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 .
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-7 in the reply filed on 9/11/2025 is acknowledged. Claims 20, 21, and 26-34 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claim Status
Claims 1-25 were filed on 8/9/2022. In a preliminary amendment filed on the same day, claims 3-5, 7, and 20 were amended, claims 8-19 and 22-25 were canceled, and claims 26-34 were newly added. In the response filed 9/11/2025, claim 20 was amended. Claims 1-7, 20, 21, and 26-34 are pending. Claims 20, 21, and 26-34 are withdrawn. Claims 1-7 are under examination.
Priority
PNG
media_image1.png
166
950
media_image1.png
Greyscale
See filing receipt dated 12/1/2022. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Interpretation
The limitation “pharmaceutical” in claim 7 is interpreted as an intended use. Paragraphs [0056-0057] of the specification as filed further give examples of “pharmaceutically acceptable carriers”. Therefore, if a composition is found to meet the structural limitations of the claim, then it will be interpreted to fulfill the intended use of the claim. Also see MPEP 2111.02.
Claim Rejections - 35 USC § 102
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.
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)(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.
(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.
Claim(s) 1, 2, and 7 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Oguri (“Amino acids and peptides. XXVIII. A new synthesis of alpha-amino acid derivatives by alkylation of Schiff bases derived from glycine and alanine” Chem. Pharm. Bull, 25, 1977, p. 2287, of record in the IDS filed on 8/9/2022).
Oguri teaches compound (S-Vb): (S)-alpha-methyl-beta-(3,4-dimethoxyphenyl)alanine tert-butyl ester, which is a compound of the following structure:
PNG
media_image2.png
200
400
media_image2.png
Greyscale
. The structure was generated using the “Convert Name to Structure” feature of ChemDraw®. See abstract and “3,4-dimethoxybenzylation of the Schiff Base (IV)” on p. 2291. This compound corresponds to a compound of instant formula (1) wherein R1 and R2 are methyl, a C1 alkyl, and R3 is -OR4, wherein R4 is a tert-butyl group. Also see MPEP 2131.02.
Further regarding claim 7, the work-up of compound S-Vb includes a step of being solubilized in an aqueous solution comprising citric acid. This composition meets the limitations of the claimed composition. See MPEP 2111.02. See experimental procedure of compound S-Vb on p. 2291, which refers to the work-up procedure of compound S-Va on p. 2291-2292.
Claim(s) 1 and 6 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CAS registry no. 1565206-30-5, entered into STN on 3/10/2014.
RN 1565206-30-5 REGISTRY
ED Entered STN: 10 Mar 2014
CN Benzenepropanamide, α-amino-3,4-dihydroxy-α-methyl-N-(2-methylpropyl)-, (αS)- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN (αS)-α-Amino-3,4-dihydroxy-α-methyl-N-(2-methylpropyl)benzenepropanamide
FS STEREOSEARCH
MF C14 H22 N2 O3
INCH InChI=1S/C14H22N2O3/c1-9(2)8-16-13(19)14(3,15)7-10-4-5-11(17)12(18)6-10/h4-6,9,17-18H,7-8,15H2,1-3H3,(H,16,19)/t14-/m0/s1
INKY SSHBYLMMDKWGDH-AWEZNQCLSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
PNG
media_image3.png
216
385
media_image3.png
Greyscale
**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
The compound corresponds to a compound of instant claims 1 and 6 wherein R1 and R2 are H, R3 is -NHR5, and R5 is iso-butyl.
Claim(s) 1-3 and 7 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hajos (“Germinate Aminocarbinols, I” Acta Chimica Academiae Scientiarum Hungaricae, 695, 1966, p. 417-425, including a Google Image generated English translation).
Hajos teaches the sec-butyl ester of alpha-methyl dopamine (referred to as alpha-methyl dopa throughout the publication). See entry 5 of Table 1 on p. 419 and structures on p. 7, wherein the ester above would correspond to a compound of either formula wherein the NH2 group is not further substituted; R1 is methyl (C1 alkyl); and R2 is sec-butyl:
PNG
media_image4.png
200
400
media_image4.png
Greyscale
. Thus, the compound of Hajos corresponds to a compound of instant claims 1-3, wherein R1 and R2 are H; R3 is -OR4 and R4 is sec-butyl. Further regarding claim 3 is it noted that a racemic mixture of the compound will contain both enantiomers. Further regarding, claim 7, the experimental procedure for producing the esters, as exemplified by the alpha-Methyldopa-n-butyl ester experimental procedure on p. 423 (p. 7 of the translation), teaches that the compounds are dried after reaction and dissolved in water. This composition meets the limitations of claim 7 as water is a pharmaceutically acceptable carrier. Also see MPEP 2131.02.
