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 .
Priority
This application is a Continuation of PCT International Application No. PCT/JP2022/045206 filed on December 8, 2022, which claims priority under 35 U.S.C §119(a) to Japanese Patent Application No. 2021-199281 filed on December 8, 2021.
Status of Claims
Claims 1-14 are pending and being examined on the merits of this office action.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on September 3, 2024; March 31, 2025; April 7, 2026; and April 20, 2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Specification
The use of the terms ISOLERA (see [0113]), which is a trade name or a mark used in commerce, has been noted in this application. The term should be accompanied by the generic terminology; furthermore the term should be capitalized wherever it appears or, where appropriate, include a proper symbol indicating use in commerce such as ™, SM , or ® following the term.
Although the use of trade names and marks used in commerce (i.e., trademarks, service marks, certification marks, and collective marks) are permissible in patent applications, the proprietary nature of the marks should be respected and every effort made to prevent their use in any manner which might adversely affect their validity as commercial marks.
Appropriate correction is required.
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 1-3, 8, 13 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.
Claim 1 recites a method for producing a peptide compound, comprising: a step of using a substituted benzyl compound represented by Formula (1). The claim attempts to claim a process/method using a compound, without setting forth any steps involved in the process of producing a peptide rendering the claim indefinite. It is noted that while the preamble is drawn to producing a peptide, the body of the claim is completely silent to anything drawn to a peptide or a product produced by “using” Formula (I).
Claims 2, 3, 8, 13, and 14 are dependent on claim 1.
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 4-6 and 7 is 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 4-6 recites “further comprising”. However, claims 4-6 depends upon claim 1 (indirectly), and parent claim 1 is silent about steps. Additionally, the body of parent claim 1 recites limitations listed for the substituted benzyl compound represented by Formula (1), recites “a step of using a substituted benzyl compound represented by Formula (1)”; however it is not specified whether the steps must be performed in a particular order. Therefore, an ordinary skilled artisan would be unable to ascertain the metes and bounds of the claimed invention with regards to determining whether the peptide synthesis scheme yields the compound as recited in the claims 4-6.
Claim 7 recites “further comprising”. However, claim 7 depends upon claim 1, and parent claim 1 is silent about the C-terminal deprotection step. Additionally, the body of parent claim 1 recites limitations listed for the substituted benzyl compound represented by Formula (1), recites “a step of using a substituted benzyl compound represented by Formula (1)”; however it is not specified whether the steps must be performed in a particular order. Therefore, an ordinary skilled artisan would be unable to ascertain the metes and bounds of the claimed invention with regards to determining whether the C-terminal deprotection yields the desired compound as recited in the claim 7.
Claim Rejections - 35 USC § 103
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 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 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over CA 3131772 (published September 3, 2020) in view of US 20070066799 (published March 22, 2007).
CA’772 discloses a method for producing a peptide compound, the method including a step for using a fused polycyclic aromatic hydrocarbon compound represented by formula (1); a protecting group-forming reagent that contains said compound. In formula (1), ring A denotes a fused polycyclic aromatic hydrocarbon ring, YA moieties each independently denote -CH2OH, -CH2NHR, -CH2SH or -CH2X0, R denotes a hydrogen atom, an alkyl group or an aralkyl group, X0 denotes Cl, Br or I, k denotes an integer between 1 and 5, n denotes 1 or 2, and RA moieties each independently denote an aliphatic hydrocarbon group or an organic group having an aliphatic hydrocarbon group (see Abstract).
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Formula (1) (CA’772)
The Formula (1) compound derivative disclosed by CA’772 is similar to the instantly claimed compound. CA’772 also teaches polycyclic aromatic hydrocarbon compound in which the ring A (see formula above) is a naphthalene ring (see [0026]). However, CA’772 does not specifically teach about “A” as substituted benzyl compound.
