DETAILED ACTION
This office action is in response to applicant’s filing dated March 27, 2026.
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 Under 37 CFR 1.114
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on March 27, 2026 has been entered.
Status of Claims
Claims 1-20 are pending in the instant application. Acknowledgement is made of Applicant's remarks and amendments filed February 28, 2025. Acknowledgement is made of Applicant’s amendment of claim 1.
Applicants elected without traverse Group I, drawn to an ester-linked statin derivative of formula (FIa) as the elected invention and Compound (FId) also referred to as Compound 8 (DZ1-SIM):
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as the single disclosed compound of Formula (FIa) species in the reply filed on November 14, 2023. The requirement is still deemed proper. Claims 9-20 remain withdrawn.
Claims 1-8 are presently under examination as they relate to the elected species: Compound (FId):
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and a compound.
Priority
The present application is a CON of US Application No. 16/925,582 filed on July 10, 2020, which claims benefit of US Provisional Application Nos. 62/873,277 and 62/873,293 filed on July 12, 2019.
Withdrawn Objections and/or Rejections
Double Patenting
The provisional rejection of claims 1-8 on the ground of nonstatutory double patenting as being unpatentable over claims 29 and 30 of copending Application No. 16/343,732 (reference application) has been rendered moot in view of the abandonment of Application No. 16/343,732 dated March 9, 2026.
Maintained Objections and/or Rejections
Claim Rejections - 35 USC § 103
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 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 1-8 are rejected under 35 U.S.C. 103 as being unpatentable over Yin et al (WO 2018/075994 A1, published April 26, 2018, cited in a previous Office Action).
Regarding claims 1-7, Yin teaches a sensitizer compound which is a DZ-DRG amide or ester conjugate wherein a DZ-residue of formula (FI) via an amide or ester bond is linked to a drug (DRG) wherein the conjugated drug (DRG is simvastatin (claim 1):
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Regarding claim 8, Yin teaches a pharmaceutical composition comprising a sensitizer compound which is DZ-DRG amide or ester conjugate and at least one pharmaceutically acceptable carrier, wherein a CA-residue of Formula FI, via an amide or ester bond is linked to the residue of a DRUG; wherein the conjugated DRG of the sensitizer is simvastatin (SIM) [0016].
Moreover, Yin teaches a sensitizer Compound 6 ([0175] Scheme 2):
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Compound 6 differs from the instantly elected compound in the positions denoted by the arrows labeled A and B. In particular, the DZ residue of Compound 6 is linked to the simvastatin residue with a propylene (A) amide (B) linker, while the DZ residue of the instant claims is linked to the simvastatin residue with an ethylene ester linker. With regard to the ester vs amide linkage at position B, Yin contemplates the use of either bond to form conjugate compounds [0011]. With regard to the ethylene vs propylene linker, compounds which are 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). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978). Moreover, MPEP 2143.I.B. states:
It should be noted that the lead compound cases do not stand for the proposition that identification of a single lead compound is necessary in every obviousness rejection of a chemical compound. For example, one might envision a suggestion in the prior art to formulate a compound having certain structurally defined moieties, or moieties with certain properties. If a person of ordinary skill would have known how to synthesize such a compound, and the structural and/or functional result could reasonably have been predicted, then a prima facie case of obviousness of the claimed chemical compound might exist even without identification a particular lead compound. As a second example, it could be possible to view a claimed compound as consisting of two known compounds attached via a chemical linker. The claimed compound might properly be found to have been obvious if there would have been a reason to link the two, if one of ordinary skill would have known how to do so, and if the resulting compound would have been the predictable result of the linkage procedure.
In the instant case, as taught by Yin conjugate compounds comprising a DZ-residue and a simvastatin residue was known in the art (i.e., a compound comprising two known compounds DZ and simvastatin attached via a chemical linker). Thus, it was known in the art to link these two compounds and it would be obvious to utilize known linkage procedures to arrive at the instantly elected compound with a reasonable expectation of success.
Taken together, all this would result in the compounds of claims 1-8 with a reasonable expectation of success.
