Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
This Application claims priority to U.S. Provisional Application No. 63/030,401, filed May 27, 2020.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on Jan. 26, 2026 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Status
Claims 1-2, 4-5, 7, 9-12, 26, 28, 30-33 and 103 are currently pending and subject to examination.
Withdrawn Rejections – Overcome by Amendment
The rejection of claims 30-33 under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends is withdrawn.
The above rejection was overcome by amendment.
Claim Rejections – 35 USC § 103 – Previously Presented
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.
The rejection of claim(s) 1-2, 4-5, and 28 under 35 U.S.C. 103 as being unpatentable over Scherrmann et al. (US 5,817,770 A, published October 6, 1998) and Ramakrishnan et al. (PLOS One, 7(7): e40518, p. 1-12, published July 10, 2012) is maintained.
The rejection of claim(s) 1-2, 4-5, 7, 9-12, 28, and 30-33 under 35 U.S.C. 103 as being unpatentable over Scherrmann et al. (US 5,817,770 A, published October 6, 1998) and Ramakrishnan et al. (PLOS One, 7(7): e40518, p. 1-12, published July 10, 2012), as applied to claims 1-2, 4-5 and 28 above, and further in view of Kimishima et al. (ACS Med. Chem. Lett., 2018, 9, 5, p. 411–416, published April 16, 2018) is maintained.
The rejection of claim(s) 1-2, 4-5, 26 and 28 under 35 U.S.C. 103 as being unpatentable over Scherrmann et al. (US 5,817,770 A, published October 6, 1998) and Ramakrishnan et al. (PLOS One, 7(7): e40518, p. 1-12, published July 10, 2012), as applied to claims 1-2, 4-5 and 28 above, and further in view of Asif et al. (American Journal of Pharmacological Sciences, 2014, Vol. 2, No. 1, 1-6, published 2014) is maintained.
Response to Arguments
The Applicant argues that Scherrmann teaches away from the claimed invention because Scherrman teaches an embodiment with an ethylene instead of succinyl linker and therefore does not explain how to reach the claimed ratio of at least 7.0 with a reasonable expectation of success (Remarks, p. 7). These arguments were fully considered but are not persuasive. Scherrmann does not criticize, discredit or otherwise discourage the claimed solution. In fact, the claimed solution falls within the genus of linkers disclosed by Scherrmann. Scherrmann teaches that the linker is a 1 to 10 atom aliphatic linker, preferably comprised of carbon atoms, usually 1 to 6 atoms in length, that preferably terminates in a carboxy group (Scherrmann, Specification, col. 2, cited in the prior office action on p. 4). The claimed linker would be expected to behave in the same way as the preferred embodiment of Scherrmann (cocaethylene-immunoconjugate shown on p. 4 of the prior office action) because it is a short aliphatic linker that terminates in a carboxy group which is bound in the same location on the cocaine analog as Scherrmann. The identity of the linker terminal (carboxy group) and protein (BSA) determines the ratio of cocaine moieties to BSA: “When used to bond to the antigenic protein to produce an immunogen, the carboxyl group will be activated for reaction with the protein in an aqueous medium.” (Scherrmann, Specification, col. 2, lines 25-28).
The Applicant argues that Ramakrishnan does not cure this problem because Ramakrishnan only teaches a conjugate made using a cocaine analog (Remarks, p. 7-8). These arguments were fully considered but are not persuasive. The norcocaine of Ramakrishnan would be expected to behave the same way as in the instant invention because the only difference between the norcocaine-succinyl-BSA conjugate of Ramakrishnan and the cocaine-succinyl-BSA conjugate of the instant invention is the place that the succinyl is bound, but Scherrmann teaches that linkers can be bound in the same way as in the instant invention to produce the intended result. A comparison between the claimed invention, Scherrmann and Ramakrishnan is shown below:
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Ramakrishnan, p. 3, Fig. 1;
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(cocaethylene-immunoconjugate of Scherrmann (drawn by Examiner))
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Instant Fig. 1.
A prima facie case of obviousness exists when compounds have very close similar structures and utilities as seen here:
A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) (discussed in more detail below) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1990) (discussed below and in MPEP § 2144) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. See also MPEP § 2144.08, subsection II.A.4.(c).
MPEP § 2144.09.
