Hartford National Bank & Trust Co. v. EF Drew & Co.

• Decision Date: 10 October 1956
• Docket Number: No. 11774.,11774.
• Citation: 237 F.2d 594
• Parties: HARTFORD NATIONAL BANK & TRUST COMPANY, Trustee, and Philips Laboratories, Inc., v. E. F. DREW & CO., Inc., Appellant.
• Court: U.S. Court of Appeals — Third Circuit

237 F.2d 594 (1956)

HARTFORD NATIONAL BANK & TRUST COMPANY, Trustee, and Philips Laboratories, Inc., v. E. F. DREW & CO., Inc., Appellant.

No. 11774.

United States Court of Appeals Third Circuit.

Argued April 10, 1956.

Decided October 10, 1956.

Rehearing Denied November 15, 1956.

Harry C. Bierman, New York City, for appellant.

Arthur G. Connolly, Wilmington, Del. (Thomas Cooch, Thomas S. Lodge, Connolly, Cooch & Bove, Wilmington, Del., on the brief), for appellees.

Before BIGGS, Chief Judge, and McLAUGHLIN and STALEY, Circuit Judges.

BIGGS, Chief Judge.

The plaintiff, Hartford National Bank and Trust Company (Hartford), holds United States Patent No. 2,441,091 as trustee for N. V. Philips' Gloeilampen-fabrieken, et al. The plaintiff, Philips Laboratories, Inc. (Philips), is the exclusive licensee of Hartford with the right to sue infringers. The plaintiffs allege that claims 12 and 24¹ have been infringed by the defenadnt E. F. Drew & Co., Inc. (Drew). The original application was filed in the Netherlands by Drs. Jacob van der Vliet and Willem Stevens on January 28, 1943 and the date of invention for the purpose of priority therefore is limited to that day. The court below held the claims in issue valid and infringed. D.C.D.Del.1955, 133 F. Supp. 648.

The patent discloses a method of preparing synthetically 7-dehydrocholesterol, provitamin D3, which when irradiated by ultra violet light is converted to vitamin D3. The irradiation process is not covered by the disclosures of the patent and is not in issue. The patent teaches that one can synthetize a sterol derivative such as cholesterol ester by reacting it with a halogenating agent, for example, with a bromine compound such as N-bromosuccinimide. This causes a corresponding halogen atom to be substituted for the hydrogen atom at the 7-position, at carbon atom 7 of the cholesterol molecule. The next or second step, as taught by the patent specification, consists of subjecting the resulting 7-halogenocholesterol to the action of some dehydrohalogenating chemical. The dehydrohalogenation removes the halogen atom from the 7-position and the hydrogen atom from the 8-position and introduces a double bond at the 7-8 position of the cholesterol molecule. The element of novelty or invention lies in the second step. The double bond changes the therapeutically inert material into provitamin D3 which thereafter can be converted to the therapeutically active valuable material, vitamin D3, by simple ultra violet irradiation.

We have said that the element of novelty or invention lies in the second step, the creation of the double bond at the 7-8 position by dehydrohalogenation. The former art proves the novelty rather than disproves it. A brief history demonstrates this. Vitamin D3 is the antirachitic found in cod liver oil and deemed to be essential for the creation of strong bones and teeth. Prior to 1935 one method of creating vitamin D3 consisted of cooking mussels, abstracting the meat therefrom by a fat solvent, saponifying the fat and purifying the remainder by crystalization thereby creating some 7-dehydrocholesterol. This was the so-called "mussel" method.

Another method employed was that of Windaus which used raw material cholesterol esterfied by benzoic or acetic acid dissolved in an organic solvent and oxidized by chromic acid. A keto group was thus introduced in the 7-position. The keto ester was reacted with hydrogen to form an hydroxyl. The hydroxyl group was esterfied and the ester group along with the hydrogen atom was then removed to form a double bond between positions 7 and 8. The compound was then saponified to restore the hydroxyl group. At least six chemical steps were necessary to accomplish the result desired. What van der Vliet and Stevens brought to the art by the disclosures of the patent in suit was a novel and comparatively inexpensive method of creating 7-dehydrocholesterol in quantity by the formation of the double bond as indicated.

Drew attacked the patent vigorously, asserting it discloses nothing of novelty over the prior art, relying principally in the court below on publications by both Wohl² and Ziegler.³ The Wohl article discloses that N-bromoacetamide, and similar substances, will react with unsaturated compounds to place a bromine atom at the carbon atom adjacent to the double bond. But Wohl did not work with cholesterol molecules or, if he did, his publication did not disclose it. Wohl certainly did not disclose the novel step, which van der Vliet and Stevens assert constitutes their invention, whereby the 7-halogenocholesterol was dehydrohalogenated to create 7-dehydrocholesterol. Wohl possesses little significance save as a starting point for Ziegler; indeed, on the appeal, Drew does not argue that the Wohl article affords anticipation of the disclosures of the patent in suit.

The Ziegler article was before the Patent Examiner during the prosecution of the application for the patent in suit. The patent issued despite this publication. This greatly detracts from the weight to be given to it but viewing the article here, as it were de novo, we are of the opinion that it cannot fairly be said to afford anticipation of van der Vliet's and Stevens' disclosure. Ziegler and his co-workers had Wohl's statements before them. Ziegler did deal with cholesterol groups. He does refer to compounds created by reacting such groups with acetabromamid and N-Bromosuccinimide for bromination of unsaturated compounds in the allyl⁴ position. The Ziegler article is voluminous. The article in the original German...