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 Claims
Claims 1-4, 6, 8-10, 12, 14, 31, and 33 are pending in this application. Claims 5, 7, 11, 13, 15-30, 32, and 34-37 have been cancelled by applicant. Claims 1-4, 6, 8-10, 12, and 14 are under examination herein. Claims 31 and 33 are withdrawn from consideration.
Notes:
Claim 10 has been rejoined, as amendments make the claim read on elected species.
Claim Objections
Claims 1-3 are objected to because of the following informalities: Claims have different definitions for variable Ra within the same claim, with some instances of Ra being defined as aliphatic, aromatic, etc.; and other instances being H, aliphatic, etc. Either maintain a single, consistent definition for Ra, or employ different variables.
Appropriate correction is required.
Claim Interpretation
Amended claims 1 and 2 read: “R11 is selected from hydrogen, a group selected from an R2 group…” – thus, the claims, as presented require R11, however, Formula II does not have an R11 variable. Therefore, for the purposes of applying art, in light of the fact that Applicant has elected the species of Formula II for examination, which does not have a variable R11, (see the restriction/election requirement of 06/11/2025 and non-final filed 12/18/2025), it will be assumed that R11 may or may not be present, depending on weather instant Formula II or III is being considered.
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, 8-10, 12 are rejected under 35 U.S.C. 103 as being unpatentable over Chaoyang et al. (CN 1371912 A – previously cited) (“Chaoyang”).
Regarding claims 1-4, 6, 8-10, 12, Chaoyang discloses the androsterol alkyl carbonate compounds below (page 1 of original doc., and page 1 of translated doc.), useful for oral assimilation of nutrients and proteins (page 2, para. 1 of translated doc.), which reads on metabolic diseases, which is one of the intended conditions to be treated by the instant compounds. Chaoyang’s disclosure renders the instantly claimed compounds obvious when: R’ is -OC(O)OCH3, or -OC(O)O-nC3H7, or -OC(O)O-nC4H9, or -OC(O)O-Ph, or -OC(O)O-cyclohexyl (corresponding to instant R2 being -C(O)ORa, and Ra being aliphatic, aromatic, or an organic functional group); and R can be a carbonyl (=O). Thus, Chaoyang discloses a narrow genus of compounds which is encompassed by the instantly elected genus when instant Y is aliphatic; X is H; R3-9 are H; and R11 is absent.
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While Chaoyang does not specifically teach their group corresponding to instant R1 being -Me (reading on alkyl/ lower alkyl/ organic functional group); Applicant is advised that H vs. Me is considered an obvious modification in the absence of superior, unexpected results. Note In re Wood 199 USPQ 137; In re Lohr 187 USPQ 548 and In re Bowers 149 USPQ 573. Note also In re Fauque 121 USPQ 425 in which differences were 2H’s vs 2 methyl groups. Also see MPEP 2144.09.
Therefore, regarding instant claims 1-4, 6, 8-10, 12, replacing the H corresponding to instant position R1 in Chaoyang’s compounds with a methyl group is an obvious modification in the absence of superior unexpected results. Thus, one having ordinary skill in the art would have found the claimed compounds prima facie obvious, since they are generically embraced by Chaoyang’s disclosed formula. The requisite motivation for arriving at the claimed compounds stems from the fact that they fall within the generic class of compounds disclosed by Chaoyang as useful for the treatment of oral assimilation of nutrient issues (reading on metabolic disease). Accordingly, one having ordinary skill in the art would have been motivated to prepare any of the compounds embraced by the disclosed generic formula, including those encompassed by the claims.
Furthermore, 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).
Further regarding claim 8, with respect to the stereoisomerism of Formulae IIA and IIB, in view of Chaoyang’s racemic compounds disclosed above, it is noted that in Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293 (Fed. Cir. 2007), the court relied on the settled principle that in chemical cases, structural similarity can provide the necessary reason to modify prior art teachings. The Federal Circuit also addressed the kind of teaching that would be sufficient in the absence of an explicitly stated prior art-based motivation, explaining that an expectation of similar properties in light of the prior art can be sufficient, even without an explicit teaching that the compound will have a particular utility. The Federal Circuit cautioned that requiring such a clearly stated motivation in the prior art to isolate 5(S) ramipril ran counter to the Supreme Court' s decision in KSR. The court stated: [r]equiring an explicit teaching to purify the 5(S)-stereoisomer from a mixture in which it is the active ingredient is precisely the sort of rigid application of the TSM test that was criticized in KSR. Id. at 1301 (See MPEP 2143).
Further regarding claim 9, Applicant is reminded that H vs. Me is considered an obvious modification in the absence of superior, unexpected results. Therefore, when the methylene group in parentheses in structure V is absent (corresponding to R1 = Me), the compounds are obvious for the reasons outlined above.
Further regarding claim 12, at least the compounds below, in particular, are obvious for the reasons outlined above:
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Applicant is further advised that 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).
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Chaoyang et al. (CN 1371912 A – previously cited) (“Chaoyang”); as applied to claims 1, 3-4, 6, 8-10, 12; in view of Layton et al. (JAMA Intern Med., 2015, 175, 1187-1196 – previously cited) (“Leyton”).
The teachings of Chaoyang are disclosed above and incorporated herein.
While Chaoyang does not teach a dosage form comprising their compounds in injection, patch, or gel forms (claim 14), the teachings of Layton are relied upon for these disclosures.