Scherrmann and Ramakrishnan demonstrate that succinyl-norcocaine and cocaethylene are not just structural analogs to cocaine-succinyl, but also functional analogs to cocaine-succinyl in the context of the claimed invention because they have the same utility. They can be bound to BSA and used to generate an immune response to cocaine.
The Applicant argues that one of ordinary skill in the art would not have a reasonable expectation of success to arrive at the exact ratio of 8.2 cocaine-succinyl moieties to BSA (Remarks, p. 9). These arguments were fully considered but are not persuasive. The newly claimed ratio of 8.2-8.3 cocaine-succinyl moieties per BSA falls within the range known in the prior art. Scherrmann teaches a ratio of 15 hapten molecules per BSA (Scherrmann, Specification, col. 6, lines 29-30). Ramakrishnan teaches that the ratio of hapten moeities per BSA is 7 (Ramakrishnan, p. 7, Table 2). A prima facie case of obviousness exists when ranges or amounts overlap or lie inside the ranges known in the prior art or are merely close (MPEP § 2144.05(I)). Furthermore, “[g]enerally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical.” (MPEP § 2144.05(II)). The claimed range of 8.2-8.3 falls within the range of between 7 and 15 known in the prior art. The Applicant has not demonstrated that the claimed range of 8.2-8.3 is critical for the outcome. Therefore, the claimed range was prima facie obvious at the time of filing.
Reiterated Rejection
Claim(s) 1-2, 4-5 and 28 is/are rejected under 35 U.S.C. 103 as being unpatentable over Scherrmann et al. (US 5,817,770 A, published October 6, 1998) and Ramakrishnan et al. (PLOS One, 7(7): e40518, p. 1-12, published July 10, 2012).
Claim 1 is directed towards a composition of matter comprising a plurality of cocaine-succinyl-BSA wherein the average ratio of cocaine-succinyl moieties to BSA is at least 7.0.
Scherrmann teaches cocaine analogs of the following formula bound to BSA:
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Scherrmann, Specification, column 2.
[AltContent: textbox (BSA)]In particular, Scherrmann teaches that the preferred hapten is a cocaethylene-immunoconjugate with the following structure:
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(drawn by examiner). Scherrmann teaches that the ratio of hapten to BSA molecules is about 15 (greater than at least 7): “The TNBS method indicated about 15 molecules of hapten per BSA.” (Scherrmann, Specification, col. 6, lines 29-30).
The preferred hapten conjugate of Scherrmann differs from the claimed cocaine-succinyl-BSA in two ways: first Scherrmann uses a cocaine analog, cocaethylene, second Scherrmann uses an ethylene linker instead of succinyl linker.
While Scherrmann uses cocaethylene, one of ordinary skill in the art would have a reasonable expectation of success to substitute cocaine for cocaethylene because Scherrmann teaches that these compounds are analogs and the goal is to administer the conjugate to stimulate the production of antibodies to cocaine:
In accordance with the subject invention compositions are provided which have the N-methylated tropane structure and are derivatives of the ethyl ester analog. The compounds find use as intermediates to the production of immunogens or as the immunogens. In addition, the antisera and monoclonal antibodies derived therefrom find use in the treatment of cocaine addiction and cocaine overdose, in assays for cocaine and the ethyl analog and other applications associated with cocaine.
Scherrmann, Specification, col. 2, lines 5-14.
While Scherrmann does not specifically teach the succinyl linker, one of ordinary skill in the art would have a reasonable expectation of success to use a succinyl linker because Scherrmann teaches alipathic linkers with 1 to 10 carbon atoms, primarily carbon atoms, with preferably 1 to 2 heteratoms, particularly oxygen or nitrogen (Scherrmann, Specification, col. 2, lines 42-50) and succinyl (which falls within the teachings of Sherrmann) is commonly known in the art as a linker for conjugating a cocaine analog to BSA.
