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 .
Claim Status
Claims 1-20 are pending.
Claims 9-10 have been amended.
No claims have been cancelled.
Claims 11-20 have been newly added.
Thus, claims 1-20 represent all claims currently under consideration.
Priority
Domestic Priority data as claimed by Applicant:
This application is a 371 of PCT/CN2021/118311 (09/14/2021)
Foreign Applications:
CHINA 202111048925.X (09/08/2021)
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claim 1 is objected to because of the following informalities:
In line 4, the word “and” should be deleted.
In line 5, “Michael addition reaction,” should read “Michael addition reaction;”.
Claim Interpretation
The term “alkali” as recited in instant claims 2-3, 5-9, 11-12, 14-18, and 20 will be interpreted as alkali metals in view of the specification, (Specification; page 3, paragraph 2).
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 1-20 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 the phrase “hydrolyzing at least one of maleic anhydride, maleic acid, and fumaric acid to obtain a hydrolyzed salt solution” in lines 3-4. However, for embodiments of the recited claim comprising maleic acid, fumaric acid, or a combination thereof, it is unclear how one could hydrolyze these compounds. The process of obtaining a salt solution of either of these compounds, for example by mixing with a solution of NaOH as described in the specification (Examples 2-3 and 7), would be understood as deprotonation or salt formation, rather than a hydrolysis process. This issue also appears in claims 2, 4, 11, and 13 and this ambiguity renders the instant claims indefinite. For the purposes of examination, this phrase will be interpreted as reacting the acid with a base to make a salt of corresponding acid.
Regarding claims 2-20, these dependent claims do not resolve the indefiniteness of claim 1 detailed above.
Regarding claims 3, 9, and 19, these dependent claims do not resolve the indefiniteness of claim 2 detailed above.
Regarding claims 12 and 18, these dependent claims do not resolve the indefiniteness of claim 11 detailed above.
Claim 8 recites the phrase “dropwise adding the chloroacetic acid and an alkali solution, both in an equal molar weight to at least one raw material of the maleic anhydride, the maleic acid, and the fumaric acid” in lines 5-7. However, it is unclear as written whether or not the term “molar weight” is referring to the use of equal moles (i.e., a molar equivalent) of chloroacetic acid, an alkali solution, and the at least one raw material. The specification does not provide adequate detail to address this issue, and this ambiguity renders the instant claim indefinite.
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.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], 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 2 is rejected 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.
Claim 2 recites “wherein the step of hydrolyzing at least one of maleic anhydride, maleic acid, and fumaric acid comprises: mixing at least one of the maleic anhydride, the maleic acid, and the fumaric acid with at least one of water, methanol, ethanol, and isopropanol, and then adding an alkali solution dropwise”. However, for instances wherein water is absent, the “hydrolyzing” would be expected to occur through the action of at least one of methanol, ethanol, and isopropanol. The specification defines the “hydrolyzing” process as a “hydrolysis neutralization reaction” (page 6, paragraph 6), and the term “hydrolysis” is defined as solvolysis by water, as evidenced by IUPAC Goldbook (PAC, 1994, 66, 1077 on page 1123; published online 2014). Therefore, the instant claim improperly broadens the definition of “hydrolyzing” to include methanol, ethanol, and isopropanol, and thus fails to further limit the subject matter of claim 1 on which the instant claim depends.
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
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.
Claims 10-18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shi et al. (CN109912440A; published 06-21-2019; English language machine translation obtained from Espacenet on 08-30-2026).
Regarding claims 10-18, claim 10 recites “An L-aspartic acid N,N-diacetic acid tetrasodium salt, prepared by the preparation method for L-aspartic acid N,N-diacetic acid tetrasodium salt according to claim 1”. For the purposes of examination, the recited method step is being interpreted as a product-by-process limitation. MPEP § 2113(I) states that “[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” The process limitations of claims 1 and 11-20 are only defining the process of the product-by-process limitation and do not appear to impart any further structural features to the claimed product. Therefore, the salt of Shi is also interpreted to anticipate these claims, as detailed below.
Further regarding claims 10-18, Shi discloses amino type chelating agents including tetrasodium aspartate diacetate, wherein the amino acids used can be L-type or D-type, or a mixture of L-type and D-type (Title; Abstract; 0035, 0205-0212; Example 18; English language machine translation).
