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, 8, 11, and 16 have undergone amendments. Claims 2-7, 9-10, 12-15, and 17-25 have been cancelled. Claims 26-29 are newly added. Thus, Claims 1, 8, 11, 16, and 26-29, submitted 12 January 2026, 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.
Response to Amendment
The objection to Claim 15 is withdrawn. Applicant has canceled Claim 15, rendering the objection moot.
The objection to Claim 1 is withdrawn. Applicant has amended Claim 1 to remove the repeated variables.
The object to Claim 8 is withdrawn. Applicant has corrected the typographical error.
The 35 U.S.C. § 112(b) rejection of Claim 1 for the phrase “comprising Formula (I)” is withdrawn. Applicant has amended the claim to recite “compound having Formula (I)”.
The 35 U.S.C § 112(b) rejection of Claim 1 for containing a broad range or limitation with a narrow range is withdrawn. Applicant has amended the claim to correct the indefiniteness.
The 35 U.S.C. § 112(b) rejection of Claim 1 for claiming C5 aryl, C3 aralkyl, C1 alkyne, and C1 alkylene is withdrawn. Applicant has removed these substituents from the claims.
The 35 U.S.C. § 112(b) rejection of Claim 16 is withdrawn. Applicant has amended the claim to clarify the indefiniteness.
The 35 U.S.C. § 112(d) rejections of Claims 7 and 15 are withdrawn. Applicant has canceled these claims, rendering the rejections moot.
The 35 U.S.C. § 112(d) rejection of Claim 8 is withdrawn. Applicant has amended the dependency of the claim, overcoming the rejection.
The 35 U.S.C. § 112(d) rejection of Claim 16 is withdrawn. Applicant has amended Claim 1 to remove the proviso, overcoming the rejection.
Each of the 35 U.S.C. § 102 rejections of the previous Office Action are withdrawn. Applicant has amended the claims to further define the compounds of Formula (I) such that the cited references do not anticipate or meet the limitations of the amended claims.
The 35 U.S.C. § 103 rejection of Claims 1-16 over STN RN 2148972-54-5 in view of Thornber is withdrawn. Applicant has amended Claim 1 to require variable R3 as C6-C12 aryl or C5-C12 heteroaryl, which is not taught or suggested in the cited reference.
The non-statutory double patenting rejection of Claims 1-16 over Claim 18 of U.S. Patent No. 10,428,022 is withdrawn. The compounds of ‘022 do not teach, suggest or provide a motivation for a compound wherein variable R3 is C6-C12 aryl or C5-C12 heteroaryl.
Claim Objections
Claim 1 objected to because of the following informalities: Variable R5 should have NCH3 changed to read N(CH3) to clarify that group R6 is attached to the nitrogen. Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)- NEW GROUNDS OF REJECTION
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 8 and 26 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. Claims 8 and 26 depend on Claim 1, which states that variable R3 can be a substituted or unsubstituted C5-C12 heteroaryl. Claim 8 claims several substituents for variable R3 that are not C5 heteroaromatic groups, such as pyrazinyl, pyrimidinyl, imidazoyl, furyl, thiazolyl, 1,2,3 triazolyl. These compounds are five-membered heteroaromatic rings which do not have 5 carbons, and thus lack antecedent basis from the limitations of Claim 1. Claim 26 contains several compounds such as
PNG
media_image1.png
170
341
media_image1.png
Greyscale
,
PNG
media_image2.png
178
358
media_image2.png
Greyscale
,
PNG
media_image3.png
181
358
media_image3.png
Greyscale
,
PNG
media_image4.png
239
337
media_image4.png
Greyscale
,
PNG
media_image5.png
225
341
media_image5.png
Greyscale
,
PNG
media_image6.png
173
380
media_image6.png
Greyscale
,
PNG
media_image7.png
205
334
media_image7.png
Greyscale
, and
PNG
media_image8.png
178
360
media_image8.png
Greyscale
wherein variable R3 is not a C5 heteroaromatic ring, which lacks antecedent basis from the limitations of Claim 1.
Claim 26 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. Claim 26 recites the limitation of the compound "
PNG
media_image9.png
174
362
media_image9.png
Greyscale
". There is insufficient antecedent basis for this limitation in the claim as Claim 26 depends on Claim 1, which states that variable R-3 can be aryl or heteroaryl. The moiety at R3 for this compound is not aromatic or heteroaromatic, and lacks antecedent basis.
Claim Rejections - 35 USC § 112(d)- NEW GROUNDS OF REJECTION
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.
