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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 1/26/2026 has been entered.
Election/Restrictions
Claim 3, 4, 25, 32, 34, and 36 withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected Group II (previously referred to as Group IV) and nonelected compound of Genus A there being no allowable generic or linking claim. Applicant's election with traverse of Group III in the reply filed on 2/20/2025 was acknowledged in the OA of 10/24/2025, but was still deemed proper and therefore made FINAL.
Status of Claims
Cancelled: 5-7, 9, 10, 19, 20, 22, 26-31, 33, 35, 37-41
Withdrawn: 3, 4, 25, 32, 34, 36
Examined Herein: 1, 2, 8, 11-18, 21, 23, 24
Priority
Priority to PRO 62/830,853 filed on 3/20/2019 and PCT/CA2019/051368 filed on 9/25/2019 is
acknowledged.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 6/20/2022 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Drawings
The drawings filed on 9/20/2021 are accepted.
Withdrawn Rejections
The rejection of claims 1, 2 and 8 under 35 U.S.C. 103 over Gracia and Pal is hereby withdrawn because upon further search and consideration, additional art has been identified and is applied in the new ground of rejection set forth below.
The rejection of claims 1, 2 and 8 under 35 U.S.C. 103 over Lonnon and Gracia is hereby withdrawn because upon further search and consideration, additional art has been identified and is applied in the new ground of rejection set forth below.
The rejection of claims 1, 2, 8, and 14-18 under 35 U.S.C. 103 over Gracia, Pal, and Spreckelmeyer is hereby withdrawn because upon further search and consideration, additional art has been identified and is applied in the new ground of rejection set forth below.
The rejection of claims 1, 2, 8, 11-18, 21, and 23 under 35 U.S.C. 103 over Gracia, Pal, and Spreckelmeyer, and Burak is hereby withdrawn because upon further search and consideration, additional art has been identified and is applied in the new ground of rejection set forth below.
The rejection of claims 1, 2, 8, 14-18, and 24 under 35 U.S.C. 103 over Gracia, Pal, and Spreckelmeyer, and Welt is hereby withdrawn because upon further search and consideration, additional art has been identified and is applied in the new ground of rejection set forth below.
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 1, 2, 8, 11, 12, 14-16, 18, 21, 23, and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Gale (US 2019/0001003 A1, Published 1/3/2019).
With respect to claim 1, Gale discloses the following chelating agent:
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559
539
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[Gale, 0262]
This chelating agent is a species encompassed by Formula (VI) and (XVIII):
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224
338
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[Gale, 0040; see also 0094, 0213, 0268]
wherein:
R1 is a 6-membered cycloalkylene [0043]
R2, R3, and R4 is:
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112
115
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[0044 (VII)]
R6 is H [0045]
DG is:
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50
34
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[0050 (XI)]
Q (at 3) is CH [0053]
Y (at 4) is CZ1 [0052]
Z1 is COOH [0054]
Y (at 5) is CH [0052]
Y (at 6) is CH [0052]
With respect to claim 8, Gale discloses R1 (which corresponds to DG) may be optionally substituted with one or more heteroatoms, as “Y” or “Q” may be N, O, or S. [Gale, 0052, 0053]
With respect to claim 11, Gale discloses a metal chelate comprising the aforementioned chelating agent and a metal, wherein the metal comprises an actinide, a lanthanide, or a rare earth metal. [Gale, 0094 (XVII), 0112, 0269, 0333]
With respect to claim 12, Gale discloses a metal chelate comprising the aforementioned chelating agent and a metal, wherein the metal is an unstable isotope of Y(III), Bi(III) or Lu(III). [Gale, 0112, 0269, 0333] The unstable isotopes of Y(III), Bi(III), and Lu(III) include 90Y, 213Bi, and 177Lu, respectively.
With respect to claim 14, Gale discloses an in vivo radioisotope targeting construct comprising a targeting moiety coupled to the chelating agent. [Gale, 0300, 0301, 0330 (XXXII)]
With respect to claim 15, Gale discloses the targeting construct comprises a linker interposing the targeting moiety and the chelating agent. [Gale, 0301, 0329, 0330 (XXXII), 0331]
With respect to claim 16, Gale discloses the targeting moiety comprises a peptide, or a molecule that recognizes cell surface receptors. [Gale, 0306-0322]
With respect to claim 18, Gale discloses the linker may comprise the following structure:
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104
177
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[Gale, 0222-0223]
With respect to claim 21, Gale discloses an in vivo radioisotope targeting chelate construct comprising the in vivo radioisotope targeting construct and a metal, wherein the metal is an unstable isotope of Y(III), Bi(III) or Lu(III). [Gale, 0112, 0269, 0300-0302, 0333] The unstable isotopes of Y(III), Bi(III), and Lu(III) include 90Y, 213Bi, and 177Lu, respectively.
