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 .
Status of the Application
Claims 1-20 are pending.
Election/Restrictions
Applicant's election with traverse of Group I, claims 1-14 and 19-20, directed to a process of making amide, and the species:
PNG
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899
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in the reply filed on 07/21/2026 is acknowledged. The election was made with traverse.
The election of species requirement (A) for Group I, as set forth in the Office action mailed on 12/18/2025, has been reconsidered and is hereby withdrawn.
The traversal is on the ground(s) that Pithani is silent about using Dean-stark apparatus. This is not found persuasive. Please see the rejection as set forth below.
The requirement is still deemed proper and is therefore made FINAL.
Claims 15-18 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Please note that after a final requirement for restriction, the Applicants, in addition to making any response due on the remainder of the action, may petition the Commissioner to review the requirement. Petition may be deferred until after final action on or allowance of claims to the invention elected, but must be filed not later than appeal. A petition will not be considered if reconsideration of the requirement was not requested. (See § 1.181.).
Applicant is reminded that upon the cancellation of claims to a non-elected invention, the inventorship must be amended in compliance with 37 CFR 1.48(b) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. Any amendment of inventorship must be accompanied by a request under 37 CFR 1.48(b) and by the fee required under 37 CFR 1.17(i).
Claims 1-14 and 19-20 are under current examination.
Claim Objections
Claims 1 and 7 are objected because of presence of reaction scheme in the claims. See 37CFR 1.58.
Appropriate correction is required.
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-14 and 19-20 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, or for pre-AIA the applicant regards as the invention.
Claims 1-14 and 19-20 are indefinite as claims1-11 recite alternative in an improper open ended Markush group. For instant, “selected from the group comprising”. It is unclear what other alternatives are included in the group. The scope of claims is unclear. Applicant is suggested to amend the claim in a proper Markush format, such as, “selected from a group consisting of”.
Since the dependent claims 12-14 and 19-20, does not cure the above deficiencies, these claims are also indefinite.
Appropriate correction 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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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.
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.
Claims 1-14 and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Pithani (Org. Process Res. Dev. 2019, 23, 1926-1931; as provided by the applicant on IDS dated 10/15/2023), Maki (Tetrahedron; 63, 2007, 8645-8657) and Cordova (US20170174618 A1) in combination.
Determining the scope and contents of the prior art
Pithani teaches large scale (>1Kg) enzymatic synthesis of amides by reacting amine with acid or ester of same formula as II of the instant claims (with example of isopropyl acetate) using lipase as enzyme (with example Novozym 435, which is a lipase from Candida antarctica), which is immobilized on a rotary bed (with examples of 10 wt% and 20wt%) reactor at 50C (reads on temperature of the instant claims) in presence or absence of any solvent (isopropyl acetate with no additional solvent) (entire article). Further, the cited prior art recognizes problem in the process due to presence of water formed as a side product (see page 1928, under heading Observation).
Ascertaining the differences between the prior art and the claims at issue
Pithani teaches large scale (>1Kg) enzymatic synthesis of amides by reacting amine with acid or ester of same formula as II of the instant claims (with example of isopropyl acetate) using lipase as enzyme (with example Novozym 435, which is a lipase B from Candida antarctica), which is immobilized on a rotary bed, but fails to teach using Dean stark apparatus in addition to rotatory bed; using amine as in the instant claims; and pressure for carrying out the process.
Resolving the level of ordinary skill in the pertinent art
With regards to the difference of using Dean stark apparatus in addition to rotatory bed-Pithani recognizes problems in the process because of formed side product water and suggestion of removing it. However, the cited prior art is silent about Dean stark apparatus.
This deficiency is cured by Maki.
In the same field of endeavor of making amide, Maki teaches synthesis of same amide using same amine and same acid/ester as in the instant claims and provides need for removal of water formed as a side product using Dean-stark for dehydration (entire article).
Thus, with the guidance provided by the cited prior art, it would have been prima facie obvious to a person of ordinary skill in the art to remove side product water from the reaction using commonly used protocols in the art, such as Dean-Stark process as taught and used by Maki in formation of amide.
