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 .
Continued Examination
A request for continued examination under 37 CFR 1.114, including the fee set forth in
37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible
for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has
been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37
CFR 1.114.
Priority
The instant application is a 371 National Stage Entry of PCT/KR2021/004544 filed on April 12, 2021 which claims priority to foreign application No. KR10-2020-0044730 filed on April 13, 2020. Acknowledgement is made of a certified translation of the Foreign Application KR10-2020-0044730 (filed April 13, 2020) filed on October 23, 2025.
Status of Claims
Acknowledgement is made of amended (1-5), previously presented (6-8), and cancelled (9), claims filed on January 30, 2026. Claims 1-8 are pending in instant application.
Response to Arguments
Applicant's arguments filed January 30, 2026 have been fully considered but they are not persuasive. The Examiner notes the amended claims recite “R’ is…wherein at least one -H,…may be substituted with -X…” The claims as written do not require a substitution on R’, moreover, if required, this change is still obvious in view of the prior art until unexpected results commensurate in scope with the claims are made of record.
Regarding oxadiazole isomeric structures (see 1/30/26 Remarks at pp. 24-25), it is the Examiner’s understanding that Applicant argues an oxadiazole isomer would not be reached based on the prior art’s synthetic strategy would not work to reach the instantly claimed isomeric structure. However, the instant claims are compound claims, and one skilled in the art would readily appreciate there is more than one way to make a desired compound. A novel useful compound that is isomeric with the prior art compound is unpatentable unless it possesses some unobvious or unexpected beneficial property not possessed by the prior art compound. In re Norris, 179 F.2d. 970, 84 USPQ 458 (CCPA 1970). Therefore, it would have been obvious to one of ordinary skill to expect similar properties of structurally similar compounds since they are suggestive of one another. It has been held that a compound, which is structurally isomeric with a compound of the prior art, is prima facie obvious absent unexpected results. In re Finely, 81 USPQ 383 (CCPA 1949); 84 USPQ 458 (CCPA 1950).
Regarding advantageous properties and the Declaration (see 1/30/26 Remarks at pp. 27-28 and Declaration Pursuant to 37 C.F.R. §1.132),
It is the Examiner’s understanding that Applicant alleges the existence of unexpected results commensurate in scope with the requirements of MPEP §716, §716.01, and §716.02, wherein such results are sufficient to rebut prima facie. However, to establish unexpected results, the evidence must establish that the expected results occur to an unexpected extent (see, e.g., MPEP § 716.02(a)(I)), on the basis of statistically and practically significant evidence (see, e.g., MPEP § 716.02(b)(I)), which is fully explained (see, e.g., MPEP § 716.02(b)(II)), commensurate in scope with the claimed invention (see, e.g., MPEP § 716.02(d)), and wherein a comparison of the claimed invention with the closest prior art of record is provided (see, e.g., MPEP § 716.02(e)). Furthermore, even if evidence satisfying MPEP §§ 716.02, 716.02(a), 716.02(b), 716.02(d), and 716.02(e) is set forth on record, such evidence may not be sufficient to rebut prima facie obviousness because the evidence of expected and unexpected results must be weighed (see, e.g., MPEP § 716.02(c)(I)) and the totality of the record considered (see, e.g., MPEP § 716.02(f)), including teachings in the prior art and evidence of expected results which weigh in favor of a determination of obviousness (see, e.g., MPEP § 716.02(c)(II)).
Regarding the Walji Rejection, if Applicant means to allege the existence of unexpected results commensurate in scope with the requirements of MPEP § 716.02 based upon instant Examples 39 and 12 (see 1/30/26 Remarks at p. 25) this is also not persuasive because the requirements of MPEP § 716.02 have not been satisfied. Specifically, 716.02(e) is not satisfied because it is unclear if the oxadiazole change (1,2,4 vs 1,3,6) from Walji’s Compound 406 is what is enhancing selectivity in the comparison, or if it is an H for F change, or both. The proper comparisons would be:
Walji Compound 406
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H/F Change
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A proper comparison to the closest prior art would help to clearly explain why the instant invention is unexpected in light of obvious alterations to Walji’s Compound 406 (see also MPEP § 716.02(b)(II)).
