DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1–7 is/are rejected under 35 U.S.C. § 103 as being unpatentable over Pinchman et al. (U.S. Publication No. 2021/0061730, hereinafter “Pinchman”) in view of Hong et al. (U.S. Publication No. 2022/0144744 A1, hereinafter “Hong”; corresponding to WO 2020/248126).
Hong’s U.S. publication issued after the September 13, 2021 effective filing date of the present application, but the application has a June 11, 2019 international filing date and is the U.S. national-stage counterpart of WO 2020/248126 A1, published December 17, 2020. Accordingly, Hong may be relied upon through the earlier-published WO document under § 102(a)(1), or through its U.S. publication under § 102(a)(2).
Pinchman discloses a continuous-flow method for producing 1,3-diacetylbicyclo[1.1.1]pentane by mixing a [1.1.1]propellane composition with 2,3-butanedione under conditions selected to react the [1.1.1]propellane with the 2,3-butanedione and thereby produce 1,3-diacetylbicyclo[1.1.1]pentane. Pinchman further discloses exposing the propellane and 2,3-butanedione to ultraviolet light, including radiation having a wavelength of about 350–380 nm. See Pinchman, paragraphs [0069]–[0070], publication pages 8–9; claims 14–15.
Pinchman also discloses forming [1.1.1]propellane in a solvent selected from diethyl ether, diethoxymethane, dibutyl ether, methyl tert-butyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and mixtures thereof. Pinchman expressly identifies a mixture of dibutyl ether and tetrahydrofuran and a mixture of dibutyl ether and 2-methyltetrahydrofuran. See Pinchman, paragraph [0063], publication page 7. Dibutyl ether is an acyclic ether having eight carbon atoms, whereas tetrahydrofuran and 2-methyltetrahydrofuran are cyclic ethers.
Pinchman further teaches that the [1.1.1]propellane composition produced according to its process may be used directly, without isolation, in the continuous-flow process for producing a [1.1.1]propellane derivative by adding further processing stages to the propellane-production process. Pinchman specifically identifies 1,3-diacetylbicyclo[1.1.1]pentane as one of those derivatives. See Pinchman, paragraphs [0069]–[0070], publication page 8.
Pinchman therefore teaches the claimed propellane, 1,2-diketone, photoreaction, acyclic ether solvent having at least five carbon atoms, cyclic ether compound, and 1,3-disubstituted BCP product. To the extent Pinchman does not expressly state that its specifically disclosed dibutyl ether/tetrahydrofuran solvent mixture is retained in the reaction solution during irradiation with 2,3-butanedione, Hong confirms that dibutyl ether is suitable as the acyclic ether solvent for the same photochemical reaction.
More particularly, Hong discloses in Comparative Example 1 a solution of unsubstituted [1.1.1]propellane in n-butyl ether, i.e., dibutyl ether. Hong combines that propellane solution with 2,3-butanedione, irradiates the resulting solution with a 313-nm LED, maintains the reaction at 0–5°C for 15 minutes, and obtains the corresponding 1,3-diacetyl bicyclo[1.1.1]pentane product in 85% yield. See Hong, paragraph [0039], publication pages 3–4.
It would have been obvious to one of ordinary skill in the art before the effective filing date to use Pinchman’s expressly disclosed dibutyl ether/tetrahydrofuran propellane composition directly in Pinchman’s downstream propellane/2,3-butanedione photoreaction, as suggested by Pinchman’s teaching that the propellane composition may be used directly without isolation. Hong independently establishes that dibutyl ether is compatible with and effective as a solvent in the same photochemical reaction between unsubstituted [1.1.1]propellane and 2,3-butanedione.
The skilled artisan would have been motivated to retain Pinchman’s dibutyl ether/tetrahydrofuran solvent system because doing so would eliminate an unnecessary propellane-isolation or solvent-exchange operation, simplify the sequential flow process, and retain solvents that Pinchman expressly identifies as suitable for preparation and direct downstream use of the propellane composition. Hong provides a reasonable expectation that the dibutyl ether component would not interfere with the photoreaction and would permit formation of the same 1,3-diacetyl bicyclo[1.1.1]pentane product. The tetrahydrofuran component would remain present as a conventional solvent component of Pinchman’s mixed-ether propellane composition.
