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
Claims 1-37 are pending.
Priority
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statement filed 05/13/2026 fails to comply with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609 because references B02 and B03 do not have direct English translations provided.
The information disclosure statement filed 06/24/2024 fails to comply with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609 because reference C05 does not have a copy provided.
It has been placed in the application file, but the information referred to in these references only has not been considered as to the merits. Applicant is advised that the date of any re-submission of any item of information contained in this information disclosure statement or the submission of any missing element(s) will be the date of submission for purposes of determining compliance with the requirements based on the time of filing the statement, including all certification requirements for statements under 37 CFR 1.97(e). See MPEP § 609.05(a).
Restriction Requirement
Applicant’s election without traverse of Group I, directed to a process of preparing compound of formula (V), claims 1-28, in the reply filed on 05/13/2026 is acknowledged.
Claims 29-37 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 05/13/2026.
Claim Objections
Claims 7 and 10 are objected to because of the following informalities:
Claim 7 reads “…comprises reacting compound of formula (VII)…” and should read “…comprises reacting the compound of formula (VII)…” (emphasis added).
Claim 10 reads “…with borohydride salt and boron trifluoride tetrahydrofuran complex” and should read “…with a borohydride salt and a boron trifluoride tetrahydrofuran complex” (emphasis added).
Appropriate correction is required.
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.
Claim 4 is 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.
Regarding claim 4, the phrase “preferably” renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Claim Rejections - 35 USC § 103
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 1-16 are rejected under 35 U.S.C. 103 as being unpatentable over Neumeyer (Facile Synthesis of Isoindole and Substituted Isoindoles, J. Pharm. Sci., 1964, Vol. 53(8), pages 981-982), further in view of Cherkez et al. (Synthesis, saludiuretic, and hypertensive activity of 6,7-disubstituted 1(2H)- and 3,4-dihydro-1(2H)-phthalazinones, J. Med. Chem., 1986, Vol. 29(6), pages 947-959).
Neumeyer teaches the synthesis of isoindole and substituted isoindoles. The reaction scheme, shown below from page 982, corresponds to steps (b), (c), and (d) of the instant claims, which includes the steps of adding the benzyl protecting group, reduction, and deprotection.
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Neumeyer fails to teach the synthesis of the starting material compounds Ia, Ib, and Ic shown above.
However, Cherkez et al. teaches, on page 958, the synthesis of 4-chlorophthalimide from 2,4-dichlorobenzoic acid and CuCN, shown below. The reaction was run in pyridine at 130°C.
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Therefore, it would be prima facie obvious to one of ordinary skill in the art to use a known method taught by Cherkez et al. to create the starting material used in the synthesis by Neumeyer, in order to make the compounds taught by Neumeyer et al.
Regarding the substitution of the chlorine group with a trifluoromethyl group in the above syntheses, as required by the instant claims, it would be prima facie obvious to make this substitution, since trifluoromethyls are bioisosteres of halogens. As evidenced by Patani et al. on page 3172, who, when discussing halogen bioisosteres, states “Halogens have been replaced by electron-withdrawing groups such as a cyano or trifluoromethyl group” (Bioisosterism: A Rational Approach in Drug Design, Chem. Rev. 1996, Vol. 96, pages 3147-3176).
One would have a reasonable expectation of success in testing a bioisostere of the above compounds, since these are expected to have the same reactivity and biological efficacy. It is common practice in the art to test bioisosteres and derivatives of close structural similarity when performing syntheses and biological assays in order to compare the efficacy of the derivatives.
Additionally, Neumeyer shows that different substitutions, such as halogens, methyl, amino, and nitro groups, do not hinder the synthesis. Therefore, the trifluoromethyl substitution would not be expected to prevent the synthesis process, and the resulting compound would be expected to have similar chemical and biological properties.
Regarding claims 3, 5, 9-12, and 15, the additives and solvents required by the instant claims would be considered routine optimization. MPEP 2144.05 II A states: “"[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955)”. Therefore, optimizing conditions of a known process is not inventive.
Regarding claim 7, it would have been obvious to one skilled in the arts at the time of the invention to be motivated to attempt the same process with a bromine leaving group, rather than chlorine as taught in the prior art. Graver Tank shows that chlorine and bromine are chemical equivalents, and thus would not alter or affect the claimed process in any way.
The court decision of Graver Tank teaches that the important factor in determining a test for equivalency in a prior art document is whether a person who is reasonably skilled in the art would recognize the equivalency in the compound or composition. In Ex parte Wiseman (POBA 1953) 98 USPQ 277, a difluorinated compound was held unpatentable over the prior art dichloro compound on the basis of analogical reasoning.
Regarding claim 16, it would be prima facie obvious to one of ordinary skill in the art to create a hydrochloride salt of a known compound, since pharmaceutical salts are known to improve the crucial physicochemical properties of drugs, particularly solubility and dissolution, and hydrochloride salts are the most common salts used.
Advisory Notice
Claims 17-28 appear allowable if rewritten in independent form.
Conclusion
Claims 1-16 are rejected.
Claims 17-28 are objected to.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RILLA M SAMSELL whose telephone number is (703)756-5841. The examiner can normally be reached Monday-Friday, 7-3.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey Murray can be reached at (571) 272-9023. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/R.M.S./Examiner, Art Unit 1624
/JEFFREY H MURRAY/Supervisory Patent Examiner, Art Unit 1624
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