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/Restrictions
Applicant’s election without traverse of Group I, claims 1-10 and 14, and the species of (A) hydrazide as recited on claim 41 in the reply filed on 22 July 2026 is acknowledged.
Claims 11 and 13 withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Abstract
Applicant is reminded of the proper content of an abstract of the disclosure.
In chemical patent abstracts for compounds or compositions, the general nature of the compound or composition should be given as well as its use, e.g., “The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics.” Exemplification of a species could be illustrative of members of the class. For processes, the type of reaction, reagents and process conditions should be stated, generally illustrated by a single example unless variations are necessary.
Applicant is reminded of the proper language and format for an abstract of the disclosure.
The abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details.
The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, “The disclosure concerns,” “The disclosure defined by this invention,” “The disclosure describes,” etc. In addition, the form and legal phraseology often used in patent claims, such as “means” and “said,” should be avoided.
The abstract of the disclosure is objected to because it has fewer than 50 words and uses the legal phraseology "said." A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
Specification
The disclosure is objected to because of the following informalities: As a result of the amendment to the specification on 11/21/2022, the last three lines of the specification (page 97) are redundant.
Appropriate correction is required.
Claim Objections
Claims 1, 5, 7, and 14 are objected to because of the following informalities:
Regarding claim 1 and 14, the limitation "…B1, B2, B3, B4, B5" must be changed to "…B1, B2, B3, B4, and B5".
Regarding claim 1 and 14, the limitation "wherein in case of A3 is ammonium" is grammatically incorrect. Possible corrections include "wherein in the case of A3 being ammonium" or "wherein in the case that A3 is ammonium."
Regarding claim 1, 5, and 14, the limitation "wherein Q" must be changed to "wherein the coupling group Q".
Regarding claim 1 and 14, the limitation "O, N, S, Br" must be changed to "O, N, S, and Br".
Regarding claim 1 and 14 recite the following limitation: "wherein the coupling group Q comprises a C atom, which is separated by four single or double bonds from the C atom of the CA1A2A3 substituent and the coupling group Q comprises a C atom, which is separated by five single or double bonds from the C atom of the CA1A2A3 substituent." Under the assumption that the two listed limitations of "a C atom" are distinct concepts, the following amendment must be made:
wherein the coupling group Q comprises a C atom that [[, which]] is separated by four single or double bonds from the C atom of the CA1A2A3 substituent, and the coupling group Q comprises a C atom that [[, which]] is separated by five single or double bonds from the C atom of the CA1A2A3 substituent.
Regarding claim 7, the word "and" must be added before "R6" and before "short chain alkyl."
Regarding claim 14, as there appears to be no difference between formula I and formula V, the same number should be used for both.
Appropriate correction is required.
Claim Interpretation
Claims 1 and 14 recite the limitation "wherein [the coupling group] Q is free of at least one atom, which is selected from O, N, S, [and] Br." This limitation is interpreted to mean that the coupling group Q does not comprise all of O, N, S, and Br.
Claims 1 and 14 recite the limitation "wherein in case of A3 is ammonium, B1 or B5 is the coupling group Q…" This is interpreted as "wherein in the case of A3 being ammonium, then B1 or B5 is the coupling group Q…" or "wherein in the case that A3 is ammonium, then B1 or B5 is the coupling group Q…" It is noted that the claimed limitation is different from the language described in the specification ("in case of A3 is ammonium and B1 or B5 is the coupling group Q, …") on pages 7-9. In the language discussed in the specification, B1 or B5 being the coupling group Q is part of the conditional, rather than a result of the conditional as claimed. Furthermore, it is noted that this limitation of claim 1 and 14 is narrower than the previously recited choice of A3 comprising ammonium.
Claims 1 and 14 recite the limitation "the C atom of the CA1A2A3 substituent." The specification sets forth the following special definition ([0039] of published application):
The term “C atom of the CA1A2A3 substituent” represents that the C atom to which the substituents A1, A2 and A3 are attached. In other words the “C” in the term “CA1A2A3 substituent” represents the C atom to which A1, A2 and A3 are attached.
