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.
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.
Claims 1-8, and 11-19 are rejected under 35 U.S.C. 103 as being unpatentable over Gao et al (CN 103265403 A).
Applicants’ claimed invention is directed to a method for producing a fluorine-containing compound, the method comprising: reacting a compound having a partial structure represented by the following formula (a) with a Grignard reagent in the presence of a transition metal compound:
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Ra is a fluorine atom or a fluoroalkyl group, Rb is a hydrogen atom or a fluoroalkyl group, and L is a sulfonate group.
Regarding claim 1, Gao teaches reacting a compound with a Grignard reagent and a transition metal catalyst. The starting material, 2,2,2-trifluoroethyl mesylate, maps directly to formula (a). in this instance, Ra is a fluoroalkyl group (the -CF3 radical), Rb is a hydrogen atom, and L is mesylate group, which represents a valid, recognized species of the broader sulfonate group genus. See paragraphs 0023-0024, 0028 and claims.
Regarding claim 2, this claim relies on alternative language (a Markush grouping) specifying that G1 can be a hydrogen atom. The 2,2,2-trifluoroethyl mesylate structure utilized by Gao Mirrors formula (A1) where Ra=H, Rb=CF3 and G1=H. See paragraphs 0018, 0070, examples and claims.
Regarding claim 3, Gao explicitly discloses reacting 2,2,2-trifluoroethyl mesylate with a Grignard reagent. The structural formula 2,2,2-trifluoroethyl mesylate is CF3-CH2-OMs (OMs is the mesylate sulfonate leaving group). If a person having ordinary skill in the art, prior to the effective filing date of the claimed invention select the perfluoroalkyl group alternative for G1 in claim 3, the following structural assignments the parent claim parameters apply:
Set G1 to a trifluoromethyl group (-CF3), which is the fundamental baseline perfluoroalkyl group.
Set Ra to a hydrogen atom
Set Rb to a hydrogen atom
Set L to a mesylate group (which is valid sulfonate group).
Because a trifluoromethyl group (-CF3) is a well-known, universally recognized member of the broader perfluoroalkyl group genus, this specific alternative path of claim 3 duplicates the exact chemical structure disclosed in Gao. See paragraphs 0018, 0070, examples and claims.
A chemist looking to perform cross-coupling displacements on a fluorinated alkyl sulfonate substrate is explicitly directed by Gao to use a starting material containing a trifluoromethyl group. Selecting s starting configuration where G1 is a trifluoromethyl group (-CF3) requires no independent design or creative step; it is a direct copy of the exact reactant taught in Gao. Because this specific alternative reads directly on the prior art.
Regarding claim 4, Gao discloses reacting 2,2,2-trifluoroethyl mesylate group leaves and a carbon-carbon single bond is produced In formula (A2) of the present application, if G2 is selected as the alternative “a single bond,” the resulting chemical structure directly reads on the reaction of 2,2,2-trifluoroethyl mesylate as disclosed in Gao et al. See paragraphs 0018, 0070, examples and claims.
Regarding claim 11 depends on claim 1 and specifies that the transition metal compound contains copper. Gao explicitly discloses a method for manufacturing a fluorine-containing compound by reacting a fluorinated alkyl sulfonate with a Grignard reagent in the explicit presence of a copper-containing compound as the catalyst. Therefore, the catalyst limitation introduced in claim 11 is directly taught by the prior art.
Regarding claims 5-8 Gao explicitly discloses manufacturing 2-(4,4,4-trifluoroethyl mesylate with a Grignard reagent in the presence of a copper-containing compound. The Grignard reagent used in Gao’s primary synthesis react with fluorinated substrate to add the organic group. Where R is an alkyl or aryl group and X is Cl, Br, or I represent the universal, standard configuration of Grignard coupling reaction. See paragraphs 0018, 0070, examples and claims.
A person having ordinary skill in the art, prior to the effective filing date of the claimed invention seeking to create carbon-carbon single bond using the method of claim 1 would be directly motivated to choose a Grignard reagent of formula R-MgX where R is hydrocarbon Group. This choice represents the direct application of standard organic chemistry building blocks.
Regarding claim 6 and 12 depends on claim 2, uses alternative (Markush) language for G1, explicitly including the alternative where G1 is a hydrogen atom, the same starting matches the 2,2,2-trifluoroethyl mesylate used in Gao. By adding the limitation of a standard hydrocarbon Grignard reagent (R-MgX) in claim 6, this dependent claim continues to read directly on the baseline cross coupling reaction disclosed in Gao. See paragraphs 0018, 0070, examples and claims.
The chemist is motivated to select a basic hydrocarbon-based Grignard reagent because it represents the most fundamental, low-cost class of nucleophiles used to displace sulfonate leaving group. Because this specific structural alternative path of claim 6 completely overlaps with the established disclosure of Gao.