For example, Ramakrishnan teaches norcocaine-succinyl-BSA conjugates for the same purpose:
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Ramakrishnan, p. 3, Fig. 1;
MST analysis of fluorescently tagged mAb08 binding to cocaine reveals an approximately 15 fold decrease in its equilibrium dissociation constant in 20–50% human serum compared with that in saline buffer. A similar trend was also found using enriched polyclonal antibodies purified from vaccinated mice and patient serum, for which we have used fluorescently tagged bovine serum albumin conjugated to succinyl norcocaine (BSA-SNC). This conjugate closely mimics both cocaine and the hapten used to raise these antibodies. The ITC data also revealed that cocaine has a moderate affinity of about 2 mM to 20% human serum and very little interaction with human serum albumin or nonspecific human IgG at that concentration range. In a SPR inhibition experiment, the binding of mAb08 to immobilized BSA-SNC was inhibited by cocaine and benzoylecgonine in a highly competitive manner, whereas the purified polyclonal antibodies from vaccinated humans and mice, revealed preferential selectivity to pharmacologically active cocaine but not to the inactive metabolite benzoylecgonine.
Ramakrishnan, Abstract, Results.
Therefore, claim 1 was prima facie obvious at the time of filing.
Claim 2 is directed towards the composition of claim 1, wherein the composition is free of EDAC and amidine. One of ordinary skill in the art would have a reasonable expectation of success to generate the composition of claim 1 free of EDAC and amidine because the composition of Scherrmann is free of EDAC and amidine because Scherrmann uses dioxane, tributylamine and isobutylchloroformate to conjugate the hapten to BSA (Scherrmann, Specification, columns 5-6). Therefore, claim 2 was prima facie obvious at the time of filing.
Claim 4 is directed towards the method of claim 1, wherein the average ratio of cocaine-succinyl moieties to BSA is selected from the group consisting of at least 7.5, at least 8.0 and at least 8.2. As shown above, Scherrmann teaches that the ratio of hapten to BSA is 15:1. Therefore, claim 4 was prima facie obvious at the time of filing.
Claim 5 is directed towards a composition of matter comprising a plurality of cocaine-succinyl-BSA wherein (i) the average ratio of cocaine-succinyl moieties to BSA is at least 8.2 and (ii) the composition is free of EDAC and amidine. The rejection of claims 1-2 and 4 is incorporated herein by reference. Therefore, claim 5 was prima facie obvious at the time of filing.
Claim 28 is directed towards a method for making cocaine-succinyl-BSA comprising containing cocaine-succinate with BSA under conditions permitting the formation of cocaine-succinyl-BSA, wherein (i) such conditions comprise the presence of tributylamine, dioxane, and isobutyl chloroformate and (ii) the contacting is performed in the absence of EDAC and amidine, and the average ratio of hapten to BSA is at least 8.2.
One of ordinary skill in the art would have a reasonable expectation of success to make cocaine-succinyl-BSA by reacting cocaine-succinate with BSA in the presence of tributylamine, dioxane, and isobutyl chloroformate because Scherrmann teaches that the terminal carboxylic acid group will react with BSA to form a conjugate in the presence of tributylamine, dioxane, and isobutyl chloroformate:
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Scherrmann, Specification, col. 6.
As shown above, Scherrmann teaches that the ratio of hapten to BSA is 15 (falling within the range of at least 8.2).
Therefore, claim 28 was prima facie obvious at the time of filing.
Claim(s) 1-2, 4-5, 7, 9-12, 28, and 30-33 is/are rejected under 35 U.S.C. 103 as being unpatentable over Scherrmann et al. (US 5,817,770 A, published October 6, 1998) and Ramakrishnan et al. (PLOS One, 7(7): e40518, p. 1-12, published July 10, 2012), as applied to claims 1-2, 4-5 and 28 above, and further in view of Kimishima et al. (ACS Med. Chem. Lett., 2018, 9, 5, p. 411–416, published April 16, 2018).
The rejection of claims 1-2, 4-5 and 28 above is incorporated herein by reference, demonstrating the obviousness of cocaine- succinyl-BSA, wherein the average ratio of cocaine-succinyl moieties to BSA is at least 7.0, free of EDAC and free of any amidine.
Claim 7 recites: A composition of matter comprising a plurality of cocaine- succinyl-BSA, wherein (i) the average ratio of cocaine-succinyl moieties to BSA is at least 7.0; (ii) the composition is free of EDAC and free of any amidine; (iii) the cocaine-succinyl-BSA is adsorbed onto a suitable adjuvant; and (iv) the cocaine-succinyl-BSA so adsorbed is suspended in a suitable buffer.
