DETAILED ACTION
Notice of Pre-AIA or AIA Status
This Office action details a first action on the merits for the above referenced application No. Claims 1-15 are pending in this application. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 02/26/2024 was noted and the submission 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 were received on 02/26/2026. These drawings are acknowledged.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 5, 7-9, 12 and 14 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Regarding claims 5, 7-9, 12 and 14 the phrase “particularly” renders the claims indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. Thus, the claim and claims which depend from its which don not rectify the issue are considered indefinite.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-4, 7 and 9-15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Aime et al. (US 10,695,448).
Aime discloses a process for the preparation of aqueous solutions of [1-13C]-hyperpolarized carboxylate containing molecules of diagnostic interest that comprises parahydrogenating with molecular parahydrogen unsaturated alkenyl or alkynyl esters of the concerned 13C- carboxylate molecules using the Para Hydrogen Induced Polarization (PHIP) technique (abstract and Col.1 line 17-24). In one embodiment, the PHIP process for the preparation of [1-13C]-hyperpolarized carboxylate containing molecules (pyruvate) for use in MR diagnostic applications that comprises the steps of: a) obtaining an unsaturated alkenyl or alkynyl ester of the carboxylate containing molecule of interest and reacting the unsaturated ester with molecular para-hydrogen, to give the corresponding parahydrogenated ester; b) inducing a polarization transfer from added polarized H to the 13C-signal of the [1-13C]-carboxylate carbon atom to give the corresponding [1-13C]-hyperpolarized carboxylate ester; c) removing the hydrogenated ester moiety and collecting an aqueous solution of the [1-13C]-hyperpolarized carboxylate containing molecule, or of the corresponding [1-13C]-hyperpolarized carboxylic acid (Col. 4 line 50-65). In one embodiment, discloses that process according to the invention comprising carrying out the 13C polarization of the precursor ester molecule in an aqueous medium preferably includes an additional step d) comprising removing hydrogenation catalyst and optional organic co-solvent(s) from the aqueous solution of the [1-13C]-hyperpolarized carboxylate compound obtained at step c), thereby obtaining an aqueous solution of [1-13C]-hyperpolarized carboxylate containing molecule of interest suitable for use in in vivo applications is achieved by quick evaporation of the aqueous solution of the hyperpolarized product, for instance by spraying the solution into a chamber or flask connected to a vacuum pump. The removal of the potentially toxic Rh(I) complex may then be conveniently performed, e.g., by elution of the aqueous solution (of the hyperpolarized molecule) resulting from removal of any optional organic solvent or co-solvent on a micro-column containing less than 1 ml of a cationic exchange resin, retaining the positively charged hydrogenation catalyst. (Col. 15 line 1-25). In preferred embodiment, unsaturated esters include general formula (II) R-C*(O)-R’ in which C* denotes the naturally 13C enriched or, 13C labeled carboxylate carbon atom undergoing 13C hyperpolarization, R is C1-5 alkyl residue of formula -C1-5, a methyl carbonyl of formula CH3C(O)-, and R’ selected from vinyl (of formula -CH=CH2), allyl (of formula -CH2-CH=CH2) (Col. 11 line 5-15). Examples of catalysts suitable for the use in aqueous solvents include rhodium(I) complexes of formula [Rh(diphosphine)diene)]+ [anion]-(Col. 15 line 57+). In one embodiment, the parahydrogenation reaction of the propargyl-pyruvate was then carried out in an organic medium consenting to benefit from a phase transfer-extraction of the [1-13C]-hyperpolarized pyruvate, allowing to remove the hydrogenation catalyst and to reduce to substantially non-detectable values the amounts of optional alcoholic (or water miscible) co-solvents in the final aqueous mixture, thereby leading to a substantially impurity-free aqueous solution of the desired [1-13C]-hyperpolarized pyruvate (Col. 24 line 8-16). Additional disclosure includes that the process allows to obtain [1-13C]-hyperpolarized carboxylate containing molecules of diagnostic interest that are not directly obtainable with PHIP technique by addition of para-hydrogen to their one unsaturated direct precursor and are thus currently obtained by means of the DNP hyperpolarization technique.
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.
Claim(s) 1-15 are rejected under 35 U.S.C. 103 as being unpatentable over Aime et al. (US 10,695,448) in view of Lucyna Holysz et al., (J Colloidal and Interface Science, 316, 996-1002, 2007) and Quan-wei Yang et al, (Desalination and water Treatment, 216, 299-305, 2021).