With respect to claim 23, Gale discloses an in vivo radioisotope targeting chelate construct comprising the in vivo radioisotope targeting construct and a metal, wherein the metal comprises La, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Y, or Bi. [Gale, 0112, 0269, 0300-0302, 0333]
With respect to claim 24, Gale discloses a pharmaceutical composition comprising the in vivo radioisotope targeting construct and a pharmaceutically acceptable carrier, excipient or vehicle. [Gale, 0344, 0346]
Gale does not explicitly disclose a chelating agent of instant formula (I).
However, with respect to claim 1, 2, and 23, Gale discloses R2, R3, and R4, may each independently be:
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214
187
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[0044, 0224 (VIII)]
wherein:
R6 is H [0045, 0225]
X is N [0046, 0226]
W (at 2) is CZ [0047, 0227]
Z is COOH [0048, 0228]
W (at 3) is CH [0047, 0228]
W (at 4) is CH [0047, 0228]
W (at 5) is CH [0047, 0228]
Additionally, Gale discloses DG may independently be:
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50
34
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[0050, 0233 (XI)]
or any constitutional isomer thereof [0051], wherein:
Q (at 2) is CZ1 [0053, 0235]
Z1 is COOH [0054, 0236]
Y (at 3) is CH [0052, 0234]
Y (at 4) is CH [0052, 0234]
Y (at 5) is CH [0052, 0234]
Furthermore, Gale discloses R1 may be a 6-membered (dimethyl)heteroarylene, including dimethyl-pyridinyl. Gale further discloses R1 may be bound to the adjacent nitrogen via the 1,2 or 1,3 positions on R1, or any constitutional isomers thereof. [Gale, 0043, 0177, 0222, 0233]
Modifying the chelating agent disclosed by Gale by replacing R1 with dimethylpyridinyl, R2, R3, and R4 with 6-ethylpicolinic acid, and DG with 6-methylpicolinic acid results in a compound falling within the scope of claim 1, 2, and 23, including a compound having the following structures:
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257
335
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253
320
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[Structure edited by Examiner and depicts the modification of the compound disclosed by Gale. This depiction is for illustrative purposes only]
It would be obvious to one of ordinary skill in the art to modify the chelating agent disclosed by Gale by replacing R1 with dimethylpyridinyl, R2, R3, and R4 with 6-ethylpicolinic acid, and DG with 6-methylpicolinic acid and have a reasonable expectation of success. Gale discloses a chelating agent encompassed by Formula (VI) and (XVIII) comprising moieties represented by R1, R2, R3, R4, and DG, wherein R1 is a 6-membered cycloalkylene, R2, R3, and R4 are carboxyl, and DG is 6-methylnicotinic acid. However, Gale discloses Formula (VI) and (XVIII) encompasses an embodiment wherein R1 is dimethylpyridinyl, R2, R3, and R4 are 6-ethylpicolinic acid, and DG is 6-methylpicolinic acid. In view of this express teaching, it is reasonable to expect the chelating agent disclosed by Gale may be modified by replacing R1 with dimethylpyridinyl, R2, R3, and R4 with 6-ethylpicolinic acid, and DG with 6-methylpicolinic acid. One would have been motivated to do so because the selection of a known substituent based on its suitability for its intended use is prima facie obvious. MPEP 2144.07. Therefore, the selection of the aforementioned substituents based on their suitability for use as a R1, R2, R3, R4, or DG moiety under Formula (VI) and (XVIII) disclosed by Gale is prima facie obvious.
Claims 1 and 2 are rejected under 35 U.S.C. 103 as being unpatentable over Forgacs (Mono‑, Bi‑, and Trinuclear Bis-Hydrated Mn2+ Complexes as Potential MRI Contrast Agents, 9/23/2015, Inorganic Chemistry, 54, 9576-9587), in view of Brown (Bioisosteres in Medicinal Chemistry, 2012, First Edition, Wiley-VCH Verlag GmbH & Co. KGaA).