Regarding the Lee/Wermuth Rejection, if Applicant means to allege the existence of unexpected results commensurate in scope with the requirements of MPEP § 716.02 based upon instant Examples 9, 10, 31, 34, and 16 (see 1/30/26 Remarks at p. 28 ¶2-4) this is also not persuasive because the requirements of MPEP § 716.02 have not been satisfied. Specifically, 716.02(b)(II) is not satisfied because the comparison to the compound SP1418 (see Lee Example 82) to instant SP2969 is not discussed (see 1/30/26 Remarks at p. 28 ¶4). The omitted comparison is important for satisfying MPEP § 716.02(d) as well, in order to show advantageous properties across a diverse range of species commensurate in scope with the instant claims. The Examiner notes in the Declaration it appears the western blot results for SP1418 are abnormal; (i) a missing bar graph for tubulin acetylation degree (instead a repeated gel image is pictured) and (ii) a missing control band compared to the other gels (see 10/23/25 Declaration at p. 3). Additionally, “N.T” is not defined (see id), but is assumed to mean “not tested” which would indicate the compound SP1418 was not tested and thus cannot be compared to the instant compound SP2969, and the X and Y axis labels of the control compound bar graphs are missing (see id). Accordingly, the proffered data at Examples 9, 10, 31, 34, and 16 is insufficient to establish unexpected results commensurate in scope with the requirements of MPEP § 716.02 because instant SP2969 is representative of species wherein R is piperidinyl, which encompasses a portion of the defined species claimed.
The omitted experimental data and discussion between instant SP2969 and SP1418 does not allow for a proper side-by-side comparison to establish unexpected results commensurate in scope with the claims. SP1418 is notably similar to the prior art compound Lee Example 82, varying only in H for F. Experimental data comparing SP2969 and SP1418 and especially presently untested instant compound 2951 (see claim 5) to Lee Example 82 would be the closest comparisons to the prior art (see also MPEP § 716.02(e)).
Claim Interpretation
Claim 7 is drawn to a composition product with intended use. The limitations of claim 7 are met by the structural limitations; a pharmaceutical composition comprising a compound of Formula I.
Modified Rejection(s)
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.
Claims 1-4, 6-8 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2017/222951 A11 to Walji in view of Boström et. al.2, Wermuth3, and Shen et. al.4
Regarding compounds of Formula I, Walji teaches HDAC6 inhibitors Compounds 57 (CAS# 2170452-22-7, see Walji at p.102), 61 (CAS# 2170452-26-1, see Walji at p. 102), 90 (CAS# 2170452-55-6, see Walji at p. 111), 198 (CAS# 2170453-59-3, see Walji at p. 171), 403 (CAS# 2170455-58-8, see Walji at p. 210), and 406 (CAS# 170455-61-3, see Walji at p. 211) which correspond with instant Formula I.
Walji Compound 406
Instant
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For example, Walji compound 406 corresponds to instant Formula I when R1 is CX3, specifically CF3, L1 is C0 alkylene, Z1, Z3-4 are CH, Z2 is N, L is C1 alkylene, L2 is C0 alkylene, R2 is aryl substituted with X, specifically phenyl substituted with F, R is
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, wherein n and m are 2, R’ is C3-C7 cycloalkyl specifically cyclopropyl.
Regarding claims 6-7 and a pharmaceutical composition, Walji claims a pharmaceutical composition (see Walji at claim 24).
Regarding claims 8-9 and a method of treating, Walji claims use of the HDAC6 inhibitors for treating diseases such as neurodegenerative diseases and cellular proliferation diseases (see Walji at claim 27).
The prior art differs from the instant claims as follows: While Walji teaches structurally similar compounds for inhibiting HDAC6, the compounds differ in (i) 1,2,4-oxadiazole (Walji) vs 1,3,4-oxadiazoles (instant) and (ii) H (Walji) for F (instant) on the nitrogen heterocycle R’s.
However,
Regarding oxadiazoles, Boström teaches 1,3,4-oxadiazole has lower lipophilicity and higher solubility compared to 1,2,4-oxadiazole (see Bostrom at p. 1827 right col. ¶2). Wermuth teaches 1,3,4-oxadiazole and 1,2,4-oxadiazole are bioisosteres (see Wermuth at p. 213 Figure 13.8). Shen teaches HDAC6 inhibitors contain zinc binding groups, or ZBG (see Shen at p. 122 right col. and at Figure 1). Shen teaches oxadiazole-type ZBGs have been applied to HDAC6 inhibitors (see Shen at p. 122 "Article highlights"). Shen teaches both 1,3,4 oxadiazole and 1,2,4 oxadiazole ZBGs have been employed with successful HDAC6 inhibitory activity (see Shen at Figure 5).
Regarding H for F, Wermuth also teaches H for F bioisosterism improves metabolic degradation (see Wermuth at pp. 226-227 “A. Fluorine-hydrogen isosterism”).
