In re Gaertner

604 F.2d 1348, 202 U.S.P.Q. (BNA) 714, 1979 CCPA LEXIS 221
CourtCourt of Customs and Patent Appeals
DecidedAugust 2, 1979
DocketAppeal No. 79-528
StatusPublished
Cited by4 cases

This text of 604 F.2d 1348 (In re Gaertner) 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
In re Gaertner, 604 F.2d 1348, 202 U.S.P.Q. (BNA) 714, 1979 CCPA LEXIS 221 (ccpa 1979).

Opinion

MARKEY, Chief Judge.

The Patent and Trademark Office (PTO) Board of Appeals (board) affirmed the rejection under 35 U.S.C. § 185 of application No. 599,574 filed July 28, 1975, and entitled “Oxazolidinone Phosphonates.” We affirm.

Background

On June 17, 1974, Gaertner filed application No. 479,932 (parent) directed to a class of herbicidal compounds having the formula:

wherein R and R1 are each selected from alkyl of 1 to 6 carbon atoms, alkenyl of 3 to 4 carbon atoms, and the mono-chloroderivatives of such alkyl and alkenyl. As disclosed in the application, the compounds are generally prepared by first reacting methyl or ethyl glycinate with formaldehyde and then adding an aliphatic phosphite diester to the reaction product. R and R1 are determined by the ester groups on the aliphatic phosphite reactant.

The specification contains five detailed examples describing the preparation of specific compounds within the class. Example 1 teaches:

EXAMPLE 1
A suitable reaction vessel is charged with 25.2 grams (0.2 mole) of methyl gly-cinate hydrochloride in 100 ml. of methanol. The solution is stirred during neutralization with 25% sodium methozide solution in methanol, after which 2.5 grams of hydrochloride is added. The resultant solution is filtered to remove salt, and 32 grams (0.4 mole) of 37% formalin is added slowly with cooling to maintain the temperature below 30 °C. After stirring for about 15 minutes, 27.6 grams (0.2 mole) of diethyl phosphite is added at one time.
The mixture is stirred and heated to distill methanol, and then 250 ml. of toluene is added and the temperature raised to azeotrope water. The mixture in toluene is heated at about 115 °C. for 1 hour, after which it is cooled, and the cooled solution decanted from a small insoluble residue. The toluene is distilled down to 1 mm./70°C., and the residual oil is cooled, followed by the addition of 300 ml. of ether. The solution is then filtered, and the ether is stripped leaving a dark amber oil.
This oil is distilled in a molecular still at 155-165 °C. wall temperature at 3p, , and the yellow oil obtained is redistilled in a magnetically stirred molecular still at 100-129 °C. bath temperature at 4 ¡1. The product obtained is N-(diethoxyphosphinylmethyl)oxazolidin-5-one, nd22 1.-4548. Elemental analysis gives 40.34% carbon, 7.04% hydrogen, 5.73% nitrogen and 13.07% phosphorus as against calculated values of 40.51%, 6.80%, 5.91% and 13.06% for C8H16N05P.

Examples 2 through 5 differ from Example 1 only in the aliphatic phosphite diester selected and in the distillation conditions employed. The application contains eight claims directed to the compound per se. Claim 1, the sole independent claim, generically recites the entire class of compounds. Claims 2 and 4 are sub-generic. The remaining five claims are each specific to a different one of the compounds prepared in Examples 1 through 5.

On January 17,1975, the examiner rejected claims 1, 2 and 4 under 35 U.S.C. §§ 101, 112,1 finding “no adequate teaching of how [1350]*1350to use any compounds other than those of the examples” and “no examples, of any kind, of any chloro compounds.” (emphasis in original). Gaertner deleted the monochloro derivatives from the specification and claim 1. The application was allowed on May 14, 1975 and thereafter became abandoned on August 14, 1975 for nonpayment of the issue fee.

On July 28, 1975, Gaertner filed the instant application No. 559,574. The accompanying declaration labels it a continuation-in-part (CIP) of the parent containing “subject matter * * * not common to said earlier application.” The instant application differs from the parent as filed in three instances, one being the identification of the parent at the beginning of the specification as required by 37 CFR 1.78(a). A second difference is the addition of an Example 6 describing the use of di(2-chloro-propyl) phosphite, a known aliphatic diester, in the preparation of a compound within the above formula wherein R and R1 are 2-chloropropyl, a mono-chloro derivative. More specifically, Example 6 teaches:

EXAMPLE 6
A suitable reaction vessel is charged with 12.5 grams (0.1 mole) of methyl gly-cinate hydrochloride in 50 ml. of methanol. The solution is stirred during neutralization with 25% sodium methoxide solution in methanol, after which 1.3 grams of additional hydrochloride is added. The resultant solution is stirred for about 30 minutes and filtered. The filtrate is placed in an ice bath, and 16 grams (0.2 mole) of formalin is added. After stirring for about 1 hour, the solution is concentrated in a rotary evaporator at p30°C. to remove methanol. It is then diluted with benzene, dried over anhydrous sodium sulfate, and further concentrated in the rotary evaporator.
The residual oil is dissolved in 100 ml. of benzene and treated immediately with 23.5 grams (0.1 mole) of di(2-chloropro-pyl)phosphite. About 4 drops of concentrated HC1 is added, and the product is concentrated in the rotary evaporator starting at p 20 °C. and up to steam temperature, finally at p 0.5mm. An oil is obtained, and a portion of that oil is distilled in a molecular still at 145-159 °C. wall temperature' at 5-8 p, and finally at 1 p . The product obtained as a viscous oil is N-[di(2-chloro-l-propoxy)phosphinyl-methyl]oxazolidin-5-one, Nd22 1.4812.
Elemental analysis gives 21.24% chlorine, 4.13% nitrogen and 9.19% phosphorus as against calculated values of 21.22%, 4.9% and 9.27% for C10 H j 8 Cl 2 NO 6 P.

The remaining difference is the addition of dependent claim 9 which is specific to the compound prepared in Example 6.

The CIP declaration acknowledges the prior filing, by Gaertner’s assignee, of nine foreign counterparts of the CIP, including Example 6, just before June 17, 1975. The PTO Group 220 (Security Group), Licensing and Review Section, denied Gaertner’s petition for a retroactive license for foreign filing under 35 U.S.C. § 184,2 finding that [1351]*1351he had not provided the required verified showing of facts and that his showing indicated no inadvertence in filing abroad without a license. Gaertner’s petition to the Commissioner was denied. The examiner then rejected “the application” under 35 U.S.C. § 185 3 for non-compliance with the licensing requirements of 35 U.S.C. § 184.

The Board

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604 F.2d 1348, 202 U.S.P.Q. (BNA) 714, 1979 CCPA LEXIS 221, Counsel Stack Legal Research, https://law.counselstack.com/opinion/in-re-gaertner-ccpa-1979.