Response to Arguments
Applicant argues:
The rejection does not adequately address the specific elected species. The Office Action treats the elected species, Compound FId, largely as a routine variant of Yin's Compound 6. Respectfully, that framing is too generalized. The question is not whether Yin broadly discloses DZ-simvastatin conjugates or whether amide and ester linkages were each known in the abstract. Rather, the relevant question is whether Yin teaches or suggests the specific elected ester-linked architecture now claimed, and whether a person of ordinary skill in the art would have been motivated to select that architecture with a reasonable expectation of success. The Office Action overstates the similarity between Yin's Compound 6 and the Elected Species. The Office Action characterizes the elected species as differing from Yin's Compound 6 only by use of an ethylene linker instead of a propylene linker and by an ester rather than an amide linkage. Even accepting that description for purposes of discussion, those are not trivial differences on this record. The Office Action's rationale treats the ester-versus-amide distinction as if it were merely an interchangeable bond substitution. The present application, however, does not present those alternatives as interchangeable. Instead, the specification distinguishes ester-linked statin derivatives (ELSD) and amide-linked statin derivatives (ALSD) as different design concepts associated with different release behavior. The Office Action treats Yin's Compound 6 as effectively the same compound except for bond type and linker length, that treatment does not adequately account for the specific attachment architecture reflected in the elected species. Applicant does not rely on functional characterization alone, but on the structural distinctions reflected in the elected compound as claimed.
Examiner's response:
The above argument has been carefully considered and has not been found persuasive.
The Examiner acknowledges that Yin does not explicitly teach that the DZ residue of the instant claims is linked to the simvastatin residue with an ethylene ester linker. However, as set forth above, Yin teaches structurally similar compounds comprising a structurally similar DZ residue linked to a simvastatin residue with a linker and that amide and ester linkers are alternatively useful for producing DZ-simvastatin conjugate drugs. As set forth above, with regard to the ester vs amide linkage at position B, Yin contemplates the use of either bond to form conjugate compounds. The Examiner notes that the linker is attached at two positions, one to the DZ and the other to the simvastatin. Yin teaches simvastatin can be attached via an amide or ester linkage [0012]. A skilled artisan would have easily envisaged the use of either an amide or ester linker to conjugate the simvastatin directly to the DZ-residue or to the linker between the DZ-residue and the simvastatin since Yin teaches conjugating simvastatin via either an amide or ester linkage. With regard to the ethylene vs propylene linker, compounds which are 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). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978).
Moreover, as set forth above, it could be possible to view a claimed compound as consisting of two known compounds attached via a chemical linker. The claimed compound might properly be found to have been obvious if there would have been a reason to link the two, if one of ordinary skill would have known how to do so, and if the resulting compound would have been the predictable result of the linkage procedure. In the instant case, as taught by Yin conjugate compounds comprising a DZ-residue and a simvastatin residue was known in the art (i.e., a compound comprising two known compounds DZ and simvastatin attached via a chemical linker). Thus, it was known in the art to link these two compounds and it would be obvious to utilize known linkage procedures to arrive at the instantly elected compound with a reasonable expectation of success.
Applicant argues:
The comparative data in the application undercut predictability. The present application provides comparative evidence inconsistent with the Office Action's predictability premise. The most probative evidence is not the comparison between the conjugates and simvastatin alone, but the application's own comparison between ester-linked and amide-linked DZ-simvastatin conjugates. The application reports the following IC50 values: in H446 cells, DZ-SIM- ester 3.4 µM, DZ-SIM-amide 3.7 µM, and simvastatin 39 µM; and in A549 cells, DZ-SIM-ester 5.4 µM, DZ-SIM-amide 5.7 µM, and simvastatin > 50 µM. Notably, in the cisplatin-resistant A549DDP cell line, the elected ester-linked conjugate demonstrates a material and unexpected nearly threefold increase in potency over the amide-linked variant (2.1 µM vs. 6.1 µM). These data show that converting between ester- linked and amide-linked architectures in this compound class can materially affect activity. Second, the fact that the magnitude and direction of the effect are not uniform across all cell lines itself underscores the unpredictability of the structural change.
Examiner's response:
The above argument has been carefully considered and has not been found persuasive.
MPEP 716.02 states:
Any differences between the claimed invention and the prior art may be expected to result in some differences in properties. The issue is whether the properties differ to such an extent that the difference is really unexpected. In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). The evidence relied upon should establish "that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance." Ex parte Gelles, 22 USPQ2d 1318, 1319 (Bd. Pat. App. & Inter. 1992). In the instant case, as noted in the response, the IC50 in H446 cells of DZ-SIM- ester and DZ-SIM-amide is 3.4 µM and 3.7 µM, respectively; and in IC50 A549 cells of DZ-SIM- ester and DZ-SIM-amide is 5.4 µM and 5.7 µM. Thus, there appears to be very little difference between the ester and amide compounds in these cell lines. The Examiner acknowledges that there appears to be a larger difference in IC50 in the cisplatin-resistant A549DDP cell line, 2.1 µM vs. 6.1 µM. In a review of the specification, the instant specification teaches for three different cell lines, when comparing the IC50 for the THSD (ELSD/Yin compound and ALSD/claimed compound) the trend is similar: the IC50 for the THSD (ELSD and ALSD) range from about 2 to about 12µM; thus both ALSD and ELSD reduce cell viability and inhibit the growth of prostate cancer cells better than unconjugated statin (see paragraph [0284]). In a review of Fig 7A-I, DZ-ester and DZ-amide lines appear to be similar or very close for Fig 7A-D and F-I. The data appears to show slight differences between the compounds in different cancers, which is not unexpected.