The proposed modification constitutes combining known process elements according to known methods to obtain the predictable result expressly taught by both references. It also constitutes applying Hong’s known dibutyl-ether photoreaction conditions to Pinchman’s closely related process. These are recognized obviousness rationales under KSR International Co. v. Teleflex Inc., 550 U.S. 398, 417–18 (2007), and MPEP §§ 2141 and 2143.
The resulting process subjects [1.1.1]propellane and 2,3-butanedione, a 1,2-diketone, to a photoreaction in a solvent containing dibutyl ether, an acyclic ether having at least five carbon atoms, while the reaction solution contains tetrahydrofuran, a cyclic ether compound, and produces 1,3-diacetyl bicyclo[1.1.1]pentane. Accordingly, claim 1 would have been obvious over Pinchman in view of Hong.
Claim 2
Claim 2 further requires that the acyclic ether solvent have 5–10 carbon atoms. Pinchman expressly discloses dibutyl ether in its solvent mixture with tetrahydrofuran. Dibutyl ether has eight carbon atoms and therefore falls within the claimed range. See Pinchman, paragraph [0063], publication page 7. Claim 2 would have been obvious for the reasons set forth regarding claim 1.
Claim 3
Claim 3 further requires that the acyclic ether solvent have five or six carbon atoms. Pinchman expressly identifies methyl tert-butyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and mixtures thereof as suitable solvents for the propellane-forming process. Methyl tert-butyl ether is an acyclic ether having five carbon atoms, while tetrahydrofuran and 2-methyltetrahydrofuran are cyclic ethers. See Pinchman, paragraph [0063], publication page 7.
It would have been obvious to select a mixture of methyl tert-butyl ether and tetrahydrofuran from Pinchman’s limited group of expressly disclosed solvents and mixtures because both components are expressly identified as suitable solvents for the same propellane-production process. Substituting methyl tert-butyl ether for dibutyl ether would have amounted to the predictable substitution of one expressly disclosed acyclic ether solvent for another for the same solvent function. Pinchman’s teaching that the resulting propellane composition may be used directly in a downstream derivative-forming reaction would have provided a reasonable expectation that the selected mixed-ether composition could likewise be used in the photoreaction of paragraph [0070].
Claim 4
Claim 4 further requires that the 1,2-diketone be a diacetyl compound or a glyoxylic-acid compound. Pinchman expressly reacts [1.1.1]propellane with 2,3-butanedione, which is diacetyl, to produce 1,3-diacetylbicyclo[1.1.1]pentane. See Pinchman, paragraph [0070], publication page 8, and claim 14. Hong likewise uses 2,3-butanedione in Comparative Example 1. See Hong, paragraph [0039]. Claim 4 would have been obvious for the reasons set forth regarding claim 1.
Claim 5
Claim 5 further requires that the cyclic ether compound be a tetrahydrofuran compound. Pinchman expressly identifies a mixture of dibutyl ether and tetrahydrofuran and a mixture of dibutyl ether and 2-methyltetrahydrofuran as solvent systems for producing the propellane composition. See Pinchman, paragraph [0063], publication page 7. Pinchman further teaches using the resulting propellane composition directly, without isolation, in the downstream derivative-forming process. See Pinchman, paragraph [0069], publication page 8. Thus, the modified reaction solution would contain tetrahydrofuran or 2-methyltetrahydrofuran as required by claim 5.
Claim 6
Claim 6 further requires irradiation with light having a wavelength of 200–600 nm. Pinchman expressly discloses ultraviolet radiation having a wavelength of about 350–380 nm. See Pinchman, paragraph [0070], publication page 8, and claim 15. Hong additionally discloses a general wavelength range of 300–350 nm and expressly uses a 313-nm LED in Comparative Example 1. See Hong, paragraphs [0012] and [0039], publication pages 1 and 3. Each of these disclosed wavelengths falls within the claimed 200–600-nm range.