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.
Claims 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Shi et al. (CN109912440A; published 06-21-2019; English language machine translation obtained from Espacenet on 08-30-2026), in view of Okada et al. (JPH09157232; published 06-17-1997; English language machine translation obtained from Espacenet on 08-31-2026) and as further evidenced by Schwendner et al. (“Exploring Microbial Activity in Low-Pressure Environments”; Curr. Issues Mol. Biol. 2020, 38, 163-196; published 01-22-2020).
Regarding claims 1 and 10, Shi teaches a large-scale preparation method of amnio acid type chelating agents, wherein the amino acids used can be L-type or D-type, or a mixture of L-type and D-type. The method of Shi includes a large scale preparation of tetrasodium aspartate diacetate from aspartic acid and chloroacetic acid (Title; Abstract; 0035, 0205; Example 18; English language machine translation; 0204 and Scheme 25 of Original Document):
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Shi does not teach a preparation method for L-aspartic acid N,N-diacetic acid tetrasodium salt comprising hydrolyzing at least one of maleic anhydride, maleic acid, and fumaric acid to obtain a hydrolyzed salt solution; and subjecting the hydrolyzed salt solution and glycine to a Michael addition reaction.
However, Okada teaches the production of aminopolycarboxylic acid in high purity and yield as chelating agents with superior biodegradability, including monoacetic aspartic acid:
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The method comprises performing a Michael addition reaction using L-form or D-form amino acids and maleic acid or alternatively maleic anhydride in the presence of base under controlled conditions. Example 1 of Okada teaches the production of monoacetic aspartic acid sodium salt by first mixing maleic anhydride with water and sodium hydroxide solution while cooling and stirring. To this solution, glycine was added and the reaction was continued under reflux for 4 hours, the reaction mixture was analyzed by 1H NMR, and the amount of the target sodium salt produced was 91.4% (Title; Abstract; 0002-0004; 0016-0017, 0022; Example 1; English language machine translation; 0020, Compound 1 of Original Document). The skilled artisan would reasonably interpret the initial mixing of maleic anhydride with sodium hydroxide with cooling and stirring in Example 1 of Okada as hydrolyzing maleic anhydride to obtain a hydrolyzed salt solution, in a manner consistent with the first method step of instant claim 1.
The methods of Shi and Okada are analogous because they reside in the closely overlapping technical field of biodegradable polycarboxylic acid chelating agents produced from amino acids, in a manner consistent with the instantly claimed invention. Since Okada teaches the preparation of monoacetic aspartic acid sodium salt as a chelating agent and Shi teaches that aspartic acid reacts with chloroacetic acid to produce the claimed salt, the skilled artisan would recognize that the aspartic acid starting material of Shi could be substituted with the monoacetic aspartic acid sodium salt obtainable by the method of Okada to arrive at an alternative production method for L-aspartic acid N,N-diacetic acid tetrasodium salt with a reasonable expectation of success. Such an endeavor would result in the simple substitution of one known element for another to obtain predictable results. See MPEP § 2143(I)(B).
The skilled artisan would further recognize that the monoacetic aspartic acid sodium salt of Okada would predictably react to form aspartic acid N,N-diacetic acid tetrasodium salt using the method of Shi, because Shi teaches a di-alkylation reaction with chloroacetic acid from aspartic acid that forms monoacetic aspartic acid sodium salt (i.e., the mono-alkylation product) en route to producing aspartic acid N,N-diacetic acid tetrasodium salt (i.e., the di-alkylation product).
Finally, since the methods of both Okada and Shi teach the use of aqueous NaOH solution as the reacting medium, the skilled artisan would recognize that these two processes could be coupled together in a one-pot process, such that after the monoacetic aspartic acid sodium salt is formed as measured by 1H NMR analysis after 4 hours of reflux (Okada; 0022 and Example 1; English language machine translation), chloroacetic acid and catalytic potassium iodide could then be predictably added according to the method of Shi (Shi; 0211; Example 18; English language machine translation) to produce the aspartic acid N,N-diacetic acid tetrasodium salt in a one-pot, streamlined process with a reasonable expectation of success. In this modified production method, the skilled artisan would predictably use at least 1 molar equivalent less chloroacetic acid than the method of Shi alone (Example 18 of Shi uses 2.12 molar equivalents), because only one N-alkylation would be required in the modified process.