Claim 8 recites the limitation "wherein the compound is permanent positively charged." The specification sets forth the following special definition (page 12):
The term “permanent positively charged” is used in the context of the present disclosure that the positive charge of the pyridinium or ammonium or phosphonium unit is not readily reversible, for example, via flushing, dilution, filtration, and the like. A permanent positive charge may be the result, for example, of covalent bonding. A permanent positive charge is in contrast to a reversible positive charge (a non-permanent positive charge) that may be the result, for example, of an electrostatic interaction.
Claim 7 recites the limitation "short chain alkyl." The specification teaches that "In particular, short chain alkyl comprises one, two, three, four, five or six C-atoms in the alkyl chain" ([0172] of published application).
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.
Claims 1-10 and 14 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 1 recites the limitation "the other substituents A1, A2, B1, B2, B3, B4, B5." The limitation "the other substituents … B1, B2, B3, B4, B5" has antecedent basis in the limitation "wherein one of the substituents B1, B2, B3, B4, B5 is a coupling group Q," where the limitation "the other substituents … B1, B2, B3, B4, B5" is interpreted to mean those four of B1, B2, B3, B4, and B5 that are not the previously recited one of the substituents B1, B2, B3, B4, and B5 that is a coupling group Q. However, the limitation "the other substituents A1, A2…" lacks sufficient antecedent basis. Claim 14 is indefinite for analogous reasons.
Claims 1, 7, and 14 recite the term "modified alkyl." The phrase "modified alkyl" is not a term of art, and the scope of a "modified alkyl" substituent is unclear. The specification teaches that "Modified alkyl comprises the structural unit alkyl-O-alkyl, e g. —CH2—O—CH3, —CH2—O—CH2-CH3" ([0081] of published application; added italics). This teaching is interpreted as providing an example of a modified alkyl rather than being a special definition that limits the scope of modified alkyl to the structural unit alkyl-O-alkyl. Accordingly, in the absence of a special definition, the scope of this term is uncertain.
Claim 1 recites the limitation "the other substituents A1, A2, B1, B2, B3, B4, [and] B5 are each independently selected from hydrogen, halogen, … amino, sulfur, isotope or derivative thereof." The term "isotope" is not grammatically correct and its meaning is unclear. Is the intended meaning "an isotope"? In other words, an isotope of any element, not just sulfur? [Such a term would encompass any atom of an element that exists as isotopes. For example, 1H.] Claim 14 is indefinite for analogous reasons.
Claim 1 recites the limitation "the other substituents A1, A2, B1, B2, B3, B4, [and] B5 are each independently selected from hydrogen, halogen, …nitro,… amino, sulfur, isotope or derivative thereof." The term "or derivative thereof" is not grammatically correct (or a derivative thereof?). The scope of a derivative of an isotope is unclear. Would the broadest reasonable interpretation of this limitation encompass any group that contains any atom of an element that exists as isotopes? For example, could any group that comprises 12C could be broadly interpreted as a derivative of an isotope? It is also unclear what the term "thereof" modifies. Does "thereof" modify only the preceding term "isotope" or every term listed from "hydrogen" to "isotope"? If so, the scope of some of the modified terms is unclear. For example, what is a derivative of a nitro group? What is a derivative of hydrogen? Claim 14 is indefinite for analogous reasons.
Claim 1 recites the limitation "wherein A3 comprises ammonium, pyridinium, phosphonium or derivatives thereof. It is unclear what the term "thereof" modifies. Does "thereof" modify only the preceding term "phosphonium" or every term from "ammonium" to "phosphonium"? The meaning of derivatives of ammonium or phosphonium is unclear. The specification provides the following guidance ([0098] and [0100] of published application):
In embodiments of the first aspect of the present invention, ammonium or derivatives thereof is -NR1R2R3, wherein R1, R2, R3 can independently be alkyl or aryl.
