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 .
Priority
The instant application is a 371 National Stage Entry of PCT/NL2023/050109 filed on March 7, 2023 which claims priority to foreign application No. NL2031175 filed on March 7, 2022.
Status of Claims
Acknowledgement is made of cancelled (1-27) and new (28-46) claims filed on May 12, 2025. Claims 28-46 are pending in instant application.
Information Disclosure Statement
The information disclosure statement filed on September 18, 2024 and February 27, 2026 have been considered.
Claim Objections
Claims 28-29 are objected to because of the following informalities:
Claims 28 and 29 recite “metabolic dysfunction-associated steatohepatitis (MASH) a.k.a. non-alcoholic steatohepatitis (NASH)”. For clarity purposes, it is recommended “a.k.a.” is replaced with “also known as”.
Claim 29 also recites “atherosclerotic cardiovascular disease (asCVD) is without inducing” which appears grammatically incorrect and should read “atherosclerotic cardiovascular disease (asCVD).
Appropriate correction is required.
Claim Rejections - 35 USC § 112(d)
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 45 is 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.
Claim 38 recites “wherein the compound is not one of: …
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,… or
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”.
Claim 45, which depends from claim 38, recites “The compound according to claim 38 which is:
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or
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”. This claim directly conflicts with the exclusion proviso of instant claim 38.
For the purposes of applying art, claim 38 is construed as unintentionally listing the conflicting species.
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 § 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.
Claims 28-31, 34-40, 43-46 are rejected under 35 U.S.C. 103 as being unpatentable over Muller et. al. 20221.
The applied reference has a common author/inventor with the instant application. Based upon the earlier published date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(1).
Applicant may rely on the exception under 35 U.S.C. 102(b)(1)(A) to overcome this rejection under 35 U.S.C. 102(a)(1) by a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application, and is therefore not prior art under 35 U.S.C. 102(a)(1). Alternatively, applicant may rely on the exception under 35 U.S.C. 102(b)(1)(B) by providing evidence of a prior public disclosure via an affidavit or declaration under 37 CFR 1.130(b). See MPEP § 2153.01.
Regarding claims 28, 30-31, 34, 36, 38-40, 43 45 a compound of formula (10), Muller 2022 teaches compound SH42, also known as CAS# 2143952-36-5, the same as a species of instant claims 36 and 45 (see Muller 2022 at Table 2 p. 4013).
Muller 2022 Compound SH42
CAS# 2143952-36-5
Instant Claims 36, 45
CAS# 2143952-36-5
Instant Formula (10)
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CAS# 2143952-36-5 reads on instant formula (10) when G is
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, B is
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(compare with instant claims 30, 38-39), R1 is -C(=O)R6 and R6 is C1-6 alkyl specifically methyl, R2 is hydrogen, R3 is
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and n is 1 R6 is hydrogen W is O and Y is hydrogen (compare with instant claims 31, 34, 40, 43), R5 is hydrogen.
Regarding claims 28, 30, 35-36, 38-39, 44, and a compound of formula (10), Muller 2022 teaches also compound 29, also known as CAS# 2143952-38-7 (see Muller 2022 at p. 4014 Compound 29, the same as instant Example 28, see instant spec. at p. 83). CAS# 2143952-38-7 reads on formula (10) when G is
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, B is
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(compare with instant claims 30, 38-39), R1 is hydrogen, R2 is hydrogen, R3 is -[C(R7)2]n-X and R7 is hydrogen and X is -OH, and R5 is hydrogen (compare with instant claims 35, 44).
Muller 2022 Compound 29
Instant Example 28
CAS# 2143952-38-7
Instant Formula (10)
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Regarding claims 28-29 and the treatment or prevention of a DHCR24-mediated disorder, Muller 2022 teaches cholesterol biosynthesis has been linked to different diseases such as Alzheimer’s disease, atherosclerosis, diabetes mellitus, genetic disorders (e.g., Smith-Lemli-Opitz syndrome), multiple sclerosis, nonalcoholic steatohepatitis (NASH), and prostate cancer (see Muller at p. 4005 "1. Introduction"). Muller 2022 teaches CAS# 2143952-38-7 and CAS# 2143952-36-5 are DHCR24 inhibitors, and in particular CAS# 2143952-36-5, SH42, is a lead structure for targeting DHCR24, a cholesterol biosynthesis enzyme that partakes in cholesterol biosynthesis (see id and Muller 2022 at p. 4020 left col. ¶1).