Layton discloses a comparative study of the safety of different testosterone dosage forms, disclosing that compared with men using gel testosterone initiators, injections had a higher hazard for cardiovascular events, hospitalization, and death. Compared with gels, patches did not confer increased hazards of cardiovascular events, hospitalization, or death (results, page 1187).
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to design a dosage form comprising Chaoyang’s steroid compounds in the form of a gel or a patch. One of ordinary skill would have been motivated to do so in view of Layton’s disclosure that gel and patch testosterone initiators resulted in increased safety for patients, reporting reduced cardiovascular events, hospitalizations, and deaths. One of ordinary skill would have had a reasonable expectation of success in view of Chaoyang’s disclosure of their related steroid compounds; further in view of Layton’s disclosure of the rates of possible complications (Table 1, page 1190).
Response to Arguments
Claims
Claim amendments are acknowledged and have been entered. No new matter has been introduced.
Specification
Applicant’s arguments, see page 20, filed 03/17/2026, with respect to objections to the specification have been fully considered and are persuasive. The objections to the specification have been withdrawn.
Claim Objection
Applicant’s arguments, see page 20-21, filed 03/17/2026, with respect to objections to the claims over the definitions of group - - -Me in the claims have been fully considered and are persuasive. These objections have been withdrawn.
Applicant’s arguments with respect to the different definitions of Ra in the claim are not persuasive. This objection is maintained.
Applicant argues the variable is clearly defined and immediately after the variable is presented and separated by a semicolon, and that there is no ambiguity.
This is not persuasive. A single variable cannot be defined as different things within the claims.
Claim Rejections - 35 USC § 102
Applicant’s arguments, see page 21, filed 03/17/2026, with respect to 35 USC § 102 rejections have been fully considered and are persuasive. The 35 USC § 102 rejections have been withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s arguments, see page 21, filed 03/17/2026, with respect to 35 USC § 103 rejections have been fully considered and are persuasive. The 35 USC § 103 rejections have been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of claim amendments, over Chaoyang et al.; and Chaoyang et al. in view of Layton et al.; as presented herein.
With regards to Chaoyang, Applicant argues that a POSITA would not have considered to modify Chaoyang’s core to comprise a methyl in the position corresponding to instant R1, because they do not teach or suggest modifying the steroid core of the compound. Applicant further states Chaoyang doesn’t teach a method by which the hydrogen at C7 can be replaced by methyl and cites the MPEP to say:
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And further states that Chaoyang provides no hint as to how to functionalize this position.
Applicant further argues that Leyton does not cure the deficiencies of Chaoyang.
In response to applicant’s argument that there is no teaching, suggestion, or motivation to combine the references, the examiner recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art. See In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), and KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007).
In this case, Chaoyang discloses the androsterol alkyl carbonate compounds below (page 1 of original doc., and page 1 of translated doc.), useful for oral assimilation of nutrients and proteins (page 2, para. 1 of translated doc.), which reads on metabolic diseases, which is one of the intended conditions to be treated by the instant compounds. Chaoyang’s disclosure renders the instantly claimed compounds obvious when: R’ is -OC(O)OCH3, or -OC(O)O-nC3H7, or -OC(O)O-nC4H9, or -OC(O)O-Ph, or -OC(O)O-cyclohexyl (corresponding to instant R2 being -C(O)ORa, and Ra being aliphatic, aromatic, or an organic functional group); and R can be a carbonyl (=O). Thus, Chaoyang discloses a narrow genus of compounds which is encompassed by the instantly elected genus when instant Y is aliphatic; X is H; R3-9 are H; and R11 is absent.
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While Chaoyang does not specifically teach their group corresponding to instant R1 being -Me (reading on alkyl/ lower alkyl/ organic functional group); Applicant is reminded that H vs. Me is considered an obvious modification in the absence of superior, unexpected results.
Therefore, replacing the H corresponding to instant position R1 in Chaoyang’s compounds with a methyl group is an obvious modification in the absence of superior unexpected results. Thus, one having ordinary skill in the art would have found the claimed compounds prima facie obvious, since they are generically embraced by Chaoyang’s disclosed formula. The requisite motivation for arriving at the claimed compounds stems from the fact that they fall within the generic class of compounds disclosed by Chaoyang as useful for the treatment of oral assimilation of nutrient issues (reading on metabolic disease). Accordingly, one having ordinary skill in the art would have been motivated to prepare any of the compounds embraced by the disclosed generic formula, including those encompassed by the claims.
Applicant is reminded that 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. 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. Applicant is further reminded that 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 response to applicant's argument that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., a method by which the hydrogen at C7 can be replaced by methyl) are not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Furthermore, C7 substituted steroids are known in the art, "A person of ordinary skill in the art is also a person of ordinary creativity, not an automaton." KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 421, 82 USPQ2d 1385, 1397 (2007). A person with ordinary skill has good reason to pursue known options within his or her technical grasp. Note: MPEP 2143(E) KSR, 550 U.S. at 421, 82 USPQ2d at 1397.
MPEP 716.01(c) makes clear that “[t]he arguments of counsel cannot take the place of evidence in the record” (In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965)). It is noted that the responses above should not be construed as an invitation to file an after final declaration. See MPEP 715.09.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JACKSON J HERNANDEZ whose telephone number is (571)272-5382. The examiner can normally be reached Mon - Thurs 7:30 to 5.
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/JACKSON J HERNANDEZ/Examiner, Art Unit 1627
/SARAH PIHONAK/Primary Examiner, Art Unit 1627
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