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have substituted the aspartic acid starting material of Shi with the monoacetic acid sodium salt of the process of Okada to arrive at the invention of claims 1 and 10. The motivation to do so would permit the skilled artisan to predictably pursue, with a reasonable expectation of success, an alternative production method for L-aspartic acid N,N-diacetic acid tetrasodium salt, as described above.
Regarding claims 2 and 11, Example 1 of Okada teaches that maleic anhydride was mixed with water, and NaOH aqueous solution was slowly added while cooling and stirring (0022; Example 1; English language machine translation). Okada further teaches that the solvent used in the reaction is not limited as long as it does not participate in the reaction, but water or organic solvents can be used, including methanol, ethanol, and 2-propanol (0019; English language machine translation). Although Okada does not explicitly teach adding an alkali solution dropwise, the skilled artisan could arrive at this limitation based on the teachings of Okada and through means of routine optimization that is non-inventive in nature. See MPEP § 2144.05(II).
Regarding claims 3-4, 12-13, and 19, Okada teaches that the reaction temperature varies is generally preferred to be between 70 ºC and 150 ºC (0020; English language machine translation). This temperature range overlaps with ranges recited in the instant claims. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Regarding claims 5 and 14, Example 1 of Okada teaches glycine is added to a solution of maleic anhydride and aqueous NaOH (0022; Example 1; English language machine translation). Although Okada does not explicitly teach to the hydrolyzed salt solution adding the glycine and an alkali solution as recited in the instant claims, Okada does teach that there are no particular restrictions on the order in which the raw materials are mixed (0019; English language machine translation). Furthermore, this difference between the method of Okada and the instant claims merely reflect a re-ordering of process steps that is non-inventive in nature. MPEP § 2144.04(IV) states that the “selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results.” Okada further teaches that the reaction temperature is generally preferred to be between 70 ºC and 150 ºC (0020; English language machine translation). This temperature range overlaps with ranges recited in the instant claims. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.”
Okada does not explicitly teach a Michael addition reaction pressure of 0-10 MPa, as recited in the instant claims. Instead, Okada is silent regarding the reaction pressure. In spite of this deficiency, the skilled artisan could reasonably deduce that the method of Okada is performed at atmospheric pressure, absent any specific teaching directing the skilled artisan to control the pressure externally. Furthermore, Shi teaches that the reaction of amino acids with haloacetic takes place at atmospheric pressure (Shi; 0032; English language machine translation). Earth’s global average atmospheric pressure at sea level is 101.3 kPa (0.1 MPa), as evidenced by Schwendner (page 163, first paragraph of Introduction). Thus, when considering the combined process of Shi and Okada, the skilled artisan could arrive at a preparation method for L-aspartic acid N,N-diacetic acid tetrasodium salt at a reaction pressure of 0.1 MPa with a reasonable expectation of success, and this pressure resides within the range recited in the instant claims. See MPEP § 2144.05(I).
Okada does not explicitly teach a Michael addition reaction pressure that comprises controlling a temperature at a second temperature range at 45 ºC – 100 ºC, and then adding potassium iodide, as recited in the instant claims. However, Shi teaches that the reaction of amino acids with haloacetic acid takes place at a reaction temperature of 40 ºC to 120 ºC under the action of an iodide catalyst, and Example 18 of Shi teaches the preparation of to form tetrasodium aspartate diacetate comprising maintaining the temperature at 45.0-50.0 ºC and adding potassium iodide (Abstract; claims 1 and 4; 0034; 0037; 0205-0212; Example 18). Thus, when considering Shi in view of Okada, the skilled artisan could arrive at a preparation method for L-aspartic acid N,N-diacetic acid tetrasodium salt comprising controlling at a temperature of 40 ºC to 120 ºC and adding potassium iodide to react, and this temperature overlaps with the range recited in the instant claims. See MPEP § 2144.05(I). Furthermore, the combined process of Shi and Okada is consistent with the method steps of the present application, wherein potassium iodide is added after the Michael addition takes place in order to act as a catalyst in the subsequent method step with chloroacetic acid (Specification; pages 7-9, Examples 1-7). Therefore, it would have been prima facie obvious to arrive at the invention of claims 5 and 14 based on the teachings of Shi, Okada, Koenig, and Nambu and the evidentiary teachings of Schwendner.