The prior art differs from the instant claims as follows: While Muller 2022 teaches instantly claimed species of formula (10) as drugs targeting DHCR24 for diseases such as NASH, Muller 2022 does not specify i) administering to a patient or ii) species of instant claims 37 and 46.
However,
Regarding claim 37, 46 and a compound species, Muller 2022 teaches CAS# 2143952-36-5 (see Muller 2022 at p. 4013 compound SH42), a structurally similar species to instant CAS# 2982676-24-2, differing only by a repeating -(CH2)- unit.
Muller 2022 Compound SH42
CAS# 2143952-36-5
Instant Claims 37, 46
CAS# 2982676-24-2
Instant Formula (10)
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Muller 2022 also teaches CAS# 2143952-34-3 (see Muller 2022 at p. 4014 Compound 25), a structurally similar species to instant CAS# 2982676-14-0, differing only in Y which is instantly limited to C2 alkenyl vs the prior art C3 alkenyl, a modification of H to methyl.
Muller 2022 Compound 25
CAS# 2143952-34-3
Instant Claims 37, 46
CAS# 2982676-14-0
Instant Formula (10)
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Recall Muller 2022 also teaches CAS# 2143952-38-7 (see Muller 2022 at p. 4014 Compound 29, the same as instant Example 28, see instant spec. at p. 83), which differs isomerically from instantly claimed CAS# 2211031-55-7 or CAS# 2982676-17-3 (see instant spec. at p. 84 Example 30).
Muller 2022 Compound 29
Instant Example 28
CAS# 2143952-38-7
Instant Claims 37, 46
CAS# 2211031-55-7
Instant Claims 37, 46
Example 30
CAS# 2982676-17-3
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Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Regarding i) and administering to a patient, it would have been obvious to an artisan to administer to a patient with NASH a known DHCR24 targeting agent (as taught by Muller 2022) because the prior art teaches DHCR24 targeting agent are useful for treating condition such as NASH (as taught by Muller 2022). The prior art compound would thus be performing it’s art-recognized purpose.
Regarding ii) and differences of -(CH2)- or H vs Me, per MPEP § 2144.08(II)(A)(4)(c), the closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. In addition or in the alternative, per MPEP § 2144.09(I)-(II), “[a] prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities” because “[c]ompounds which are…homologs…are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties” (see, e.g., MPEP § 2144.09(I)-(II)), and the Court has stated that “[i]f a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability.” KSR, 127 S.Ct. at 1740. Here, the prior art teaches highly similar structural compounds differing only by methyl of the instantly claimed invention, wherein such compounds have the same, exact utility as the instantly claimed compounds; accordingly, an artisan would readily appreciate that such compounds could be utilized in the treatment of NASH, exactly as taught and suggested in view of the prior art.
Regarding ii) and differences of isomerism, per MPEP § 2144.09(I)-(II), “[a] prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities” because “[c]ompounds which are…isomers…are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties” (see, e.g., MPEP § 2144.09(I)-(II)), and the Court has stated that “[i]f a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability.” KSR, 127 S.Ct. at 1740. Here, the prior art teaches highly similar structural isomers of the instantly claimed invention, wherein such isomers have the same, exact utility as the species instantly claimed; accordingly, an artisan would readily appreciate that such compounds could be utilized in the treatment of NASH, exactly as taught and suggested in view of the prior art.
Furthermore, it is well-within the ordinary skill in art to i) formulate for use a known compound intended to treat a known condition to treat the known condition, ii) modify a known compound by a change of -(CH2)- or Me for H, and/or iii) make and use an isomer of a known compound.
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Claims 28-31, 34-40, 43-46 are rejected under 35 U.S.C. 103 as being unpatentable over Muller et. al. 20172 as evidenced by Ellulu et. al.3
Regarding claims 28, 30-31, 34, 36, 38-40, 43, 45 a compound of formula (10), Muller 2017 teaches Compound 27, also known as CAS# 2143952-36-5, the same as a species of instant claims 36 and 45 (see Muller 2017 at p. 312 Scheme 4).