Claim 7
Claim 7 further requires a photoreaction temperature of −50°C to 50°C. Hong expressly discloses that the continuous photochemical reaction may be conducted at 0–30°C, preferably 0–5°C. See Hong, paragraph [0013], publication page 1. Hong’s Comparative Example 1 specifically conducts the propellane/2,3-butanedione photoreaction at 0–5°C. See Hong, paragraph [0039], publication pages 3–4. These temperatures fall entirely within the claimed range.)
It would have been obvious to conduct Pinchman’s photoreaction at Hong’s disclosed temperature because Hong applies that temperature to the same photochemical reaction between unsubstituted [1.1.1]propellane and 2,3-butanedione in dibutyl ether and demonstrates successful formation of the same 1,3-diacetyl bicyclo[1.1.1]pentane product. The skilled artisan therefore would have had both a reason and a reasonable expectation of success in employing Hong’s temperature conditions. Accordingly, claim 7 would have been obvious over Pinchman in view of Hong
Claim Rejections - 35 USC § 112
Claims 1–7 is/are rejected under 35 U.S.C. § 112(a) as failing to comply with the enablement requirement. The specification, while being enabling for certain photoreactions employing 2,3-butanedione, cyclopentyl methyl ether or methyl tert-butyl ether, and tetrahydrofuran or 2-methyltetrahydrofuran under the specifically exemplified irradiation conditions, does not reasonably provide enablement commensurate with the full scope of claims 1–7.
The specification does not enable a person skilled in the art to carry out the claimed method throughout the full scope of the interacting acyclic-ether-solvent, cyclic-ether, and 1,2-diketone genera without undue experimentation.
Under the current claims, claim 1 broadly requires subjecting [1.1.1]propellane and a “1,2-diketone compound” to a photoreaction in a solvent including any acyclic ether having five or more carbon atoms, while the reaction solution contains any cyclic ether compound. Claim 1 places no upper limit on the number of carbon atoms in the acyclic ether, no structural limitation on either ether genus beyond the general acyclic or cyclic classification, no restriction on the substitution pattern of the 1,2-diketone, no quantitative limitation on the cyclic ether, and no limitation on wavelength, temperature, reaction time, light intensity, or other conditions necessary to obtain the recited 1,3-disubstituted bicyclo[1.1.1]pentane. Claims 2–7 narrow certain individual variables but retain broad combinations of the remaining genera.
The specification must enable the full scope of the claimed invention, although a reasonable amount of experimentation is permitted. Whether the required experimentation is reasonable or undue is determined by considering the factors set forth in In re Wands, 858 F.2d 731, 737, 8 USPQ2d 1400, 1404 (Fed. Cir. 1988). Those factors include the breadth of the claims, nature of the invention, state of the prior art, level of ordinary skill, predictability of the art, amount of direction provided, existence of working examples, and quantity of experimentation required. No one factor is dispositive, and the evidence must be considered as a whole. MPEP §§ 2164.01(a), 2164.06, and 2164.08.
1. Breadth of the claims
Claim 1 encompasses at least three interacting chemical genera:
Every acyclic ether solvent having five or more carbon atoms, without an upper carbon-number limit;
Every cyclic ether compound, without limitation as to ring size, number of ether oxygen atoms, saturation, substitution, electronic properties, or concentration; and
Every 1,2-diketone compound capable of being characterized as containing adjacent carbonyl groups.
The specification defines “diacetyl compound” broadly to include not only 2,3-butanedione but substituted forms in which hydrogen atoms are replaced and structures containing unsaturation, cyano groups, rings, halogens, heteroatoms, and other substituents. Paragraphs [0014]–[0018] and the structures shown on pages 5–7 illustrate a structurally diverse group of aliphatic, aromatic, cyclic, unsaturated, halogenated, heteroatom-containing, and polyfunctional diketones and glyoxylic-acid derivatives.