Moreover, MPEP 716.02(d) states:
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980). Even assuming arguendo that the data provided would support the alleged unexpected properties. The data provided for single conjugate compound is insufficient to support unexpected properties for the full scope of the claims.
Applicant argues:
The Office Action cites In re Wilder for the proposition that the propylene and ethylene linkers are homologs of sufficiently close structural similarity. Even assuming arguendo that a one- carbon linker change could in some circumstances support a presumption of similar properties, that principle does not answer the more important question presented here: whether the elected ester-linked architecture would have been selected and expected to behave predictably relative to Yin's amide-linked Compound 6. In other words, the rejection conflates two separate issues. A linker-length variation does not eliminate the need to explain why the amide-containing arrangement of Yin would have been replaced with the elected ester-linked architecture, nor does it negate the application's comparative evidence showing that ester-linked and amide-linked conjugates are not merely interchangeable forms of the same construct.
Examiner's response:
The above argument has been carefully considered and has not been found persuasive.
Regarding the argument that no reasonable expectation of success has been established, [c]onclusive proof of efficacy is not required to show a reasonable expectation of success. OSI Pharm., LLC v. Apotex Inc., 939 F.3d 1375, 1385, 2019 USPQ2d 379681 (Fed. Cir. 2019) ("To be clear, we do not hold today that efficacy data is always required for a reasonable expectation of success. Nor are we requiring ‘absolute predictability of success.’"); Acorda Therapeutics, Inc. v. Roxane Lab., Inc., 903 F.3d 1310, 1333, 128 USPQ2d 1001, 1018 (Fed. Cir. 2018). See MPEP 2143.02. Absolute predictability is not a necessary prerequisite to a case of obviousness. Rather, a degree of predictability that one of ordinary skill would have found to be reasonable is sufficient. The Federal Circuit concluded that "[g]ood science and useful contributions do not necessarily result in patentability." Id. at 1364, 83 USPQ2d at 1304. See MPEP 2145.
As set forth above, Yin teaches structurally similar compounds comprising a structurally similar DZ residue linked to a simvastatin residue with a linker and that amide and ester linkers are alternatively useful for producing DZ-simvastatin conjugate drugs. As set forth above, with regard to the ester vs amide linkage at position B, Yin contemplates the use of either bond to form conjugate compounds. The Examiner notes that the linker is attached at two positions, one to the DZ and the other to the simvastatin. Yin teaches simvastatin can be attached via an amide or ester linkage [0012]. A skilled artisan would have easily envisaged the use of either an amide or ester linker to conjugate the simvastatin directly to the DZ-residue or to the linker between the DZ-residue and the simvastatin, since Yin teaches conjugating simvastatin via either an amide or ester linkage. With regard to the ethylene vs propylene linker, compounds which are 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). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978).
Moreover, as set forth above, it could be possible to view a claimed compound as consisting of two known compounds attached via a chemical linker. The claimed compound might properly be found to have been obvious if there would have been a reason to link the two, if one of ordinary skill would have known how to do so, and if the resulting compound would have been the predictable result of the linkage procedure. In the instant case, as taught by Yin conjugate compounds comprising a DZ-residue and a simvastatin residue was known in the art (i.e., a compound comprising two known compounds DZ and simvastatin attached via a chemical linker). Thus, it was known in the art to link these two compounds and it would be obvious to utilize known linkage procedures to arrive at the instantly elected compound with a reasonable expectation of success.
Modified Objections and/or Rejections
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 USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The 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/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1-8 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-21 of U.S. Patent No. 11,878,000. Although the claims at issue are not identical, they are not patentably distinct from each other because:
The instant claims are directed to an ester-linked statin derivative of formula (FIa):
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The previously granted claims are directed to a method of sensitizing cancer comprising administering a sensitizer compound wherein the sensitizer compound is a DA1-drug amide or ester conjugate (claim 1):
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wherein the drug is a statin (claim 2), ester- or amide-conjugated Simvastatin (SIM) (claim 3); DZ1-SIM ester sensitizer and DZ1-SIM amide sensitizer (claim 9).
