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 .
Priority
2. The instant application is a national stage entry of PCT/EP2022/063787 filed May 31, 2021.
3. Acknowledgment is made of applicant's claim for foreign priority under 35 U.S.C. 119(a)-(d) by application no. EP21176930.2 filed in the European Patent Office on May 31, 2021, which papers have been placed of record in the file.
Status of Claims
4. Claims 1-13 are pending and under consideration.
Claim Objections
5. Claim 10 is objected to for repeated erroneous usage of “the water” in line 2.
Claim Rejections - 35 USC § 112
6. 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.
7. Claims 5, 8, 10, and 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) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c).
In the present instance, claim 5 recites the broad recitation “wherein the cosolvent is selected from the group consisting of benzonitrile, nitrobenzene and pivalonitrile…” and the claim also recites “preferably benzonitrile…;” which is the narrower statement of the range/limitation.
Claim 8 recites the broad recitation “wherein the temperature in step (ii) is selected in the range of 20 to 100…” and the claim also recites “preferably in the range of 40 to 80….most preferably in the range of 50 to 75…;” which is the narrower statement of the range/limitation.
Claim 10 recites the broad recitation “wherein the water in step (iv) is preheated is …” and the claim also recites “preferably to a temperature selected in the range of 60 to 100….most preferably in the range of 70 to 95…;” which is the narrower statement of the range/limitation.
Claim 12 recites the broad recitation “wherein the process comprising...alkylation…with an alkyl halogenide…” and the claim also recites “preferably ethylhexyl chloride…;” which is the narrower statement of the range/limitation.
Allowable Subject Matter
8. The subject matter of the present claims is free of the prior art. The closest prior art is as follows: 1) WO 2016/184764, 2) Wang et al. Journal of Fluorescence, 2018, 28, 707-723, and 3) Jiang et al. Journal of Chemical Research, 2008, 11, 664-665. WO 2016/184764 teaches (page 8, Step 2) preparation of compounds of formula (I) comprising reacting a compound (II) in the aromatic solvent toluene with resorcinol in the presence of Lewis Acid, AlCl3 and co-solvent benzonitrile. After completed reaction, aqueous HCl, toluene, and water are added to the reaction mixture. The resulting suspension was filtered and the filter cake was washed and dried. The difference between WO 2016/184764 and the present claims is that WO 2016/184764 does not teach steps (i) to (iv) of claim 1. Reference 2) teaches methods of preparation of formula (I) reacting a compound of formula (II) in the aromatic solvent chlorobenzene with resorcinol in the presence of AlCl3 (Reference 2, page 713, scheme for reaction of 4a to 8e). After completed reaction, ice water was slowly added and then chlorobenzene was evaporated under pressure. The mixture was filtered, washed, and the filter cake recrystallized (Reference 2, page 712, right column, first paragraph). In Reference 3) teaches methods of preparation of formula (I) reacting a compound of formula (II) in the aromatic solvent chlorobenzene with resorcinol in the presence of AlCl3 (Reference 3 page 665, left column, penultimate paragraph). After completed reaction, chlorobenzene was removed from the reaction mixture by steam distillation. The residue was filtered off, washed and dried. The combination of references could render obvious step (i) (the avoidance of any further need of wet cake washings as needed, page 8, lines 1-4 of Reference 1), but steps (ii) to (iv) remain novel and nonobvious. While the combination of all three references teaches various components of the present claims, including the co-solvent taught in WO 2016/184764, the combination of references neither anticipates nor renders obvious steps (ii) to (iv), which are not taught or suggested by any combination of the prior art references.
Conclusion
9. Claims 1-4, 6-7, 9, 11, and 13 are allowed.
10. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Samantha Shterengarts whose telephone number is (571)270-5316. The examiner can normally be reached on Monday thru Thursday 9-6pm.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Adam Milligan can be reached on 571-270-7674. 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.
/SAMANTHA L SHTERENGARTS/Primary Examiner, Art Unit 1623