DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Election/Restriction
REQUIREMENT FOR UNITY OF INVENTION
As provided in 37 CFR 1.475(a), a national stage application shall relate to one invention only or to a group of inventions so linked as to form a single general inventive concept (“requirement of unity of invention”). Where a group of inventions is claimed in a national stage application, the requirement of unity of invention shall be fulfilled only when there is a technical relationship among those inventions involving one or more of the same or corresponding special technical features. The expression “special technical features” shall mean those technical features that define a contribution which each of the claimed inventions, considered as a whole, makes over the prior art.
The determination whether a group of inventions is so linked as to form a single general inventive concept shall be made without regard to whether the inventions are claimed in separate claims or as alternatives within a single claim. See 37 CFR 1.475(e).
When Claims Are Directed to Multiple Categories of Inventions:
As provided in 37 CFR 1.475 (b), a national stage application containing claims to different categories of invention will be considered to have unity of invention if the claims are drawn only to one of the following combinations of categories:
(1) A product and a process specially adapted for the manufacture of said product; or
(2) A product and a process of use of said product; or
(3) A product, a process specially adapted for the manufacture of the said product, and a use of the said product; or
(4) A process and an apparatus or means specifically designed for carrying out the said process; or
(5) A product, a process specially adapted for the manufacture of the said product, and an apparatus or means specifically designed for carrying out the said process.
Otherwise, unity of invention might not be present. See 37 CFR 1.475 (c).
Restriction is required under 35 U.S.C. 121 and 372.
This application contains the following inventions or groups of inventions which are not so linked as to form a single general inventive concept under PCT Rule 13.1.
In accordance with 37 CFR 1.499, applicant is required, in reply to this action, to elect a single invention to which the claims must be restricted.
Group I, claim(s) 1-5, 7, 9, 11-13, 15-19, 24, 25, 27, drawn to an analytical method.
Group II, claim(s) 31, drawn to a kit.
The groups of inventions listed above do not relate to a single general inventive concept under PCT Rule 13.1 because, under PCT Rule 13.2, they lack the same or corresponding special technical features for the following reasons:
Groups I-II lack unity of invention because even though the inventions of these groups require the technical feature of a solution comprising a chromophore probe, this technical feature is not a special technical feature as it does not make a contribution over the prior art in view of Nieto et al. "Rapid Enantiomeric Excess and Concentration Determination Using Simple Racemic Metal Complexes" Organic Letters. 21 October 2008, as noted in the International Search Report and the Written Opinion of the International Searching Authority, filed 02/09/2024. Accordingly, these groups lack a common special technical feature that makes a contribution over the cited prior art and therefore lack unity of invention.
During a telephone conversation with Attorney of Record Anna V. Gromova on 06/17/2026 a provisional election was made without traverse to prosecute the invention of Group I, claims 1-5, 7, 9, 11-13, 15-19, 24, 25 and 27. Affirmation of this election must be made by applicant in replying to this Office action. Claim 31 is withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to a non-elected invention.
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 1-5, 7, 9, 11-13, 15-19, 24, 25 and 27 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.
Claims 1-3, 7, 9, 24 & 25 are not clear with respect to what applicant is claiming. The claims do not clearly set forth the metes and bounds of the patent protection desired.
Regarding claim 1, the phrase “potentially” renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. Furthermore, the claim is unclear reciting “a sample potentially containing a chiral analyte that can exist in stereoisomeric forms; [...] said contacting is carried out under conditions to permit binding of the chromophore probe to the chiral analyte, if present in the sample, to form a probe-labeled analyte” because the limitation appears to be a descriptive statement defining the result to be achieved, without providing any steps involved in the method. Claims 2, 3, 24 and 25 are similarly unclear. Regarding claims 7 & 9, the phrase “optionally” renders the claims indefinite because the claims include optional elements, which make the scope of the claim unascertainable. A claim is indefinite where it merely recites a use without any active, positive steps delimiting how this use is actually practiced.
Claim 19 is unclear reciting “about 1 to about 300 minutes” because the unit for ‘1’ is not specified.
Claim Rejections - 35 USC § 102
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 (i.e., changing from AIA to pre-AIA ) 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 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, 12 & 13 is/are rejected under 35 U.S.C. 102a1 as being anticipated by “Nieto” (Nieto et al., Rapid Enantiomeric Excess and Concentration Determination Using Simple Racemic Metal Complexes, Organic Letters 2008 10 (22), 5167-5170).
Regarding claim 1, Nieto teaches:
1. An analytical method (pg. 5167, abstract) comprising:
providing a sample containing a chiral analyte (pg. 5168, Figure 1A);
contacting the sample with a chromophore probe (pg. 5168, Figure 1B; pg. 5169, left col, ¶ 1),
wherein said contacting is carried out under conditions to permit binding of the chromophore probe to the chiral analyte (pg. 5168, left col, ¶ 3: addition of the chiral guests to the receptors; pg. 5168, right col, ¶ 1), to form a probe-labeled analyte (pg. 5168, left col, ¶ 3); and
detecting the probe-labeled analyte in the sample using a single chiroptical assay format (pg. 5168, right col, ¶ 1: CD spectrum), and determining the concentration of the analyte in the sample and one or both of (i) the absolute configuration of the analyte in the sample, and (ii) the enantiomeric and/or the diastereomeric composition of the analyte in the sample (pg. 5170, right col, ¶ 1: The technique allows for the determination of both concentration and ee values in under 2 min per sample; pg. 5170. Table 1).
