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 .
Continued Examination Under 37 CFR 1.114
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 allowance or after an Office action under Ex Parte Quayle, 25 USPQ 74, 453 O.G. 213 (Comm'r Pat. 1935). 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, prosecution in this application has been reopened pursuant to 37 CFR 1.114. Applicant's submission filed on 6/5/26 has been entered.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1, 3-10, 13-14, 16, 18, 20, 23 and 25-32 rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for a method of preparing compounds (III), (IV), (V), (III-a), and (IV-a) wherein R1, R2, R3, R4, R5 and R6 are selected from moieties depicted in claims 9, 10, 11, 12, 22, 24, 27, does not reasonably provide enablement for a method where R1, R2, R3, R4, R5 and R6 are selected form the moieties encompassed by the full scope of herein rejected claims. The specification does not enable any person skilled in the art to which it pertains, or with which it is nearly connected, to practice the invention commensurate in scope with these claims.
Nature of invention:
The invention is directed to multistep synthesis of chemical compound. In claims 1, the synthesis comprises reacting compound (I) and (II) to produce (III), reducing (III) to (IV). In claim 3, compound (IV) is further reacted to produce (V). Independent claim 4 is directed to the same method of claim 1, but comprises an additional step where compound (III) is reacted to alkylate the amide nitrogen to produce (III-a) and the alkylated product is carried through the rest of the steps.
Breadth of claims:
The claims are broad because of the diverse nature of the substituents in positions R1, R2, R3, R4, R5 and R6. The example below demonstrates the breadth of substituents for R3 and Ra, but they are identical for substituents R1 and R2, as well as Rb and Rc:
PNG
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588
620
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Greyscale
The scope of R1, R2, R3, R4, R5 and R6 encompasses nucleophilic groups (e.g. amines), electrophilic groups (e.g. carbonyls), groups that are reactive under claimed reaction conditions (e.g. ketones can be reduced under Pd/H2), sterically large groups (e.g. cycloalkyl substituted with cycloalkyl). In view of the divergent size and reactivity of the claimed groups, a skilled artisan would question if compounds carrying such groups would be reactive under the conditions claimed in a manner that would produce the claimed products.
State of prior art:
The claimed method is free of prior art.
Level of predictability in the art
MPEP 2164.03:
The "predictability or lack thereof" in the art refers to the ability of one skilled in the art to extrapolate the disclosed or known results to the claimed invention. If one skilled in the art can readily anticipate the effect of a change within the subject matter to which the claimed invention pertains, then there is predictability in the art. On the other hand, if one skilled in the art cannot readily anticipate the effect of a change within the subject matter to which that claimed invention pertains, then there is lack of predictability in the art. Accordingly, what is known in the art provides evidence as to the question of predictability. In particular, the court in In re Marzocchi, 439 F.2d 220, 223-24, 169 USPQ 367, 369-70 (CCPA 1971), stated:
[I]n the field of chemistry generally, there may be times when the well-known unpredictability of chemical reactions will alone be enough to create a reasonable doubt as to the accuracy of a particular broad statement put forward as enabling support for a claim. This will especially be the case where the statement is, on its face, contrary to generally accepted scientific principles. Most often, additional factors, such as the teachings in pertinent references, will be available to substantiate any doubts that the asserted scope of objective enablement is in fact commensurate with the scope of protection sought and to support any demands based thereon for proof.
In the currently claimed method, the reagents comprise substituents that would cause a skilled artisan to question their effect on the claimed chemical transformations. The substituents comprise groups that are themselves capable of reacting under the claimed conditions. For example, in preparation of compound (IV) from compound (III), groups other than the NO2 can be reduced. Groups such as carbonyl containing compounds. In another example, preparation of compound (III-a) requires a nucleophilic substitution of a halogen attached to R6. However, XR6 comprises compounds that would not be reactive or even stable such as XOH. Also compound III comprises groups that are more nucleophilic than the amide nitrogen and would preferentially react with XR6, such as primary amines (alkyl substituted with NH2).
Amount of direction and working examples:
Working examples comprise non-reactive aryl halogens and small alkyl groups as substituents for R1, R2, R3, R4, R5 and R6. These are the substituents found in claims 9, 10, 11, 12, 22, 24 and 27.
Quantity of experimentation:
To enable practice the full scope of invetion, a skilled artisan would need to devise a synthetic protocol and prepare the thousands of starting materials and test each combination of starting materials in the claimed synthetic method. The amount of experimentation is immense. Due to unpredictability that is inherent in chemical synthesis and a limited exemplified scope of substituents, a skilled artisan would not be able to practice the full scope of the claimed method without undertaking a significant quantity of undue experimentation.
Claim objections
Claims 11, 12 and 22 are objected to as being dependent on a rejected claim.
Allowed claims
Claim 24 is allowed.
Conclusion
Claims 1, 3-10, 11-14, 16, 18, 20, 22-24 and 25-32 are pending
Claims 1, 3-10, 13-14, 16, 18, 20, 23 and 25-32 are rejected
Claims 11, 12 and 22 are objected to
Claim 24 is allowed
Any inquiry concerning this communication or earlier communications from the examiner should be directed to YEVGENY VALENROD whose telephone number is (571)272-9049. The examiner can normally be reached Mon-Fri 9am-5pm.
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/YEVGENY VALENROD/Primary Examiner, Art Unit 1628
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