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 .
Status of the Application
Claims 1-9 and 14-21 are pending as of the response filed 03/26/2026. Claims 10-13 are cancelled. Applicant’s election of a group I claims and a species of disease or condition as depressive disorders is maintained. Claims 15-21 remain withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Claims 1-9 and 14 are examined herein.
The objection to the specification of previous record is withdrawn in consideration of amendments to the specification to remove the “https://”.
The 35 U.S.C. 112(b) rejection of previous record is withdrawn in consideration of the claim amendments.
The claim amendments do not fully overcome the 35 U.S.C. 102 rejection of record over Myerson. Applicant’s arguments regarding the 35 U.S.C. 102 rejection of record, specifically in regards to the rejection of claims 2, 4 and 8, was carefully considered and was found to be persuasive. Applicant’s argument that a generic chemical formula could not anticipate a species without more if the generic formula encompasses a vast number of alternatives, especially with respect to the compounds of instant formula (I) and instant formula (III) was found to be persuasive. The statutory class of the rejection of claims 2, 4 and 8 has been changed to a 103 versus a 102. Since this constitutes a new ground of rejection, this Office action is non-final.
In view of the pending claims, the following rejections are made.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 5-6 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Regarding claim 5, the claim depends from claim 1 and recites “wherein R1 is a C1-C4 alkyl”. However, claim 1, as amended does not allow for R1 to be a C1 alkyl for a compound of formula (II). This broadens the scope of the dependent claim 5, which is improper.
Regarding claim 6, the claim depends from claim 5, which depends from claim 1 and recites “wherein R1 is a methyl”. However, claim 1, as amended does not allow for R1 to be a C1 alkyl (methyl) for a compound of formula (II). This broadens the scope of the dependent claim 6, which is improper.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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 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.
Claims 1, 3, 5, 9 and 14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Myerson et al. (WO 2018/104729 A1, 14 June 2018, hereinafter Myerson, of previous record).
Regarding instant claims 1, 3 and 5, Myerson teaches conformationally stabilized analogues of the ketamine metabolites 6-hydroxyketamine and 6-hydroxynorketamine with applications in the treatment of depression disorders and anxiety disorders (Abstract). Myerson teaches compounds of Formula I, or a pharmaceutically acceptable salt thereof; wherein R1 is H or C1-C4 alkyl; R2 is H or C1-C4 alkyl; R3 is H or C1-C4 alkyl; R4 is H or C1-C4 alkyl; R5 is H or C1-C4 alkyl; and R6 represents 0, 1, 2, 3, 4 or 5 haloatoms each independently selected from F, CI, Br, I, wherein when R2 is H, preferably at least one of R3, R4and R5 is not H (Abstract; Pg. 1, Lns. 4-13).
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Myerson teaches the exemplary compound, compound 16 (Pg. 12, Lns. 1-4).
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Compound 16 of Myerson falls within the scope of instant formula (II), specifically formula (IIa) (as in instant claims 3), wherein R1 is a propyl (namely, isopropyl).
Regarding instant claims 9 and 14, Myerson teaches compositions are prepared by uniformly and intimately admixing the active ingredient with liquid carriers or finely divided solid carriers or both and may be prepared by mixing the principle active agent(s) with a pharmaceutical carrier (Pg. 3, Lns. 3-9). Myerson teaches oral dosage forms for oral administration (Pg. 2, Ln. 37 – Pg. 3, Ln. 13; Pg. 13, Lns. 19-24).
Therefore, Myerson anticipates the pharmaceutical composition as in instant claims 9 and 14.
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 1-2, 9 and 14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wainer (WO 2017/087388 A1, 26 May 2017).
Regarding instant claims 1-2, Wainer teaches phenyl cyclohexanone derivatives, pharmaceutical compositions and methods of use thereof (Title; Abstract). Wainer teaches compounds of Formula I or a pharmaceutically acceptable salt thereof, with variables as defined (Pg. 1, fifth paragraph - Pg. 2, continued paragraph). Wainer teaches an exemplary compound of Formula V (Pg. 13).