The acyclic-ether genus is even less structurally defined. Paragraph [0011] identifies CPME and MTBE as preferred species, but claim 1 covers all acyclic ethers having five or more carbon atoms, including linear, branched, symmetrical, unsymmetrical, monoether, polyether, substituted, and high-molecular-weight species. The claim contains no upper carbon limit and does not require that the acyclic ether have solvent properties, polarity, viscosity, transparency, or chemical compatibility comparable to CPME or MTBE.
Paragraph [0019] likewise identifies numerous cyclic ethers, including THF, 2-methyl-THF, 2,5-dihydrofuran, deuterated THF, substituted THF compounds, tetrahydropyran compounds, furan, and 1,4-dioxane. Claim 1 is not restricted to those preferred species and encompasses cyclic ethers having materially different ring sizes, substitution patterns, electron-donating properties, photochemical behavior, and reactivity.
The number of possible combinations obtained by selecting one member from each of these broad genera, and then selecting concentrations and photochemical conditions, is exceptionally large. The disclosure does not identify a common structural or mechanistic property permitting the skilled artisan to determine prospectively which combinations will produce the claimed BCP product.
2. Nature of the invention
The claimed invention concerns a multicomponent photochemical organic reaction. The reaction depends upon light-induced cleavage or excitation of a 1,2-diketone, interaction of the resulting active species with strained [1.1.1]propellane, and the influence of both an acyclic ether solvent and a cyclic ether component on the reaction.
The specification acknowledges that the reason the cyclic ether allegedly promotes the reaction “is not clear” and merely proposes that active species formed by light-induced cleavage of the diketone may be stabilized by the cyclic ether. The specification further characterizes the alleged promoting effect as “unique” to cyclic ethers and states that various noncyclic additives did not provide the same effect. Paragraph [0019].
Accordingly, the invention is not merely the performance of a well-characterized mechanical step or the substitution of components known to be interchangeable. It involves interacting photochemical, electronic, solvent, and molecular-structure effects. Changes in the diketone, acyclic solvent, cyclic ether, concentration, or irradiation conditions may affect excitation, bond cleavage, radical stability, solubility, competing reactions, and product formation. The nature of the invention therefore requires meaningful guidance concerning which combinations are operative and how operative conditions are selected.
3. State of the prior art
The state of the prior art weighs partly in favor of enablement because the general reaction of [1.1.1]propellane with certain 1,2-diketones was known. Paragraph [0002] acknowledges prior photoreactions using 2,3-butanedione and certain glyoxylic-acid compounds, and paragraph [0013] states that methods of preparing [1.1.1]propellane were known.
The known existence of the basic propellane/diketone photoreaction, however, does not establish that every claimed diketone can be reacted in every claimed acyclic ether in the presence of every claimed cyclic ether. The alleged contribution described in the specification is the particular interaction between the acyclic ether solvent and cyclic ether additive. The specification states that the promoting mechanism is unclear and that the effect is unique. The prior art therefore does not supply the missing general correlation between chemical structure and successful operation throughout the claimed three-genus combination.
4. Level of ordinary skill in the art
The level of ordinary skill is relatively high. A person of ordinary skill would be expected to have knowledge of synthetic organic chemistry and photochemistry and would understand conventional solvent selection, photoreactor operation, analytical measurement, and routine adjustment of reagent ratios, concentrations, reaction times, and temperatures.
This factor favors enablement to some extent because such a person could reproduce the specifically disclosed examples and could conduct additional screening. A high level of skill, however, does not provide the undisclosed relationship between the structures of the diketone, acyclic ether, and cyclic ether and the operability of the resulting photoreaction. Nor does skill in the art eliminate the need to determine experimentally which members of the claimed genera are mutually compatible and which wavelength and reaction conditions are effective for each combination.
5. Predictability of the art
The level of predictability weighs against enablement. Photochemical reactions generally depend on the absorption characteristics and excited-state behavior of the irradiated molecule, and solvent and additive effects may depend on polarity, donor ability, steric properties, hydrogen-atom transfer, quenching, and stabilization of transient intermediates.
The application itself supplies evidence of unpredictability. Paragraph [0019] states that the mechanism of the cyclic-ether effect is unclear and that the effect was not observed for various other additives. Comparative Examples 3–10 replace THF with ethyl acetate, toluene, acetonitrile, or acetone, demonstrating that chemically different additives do not necessarily behave interchangeably under otherwise similar conditions. Paragraphs [0053]–[0060].