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):
Per MPEP § 2143(I)(D), a prima facie case of obviousness exists for applying a known technique to a known method or product ready for improvement to yield predictable results. It would have been obvious to substitute 1,3,4-oxadiazole for 1,2,4-oxadiazole and H for F to on Walji’s compounds to arrive at an anticipatory compound of Formula I because the prior art teaches these changes improve compound properties desirable for administrating to a subject for treatment (oxadiazole swap improves lipophilicity, H for F improves stability) (as taught by Bostrom and Wermuth). In addition, the prior art teaches 1,3,4-oxadiazole and 1,2,4-oxadiazole are both suitable moieties for the ZBG portion of an HDAC6 inhibitor (as taught by Shen).
Furthermore, it is well-within the ordinary skill in art to incorporate F in lieu of H or one oxadiazole isomer for another.
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Maintained Rejection(s)
Claims 1-7 are rejected under 35 U.S.C. 103 as being obvious over US 2018/0215743 A15 to Lee in view of Wermuth6.
The claims are drawn to structurally similar compounds for the same use.
Regarding instant claims 1-5 and Lee claims 1-6 and compound structures, The compound cores correspond with Overlapping Formula I below wherein R1 is Lee R1 and instant R1 and may be CX3, X is halogen and n is 1 or 2, and R is Lee R2, specifically
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and Y is N, and instant R.
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Lee R
Instant R
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Lee Claims 6, 7 Example 82
Instant Claim 5 Example 14
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Regarding instant claims 6-7 and a composition, Lee teaches a pharmaceutical composition comprising a claimed compound (see Lee claim 8) for inhibiting HDAC6 (see Lee at Title).
The prior art differs from the instant claims as follows: The R2 structural limitations on Lee do not require an F as in instant R. For example, compare the species Lee Example 82 (Lee claims 6-7) with instant Example 14 which only differ in H for F and a change of -CH2-.
However,
Regarding H for F, Wermuth teaches F mimics H and H for F bioisosterism improves metabolic degradation (see Wermuth at pp. 226-227 “A. Fluorine-hydrogen isosterism”).
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 patented claims for at least the following reason(s):
Regarding a change of -CH2-, 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 compounds of generally sufficiently close structure have a presumed expectation that such compounds possess similar properties, including variation by -CH2- (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. In addition, 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. Here, the prior art teaches highly similar structural compounds of the instantly claimed invention, wherein such compounds have the same, exact utility as the instantly claimed HDAC6 inhibitors; accordingly, an artisan would readily appreciate that such compounds could be utilized in the inhibition of HDAC6, exactly as taught and suggested in view of the prior art.
Regarding H for F, 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. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). In addition, the prior art teaches F often mimics H (see Wermuth at p. 226). Given the same utility of Lee and instant compounds, H for F would be obvious to one skilled in the art. See also § 2144.08(II)(A)(4)(d), “It is the properties and utilities that provide real world motivation for a person of ordinary skill to make species structurally similar to those in the prior art. Dillon, 919 F.2d at 697, 16 USPQ2d at 1905; In re Stemniski, 444 F.2d 581, 586, 170 USPQ 343, 348 (CCPA 1971).”
Further regarding H for F, per MPEP § 2143(I)(D), a prima facie case of obviousness exists for applying a known technique to a known method or product ready for improvement to yield predictable results. The prior art teaches an H for F change improves compound properties desirable for administrating to a subject for treatment (better stability). One would be motivated to make such a change if inhibiting HDAC6 in a subject.
Furthermore, it is well-within the ordinary skill in art to incorporate F in lieu of H, and a ring differing by -CH2- changes.
Therefore, an artisan would arrive at the same invention as presently claimed.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-7 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 10,584,117 B27 to Lee in view of Wermuth8.
The applicable analysis for Nonstatutory Double Patenting is set forth in MPEP § 804(II), and specifically MPEP § 804(II)(B). MPEP § 804(II)(B)(2)-(3) identifies that a Nonstatutory Double Patenting Rejection may be appropriate based upon either an anticipation analysis or an obviousness analysis. The instant analysis is an obviousness analysis.
The claims are drawn to structurally similar compounds for the same use.
Regarding instant claims 6-7 and compositions for an intended use, per MPEP §804(II)(B)(1), the court explained that it is also proper to look at the disclosed utility in the reference disclosure to determine the overall question of obviousness in a nonstatutory double patenting context. See Sun Pharm. Indus., Ltd. v. Eli Lilly & Co., 611 F.3d 1381, 95 USPQ2d 1797 (Fed. Cir. 2010). In particular, when ascertaining the scope of the reference’s claim(s) to a compound, the examiner should consider the reference’s specification, including all of the compound’s uses that are disclosed. See Sun Pharm. Indus., 611 F.3d at 1386-88, 95 USPQ2d at 1801-02. Lee discloses the utility of inhibiting HDAC6 (see Lee at Title).
