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 .
DETAILED ACTION
This Office action is responsive to Applicant's Response to Election/Restriction filed February 04, 2026. As filed, Claims 1-17 are pending.
Priority
This application, filed 05/03/2023 is a National Stage entry of PCT/EP2021/080869 , International Filing Date: 11/08/2021; claims foreign priority to 20206379.8, filed 11/09/2020.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) filed on 5/03/2023 have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
Election/Restrictions
Applicant’s election of Group I, claims 1-12 in the reply filed on Feb. 04, 2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.03(a)).
Applicant’s elect the species of the R1 of Formulas (I) and (II)= methyl group; catalyst Au complex= chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I) ; Ag(I) salt or Ag(I) complex= AgSbFG; described on Example paragraph [0103] of the specification and indicated that claims 1-3 and 5-12 read on the elected species.
Claims 13-17 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant’s election without traverse of Group II, claim 7 in the reply filed on Feb. 09, 2016 is acknowledged.
A complete response to this Office Action should include cancellation of non-elected subject matter or other appropriate action.
The instantly elected species was searched and examined. It was determined that the elected species was free of the prior art. For this reason, the search and examination was expanded within the Markush-type claims and to consider additional species and subgenera within the generic formula of instantly claimed compounds of formulae in claim 1. The claim 1 have been searched in their entirety.
Claims 1-12 will be examined on the merits herein.
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 2, 8-12 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) is considered indefinite, since the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c).
Regarding claims 2, 8, 10-12 the phrase "preferably" which is the narrower statement of the range/limitation and renders said claims indefinite because which is the narrower statement of the range/limitation.
Regarding claims 8, 9, 10, 11, 12 the phrase "particularly" which is the narrower statement of the range/limitation, and renders the claims indefinite.
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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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 1-3, 6-12 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2015/110655 (cited by Applicants in IDS).
Regarding instant claim 1, the ‘655 publication teaches a process for preparing alkylated phenols of formula (I)
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by reacting furan substrate acetylene, mediated by gold catalyst (abstract, page1; claims 1,2 of the reference). For example, the preparation of the 2,5-dimethyl phenol by reacting ethyne (acetylene which corresponds to claimed formula III) with 2,5-dimethylfuran as furan substrate in the presence of a gold Au(I) complex catalyst of formula (VI)
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is disclosed on page 3-4).
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Regarding instant claim 1 and 2, the ‘655 publication teaches dimethyl furan which substrate corresponds to claimed substrate furan on formula (II) in which variable R1 is methyl, and tailored with another methyl group at position 5 of furan ring (not claimed), the 2,5-dimethyl phenol corresponds to claimed formula I in which R1 is methyl and further bearing a methyl group at position2 of the phenyl ring (not claimed). The alkylated phenols obtained by the same synthetic methodology have the same utility as the compounds taught by the prior art- intermediates in synthesis of end products (e.g. vitamins; page 1 of the ‘655 publication).
Regarding instant claim 3, the ‘655 publication teaches the Au(complex) comprising phosphorous ligand on page 5, lines 5-10; page 7-8).
Regarding instant claims 6-8, the ‘655 publication teaches silver salt – AgCI or AgSbF6 in combination with Au complex in a ratio 1:1 (page 11, lines 14-17; example 1 on page 16).
Regarding instant claim 9, the ‘655 publication teaches reaction of acetylene: furan substrate in a 1:1 ratio (example 2 page 16).
Regarding instant claim 10, the ‘655 publication teaches the catalyst :furan substrate ranging from 2 : 1 to 10000 : 1 (claim 8 of the reference),
Regarding instant claim 11, the ‘655 publication teaches dichloromethane as solvent (example 2 page 16).
Regarding instant claim 12, the ‘655 publication teaches the reaction conducted at temperature ranging from 10-50 (13 lines 24-25).
The method of the present application differs from the method described in the ‘655 publication in that prior art teaches dimethyl furan which substrate corresponds to claimed substrate furan on formula (II) in which variable R1 is methyl, and tailored with another methyl group at position 5 of furan ring to synthesize the 2,5-dimethyl phenol corresponds to claimed formula I in which R1 is methyl and further bearing a methyl group at position 2 of the phenyl ring, by reaction of the furan substrate with ethylene mediated by Au(complex) catalyst - the same method steps as claimed.
In other words, the furan compound taught by the cited prior art as substrate for the reaction, differs from the instant claimed compounds of formula (II) by a methyl instead of hydrogen at the same loci of molecule. The alkylated phenol product of the reaction taught by the cited prior art differs from the instant claimed compounds of formula (II) by a methyl instead of hydrogen at the same loci of molecule.
Furthermore, the prior art teaches that the methodology is applicable for preparation of phenol with a methyl substituent at different positions of phenyl core structure, demonstrating the versatility of the synthesis of methyl- substituted phenols.
"Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds. For example, a prior art compound may suggest its homologs because homologs often have similar
properties and therefore chemists of ordinary skill would ordinarily contemplate making them to try to obtain compounds with improved properties."
In the instant case, based on structural similarity between the furan substrate of the prior art, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, to modify the teachings of the ‘655 publication concerning reaction of ethylene with furan mediated by Au(complex) catalyst and to utilize a furan substrate with a H instead of a methyl at the same loci of core structure and have reasonable expectation of success to obtain the corresponding alkylated phenol product, because the prior art teach the same synthesis methodology by the same process steps, and furthermore, the synthetic approach as suitable for producing phenol with methyl substituent at different positions of phenyl core structure.
The motivation to make a substitution of a hydrogen for methyl group of furan substrate ( i.e. a 2-methyl furan instead of 2,5-dimethyl furan as substrate for the reaction with ethylene- same substrate as claimed formula III- under same catalyst system to obtain the corresponding phenol product - stems from the fact that a person having ordinary skill in the art would expect that the structurally similar compounds could be prepared by the same method as taught by the prior art and have the same utility as the compounds taught by the prior art- intermediates in the synthesis of end products.
Thus, the claimed invention as a whole is prima facie obvious over the teachings of the prior art.
Claim Objections
Claims 4 and 5 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Conclusion
Claims 1-3, 6-12 are rejected. Claims 4,5, are objected to. Claims 13-17 are withdrawn from further consideration.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANA MURESAN whose telephone number is (571)-270-7587. The examiner can normally be reached on Monday through Friday, 8:30 am to 5:30 pm EST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692