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
Claims 1-29 are pending in the instant application.
Claims 1, 3, 4, 7, 10, 12, 14, 15, 17, 18, 20, 23, 25, and 27 are amended.
Claim 9 is cancelled.
Claims 30-42 are new.
Claims 1-8 and 10-42 are examined herein.
Priority
The instant application claims benefit of foreign priority to PCTCN2019090258, filed on 06 June 2019, and the benefit of priority to PCT/ep2020/065424, filed on 04 June 2020. The claims to the benefit of priority are acknowledged. As such, the effective filing date of the claims is 06 June 2019.
Information Disclosure Statement
The information disclosure statement (IDS), submitted on 28 August 2025, is acknowledged and considered. The submissions are in compliance with the provisions of 37 CFR 1.97.
Response to Arguments
The amendment filed on 28 August 2025 has been entered.
With respect to the first 112(b) rejection, applicants amendments have been considered but do not fully resolve the issue. Claims 1 and 4 recite compound (II) which still contains an additional CH-2 group. Therefore the rejection is maintained but modified below in light of Applicant’s amendments.
In view of applicant amendment to claim 1 and 4, the second 112(b) rejection of record is withdrawn.
In view of applicant amendment to claim 1, the 102(a)(1) rejection of record is withdrawn.
In view of applicant amendment to claim 1, the 103 rejection of record is withdrawn.
In addition, new 112 (b) rejections, 103 rejections and objections are necessitated by amendment (see below).
All rejections and objections not found below have been withdrawn.
MAINTAINED REJECTIONS
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 1-8 and 10-42 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claims 1 and 4 recite the compound of formula (I) as having the structure pictured below. The preparation step a) contains an extra CH2 group between R3 and the amine in compound (II) (circled in picture below). The dependent claims 2, 3, 5-8, and 10-42 do not resolve the issue and are therefore subject to the rejection as well. To overcome the rejection Applicant is advised to amend Formula (I) to include the CH2 group or amend compound (II) to eliminate the extra CH2 group. For examination purposes, the claims have been interpreted based on Formula (I).
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NEW REJECTIONS FACILLITATED BY AMENDMENT
Claim Objections
Claims 1-4 are objected to because of the following informalities:
Several structural formulae are unclear as the text has shifted in the images. Particularly, Formula (I), compound (IV), formula (XIV), formula (XI), formula (XII), formula (XII), formula (XVI), formula (XVII), formula (XVIII), formula (XIX), the compounds of claim 3, and formula (X).
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.
Claim 22 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 22 recites the limitation "wherein the reagent is selected from CDI, phosgene, diphosgene, disuccinimidyl carbonate, and triphosgene.” There is insufficient antecedent basis for this limitation in the claim as claim 4, from which it depends, only recites CDI and disuccinimidyl carbonate.
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.
Claims 1-8, 10-17, and 20-42 is/are rejected under 35 U.S.C. 103 as being unpatentable over Chen (WO2017140750A1) in view of de Figueiredo (Adv. Synth. Catal. 2017; 359: 1963).
Regarding claims 1 and 4, Chen discloses synthetic steps for compounds of the instant Formula (I). Scheme 1 (page 6) shows reaction steps for V
→
VI
→
VII
→
VIII
→
IX
→
X, corresponding to the instant steps c), d), e), f), and g). Scheme 2 (page 7) shows reaction steps for XI
→
XII
→
XIII
→
XIV
→
XVI
→
XVII
→
XVIII
→
I, corresponding to the instant steps h), i), j), k), l) and m).
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Chen does not disclose the preparation steps a) and b). Instead Chen discloses the formation of an isocyanate from compound (II) using a phosgene reagent and then the formation of the urea from the isocyanate in reference step b.
De Figueiredo discloses the method of preparing the instant compound (III), reference compound 2a, from instant compound (II), reference compound 1a, using 1,1’-carbonyldiimidazole (CDI) (Scheme 2), corresponding to step instant step a). De Figueiredo also discloses a second step leading to the formation of a urea (pictured below).
