CTNF 18/557,560 CTNF 87092 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Election/Restrictions Applicant’s response to the restriction/ election requirement from 1/30/2026 is acknowledged. Applicant has elected, without traverse, the invention of Group I, claims 1-14, 17 and 18. Applicant has further made the following species election of a compound: PNG media_image1.png 51 628 media_image1.png Greyscale PNG media_image2.png 147 203 media_image2.png Greyscale The elected species was searched, and was found to be free of art. The search was therefore expanded across the breadth of the claimed compounds. The restriction/ election requirement is hereby MADE FINAL. Claims 1-14, 17 and 18 are pending, and have been examined herewith across their breadth. Claim Rejections - 35 USC § 102 07-07-aia AIA 07-07 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 – 07-08-aia AIA (a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention. 07-12-aia AIA (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. 07-15 AIA Claim s 1-4, 6-9 and 14 are rejected under 35 U.S.C. 102( a)(1) and 35 U.S.C. 102(a)(2 ) as being anticipated by US 4,482,556 to Lal et al. (“Lal”) . Lal discloses pyrimido (6,1-a)isoquinolin-4-one compounds useful as hypotensive agents, bronchodilators, and anti-allergenics, of the following formula, and compositions thereof with pharmaceutically acceptable carriers. (Abstract, claim 1, col. 24, ll. 3-16). PNG media_image3.png 144 142 media_image3.png Greyscale PNG media_image4.png 378 255 media_image4.png Greyscale Lal discloses the following specific compounds. PNG media_image5.png 200 400 media_image5.png Greyscale (claim 2- 9,10-Dimethoxy-2-tert.-butylamino-6,7-dihydro-4H-pyrimido(6,1-a)isoquinoline-4 -one hydrochloride) PNG media_image6.png 200 400 media_image6.png Greyscale (claim 3- 9,10-Dimethoxy-2 -(2,4,6-trimethylanilino)-6,7-dihydro-4H-pyrimido(6,1-a)isoquinolin-4-one hydrochloride dihydrate) PNG media_image7.png 200 400 media_image7.png Greyscale (claim 4- 9,10-Dimethoxy-3-methy l-2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido(6,1-a)isoquinolin-4-one hydrochloride) PNG media_image8.png 200 400 media_image8.png Greyscale (claim 5- 9,10-Dimethoxy-2-(N-methyl-2,4,6-trimethylanilino)-6,7-dihydro-4H-pyrimido(6,1-a)isoquinolin-4-one hydrochloride) PNG media_image9.png 200 400 media_image9.png Greyscale (claim 6- 9,10-Dimethoxy-3-isopropyl-2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido(6,1-a)isoquinolin-4-one hydrochloride) PNG media_image10.png 200 400 media_image10.png Greyscale (claim 7- 9,10-Dimethoxy-2-(N-isopropyl-2,4,6-trimethylanilino)-6,7-dihydro-4H-pyrimido(6,1-a)iso quinolin-4-one hydrochloride) PNG media_image11.png 200 400 media_image11.png Greyscale (claim 8- 9,10-Dimethoxy-3-ethyl-2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido(6,1-a)isoquinolin-4-one hydrochloride) PNG media_image12.png 200 400 media_image12.png Greyscale (claim 9- 9,10-Dimethoxy-2-(N-ethyl-2,4,6-trimethylanilino)-6,7-dihydro-4H-pyrimido(6,1-a)isoquinolin-4-one hydrochloride) PNG media_image13.png 200 400 media_image13.png Greyscale (claim 10- 9,10-Dimethoxy-3-acetyl-2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido(6,1-a)isoquinolin-4-one) PNG media_image14.png 200 400 media_image14.png Greyscale (claim 11- 9,10-Dimethoxy-2-(N-acetyl-2,4,6-trimethylanilino)-6,7-dihydro-4H-pyrimido(6,1-a)isoquinolin-4-one) See the structure of claim 2 for comparison with Applicant’s specifically claimed species of compound, with the difference being in R3 of Lal: PNG media_image6.png 200 400 media_image6.png Greyscale (claim 3- 9,10-Dimethoxy-2 -(2,4,6-trimethylanilino)-6,7-dihydro-4H-pyrimido(6,1-a)isoquinolin-4-one hydrochloride dihydrate) This is Applicant’s claimed species: PNG media_image15.png 142 196 media_image15.png Greyscale This discloses an overlap as to the phenyl substituted group, where in Lal the phenyl group attached to the side chain nitrogen can be phenyl-C1-C2-alkyl, wherein the phenyl is mono-, di-, or tri- substituted with C1-C3 alkoxy, C1-C6 alkanoyl, unsubstituted phenyl, or by phenyl mono- or poly- substituted with C1-C3 alkoxy, C1- C3- alkyl , halogen, or trifluoromethyl. In Lal, in addition to the phenyl groups noted (R2 in Lal), the other group at this position (R3 in Lal) can also be H, OH, NH2, C1-C6 alkyl substituted by furyl or tetrahydrofuryl, C1-C6 alkyl, C1-C6 hydroxyalkyl, di(C1-C3 alkoxy) C1-C6 alkyl, halo-C1-C6 alkyl, di(C1-C4 alkyl)amino C1-C6 alkyl. The difference with Applicant’s claimed species, and broadly with Applicant’s claimed compounds in claims 10-14 (formula IV) is the compound group selected with a square in the structure above. Thus, assuming R2 as in Applicant’s claimed species, and regarding the broader structure with respect to R3, it can be seen that if m is 1-4, L is a single bond, and Cy is heteroaryl, then this reads on R3 of Lal, which is heteroaryl, as this heteroaryl can be C1-C4 alkyl substituted by furyl. Claim Objections Claims 5, 10-13, 17 and 18 are objected to as dependent on a rejected base claim, but would be allowable if written in independent claim format. Any inquiry concerning this communication or earlier communications from the examiner should be directed to SVETLANA M IVANOVA whose telephone number is (571)270-3277. The examiner can normally be reached 8:30-5:00. 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, Kortney L. Klinkel can be reached at (571) 270-5239. 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. /SVETLANA M IVANOVA/Primary Examiner, Art Unit 1627 Application/Control Number: 18/557,560 Page 2 Art Unit: 1627 Application/Control Number: 18/557,560 Page 3 Art Unit: 1627 Application/Control Number: 18/557,560 Page 4 Art Unit: 1627 Application/Control Number: 18/557,560 Page 5 Art Unit: 1627