With respect to claim 1, Forgacs discloses the following contrast agent:
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2142
2840
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[Forgacs, Page 9577, Chart 1]
wherein:
R is H
R1 is:
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168
142
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Forgacs does not disclose the backbone of the chelating agent is pyridine.
However, with respect to claim 1, Brown discloses benzene and pyridine are bioisosteres. [Brown, Page 7, Table 1.3] Bioisosteres are functional groups sharing similar physical or chemical properties and maintaining similar activity. [Brown, Page 15, Paragraph 1] Moreover, bioisosteric replacement is a well-known technique used by medicinal chemists that involves making small modifications to a lead compound to improve some of its properties, such as pharmacological activity, selectivity, and pharmacokinetics. This is often achieved by replacing a functional group with a biosisosteric equivalent. [Brown, Page 15, Paragraph 1; See also Page 9, Paragraph 2 & Page 14, Paragraph 1]
Modifying the compound disclosed by Forgacs by replacing benzene with pyridine results in a compound falling within the scope of claim 1 and 2, including the following:
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378
523
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[Structure edited by Examiner and depicts the modification of mX(H2dpama)2 by replacing benzene with pyridine. This depiction is for illustrative purposes only]
It would be obvious to one of ordinary skill in the art to modify the compound disclosed by Forgacs by replacing benzene with pyridine and have a reasonable expectation of success.
Forgacs discloses a chelating agent, mX(H2dpama)2, comprising a benzene backbone.
Brown discloses benzene and pyridine are bioisosteres, or functional groups sharing similar physical or chemical properties and maintaining similar activity. Moreover, Brown discloses bioisosteric replacement is a well-known technique used by medicinal chemists that involves making small modifications to a lead compound to improve some of its properties, and is achieved replacing a functional group with a bioisosteric equivalent. Thus, Brown establishes that benzene and pyridine are bioisosteres and bioisosteric replacement is a well-known technique. Accordingly, the combined teachings of Forgacs and Brown suggest that replacing benzene with pyridine results in a backbone with similar physical properties. Therefore, it is reasonable to expect the compound disclosed by Forgacs may be modified by replacing benzene with pyridine. One would have been motivated to do so because it is prima facie obvious to combine teachings when some advantage or expected beneficial result would have been produced by their combination. MPEP 2144(II). In the instant case, Forgacs discloses the chelating agent may be used for MRI visualization of blood vessels and to improve the residence time of the agent in the blood pool. [Forgacs, Page 9584, Col. 1, Paragraph 3] Brown discloses the discovery and development of a candidate for clinical evaluation is a long process that involves small modifications to a lead compound to improve some of its properties, such as pharmacological activity, selectivity, and pharmacokinetics. This is often achieved by the medicinal chemists by replacing a functional group with groups sharing similar physical or chemical properties and maintaining similar activity. [Brown, Page 15, Paragraph 1] Therefore, one would have been motivated by the expectation that the aforementioned modification could improve some of the properties, such as pharmacological activity, selectivity, and pharmacokinetics of the pharmaceutical chelating agent disclosed by Forgacs.
Claims 1, 8, 11-16, 21, 23, and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Adam (US 2011/0313130 A1, Published 12/22/2011).