Regarding claim 13 and 14 Gao explicitly discloses reacting 2,2,2-trifluoroethyl mesylate with a Grignard reagent in the presence of a copper catalyst.
The structural mapping to formula (A1): the starting material in Gao matches formula
(A1): G1-C(-Ra)(-Rb)-CH2-L
If G1 is hydrogen: the structure matches Gao where Ra =H, Rb=CF3. See paragraphs 0018, 0070, examples and claims.
Regarding claim 14, Gao explicitly discloses reacting 2,2,2-trifluoroethyl mesylate with a Grignard reagent. CF3 CH2-OMs onto formula A1, it fits formula A1.
Regarding claim 15 if G2 is a single bond, formula (A2) collapses into a continuous chain of repeating fluorinated carbons connected directly, with leaving group (L) at the terminals.
Regarding claim 17, Gao explicitly discloses manufacturing 2-(4,4,4-trifluorobutoxy)tetrahydro-2H-pyran. The compound produced in Gao is formed by reacting 2,2,2-trifluoroethyl mesylate with a specific ether containing Grignard reagent. The final molecular skeleton of this product can be written out as:
CF3-CH2-CH2-CH2-CH2-O-THP
Set G1 to the alternative a (-H)
Set Ra to the alternative a fluoroalkyl group (-CF3)
Set Rb to the alternative : a (-H)
Set R to the alternative: a hydrocarbon group containing a heteroatom -(CH2CH2CH2-O-THP).
Formula (C1) collapses exactly into:
H-C(-CH3)(-H)-XH2-CH2-CH2-CH2-O-THP. See paragraphs 0018, 0070, examples and claims.
Regarding claim 18, if we select the perfluoroalkyl group alternative for G1 in claim 18, we can choose the following structure assignments from the parent claim parameters:
Set G1 to a trifluoromethyl group (-CF3)
Set Ra to (-H)
Set Rb to a (-H)
Set R to a standard substituted hydrocarbon chain (-CH2CH2CH2-O-THP). Because a trifluoromethyl group (-CF3) is a well-known, recognized member of the broader perfluoroalkyl group genus, this specific alternative path of claim 18 duplicates the exact chemical composition disclosed in Gao.
Regarding claim 19, when n=0 within claim 19, the entire structural block bracketed by {-}n disappears completely from formula (C2).
Formula (C2) collapse into:
R-CH2-C(Ra)(Rb)-CH2-R
Gao explicitly teaches reacting a fluorinated alkyl sulfonate substrate (2,2,2-trifluoroethyl mesylate) with an organic Grignard reagent to displace a sulfonate leaving group and form carbon-carbon single bond.
A person ordinary skilled in the art, prior to the effective filing date of the claimed invention would find that the creation of a baseline fluorinated hydrocarbon chain via Grignard reagent displacement is fully taught and enabled by Gao.
When n=1 and sets G2 to the alternative a single bond, formula (C2) becomes:
R-CH2-C(Ra)(Rb)-C(Ra)(Rb)-CH2-R, See paragraphs 0018, 0070, examples and claims.
This represents a short, contiguous fluorinated alkane backbone linked by direct carbon-carbon single bonds. Gao cross-coupling process is standard carbon-carbon single bond. A chemist seeking to couple organic components onto a fluorinated framework would naturally use standard single bonds to bridge the atoms. It represents the most basic structure connection in organic chemistry and yields no unexpected properties, rendering the choice obvious.
Claim Rejections - 35 USC § 103
Claims 9,10 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Gao et al (CN 103265403 A) as applied to claims 1,2 and 4-6 above, and further in view of Nabuaki et al (JP 2003026612).
Gao teaches the primary reaction framework of claim 1, demonstrating the cross-coupling of a fluorinated alkyl sulfonate substrate using a copper catalyst and a Grignard reagent. However, Gao specifically utilizes a mesylate (methaneslulfonate) leaving group rather than a triflate group. However, Nabuaki fills this gap by disclosing identical transition metal catalyzed Grignard cross coupling reactions to form carbon-carbon single bonds. Nabuaki explicitly teaches a triflate group serves as a highly efficient, high performance leaving group on fluorinated organic frameworks. See claims.
A person having ordinary skill in the art, before the effective filing date of the claimed invention seeking to perform the cross-coupling method of claim 1 would be highly motivated to substitute the mesylate leaving group of Gao with the triflate leaving group of claims 9,10 and 16 because the triflate behave as an exceptional super leaving group.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JAFAR F PARSA whose telephone number is (571)272-0643. The examiner can normally be reached M-F 10:00 AM-6:30PM.
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/JAFAR F PARSA/Primary Examiner, Art Unit 1692
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