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 .
Status of Claims
Claims 1, 2, 4, 7, 10-16, 18, 20 – 22, 24, 26 and 28 – 30 are pending.
Claims 1, 2, 4, 7, 10-16, 18, 20 – 22, 24, 26 and 28 – 30 are rejected.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 20 and 24 are rejected under 35 U.S.C. 112(d), as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 20 recites the limitation "R is selected from… a methoxyethyl group" in line 2. There is insufficient antecedent basis for this limitation in the claim because the methoxyethyl group is a substituted alkyl. Claim 1 recites; “each R is, independently, a linear or branched alkyl, alkenyl, or alkynyl group containing 1 to 12 carbon atoms”. Claim 1 does not mention an optional substitution of the alkyl, alkenyl, or alkynyl group containing 1 to 12 carbon atoms. Specifically, the Markush listing for claim 1 does not include alkoxyalkyl, such as the moiety methoxyethyl recited by claim 20. Therefore, claim 20 fails to further limit claim 1. This rejection may be overcome by amending claim 1 to specify that R can be optionally substituted with an alkoxide. See paragraph [0018] of the specification.
Claim 24 recites the limitation "each R is a 2-methoxyethyl group" in line 1. There is insufficient antecedent basis for this limitation in the claim because the 2-methoxyethyl group is a substituted alkyl. Claim 1 recites; “each R is, independently, a linear or branched alkyl, alkenyl, or alkynyl group containing 1 to 12 carbon atoms”. Claim 1 does not mention an optional substitution of the alkyl, alkenyl, or alkynyl group containing 1 to 12 carbon atoms. Specifically, the Markush listing for claim 1 does not include alkoxyalkyl, such as the moiety methoxyethyl recited by claim 24. Therefore, claim 24 fails to further limit claim 1. This rejection may be overcome by amending claim 1 to specify that R can be optionally substituted with an alkoxide. See paragraph [0018] of the specification.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1, 2, 4, 10, 12, 15, 16, 20 – 22 and 24 is/are rejected under 35 U.S.C. 103 as being unpatentable over Schrader et al. (US 2,130,038) in view of Sherman et al. (Product Class 12: N-alkylsulfamic acids and derivatives, Science of Synthesis, 2009, 40b, pp. 1286) and further in view of Singh et al. (WO 2014/035464).
The rejected claim covers, inter alia, method of producing a sulfamoyl fluoride compound of the formula F SO2NR2, wherein either 1) each R is, independently, a linear or branched alkyl, alkenyl, or alkynyl group containing 1 to 12 carbon atoms or 2) R2 forms a cyclic amine with the N, the method comprising: adding a sulfamoyl nonfluorohalide of the formula X SO2NR2 and hydrogen fluoride (HF) to a reaction chamber of a reaction apparatus, wherein X is selected from the group consisting of chlorine (Cl), bromine (Br), and iodine (I);providing conditions sufficient to support a reaction between the sulfamoyl nonfluorohalide and the HF that forms the sulfamoyl fluoride compound and an HX byproduct; and selectively removing at least some of the HX byproduct so as to yield the sulfamoyl fluoride compound.
Dependent claims 2 and 4 further limit the reaction conditions. Dependent claim 10 limits the HF to the sulfamoyl nonfluorohalide. Dependent 12 claim limits the product yield to 85%. Dependent claims 15 and 16 further limit the reaction to include the presence of a catalyst and one comprised of a Bi(III). Dependent claims 20 – 22 and 24 further limit R in the formula.
However, Schrader discloses the method for preparing the sulphamic acid fluorides of the formula
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, wherein R1 and R2 may stand for “methyl, ethyl, propyl, hexyl and dodecyl” and “alkyl radicals which are substituted , for instance, by halogen atoms or the amino, cyano, mercapto, alkoxy, carboxylic acid, carboxylic acid ester, sulfonic acid or aryl group”. (pp. 1, left col. ln 4 – 10 & 24 – 31). The preparation involves reacting upon sulphamic acid chlorides of the general formula
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100
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with soluble metallic fluorides in the presence of a solvent or a liquid diluent. (pp. 1, left col. ln 15 – 23). Examples of metallic fluorides includes “potassium, sodium, ammonium, zinc and silver fluorides. (pp. 1, rt. col. ln 52 – 55). Example 1 of Schrader discloses the following:
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(pp. 2, left col. ln 19 – 37). Also, the reaction can be carried out at temperatures between 70°C - 100°C. (col. 2, ln 4 – 5).
The difference between the instantly claimed invention and Schrader is as follows: adding hydrogen fluoride to the sulphamic acid chlorides; the HF is at least about 1.5 equivalents relative to the sulfamoyl nonfluorohalide (claim 10); and the reactants comprise a catalyst and a catalyst comprised of Bi(III) (claims 15 and 16).
