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 September 01, 2026. As filed Claims 1-15 are pending.
Priority
This application filed 08/11/2023 is a National Stage entry of PCT/EP2022/053012 , International Filing Date: 02/08/2022 PCT/EP2022/053012 Claims Priority from Provisional Application 63148182 , filed 02/11/2021 claims foreign priority to 21158321.6, filed 02/22/2021.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herein.
Election/Restrictions
Applicant’s election without traverse of Group II, claims 5-14 drawn to a process for the preparation of a compound of formula (I) in the reply filed on 09/01/2026 is acknowledged.
Applicant elected the species of the
PNG
media_image1.png
200
400
media_image1.png
Greyscale
PNG
media_image2.png
200
400
media_image2.png
Greyscale
PNG
media_image3.png
200
400
media_image3.png
Greyscale
The Applicants noted that claims 5-14 read on the elected species.
Applicants’ elected species is not allowable due to the following rejections.
Claims 1-4, 15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claims 5-14 will be examined on the merits herein to the extent they read on the elected species.
Claim Objections
Claim 1, 13 are objected for reciting improper Markush language: the recitation in claim 1 “represents” pertaining to the definition of variables of Markush formula I-III and in claim 13 “selected from the group of” should be changed to “selected from the group consisting of”. See MPEP 803.02. “A Markush-type claim recites alternatives in a format such as "selected from the group consisting of A, B and C."
Appropriate correction is required.
Claim Rejections - 35 USC § 102
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 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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 5-7, 9-14 are rejected under 35 U.S.C. 102(a) (1) as being anticipated by Fehr et al Helvetica Chimica Acta (2005), 88(12), 3128-3136 (cited by Applicants in IDS).
Instant claims are drawn to a process for the preparation of a compound formula (I) by reaction Thiol R-SH with a substrate of formula
PNG
media_image4.png
200
400
media_image4.png
Greyscale
.
The article by Fehr teaches on Scheme 5 page 3132 thio-Michael adducts of a- and d-damascone with the odorless dodecane-1-thiol – which corresponds to claimed formula R-Shin which R is C10 alkane (and the elected species; instant claim 9-10). The additions were very rapid in the presence of only 1 mol-% of DBU ( the base of instant claim 14). The adducts 13 and 14 showed excellent releasing properties, were
stable upon storage, and their preparations were straightforward. The compound 14 disclosed by the prior art 3-(dodecylthio)-1-[2, 6,6-trimethyl-3-cyclohexen-1-yl]-J-butanone (instant claim 13; the elected species - corresponds to the claimed formula I in which variable P is represented by the formula (II) in which R1 represents a C6 cyclic alkenyl radical, substituted by three C1 alkyl groups; R2 is a hydrogen atom; R3 and R 4 represent independently of each other a hydrogen atom or a C1 to C15 linear alkyl; and R represents a linear alkyl group having from 8 to 15 carbon atoms (instant claims 5, 11, 12, 13).
PNG
media_image5.png
200
400
media_image5.png
Greyscale
Regarding instant claims 6-7, the limitation of instant claim 6 wherein the thiol of formula R-SH comprises “at most” which reads on “zero” or absence of the additional components; similarly, instant claim 7 limitation “ the thiol of formula R-SH is devoid of traces of ..” reads on absence of the impurities. Since the prior art discloses dodecane-1-thiol, without any other impurities therefore, the prior art meets limitations of insta claims 6 and 7.
Shown below is the reaction of the thiol substrate to unsaturated ketene disclosed by Fehr as displayed in CASREACT data base:
PNG
media_image6.png
245
456
media_image6.png
Greyscale
Therefore, the prior art teaches the limitations of instant claims.
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 1-14 are rejected under 35 U.S.C. 103 as being unpatentable Fehr et al Helvetica Chimica Acta (2005), 88(12), 3128-3136 (cited by Applicants in IDS).
The article by Fehr teaches on Scheme 5 page 3132 thio-Michael adducts of a- and d-damascone with the odorless dodecane-1-thiol – which corresponds to claimed formula R-Shin which R is C10 alkane (and the elected species; instant claim 9-10). The additions were very rapid in the presence of only 1 mol-% of DBU ( the base of instant claim 14). The adducts 13 and 14 showed excellent releasing properties, were
stable upon storage, and their preparations were straightforward. The compound 14 disclosed by the prior art 3-(dodecylthio)-1-[2, 6,6-trimethyl-3-cyclohexen-1-yl]-J-butanone (instant claim 13; the elected species - corresponds to the claimed formula I in which variable P is represented by the formula (II) in which R1 represents a C6 cyclic alkenyl radical, substituted by three C1 alkyl groups; R2 is a hydrogen atom; R3 and R 4 represent independently of each other a hydrogen atom or a C1 to C15 linear alkyl; and R represents a linear alkyl group having from 8 to 15 carbon atoms (instant claims 5, 11, 12, 13.
PNG
media_image5.png
200
400
media_image5.png
Greyscale
Regarding instant claims 6-7, the limitation of instant claim 6 wherein the thiol of formula R-SH comprises “at most” which reads on “zero” or absence of the additional components; similarly, instant claim 7 limitation “ the thiol of formula R-SH is devoid of traces of ..” reads on absence of the impurities. Since the prior art discloses dodecane-1-thiol, without any other impurities therefore, the prior art meets limitations of instant claims 6 and 7.
The method of the present application differs from the method described in the article by Fehr in that prior art does not that the thiol reagent is purified by distillation prior to the reaction.
However, it is noted that using a purified reagent for the reaction, is obvious to a person skilled in the art.
Furthermore, per MPEP 716.02 guidance:” Any differences between the claimed invention and the prior art may be expected to result in some differences in properties. The issue is whether the properties differ to such an extent that the difference is really unexpected. In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).”
And further MPEP 2144.04:” Factors to be considered in determining whether a purified form of an old product is obvious over the prior art include whether the claimed chemical compound or composition has the same utility as closely related materials in the prior art, and whether the prior art suggests the particular form or structure of the claimed material or suitable methods of obtaining that form or structure. In re Cofer, 354 F.2d 664, 148 USPQ 268 (CCPA 1966.
In the instant case, the prior art by Fehr teaches reacting with the odorless
dodecane-1-thiol – which corresponds to the elected species with substrates to product thio-Michael adducts which are encompasses din the scope of claimed formula I by the same method steps.
Given the disclosure in the prior art, the thiol disclosed by the prior art appears to be of same purity as of instant claims, absent a showing side-by-side date demonstrating, that thiol disclosed by prior art is distinct, and of unexpected properties, the instant claims are prima facie obvious.
The office does not have the facilities and resources to provide the factual evidence needed in order to establish that the dodecane-1-thiol of the prior art does not possess the same material, structural and functional characteristics of the claimed thiol. In the absence of evidence to the contrary, the burden is on the applicant to prove that the claimed dodecane-1-thiol of purity different from the compound taught by the prior art and to establish patentable differences. See In re Best 562F.2d 1252, 195 USPQ 430 (CCPA 1977) and Ex parte Gray 10 USPQ 2d 1922 (PTO Bd. Pat. App. & Int. 1989).
The presently claimed invention therefore corresponds to use of known technique to improve similar devices in the same way.
Thus, the claimed invention as a whole is prima facie obvious over the combined teachings of the prior art.
Conclusion
Claims 5-14 are rejected. Claims 1-4, 15 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.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/ANA Z MURESAN/Primary Examiner, Art Unit 1692
Prosecution Insights