Muller 2017 Compound 27
CAS# 2143952-36-5
Instant Claims 36, 45
CAS# 2143952-36-5
Instant Formula (10)
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CAS# 2143952-36-5 reads on instant formula (10) when G is
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(compare with instant claims 30, 38-39), R1 is -C(=O)R6 and R6 is C1-6 alkyl specifically methyl, R2 is hydrogen, R3 is
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and n is 1 R6 is hydrogen W is O and Y is hydrogen (compare with instant claims 31, 34, 40, 43), R5 is hydrogen.
Regarding claims 28, 30, 35-36, 38-39, 44, and a compound of formula (10), Muller 2017 teaches also compound 29, also known as CAS# 2143952-38-7 (see Muller 2017 at p. 312 Scheme 4 Compound 29, the same as instant Example 28, see instant spec. at p. 83).
Muller 2017 Compound 29
Instant Example 28
CAS# 2143952-38-7
Instant Formula (10)
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CAS# 2143952-38-7 reads on formula (10) when G is
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(compare with instant claims 30, 38-39), R1 is hydrogen, R2 is hydrogen, R3 is -[C(R7)2]n-X and R7 is hydrogen and X is -OH, and R5 is hydrogen (compare with instant claims 35, 44).
Regarding claims 28-29 and the treatment or prevention of a DHCR24-mediated disorder, Muller 2017 teaches inhibition of the enzyme DHCR24 can open new therapeutic options for treating Alzheimer's disease, hepatitis C virus infections, and atherosclerosis (see Muller 2017 at p. 315 “Conclusions”). Muller 2017 teaches Compound 27 is a selective DHCR24 inhibitor and Compound 29 biological evaluation is ongoing (see Muller 2017 at p. 314 left col. ¶1).
Further regarding claim 29, Ellulu explains that atherosclerosis is also known as atherosclerotic cardiovascular disease (see Ellulu at Abstract).
The prior art differs from the instant claims as follows: While Muller 2017 teaches instantly claimed species of formula (10) as drugs targeting DHCR24 for diseases such as NASH, Muller 2017 does not specify i) administering to a patient or ii) species of instant claims 37 and 46.
However,
Regarding claim 37, 46 and a compound species, Recall Muller 2017 teaches CAS# 2143952-36-5 (see Muller 2017 at p. 312 Scheme 4), a structurally similar species to instant CAS# 2982676-24-2, differing only by a repeating -(CH2)- unit.
Muller 2017 Compound 27
CAS# 2143952-36-5
Instant Claims 36, 45
CAS# 2143952-36-5
Instant Claims 37, 46
CAS# 2982676-24-2
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Recall Muller 2017 also teaches CAS# 2143952-38-7 (see Muller 2017 at p. 312 Scheme 4 Compound 29, the same as instant Example 28, see instant spec. at p. 83), which differs isomerically from instantly claimed CAS# 2211031-55-7 or CAS# 2982676-17-3 (see instant spec. at p. 84 Example 30).
Muller 2017 Compound 29
Instant Example 28
CAS# 2143952-38-7
Instant Claims 37, 46
CAS# 2211031-55-7
Instant Claims 37, 46
Example 30
CAS# 2982676-17-3
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Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Regarding i) and administering to a patient, it would have been obvious to an artisan to administer to a patient with Alzheimer's disease, hepatitis C virus infections, or atherosclerosis a known DHCR24 targeting agent (as taught by Muller 2017) because the prior art teaches DHCR24 targeting agent are useful for treating condition such as Alzheimer's disease, hepatitis C virus infections, or atherosclerosis (as taught by Muller 2017). The prior art compound would thus be performing its art-recognized purpose.
Regarding ii) and differences of -(CH2)- or H vs Me, per MPEP § 2144.08(II)(A)(4)(c), the closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. In addition or in the alternative, per MPEP § 2144.09(I)-(II), “[a] prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities” because “[c]ompounds which are…homologs…are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties” (see, e.g., MPEP § 2144.09(I)-(II)), and the Court has stated that “[i]f a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability.” KSR, 127 S.Ct. at 1740. Here, the prior art teaches highly similar structural compounds differing only by methyl of the instantly claimed invention, wherein such compounds have the same, exact utility as the instantly claimed compounds; accordingly, an artisan would readily appreciate that such compounds could be utilized in the treatment of NASH, exactly as taught and suggested in view of the prior art.