Scherrmann teaches that the hapten-BSA conjugate is “formulated, usually with an adjuvant, such as complete Freund's adjuvant, alum, various complex lipid-sugar membrane oligomers, or the like.” (Scherrmann, Specification, col. 3, lines 32-35). (Alum is aluminum hydroxide).
While Scherrmann does not explicitly teach that the formulation is suspended in a suitable buffer, it is commonly known in the art that cocaine-protein conjugates for vaccination are adsorbed onto aluminum hydroxide and suspended in a suitable buffer such as PBS.
For example, Kimishima teaches: “GNE-TT and GND-TT immunoconjugates in PBS pH 7.4 (48 µL, 1.2 mg/mL) were formulated with alum (Alhydrogel®, Invivogen, 100 µL, 10 mg/mL) and CpG ODN 1826 (Eurofins MWG Operon, 5 µL, 10 mg/mL). All vaccine injections were conducted intraperitoneally (150-200 µL) on days 0, 14, 28, 66 and 88.” (Kimishima, S3).
Therefore, claim 7 was prima facie obvious at the time of filing.
Claim 9 is directed towards the composition of claim 7, wherein the average ratio of cocaine-succinyl moieties to BSA is selected from the group consisting of at least at least 7.5, at least 8.0, and at least 8.2. As shown above in the rejection of claim 1, Scherrmann teaches a ratio of 15. Therefore, claim 9 was prima facie obvious at the time of filing.
Claim 10 is directed towards the composition of claim 7, wherein the adjuvant is aluminum hydroxide gel. As shown in the rejection of claim 7, Scherrmann teaches alum and Kimishima teaches alum (Alhydrogel®). Therefore, claim 10 was prima facie obvious at the time of filing.
Claim 11 is directed towards the composition of claim 7, wherein the suitable buffer is PBS. As shown in the rejection of claim 7, Kimishima teaches PBS. Therefore, claim 11 was prima facie obvious at the time of filing.
Claim 12 is directed towards the composition of claim 7, wherein (i) the average ratio of cocaine-succinyl moieties to BSA is at least 8.2; (ii) the composition is free of EDAC and free of any amidine; (iii) the cocaine-succinyl-BSA is adsorbed onto aluminum hydroxide gel; and (iv) the cocaine-succinyl-BSA so adsorbed is suspended in phosphate buffered saline. The rejection of claims 7 and 9-11 is incorporated herein by reference which addresses each of these limitations. Therefore, claim 12 was prima facie obvious at the time of filing.
Claims 30-31 are directed towards an article of manufacture comprising the composition of claim 7 or 12 respectively, and a label indicating a use in treating a human subject addicted to cocaine. Claims 32-33 are directed towards an article of manufacture comprising the composition of claim 7 or 12 respectively, and a label indicating a use in preventing cocaine addiction. One of ordinary skill in the art would have a reasonable expectation of success to apply the compositions of claims 7 and 12 to the treatment and prevention of cocaine addiction because cocaine conjugates are commonly known in the art for the treatment of cocaine addiction. For example, Scherrmann teaches that the compositions of the invention can be used in the treatment of cocaine addiction and in other applications associated with cocaine (Scherrmann, Specification, col. 1-2). Therefore, claims 30-33 were prima facie obvious at the time of filing.
Claim(s) 1-2, 4-5, 26 and 28 is/are rejected under 35 U.S.C. 103 as being unpatentable over Scherrmann et al. (US 5,817,770 A, published October 6, 1998) and Ramakrishnan et al. (PLOS One, 7(7): e40518, p. 1-12, published July 10, 2012), as applied to claims 1-2, 4-5 and 28 above, and further in view of Asif et al. (American Journal of Pharmacological Sciences, 2014, Vol. 2, No. 1, 1-6, published 2014)
The rejection of claims 1-2, 4-5 and 28 above is incorporated herein by reference, demonstrating the obviousness of cocaine- succinyl-BSA, wherein the average ratio of cocaine-succinyl moieties to BSA is at least 7.0, free of EDAC and free of any amidine. The rejection of claim 28 shows the conjugation reaction of cocaine-succinate and BSA in the presence of tributylamine, dioxane, and isobutyl chloroformate.