Regarding claims 6-7 and 15-16, Example 1 of Okada teaches that glycine was added to a solution of maleic anhydride and NaOH solution, and then water was added to adjust the molar concentrations of maleic acid and amino acid each to 3 mol/liter (0022; Example 1; English language machine translation).
Although Okada does not explicitly teach mixing the glycine and the alkali solution, and then dropwise adding mixed glycine and alkali solution to the hydrolyzed salt solution as recited in instant claims 6 and 15, or adding the glycine and the alkali solution simultaneously as recited in claims 7 and 16, Okada does teach that there are no particular restrictions on the order in which the raw materials are mixed (0019; English language machine translation). This difference between the method of Okada and the instant claims merely reflect a re-ordering of process steps that is non-inventive in nature. MPEP § 2144.04(IV) states that the “selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results.” Further regarding the limitation dropwise adding, Example 1 of Okada does teach the slow addition of alkali solution (0022; Example 1; English language machine translation). Although Okada does not explicitly teach adding an alkali solution dropwise, the skilled artisan could arrive at this limitation based on the teachings of Okada and through means of routine optimization that is non-inventive in nature. See MPEP § 2144.05(II).
Regarding claims 8 and 17, Example 18 of Shi teaches a preparation method of tetrasodium aspartate diacetate, wherein an alkali (sodium hydroxide) solution is added dropwise, and after 5 minutes chloroacetic acid solution is added dropwise (0205-0212; Example 18; English language machine translation). Although Shi does not explicitly teach adding the chloroacetic acid and an alkali solution simultaneously after the Michael addition reaction, Shi does teach that various substitutions or modifications made based on common technical knowledge and conventional methods in the art should be included within the scope of this invention (0057; English language machine translation). Furthermore, this difference between the method of Shi and the instant claims merely reflect a re-ordering of process steps that is non-inventive in nature. MPEP § 2144.04(IV) states that the “selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results.” The skilled artisan would further recognize based on the combined teachings of Shi and Okada that the method step of Shi comprising the addition of chloroacetic acid and an alkali solution would be performed after the initial Michael addition method step with glycine and maleic acid or maleic anhydride is complete, as taught by Okada, in a manner consistent with the instantly claimed invention.
Further regarding claims 8 and 17, Example 18 of Shi does not explicitly teach that the chloroacetic acid and an alkali solution are both in equal molar weight to at least one raw material of the maleic anhydride, the maleic acid, and the fumaric acid as recited in the instant claims. However, Shi does teach that the molar ratio of the amino acid raw material is 1 part, the amount of haloacetic acid is 1.0 to 5.0 parts, and the amount of base is 1.0 to 6.0 molar parts (claim 6; 0039; English language machine translation). Therefore, when considering these teachings in view of Okada who teaches the use of maleic acid or maelic anhydride (0016 and 0022; Example 1; English language machine translation), the skilled artisan could arrive at a process with an equal molar weight of chloroacetic acid, sodium hydroxide, and maleic acid or maleic anhydride with a reasonable expectation of success through means of routine experimentation that is non-inventive in nature. MPEP § 2144.05(II) states that “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.”
Regarding claims 9, 18, and 20, Example 1 of Okada teaches the production of monoacetic aspartic acid sodium salt by first mixing maleic anhydride with water and sodium hydroxide solution while cooling and stirring (0022; Example 1; English language machine translation). Okada further teaches that examples of bases used in the reaction include alkali metal hydroxides, for example lithium hydroxide, sodium hydroxide, and potassium hydroxide (0018; English language machine translation).
Based on the combined teachings of the references, the Examiner submits that a person of ordinary skill in the art would have had a reasonable expectation of success of arriving at the instantly claimed method and compound. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, and absent a clear showing of evidence to the contrary.
Conclusion
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to Derek Rhoades whose telephone number is (703)-756-5321. The Examiner can normally be reached Monday–Thursday, 7:30 am–5:00 pm EST; Friday, 7:30 am–4:00 pm EST.
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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