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 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.
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) 1-4, 7-8,10, 12-13, 15-16 and 24-25 is/are rejected under 35 U.S.C. 103 as being unpatentable over Lin et al. (U.S. Pat. 5,554,791, hereafter US’791) in view of Patel et al. (U.S. Pub. No. 2002/0019566, hereafter US’566).
US’791 discloses the same basic EDDS synthesis: reacting aspartic acid, in particular L-aspartic acid, with a dihaloethane, including 1,2-dibromoethane, in aqueous basic medium to form [S,S]-EDDS, followed by recovery of product by cooling, acidification, precipitation, and solid isolation. US’791 discloses, for example, reacting L-aspartic acid and 1,2-dibromoethane in basic aqueous solution, heating the reaction mass to 80 C, then cooling and isolating [S,S]-EDDS by acidification and filtration. See US’791, col. 2, ll. 1-4; col. 5, ll. 5-6, 31-35, 60-67; col. 6, ll. 1-11; Example 1.
It would have been obvious to one of ordinary skill in the art, at the time the invention was made, to use the reaction-control features and recovery details of US’566 in the EDDS process taught by US’791, or vice versa, because both references are directed to the same target compound, use the same starting materials and same reaction type, and teach the same general sequence of alkaline aqueous reaction, heating, and acidic recovery. Selecting or adjusting pH, reagent addition protocol, heating, cooling, and precipitation conditions would have amounted to no more than routine optimization of known process variables in an established EDDS synthesis. See KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 417 (2007).
Regarding claim 1, US’791 discloses combining an aqueous solution of aspartic acid with dibromoethane under basic conditions to form a reaction solution, heating the reaction solution, producing a reaction product comprising [S,S]-EDDS, and recovering the product from the reaction solution. US’791, col. 2, ll. 1-4; col. 5, ll. 31-35; col. 6, ll. 1-11; Example 1. US’566 confirms the same process and expressly discloses L-aspartic acid, aqueous NaOH, dibromoethane, heating at 85 C, and recovery of the solid EDDS product after acidification. US’566, para. [0018]; Example 1
Regarding claim 2, US’791 expressly discloses cooling the heated reaction solution and precipitating at least a portion of the reaction product from the cooled reaction solution. US’791, col. 5, ll. 31-35 and 60-67; col. 6, ll. 1-11; Example 1.
Regarding claim 3, US’791 discloses a recovered product having purity well above the claimed threshold of at least about 40%. US’791 reports a wet cake containing 33.83 wt % [S,S]-EDDS and 5.59 wt.% L-aspartic acid, corresponding to 85.8 normalized wt.% [S,S]-EDDS. US’791, col. 5, ll. 31-35; col. 6, ll. 1-11; Example 1
Regarding claim 4, US’791 discloses the use of L-aspartic acid and further discloses alkaline reaction conditions above pH 9. US’791, col. 5, ll. 5-6 and 31-37; Example 1. US’566 likewise discloses L-aspartic acid in a strongly alkaline medium at pH 10.2. US’566, para. [0018]; Example 1.
Regarding claim 7, US’791 discloses continuously stirring the reaction solution and the heated reaction solution. US’791, col. 5, ll. 61-66; Example 1, describing the reaction mass heated to 80 C and stirred for 9 hours at atmospheric pressure. US’566 likewise discloses a heated reaction mixture under standard reaction conditions.
Regarding claim 8, US’566 discloses the dibromoethane addition feature. In Example 1, US’566 describes a reaction mixture containing L-aspartic acid, NaOH, water, together with 57.8 g DBE, followed by heating, which reads on the single-addition embodiment. US’566, para. [0018]; Example 1. To the extent the claim also covers addition over a selected period, varying the addition rate of dibromoethane would have been an ordinary process-control variable in the same known synthesis.
Regarding claim 10, US’566 expressly discloses maintaining the heated reaction solution at alkaline pH overlapping the claimed range. US’566 states the reaction may be conducted at pH 7-14, preferably 8-13, and Example 1 begins at pH 10.2 and adds further NaOH during heating to maintain pH. US’566, para. [0016], [0018]; Example 1. US’791 also discloses pH about 9 to about 13. US’791, col. 3, ll. 3-7.
Regarding claim 12, US’791 discloses the cooled reaction solution at about room temperature. US’791, col. 5, ll. 66-67; col. 6, ll. 1-7; Example 1, describing cooling the reactor and co-feeding the cooled reaction solution at ambient temperature.
Regarding claim 13, US’791 discloses precipitating the reaction product by acidifying the cooled reaction solution to about pH 2-4. US’791 describes co-feeding cooled reaction solution and hydrochloric acid into water at pH 2.5-2.6, producing a filtered wet cake of [S,S]-EDDS. US’791, col. 5, ll. 31-35 and 60-67; col. 6, ll. 1-11; Example 1.
Regarding claim 15, US’791 expressly discloses the use of hydrochloric acid for the acidification step. US’791, col. 5, ll. 60-67; col. 6, ll. 1-11; Example 1, using 18.25 wt. % hydrochloric acid.