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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.
In this case at least prong B of KSR applies – substitution of one known element for another. Both Chen and de Figueiredo teach methods of forming a urea via instant compound (II). Chen uses instant compound (II) and phosgene to produce an isocyanate to form the urea (V). De Figueiredo uses instant compound (II) and CDI to produce instant compound (III), which can then be use to form a urea. As phosgene is toxic, one skilled in the art would be motivated to modify the synthetic scheme of Chen to that of de Figueiredo by using de Figueiredo’s method of forming the instant compound (III) and reacting that with Chen’s compound (IV) to produce the instant urea (V).
Thus, all of the elements of claims were known to one of ordinary skill in the art at the time the invention was made 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 nothing more than predictable results to one of ordinary skill in the art at the time of invention. Therefore, the claimed invention, as a whole, would have been obvious to one of ordinary skill in that art at the time the invention was made.
Regarding claim 2 and 5, Chen discloses R1 is phenyl optionally substituted with 1-3 halogen or C1-6- -alkyl substituents, R2 is C1-6- -alkyl, and R3 is CxH2x where x is 1, 2, 3, 4, 5, 6, or 7.
Regarding claim 3, Chen discloses example 10 (page 30) and example 13 (page 35), pictured below, respectively.
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Regarding claim 6, Chen discloses compound X as a hydrochloride salt (page 27).
Regarding claim s7, 20, and 22, de Figueiredo teaches the formation of instant compound (III) is performed in the presence of a base in a solvent with CDI (Scheme 1). The solvent taught is DCM (Figure 1).
Regarding claims 8 and 21, de Figueiredo teaches the base to be TEA (Scheme 2).
Regarding claims 10 and 23, Chen teaches the formation of the hydantoin is performed in the presence of a suitable acid in a suitable organic solvent; wherein the solvent is 2-MeTHF, IPAc, EA, toluene and DCM
(page 13, line 19-24)
Regarding claims 11 and 24, Chen teaches the acid in the formation of the hydantoin is selected boron trifluoride etherate, phosphoric acid, sulfuric acid, HBr and HCl (page 13, line 26)
Regarding claims 12, 13, 25 and 26, Chen discloses the formation of a compound of formula VIII was performed in the presence of a Lewis acid and a reducing agent, wherein the Lewis acid is BF3 · Et2O, and the reducing agent is borane (page 25, line 6).
Regarding claims 14 and 27, Chen discloses the formation of a compound of formula IX was performed in the presence of methanol mixed with water (page 26, line 6).
Regarding claims 15, 16, 28 and 29, Chen discloses the formation of a compound of formula X in the presence of HCl in a solvent, where the solvent is MIBK (page 27, line 6).
Regarding claim 17, Chen discloses the acid of Formula (XV) can be (+)-CSA, (S)-(+)-1,1-Binaphthyl-2,2'-diyl hydrogen phosphate and (R)-(-)-1,1-Binaphthyl-2,2'-diyl hydrogen phosphate (page 18).
Regarding claim 30, de Figueiredo teaches the formation in the presence of DCM and TEA. In the absence of criticality, the substitution of anisole for DCM would be routine optimization. See MPEP 2144.05.II.A.
Regarding claims 31-41, in the absence of criticality, the substitution of solvents, acids, and bases as taught by Chen for those recited in the instant claims would be routine optimization. See MPEP 2144.05.II.A.
Regarding claim 42, Chen discloses compound (V) (pictured below), which is the sodium salt of the instant recited compound.
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Conclusion
Claims 1-8 and 10-42 are rejected.
Claims 1-4 are objected to.
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 nonprovisional extension fee (37 CFR 1.17(a)) 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 mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jerica K Wilson whose telephone number is (703)756-4690. The examiner can normally be reached Monday-Friday 9:00-5:00.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached at (571)270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/J.K.W./Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
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