With respect to claim 1, Adam discloses the following chelating agent:
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426
528
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[Adam, 0255]
This chelating agent is a species encompassed by Formula (I):
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119
305
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[Adam, 0010, 0088]
wherein:
M is:
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31
93
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[0012, 0090]
Q4 is H [0013, 0091]
R1’ and R1 are each independently:
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381
331
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[0020, 0098]
Z1 is CH [0025, 0105]
Z2 is CH [0025, 0105]
R6 is H [0023, 0102]
Q1 and Q2 are each independently R [0013, 0091]
R is –(CHR2)pCOR3 [0019, 0097]
R2 is H [0021, 0099]
p is 1 [0028, 0107]
R3 is OH [0022, 0100]
With respect to claim 8, Adam discloses R1 (which corresponds to R1 and R1’ as disclosed by Adam) may optionally be substituted with one or more heteroatoms, as Z1 or Z2 may be N. [Adam, 0020, 0025, 0098, 0105]
With respect to claim 11, Adam discloses a metal chelate comprising the chelating agent and a metal, wherein the metal comprises an actinide, a lanthanide, or a rare earth metal. [Adam, 0055, 0056, 0118, 0119, 0149]
With respect to claim 12, Adam discloses a metal chelate comprising the chelating agent and a metal, wherein the metal comprises 225Ac, 213Bi, 89Zr, 90Y, or 177Lu. [Adam, 0056, 0119, 0149]
With respect to claim 13, Adam discloses a metal chelate comprising the chelating agent and a metal, wherein the metal comprises 225Ac. [Adam, 0056, 0119, 0149]
With respect to claim 14, Adam discloses an in vivo radioisotope targeting construct comprising a targeting moiety coupled to the chelating agent. [Adam, 0057, 0120-0123, 0149, 0160]
With respect to claim 15, Adam discloses the targeting construct comprises a linker interposing the targeting moiety and the chelating agent. [Adam, 0197]
With respect to claim 16, Adam discloses that the targeting moiety comprises a hapten, an antigen, an aptamer, an affibody, a protein, a peptide, an antibody, an antigen-binding fragment of an antibody, a peptidomimetic, a hormone, a growth factor, a cytokine, a molecule that recognizes cell surface receptors, or a lipophilic group. [Adam, 0057, 0120-0123, 0149, 0160]
With respect to claim 21, Adam discloses an in vivo radioisotope targeting chelate construct comprising the in vivo radioisotope targeting construct and a metal, 225Ac, 213Bi, 89Zr, 90Y, or 177Lu. [Adam, 0055-0057, 0119-0123, 0149, 0160]
With respect to claim 23, Adam discloses an in vivo radioisotope targeting chelate construct comprising the in vivo radioisotope targeting construct and a metal, Ac, Th, U, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Y, Sc, Zr, Ra, Pb, Bi, Po, or At. [Adam, 0055-0057, 0118-0123, 0149, 0160]
With respect to claim 24, Adam discloses a pharmaceutical composition comprising the in vivo radioisotope targeting construct and a pharmaceutically acceptable carrier. [Adam. 0124]
Adam does not explicitly disclose a chelating agent of instant formula (I).
However, with respect to claim 1, Adam further discloses M may be:
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31
93
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wherein:
A1 and A2 form together with the atoms to which they are a C6 heteroaryl, including pyridyl. [0018, 0066, 0158]
Adam further discloses Q1 and Q2 may each independently be:
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119
426
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[0044, 0047]
wherein:
R6 is carboxyl or semicarbazido [0054]
n is 1 [0027]
Modifying the compound disclosed by Adam by replacing M with dimethylpyridyl and Q1 and Q2 with toluic acid, results in a compound that is a position isomer of the compound of claim 1, including a compound having the following structure:
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377
786
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[Structure drawn by the Examiner using CAS Draw and depicts the modification of the compound disclosed by Adam. This depiction is for illustrative purposes only]
wherein, each R1 is independently:
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158
117
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or (a position isomer of)
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137
130
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.
However, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. Compounds which are position isomers are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. Therefore, the modified chelating agent disclosed by Adam is presumed to possess similar properties with the chelating agent of claim 1, in view of their very close structural similarities and similar utilities. MPEP 2144.09.
It would be obvious to modify the compound disclosed by Adam by replacing M with dimethylpyridyl and Q1 and Q2 with toluic acid, or isomers thereof, and have a reasonable expectation of success. Adam discloses a chelating agent encompassed by Formula (I) comprising moieties represented by M, Q1, and Q2, wherein M is propane and Q1 and Q2 are each carboxyl. However, Adam discloses Formula (I) encompasses an embodiment wherein M is dimethylpyridyl and Q1 and Q2 are each toluic acid. In view of this express teaching, it is reasonable to expect the chelating agent disclosed by Adam be modified replacing M with dimethylpyridyl and Q1 and Q2 with toluic acid. One would have been motivated to do so because the selection of a known substituent based on its suitability for its intended use is prima facie obvious. MPEP 2144.07. Therefore, the selection of the aforementioned substituents based on their suitability for use as a M, Q1, or Q2 moiety under Formula (I) disclosed by Adam is prima facie obvious. Moreover, one would have been motivated by the expectation that compounds similar in structure will have similar properties. MPEP 2144.09. Therefore, the selection of position isomers of the aforementioned substituents is prima facie obvious.
