DETAILED ACTION
Notice of 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 .
Election/Restrictions
Applicant’s election without traverse of Group I in the reply filed on 3/17/2025 is acknowledged. The requirement is still deemed proper and is therefore made FINAL.
Claims 19, 21-22, 25 and 28-32 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Applicant’s election without traverse of a single species of Formula (I), which is Compound 68 having the following structure:
PNG
media_image1.png
106
308
media_image1.png
Greyscale
, is also acknowledged.
The elected species reads upon claims 1-6, 13-16 and 18, which are rejected below under 35 U.S.C. 103(a) as being unpatentable over Kirpotina et al (Molecular Pharmacology 77:159-170, 2010) in view of Williams et al (Foye’s Principles of Medicinal Chemistry, 5th Edition, Pages 59-63, 2002).
However, in the course of examining Applicant’s elected species, at least two additional prior art compounds of Formula (I) were identified. Those compounds are:
Applicant’s instantly claimed Compound 54 having the following structure:
PNG
media_image2.png
106
328
media_image2.png
Greyscale
, which entails a compound of Formula (I) wherein X1 is C; R1, R2, R4 and R5 are each H; R3 is halo (i.e., chloro); L1 is alkylene; and R6 is substituted aryl (i.e., phenyl substituted with methoxy), and which reads on claims 1-6, 13-16 and 18. Those claims are additionally rejected below under 35 U.S.C. 102(a)(1) as being anticipated by Kirpotina et al (Molecular Pharmacology 77:159-170, 2010); and
PNG
media_image3.png
118
306
media_image3.png
Greyscale
, which entails a compound of Formula (I) wherein X1 is C; R1, R2, R4 and R5 are each H; R3 is halo (i.e., bromo); L1 is alkylene; and R6 is substituted aryl (i.e., phenyl substituted with chloro), and which reads on claims 1-6, 13-15 and 18. Those claims are additionally rejected below under 35 U.S.C. 102(a)(1) as being anticipated by Kirpotina et al (Molecular Pharmacology 77:159-170, 2010).
Claim Rejections - 35 USC § 102
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.
Claims 1-6, 13-16 and 18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kirpotina et al (Molecular Pharmacology 77:159-170, 2010).
Claim 1 is drawn to a compound of Formula (I) which embraces the following compound species:
PNG
media_image2.png
106
328
media_image2.png
Greyscale
(hereinafter Compound 54) wherein X1 is C; R1, R2, R4 and R5 are each H; R3 is halo (i.e., chloro); L1 is alkylene; and R6 is substituted aryl (i.e., phenyl substituted with methoxy), which reads on claims 1-6 and 13-16.
The instantly claimed compound is taught by Kirpotina et al (Page 162, Figure 1, Compound AG-26).
Accordingly, claims 1-6 and 13-16 are anticipated.
Claim 18 is drawn to a pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.
As taught by Kirpotina et al, “[t]he compounds were diluted in DMSO at a concentration of 2 mg/ml and stored” (Page 160, Column 2, Materials).
Since DMSO entails a pharmaceutically acceptable carrier, claim 18 is also anticipated.
Claims 1-6, 13-15 and 18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kirpotina et al (Molecular Pharmacology 77:159-170, 2010).
Claim 1 is drawn to a compound of Formula (I) which embraces the following compound species:
PNG
media_image3.png
118
306
media_image3.png
Greyscale
wherein X1 is C; R1, R2, R4 and R5 are each H; R3 is halo (i.e., bromo); L1 is alkylene; and R6 is substituted aryl (i.e., phenyl substituted with chloro), which reads on claims 1-6 and 13-15.
The instantly claimed compound is taught by Kirpotina et al (Page 165, Table 3, Compound AG-9/49).
Accordingly, claims 1-6 and 13-15 are anticipated.
Claim 18 is drawn to a pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.
As taught by Kirpotina et al, “[t]he compounds were diluted in DMSO at a concentration of 2 mg/ml and stored” (Page 160, Column 2, Materials).
Since DMSO entails a pharmaceutically acceptable carrier, claim 18 is also anticipated.
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.
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 1-6, 13-16 and 18 are rejected under 35 U.S.C. 103(a) as being unpatentable over Kirpotina et al (Molecular Pharmacology 77:159-170, 2010) in view of Williams et al (Foye’s Principles of Medicinal Chemistry, 5th Edition, Pages 59-63, 2002).
Claim 1 is drawn to a compound of Formula (I) which embraces Applicant’s elected compound species:
PNG
media_image1.png
106
308
media_image1.png
Greyscale
wherein X1 is C; R1, R2, R4 and R5 are each H; R3 is halo (i.e., chloro); L1 is alkylene; and R6 is substituted aryl (i.e., phenyl substituted with chloro), which reads on claims 1-6 and 13-16.
As discussed above, Kirpotina et al teach the following compound species
PNG
media_image3.png
118
306
media_image3.png
Greyscale
(Page 165, Table 3, Compound AG-9/49), which differs from Applicant’s elected compound species in comprising a bromine atom at the position identified in Formula (I) as R3 as opposed to a chlorine atom.
Yet, as taught by Williams et al “[w]hen a lead compound is first discovered for a particular disease state, it often lacks the required potency and pharmacokinetic properties suitable for making it a viable clinical candidate… The medicinal chemist therefore must modify the compound to reduce or eliminate these undesirable features without losing the desired biological activity. Replacement or modification of functional groups with other groups having similar properties is known as isosteric or bioisosteric replacement” (Page 59). Although it is clear that “the use of bioisosteric replacement (classical or nonclassical) in drug development is highly dependent upon the biological system being investigated” and that “[n]o hard and fast rules exist to determine what bioisosteric replacement is going to work with a given molecule” it is also clear that “some generalizations have been possible” (Page 60). Notably, one such generalization is that -Cl and –Br (which are classic monovalent bi isosteres) can replace each other (Page 61, Table 2.9).
Accordingly, it would have been prima facie obvious to a person of ordinary skill in the art at the time the invention was made to replace the bromine atom in Compound AG-9/49 taught by Kirpotina et al with a chlorine atom. The person of ordinary skill in the art at the time the invention was made would have been motivated to make the bioisosteric modifications to synthesize similar compounds that retain biological activity, but have improved physiochemical properties and better pharmacokinetic behavior.
As such, claims 1-6 and 13-16 are rejected as prima facie obvious.
Claim 18 is drawn to a pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable carrier.
As taught by Kirpotina et al, “[t]he compounds were diluted in DMSO at a concentration of 2 mg/ml and stored” (Page 160, Column 2, Materials).
It would have been obvious to similarly dilute the prima facie obvious compound in DMSO and, since DMSO entails a pharmaceutically acceptable carrier, claim 18 is also rejected as prima facie obvious.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CRAIG D RICCI whose telephone number is (571) 270-5864. The examiner can normally be reached on Monday through Thursday, and every other Friday, 7:30 am - 5:00 pm ET. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Bethany Barham can be reached on (571) 272-6175. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/CRAIG D RICCI/Primary Examiner, Art Unit 1611
Prosecution Insights