[…]
In embodiments of the first aspect of the present invention, phosphonium or derivatives thereof is -PR1R2R3, wherein R1, R2, R3 can independently be alkyl or aryl.
The above teaching of the specification does not clarify how a derivative of an ammonium group is distinct from an ammonium group itself, or how a derivative of a phosphonium group is distinct from a phosphonium group itself. Claim 14 is indefinite for analogous reasons.
Claim 1 recites the limitation "wherein in case of A3 is ammonium, … wherein the coupling group Q comprises a C atom, which is separated by four single or double bonds from the C atom of the CA1A2A3 substituent and the coupling group Q comprises a C atom, which is separated by five single or double bonds from the C atom of the CA1A2A3 substituent." Given the formatting and grammar of the claim, it is unclear whether the two "wherein the coupling group Q comprises a C atom" limitations are part of the conditional limitation of A3 being ammonium. For purposes of applying prior art, these limitations are interpreted as being conditional on A3 being ammonium.
Claim 1 recites the limitation "four single or double bonds." It is unclear whether this limitation means (i) "four single bonds or four double bonds" or (ii) "four bonds, wherein each of the four bonds is independently a single bond or a double bond." The second interpretation (ii) is applied henceforth in this office action. Claim 1 recites the limitation "five single or double bonds," which is indefinite for analogous reasons. Claim 14 is indefinite for analogous reasons.
Dependent claims 2-10 are rejected for depending from claim 1.
Regarding claim 4, which depends from claim 2, it is unclear how the choice of K being Br satisfies the requirement that K is "capable of forming the covalent bond with the analyte." In the case of n being 1, 2, 3, 4 or 5, a nucleophilic analyte would be capable of forming a covalent bond with the terminal methylene carbon of Q. This is different from the bromide leaving group itself forming the covalent bond. Moreover, for choice of K being Br when n is 0, it is unclear how any covalent bond could be formed between coupling group Q and an analyte.
Claim 5 recites the limitation "wherein [the coupling group] Q is selected from the group consisting of methyl hydrazide, methyl hydrazine, methyl hydroxylamine, oxyamine, 4-methyl-oxy-1,2,4-triazolin-3,5-dione (CH2—O—TAD), [a] 2,4-dinitro-5-fluoroaniline derivative, chlorsulfonyl and methanesulfonyl chloride." The intended meaning of "methyl" within these options is unclear. For example, the choice of 4-methyl-oxy-1,2,4-triazolin-3,5-dione is equated to CH2—O—TAD, despite —CH2—O—TAD not comprising a methyl group. The coupling group Q is required to be monovalent, and it is completely unclear how "methanesulfonyl chloride" can be a monovalent group. By the same pattern, it is unclear what the intended meaning of "methyl" is within the options of methyl hydrazide, methyl hydrazine, methyl hydroxylamine. Where applicant acts as his or her own lexicographer to specifically define a term of a claim contrary to its ordinary meaning, the written description must clearly redefine the claim term and set forth the uncommon definition so as to put one reasonably skilled in the art on notice that the applicant intended to so redefine that claim term. Process Control Corp. v. HydReclaim Corp., 190 F.3d 1350, 1357, 52 USPQ2d 1029, 1033 (Fed. Cir. 1999). The term "methyl" in claim 5 is used by the claim within the limitation "4-methyl-oxy-1,2,4-triazolin-3,5-dione (CH2—O—TAD)" to mean “—CH2—,” while the accepted meaning is “—CH3.” The term is indefinite because the specification does not clearly redefine the term.
Regarding claim 5, the scope of a "2,4-dinitro-5-fluoroaniline derivative" is unclear.
Regarding claim 6, it is unclear what is mean by "tributhylammonium."
Claim 7 recites the limitation "wherein A3 is NR1R2R3 or PR4R5R6." Given that A3 is a monovalent group, it is unclear how NR1R2R3 can fail to carry a positive charge on nitrogen (i.e., —N+R1R2R3) or how PR4R5R6 can fail to carry a positive charge on phosphorous (i.e., —P+R4R5R6).