Aime discloses a process for the preparation of aqueous solutions of [1-13C]-hyperpolarized carboxylate containing molecules of diagnostic interest that comprises parahydrogenating with molecular parahydrogen unsaturated alkenyl or alkynyl esters of the concerned 13C- carboxylate molecules using the Para Hydrogen Induced Polarization (PHIP) technique (abstract and Col.1 line 17-24). In one embodiment, the PHIP process for the preparation of [1-13C]-hyperpolarized carboxylate containing molecules (pyruvate) for use in MR diagnostic applications that comprises the steps of: a) obtaining an unsaturated alkenyl or alkynyl ester of the carboxylate containing molecule of interest and reacting the unsaturated ester with molecular para-hydrogen, to give the corresponding parahydrogenated ester; b) inducing a polarization transfer from added polarized H to the 13C-signal of the [1-13C]-carboxylate carbon atom to give the corresponding [1-13C]-hyperpolarized carboxylate ester; c) removing the hydrogenated ester moiety and collecting an aqueous solution of the [1-13C]-hyperpolarized carboxylate containing molecule, or of the corresponding [1-13C]-hyperpolarized carboxylic acid (Col. 4 line 50-65). In one embodiment, discloses that process according to the invention comprising carrying out the 13C polarization of the precursor ester molecule in an aqueous medium preferably includes an additional step d) comprising removing hydrogenation catalyst and optional organic co-solvent(s) from the aqueous solution of the [1-13C]-hyperpolarized carboxylate compound obtained at step c), thereby obtaining an aqueous solution of [1-13C]-hyperpolarized carboxylate containing molecule of interest suitable for use in in vivo applications is achieved by quick evaporation of the aqueous solution of the hyperpolarized product, for instance by spraying the solution into a chamber or flask connected to a vacuum pump. The removal of the potentially toxic Rh(I) complex may then be conveniently performed, e.g., by elution of the aqueous solution (of the hyperpolarized molecule) resulting from removal of any optional organic solvent or co-solvent on a micro-column containing less than 1 ml of a cationic exchange resin, retaining the positively charged hydrogenation catalyst. (Col. 15 line 1-25). In preferred embodiment, unsaturated esters include general formula (II) R-C*(O)-R’ in which C* denotes the naturally 13C enriched or, 13C labeled carboxylate carbon atom undergoing 13C hyperpolarization, R is C1-5 alkyl residue of formula -C1-5, a methyl carbonyl of formula CH3C(O)-, and R’ selected from vinyl (of formula -CH=CH2), allyl (of formula -CH2-CH=CH2) (Col. 11 line 5-15). Examples of catalysts suitable for the use in aqueous solvents include rhodium(I) complexes of formula [Rh(diphosphine)diene)]+ [anion]-(Col. 15 line 57+). In one embodiment, the parahydrogenation reaction of the propargyl-pyruvate was then carried out in an organic medium consenting to benefit from a phase transfer-extraction of the [1-13C]-hyperpolarized pyruvate, allowing to remove the hydrogenation catalyst and to reduce to substantially non-detectable values the amounts of optional alcoholic (or water miscible) co-solvents in the final aqueous mixture, thereby leading to a substantially impurity-free aqueous solution of the desired [1-13C]-hyperpolarized pyruvate (Col. 24 line 8-16). Additional disclosure includes that the process allows to obtain [1-13C]-hyperpolarized carboxylate containing molecules of diagnostic interest that are not directly obtainable with PHIP technique by addition of para-hydrogen to their one unsaturated direct precursor and are thus currently obtained by means of the DNP hyperpolarization technique.
Aime fails to disclose the evaporation step is performed in a static magnetic field.
Lucyna Holysz discloses a study to investigate the effects of a relatively weak static magnetic field (15mT), originating from a stack of magnets, could influence conductivity and the evaporation of water from aqueous solutions of selected inorganic electrolytes. Water and electrolytes solutions were exposed for 5 min to a relatively weak static magnetic field (15mT), and their conductivity and the amount of evaporated water were then measured as a function of time (abstract). Simultaneously, these quantities were determined for magnetically untreated samples, as reference systems. In Fig. 2B, the changes in evaporated amounts are depicted for magnetic field (MF) treated and untreated water samples. A clear visible trend is observed that evaporated amounts are higher for MF-treated samples and the differences are practically constant during the 37 minutes of the experiments. During the same time, the amounts of evaporated water from the electrolyte solutions (Fig. 4A). These results clearly show that evaporation of water from the solutions depends on the water-ordering or disordering role of the cations and anions present (page 998) and are proportional to the thickness of the hydration shell around the ions and thermodynamic functions of hydration.
Quan-wei Yang discloses study showing the potential of enhancing water evaporation by combining dynamic and static magnetic treatment of magnetic field. Water was firstly treated by dynamic treatment and then the treated water was exposed to the static magnetic field and its evaporation amount was measured. Results show that the combination of dynamic and static magnetic field treatment generates a synergistic effect and significantly improves the water evaporation, and maximum enhancement of 14.3% is obtained (abstract). This study presents an effective and economical approach to improve water evaporation rate with simple operation and low energy consumption, and contributes to the high efficiency in applications involves water evaporation.
It would have been obvious to one of ordinary skill in the art at the time the invention was made to incorporate the step of static magnetic field in the evaporation of liquids into Aime’s process for the preparation of aqueous solutions of [1-13C]-hyperpolarized carboxylate containing molecules of diagnostic interest. The person of ordinary skill in the art would have been motivated to make those modifications because Yang teaches that the combination of dynamic and static magnetic field treatment generates a synergistic effect and significantly improves the water evaporation, and maximum enhancement of 14.3% is obtained (abstract) and reasonably would have expected success because combination of dynamic and static magnetic field treatment method is characterized as simple operation, low cost, and environmental friendliness, and further improves the production efficiency involving water evaporation. This method can be easily implemented in practical engineering and provide a new and effective pretreatment approach for improving water evaporation rate.
Conclusion
No claims are allowed at this time.
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/J.R.S/ Examiner, Art Unit 1618
/Michael G. Hartley/ Supervisory Patent Examiner, Art Unit 1618
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