The specification does not establish that all cyclic ethers share a property that reliably produces the claimed reaction across all acyclic ethers and all diketones. It also does not establish that the broad collection of depicted diketones has sufficiently similar absorption, cleavage, and propellane-addition behavior to permit the results obtained with unsubstituted 2,3-butanedione to be extrapolated throughout that genus.
In chemical arts involving unpredictable reaction behavior, disclosure of a limited number of species does not necessarily support a broad genus when the skilled artisan cannot readily anticipate the effects of structural changes.
6. Amount of direction or guidance provided
The specification provides useful guidance for a narrow set of preferred embodiments. Paragraph [0011] prefers CPME or MTBE as the acyclic ether. Paragraph [0019] prefers THF compounds and especially THF or 2-methyl-THF, and provides preferred cyclic-ether concentrations. Paragraph [0022] prefers irradiation at 300–500 nm, more preferably 320–450 nm, and still more preferably 340–430 nm. Paragraphs [0024]–[0027] provide general reaction configurations, temperatures, times, reagent ratios, and concentrations.
The specification does not, however, provide:
Criteria for selecting an operative acyclic ether other than carbon count;
Criteria for determining whether a particular cyclic ether will promote or permit the reaction;
Criteria correlating diketone structure with an effective irradiation wavelength;
Guidance for selecting cyclic-ether concentration for structurally different cyclic ethers;
Guidance for compensating for absorption, quenching, solubility, or side-reaction differences;
Examples demonstrating that the reaction can be extrapolated to glyoxylic-acid compounds or the numerous substituted diketones depicted in the specification; or
A screening protocol or structural rule that distinguishes operative from inoperative combinations.
The disclosure therefore provides detailed instructions for reproducing the preferred examples, but not a general teaching enabling the skilled artisan to traverse the full claimed scope without extensive empirical investigation.
7. Existence and scope of working examples
The specification contains multiple working examples, which weighs in favor of enablement for the subject matter actually demonstrated. The examples, however, occupy a narrow portion of the claimed scope.
Examples 1–24 use:
One 1,2-diketone: 2,3-butanedione;
Two acyclic ethers: CPME and MTBE, each used with n-hexane;
Two cyclic ethers: THF and 2-methyl-THF; and
Three irradiation wavelengths: 365, 385, and 405 nm.
Examples 1–8 vary THF concentration in CPME/n-hexane or MTBE/n-hexane. Examples 9–16 substitute 2-methyl-THF and vary its concentration. Examples 17–24 use the same basic reactant and solvent systems at 405 or 365 nm. Paragraphs [0031]–[0050].
No working example uses:
An acyclic ether other than CPME or MTBE;
A cyclic ether other than THF or 2-methyl-THF;
A substituted diacetyl compound;
A glyoxylic-acid compound;
Any of the numerous diverse diketone structures depicted in paragraphs [0015]–[0018];
Irradiation near either 200 nm or 600 nm; or
A reaction temperature approaching either −50°C or 50°C.
The rejection is not based merely on the absence of an example for every species. Rather, the examples are narrowly concentrated in a small structural area, while the specification admits that the mechanism is unclear and provides no demonstrated general property that permits the results to be extrapolated across the broad interacting genera.
8. Quantity of experimentation required
The quantity and nature of the experimentation necessary to practice the full scope of the claims weigh strongly against enablement.
For an untested embodiment, the skilled artisan would need to:
Select a particular 1,2-diketone from the broadly defined and structurally diverse genus;
Determine its absorption characteristics and an effective irradiation wavelength;
Select an acyclic ether having at least five carbon atoms in which the reactants remain soluble and chemically stable;
Select a cyclic ether that does not quench or otherwise interfere with the excited state or reactive intermediate;
Determine an effective cyclic-ether concentration;
Adjust the propellane/diketone ratio, reaction temperature, residence time, light intensity, and flow or batch conditions;
Conduct the reaction and determine whether the desired 1,3-disubstituted BCP is formed;
Identify and address competing reactions or decomposition; and
Repeat the screening for other members and combinations of the three genera.
