Prosecution Insights
Last updated: April 18, 2026
Application No. 18/244,919

NOVEL PREPARATION METHOD FOR SARCOSINE AND DERIVATIVES THEREOF

Non-Final OA §103§112
Filed
Sep 12, 2023
Examiner
CUTLIFF, YATE KAI RENE
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Qianjiang Yongan Pharmaceutical Co. Ltd.
OA Round
1 (Non-Final)
80%
Grant Probability
Favorable
1-2
OA Rounds
2y 4m
To Grant
99%
With Interview

Examiner Intelligence

Grants 80% — above average
80%
Career Allow Rate
1023 granted / 1281 resolved
+19.9% vs TC avg
Strong +24% interview lift
Without
With
+24.1%
Interview Lift
resolved cases with interview
Typical timeline
2y 4m
Avg Prosecution
24 currently pending
Career history
1305
Total Applications
across all art units

Statute-Specific Performance

§101
2.6%
-37.4% vs TC avg
§103
37.0%
-3.0% vs TC avg
§102
13.8%
-26.2% vs TC avg
§112
33.6%
-6.4% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1281 resolved cases

Office Action

§103 §112
ETAILED 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 Claims Claims 1 – 20 are pending. Claims 1 – 20 are rejected. Information Disclosure Statement The listing of references in the specification is not a proper information disclosure statement. 37 CFR 1.98(b) requires a list of all patents, publications, or other information submitted for consideration by the Office, and MPEP § 609.04(a) states, "the list may not be incorporated into the specification but must be submitted in a separate paper." Therefore, unless the references have been cited by the examiner on form PTO-892, they have not been considered. 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. Claims 1 - 20 are rejected under 35 U.S.C. 112(b), as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, regards as the invention. The terms “sarcosinate”, sarcosine derivative” and “sarcosine”, as used in independent claims 1, 11 and/or 18 are vague in that they blur the scope of the claims. Regarding claims 2 and 4, it seems that in these claims that glycinate (the prepared product when R = H) and other compounds such as N-ethyl glycinate (the prepared product when R = Et) are supposed to be sarcosinates which however contradicts the normal meaning of the term sarcosinate. For this reason the claims lack clarity. Claims 2 – 4, 6 - 8, 10 and 20 are indefinite because a broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 2 recites the broad recitation “R group is -H, -Me, -Et…or C6-C20 aryl”, and the claim also recites “preferably, the R group is -H or -Me” which is the narrower statement of the range/limitation. In the present instance, claim 3 recites the broad recitation ‘…hydrogenation reaction is carried out for 1-24 hours” , and the claim also recites “preferably 8 – 16 hours which is the narrower statement of the range/limitation. In the present instance, claim 4 recites the broad recitation “…a mass percent concentration of 10% to 60%” , and the claim also recites “preferably 30% to 40% which is the narrower statement of the range/limitation. In the present instance, claim 4 recites the broad recitation ‘…R group is -H, -Me, -Et…or C6-C20 aryl”, and the claim also recites “preferably ammonia, methylamine or aromatic amine” which is the narrower statement of the range/limitation. In the present instance, claim 6 recites the broad recitation “…water to the alcohol is 1:0-1:10” , and the claim also recites “preferably …water to the alcohol is 1:0-1:2 which is the narrower statement of the range/limitation. In the present instance, claim 7 recites the broad recitation “…catalyst is one or more Pd, Ni, …and zinc powder” , and the claim also recites “preferably a Pd or Ni metal catalyst” which is the narrower statement of the range/limitation. In the present instance, claim 7 recites the broad recitation “…a carrier of the catalyst is alumina…or expanded perlite” , and the claim also recites “preferably activated carbon, alumina, zeolite or SiO2” which is the narrower statement of the range/limitation. In the present instance, claim 8 recites the broad recitation “a pressure of 0.1-10 MPa” , and the claim also recites “preferably 2-5 MPa” which is the narrower statement of the range/limitation. In the present instance, claim 8 recites the broad recitation “a temperature of 10-150°C” , and the claim also recites “preferably 30-100°C” which is the narrower statement of the range/limitation. In the present instance, claim 9 recites the broad recitation “…inorganic acid or organic acid” , and the claim also recites “preferably sulfuric acid, hydrochloric acid, phosphoric acid, formic acid, or acetic acid” which is the narrower statement of the range/limitation. In the present instance, claim 9 recites the broad recitation “… inorganic metal hydroxide, inorganic ammonia or an organic amine” , and the claim also recites “preferably lithium hydroxide, sodium hydroxide, potassium hydroxide, ammonia or methylamine” which is the narrower statement of the range/limitation. In the present instance, claim 20 recites the broad recitation “…inorganic acid or organic acid”, and the claim also recites “preferably sulfuric acid, hydrochloric acid, phosphoric acid, formic acid, or acetic acid” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. Clam 18 lacks clarity because it is not expressly stated that the relevant steps according to claim 1 are carried out before the acidification. Claims 2 – 20 are rejected for being dependent upon rejected base claims. 