Claim 8 recites the limitation "wherein the compound is permanent positively charged." In view of the special definition of "permanent positively charged" provided by the specification (see claim interpretation section), it is unclear whether this limitation is redundant with the formula provided by claim 8.
Claim 14 recites the limitation "the analyte." There is insufficient antecedent basis for this limitation in the claim.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 8 is rejected under 35 U.S.C. 112(d) as being of improper dependent form for failing to include all the limitations of the claim upon which it depends.
Independent claim 1 recites the following limitation:
wherein in case of A3 is ammonium, B1 or B5 is the coupling group Q, wherein Q is free of at least one atom, which is selected from O, N, S, Br, wherein the coupling group Q comprises a C atom, which is separated by four single or double bonds from the C atom of the CA1A2A3 substituent and the coupling group Q comprises a C atom, which is separated by five single or double bonds from the C atom of the CA1A2A3 substituent.
The formula of dependent claim 8 meets the case that A3 is ammonium but does not satisfy the contingent limitation that B1 or B5 is the coupling group Q. Instead, in the formula of dependent claim 8, B1 and B5 are each hydrogen, and B3 is the coupling group Q. Accordingly, claim 8 fails to include all the limitations of claim 1.
Furthermore, the coupling group Q comprises a C atom (methylene carbon) that is separated by five bonds, wherein each of the five bonds is independently a single bond or a double bond, from the C atom of the CA1A2A3 substituent and a C atom (carbonyl carbon) that is separated by six bonds, wherein each of the six bonds is independently a single bond or a double bond, from the C atom of the CA1A2A3 substituent. The formula of dependent claim 8 meets the case that A3 is ammonium but does not satisfy the contingent limitation that the coupling group Q comprises a C atom that is separated by four single or double bonds from the C atom of the CA1A2A3 substituent (interpreted to mean four bonds, wherein each of the four bonds is independently a single bond or a double bond). Accordingly, claim 8 fails to include all the limitations of claim 1.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claims 1-3, 6, 7, 9, 10, and 14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wang ("Pd@COF-QA: a phase transfer composite catalyst for aqueous Suzuki-Miyaura coupling reaction," Green Chem., 21st January 2020; IDS).
Regarding claims 1 and 14, Wang discloses a compound of formula I or V (L-QA, Scheme 1, annotated below):
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wherein B1 is a coupling group Q, which is capable of forming a covalent bond with the analyte (via hydrazide moiety),
wherein A1, A2, B2, B3, and B5 are each hydrogen and B4 is a derivative of aryl,
wherein given that A3 comprises ammonium, B1 is the coupling group Q, the coupling group Q does not comprise all of O, N, S, and Br (comprising O and N), and the coupling group Q comprises a C atom that is separated by four bonds, wherein each of the four bonds is independently a single bond or a double bond, from the C atom of the CA1A2A3 substituent (see lower arrow of annotation) and the coupling group Q comprises a C atom that is separated by five bonds, wherein each of the five bonds is independently a single bond or a double bond, from the C atom of the CA1A2A3 substituent (see upper arrow of annotation).
Regarding the claim 1 preamble limitation "for mass spectrometric determination of an analyte," it is noted that a preamble is generally not accorded any patentable weight where it merely recites the intended use of a structure, and where the body of the claim does not depend on the preamble for completeness but, instead, the structural limitations are able to stand alone. See In re Hirao, 535 F.2d 67, 190 USPQ 15 (CCPA 1976) and Kropa v. Robie, 187 F.2d 150, 152, 88 USPQ 478, 481 (CCPA 1951). The Courts have held that if the prior art structure is capable of performing the intended use, then it meets the claim. See In re Casey, 152 USPQ 235 (CCPA 1967); and In re Otto, 136 USPQ 458, 459 (CCPA 1963). The Courts have held that it is well settled that the recitation of a new intended use, for an old product, does not make a claim to that old product patentable. See In re Schreiber, 128 F.3d 1473, 1477, 44 USPQ2d 1429, 1431 (Fed. Cir. 1997) (see MPEP § 2114).