US’799 teaches method for synthesis of polymer compound such as peptide making utilizing reactive solvent system, and by a compound residue having the function to dissolve the compound (see [0003]). US’799 discloses a method for preparation of peptide utilizing the solvent system for preparation of peptide by liquid phase synthesis comprising, using the combination with carrier induced from the compound possible to improve the solubility to one solvent composing solvent system (see claim 16). US’799 synthesized the compound which is utilized so as the practical use of the solvent system, for example, the compound having a bonding part of amino acid unit from which the formation of peptide in the method for peptide synthesis is initiated with a residue which make the utilization of the solvent system possible such as the compound represented by following general formula A (see [0015]).
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US’799 discloses that in general formula A, L1 is hydroxyl group which bonds with amino acid, a single bond which bonds with thiol group, amino group or carbonyl group, an atomic group which bonds with said hydroxyl group, thiol group, amino group or carbonyl group or an atomic group which forms fused aromatic ring of two rings bonding with dotted line, wherein the dotted line is an atomic group which forms said fused aromatic ring by bonding with H or L1, X is O, S, ester group, sulfide group or imino group, R is hydro carbon group of carbon number 10 or more which can contain O, S or N having a possibility to improve the solubility to cycloalkane solvents as a bonding atom, n is a integer from 1 to 5, further in the case when said hydro carbon group of carbon number 10 or more is to improve the solubility to cycloalkane solvents, R possesses a side chain with functional group which bonds with the amino group and/or substituent (see [0016]).
US’799 also discloses that the method for preparation of the compound , wherein one organic solvent or mixed organic solvent is composed of cycloalkanes and another single organic solvent or mixed organic solvent is composed of at least one selected group consisting of nitroalkane, nitrile, alcohol, halogenated alkyl, amide and sulfoxide (see claim 8); the method for preparation of the peptide by liquid phase synthesis, wherein the carrier consists of aromatic ring moiety and alkyl chains having 10 or more carbons as a fundamental skeleton represented by general formula A which has a functional group for bond amino acid with cycloalkanephilic moiety (see claim 17); the method for preparation of peptide by liquid phase synthesis of claim 16, wherein the compound represented by general formula A is the compound selected from the group of represented by general formulae B wherein, X, R and n are same as to that of general formula A, Q is a single bond or hydro carbon group, R2 is hydroxyl group, thiol group, amino group or carbonyl group which bonds with amino acid , R3 and R4 is a group represented by general formula C, wherein, R5 is hydroxyl group, thiol group, amino group or carbonyl group which bonds with amino acid (see claim 18).
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US’799 teaches the method for preparation of the peptide by liquid phase synthesis, wherein the carrier consists of aromatic ring moiety and alkyl chains having 10 or more carbons as a fundamental skeleton represented by general formula A which has a functional group for bond amino acid with cycloalkanephilic moiety at the end (see claim 23). Also, US’799 teaches the method for preparation of peptide by liquid phase synthesis of claim 23, wherein the compound represented by general formula A is the compound selected from the group of represented by general formulae B (see claim 24).
US’799 teaches the residue of the compound represented by general formula A is called as carrier in the present invention (see [0017]).
US’799 presents examples of the carrier, such as shown below (SC implies soluble carrier) (see [0049])
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The benzyl derivative disclosed by US’799 (shown above) is similar to the example set forth by the instantly claimed compound species (see instant Specification [0169]).
At the time before the effective filling date of the claimed invention, it would have been prima facie obvious to one of ordinary skill in the art to use the method for producing a peptide compound, including method for producing an amino acid protecting reagent as taught by CA’772, may be appropriately modified by using a benzyl derivative (substituted benzyl compound ) protective group-forming reagent (as in the instant claim as Formula (1)) as taught by US’799, to arrive at the presently claimed invention. One of skill in the art would appreciate that the method for producing a peptide compound includes a step using a C-terminal protecting step of protecting a carboxy group of an amino acid (see [0009], CA’772). The artisan of ordinary skill in the art would have been motivated to do so with a reasonable expectation of success in synthesizing peptide compound with C-terminal protective group-forming reagent benzyl derivative (see [0049], US’799) with an expectation to achieve excellent yield (see [0005], CA’772) with precipitation and impurities eliminated (see [0111], CA’772).