Claim Rejections - 35 USC § 103
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.
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.
Claim(s) 1-5 and 7 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hajos (“Germinate Aminocarbinols, I” Acta Chimica Academiae Scientiarum Hungaricae, 695, 1966, p. 417-425, including a Google Image generated English translation) optionally in view of GB 1077443 (GB ‘443, published 7/26/1967).
Applicant Claims
PNG
media_image5.png
540
898
media_image5.png
Greyscale
Determining the Scope and Content of the Prior Art (MPEP §2141.01)
Hajos teaches the sec-butyl ester of alpha-methyl dopamine (referred to as alpha-methyl dopa throughout the publication). See entry 5 of Table 1 on p. 419 and structures on p. 7, wherein the ester above would correspond to a compound of either formula wherein the NH2 group is not further substituted; R1 is methyl (C1 alkyl); and R2 is sec-butyl:
PNG
media_image4.png
200
400
media_image4.png
Greyscale
. Thus, the compound of Hajos corresponds to a compound of instant claims 1-3, wherein R1 and R2 are H; R3 is -OR4 and R4 is sec-butyl (branched C4 alkyl). Further regarding claim 3 is it noted that a racemic mixture of the compound will contain both enantiomers. Additionally, Hajos teaches that L-dopa is known to be biologically active in the paragraph bridging p. 6-7 of the translation, thus providing further motivation to obtain the enantiomer of claim 3 in a purified form.
Further regarding, claim 7, the experimental procedure for producing the esters, as exemplified by the alpha-Methyldopa-n-butyl ester experimental procedure on p. 423 (p. 7 of the translation), teaches that the compounds are dried after reaction and dissolved in water. This composition meets the limitations of claim 7 as water is a pharmaceutically acceptable carrier.
Hajos further teaches analogous compounds to those of instant formula (I), which correspond to instant R4 being isopropyl (branched C3 alkyl); and n-butyl ester (linear C4 alkyl). See Table 1, entries 4-5.
GB ‘443 is also directed toward the synthesis of geminate amino-carbinols. See abstract. GB ‘443 teaches that the amino-carbinols are produced from phenylalanine esters of formula II:
PNG
media_image6.png
164
550
media_image6.png
Greyscale
. See p. 1, line 25-p. 2, line 3 and claims 1-2. When R2 is a lower alkyl of 4 carbon atoms, the compounds of GB ‘443 correspond to compounds of instant formula (1), wherein R1 and R2 are H, R3 is -OR4 and R4 is a C4 alkyl. C4 alkyl groups include sec-butyl (claim 3), tert-butyl (claim 4), and iso-butyl (claim 5) groups.
Ascertainment of the Difference Between Scope of the Prior Art and the Claims (MPEP §2141.02-03)
Hajos does not explicitly teach compounds of formula I of claims 1-2, 4, and 5, wherein R4 is a tert-butyl (claim 4) or isobutyl (claim 5) group. Hajos teaches structural isomers of these embodiments wherein R4 is sec-butyl or n-butyl; and a one-carbon homolog of the isobutyl embodiment wherein R4 is isopropyl.
Finding of Prima Facie Obviousness Rationale and Motivation (MPEP §2142-2143)
It would have been prima facie obvious to one of ordinary skill in the art to arrive at the instantly claimed compounds based on the teachings of Hajos with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to substitute the sec-butyl group of Hajos with a tert-butyl or iso-butyl group because both are structural isomers of the sec-butyl and n-butyl compounds of Hajos and all C4 alkyl groups. The Hajos compound possessing an isopropyl ester group is also a one-carbon homolog of the isobutyl embodiment. Structural isomers and homologs are presumed to possess similar properties because of their sufficient close structural similarity. See MPEP 2144.09. Therefore, replacing one with another would predictably produce a compound having similar properties as those explicitly described and used in the process of Hajos. Also see MPEP 2143 (B). Additionally, GB ‘443 is additionally cited as an optional reference to provide further support that any C4 group at the instant R4 position would be expected to possess significantly the same properties.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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, Scarlett Goon can be reached at 571-270-5241. 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.
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692