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 .
DETAILED ACTION
This Office Action is responsive to Applicant's Remarks/After Non-Final rejection, filed Oct. 22, 2025. As filed, claims 1, 3-8, 10-21 are pending; of which, claims 1, 3, 8 are currently amended. Claims 11-21 are newly added.
Response to Remarks
Applicant’s amendments have been fully considered and are entered. The status for each rejection and/or objection in the previous Office Action is set out below.
1.The rejection of claims 1-10 under 35 U.S.C. § 112 second paragraph is withdrawn per amendment to claims to specify the step of recovering the compound of formula I.
2.The rejection of claims 1-4, 7, 8, 10 under 35 U.S.C. § 102(a)(1) as being anticipated by WO 2020/161074 Al 13 August 2020, by Bilz et al is withdrawn per claim amendments to exclude “OH” from definition of variable Y of formula II.
3.The rejection of claims 1, 5, 7, 10 under 35 U.S.C. § 102(a)(1) as being anticipated by JP 03093757, 1991 et al is withdrawn per claim amendments to exclude “OH” from definition of variable Y of formula II.
4.The rejection of claims 1, 4, 7, 10 under 35 U.S.C. § 102(a)(1) as being anticipated by WO 2001060790, 2001, by Ponceblanc is withdrawn per claim amendments to exclude “OH” from definition of variable Y of formula II.
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5.The rejection of claims 1-8, 10 under 35 U.S.C. § 103 over WO 2020/161074 Al 13 August 2020, by Bilz et al. is withdrawn per claim amendments.
6. The objection to claims has been addressed by amendment.
The following are modified or new grounds of rejections necessitated by Applicants’ amendment, filed on 10/22/2025. The limitations in the amended claims have been changed and the breadth and scope of those claims have been changed.
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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
1.Claims 1, 3-8, 10-12 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2001060790, 2001, by Ponceblanc (“the ‘790 publication” cited by Applicants in IDS) in view of WO2004/089863A (“the 863 publication”; cited by Applicants in IDS).
Instant claim1 are drawn to a method for preparing a compound of formula I,CH3XCH2CH2C(NH2)COOH (I) where X is S or Se,
by catalytic conversion of a compound of formula II
CH3XCH2CH2C(Y)CN (II) where X is S or Se and Y is NH2,
wherein the reaction medium comprises the compound of formula II, water, and
least one catalyst comprising at least alumina, titanium dioxide or a mixture thereof;
the conversion is performed in a single step; and
then recovering the compound of formula I.
The ‘790 publication teaches preparation of methionine which corresponds to claimed formula I in which X is sulfur S by liquid phase hydrolysis of H2NCR1R2CN - in which when R1,R2 = H, correspond to claimed formula II in which X is sulfur S and Y is NH2 by contacting with water in presence of titanium dioxide (instant claim 1). The catalyst has BET of 30-150m2/g (page 2; instant claim 4). The reaction is carried out at 80-130 deg. Celsius (page 3 lines 5-10; instant claim 7) The ratio of the catalyst to amide of 1g catalyst per gram methionine amide (example 2, Table 2; instant claim 5). The catalyst may comprise titanium as the sole metal or may comprise one or more additional metals (instant claims 3 and 11). The reaction is caried out in batch or continuously (page 3 lines 12-14, instant claim 10); abstract, examples, claims). The molar amount of ammonia relative to 2-hydroxy-4-methylthio butanenitrile is ranging from 3 to 10 (instant claim 6). Regarding instant claims 8, the 790 publication teaches contacting 2-hydroxy-4-methylthio butanenitrile with ammonia or a solution containing ammonia to produce a first product stream comprising 2- amino-4-methylthio butanenitrile (page 4).
The method of the present application differs from the method described in the ‘790 publication in that prior art does not teach that the reaction is performed in a single step in one and same reactor.
With regards to the limitation “the conversion is performed in a single step” based on the teachings of prior art, one of ordinary skills in the art would have found obvious to conduct the reaction as one-pot/one-step reaction because one-pot synthesis is a strategy where reagents are subjected to successive transformation in one reaction vessel is routinely used in chemical art to avoid separation and purification of intermediates, to increase efficiency and overall yield of reactions.
Moreover, the ‘863 publication, also drawn to the preparation of methionine which corresponds to claimed formula I in which X is sulfur S by reacting 2-hydroxy-4-(methylthio)butyronitrile – which corresponds to claimed formula II, wherein the catalytic hydrolysis of the nitrile to the ammonium salt of the ' 2-hydroxy-4-methylthiobutyric acid and teaches that the reaction is performed in a single process step and in one reactor (see claim 1; example 1 of the ‘863 publication). Therefore, the prior art relied upon, and knowledge generally available in the art before the effective filing date provide the suggestion that would have motivated the skilled artisan to conduct the reaction in one step in one reactor.
The rationale to support a conclusion that the claim would have been obvious is that 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 yielded nothing more than predictable results to one of ordinary skill in the art. KSR, 550 U.S. at ___, 82 USPQ2d at 1395; Sakraida v. AG Pro, Inc., 425 U.S. 273, 282, 189 USPQ 449, 453 (1976);
The Applicant has not shown evidence of substantially improved and unexpected results between the instantly claimed process and the prior art process for producing the same compound from same starting materials and reagents by same steps.
Please note that if Applicant intends to rely on unexpected or unforeseen results, attention is invited to MPEP 716.02. Absent clear, convincing, side-by-side data demonstrating unobviousness vis-a-vis the prior art commensurate with the scope of protection sought and showing that the claimed process and process disclosed by prior art are distinct, the claims are considered prima facie obvious..