However, with regard to adding hydrogen fluoride to the sulphamic acid chlorides the Examiner turns to the teaching of Sherman. The prior art of Sherman discloses making alkylsulfamoyl halides. Sherman’s Product Subclass 1 Variation 3: N-Alkylsulfamoyl chlorides can be converted into the corresponding N-alkylsulfamoyl
fluorides by reaction with an appropriate fluoride source. This reaction has been per-
formed with hydrogen fluoride, [11] sodium fluoride, [12] potassium fluoride, [13] or antimony(III) fluoride (Scheme 3). The conditions necessary to effect the transformation are dependent on the substrates used but generally include an excess of the fluoride source and elevated temperatures. (pp. 1286).
Because each of the references teach methods for preparing sulphamic acid fluorides from sulphamic acid chlorides, it would have been obvious to one skilled in the art to substitute the hydrogen fluoride of Sherman for the potassium fluoride in the process of Schrader to achieve the predictable result of producing the alkysulfulfamoyl fluoride. Motivation can be found in Schrader and Sherman. Schrader states that instead of potassium fluoride, sodium may be used with the same success. (pp. 2, left col. ln 37 – 38). Sherman states that the reaction can take place with the appropriate fluoride source, wherein, the interchangeable fluoride sources are hydrogen fluoride, sodium fluoride, potassium fluoride, or antimony(III) fluoride. (pp, 1286).
Therefore, the claims would have been obvious because the substitution of one known element for another would have yielded predictable results to one of ordinary skill in the art at the time of the invention. (KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (U.S. 2007)).
Regarding the HF is at least about 1.5 equivalents relative to the sulfamoyl nonfluorohalide (claim 10), the Examiner turns to the teaching of Schrader in view of Sherman. The prior art of Sherman discloses making alkylsulfamoyl halides. Sherman’s Product Subclass 1 Variation 3: N-Alkylsulfamoyl chlorides can be converted into the corresponding N-alkylsulfamoyl fluorides by reaction with an appropriate fluoride source. This reaction has been performed with hydrogen fluoride, [11] sodium fluoride, [12] potassium fluoride, [13] or antimony(III) fluoride (Scheme 3). In Example 1 of Schrader potassium fluoride s added at least about a 1.43 equivalents relative to the dimethyl sulphamic acid chloride. As such, based on the teaching of Schrader and Sherman, a person of ordinary skill in the art at the time of the instantly claimed invention, can easily obtain the required HF to sulfamoyl nonfluorohalide required for the reaction by routine experimentation. Where the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Regarding the reactants comprise a catalyst and a catalyst comprised of Bi(III) (claims 15 and 16), the Examiner turns to the teachings of Sherman and Singh. The prior art of Sherman teaches that N-Alkylsulfamoyl chlorides can be converted into the corresponding N-alkylsulfamoyl fluorides by reaction with an appropriate fluoride source; such as, hydrogen fluoride, sodium fluoride, potassium fluoride, or antimony(III) fluoride. Singh discloses a method for producing a fluorinated compound of the formula:
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by contacting a nonfluorohalide compound of the formula:
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with bismuth trifluoride (BiF3) under conditions sufficient to produce the fluorinated compound of Formula I. (pp. 4, [0014]).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the instantly claimed invention substitute the potassium fluoride of Schrader with HF of Sherman and then include an additional fluorinating agent to act as a catalyst such as BIF3 of Singh in order to increase the rate of reaction so that the reaction proceeds more quickly. Motivation can be found in the desire to make the process cheaper, cleaner, faster, lighter, smaller, more durable, or more efficient. Because the desire to enhance commercial opportunities by improving a product or process is universal-and even common-sensical, we have held that there exists in these situations a motivation to combine prior art references even absent any hint of suggestion in the references themselves. (DyStar Textilfarben GmbH & Co. Deutschland KG v. C.H. Patrick Co., 464 F.3d 1356, 1366, 1368; 80 USPQ2d 1641, 1649, 1651 (Fed. Cir. 2006)).
Therefore, all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art before the effective filing date of the instantly claimed invention. KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (U.S. 2007).
Claim Rejections - 35 USC § 103
Claim(s) 1, 2, 4, 7, 10 – 12, 21, 22 and 26 are rejected under 35 U.S.C. 103 as being unpatentable over Farbenfabrikent Bayer Aktiengesellschaft (GB 1264774) (Bayer).
