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 .
Election/Restrictions
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Pending claims 1-20 are examined together.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-20 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Base claim 1:
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The structural make-up of the starting materials, reagents, catalysts and products are defined in generic umbrella terms referring to class of compounds, and thus rendering the scope, mete and bounds of the claim unclear.
This is a clarity issue and not 112-1 scope issue (which is dealt with separately, see below).
A comprehensive patent search could not be done for the base claim.
Dependent claims do not address all the issues of the base claim. For example, see claim 11, which defines the starting material as ‘agrochemical’. As such claims 2-20 are rejected as well.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-20 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for few examples for the method with respect to starting materials, reagents, catalyst and products does not reasonably provide enablement for any and all of these possibilities. For example, it is not seen where in the specification enabling disclosure is found for compounds, wherein the F in the fluorinated alcohol is not as found in claim 6. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the invention commensurate in scope with these claims..
The determination that "undue experimentation" would have been needed to make and use the claimed invention is not a single, simple factual determination. Rather, it is a conclusion reached by weighing all the relevant factual considerations.
Enablement is considered in view of the Wands factors (MPEP 2164.01 (a)). These include: (1) breadth of the claims; (2) nature of the invention; (3) state of the prior art; (4) amount of direction provided by the inventor; (5) the level of predictability in the art; (6) the existence of working examples; (7) quantity of experimentation needed to make or use the invention based on the content of the disclosure; and (8) relative skill in the art.
All of the factors have been considered with regard to the claims, with the most relevant factors discussed below:
The structural make-up of the starting materials, reagents, catalysts and products are defined in generic umbrella terms such that the scope of the claims are wide that finds little support in the specification. Fluorinated alcohols (with BRS) means any alcohol that has a Fluorine atom anywhere in the molecule. The working examples are limited to fluorinated alcohols wherein the fluorine atom(s) are flanking the alcohol containing carbon For example, there is no example wherein the fluorine substituted Cs are further away from the CHOH moiety. The claim 6 compound is the only fluorinated alcohol exemplified and is the elected species hexafluoro propanol HFIP. One of skill in the art would understand, the electron withdrawing nature of the CF3 moiety, renders this alcohol a weak nucleophile and therefore an unlikely partner in forming aryl ethers by simple nucleophilic aromatic substitution SNAr reaction. This at once raises the issue whether any and all fluorinated alcohol would provide predictable result. Given there is no other working examples, nothing in the specification teaches that for example, the C8 aliphatic alcohol, mono-fluoro-octanol would make aryl ethers. Similarly, expecting any aryl halide could be a substrate finds no support in the specification. For example, it is clear from the list of compound made with HFIP at pages 21-27, the reaction is highly dependent on the starting material aryl-halide, the nature of the halide, as well as what substituents are present on the aryl-halide. See for example last four examples on page 23. Likewise, based on the disclosure at page 24, even different position of the methoxy group in otherwise same aryl halide, results in different yield, or no yield. On top of this unpredictability, the reaction not being a simple conventional SNAr reaction in view of the high pKa of the exemplified HFIP, it is clear that the method is a catalyzed reaction (with concomitant irradiation). It is well established that catalyzed reaction is generally considered unpredictable merely from the chemical nature of the catalyst as per Corona Co. v. Dover; (USSC 1928) 276 US 358, 369. The catalytic action cannot be forecast by its chemical composition, for such action is not understood and is not known except by actual test, Corona Cord Tire Co. v. Dovan Chemical Corp., 276 U.S. 358, 368-369 (1928). Catalytic effects are not ordinarily predictable with certainty. In re Doumani et al. (CCPA 1960) 281 F2d 215, 126 USPQ 408. According to U.S. District Court District of Connecticut held in Mobil v. Grace 180 USPQ 418 “there is an inherent mystery surrounding the unpredictability of the performance of catalysts...”
The working examples serve to be opposite of the ‘direction and guidance’ needed as per 112-1. The above noted Table-4 examples are clearly suggestive of operation of process parameters in tandem, specific structures of starting materials (aryl halide) and the fluorinated alcohol, the specific catalyst and base with unpredictable results. This is consistent with art recognized capricious nature of organic chemistry. See for example, Dorwald F. A. Side Reactions in Organic Synthesis, 2005, Wiley: VCH, Weinheim pg. IX of Preface pg. 1-15. Dorwald teaches that ” …as will be shown throughout this book, the outcome of organic reactions is highly dependent on all structural features of a given starting material, and unexpected products may readily be formed. [8]……...Even the most experienced chemist will not be able to foresee all potential pitfalls of a synthesis, especially so if multifunctional, structurally complex intermediates must be prepared.…..”
There is a substantial gap between what is taught in the specification and what is being claimed. For these reasons, one skilled in the art would be faced with undue amount of research. The specification lacks disclosure sufficient to make and use the invention, in predictable manner.
MPEP 2164.01(a) states, “A conclusion of Iack of enablement means that, based on the evidence regarding each of the above factors, the specification, at the time the application was filed, would not have taught one skilled in the art how to make and/or use the full scope of the claimed invention without undue experimentation. ln re Wright, 999 F.2d 1557,1562, 27 USPQ 2d 1510, 1513 (Fed. Cir. 1993).'' That conclusion is clearly justified here. Thus, undue experimentation would be required to make and use Applicants' invention.
Suggestion:
DELETE all claims.
Format a new claim with details limiting as per [0088] at page 27.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-3, 5, 8 and 13 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Escobar, Chem. Eur. J. 2020, 26, 5168 – 517.
Escobar teaches practical Method for Carbon–Heteroatom Cross-Coupling using Nickel/Photo Dual Catalysis:
Escobar at page 5172, line 1
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(see line 6 from top of page 572)
corresponds to:
2a is aryl halide, 1x is C2-fluorinated (claim 2), 1x is 3-flourines (claim 3), 1x has one CH bond (claim 4), 2a is aryl bromide (claim 8);
Blue LED emits electromagnetic radiation in the form of visible light
is base
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pyrylium (page 5172, line 1)
3a-ba fluorinated compound with A = O; R1 = H; R=CF3
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Su, Catalytic SNAr Hexafluoroisopropoxylation of Aryl Chlorides and Bromides, Angew. Chem. Int. Ed.2023, 62, e202302908.
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Any inquiry concerning this communication or earlier communications from the examiner should be directed to NIZAL S CHANDRAKUMAR whose telephone number is (571)272-6202. The examiner can normally be reached M-F 8-5 EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Andrew Kosar can be reached at (571) 272-0913. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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(a)(1) /NIZAL S CHANDRAKUMAR/ Primary Examiner, Art Unit 1625
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