With regards to using amine as in the instant claims; and pressure for carrying out the process. Pithani gives examples with using different amines and acids/ester in making amides. However, amine used by Pithani differs from the instant claims and Pithani is silent about pressure in the reaction. This deficiency is cured by Cordova.
In the same field of endeavor of making amide, Cordova teaches enzymatic synthesis of amides of same formula as III by reacting same amine as formula I with acid or ester of same formula as II of the instant claims using lipase as enzyme (with example Novozym, which is a lipase B from Candida antarctica), at 45C (reads on temperature of the instant claims) and under atm pressure (=0.10325Mpa) (reads on pressure of the instant claims) (entire application, especially, page 8). Thus, with the guidance provided by the cited prior art, it would have been prima facie obvious to a person of ordinary skill in the art that lipase may catalyze condensation of different amines and acid/ester as in the instant claims to form amide of the instant claims as taught by Cordova and condensation of different amines and acid/ester to form amide as taught by Pithani.
Further, Case law has established that it is prima facie obvious to simply employ a different starting material in a generally old reaction. In re Farkas and Sorm 152 USPQ 109 (1966).
Further, based on teaching of Cordova and Pithani, it would have been prima facie obvious to a person of ordinary skill in the art that lipase catalyzed reaction may be carried out at atmospheric pressure. Thus, the cited prior art meets limitation of the instant claims.
Therefore, combination reads applicants claims.
Based on the above established facts, it appears that the combination of teachings of above cited prior art read applicants’ process.
Therefore, all the claimed elements were known in the prior art and one skilled person 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 at the time of the invention.
Considering objective evidence present in the application indicating obviousness or nonobviousness
To establish a prima facie case of obviousness, three basic criteria must be met: (1) the prior art reference must teach or suggest all the claim limitations; (2) there must be some suggestion or motivation, either in the references themselves or in the knowledge generally available to one of ordinary skill in the art, to modify the reference or to combine reference teachings; and (3) there must be a reasonable expectation of success; and (MPEP § 2143).
In this case, Pithani teaches large scale (>1Kg) enzymatic synthesis of amides by reacting amine with acid or ester of same formula as II of the instant claims using lipase as enzyme, which is immobilized on a rotary bed and Maki teaches synthesis of same amide using same amine and same acid/ester as in the instant claims and provides need for removal of water formed as a side product using Dean-stark for dehydration, whereas Cordova teaches enzymatic synthesis of amides of same formula as III by reacting same amine as formula I with acid or ester of same formula as II of the instant claims using lipase as enzyme, at 45C and under atm pressure.
So, the combination of prior art read applicants claims.
In KSR International Vo. V. Teleflex Inc., 82 USPQ2d (U.S. 2007), the Supreme Court particularly emphasized “the need for caution in granting a patent based on a combination of elements found in the prior art,” (Id. At 1395) and discussed circumstances in which a patent might be determined to be obvious. Importantly, the Supreme Court reaffirmed principles based on its precedent that “[t]he combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results.” (Id. At 1395). See MPEP 2143 - Examples of Basic Requirements of a Prima Facie Case of Obviousness [R-9].
In this case at least prong (E) “Obvious to try” – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success would apply.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense. In that instance the fact that a combination was obvious to try might show that it was obvious under § 103.”KSR, 550 U.S. at ___, 82 USPQ2d at 1397. If any of these findings cannot be made, then this rationale cannot be used to support a conclusion that the claim would have been obvious to one of ordinary skill in the art. Further, there is a reasonable expectation of success that Dean-Stark apparatus may be employed to carry out removal of side product and can be made by combination of the above cited prior art.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention by taking the advantage of the teaching of the above cited references and to make the instantly claimed process with a reasonable expectation of success. Modifying such parameters is prima facie obvious because an ordinary artisan would be motivated to develop an alternative process for economic reasons or convenient purposes from a known individual reaction steps, and to arrive applicants process with a reasonable expectation of success, since it is within the scope to modify the process through a routine experimentation.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PANCHAM BAKSHI whose telephone number is (571)270-3463. The examiner can normally be reached M-Thu 7-4.30 EST.
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/PANCHAM BAKSHI/Primary Examiner, Art Unit 1623
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