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 1-19 are currently pending.
Claim Objections
Claims 3-4, 6, 11, and 17 are objected to because of the following informalities:
Claims 3-4, 6, and 17 recite “steps” but only recite a single step.
“stirring same” should instead read “stirring the same” in Claim 11.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
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 2, 4 and 6-19 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 regards as the invention.
Claim 2 recites “the reaction”. This phrase lacks antecedent basis as no reaction is described prior to this limitation. Therefore, “the” is unclear. The phrase “a reaction” instead would overcome the rejection. Claim 19 is rejected by virtue of dependency.
Claims 2, 4, 8, 10-11, 13, 15, and 17 recite some form of “[generic chemical class + letter]”. It is unclear if the generic class is meant to be limited to a specific group by virtue of the presence of the respective letter. For example in Claim 13, is “alkali solution C” limited to specific embodiments or is the term meant to encompass any alkali solution. Claims 6-7, 9, 14, 16, and 18 are rejected by virtue of dependency on the claims containing the ambiguous groups. All such groups are interpreted to be limited to the embodiments listed in each respective dependent claim. Claim 8 organic solvent E is interpreted to be limited to those organic solvent E embodiments of Claim 9 (despite lack of dependency). Similarly, Claim 11 is interpreted to be limited to the embodiments of Claim 12.
Claims 9 and 12 both recite and limit groups for which no antecedent basis exists. For example in Claim 9, “the catalyst” is defined but Claim 6, upon which 9 depends, does not recite any catalyst at all. Therefore, it is unclear how the limitation is meant to be applied to the preparation method. Claims 9 and 12 are interpreted to depend on Claims 8 and 11, respectively.
Claim 11 recites “an alkali solution B” and Claim 10, upon which 11 depends, also recites “an alkali solution B”. It is unclear if this solution is meant to be the same solution B or a different alkali solution B. The article “an” followed by the exact same naming convention makes the antecedent basis, if any, ambiguous. Claims 13-18 are rejected by virtue of dependency.
Claim 15 recites “an organic solvent B” and Claim 10, upon which 15 depends, also recites “an organic solvent B”. It is unclear if this solution is meant to be the same solvent B or a different organic solvent B. The article “an” followed by the exact same naming convention makes the antecedent basis, if any, ambiguous. Claims 16-18 are rejected by virtue of dependency.
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.
Claim Rejections - 35 USC § 103
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.
Claims 1 and 10-16 are rejected under 35 U.S.C. 103 as being unpatentable over Jin (WO2019240938, 2/03/2026 IDS) in view of Yu (WO2020239076, 8/06/2024 IDS, Original Chinese Document (OG) and Google Patent English Translation (ENG) cited throughout).
Jin teaches the following synthesis of Compound 51 on Page 142:
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.
Yu teaches synthetic example 1 on Page 32 (OG):
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.
Both syntheses teach the formation of similar compounds possessing essentially the same core and fundamentally the same reaction scheme past Example 51h of Jin and WX001-3 of Yu.
The synthesis of Jin in view of Yu is analyzed with respect to the rejected claims below for each claimed step:
Claim 10: Jin teaches
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wherein sodium acetate is the alkali solution. No organic solvent is taught. However, Yu teaches an analogous step with the same reacting cyanoacetyl urethane moiety:
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, wherein potassium acetate and the reactant are dissolved with N,N-dimethylacetamide (ENG: Page 50, Step 8).
Claims 11-12: Jin teaches
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, wherein 51m is dissolved in water, HCl is added, sodium nitrite is added, then N-cyanoacetyl urethane (Page 144, Step 10). Yu teaches the addition of acetic acid in the water of the first step in an analogous reaction (ENG: Page 50, Step 7):
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. Sodium acetate is added after the addition of the urethane reactant in Yu. However, it would be obvious to one of skill in the art to reverse the order of these last two steps because Yu teaches in the same synthetic step that “a solution of sodium acetate (0.1g) in water (0.5mL) was added to the reaction system, and solids were found to separate out” (Step 7). Therefore, one seeking to improve the synthesis would first add the sodium acetate before the urethane which then causes solid product to precipitate out of solution as the it is formed and thus drive the reaction of the reagents in solution forward. Because the steps of Yu and Jin are analogous and are expected to produce the same chemical modification at the same moiety of the compounds possessing a similar core, one of skill in the art would expect success in applying the Yu modifications to Jin before the effective filing date of the examined applications.
Claims 1 and 13-14: Jin teaches
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wherein the product is separated into chiral components. Sodium hydroxide and methanol are used. Jin teaches the reaction is heated to 120 degrees Celsius (Page 143, Step 8). 120 is higher than the boiling point of water (or 1N NaOH) and volatile MeOH; therefore, reflux occurs as claimed. Jin does not teach a benzoyl (Bz) protecting group being removed. Yu teaches a Bz protecting group can be used on a similar core to that of Jin and the claimed compounds in similar conditions, including KOH alkali solution and THF solvent (Page 50, Step 6). The use of a Bz PG renders obvious the second compound of Claim 1 (Protected compound of Jin
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vs. claimed
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).
Claims 1 and 15-16: Jin teaches the following reaction steps:
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, with DMSO and potassium carbonate with inert N2 gas in Step 6 and acetic acid in Step 7. Yu teaches two analogous steps also resulting in the addition of an aniline and a subsequent protecting group thereon:
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, wherein a similar salt to potassium carbonate, cesium carbonate, is used in organic solvent, N,N-dimethylacetamide (ENG: Page 50, Step 3). The protecting group is added as claimed via benzoic anhydride in the presence of acetic acid (glacial or pure acetic acid is assumed, as no other cosolvent is described) (ENG: Page 50, Step 4). Again, the protected product of Jin modified in view of Yu results in the Bz compound of Claim 1.
One of skill in the art seeking to optimize the reaction of Jin, increase the speed, or improve the yield thereof, would find it obvious to employ the similar reagents and reaction steps of Yu to modify the respective steps of Jin. One would expect successful formation of the claimed products before the effective filing date of the examined invention because both references teach effective syntheses of similar products possessing the same core and the same synthetic steps reacting similar moieties in the same order. Variable protecting groups, salts, acids, solvents which are known equivalents in the art or are taught explicitly between the two references are exchangeable for the same utilities and the substitutions thereof are prima facie obvious.
Regarding limitations directed to explicitly stirring or mixing following an “adding” step. One of skill in the art would find it obvious to mix reactants which must necessarily come into contact to react. Such stirring and mixing described throughout the Jin and Yu syntheses are expected to improve reaction efficiency.
The first compound of Claim 1 and the reaction steps of Claims 2-9 and 19 are not taught by Jin or Jin in view of Yu.
Conclusion
Claims 1-2, 4 and 6-19 are rejected. Claims 3-4, 6, 11, and 17 are objected to.
Claim 5 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Inquiries
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Richard G. Peckham whose telephone number is (703)756-4621. The examiner can normally be reached 8:30am - 4:30pm EST.
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/RICHARD GRANT PECKHAM/Examiner, Art Unit 1627
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