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- 10 and 18 – 20 are is/are rejected under 35 U.S.C. 103 as being unpatentable over Elokdah et al. (J.Med. Chem, 2004, pp. 681 – 695) in view of Yu et al. (Journal of Pharmaceutical Science , 2002, pp. 2367 – 2375) . The rejected claims cover, inter alia, a preparation method for a sarcosinate, characterized by comprising: step 1, reacting a solution of glyoxylic acid or a glyoxylate with an amine solution to prepare a Schiff base solution; step 2, subjecting the prepared Schiff base solution to a hydrogenation reaction under the condition of a catalyst; and step 3, adjusting a pH value of a solution obtained after the hydrogenation reaction to be alkaline to obtain the sarcosinate. Dependent claims 2 and 4 further limits the reactants and products of step 1. Dependent claims 3, 6 and 7 further limits the reactants of step 2. Dependent claims 5 8 further limit the reaction conditions. Dependent claims 9, 10 and 18 – 20 further limit step 3. However, Elokdah discloses the reaction of glyoxylic acid with ethylamine to prepare a Schiff base solution which is subjected to hydrogenation to give N-ethyl glycine. Scheme 1, the alternative reaction prepares N- substituted amine acids 10a by the reductive amination of glyoxylic acid 12 with amines. (pp. 682, left col. Scheme 1 (d)). On page 689 in the right hand column starting at line 26 is the following reaction. The difference between the instantly claimed invention and Elokdah is as follows: adjusting the pH of the hydrogenation product in claim 1 to be alkaline; and adjusting the pH of the hydrogenation product to be acidic (claim 18). However, with regard to adjusting the pH of the hydrogenation product in claim 1 to be alkaline; and adjusting the pH of the hydrogenation product to be acidic (claim 18), adjusting the pH of an amino acid solution such as a sarcosine solution is a straightforward measure. On of ordinary skill could achieve the desired results based on common knowledge in the art. For instance, Yu discloses the use of pH adjustment on glycine during spray drying of the aqueous solution of glycine. The pH in Yu is adjusted to be either alkaline or acidic. (entire document). It would have been obvious to one of ordinary skill in the art before the effective filing date of the instantly claimed invention to prepare a Schiff base solution which is then subjected to hydrogenation to give a hydrogenation product according to the teaching of Elokdah; and then subject the hydrogenation product of Elokdah to pH adjustment in order to obtain the final salt product according to the teaching of Yu to obtain the final crystalized product. A n implicit motivation to combine exists not only when a suggestion may be gleaned from the prior art as a whole, but when the improvement’ is technology-independent and the combination of references results in a product or process that is more desirable, for example because it is stronger, cheaper, cleaner, faster, lighter, smaller, more durable, or more efficient. Because the desire to enhance commercial opportunities by improving a product or process is universal-and even common-sensical, we have held that there exists in these situations a motivation to combine prior art references even absent any hint of suggestion in the references themselves. (DyStar Textilfarben GmbH & Co. Deutschland KG v. C.H. Patrick Co., 464 F.3d 1356, 1366, 1368; 80 USPQ2d 1641, 1649, 1651 (Fed. Cir. 2006)) . In this instance in can be found in the fact that pH adjustments of amino acid solutions is a well known processing step in the art. Therefore, all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art before the effective filing date of the instantly claimed invention. KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (U.S. 2007). Claim Rejections - 35 USC § 103 Claim (s) 11 – 17 are rejected under 35 U.S.C. 103 as being unpatentable over Weiss et al. (US 5,719,319) in view of Thalhammer et al. (US 2009/0163739) , and further in view of Elokdah et al. (J.Med. Chem, 2004, pp. 681 – 695) ) and Yu et al. (Journal of Pharmaceutical Science, 2002, pp. 2367 – 2375) . The rejected claims cover, inter alia, a preparation method for a sarcosine derivative, characterized