Claim 26 recites:
A method for making cocaine-succinyl-BSA, comprising the following steps:
(a) contacting cocaine with succinic anhydride in the presence of benzene under conditions permitting the formation of cocaine-succinate; and
(b) contacting the resulting cocaine-succinate with BSA under conditions permitting the formation of cocaine-succinyl-BSA, wherein (i) such conditions comprise the presence of tributylamine, dioxane, and isobutyl chloroformate, and (ii) neither step (a) nor step (b) is performed in the presence of EDAC or in the presence of any amidine and (iii) in the cocaine-succinyl-BSA so formed, the average ratio of cocaine-succinyl moieties to BSA is at least 8.2.
Claim 26.
As shown in the rejection of claim 26, Scherrmann teaches step (b).
While Scherrmann does not show how to react cocaine with succinic anhydride in the presence of benzene to form cocaine-succinate, one of ordinary skill in the art would have a reasonable expectation of success to react cocaine with succinic anhydride in the presence of benzene to form cocaine-succinate because it is commonly known in art that phenyl groups can be succinated in the presence of benzene to form phenyl-succinate. For example, Asif teaches this reaction:
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Taken anhydrous aluminum chloride (0.15mol) in dry benzene (50ml) under anhydrous conditions and the mixture was refluxed on a water bath. Succinic anhydride (0.10mol) was then added to the reaction mixture in small portions with continuous stirring and heating were continued for 6h. The reaction mixture then was left overnight at room temperature and then added ice cold solution of conc. HCl acid (2.5% v/v) to make acidic mixture [8,9]. The mixture was concentrated to a small volume by heating on a water bath then precipitates were formed and separated by filtration. It was purified by dissolving in 5% w/v sodium bicarbonate solution, followed by extraction with ether. The aqueous layer on acidify with dil. HCl acid gave crude benzoyl-propionic acids.
Asif, p. 2.
The reaction is summarized below:
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CAS Reaction Number: 31-091-CAS-4820204.
Therefore, claim 26 was prima facie obvious at the time of filing.
Claim Rejections – 35 USC § 103 – New Grounds of Rejection Necessitated by Amendment
Claim(s) 1-2, 4-5, 7, 9-12, 28, 30-33 and 103 is/are rejected under 35 U.S.C. 103 as being unpatentable over Scherrmann et al. (US 5,817,770 A, published October 6, 1998) and Ramakrishnan et al. (PLOS One, 7(7): e40518, p. 1-12, published July 10, 2012), as applied to claims 1-2, 4-5 and 28 above, and further in view of Kimishima et al. (ACS Med. Chem. Lett., 2018, 9, 5, p. 411–416, published April 16, 2018).
The rejection of claims 1-2, 4-5, 7, 9-12, 28 and 30-33 under 35 U.S.C. 103 as being unpatentable over Scherrmann et al. (US 5,817,770 A, published October 6, 1998) and Ramakrishnan et al. (PLOS One, 7(7): e40518, p. 1-12, published July 10, 2012) and further in view of Kimishima et al. (ACS Med. Chem. Lett., 2018, 9, 5, p. 411–416, published April 16, 2018) is incorporated herein by reference.
Claim 103 is directed towards the composition of claim 12, wherein the average ratio of cocaine-succinyl moieties to BSA is 8.2-8.3.
One of ordinary skill in the art would have a reasonable expectation of success to conjugate 8.2-8.3 cocaine-succinyl moieties to BSA because similar ratios are commonly known in the art. For example, Scherrmann teaches a ratio of 15 hapten moieties to BSA as shown in the rejection of claim 1. Ramakrishnan teaches that the ratio of hapten moeities per BSA is 7 (Ramakrishnan, p. 7, Table 2). A prima facie case of obviousness exists when ranges or amounts overlap or lie inside the ranges known in the prior art or are merely close (MPEP § 2144.05(I)). Furthermore, “[g]enerally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical.” (MPEP § 2144.05(II)). The claimed range of 8.2-8.3 falls within the range of between 7 and 15 known in the prior art. The Applicant has not demonstrated that the claimed range of 8.2-8.3 is critical for the outcome.
Therefore, claim 103 was prima facie obvious at the time of filing.
Given the above teachings, the invention as a whole was prima facie obvious at the time of filing.
Conclusion
No claim is found to be allowable.
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 extension fee 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 date of this final action.
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/HEATHER DAHLIN/Examiner, Art Unit 1629
/JEFFREY S LUNDGREN/Supervisory Patent Examiner, Art Unit 1629
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