Detailed Action
This office action is in response to applicant’s communication filed on 12/19/25.
Claims 73-80 are pending in this application and are being examined in this Office Action.
In a telephone conversation with Ying Chen on 6/17/26, the examiner suggested examiner’s amendments to overcome the objections and 112 rejection. However, the examiner was not successful.
Priority
The applicant claims benefit as follows:
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Objections
Claims 74-75, 77 and 79 are objected to because of the following informalities:
Claims 74-75, 77 and 79 are objected to because some of the words are cut off near the chemical figures. For example in claim 74, the “g” in “reacting” is cut off and there appears to be a lone “c.” near the end of claim 74.
Claims 75 and 77 are objected to because of inconsistency in the claimed reaction sequence with applicant’s disclosure (see applicant’s PGPub).
Claim 75 recites that reacting the mesylate compound "with an azide" forms the aminomethyl product, but Figure 1 and paragraph [1117] of applicant’s PGPub, show azide substitution followed by a separate H2/Pd-C reduction to form the amine.
Claim 77 recites that the mesylate compound is reacted with NaN3 in the presence of H2, but applicant’s PGPub shows sequential operations: NaN3 substitution to form the azide intermediate, followed by reduction under H2 with Pd/C.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation 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.
Claims 73-80 are rejected under 35 U.S.C. 112(a) as based on a disclosure (see applicant’s PGPub) which is not enabling. The disclosure does not enable one of ordinary skill in the art to practice the invention without the reaction steps and reactants in both claims 74 and 75, which recite forming the mesylate by reacting the alcohol reactant with mesyl chloride and then reacting the mesylate with an azide compound. These reaction steps are essential to the conversion to the claimed aminomethyl product. They are critical or essential to the practice of the invention but are not included in claim 73. See In re Mayhew, 527 F.2d 1229, 1233, 188 USPQ 356, 358 (CCPA 1976).
Claim 73 recites only the starting hydroxymethyl compound and the desired aminomethyl product, without reciting the chemical steps that give the conversion. Claims 74 and 75 include the specific sequence: reaction of the alcohol with mesyl chloride to generate the mesylate, followed by reaction of the mesylate with an azide.
The disclosure shows the essential nature of the multi-step process. Paragraph [0270] states that reaction of the diol with tert-butyldiazoacetate affords a 2-tert-butoxy-2-oxoethoxy derivative, which may be converted to an amine via the azide. Figure 1 (see below) shows conversion of the alcohol to the mesylate with MsCl, followed by (1) NaN3 substitution and (2) reduction under H2/Pd-C to give the aminomethyl intermediate. The procedure in paragraphs [1116]-[1117] also forms the mesylate with methanesulfonyl chloride, reacts that mesylate with sodium azide, and then reduces the resulting material under H2 with Pd/C to obtain the aminomethyl product.
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Thus claim 73 omits essential reaction steps or reactants in applicant’s invention. The omitted limitations are defining for how the claimed starting compound is converted to the claimed aminomethyl product.
Applicant may overcome this rejection by amending claim 73 to incorporate the reaction steps and reactants in claims 74 and 75. The amendment should also correct the wording of claims 75 and 77, so that claim 73 recites formation of the azide intermediate and its reduction to the amine. The dependent claims are rejected as being dependent on a rejected claim.
Art of Interest
Christophe et al. (US 5714497) is art of particular interest.
Christophe et al. teaches in Example 67(a) the conversion of cis-cyclohexane-1,4-dimethanol to the corresponding ditosylate using p-toluenesulfonyl chloride and triethylamine. Then substitutes one tosylate with ammonia to isolate cis-4-aminomethylcyclohexyl p-toluenesulfonate. Then further substitutes the remaining tosylate with dimethylamine to obtain the corresponding cis diamine.
However, Christophe et al. does not disclose the presently claimed tert-butyl 2-((4-(hydroxymethyl)cyclohexyl)methoxy)acetate substrate or the claimed mesylate-to-azide-to-amine sequence.
Conclusion
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
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/JENNIFER C SAWYER/Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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