Regarding claim 1; CA’772 teaches a method for producing a peptide compound, comprising: a step of using a compound, where ring A represents a condensed polycyclic aromatic hydrocarbon ring, YA's each independently represent -CH2OH, -CH2NHR, -CH2SH, or -CH2X0 , where R represents a hydrogen atom, an alkyl group, or an aralkyl group, and Xrepresents Cl, Br, or I, k represents an integer of 1 to 5 and n represents 1 or 2, RA's each independently represent an aliphatic hydrocarbon group or an organic group having an aliphatic hydrocarbon group, the number of carbon atoms in at least one aliphatic hydrocarbon group included in at least one RA is 12 or more, and the ring A may further have a substituent in addition to YA and RA (see claim 1).
Regarding claim 9; CA’772 teaches a protective group-forming reagent comprising:a ring A, YA's each independently represent -CH2OH, -CH2NHR, -CH2SH, or -CH2X0 , where R represents a hydrogen atom, an alkyl group, or an aralkyl group, and X represents Cl, Br, or I, k represents an integer of 1 to 5 and n represents 1 or 2, RA's each independently represent an aliphatic hydrocarbon group or an organic group having an aliphatic hydrocarbon group, the number of carbon atoms in at least one aliphatic hydrocarbon group included in at least one RA is 12 or more, and the ring A may further have a substituent in addition to YA and RA (see claim 14).
Regarding claim 10; CA’772 teaches the protective group-forming reagent, wherein the protective group-forming reagent is a protective group-forming reagent of a carboxy group or an amide group (see claim 15).
Regarding claim 11; CA’772 teaches the protective group-forming reagent, wherein the protective group-forming reagent is a C-terminal protective group-forming reagent of an amino acid compound or a peptide compound (see claim 16).
Regarding claim 12; US’799 teaches the compound represented by general formulae B (see [0033]).
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In above mentioned general formulae B, X, R and n are same as to that of general formula A. Q is a single bond or hydro carbon group, R2 is hydroxyl group, thiol group, amino group or carbonyl group which bonds with amino acid, R3 and R4 is a group represented by general formula C (see [0034]),
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R5 is hydroxyl group, thiol group, amino group or carbonyl group which bonds with amino acid (see [0035]).
Regarding claim 2; CA’772 teaches the method for producing a peptide compound, wherein the step of using the compound is a C-terminal protecting step of protecting a carboxy group or an amide group of an amino acid compound or a peptide compound with the condensed polycyclic aromatic hydrocarbon compound represented by Formula (1) (see claim 2).
Regarding claim 3; CA’772 teaches the method for producing a peptide compound, wherein the amino acid compound or the peptide compound in the C-terminal protecting step is an N-terminal protected amino acid compound or an N-terminal protected peptide compound (see claim 3).
Regarding claim 4; CA’772 teaches the method for producing a peptide compound according to claim 3, further comprising: an N-terminal deprotecting step of deprotecting an N-terminal end of an N-terminal and C-terminal protected amino acid compound or an N-terminal and C-terminal protected peptide compound, which is obtained in the C-terminal protecting step; and a peptide chain extending step of condensing the N-terminal end of a C-terminal protected amino acid compound or a C-terminal protected peptide compound, which is obtained in the N-terminal deprotecting step, with an N-terminal protected amino acid compound or an N-terminal protected peptide compound (see claim 4).
Regarding claim 5; CA’772 teaches the method for producing a peptide compound, further comprising: a precipitating step of precipitating an N-terminal and C-terminal protected peptide compound obtained in the peptide chain extending step (see claim 5).
Regarding claim 6; CA’772 teaches the method for producing a peptide compound, further comprising, one or more times in the following order after the precipitating step: a step of deprotecting an N-terminal end of the obtained N-terminal and C-terminal protected peptide compound; a step of condensing the N-terminal end of the obtained C-terminal protected peptide compound with an N-terminal protected amino acid compound or an N-terminal protected peptide compound; and a step of precipitating the obtained N-terminal and C-terminal protected peptide compound (see claim 6).
