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 the Claims
The amendment filed on 03/10/2026 has been entered. Claims 16, 20-21, 25, 27 and 29 have been amended, and thus claims 16-30 are currently pending and under examination.
Withdrawn Objections and Rejections
The objection to the specification and claims 20 and 25 have been withdrawn in view of the amendments.
The indefinite languages of claims 16 and 25 have been obviated and the 112(b) rejection of the claims has been withdrawn. The 112(b) rejection of claims 16-20, 22-26 and 28-30 has been withdrawn.
Claim Objections
Claim 17 is newly 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.
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 21 and 27 are newly 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.
Claim 21 has been amended to recite the extraction step c) obtains an organic phase and is further comprising step cII) of crystallizing the 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester from the organic phase obtained in step c). In view of claim 16, the step that would follow step cII) of claim 21 is step d) of absorbing dissolved 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester in the organic phase over at least two different absorbers. It appears that there are two different forms of 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester in these claims that will be treated by step d) of absorbing…, i.e. the dissolved form per claim 16 and the crystallized form per claim 21, in which the latter renders claim 21 vague and indefinite because it is unclear how the crystallized form can be absorbed in step d), when step d) requires the dissolved form.
Note: To obviate this indefinite language, Applicant is advised in amending claim 21 by incorporating the scope of claim 22 as the latter dissolves the crystallized form to obtain the 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester in an organic solvent, which is a consistent form of claim 16 step d).
Regarding claim 27, the claim is now dependent on claim 22 and recites a step e) of removing the organic solvent that renders the claim indefinite. Claim 22 dissolves the crystallized 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester product prior to the absorption step d). It is unclear if step e) of claim 22 is being conducted after dissolving the crystallized 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester in the organic solvent or after the absorption step d). If the former, the claim would also be unclear because if the organic solvent is removed after dissolving the crystallized 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester, the remaining form is crystals but step d) requires the dissolved form.
For purpose of applying art, step e) of claim 27 will be interpreted as being conducted after the absorption step d).
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.
Claims 16, 18-26 and 28 stand rejected and claim 27 is newly rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US20050165099A1 (US’099; cited in IDS 06/08/2023).
Regarding claims 16, 18-20, 23-24 and 26, US’099 teaches a method for producing 2-(4-N,N-dialkylamino-2-hydroxybenzoyl)benzoates of formula (I), in which L3-N,N-dialkylamimophenol of formula (II) is reacted with phthalic anhydride of formula (III) to obtain 2-(4-N,N-dialkylamino-2-hydroxybenzoyl) benzoic acid of formula (IV) and II. said 2(4-N,N-dialkylamino-2-hydroxybenzoyl)benzoic acid of formula (IV) that has been formed in stage I. is esterified by means of a C1-C12 alcohol or a cyclic C3-C10 alcohol in the presence of an acidic catalyst to obtain 2-(4-N,N-dialkylamino-2-hydroxybenzoyl)benzoate of formula (I), among which 2-(4′-diethylamino-2′-hydroxybenzoyl)benzoic acid hexyl ester is prepared (Examples 1-2). The reference further teaches neutralizing the reaction mixture with 25% strength NaOH solution; separating off the aqueous phase; and isolating the ester after purification by adsorbent and/or by distillation ([0022], [0038], and Examples 1-2). The adsorbents used in the process step are generally solid substances which, due to their large surface area, are able to selectively adsorb impurities from liquid mixtures at their interface, and that preference is given to adsorbents chosen from the group consisting of activated carbons, aluminum oxides, zeolites and silica gels ([0039]).
It is noted that neutralizing the reaction mixture is understood to mean bringing the pH of the reaction mixture to 7, whereas the instant claims recite adjusting the pH of the reaction mixture to a pH of more than 7. However, in view of MPEP § 2144.05, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. See also Warner-Jenkinson Co., Inc. v. Hilton Davis Chemical Co., 520 U.S. 17, 41 USPQ2d 1865 (1997) (under the doctrine of equivalents, a purification process using a pH of 5.0 could infringe a patented purification process requiring a pH of 6.0-9.0).