With regard to limitations in claims 1, 2, 3, 7, 9, 24, 25 (e.g., a sample potentially containing a chiral analyte that can exist in stereoisomeric forms; [...] said contacting is carried out under conditions to permit binding of the chromophore probe to the chiral analyte, if present in the sample, to form a probe-labeled analyte [...]; the chromophore probe [...] binds the chiral analyte to form the probe-labeled analyte [...], etc.), these claim limitations do not specify active method steps, which do not further delineate the claimed method from that of the prior art. It has been held that to be entitled to weight in method claims, the recited structure limitations therein must affect the method in a manipulative sense, and not to amount to the mere claiming of a use of a particular structure.
Regarding claims 4, 12, 13, Nieto teaches:
4. The analytical method according to claim 1, wherein the chromophore probe is a metal salt, a quinone, a (hetero)aryl isocyanate, a (hetero)aryl isothiocyanate, a phenyl-naphthalene compound, an aryl halophosphite, an aryl halodiazaphosphite, a coumarin-derived Michael acceptor, a dinitrofluoroarene, an arylchlorophosphine, a metal complexed ligand, and a (hetero)arenesulfonyl compound (pg. 5168, Figure 1B).
12. The analytical method according to claim 1, wherein the chiroptical assay format is circular dichroism (CD), vibrational CD (VCD), electronic CD, optical rotatory dispersion (ORD), or polarimetry (pg. 5168, right col, ¶ 1: CD spectrum).
13. The analytical method according to claim 1, wherein the chiral analyte and the corresponding probe are selected from the group consisting of:
Probe
Chiral Analyte
Metal salts
amino acids, a-hydroxy acids, aminophosphonic acids, amino alcohols, and amines;
Substituted phenyl-naphthalene
monoamines, amino alcohols, amino acids, and combinations thereof;
aryl halophosphite
primary amines, secondary amines, aminoalcohols, alcohols, hydroxy acids, amino acids, and combinations thereof;
halodiazaphosphite
primary amines, secondary amines, aminoalcohols, alcohols, hydroxy acids, amino acids, and combinations thereof;
coumarin-derived Michael acceptor
primary amines, secondary amines, amino alcohols, alcohols, hydroxy acids, amino acids, and combinations thereof;
dinitrofluoroarene
primary amines, secondary amines, aminoalcohols, alcohols, hydroxy acids, amino acids, and combinations thereof;
arylchlorophosphine
primary amines, secondary amines, aminoalcohols, alcohols, hydroxy acids, amino acids, and combinations thereof;
an achiral quinone
amines, amino acids, amino alcohols, and combinations thereof;
(hetero)aryl isocyanate
amines, amino acids, amino alcohols, diols, alcohols, and combinations thereof;
(hetero)aryl isothiocyanate
amines, amino acids, amino alcohols, diols, alcohols, and combinations thereof;
(hetero)arenesulfonyl compound
primary amines, secondary amines, amino alcohols, amino acids, and combinations thereof;
Metal complexed ligands
amines, diamines, a-hydroxy acids, amino acids, and amino alcohols (pg. 5168, Figure 1A-B).
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.
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.
Claim(s) 5, 7, 9, 11, 15-19, 24, 25, 27 is/are rejected under 35 U.S.C. 103 as being unpatentable over “Nieto” (Nieto et al., Rapid Enantiomeric Excess and Concentration Determination Using Simple Racemic Metal Complexes, Organic Letters 2008 10 (22), 5167-5170) in view of “Wolf” (Wolf et al., WO 2020/028396 A1).
Regarding claim 5, Nieto does not explicitly teach: 5. The analytical method according to claim 4, wherein the chromophore probe is an achiral (hetero)arenesulfonyl compound having the structure according to formula (I): Ar-SO2-Z (I), wherein Ar is a substituted or unsubstituted aromatic or heteroaromatic chromophore, and Z is a leaving group.
Wolf teaches a similar method comprising CD analysis to determine concentration and ee (abstract) wherein the chromophore probe is an achiral (hetero)arenesulfonyl compound having the structure according to formula (I): Ar-SO2-Z; wherein Ar is a substituted aromatic chromophore, and Z is a leaving group (¶ 0199). It would have been obvious to one of ordinary skill in the art at the time the invention was made to utilize the method disclosed by Nieto; further comprising various chromophore probes utilized in similar methods, as disclosed by Wolf; which produce CD data.
