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 .
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-3 and 5-10 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Anderskewitz et al. (US 8,877,775).
The reference discloses a process, wherein a compound of formula R8 and a compound of formula R9 are reacted in the presence of n-butyllithium as catalyst, in a tetrahydrofuran solvent, at a temperature of -78°C, to produce a compound of formula I-4.1 (col. 64 and 65). The compound disclosed as I-4.1 is a species of the compound of instant formula (1), wherein R1 and R2 are Br- and F-, and A is a bis-lactim ether. In the process disclosed, the compound R8 is a species of the compound of formula (9-1), wherein R3 and R4 are Br- and F-, and X is Br-. The compound R9 is a species of the compound of formula (9-2), wherein A3 forms an isopropyl group.
The process disclosed by Anderskewitz et al., and the compound made, anticipates the instant claims.
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.
Claim(s) 4, 11, and 12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Anderskewitz et al.
The instant claims further limit the intermediate compound of the present invention to a compound that includes a structure of formula (2), wherein the compound has a boronic ester substituent for the R2 group of formula (1). The compound made in the process described in the rejection above has a Br- or F- substituent on the benzene ring. However, in the synthesis of a different intermediate, I-1.1.3, the reference teaches that a compound having a halogen on the benzene ring may be reacted with bis-pinacolato-diboron, in the presence of a palladium complex, to produce an intermediate wherein one of the halogens on the benzene ring is substituted with a boronic ester group (col. 44 to col. 45).
The instant claims are rendered obvious by the reference teaching, because a person having ordinary skill in the art is taught how to substitute a halogen with a boronic ester group in making the intermediate compounds taught therein.
Claim(s) 13-17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Anderskewitz et al. (8,877,775) as applied to claims 4, 11, and 12 above, and further in view of CN 112979684.
The instant claims are drawn to a method for preparing a drug by performing a fluorination reaction of the intermediate compound of claim 1 to produce a first compound. Further limitations include reacting the intermediate with K18F in the presence of a copper catalyst; and, reacting the first compound with a boronating agent to generate a second compound.
Anderskewitz et al. do not expressly teach a preparing a drug by fluorinating the intermediate compound taught therein; however, the compounds taught by Anderskewitz et al. are intermediates in the production of compounds that have pharmacological use as inhibitors of Cathepsin C that may treat respiratory diseases.
CN 112979684 teaches a process for producing 18F-BPA, a compound used along with boron neutron capture therapy for treating tumor cells, wherein the process comprises reacting an intermediate compound with 18F ions eluted with a potassium compound (resulting in K18F), in the presence of a copper catalyst, and then deprotecting the intermediate formed by removing amino and/or carboxyl groups (e.g., by hydrolysis), to produce 18F-BPA. The compound taught by CN 112979684 has a boronic acid pinacol ester group already present; however, a person having ordinary skill in the art could have used the process taught by Anderskewitz et al. for adding the boronic acid ester group to the compound.
The instant claims are rendered obvious by the combined reference teaches, since a person having ordinary skill in the art would have been able to use the intermediate compounds taught by Anderskewitz et al. in a process for making a drug labeled with 18F by employing the process taught by CN112979684.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SIKARL A WITHERSPOON whose telephone number is (571)272-0649. The examiner can normally be reached M-F 9am-9pm IFP.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SIKARL A WITHERSPOON/Primary Examiner, Art Unit 1692
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