The method of US’099 fails to teach adsorbing the dissolved 2-(4′-diethylamino-2′-hydroxybenzoyl)benzoic acid hexyl ester over at least two different adsorbents as instantly claimed other than indicating that the adsorbents used in the process step are able to selectively adsorb impurities from liquid mixtures and listing a selection of adsorbents. However, in accordance with MPEP § 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (A) “Combining prior art elements according to known methods to yield predictable results” applies. In this instance, combining at least two of the adsorbents set forth in US’099 would yield nothing more than the removal of impurities from liquid mixture.
Regarding claim 21, US’099 teaches that the process also comprises crystallizing the 2-(4-N,N-dialkylamino-2-hydroxybenzoyl)benzoic ester from the alcoholic solution prior to the treatment with an adsorbent and/or distillation, in which after separating off the aqueous phase, the organic phase is cooled and crystallized ([0041] and Example 2).
Regarding claims 22 and 27, the reference further teaches that after crystallized ester is dissolved in toluene, cyclohexane or hexanol prior to the adsorption step, and that the solvents after adsorption are removed by distillation (Examples 3-5).
Regarding 25, US’099 teaches the amount of adsorbent used is in the range from 0.001 to 0.2 g, based in each case on 1 g of the ester to be purified ([0040]). Furthermore, Examples 3-5 teach dissolving 200 g of the ester in 400 mL toluene (= 344.8 g), 75 g of the ester in 190 mL cyclohexane (= 148.01 g), and 200 g of the ester in 400 mL hexanol (= 324.4 g), respectively. In order to calculate the weight percent of the ester based on the total amount of the ester, adsorbent and the solvent, the amount of the absorbent should be determined first. In the above, the adsorbent used is in the range from 0.001 to 0.2 g based on 1 g of the ester, and thus based on 200 g ester of Example 1, 0.2 to 40 g of the adsorbent should be used. Thus, the weight percent of the ester (200 g) based on the total amount of the ester (200 g), adsorbent (0.2-40 g) and the solvent (toluene 344.8 g), is in the range of about 34.2-36.7 wt%.
Regarding claim 28, US’099 teaches the obtained 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid ester contains less than 10 ppm, preferably less than 5 ppm, particularly preferably less than 1 ppm of rhodamine ([0047]).
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process of manufacturing 2-(4′-diethylamino-2′-hydroxybenzoyl)benzoic acid hexyl ester comprising the steps of a) reacting phthalic acid anhydride with 3-N,N-diethylaminophenol to obtain 2-(4′-diethylamino-2′-hydroxybenzoyl)benzoic acid; b) reacting the 2-(4′-diethylamino-2′-hydroxybenzoyl)benzoic acid obtained in step a) with n-hexanol to obtain 2-(4′-diethylamino-2′-hydroxybenzoyl)benzoic acid hexyl ester; c) adjusting the reaction mixture obtained in step b) to a pH of more than 7 followed by extracting at least once with an aqueous phase; and d) adsorbing the dissolved 2-(4′-diethylamino-2′-hydroxybenzoyl)benzoic acid hexyl ester over at least two different adsorbents in view of the teachings of US’099.
Claims 29-30 are newly rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US20050165099A1 (US’099; cited in IDS 06/08/2023).
Regarding claim 29, US’099 teaches a 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester Ia ([0067]), in which the ester comprises less than 10 ppm, preferably less than 5 ppm, particularly preferably less than 1 ppm of rhodamine ([0047]). The same rhodamine content is disclosed in the instant specification (page 2) and rhodamine is described as the source that discolors 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester (pg. 1).
Regarding claims 29-30, US’099 is silent that the ester has a Gardner value of less than 7.9 (claim 29) and has a Yellowness Index of less than 89 and/or a Hess-Ives of less than 19 (claim 30). However, the reference teaches that the method obtains a colorless ester product ([0010] and Examples 3-5) and as such, there is a prima facie case of anticipation or obviousness for the 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester of US’099 to have a Gardner value of less than 7.9 and a Yellowness Index of less than 89 and/or a Hess-Ives of less than 19.
It is further noted that US’099 uses substantially the same process as in the instant disclosure, i.e.