Regarding claim 7, modified Nieto teaches: 7. The analytical method according to claim 5, wherein the probe is an achiral (hetero)arenesulfonyl compound of Formula Ia:
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389
606
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wherein: each X is independently C or N, except that no more than three ring nitrogens are present in the (hetero)arenesulfonyl compound, and R1, R2, R3, R4, and R5are independently selected from the group consisting of a lone pair (when X is N), -H, -CN, -NO2, halogen, -C1-C6alkyl, -C1-C6alkoxy, -N-(alkyl)2, -C1-C6alkenyl, -C1-C6alkynyl, -C1-C6perfluoroalkyl, -aryl, -perfluoroaryl, -aryloxy, -N-(aryl)2, -heteroaryl, -O-heteroaryl, -N-(heteroaryl)2, -cycloalkyl, -O-cycloalkyl, -N-(cycloalkyl)2, -heterocycloalkyl, -O-heterocycloalkyl, -N-(heterocycloalkyl)2, -C(O)Ra, -SO2Ra, and -OC(O)Ra; each Ra is independently selected from the group consisting of -alkyl, -O-alkyl, -N-(alkyl)2, -alkenyl, -alkynyl, -aryl, -O-aryl, -N-(aryl)2, -heteroaryl, -O-heteroaryl, -N-(heteroaryl)2, -cycloalkyl, -O-cycloalkyl, -N-(cycloalkyl)2, -heterocycloalkyl, -O-heterocycloalkyl, and -N-(heterocycloalkyl)2; and wherein, optionally, R1 and R2, R2 and R3, R3 and R4, and/or R4 and R5 are alternatively taken together with the carbon or nitrogen atoms to which they are attached to form a fused monocyclic or bicyclic ring system selected from the group consisting of cycloalkyl, heterocycloalkyl, aryl, and heteroaryl, wherein the fused ring system is optionally substituted with one or more groups selected from -alkyl, -O-alkyl, -N-(alkyl)2, -alkenyl, -alkynyl, -O-aryl, -O-heteroaryl, -N-(aryl)2, -N-(heteroaryl)2, -aryl, -C(O)Rc, -CO2Rb, -O-C(O)Rb, -NHC(O)Rb, -NRcC(O)Rb, -NO2, -CN, -halogen, and -SO2Rb, wherein each Rbis independently Ar, alkyl, or CH2Ar and Ar is an aryl or heteroaryl (Wolf ¶ 0199).
Regarding claim 9, modified Nieto teaches general formulas for the chromophore comprising a heteroaryl sulfonyl chloride (¶ 0197: Formula III R2 is an aryl or heteroaryl) and further teaches various heteroaryls such as pyrrole (¶ 0213: pyrrolyl), but does not teach wherein the probe is an achiral (hetero)arenesulfonyl compound according to Formula 1b:
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345
612
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. However, it would have been obvious to one with skill in the art to utilize the method disclosed comprising various chromophore compounds of the general formula disclosed; such as wherein R2 is a pyrrole; i.e., wherein X is C or N and R1, R2, R3 and R4 are H; through routine experimentation.
Regarding claim 11, modified Nieto teaches: 11. The analytical method according to claim 5, wherein the probe is selected from:
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1279
882
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(Wolf ¶ 0199).
Regarding claims 15-19, 24, 25, 27, modified Nieto teaches:
15. The analytical method according to claim 1, wherein said contacting is carried out in a solvent selected from chloroform, dichloromethane, acetonitrile, toluene, tetrahydrofuran, methanol, ethanol, isopropanol, water, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), pentane, pentane isomers, hexane, hexane isomers, ether, dichloroethane, acetone, ethyl acetate, butanone, and mixtures of any combination thereof (Wolf claim 19, ¶ 0013).
16. The analytical method according to claim 1, wherein said contacting is carried out in an aqueous environment (Wolf claim 21, ¶ 0232).
17. The analytical method according to claim 1, wherein said contacting is carried out in the presence of a base (Wolf ¶ 0232).
18. The analytical method according to claim 1, wherein said contacting is carried out in the presence of a buffer (Wolf ¶ 0349-0350+).
19. The analytical method according to claim 1, wherein said contacting is carried out for about 1 to about 300 minutes (Wolf claim 22).
24. The analytical method according to claim 1, wherein the absolute configuration of the analyte in the sample is determined (Wolf ¶ 0357).
25. The analytical method according to claim 1, wherein the enantiomeric and/or diastereomeric composition of the analyte in the sample is determined (Wolf ¶ 0220, claim 1).
27. The analytical method according to claim 1, wherein said contacting the sample is carried out on at least three measurements to which different known concentrations of the chromophore probe are introduced, wherein one of the at least three measurements comprises an excess concentration of the chromophore probe; and said determining comprises plotting recorded intensity measurements from the chiroptical assay (y-axis) versus the chromophore probe concentration (X-axis) for the at least three measurements, and analyzing the plotted data using linear regression analysis (Wolf ¶ 0278, 0358-0362+).
It would have been obvious to one of ordinary skill in the art at the time the invention was made to incorporate the teachings of Wolf with Nieto, for the purpose of simultaneous ee and concentration determination.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEAN KWAK whose telephone number is (571)270-7072. The examiner can normally be reached M-TH, 4:30 am - 2:30 pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, CHARLES CAPOZZI can be reached at (571)270-3638. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DEAN KWAK/Primary Examiner, Art Unit 1798
DEAN KWAK
Primary Examiner
Art Unit 1798
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