Claims 1, 8, 11-17, 21, 23, and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Adam, as applied to claims 1, 8, 11-16, 21, 23, and 24 above, and further in view of Spreckelmeyer (p-NO2–Bn–H4neunpa and H4neunpa–Trastuzumab: Bifunctional Chelator for Radiometal pharmaceuticals and 111In Immuno-Single Photon Emission Computed Tomography Imaging, 8/1/2017, Bioconjugate Chemistry, Page 2145-2159).
With respect to claim 1, 14, and 15, Adam discloses the teachings above.
With respect to claim 17, Adam discloses the targeting moiety of the in vivo radioisotope targeting construct comprises a hapten, an antigen, an aptamer, an affibody, a protein, a peptide, an antibody, an antigen-binding fragment of an antibody, a peptidomimetic, a hormone, a growth factor, a cytokine, a molecule that recognizes cell surface receptors, or a lipophilic group. [Adam, 0057, 0120-0123, 0149, 0160] Specifically, Adam discloses the targeting moiety is a monoclonal antibody having specificity for tumor cells. [Adam, 0087, 0120, 0160, 0162, 0177]
Adam does not disclose the targeting moiety comprises an anti-HER2 antibody or an anti-podocalyxin antibody.
However, with respect to claim 17, Spreckelmeyer discloses the complex, 111In-neunpa-trastuzumab, comprising a chelating agent, H4neunpa, conjugated to a targeting moiety/antibody/anti-HER2 antibody, trastuzumab, via a linker. [Spreckelmeyer, Abstract]
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273
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Spreckelmeyer discloses trastuzumab is an anti-HER2 monoclonal antibody with specificity for tumor cells. [Spreckelmeyer, Page 2146, Col. 2, Paragraph 1 and Page 2150, Col. 2, Paragraph 2]
Modifying the in vivo radioisotope targeting construct disclosed by Adam by selecting trastuzumab as the targeting moiety, results in the compound of claim 17.
It would be obvious to one of ordinary skill in the art to modify the in vivo radioisotope targeting construct by selecting trastuzumab as the targeting moiety and have a reasonable expectation of success. Adam discloses a complex comprising a chelating agent encompassed by Formula (I) and a targeting moiety, wherein a linker is interposed between the agent and moiety. Adam further discloses the targeting moiety is a monoclonal antibody having specificity for tumor cells. Spreckelmeyer discloses a complex comprising a chelating agent, H4neunpa, conjugated to an anti-HER2 antibody having specificity for tumor cells, trastuzumab, via a linker. Moreover, the compound disclosed by Spreckelmeyer is encompassed by Formula (I) disclosed by Adam. Thus, Spreckelmeyer establishes that conjugating a chelating agent of Formula (I) to trastuzumab is known in the art and trastuzumab is a monoclonal antibody having specificity for tumor cells. Accordingly, the combined teachings of Adam and Spreckelmeyer suggest that trastuzumab may serve as the targeting moiety in the complex disclosed by Adam. Therefore, it is reasonable to expect the chelating agent disclosed by Adam may be modified by selecting trastuzumab as the targeting moiety. One would have been motivated to do so because it is prima facie obvious to combine references when some advantage or expected beneficial result would have been produced by their combination. MPEP 2144(II). In the present case, Spreckelmeyer discloses trastuzumab is used to target HER2-expressing tumors. [Spreckelmeyer, Page 2150, Col. 2., Paragraph 2] Therefore, one would have been motivated by the expectation that selecting trastuzumab as the targeting moiety could enable the construct disclosed by Adam to target HER2-expressing tumors.
Response to Arguments
Applicant’s arguments, filed on 1/26/2026, with respect to the pending claim have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Oath/Declaration
The declaration under 37 CFR 1.132 filed on 1/26/2026 is insufficient to overcome the rejection of the pending claims based upon 35 U.S.C. 103 as set forth in the last Office action because the declaration is directed toward the teachings of Lonnon and Gracia, however, the new ground of rejection does not rely on either reference. Therefore, the declaration has been considered but is moot in view of the new ground of rejection.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KAILA A CRAIG whose telephone number is (703)756-4540. The examiner can normally be reached Monday-Friday 0800-1600.
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/K.A.C./Examiner, Art Unit 1618
/Michael G. Hartley/Supervisory Patent Examiner, Art Unit 1618
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