The rejected claim covers, inter alia, method of producing a sulfamoyl fluoride compound of the formula F SO2NR2, wherein either 1) each R is, independently, a linear or branched alkyl, alkenyl, or alkynyl group containing 1 to 12 carbon atoms or 2) R2 forms a cyclic amine with the N, the method comprising: adding a sulfamoyl nonfluorohalide of the formula X SO2NR2 and hydrogen fluoride (HF) to a reaction chamber of a reaction apparatus, wherein X is selected from the group consisting of chlorine (Cl), bromine (Br), and iodine (I);providing conditions sufficient to support a reaction between the sulfamoyl nonfluorohalide and the HF that forms the sulfamoyl fluoride compound and an HX byproduct; and selectively removing at least some of the HX byproduct so as to yield the sulfamoyl fluoride compound.
Dependent claims 2 and 4 further limit the reaction conditions. Dependent clam 7 further limits the method of adding reactants. Dependent claims 10 – 11 further limit the HF to the sulfamoyl nonfluorohalide. Dependent 12 claim limits the product yield to 85%. Dependent claims 21 – 22 further limit R in the formula. Dependent claim 26 further limits the HX.
However, Bayer discloses reaction of 247g N,N-dimethylsulfamic acid chloride with 160 ml of hydrogen fluoride (drop wise addition) for 4 hours at 80 to 90°C. After distillation 195 g of N,N-dimethylsulfamic acid fluoride are obtained, which correspond to a yield of 89% (see example 6). (pp. 4). The apparatus is described in Example 1 as consisting of a pressure vessel, a Liebig condenser and an exhaust-gas valve. (pp. 3). The general reaction of the sulphamic acid chlorides with anhydrous hydrogen fluoride can be carried out by mixing the reagents, preferably in a molar ratio of rom 1:1 to 1:4. (pp. 1, rt col. ln 75 – 80). The hydrogen chloride formed is vented in batches through a valve. Finally, more of the excess hydrogen fluoride is removed in vacuo. (pp. 2, left col. ln 1 – 3). Further, even though Bayer does not explicitly disclose condensation of the by product HX, this would happen under the reaction conditions of Example 6.
The difference between Bayer and the claimed invention is that it does not teach the invention with particularity so as to amount to anticipation (See M.P.E.P. §2131: "[t]he identical invention must be shown in as complete detail as is contained in the ...claim." Richardson v. Suzuki Motor Co., 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990).).
However, based on the above, Bayer teaches the elements of the claimed invention with sufficient guidance, particularity, and with a reasonable expectation of success, that the invention would be prima facie obvious to one of ordinary skill (the prior art reference teaches or suggests all the claim limitations with a reasonable expectation of success. (see M.P.E.P. § 2143).
Claim Rejections - 35 USC § 103
Claim(s) 1, 2, 4, 7, 10 -16, 18, 20 – 21, 25 and 28 – 30 are rejected under 35 U.S.C. 103 as being unpatentable over Ignat’ev et al. (Journal of Fluorine Chemistry, 1995) in view of Poshusta et al. (US 2015/0126778).
The rejected claim covers, inter alia, method of producing a sulfamoyl fluoride compound of the formula F SO2NR2, wherein either 1) each R is, independently, a linear or branched alkyl, alkenyl, or alkynyl group containing 1 to 12 carbon atoms or 2) R2 forms a cyclic amine with the N, the method comprising: adding a sulfamoyl nonfluorohalide of the formula X SO2NR2 and hydrogen fluoride (HF) to a reaction chamber of a reaction apparatus, wherein X is selected from the group consisting of chlorine (Cl), bromine (Br), and iodine (I);providing conditions sufficient to support a reaction between the sulfamoyl nonfluorohalide and the HF that forms the sulfamoyl fluoride compound and an HX byproduct; and selectively removing at least some of the HX byproduct so as to yield the sulfamoyl fluoride compound.
Dependent clams 2, 4, 7, 10 -16, 18, 20 – 21, 25 and 28 – 30 further limit the reactants and process.
However, Ignat’ev discloses that N,N-Dimethylamidosulfonyl chloride (6) was yielded under similar conditions a crude product with a GC composition nearly identical to fractions derived from the ECF (electrochemical fluorination) of compound 1, wherein according to the process of the ECF of compound 1, N,N-Dimethylamidosulfonyl fluoride was added to 500ml of anhydrous HF in the ECF cell; electrolysis was complete after passage of 250Ah through the cell; from the cooling traps, a crude product was obtained, which was distilled to give five fractions, wherein according to GC, fraction (i) consisted mainly (85%-90%) of compound 2((CF3)2NSO2F), fraction (ii) of 2((CF3)2NSO2F)(32%) and 3(CF3(CHF2)NSO2F)(53%). fraction (iii) of 3(CF3(CHF2)NSO2F)(85%) and 4((CHF2)2NSO2F) (10%), fraction (iv) of 3(CF3(CHF2)NSO2F)(40%) and 4((CHF2)2NSO2F)(50%), and fraction (v) of 4((CHF2)2NSO2F)(75%) and compounds 2-4 were separated in more than 95% concentration by further distillation (see page 183, 3.1 ECF of compound 1; table 1).