A method for producing 2-(4-N,N-dialkylamino-2-hydroxybenzoyl)benzoates of formula (I), in which L3-N,N-dialkylamimophenol of formula (II) is reacted with phthalic anhydride of formula (III) to obtain 2-(4-N,N-dialkylamino-2-hydroxybenzoyl) benzoic acid of formula (IV) and II. said 2(4-N,N-dialkylamino-2-hydroxybenzoyl)benzoic acid of formula (IV) that has been formed in stage I. is esterified by means of a C1-C12 alcohol or a cyclic C3-C10 alcohol in the presence of an acidic catalyst to obtain 2-(4-N,N-dialkylamino-2-hydroxybenzoyl)benzoate of formula (I), among which 2-(4′-diethylamino-2′-hydroxybenzoyl)benzoic acid hexyl ester is prepared (Examples 1-2). The reference further teaches neutralizing the reaction mixture with 25% strength NaOH solution; separating off the aqueous phase; and isolating the ester after purification by adsorbent and/or by distillation ([0022], [0038], and Examples 1-2). The adsorbents used in the process step are generally solid substances which, due to their large surface area, are able to selectively adsorb impurities from liquid mixtures at their interface, and that preference is given to adsorbents chosen from the group consisting of activated carbons, aluminum oxides, zeolites and silica gels ([0039]). Neutralizing the reaction mixture is understood to mean bringing the pH of the reaction mixture to 7, whereas the instant claims recite adjusting the pH of the reaction mixture to a pH of more than 7. However, in view of MPEP § 2144.05, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. See also Warner-Jenkinson Co., Inc. v. Hilton Davis Chemical Co., 520 U.S. 17, 41 USPQ2d 1865 (1997) (under the doctrine of equivalents, a purification process using a pH of 5.0 could infringe a patented purification process requiring a pH of 6.0-9.0).
Applicant is advised to See MPEP § 2112.01:
Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). Therefore, the prima facie case can be rebutted by evidence showing that the prior art products do not necessarily possess the characteristics of the claimed product. In re Best, 562 F.2d at 1255, 195 USPQ at 433. See also Titanium Metals Corp. v. Banner, 778 F.2d 775, 227 USPQ 773 (Fed. Cir. 1985) (Claims were directed to a titanium alloy containing 0.2-0.4% Mo and 0.6-0.9% Ni having corrosion resistance. A Russian article disclosed a titanium alloy containing 0.25% Mo and 0.75% Ni but was silent as to corrosion resistance. The Federal Circuit held that the claim was anticipated because the percentages of Mo and Ni were squarely within the claimed ranges. The court went on to say that it was immaterial what properties the alloys had or who discovered the properties because the composition is the same and thus must necessarily exhibit the properties.)
Response to the Arguments
Applicant argues that adjusting the pH value to more than 7 and using two different adsorbents as in claim 16, an improved 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester having reduced amount of color impurities can be obtained as shown in Table 2 with examples IE1 and IE2 and compared to Comparative examples C3 and C4.
Furthermore, Applicant argues that US’099 does not disclose the required Gardner values.
The Examiner disagrees. The pH value used in IE1 and IE2, 11.4 and 11.5, does not represent the entire range of the claimed pH of more than 7. The lowest point of the claimed range is merely close to prior art’s pH 7 that the same or substantially the same result is expected in the final product 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester of both the prior art and the instant claim when the process is conducted at pH value that is merely close to 7, i.e. at the pH of more than 7. Applicant has not provided enough data of the unexpected results by testing different data points of the claimed pH of more than 7. In the absence of such criticality, the instant claimed invention remains obvious for reasons of the record.
With respect to claims 29-30, as indicated in the above rejection, because the prior art’s 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester appears to be substantially the same (with low ppm of rhodamine), and is produced by substantially the same process as in the instant disclosure, the examiner maintains there is a prima facie case of anticipation or obviousness for the 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester of US’099 to have a Gardner value of less than 7.9.
In view of the foregoing, the 103 rejections have not been withdrawn.
Allowable Subject Matter
The subject matter of claim 17 is free of prior art reference. The closest prior art reference is Patent application publication number US20050165099A1 (US’099; cited in IDS 06/08/2023). The teachings of US’099 has been set forth above but the reference fails to teach or suggest that the 3-N,N-diethylaminophenol applied in step a) is distilled prior reacting with the phthalic acid anhydride and/or has a Gardner value of 20 or lower, a Yellowness Index of 80 or lower, and/or a Hess-Ives of 350 or lower.
Conclusion
Claims 16 and 18-30 are rejected and no claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
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 published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
Prosecution Insights