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(col 7 and 8).
DZ1-SIM amide sensitizer differs from the instantly elected compound in the positions denoted by the arrows labeled A and B. In particular, DZ1-SIM amide sensitizer is linked to the simvastatin residue with a propylene (A) amide (B) linker, while the DZ residue of the instant claims is linked to the simvastatin residue with an ethylene ester linker. With regard to the ester vs amide linkage at position B, the previously allowed claims contemplates the use of either bond to form conjugate compounds with simvastatin. With regard to the ethylene vs propylene linker, compounds which are 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). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978). Moreover, MPEP 2143.I.B. states:
It should be noted that the lead compound cases do not stand for the proposition that identification of a single lead compound is necessary in every obviousness rejection of a chemical compound. For example, one might envision a suggestion in the prior art to formulate a compound having certain structurally defined moieties, or moieties with certain properties. If a person of ordinary skill would have known how to synthesize such a compound, and the structural and/or functional result could reasonably have been predicted, then a prima facie case of obviousness of the claimed chemical compound might exist even without identification a particular lead compound. As a second example, it could be possible to view a claimed compound as consisting of two known compounds attached via a chemical linker. The claimed compound might properly be found to have been obvious if there would have been a reason to link the two, if one of ordinary skill would have known how to do so, and if the resulting compound would have been the predictable result of the linkage procedure.
In the instant case, the DZ1-conjugated sensitizer compounds comprising a DZ-residue and a simvastatin residue was known in the art (i.e., a compound comprising two known compounds DZ and simvastatin attached via a chemical linker). Thus, it was known in the art to link these two compounds and it would be obvious to utilize known linkage procedures to arrive at the instantly elected compound with a reasonable expectation of success.
Claims 1-8 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-19 of U.S. Patent No. 12,121,510 B2. Although the claims at issue are not identical, they are not patentably distinct from each other because:
The instant claims are directed to an ester-linked statin derivative of formula (FIa).
The previously allowed claims are directed to a sensitizer compound which is a DZ-DRG amide or ester conjugate of formula (FI) or (FII):
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wherein the conjugated drug is Simvastatin (SIM) (claim 1); wherein the sensitizer is DZ1-SIM ester sensitizer or DZ1-SIM amide sensitizer (claim 5).
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(col 11 and 12).
DZ1-SIM amide sensitizer differs from the instantly elected compound in the positions denoted by the arrows labeled A and B. In particular, DZ1-SIM amide sensitizer is linked to the simvastatin residue with a propylene (A) amide (B) linker, while the DZ residue of the instant claims is linked to the simvastatin residue with an ethylene ester linker. With regard to the ester vs amide linkage at position B, the previously allowed claims contemplates the use of either bond to form conjugate compounds with simvastatin. With regard to the ethylene vs propylene linker, compounds which are 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). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978). Moreover, MPEP 2143.I.B. states:
It should be noted that the lead compound cases do not stand for the proposition that identification of a single lead compound is necessary in every obviousness rejection of a chemical compound. For example, one might envision a suggestion in the prior art to formulate a compound having certain structurally defined moieties, or moieties with certain properties. If a person of ordinary skill would have known how to synthesize such a compound, and the structural and/or functional result could reasonably have been predicted, then a prima facie case of obviousness of the claimed chemical compound might exist even without identification a particular lead compound. As a second example, it could be possible to view a claimed compound as consisting of two known compounds attached via a chemical linker. The claimed compound might properly be found to have been obvious if there would have been a reason to link the two, if one of ordinary skill would have known how to do so, and if the resulting compound would have been the predictable result of the linkage procedure.
In the instant case, the DZ1-conjugated sensitizer compounds comprising a DZ-residue and a simvastatin residue was known in the art (i.e., a compound comprising two known compounds DZ and simvastatin attached via a chemical linker). Thus, it was known in the art to link these two compounds and it would be obvious to utilize known linkage procedures to arrive at the instantly elected compound with a reasonable expectation of success.
Response to Arguments
Since a modified rejection was issued (see above), it is the Examiner’s belief that most of the arguments presented by Applicant have been considered/answered in the rejection itself.
Conclusion
Claims 1-8 are rejected.
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RAYNA B RODRIGUEZ whose telephone number is (571)272-7088. The examiner can normally be reached 8am-5:00pm, Monday - Thursday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy L Clark can be reached at 571-272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Rayna Rodriguez/ Primary Examiner, Art Unit 1628
Prosecution Insights