement of cortical activities reported to date. Footnotes omitted.
Spero (II) refers to Spero (I) as having "reported * * * the preparation of a number of 6-methylated analogs of adrenal hormones which show unusual potentiation of glucocorticoid activity with no sodium-retaining properties" and says that "The group of 9a-fluoro- and 21-fluoro-6-methyl steroids reported herein represents a continuation of this work." 1-Dehydro-6a-methyl-9a-fluoro-hydrocortisone is disclosed and is included among those compounds showing "considerably greater glucocorticoid and anti-inflammatory activity * * * than does hydrocortisone in animal assays." This compound differs from the compound of claim 5 in lacking the 16a-hydroxy substituent.
Bernstein (IV) discloses, inter alia, 1-dehydro-16a-hydroxyhydrocortisone and 1-dehydro - 9a-fluoro - 16a-hydroxyhydro-cortisone and says the compounds "are useful as anti-inflammatory agents in the treatment of arthritis, asthma, burns, bursitis, and the like, and also in the treatment of skin disorders and collagen diseases."
Bernstein (V) additionally discloses that the 9a-fluorocompound of Bernstein (IV), is "about 13 times more active than hydrocortisone" in the rat liver glycogen assay and is one of "the most active glucocorticoids hitherto reported which * * * is devoid of sodium-retaining properties." The conclusion is reached that "16a-hydroxylation abolishes the sodium-retaining property of 9a-fluorosteroids without destroying their glucocorticoid activity."
The following table summarizes the structural relationships between the claimed compounds and the pertinent prior art compounds, the base compound in each instance being 1-dehydrohydrocortisone (prednisolone):
6a-methyl 9a-fluoro 16a-hydroxy
----------------------------------------------------------------------
Claim 3 X X
Spero (I) X
Bernstein (IV) X
Claim 5 X X X
Spero (II) X X
Bernstein (V) X X
It should now be clear that the rejection of claim 3 as unpatentable over Spero (I) in combination with Bernstein (IV) and the rejection of claim 5 as unpatentable over Spero (II) in combination with Bernstein (V) present parallel issues, viz., obviousness of the claimed compounds in view of the respective Spero compounds, which differ from the claimed compounds solely in the absence of a 16a-hydroxy substituent, and in view of the respective Bernstein teachings which show that 16a-hydroxy substituents are found on closely related steroids, the Bernstein compounds themselves differing from the claimed compounds solely in the absence of a 6a-methyl substituent. Thus appellants are not, nor do they pretend to be, the first to 6-methylate or 16-hydroxylate steroids of the type here involved. What appellants have done is to provide hydrocortisones bearing both these substituents and, accordingly, novelty of the claimed compounds has been conceded.
While the issue could be stated, alternatively, as the converse of the...
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