The compound (6) is identical to sulfamoyl nonfluorohalide in claims 1, 20 and 21 of the instantly claimed invention when X = Cl, R2 = linear alkyl (methyl).
The difference between Ignat’ev and the instantly clamed invention is as follows: Claims 1, 20 and 22 differ from Ignat’ev (1) converting only non-fluorohalogen(X) bonded to SO2 to fluorine(F) by the chemical reaction and (2) forming an HX.
Regarding (1) converting only non-fluorohalogen(X) bonded to SO2 to fluorine(F) by the chemical reaction. This different feature would be derived by controlling reaction conditions if necessary by a person skilled in the art considering the compounds 2-4 having F-CO2-N structure prepared by the chemical reaction of the compound 6 having Cl-SO2-N structure and HF in Ignat’ev (page 183, 3.1 ECF of compound 1; table 1).
With regard to (2) forming an HX, the Examiner turns to the teaching of Poshusta. The prior art of Poshusta discloses a method comprising reacting a non-fluoro halogenated trihalomethylsulfonyl imide compound with hydrogen fluoride, wherein said reacting step also produces HX1, HX2, or a combination thereof (X1 is non-fluoro halide; X2 is halide), and wherein said step also comprises removing HX1, HX2 or a combination thereof that is produced in the reaction (see claims 1-3; paragraphs [0050], [0051]).
Considering that Ignat’ev and Poshusta are in the same technical field relating to the preparation of compound having F-SO2-N structure from CI-SO2-N structure, a person skilled in the art before the effective filing date of the instantly claimed invention, would easily arrive at the claims by combining Ignat’ev and Poshusta without difficulty and the effect of them would be predictable.
Therefore, all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art before the effective filing date of the instantly claimed invention. KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (U.S. 2007).
Regarding claim 2, the additional feature would have been derived by a person skilled in the art, before the effective filing date of the instantly claimed invention, in view of Poshusta in hydrogen refluxing condition. (claim 4, para. [0011]).
With regard to claim 4, would be appropriately modified or optimized through repeated experimentation by a person skilled in the art, before the effective filing date of the instantly claimed invention, considering Poshusta in that the reaction temperature is at least 30°C (para. [0013]).
Regarding claim 7, would be derived by a person skilled in the art, before the effective filing date of the instantly claimed invention, considering Poshusta in adding HF batch-wise (para. [0033]).
Regarding claims 10 and 11, would be appropriately modified or optimized through repeated experimentation by a person skilled in the art, before the effective filing date of the instantly claimed invention, considering Poshusta in that at least 2 equivalent of total hydrogen fluoride relative to non-fluoro halogenated trihalomethylsulfonyl imide compound is added to the reaction (claim 8; para. [0014]).
With regards to claims 12 – 14, it would have been obvious to a person skilled in the art that the yield of the resulting product would be controlled by routine experimental means. Where the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Regarding claim 15, would be derived by a person skilled in the art, before the effective filing date of the instantly claimed invention, considering Poshusta in that reaction condition comprises the presence of a catalyst (claim 10; para [0016]).
With regard to claim 16, it would be derived by a person skilled in the art, before the effective filing date of the instantly claimed invention, considering Poshusta in a Bi(III) compound (BiF3) as the catalyst (para. [0037]).
Regarding claim 18, would be appropriately modified or optimized through repeated experimentation by a person skilled in the art, before the effective filing date of the instantly claimed invention, considering Poshusta in that a catalyst is used, typically about 0.5 equivalent or less (para. [0038]). Where the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Regarding claim 26, it would be derived by a person skilled in the art, before the effective filing date of the instantly claimed invention, considering Poshusta in that HX1 and HX2 are typically gases and HX1 and HX2 can be removed from the reaction mixture by distillation or evaporation (para, [0029]).
With regard to claim 28, it would be derived by a person skilled in the art, before the effective filing date of the instantly claimed invention, considering Poshusta in that any HF that may evaporate or distill can be condensed and returned back into the reaction (para.[0029]).
Regarding clam 29, it would be derived by a person skilled in the art considering Poshusta in that a continuous stirred tank reactor (CSTR) is advantageous as it allows HF refluxing and continuous HCI removal (para. [0048]).
Regarding claim 30, it would be derived by a person skilled in the art, before the effective filing date of the instantly claimed invention, considering Poshusta in that any unreacted XTXSI and HF that may be present can be recycled back into the reactor (para. [0043]).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to YATE' K. CUTLIFF whose telephone number is (571)272-9067. The examiner can normally be reached Monday-Friday (8:30 - 5:30).
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/YATE' K CUTLIFF/Primary Examiner, Art Unit 1692
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