in that, a sarcosinate solution is prepared by using the preparation method of any one of claims 1-10, and the method further comprises: step 4, reacting the sarcosinate solution with cyanamide to prepare the sarcosine derivative. Dependent claim 12 further limits the sarcosine derivative to creatine, creatine monohydrate or a creatine salt. Dependent claims 13 – 17 further limit the method However, Weiss discloses a process for the preparation of creatine or creatine monohydrate, wherein cyanamide is reacted with sodium or potassium sarcosinate in water or in a mixture of water and a n organic solvent at a temperature of from 20 to 150.degree. C. and a pH value of from 7.0 to 14.0. By means of the process according to the invention of Weiss , creatine or creatine monohydrate can be prepared in good yields of from 60 to 90% by weight and with very high purity. (Abstract.). According to Weiss, it is important for the process according to the present invention that the reaction is carried out in the alkaline range from pH 7.0 to 14.0 and preferably from 9.0 to 10.0. The appropriate pH value is preferably adjusted with the aid of an inorganic or organic acid. An example of a suitable inorganic (mineral) acid is hydrochloric acid. Examples of suitable organic acids are sarcosine, acetic acid or formic acid. However, instead of these, the pH value adjustment can readily also take place with aliphatic mono-, di- or polycarboxylic acids and especially also with aromatic carboxylic acids, as well as aliphatic or aromatic sulphonic acids. (col. 2,ln 3 – 13). Examples 1 – 6 of Weiss disclose the various reaction conditions used to obtain creatine or creatine monohydrate. The difference between the instantly claimed invention and Weiss is as follows: there is no disclosure on how the sodium or potassium sarcosinate is prepare prior to use in the reaction. With regard to this difference the Examiner take the following position. The sarcosinate solution in claim 11 is basically a product obtained by a process. As such, any sarcosinate solution could be used in the process . As such any sarcosinate solution can be used in the reaction of Weiss. In support of this position the Examiner turns to the teaching of Thalhammer. Example 3 of Thalhammer produces creatin monohydrate from a sodium sarcosinate solution of Example 1 of Thalhammer. The reaction of Example 3 of Thalhammer is almost identical to Example 1 of Weiss. Further, taking in consideration the combined teaching of E l okdah and Yu, which discloses the means for preparing a sarcosinate, it would have been obvious to one of ordinary skill in the art to reasonably presume that any sarcosinate could be used , including those produced by Elokdah, to produce the desired creatine or creatine monohydrate by the process of Weiss. Furthermore, according to Weiss, i t is especially surprising that even technical solutions of sodium and potassium sarcosinate, which only have a purity of 85 to 90% by weight and contain about 10% by weight of methyliminodiacetic acid in the form of its salts as impurity, can be used for the preparation of creatine or creatine monohydrate with the above-mentioned advantages. (col. 1, ln 59 – 64). Therefore, the claims would have been obvious because the method for producing creatine or creatine monohydrates from alkali metal salts of sarcosinate was part of the ordinary capabilities of a person of ordinary skill in the art before the effective fling date of the instantly claimed invention, and in view of the teaching of the method in other situations. Art Made of Record The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. US 6,180,759 (Mencel et al.) in Example 5 discloses the preparation of N-ethylglycine using glyoxylic acid and ethyl amine. US 2009/0008813 ( Ts ai et al.) in Example 1 discloses the preparation of N-methyl glycine lithium . Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to FILLIN "Examiner name" \* MERGEFORMAT YATE' K. CUTLIFF whose telephone number is FILLIN "Phone number" \* MERGEFORMAT (571)272-9067 . The examiner can normally be reached FILLIN "Work Schedule?" \* MERGEFORMAT Monday-Friday (8:30 - 5:30) . 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, FILLIN "SPE Name?" \* MERGEFORMAT Scarlett Y. Goon can be reached at FILLIN "SPE Phone?" \* MERGEFORMAT (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. /YATE' K CUTLIFF/ Primary Examiner, Art Unit 1692
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Prosecution Timeline

Sep 12, 2023
Application Filed
Mar 27, 2026
Non-Final Rejection — §103, §112 (current)

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Prosecution Projections

1-2
Expected OA Rounds
80%
Grant Probability
99%
With Interview (+24.1%)
2y 4m
Median Time to Grant
Low
PTA Risk
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