Claims 8 and 26 are 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. Claims 8 and 26 depend on Claim 1, which states that variable R3 can be a substituted or unsubstituted C5-C12 heteroaryl. Claim 8 claims several substituents for variable R3 that are not C5 heteroaromatic groups, such as pyrazinyl, pyrimidinyl, imidazoyl, furyl, thiazolyl, and 1,2,3 triazolyl. These compounds are five-membered heteroaromatic rings which do not have 5 carbons. Claim 26 claims several compounds several compounds such as
PNG
media_image1.png
170
341
media_image1.png
Greyscale
,
PNG
media_image2.png
178
358
media_image2.png
Greyscale
,
PNG
media_image3.png
181
358
media_image3.png
Greyscale
,
PNG
media_image4.png
239
337
media_image4.png
Greyscale
,
PNG
media_image5.png
225
341
media_image5.png
Greyscale
,
PNG
media_image6.png
173
380
media_image6.png
Greyscale
,
PNG
media_image7.png
205
334
media_image7.png
Greyscale
, and
PNG
media_image8.png
178
360
media_image8.png
Greyscale
wherein variable R3 is not a C5 heteroaromatic ring. As these claims are drawn towards substituents for variable R3 which are not C5 heteroaromatic rings, they do not further limit, and are broader than, Claim 1. 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 26 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 26 depends on Claim 1, which states that variable R-3 can only be aryl or heteroaryl. The compound
PNG
media_image9.png
174
362
media_image9.png
Greyscale
has variable R-3 as phenyl fused to cyclopentyl, which is not an aryl ring, causing this compound to be outside of the scope, and thus does not further limit, Claim 1. 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.
Allowable Subject Matter
Claim 1 is objected to, but allowable.
Claims 11, 16, and 27-29 are allowable.
The following is an examiner’s statement of reasons for allowance: The prior art does not teach or suggest the compounds claimed in the examined application (See STN Search, Search Notes). The closest prior art comes from U.S. Patent No. 10,428,022 (Patent Date: 1 October 2019) (‘022). This patent discloses deoxynojirimycin derivatives which are useful for the treatment of viral infections. Compounds of the invention include
PNG
media_image10.png
203
315
media_image10.png
Greyscale
and
PNG
media_image11.png
222
299
media_image11.png
Greyscale
. These compounds have variables A1 through A4 each as OH, variable R1 as hexyl, variable R2 as NH, variable R3 as substituted phenyl, variables R4 and R5 as absent, and variable R6 as a heteroaryl. There is no teaching, suggestion, or motivation provided to shorten the alkyl chain of variable R1 to methyl, ethyl, or propyl, nor is there motivation provided to incorporate an alkyl chain and amine following the phenyl ring, or to replace the heteroaromatic ring with a phenyl group. Zhang (Bioorganic and Medicinal Chemistry Letters, 27 (2017) 4309-4313) (See IDS, 13 January 2025) discloses quinazoline-1-deoxynojirimycin hybrid compounds which were evaluated for their inhibitory capacity against epidermal growth factor receptor tyrosine kinase and α-glucosidase (Abstract). One compound disclosed is
PNG
media_image12.png
228
414
media_image12.png
Greyscale
, which has variable R1 as ethyl, variable R2 as -O-, variable R3 as substituted heteroaryl, variable R4 as absent, and variable R5 as -NH-, with the terminal phenyl ring substituted with fluorine and chlorine. There is no teaching, suggestion, or motivation for the modification of this compound by both replacing the -O- with -NH-, or removing this group entirely, and inserting a C1-C3 alkyl chain following the heteroaryl group, nor is there any reasonable expectation that performing both of these modifications would result in a compound with similar activity towards α-glucosidase. Diot (Journal of Organic Chemistry, 2011, 76, 7757-7768) discloses the glucosidase inhibitor Compound 38
PNG
media_image13.png
164
485
media_image13.png
Greyscale
(Table 2), which has variables A1 through A4 each as hydroxyl, variable R1 as propyl, variable R2 absent, variable R3 as triazine (a C2 heteroaromatic ring), variable R-4 as methyl, oxygen in place of nitrogen (a bioisosteric replacement as both have similar electronic properties), and the terminal phenyl ring substituted by chlorine. This compound is shown to be a potent inhibitor of bovine liver and almond β-glucosidase, baker’s yeast α-glucosidase, and A. niger amyloglucosidase (Table 3). Table 4 also demonstrates that this compound has an IC50 of well below 5 µM against β-GCase in mutant Gaucher cells. However, the current claims state that variable R3 must be a C5 heteroaromatic ring, and there is no teaching, suggestion, or motivation provided to remove this group and replace with a C5 or larger heteroaromatic group as all compounds disclosed by Diot contain this triazine group, and there would be no expectation that this would result in a compound with similar properties.
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
Claim 1 is objected to, but allowable.
Claims 11, 16, and 27-29 are allowable.
Claims 8 and 26 are rejected.
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 PHILLIP MATTHEW RZECZYCKI whose telephone number is (703)756-5326. The examiner can normally be reached Monday Thru Friday 730AM-5PM EST.
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, 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.
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.
/P.M.R./Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
Prosecution Insights