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 .
Claims 1-22, submitted on 24 February 2023, represent all claims currently under consideration.
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.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
The effective filing date is 3 September 2020.
Information Disclosure Statement
One Information Disclosure Statement (IDS), submitted on 24 February 2023, is acknowledged and has been considered.
Drawings
The drawings are objected to because Figure 3 is of poor quality and is difficult to interpret. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Objections
Claim 1 is objected to because of the following informalities: the image quality of the compound of formula (I) is of poor quality and is difficult to interpret. Appropriate correction is required.
Claim 9 is objected to because of the following informalities: there is a superfluous “is” prior to “in substantially pure crystalline form”. Appropriate correction is required.
Claim 17 is objected to because of the following informalities: The solvent “1-4 dioxane” should read “1,4-dioxane”. Appropriate correction is required.
Claims 12 and 21 are objected to because of the following informalities: There is a comma missing between isopropanol and acetonitrile in the Markush list of solvents. Appropriate correction is required.
Claims 18 and 19 are objected to because of the following informalities: There is no “and” prior to step (b) in Claim 18. Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
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, 3, 11, 13, 16, and 20 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. The claims are directed towards crystalline compounds of the compound of Formula (I) “having a characteristic X-ray diffraction pattern comprising of the peaks expressed in terms of…”. It is unclear what the phrase “comprising of the peaks” means when describing what is claimed. It is unclear if the crystalline form of the compound of Formula (I) is comprising the pattern, or merely a pattern that is part of the XRPD (i.e., there are other peaks that can be present, but are not defined). Claims 4-9, 12, 14-15, 17 and 21 are rejected as dependent upon an indefinite claim without resolving the underlying issue of indefiniteness.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 3 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 3 is dependent on Claim 2. Both claims recite peaks for an X-ray diffraction pattern for Formula (I); however, Claim 3 claims fewer peaks than Claim 2, and is therefore more broad and does not further limit Claim 2. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 102
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)(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.
Claims 1 and 3-10 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Kulkarni (WO 2021/070150; Publication Date: 15 April 2021; International Filing Date: 11 October 2020, Priority to 11 October 2019).
The applied reference has a common applicant with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2). This rejection under 35 U.S.C. 102(a)(2) might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C. 102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B) if the same invention is not being claimed; or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed in the reference and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement.
Kulkarni (See IDS, 24 February 2023) discloses an inhalable composition comprising a therapeutically effective dosage amount of compound (I), (S)-2-(4-(1,1-difluoro-2-hydroxypropyl)phenyl)-N-(3-(3-(2-ethylphenyl) pyrazin-2-yl)phenyl)acetamide or a pharmaceutically acceptable salt thereof (Abstract). In one embodiment, the compound may exist in amorphous or any crystalline form. In one embodiment, the compound may exist in crystalline Form III and is characterized by characteristic X-ray diffract pattern comprising one or more of the following peaks expressed in terms of 11.3, 12.1, 15.9, 18.1, and 20.0 ± 0.2° theta (Page 9, Lines 6-10). In a specific embodiment, the D90 particle size of compound (I) or a pharmaceutically acceptable salt thereof is less than about 10 µm (Page 21). In a specific embodiment, the D50 particle size of compound (I) is in the range of from about 0.7 microns to about 4 microns (Page 21).
Allowable Subject Matter
Claims 18 and 19 are objected to, but allowable.
Claim 22 is allowable.
The following is an examiner’s statement of reasons for allowance: A search for the claimed compound retrieved only the art which was cited in the IDS, and a co-pending application which describes patentably distinct formulations of the compound (US 2024/0108617; Publication Date: 4 April 2024, Priority to 11 October 2019) (See STN Search Notes). The closest art comes from Kulkarni (cited above) and Das (WO 2017/021879; Publication Date: 9 February 2017). The compound of Formula (I) has only been described previously by Kulkarni and Das. Kulkarni discloses crystalline and amorphous forms of the claimed compound, and describes X-ray diffraction peaks identical to those of Claim 3 of the examined application, but does not disclose all peaks found in Claim 2. Kulkarni also discloses particle sizes of the compound which fall within the limitations that are claimed. Das (See IDS, 24 February 2023) discloses compounds which are active as modulators of retinoid-related orphan receptor gamma t (RORyt). These compounds prevent, inhibit, or suppress the action of RORyt and are therefore useful in the treatment of RORyt mediated diseases, disorders, syndromes, or conditions (Abstract). One compound described is Example 52
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(Page 117), which is identical to the compound of the examined application. Das is silent with regard to the solid state of the compound, and does not describe crystalline or amorphous forms of this compound, or the preparation of such forms. Das discloses methods for the synthesis of the claimed compound which are similar, but not identical or obvious variations of the method which is claimed in the examined application. Synthetic schemes I and II (Page 29) discloses a method which can be used to prepare the compounds of the invention, including example 52.
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The suitable coupling agents using in the reaction may be EDCI, T3P, DCC or HATU. The suitable base may be Et3N, DIPEA, pyridine, or DMAP. The coupling reaction may be carried out in a suitable solvent or mixture thereof. The suitable solvent may be selected from CH2Cl2, CHCl3, DMF, and THF, or a combination thereof. Intermediate 39
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, which is identical to the compound of Formula (II) of Claim 18, is described and is used to synthesize Example 52 using reaction scheme II. The reference does not teach that the compound of Formula (III) can be used in the described reaction scheme I, and does not provide any examples demonstrating the success formation of product using this method without the coupling followed by reduction of the ketone, yielding the alcohol. Compounds which do not contain the hydroxyl group on the terminal fluoro-alkyl group are demonstrated to undergo the reaction of Scheme 1, while example 52 undergoes Scheme 2, and this is described in Method C, where the intermediate
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is prepared by reacting Intermediate 39 with Intermediate 3
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, which then undergoes a condensation to yield the product. There is no description of different polymorphic forms of this compound by Das, nor is there any teaching, suggestion, or motivation provided that would lead one of ordinary skill in the art to choose the specific crystalline form which is claimed, nor is there any teaching, suggestion, or motivation provided which would lead one to select an amorphous form of this compound. While Kulkarni discloses amorphous forms of the compound of Formula (I), there are no methods for preparing this form which are disclosed. There are multiple ways to prepare amorphous forms, such as jet milling, spray drying, wet granulation, drying of solvated crystals, and the claimed method of heating to melt under a vacuum. There is no reasonable expectation of success that this method, among the many known methods, will produce an amorphous form of the compound. Further, Kulkarni discloses the crystalline form of the claimed compound with the same peaks of Claim 3. However, there are no methods described for preparing this polymorph in the disclosure of this invention. There are methods disclosed for the preparation of formulations of this compound, but no description of solvents or methods of preparation of the claimed polymorph.
Any comments considered necessary by applicant must be submitted no later than the payment of the issue fee and, to avoid processing delays, should preferably accompany the issue fee. Such submissions should be clearly labeled “Comments on Statement of Reasons for Allowance.”
Conclusion
Claims 18 and 19 are objected to, but allowable.
Claim 22 is allowable.
Claims 1-17 and 20-21 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PHILLIP MATTHEW RZECZYCKI whose telephone number is (703)756-5326. The examiner can normally be reached Monday Thru Friday 730AM-5PM EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Andrew Kosar can be reached at 571-272-0913. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/P.M.R./ Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625