Regarding ii) and differences of isomerism, per MPEP § 2144.09(I)-(II), “[a] prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities” because “[c]ompounds which are…isomers…are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties” (see, e.g., MPEP § 2144.09(I)-(II)), and the Court has stated that “[i]f a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability.” KSR, 127 S.Ct. at 1740. Here, the prior art teaches highly similar structural isomers of the instantly claimed invention, wherein such isomers have the same, exact utility as the species instantly claimed; accordingly, an artisan would readily appreciate that such compounds could be utilized in the treatment of Alzheimer's disease, hepatitis C virus infections, or atherosclerosis, exactly as taught and suggested in view of the prior art.
Furthermore, it is well-within the ordinary skill in art to i) formulate for use a known compound intended to treat a known condition to treat the known condition, ii) modify a known compound by a change of -(CH2)- or Me for H, and/or iii) make and use an isomer of a known compound.
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Allowable Subject Matter
Claims 32-33, 41-42 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Regarding claims 32, 41, the claims are limited by instant Formula (10) R3 is -CR7=N-n(R6)2, such as instantly disclosed CAS# 2982676-16-2. The closest prior art appears to be Bachmann et. al.4 Bachmann teaches CAS# 124161-78-0 (see Bachmann at p. 1791-1792 "Ozonisierung von Neoergosterylacetat").
CAS# 124161-78-0
Instant Formula (10)
Instant Claim 37
Novel Species
CAS# 2982676-16-2
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CAS# 124161-78-0 differs from the instant claims in that for formula (10) when R3 is -CR7=N-n(R6)2, R6 must be selected from hydrogen or alkyl, which excludes CAS# 124161-78-0’s aldehyde. No reasonable suggestion or motivation was found to modify CAS# 124161-78-0’s aldehyde to an alkyl chain or hydrogen.
Regarding claims 33, 42, the claims are limited by instant Formula (10) R3 is a 5 to 10 membered heteroaryl or heterocycloalkyl, with at least one N. The closest prior art appears to be WO 2014071316 A1 to Lancaster et. al.5 Lancaster teaches screening compounds for treating ovarian cancer (see Lancaster at p. 1) such as CAS# 1449-16-7 (see Lancaster at Table 9 p. 42 “dihydrotomatidine”).
CAS# 1449-16-7
Instant Formula (10)
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CAS# 1449-16-7 differs from the instant claims in that for formula (10), R3 is a N heterocycloalkyl, but the core lacks a double bond which is required for any iteration of G. No reasonable suggestion or motivation was found to modify CAS# 1449-16-7’s core for one of instant formula (10).
Conclusion
Claims 28-29, 32-33, 41-42 are objected to.
Claims 28-31, 34-40, 43-46 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SOPHIA J REILLY whose telephone number is (703)756-5669. The examiner can normally be reached 9:00 am - 5:00 pm EST M-F.
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/S.R./Examiner, Art Unit 1627
/JENNIFER A BERRIOS/ Primary Examiner, Art Unit 1613
1 Cite No. 2 in the IDS filed 9/18/24. Muller et. al. "Dehydrocholesterol Reductase 24 (DHCR24): Medicinal Chemistry, Pharmacology and Novel Therapeutic Options" Current Medicinal Chemistry, 2022, 29, 23, 4005-4025. DOI: 10.2174/0929867328666211115121832. Published January 14, 2022. Hereinafter Muller 2022.
2 Cite No. 3 in the IDS filed 9/18/24. Muller et. al. "New chemotype of selective and potent inhibitors of human delta 24-dehydrocholesterol reductase" European Journal of Medicinal Chemistry, 2017, 140, 305-320. DOI: 10.1016/j.ejmech.2017.08.011. Hereinafter Muller 2017.
3 Ellulu et. al. "Atherosclerotic cardiovascular disease: a review of initiators and protective factors" Inflammopharmacology 2016, 24, 1-10. DOI: 10.1007/s10787-015-0255-y. Hereinafter Ellulu.
4 Bachmann et. al. "Über die Spaltung der Doppelbindung im Neoergosterol" Helvetica, 1959, 42, 6, 1790-1793. DOI: 10.1002/hlca.19590420607. Hereinafter Bachmann.
5 Published May 8, 2014. Hereinafter Lancaster.
Prosecution Insights