Carter-Wallace, Inc. v. Davis-Edwards Pharmacal Corp., 70 C 369.

• Decision Date: 18 February 1972
• Docket Number: No. 70 C 369.,70 C 369.
• Parties: CARTER-WALLACE, INC., Plaintiff, v. DAVIS-EDWARDS PHARMACAL CORP., Defendant.
• Court: U.S. District Court — Eastern District of New York

341 F. Supp. 1303

CARTER-WALLACE, INC., Plaintiff, v. DAVIS-EDWARDS PHARMACAL CORP., Defendant.

No. 70 C 369.

United States District Court, E. D. New York.

February 18, 1972.

COPYRIGHT MATERIAL OMITTED

Jerome G. Lee, John D. Foley, George P. Hoare, Jr., New York City, (Morgan, Finnegan, Durham & Pine and Stephen R. Smith, New York City, of counsel), for plaintiff.

William H. Bisnoff, for defendant.

MEMORANDUM INCORPORATING FINDINGS of FACT and ORDER on ISSUES of VALIDITY and INFRINGEMENT

DOOLING, District Judge.

Unfortunately, the present memorandum must be long. However, if the trial program sensibly visualized by Graham v. John Deere Co., 1965, 383 U.S. 1, 17-18, 86 S.Ct. 684, 15 L.Ed.2d 545 is to be pursued — and this case peculiarly invites that — length is inevitable. The prior art brought into the case is very extensive and it requires a fairly discursive description to present it fairly. In addition, there are the background and factual investigations of the sequences of events preceding the invention of meprobamate and relating to the prosecution of the original and continuation applications for the patent in suit.

PRELIMINARY MATTERS

The chemical name, or, rather, one chemical name of meprobamate is 2,2-methyl-n-propyl-1,3-propanediol dicarbamate. The diagramatic representations of certain of the compounds involved in the evolution of meprobamate, copied from Chief Judge Friendly's opinion reversing the preliminary injunction, 443 F.2d at 876, are helpful. The starting molecule is that of propane, a molecule comprising three carbon and eight hydrogen atoms;

H H H | | | H-C-C-C-H | | | H H H A5602

If for the H atom appearing at each end of the propane molecule an OH, representing a hydroxyl radical, is substituted, the result is 1,3-propanediol, which may be represented thus:

H H H | | | HO-C-C-C-OH | | | H H H A5603

The diol is referred to as a 1,3 diol because a hydroxyl group, OH, is substituted for an H atom at carbon 1 and carbon 3 — for each carbon atom is given a number usually numbering from left to right, although the literature is not consistent, and, in addition, some of it identifies the carbon atoms by the Greek letters alpha, beta and gamma. It is usual in writing out the diagramatic representations of the diol derivative here involved to show the carbon 1 and carbon 3 parts as CH2 thus:

H | HO-CH2-C-CH2-OH | H A5604

It may be noted that CH2 is the additive factor in the progression from the methyl group CH3, to the ethyl group C2H5, to the propyl group C3H7. Indeed, the series goes on in the literature here involved to C18H37.

In the present case, the concern is with a "Markush Group" of three 2,2-di-substituted 1,3-propanediol dicarbamates and the disubstitution is by means of substituting for the H atoms attached to the middle C of the propanediol an alkyl radical (that is one of the CH3, C2 H5, C3 H7, etc. series) or an aryl radical (characterized by the presence of the benzene ring, represented by a hexagon). The compound of Claim 4 of the patent, meprobamate, is a dicarbamate ester; for the hydroxyl radical at each end of the diol diagram (at carbon 1 and carbon 3) is substituted a carbamate group. The general formula of the carbamate radical is as follows:

O || -O-C-NH2 A5605

A generalized diagram to illustrate the set of diols and esters to which the products of the patent and their "parent" diols belong is formed by using R1 and R2 to symbolize alkyl or aryl groups to be introduced in disubstitution at carbon 2 by using X1 and X2 to represent either the hydroxyl group of the starting diol or the organic acid radical substituted for one or both of the hydroxyl groups (OH) in the process of "esterification"; one such organic acid radical substitutable for a hydroxyl group in esterification is the carbamate radical. The generalized formula is as follows:

R1 | X1-CH2-C-CH2-X2 | R2 A5637

In the patent another generalized form is used by treating the CH2 of carbon 1 and carbon 3 portions as included in the X1 and X2 symbols thus:

The patent in question, No. 2,724,720, issued November 22, 1955, upon application of Frank M. Berger and Bernard J. Ludwig filed August 3, 1953, as a continuation-in-part of an earlier application, filed July 29, 1950, claimed as new products three different, 2,2-disubstituted, 1,3-propanediol dicarbamates, and claimed the three together as a "Markush Group." Directly in issue is only Claim 4 on 2-methyl-2-n-propyl-1,3-propanediol dicarbamate, represented thus:

O CH3 O || | || NH2C-O-CH2-C-CH2-O-C-NH2 | C3H7 A5638

It is not essentially denied (although at this point the defendant notes a special exception) that meprobamate was a new composition of matter, a new chemical compound. The "examples" of columns 3 and 4 of the patent describe procedures for obtaining each of the three new compounds. The method described is not new, and, as will appear, there is a history of making carbamates through the use of phosgene, COCl2. It has been conceded, for purposes of the present case, that the so-called "Yale I" (Ex. 162) and "Yale II" (Ex. 163) articles are prior art (although it is denied that either inventor knew of the Yale I and Yale II papers at the time of the invention). The Yale II paper at p. 3718 described the making of 2,2-diethyl-propanediol monocarbamate by a phosgene method similar to that described in the patent, but critically differing from it in the molar ratios used. The process, as described in the Yale II paper, produced a very low yield of monocarbamate (2.7% of what would have resulted if all molar quanta had combined in monocarbamate form). Later work by Dr. Berger and his associates indicated that the Yale II procedure would probably yield as a by-product diethyl-propanediol dicarbamate. Yale II did not mention and presumably did not detect any dicarbamate that was produced; the dicarbamate is all but insoluble in the toluene solvent of the Yale II process and in water, which was also involved in the Yale II reaction procedures. The consequence would apparently have been that any dicarbamates would have been in a lost layer of discardable residues between the toluene and water (with their respective solutes) and would have been wasted.

Apart from that possible, unintended, apparently quite unknown and certainly wholly undisclosed production and existence of one dicarbamate embraced in the original patent application — and its existence is a chemical probability and not a demonstrated fact — the dicarbamates of the patent and its applications were both unknown in nature and unsynthesized — certainly unisolated — in any known earlier chemical procedure. In that sense each of the three is a wholly new composition of matter and not anticipated in the sense of Section 102 of Title 35. The case is a Section 103 case on unobviousness.

The issue of infringement is not at this stage of the case a genuine issue either. Davis-Edwards does not deny that it has purchased, used and sold meprobamate without paying tribute to the patent. Davis-Edwards has, however, expressly reserved the point that Carter-Wallace could not enforce the patent against Davis-Edwards because of its alleged patent abuse and anti-trust violations.

BACKGROUND — "CNS DEPRESSANTS"

The prior art has been developed in a very full and descriptive way, not in terms of trying to show that there were specific products which themselves indexed the route to the article of the patent but rather by attempting to show that work going back to the last century converged on and, toward the end, immediately implicated the compounds of the patent. To a very considerable extent, the approach has as its premises a special view of the central nervous system depressant drugs as a group and their mode of operation as well as a special view of the nature and mode of operation of meprobamate and the other products of the patent in their asserted roles as anti-convulsants, relaxants of the skeletal muscles and specific tranquilizers for states of anxiety and tension.

Depressant drugs for use in relation to the central nervous system embrace an immense number of drugs variously identified as anesthetics, analgesics, hypnotics, "narcotics," sedatives and, only more recently and debatably, tranquilizers for specific relief of states of anxiety and tension. An authoritative textbook in the field, copyright in 1941, but in its sixteenth printing in October, 1948 (Ex. AX), defined central nervous system depressant drugs with the note that there were considerable overlappings in the classifications. The classification given was, 1. General anesthetics (e. g. ether, cyclopropane and ethylene); 2. Sedative-hypnotic-soporific drugs, (e. g., barbiturates, chloralhydrate, bromides); 3. Narcotics (e. g., morphine and related alkaloids); and 4. Analgesics and antipyretics (e. g., the salicylates, acetanilid, aminopyrine). In this classification, "anesthesia" meant loss of all modalities of sensation and also loss of consciousness. Surgical anesthesia was differentiated from a lesser "basal anesthesia" obtained by giving sufficient pre-anesthetic medication inducing unconsciousness but not sufficient depression to permit surgical procedures. Narcosis, variously defined, meant in the classification a condition of analgesia accompanied by deep sleep or stupor, and differing from anesthetic medication in that pain is relieved before sleep or unconsciousness supervenes. Hypnosis in the pharmacological sense meant a condition of sleep produced by a somnifacient drug. Sedation meant a milder degree of hypnosis in which the patient is "awake but calmed." Analgesia meant obtundation of pain, differing from narcosis in relieving pain without stupefaction or unconsciousness. Dr. Berger, one of the co-inventors, differentiated eight classes of central nervous system depressants (Ex. 113). First, sedative-hypnotic-anesthetic; Second, anti-convulsants; Third, analgesics; Fourth, mu...