Regarding claim 2, Wang discloses that the coupling group Q is bonded to X according to formula II, wherein n is 0 and K is the same as the coupling group Q indicated in the annotation above.
Regarding claims 2 and 3, the reactive unit K of Wang is capable of reactving with a carbonyl group of the analyte and forming the covalent bond with the analyte via the hydrazide moiety.
Regarding claim 6, Wang discloses that A3 is trialkylammonium.
Regarding claim 7, Wang discloses that A3 is N+R1R2R3 and R1, R2, and R3 are methyl and/or alkyl.
Regarding claims 9 and 10, Wang discloses a composition or a kit comprising the compound of claim 1, as set forth above in the rejection of claim 1.
Claims 1-7, 9, 10, and 14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Giese (US 2018/0024123).
Regarding claims 1 and 14, Giese discloses a compound of formula I or V ([0046]-0049], claims 41 and 42),
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wherein one of the substituents B1, B2, B3, B4, B5 is a coupling group Q, which is capable of forming a covalent bond with the analyte ([0048], claim 41),
wherein A1 and A2 ("E is hydrogen or deuterium," [0047], claim 41) and the other substituents B1, B2, B3, B4, B5 are each independently hydrogen ([0048], claim 41),
wherein A3 comprises pyridinium, a derivative of pyridinium, or phosphonium ("pyridinium, fluorine-substituted pyridinium, methoxy-substituted pyridinium, … or triphenylphosphonium group," [0047], claim 41).
The limitations that follow "wherein in case of A3 is ammonium…" are interpreted to be contingent upon A3 being ammonium, which is not the case in the relied upon embodiments of Giese.
Regarding the claim 1 preamble limitation "for mass spectrometric determination of an analyte," it is noted that a preamble is generally not accorded any patentable weight where it merely recites the intended use of a structure, and where the body of the claim does not depend on the preamble for completeness but, instead, the structural limitations are able to stand alone. See In re Hirao, 535 F.2d 67, 190 USPQ 15 (CCPA 1976) and Kropa v. Robie, 187 F.2d 150, 152, 88 USPQ 478, 481 (CCPA 1951). The Courts have held that if the prior art structure is capable of performing the intended use, then it meets the claim. See In re Casey, 152 USPQ 235 (CCPA 1967); and In re Otto, 136 USPQ 458, 459 (CCPA 1963). The Courts have held that it is well settled that the recitation of a new intended use, for an old product, does not make a claim to that old product patentable. See In re Schreiber, 128 F.3d 1473, 1477, 44 USPQ2d 1429, 1431 (Fed. Cir. 1997) (see MPEP § 2114).
Regarding claims 2-4, Giese discloses that the reactivity group is CH2NHNH2 ([0049], claim 42), thereby satisfying the limitations of the claim because n is 1 and K is hydrazide.
Regarding claim 5, for purposes of applying prior art, Giese's disclosure of Q being -CH2NHNH2 ([0049], claim 42) is interpreted as satisfying the indefinite limitation of "methyl hydrazide."
Regarding claim 6, Giese discloses that A3 is pyridinium or phosphonium ([0047], claim 41).
Regarding claim 7, Giese discloses that A3 is P+R4R5R6, wherein R4, R5, R6 are each unsubstituted phenyl (triphenylphosphonium group, ([0047], claim 41).
Regarding claims 9 and 10, Giese discloses a composition or a kit comprising the compound of claim 1, as set forth above in the rejection of claim 1.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MICHELLE ADAMS whose telephone number is (571)270-5043. The examiner can normally be reached M, T, Th, and F, 12-4 P.M.
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/MICHELLE ADAMS/ Examiner, Art Unit 1797
/JENNIFER WECKER/ Primary Examiner, Art Unit 1797
1 Applicant further elects methyl hydrazide as recited in claim 5. However, the species election requirement was directed to the reactive units of claim 4 and not the overall coupling group Q of claim 5.
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