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The compound of Formula V of Wainer falls within the scope of instant formula (I), wherein R1 is hydroxyl. Wainer teaches the compounds may be of use in the treatment of depression (Pg. 2, last paragraph; Pg. 19, continued paragraph). Wainer teaches the compounds may exist as stereoisomers, diastereomers, enantiomers (Pg. 3, third paragraph - Pg. 4, third full paragraph). Wainer anticipates the limitations of instant claims 1-2
Regarding instant claims 9 and 14, Wainer teaches pharmaceutical composition including a compound of Formula I or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable excipient (Pg. 2, first full paragraph; Pg. 23 first full paragraph). Wainer teaches the pharmaceutical composition comprise a carrier (Pg. 9, second - third full paragraph). Wainer teaches the compositions are formulated for oral administration (Pg. 23, first full paragraph - last paragraph).
Therefore, Wainer anticipates the pharmaceutical composition as in instant claims 9 and 14.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
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 2-8 are rejected under 35 U.S.C. 103 as being unpatentable over Myerson et al. (WO 2018/104729 A1, 14 June 2018, hereinafter Myerson, of previous record).
Please note that this obviousness rejection for claim 3 is made for the additional homologs of formula (II) not anticipated by the Myerson.
The teachings of Myerson are set forth in the anticipation rejection above and incorporated herein by reference.
Regarding instant claims 2 and 4-8, wherein the instant R1 group is ortho or para to the hydroxyl group of the cyclohexane ring, Myerson teaches embodiments in which R3 is H or Me; R4 is H or Me and when R2 is H and at least one of R3, R4, and R5 is not H (Pg. 8, Lns. 13-17). Myerson teaches exemplary compounds, compound 1 (Pg. 11, Lns. 34-35) and compound 11 (Pg. 12, Lns. 1-4).
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Compound 1 of Myerson has an R1 (methyl) in both the ortho and para positions to the hydroxyl group of the cyclohexane ring. Compound 11 of Myerson has an R1 (methyl) in the meta position to the hydroxyl group of the cyclohexane ring that is a positional isomer of the instant compounds of formula (I) and formula (III).
Considering that compound 11 of Myerson teaches R1 being methyl, present in a position meta to the hydroxyl group of the cyclohexane ring AND that Myerson teaches R1 being methyl can be present in a position ortho or para to the hydroxyl group of the cyclohexane ring, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, in view of the teachings of Myerson to have synthesized a compound with an R1 group ortho or para to the hydroxyl group of the cyclohexane ring, to arrive at the compounds of instant formula (I) or instant formula (III), with a reasonable expectation of success.
According to MPEP 2144.09 (II), “Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
Further according to MPEP 2144.09 (I), “A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).”
In the instant case, the compounds of the instant invention are taught to be useful in the treatment of depressive disorder, anxiety disorders, among other conditions (Paras. [0012]-[0013] of the instant specification). The hydroxyketamine compounds of Myerson are taught to find applications in the treatment of depression disorders and anxiety disorders. The compounds of Myerson anticipate the instant compounds of formula (II) and are positional isomers of instant compounds of formula (I) and formula (III). Here, the cited compounds of Myerson are so close in structure that, correspondingly, the instant compounds of formula (I) and formula (III) would be expected to have very similar or identical utilities and functional properties, rendering them prima facie obvious.
Therefore, one of ordinary skill in the art would have been motivated to synthesize the positional isomers, to arrive at the compounds as in formula (I) and formula (III) of the instant invention with a reasonable expectation of success.
Furthermore, according to MPEP 2144.09 (III), Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious. In re Payne, 606 F.2d 303, 203 USPQ 245 (CCPA 1979). Absent any criticality, the simple addition of -CH2- groups would be prima facie obvious.
Therefore, it would have been prima facie obvious to one of ordinary skill in the art to modify the number of -CH2- groups in the R3, R4 and R5 groups of Myerson (that teaches R3, R4 and R5 can be H or C1-4 alkyl) to obtain the instantly claimed species of compounds, with a reasonable expectation of success. The motivation being to provide additional conformationally stabilized analogues of the ketamine metabolites 6-hydroxyketamine and 6-hydroxynorketamine for further pharmacological and/or commercial development.
Therefore the teachings of Myerson render obvious the limitations of instant claims 2 and 4-8 of formula (I) and formula (III) and the additional homologs of formula (I) of instant claims 3, 5 and 7.
Conclusion
Claims 1-9 and 14 are rejected.
No claims are allowed.
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/PADMAJA S RAO/Examiner, Art Unit 1627
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