Regarding instant claims 1-5 and Lee claims 1-6 and compound structures, The compound cores correspond with Overlapping Formula I below wherein R1 is Lee R1 and instant R1 and may be CX3, X is halogen and n is 1 or 2, and R is Lee R2, specifically
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and Y is N, and instant R.
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Lee Claims 6, 7 Example 82
Instant Claim 5 Example 14
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Regarding instant claims 6-7 and a composition, Lee teaches a pharmaceutical composition comprising a claimed compound (see Lee claim 8).
The patented claims differ from the pending claims as follows: The R2 structural limitations on Lee do not require an F as in instant R. For example, compare the species Lee Example 82 (Lee claims 6-7) with instant Example 14 which only differ in H for F and changes of -CH2-.
However,
Regarding H for F, Wermuth teaches F mimics H and H for F bioisosterism improves metabolic degradation (see Wermuth at pp. 226-227 “A. Fluorine-hydrogen isosterism”).
Therefore, it would have been obvious to one of ordinary skill in the art to arrive at the instantly claimed invention with a reasonable expectation of success in view of the patented claims for at least the following reason(s):
Regarding changes in -CH2-, 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 compounds of generally sufficiently close structure have a presumed expectation that such compounds possess similar properties, including variation by -CH2- (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. In addition, 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. Here, the prior art teaches highly similar structural compounds of the instantly claimed invention, wherein such compounds have the same, exact utility as the instantly claimed HDAC6 inhibitors; accordingly, an artisan would readily appreciate that such compounds could be utilized in the inhibition of HDAC6, exactly as taught and suggested in view of the prior art.
Regarding H for F, 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. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein). In addition, the prior art teaches F often mimics H (see Wermuth at p. 226). Given the same utility of Lee and instant compounds, H for Me and H for F would be obvious to one skilled in the art. See also § 2144.08(II)(A)(4)(d), “It is the properties and utilities that provide real world motivation for a person of ordinary skill to make species structurally similar to those in the prior art. Dillon, 919 F.2d at 697, 16 USPQ2d at 1905; In re Stemniski, 444 F.2d 581, 586, 170 USPQ 343, 348 (CCPA 1971).”
Further regarding H for F, per MPEP § 2143(I)(D), a prima facie case of obviousness exists for applying a known technique to a known method or product ready for improvement to yield predictable results. The prior art teaches an H for F change improves compound properties desirable for administrating to a subject for treatment (better stability). One would be motivated to make such a change if inhibiting HDAC6 in a subject.
Furthermore, it is well-within the ordinary skill in art to incorporate F in lieu of H and a ring differing by -CH2- changes.
Therefore, an artisan would arrive at the same invention as presently claimed.
Conclusion
Claims 1-8 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 Filed June 19, 2017 and published December 28, 2017. Hereinafter Walji. Referenced in previous Office Action.
2 Boström et al. "Oxadiazoles in Medicinal Chemistry" J. Med. Chem. 2012, 55, 5, 1817–1830. DOI: 10.1021/jm2013248. Hereinafter Boström. Referenced in previous Office Action.
3 Wermuth, C. G. The Practice of Medicinal Chemistry "Chapter 13: Molecular Variations Based on Isosteric Replacements" Academic Press Limited, 1996, pp. 1-35. ISBN 0-12-744640-0. Hereinafter Wermuth. Referenced in previous Office Action.
4 Shen et. al. "A patent review of histone deacetylase 6 inhibitors in neurodegenerative diseases (2014-2019)" Expert Opinion on Therapeutic Patents 2020, 30, 121-136. DOI: 10.1080/13543776.2019.1708901
5 Published August 2, 2018. Later patented March 10, 2020as US 10,584,117 B2. Corresponding to PCT/KR2016/008216, WO 2017/018804, and US 2018/0215743 A1. Hereinafter Lee. Referenced in previous Office Action.
6 Wermuth, C. G. The Practice of Medicinal Chemistry "Chapter 13: Molecular Variations Based on Isosteric Replacements" Academic Press Limited, 1996, pp. 1-35. ISBN 0-12-744640-0. Hereinafter Wermuth. Referenced in previous Office Action.
7 Patented March 10, 2020 to overlapping Assignee and Inventors. Corresponding to PCT/KR2016/008216, WO 2017/018804, and US 2018/0215743 A1. Hereinafter Lee. Referenced in previous Office Action.
8 Wermuth, C. G. The Practice of Medicinal Chemistry "Chapter 13: Molecular Variations Based on Isosteric Replacements" Academic Press Limited, 1996, pp. 1-35. ISBN 0-12-744640-0. Hereinafter Wermuth. Referenced in previous Office Action.