The work required is not merely optimization of parameters after the specification has identified an operative class. It is a substantial combinatorial screening program necessary to determine which combinations are operative in the first instance. Because the specification provides no reliable structure-function relationship or general selection rule, unsuccessful results would not direct the artisan toward the next likely operative combination. The artisan would instead be required to proceed largely by trial and error.
Although routine experimentation may be extensive without necessarily being undue, the required experimentation here is disproportionate to the guidance provided and must be repeated across a very large number of structurally and photochemically different combinations. The more that is claimed, the more must be enabled, and a specification claiming an entire class must permit the skilled artisan to make and use that class rather than merely a narrow subset.
Application to the individual claims
Claim 1 is not enabled throughout its full scope because it encompasses all acyclic ethers having at least five carbon atoms, all cyclic ethers, and all 1,2-diketones without providing sufficient guidance to select operative combinations. The specification reasonably enables the disclosed CPME or MTBE/THF or 2-methyl-THF/2,3-butanedione embodiments, but not the full three-genus combination.
Claim 2 limits the acyclic ether to 5–10 carbon atoms. This excludes higher-carbon ethers but still encompasses numerous linear, branched, symmetrical, unsymmetrical, monoether, and polyether structures. Claim 2 retains unrestricted 1,2-diketone and cyclic-ether genera and therefore does not overcome the enablement deficiency.
Claim 3 limits the acyclic ether to five or six carbon atoms. The claim remains broader than CPME and MTBE and continues to encompass multiple structurally and electronically different ether species in combination with unrestricted 1,2-diketone and cyclic-ether genera. The specification provides no basis for concluding that carbon count alone determines operability.
Claim 4 limits the diketone to a diacetyl compound or glyoxylic-acid compound. Paragraph [0014] defines “diacetyl compound” broadly to encompass numerous substituted structures, and paragraphs [0015]–[0018] depict a diverse collection of species. The working examples use only unsubstituted 2,3-butanedione and provide no actual example involving a glyoxylic-acid compound or substituted diacetyl compound. Claim 4 also retains the broad acyclic-ether and cyclic-ether genera.
Claim 5 limits the cyclic ether to a tetrahydrofuran compound. The specification demonstrates THF and 2-methyl-THF, but “tetrahydrofuran compound” encompasses numerous substituted THF species, including unsaturated, halogenated, deuterated, hydroxy-substituted, and other derivatives identified in paragraph [0019]. Claim 5 retains the unrestricted acyclic-ether and 1,2-diketone genera, and no guidance establishes that every THF derivative behaves like THF or 2-methyl-THF.
Claim 6 requires irradiation with light having a wavelength of 200–600 nm. Paragraph [0022] directs the skilled artisan toward a materially narrower preferred region of 300–500 nm, more preferably 320–450 nm, and still more preferably 340–430 nm. The examples test only 365, 385, and 405 nm. The specification provides no guidance demonstrating that irradiation near 200 nm or 600 nm will initiate the required photoreaction for the full claimed diketone genus or explaining how to select an operative wavelength for structurally different diketones.
Claim 7 limits the reaction temperature to −50°C to 50°C. Although paragraph [0025] identifies that range and narrower preferred ranges, the working examples do not demonstrate operation throughout the range. More importantly, claim 7 retains the unrestricted acyclic-ether, cyclic-ether, and diketone genera of claim 1. The temperature limitation therefore does not resolve the need for undue experimentation to identify operative chemical combinations.
Conclusion
Considering the Wands factors as a whole, the breadth of the interacting chemical genera, the photochemical and solvent-dependent nature of the reaction, the admitted uncertainty regarding the mechanism, the absence of a demonstrated structure-function correlation, the narrow concentration of the working examples, and the extensive combinatorial screening required establish a reasonable basis to conclude that claims 1–7 are not enabled throughout their full scope.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -6:30 pm).
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/DEBORAH D CARR/ Primary Examiner, Art Unit 1691
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