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 preliminary amendment, filed July 31, 2023. As filed Claims 1-15 are pending.
Priority
This application filed 07/31/2023 is a National Stage entry of PCT/FR2022/050165 , International Filing Date: 01/31/2022 claims foreign priority to FR2100997, filed 02/02/2021.
Information Disclosure Statement
Applicants' information disclosure statement (IDS) filed 7/31/2023 have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herein.
Claim Objections
Claims 2-5, 8, 13-14 are objected to because of the following informalities: the capitalized term “Claim” should be changed to lower case for consistency.
In Claim 14 the terminology “in particular” should be deleted to address potential indefiniteness issues.
In Claim 15 should amended to specify that the “w-aminoalkanoic acid obtained” in step ii) of claimed method to address potential indefiniteness issues.
In claim 1, the recitation “pressure, from” should be changed to “pressure ranging from” for consistency in claims terminology.Appropriate correction is required.
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 1-15 are rejected under 35 U.S.C. 103 as being unpatentable over Adams et al. EP2358662B1, July 39, 2914 by Pees et al. (“the ‘662 publication”; cited by the Applicants in IDS; machine translation provided in PTO892 attached herewith).
Instant claims are drawn to a process the manufacture of ա-aminoalkanoic acid of formula NH2-(CH2)n-COOH, in which n is an integer from 9 to 11, by reaction of the
corresponding ա -bromoalkanoic acid with ammonia, comprising:
i) reaction of the ա -bromoalkanoic acid with an aqueous excess ammonia solution, and
ii) separation of the w-aminoalkanoic acid formed from the reaction mixture, 70% by weight, and stage i) is carried out under a pressure greater than atmospheric
pressure, from 0.11 to 2.0 MPa absolute.
The ‘662 publication teaches a process for the ammonolysis in the presence of ammonia of 11-bromoundecanoic acid which corresponds to claimed formula in which n is 11, carried out under conditions making it possible to limit the secondary reactions causing the impurities and considerably reducing the reaction time . The preparation of 10-aminodecanoic acid which corresponds to claimed formula NH2-(CH2)n-COOH in which n is 11 consisting in reacting 11-bromoundecanoic acid in an aqueous ammonia solution - which corresponds to step i) of the claimed process- containing 25% by weight of this solution, using a large excess of ammonia, stirring the mixture and to maintain at about 15 ° C to give the product a yield of 77% upon separation which corresponds to step ii) of the claimed process (page 2-3 of translation).
Regarding instant claims 2-5, the ‘662 teaches the reaction carried out in a reactor bank connected in parallel each of the reactors being subjected to a variable temperature and further that the reaction is conducted at a temperature of 60 ° C to 100 ° C., initial temperature of the ammonolysis reaction of 11-bromoundecanoic acid governs the formation of secondary species; therefore it’s not necessary to conduct the reaction in a low-temperature isotherm, but to subject the medium to a steady temperature rise while observing an initial low-temperature plateau (15 to 25 ° C) wherein the process involves i) a step of dispersion of 11-bromoundecanoic acid, in an aqueous solution of ammonia, the ammonia being in excess and ii) a step of ammonolysis by reaction of 11-bromoundecanoic acid with ammonia, under conditions of stirring of the reaction medium and of progressive heating thereof, sufficient to allow the production of 11-aminoundecanoic acid with a total consumption of 11-bromoundecanoic acid in less than 80h (page 3)
Regarding instant claims 1, 6-7, the ‘662 publication teaches that step i) is carried out by dispersion of 11-bromoundecanoic acid (Br11) at a temperature of 60 ° C. to 100 ° C., in concentrated ammonia – e.g. 20 to 50% by weight, in excess with respect to Br11 (a molar ratio Br11: NH 3 of between 1:10 and 1:60, preferably of 1:30) at a temperature ranging from 0 ° C. to 10 ° C (page 5).
Regarding instant claim 10, the ‘662 teaches the reaction carried out continuously in a reactor bank connected in parallel (page 4).
Regarding instant claim 11, the 662 publication teaches on page 6 batchwise (batch mode) option for conduction the ammonolysis,
Regarding the limitation pressure of the process of instant claims 1,8, 9, the prior art teaches that the reaction is carried out under atmospheric pressure (not calimed).
The method of the present application differs from the method described in the ‘662 publication in that prior art teach that ammonolysis of 11-bromoundecanoic acid, carried out at ambient pressure for the formation of the same compound the ա-aminoalkanoic acid of formula NH2-(CH2)n-COOH, in which n is 11, instead of reaction pressure greater than atmospheric pressure, from 0.11 to 2.0 MPa absolute as required by the claimed process.
Pertaining to the pressure 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).
One of ordinary skill in the art, would have been motivated by the teaching of the ‘662 publication to carry out the reaction for the formation of the same compound by modifying the reaction parameters such as pressure as part of routine optimization in order to increase the efficiency of the synthesis of the ա-aminoalkanoic acid by carrying out the reaction at low a controlled pressure. Moreover, the normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine the optimal pressure for the reaction. (“[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 adjust the pressure of the reaction to optimal value to maximize the yield of the ա-aminoalkanoic acid 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
Claims 1-15 are rejected.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANA MURESAN whose telephone number is (571)-270-7587. The examiner can normally be reached on Monday through Friday, 8:30 am to 5:30 pm EST.
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 an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/ANA Z MURESAN/Primary Examiner, Art Unit 1692
Prosecution Insights