Regarding claim 16, US’791 discloses that recovering the product from the reaction solution forms a liquid filtrate and that acidification produces a precipitate comprising unreacted aspartic acid. US’791 reports a filtered wet cake containing L-aspartic acid and [S,S]-EDDS after acidification and filtration, which necessarily leaves a corresponding liquid filtrate from the recovery step. US’791, col. 5, ll. 31-35 and 60-67; col. 6, ll. 1-11; Example 1. In view of US’791’s express separation and composition data, the claimed filtrate/precipitate feature would have been obvious.
Regarding claim 24, US’791 discloses a process for synthesizing [S,S]-EDDS from L-aspartic acid and dibromoethane by combining an aqueous solution of L-aspartic acid with dibromoethane under basic conditions, heating to form reaction product, cooling the heated reaction solution, precipitating product from the cooled reaction solution, and recovering the precipitated product, where the recovered product is more than 40% pure [S,S]-EDDS. US’791, col. 2, ll. 1-4; col. 5, ll. 31-35, 60-67; col. 6, ll. 1-11; Example 1. US’566 reinforces the same reaction and recovery sequence with alkaUS’791e pH control and HCl acidification. US’566, para. [0016], [0018]; Example 1.
Regarding claim 25, US’791 discloses combining aqueous L-aspartic acid and dibromoethane under basic conditions to form a reaction solution, forming [S,S]-EDDS reaction product, and separating the EDDS as a solid product from the reaction mixture after formation. US’791’s Example 1 culminates in acidification, filtration, and an isolated wet cake containing [S,S]-EDDS. US’791, col. 5, ll. 31-35 and 60-67; col. 6, ll. 1-11. US’566 also discloses the same essential sequence, ending in the collection of the solid product by filtration after acidification. US’566, para. [0018]; Example 1.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1, 8, and 10 is/are rejected under 35 U.S.C. 102(a)(1)/(a)(2) as being anticipated by Patel et al. (U.S. Pub. 2002/0019566, hereafter US’566).
US’566 teaches a process for preparing amino acid derivatives by reacting, in an aqueous medium at a pH in the range of 7-14 and preferably in aqueous alkali, a dihalo compound with an amino acid or salt thereof. US’566 further teaches that the reaction proceeds generally in the range of pH 8-13 and preferably pH 9-12. US’566’s working examples use L-aspartic acid, aqueous sodium hydroxide, water, and DBE, with heating, pH control during reaction, acidification to pH 3 with hydrochloric acid, and recovery of solid (S,S)-EDDS by filtration. US’566, p. 3, para. bridging paras. 5-6; p. 8, para. 1; Example 1.
Regarding claim 1, US’566 teaches combining an aqueous solution of aspartic acid with dibromoethane under basic conditions to form a reaction solution, because US’566 teaches “a reaction mixture containing 150.1 g L-Aspartic acid, 140.0 g of 50% aq. NaOH, and 210.9 g water at a pH of 10.2 at 25°C together with 57.8 g of DBE.” US’566 further teaches heating the reaction solution, because US’566 states that the mixture “was heated at 85°C for 4 hours,” with additional NaOH added during that time to maintain pH. US’566 also teaches that the heated reaction solution comprises a reaction product including (S,S)-EDDS, because US’566 states that “[t]he solid product was (S,S)-Ethylenediaminedisuccinic acid,” and further states that “no other isomers were detected in the product.”
US’566 also teaches recovering at least a portion of the reaction product from the reaction solution, because US’566 states that the solution “was acidified with 36% HCl to pH 3, maintaining the temperature below 50°C” and that “[t]he solid product was collected by filtration.” US’566, Example 1, p. 8, paras. 2-4.
Regarding claim 8, US’566 teaches the embodiment in which dibromoethane is combined with the aqueous solution as a single addition. In Example 1, US’566 describes the reaction mixture as containing L-aspartic acid, aqueous NaOH, water, and DBE at the outset of the heated reaction. In other examples, US’566 also states that DBE “was added” to the mixture before heating. This reads on the alternative requiring that dibromoethane be combined with the aqueous solution as a single addition. US’566, Example 1; Example 13.
Regarding claim 10, US’566 teaches maintaining the heated reaction solution at a pH between about 9 and 14. US’566 expressly teaches that the reaction proceeds at pH 7-14, generally 8-13, and preferably 9-12. US’566’s Example 1 further teaches an initial pH of 10.2 and states that “an additional 50.1 g of 50% aq. NaOH was added to maintain the pH” during the 85°C reaction period. This reads on the limitation of maintaining the heated reaction solution within the claimed alkaline range during reaction. US’566, p. 3, para. bridging paras. 5-6; Example 1, p. 8, para. 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 22-23 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 22, which depends from claim 1, recites “the bromine gas.” However, claim 1 does not recite bromine gas, nor does claim 1 provide antecedent basis for that limitation. Bromine gas is first introduced in claim 17, not claim 1. As a result, the dependency of claim 22 is improper, and the scope of the claim is unclear.
Claim 22, as presently written, refers to subject matter not recited in the claim from which it depends, one of ordinary skill in the art would not be able to determine the metes and bounds of the claim with reasonable certainty. Claims which depend from an indefinite claim are also indefinite. Ex parte Cordova, 10 U.S.P.Q.2d 1949, 1952 (P.T.O. Bd. App. 1989).
Allowable Subject Matter
Claims 17-23 objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -6:30 pm).
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/DEBORAH D CARR/ Primary Examiner, Art Unit 1691