Regarding claim 7; CA’772 teaches the method for producing a peptide compound, further comprising: a C-terminal deprotecting step of deprotecting a C-terminal protective group (see claim 7).
Regarding claim 8; CA’772 teaches the method for producing a peptide compound, wherein a total number of carbon atoms in all aliphatic hydrocarbon groups included in all RA's is 36 to 80 (see claim 9).
Regarding claim 13; CA’772 teaches the method for producing a peptide compound, wherein YA's each independently represent -CH2OH, -CH2NHR, -CH2SH, or -CH2X0 , where R represents a hydrogen atom, an alkyl group, or an aralkyl group, and X represents Cl, Br, or I, RA's each independently represent an aliphatic hydrocarbon group or an organic group having an aliphatic hydrocarbon group, the number of carbon atoms in at least one aliphatic hydrocarbon group included in at least one RA is 12 or more, Rs's each independently represent a substituent, n10 represents an integer of 0 to 6, and n20, n21, and n30 each independently represent an integer of 0 to 5 (see claim 10).
Regarding claim 14; CA’772 teaches the method for producing a peptide compound, wherein the ring A is a naphthalene ring (see claim 8).
It is noted, that US’799 outlines the extending process of peptide chain consisting of soluble carrier [SC]-valine(Val)-glycine-Fmoc(SC)-Val-Gly-Fmoc) using soluble carrier [SC] is shown as follows (see [0049]).
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The benzyl derivative (see “SC” above) disclosed by US’799 above is similar to the example set forth by the instantly claimed compound species (see instant specification [0169]).
Therefore, at the time before the effective filling date of the claimed invention, it would have been prima facie obvious to one of ordinary skill in the art to use the method for producing a peptide compound, including method for producing an amino acid protecting reagent as taught by CA’772, may be appropriately modified by using a benzyl derivative (substituted benzyl compound ) protective group-forming reagent (as in the instant claim as Formula (1)) as taught by US’799, to arrive at the presently claimed invention. One of skill in the art would appreciate that the method for producing a peptide compound includes a step using a C-terminal protecting step of protecting a carboxy group of an amino acid (see [0009], CA’772); and that peptide synthesis reactions can be applied to the synthesis of oligomers or polymers (see [0018], US’799). The artisan of ordinary skill in the art would have been motivated to do so with a reasonable expectation of success in synthesizing peptide compound with C-terminal protective group-forming reagent benzyl derivative (see [0049], US’799) with an expectation to achieve excellent yield (see [0005], CA’772) with precipitation and impurities eliminated (see [0111], CA’772).
Therefore, the presently claimed invention was prima facie obvious to one of ordinary skill in the art at the time of the effective filling date.
Prior Art of Record
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. It is noted that the instant compound may be an isostere of the condensed polycyclic aromatic hydrocarbon compound (as taught by CA’772) with substituted benzyl compound (as taught by US’799).
Thornber, C. W. (Isosterism and Molecular Modification in Drug Design; Chem. Soc. Rev., 8, 563-580, published January 1, 1979) teaches bioisosterism can be an aid to the design of modifications; in making a bioisosteric replacement the following parameters of the group being changed could be considered : (a) Size, (b) Shape (bond angles, hybridization), (c) Electronic distribution (polarizability, inductive effects, charge, dipoles), (d) Lipid solubility, (e) Water solubility, (f) pKa, (g) Chemical reactivity (including likelihood of metabolism), and (h) Hydrogen bonding capacity (see page 565, paragraph 1). Thornber teaches bioisosteres are groups or molecules which have chemical and physical similarities producing broadly similar biological properties (see page 563, Introduction).
Conclusion
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KOYELI BANERJEE whose telephone number is (571)272-5751. The examiner can normally be reached Monday-Friday 8-4PM.
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/KOYELI BANERJEE/Examiner, Art Unit 1658
/Melissa L Fisher/Supervisory Patent Examiner, Art Unit 1658
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