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 .
Request for continued examination
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 01/08/2026 has been entered.
Rejections Withdrawn
Applicants’ amendments and arguments filed 12/01/2015, with respect to the rejection of claims 1-4 ,6, 7 under 35 U.S.C. § 102(a)(1) as being anticipated by Adams et al. Synthetic Communications, 1999, 2419-2430, have been considered. This rejection has been withdrawn per arguments submitted by Applicant regarding the quaternary salts compounds of prior art versus tertiary amine of instant claims.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) filed on 01/08/2026
have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
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.
Claims 1-19 are rejected under 35 U.S.C. 103 as being unpatentable over Adams et al. Synthetic Communications, 1999, 2419-2430 (cited by the Applicants in IDS).
Instant claims are drawn to a process for producing phenyl ethyl amine compounds of formula I by reaction the alcohol of formula II with (a) a cyanide under acidic conditions, followed by (b) in situ subsequent addition of water into reaction mixture of step (a) at an elevated temperature for a period of time; and obtaining the compound of formula (I) (instant claim 1); obtaining the compound of formula (I) without further reactions( instant claim 18); obtaining the compound of formula (I) without isolating a compound of formula (III) (instant claim 19).
The article by Adams et al teaches on Scheme 2 page 2423 the synthesis of phenyl ethyl amine compound 13- which corresponds to claimed formula I in which R2 is methyl, R1 is Cl, and n is 1- by reacting alcohol 12 - which corresponds to claimed formula II in which R2 is methyl, R1 is Cl, and n is 1 with NaCN/acetic acid and sulfuric acid, (i.e the cyanide salt and sulfuric acid (step a) of claims, instant claims 1, 7, 8, 16, 17) and followed by addition of water in the same reaction vessel- in situ (which corresponds to step b) of claimed process; instant claims 1-4, 7, 18, 19).
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Showed on page 2425 of the article by Adams is the experimental procedure (reproduced below):
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Regarding the limitation in-situ subsequent addition of water of instant claims, the prior art by Adams specifically teaches addition of water in the same reaction vessel without separation of the intermediate- therefore, the teaching of the prior art reads on the limitation “in situ”. Moreover, 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 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.
Regarding the limitation of claim 18 “obtaining the compound of formula (I) without further reactions”, the prior art teaches the synthesis of phenyl ethyl amine by reacting the alcohol substrate by the same steps as claimed method - therefore, the teaching of the prior art reads on the limitation “without further reactions”.
Regarding the limitation of claim 19 “obtaining the compound of formula (I) without isolating a compound of formula (III)”, the prior art teaches the synthesis of phenyl ethyl amine by reacting the alcohol substrate by the same steps as claimed method, and does not indicate isolating the aldehyde - therefore, the teaching of the prior art reads on the limitation “without isolating a compound of formula (III)”.
Regarding instant claim 5, 11-13 the prior art teaches using 200 ml of ice water (about 1:57 mol equivalents alcohol substrate: water) to quench the reaction .
Regarding instant claims 6 and 9, 10, 15 the prior art teaches the rection was conducted at 70 °C for 2 hours - the temperature is within the claimed range of 50-100°C.
The method of the present application differs from the method described in the article by Adams in that prior art teaches adding water at lower temperature instead of at elevated temperature for a period of time; the prior art teaches sodium cyanide while claim 8 requires potassium cyanide and teaches reaction temperature for the step a) of the reaction of 70°C which is outside claimed range of 75-100°C; and teaches conducting the reaction at a concentration of reagents which are outside claimed range.
Regarding the limitation of instant claims “addition of water into the reaction mixture of step (a) at an elevated temperature for a period of time”. The claims are not reciting a reference point and/ or specific temperature and time while the prior art teaches conducting the reaction at 70 °C and addition of ice-water, teaching therefore adjusting the temperature of the reaction.
As stated in MPEP 716.02 (d) regarding unexpected results commensurate in scope with claimed invention “To establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range. In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960).”
In reviewing the instant disclosure, the preparative examples on [0027] show the reaction conducted at 80°C and addition of water ta 80°C and stirring overnight.
There are no examples or data of the instant disclosure outside of range of 75-100 °C, showing criticality of instantly claimed temperature in step a) or in step b) for the synthesis of the same compound as disclosed in the prior art.
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.
Pertaining to the concentration of reagents and temperature, time of a process, it is noted that generally, differences such parameters will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such parameter is critical. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) See MPEP 2144.5.
The law is replete with cases in which the difference between the claimed invention and the prior art is some range or other variable within the claims. These cases have consistently held that in such a situation, the applicant must show that the particular range is critical, generally by showing that the claimed range achieves unexpected results relative to the prior art range. In re Woodruff, 919 F. 2d 1575, 1578 (Fed. Cir. 1990).
It is noted that potassium cyanide and sodium cyanide are univalent salts; given the similar properties, one of ordinary skill in the art would have been motivated to combine the teachings of prior art and to utilize potassium cyanide as a reagent in the reaction instead of sodium cyanide and have reasonable expectation of success in synthesizing the same compound.
One of ordinary skill in the art, would have been motivated by the teaching of Adams to carry out the reaction for the formation of the same compound by using potassium cyanide salt and to modify the reaction parameters such as temperature, concentration as part of routine optimization in order to increase the efficiency of the synthesis of the phenyl ethyl amine compounds by carrying out the reaction at lower water concentration and a controlled temperature. Moreover, the normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages (“[Discovery of an optimum value of a result effective variable in a known process is ordinarily within the skill of the art.” In re Peterson, 315 F.3d 1325, 1329 (Fed. Cir. 2003). See MPEP 2144.05.
Therefore, the prior art, and knowledge available in the art before the effective filing date provide suggestion that would have motivated the skilled artisan to explore additional cyanide salts and to adjust the temperature, time and the concentration to optimal value to maximize the yield of the phenyl ethyl amine product thereby arriving at the instantly claimed process merely by the normal course of research and development for the reasons outlined above and thereby rendering the instant claims obvious.
Thus, the instantly claimed method would have been obvious to one of ordinary skill in the art.
Conclusion
In view of the rejections to the pending claims set forth above, no claim is allowed.
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