2.Claims 13-21 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2020/161074 Al 13 August 2020, by Bilz et al. (cited by Applicants in IDS) and WO2004/089863A (“the 863 publication”; cited by Applicants in IDS)
Instant claims 13-21 are drawn to a method for preparing a compound of formula I,CH3XCH2CH2C(NH2)COOH where X is S or Se, wherein the method comprises the steps of catalytically converting a compound of formula II CH3XCH2CH2C(Y)CN (formula II), where X represents S or Se and Y represents OH, the reaction medium comprises the compound of formula II, water, at least one catalyst and NH3 or an ammonium salt, the conversion is performed in a single step, the catalyst comprises at least alumina, titanium dioxide, zirconia or a mixture thereof; and then recovering the compound of formula I.
The ‘074 publication teaches a method for preparing methionine, which corresponds to claimed formula I in which X is sulfur S, by catalytic conversion of the compound MMP-CN which corresponds to claimed compound with the formula (II)
where X is sulfur and Y is OH in presence of water and ammonia mediated by catalyst comprising alumina, titanium dioxide, the catalyst containing 60.0 to 99.5 wt.% ZrO2 stabilized with an oxide of the element Hf and at least one oxide of the element M, wherein M = Ce, Si, Ti or Y; and isolation of methionine by crystallization
(seeclaims 1, 3, 9, 10, 21 of the cited reference; scheme on page 9; instant claims 13, 15, 21).
Regarding the limitation “the conversion is performed in a single step”, the ‘074 publication teaches in example 1 on page 14 the synthesis of 2-amino-4-(methylthio)butanenitrile from 2-hydroxy-4-(methylthio)butanenitrile conducted in a glass reactor and sealed subsequently; the resulting solution was analyzed by HPLC chromatography100% conversion of MMP-CN with a selectivity of 98.8% towards 2-amino-4-(methylthio)butanenitrile.
Furthermore, with regards to the limitation “the conversion is performed in a single step” based on the teachings of prior art, one of ordinary skills in the art would have found obvious to conduct the reaction as one-pot/one-step reaction because one-pot synthesis is a strategy where reagents are subjected to successive transformation in one reaction vessel is routinely used in chemical art to avoid separation and purification of intermediates, to increase efficiency and overall yield of reactions.
Moreover, the ‘863 publication, also drawn to the preparation of methionine which corresponds to claimed formula I in which X is sulfur S by reacting 2-hydroxy-4-(methylthio)butyronitrile – which corresponds to claimed formula II, wherein the catalytic hydrolysis of the nitrile to the ammonium salt of the ' 2-hydroxy-4-methylthiobutyric acid and teaches that the reaction is performed in a single process step (see claim 1; example 1 of the ‘863 publication). Therefore, the prior art relied upon, and knowledge generally available in the art before the effective filing date provide the suggestion that would have motivated the skilled artisan to conduct the reaction in one step.
The method of the present application differs from the method described in the ‘074 publication in that prior art teaches a different concentration of the catalyst and of the reagents for the formation of the same compound.
Regarding instant claim 14 the ‘074 publication teaches that the catalyst is treated with a doping material alkali metals and alkaline earth metals (see claim 16 of prior art).
Regarding instant claim 16 the ‘074 publication teaches the catalyst characterized by BET specific area of 125 m2/g ( page 13, col 5-35, Table 3 page 18).
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Regarding instant claim 17 the ‘074 publication teaches concentration of the catalyst 0.18 mol eq Zr)2-catalyst stabilized with 4 wt.% Y2O3 and containing 2 wt.% HfO2 (examples 4-8 on page 15 and Table1).
Regarding instant claim 18, the ‘074 publication teaches that the conversion is carried out at a temperature ranging from 70 °C - 200 °C which is within the claimed range (claim 13 of prior art).
Regarding instant claim 20, the ‘074 publication teaches that it that the reaction can be carried out in a continuous mode (claim 19 of prior art).
With regards to the limitation drawn to the amount of catalyst varying from 0.18 molequiv and the substrate concentration of 18 wt.% and varying such condition to optimize the reaction ( examples 1-19, 28-34; Tables). Consequently, one of ordinary skill in the art would have been motivated to utilize an optimal amount of substrate and catalyst as suggested in the teachings of the prior art. It is noted that merely modifying the process conditions such as temperature and concentration is not patentable modification absent of a showing of criticality. See In re Aller, 220 F.2d 454, 105 USPQ 233 (CCPA 1955). See also MPEP § 2144.05. Moreover, the adjustment of conventional working conditions (e.g., determining result effective amounts of the ingredients beneficially taught by the cited references) is deemed merely a matter of judicious selection and routine optimization which is well within the purview of one of ordinary skill in the art.
The rationale to support a conclusion that the claim would have been obvious is that 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 yielded nothing more than predictable results to one of ordinary skill in the art. KSR, 550 U.S. at_, 82 USPQ2d at 1395; Sakraida v. AG Pro, Inc., 425 U.S. 273, 282, 189 USPQ 449, 453 (1976); Anderson's-Black Rock, Inc. v. Pavement Salvage Co., 396 U.S. 57, 62-63, 163 USPQ 673, 675 (1969); Great
Atiantic & P. Tea Co. v. Superrnarket Equiprnent Corp., 340 U.S. 147, 152, 87 USPQ 303, 306 (1950).
Thus, the claimed invention as a whole is prima facie obvious over the teachings of the prior art.
Conclusion
In view of the rejections to the pending claims set forth above, no claim is allowed.
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 extension fee 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 date of this final action.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to:
Ana Muresan
(571) 270-7587 (phone)
(571)270-8587 (fax)
Ana.Muresan@uspto.gov
The examiner can normally be reached Monday - Friday (9:00AM - 5:30PM).
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.
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692