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 .
DETAILED ACTION
This Office action is responsive to Applicant's Remarks/Amendment after Non-Final Rejection, filed Nov. 21, 2025. As fled, claims 1, 3, 4, 6, 7, 10-15, 17, 18, 20, 23-28, 30, 32, 35, 37, 39, 40, 42, 44, and 46 are pending, of which claims 1, 3, 4, 6, 7, 10-15, 17, 18, 20 are amended. Claims 23-28, 30, 32, 35, 37, 39, 40, 42, 44, and 46 are withdrawn from consideration as pertaining to non-elected invention.
A complete response to this Office Action should include cancellation of non-elected subject matter or other appropriate action.
Rejections Withdrawn
Applicants’ amendment, have been fully considered and are entered. The status for each rejection and/or objection in the previous Office Action is set out below.
1. The rejection of claims 1, 3, 4, 6, 7, 10-15, 17, 18, and 20 under 35 U.S.C. § 112(b) is withdrawn in view of claim amendments to specify a composition comprising 1,3-BG.
2. The rejection of claim 1 under 35 U.S.C. § 102(a)(1) and 102(a)(2) as being anticipated by WO2014/207179 Dec. 2014 s withdrawn in view of claim amendments.
3. The rejection of claim 1 under 35 U.S.C. § 102(a)(1) and 102(a)(2) as being anticipated by US 8445244, by Burgard et al. Aug, 25, 2011 is s withdrawn in view of claim amendments.
4. The rejection of claims 1, 3, 4, 6, 7, 10-15, 17, 18, and 20 under 35 U.S.C. § 103 over US 8445244, by Burgard et al. , Aug, 25, 2011 is withdrawn per claim amendments.
The following are modified or new grounds of rejections necessitated by Applicants’ amendment, filed on 11/21/2025 wherein the limitations in pending claims as amended now have been changed. The limitations in the amended claims have been changed and the breadth and scope of those claims have been changed.
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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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, 3, 4, 6, 7, 10-15, 17, 18, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over US 2003/0032153 A1 by Yamamoto et al. Feb. 13, 2003 (cited by Applicants in IDS).
The ‘153 publication teaches a method for producing (R) -1,3-butanediol or 1,3-butylene glycol by stereoselectively reducing 4-hydroxy-2-butanone using recombinants that express the enzyme [0001]; [0033]-[0035].
The ‘153 publication discuss compositions comprising 4-hydroxy-2-butanone and (R) -1,3-butanediol of optical purity 99% ee in examples 7 on [0213] and example 18 on [0245] which read on the claimed bioderived composition comprising bioderived 1,3-butylene glycol (1,3-BG) and 4-hydroxy-2-butanone (instant claims 1, 3, 4, 6, 7).
The claimed composition comprising bioderived 1,3-butylene glycol (1,3-BG) and 4-hydroxy-2-butanone.
Regarding the limitation of claims 1, 3, 15, 18, 20 of bioderived 1,3-BG composition versus the petro-BD, the prior art teach bioderived 1,3-BD composition therefore presumed to be the same inherent properties.
Regarding the limitation of claim 1 : “…the bioderived 1,3-BG does not have characteristic off-odor …” Said recitation represents an inherent property of the compositions.
The missing descriptive matter “does not have characteristic off-odor” would be recognized by persons of ordinary skill in the art as inherent from the chemical makeup of composition comprising bioderived 1,3-BG with 4-hydroxy-2-butanone.
Regarding instant claims 10 the ‘153 publication teach 1,3-butanediol is a useful compound that serves as a raw material for synthetic intermediates of antibiotics [0002].
Regarding the purity of the bioderived 1,3-butanediol, the composition compared to petro-BG and GS-MS, MS characterization of claims 3, 4, 7, 11-15, 17, 18, 20 the ‘153 teach producing bioderived optically active 1,3-butanediol of high optical purity with a high reaction yield, which reads on claimed compositions, as alternative to synthetic methods outlined on [0002]-[0008].
The limitation of claim 17 “the overall level of heavies is 0.8% or less, and
the overall level of lights is 0.2% or less” read on zero or absence of the contaminants. The limitation of claims 18 and 20 “does not comprise detectable levels of 1-4-(4-methyl-l,3-dioxan-2-yl) propan-2-one read on zero- or absence of the contaminants.
Analysis by liquid chromatography using an optical resolution column.
and liquid chromatography was carried out with an elution solution of hexane:isopropanol=19:1, a flow rate of 1.0 mL/min, monitoring at a wavelength of
220 nm, and a temperature of 40° C. As a result, the 1,3-butanediol was in the (R) conformation with an enatiomer excess of 99% ee or more. [0213]. Further, the resulting 1,3-butanediol was quantified by gas chromatography to determine the yield relative to the, 4-hydroxy-2-butanone. The conditions for gas chromatography on [0214].
Furthermore, products of identical chemical composition cannot have mutually exclusive properties. A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the composition comprising compounds 1,3-butylene glycol and 4-hydroxy-2-butanone of identical chemical structure, the properties applicant discloses and/or claims -the GC-MS retention; UV absorbance; mass spectrometry; odor- are necessarily present. See also MPEP § 2112.01.
The instant claims differ from the prior art in that the ‘153 publication does not specifically teach the purity of the 1,3-butanediol and the concentration of byproducts or additional components of the composition (e.g. 2,3 butanediol, propanediols).
Regarding the purity of the 1,3, bioderived butanediol, the prior art discuss separation from culture medium, (R)-1,3-butanediol is extracted into the solvent layer after removing cell bodies of the microorganism by centrifugation of the reaction solution containing the microorganism, and adding solvent, such as ethyl acetate, to the filtrate. Then, the solvent phase is separated and distilled to purify the (R)-1,3-butanediol to a high purity [0197].
Therefore, the prior art relied upon combined with the knowledge generally available in the art at the time of the invention, teach purification and separation techniques of 1,3 -butanediol that would have motivated the skilled artisan to purify/separate the bioderived 1,3 -butanediol compound to desired grades of purity.
Per MPEP 716.02 guidance:” Any differences between the claimed invention and the prior art may be expected to result in some differences in properties. The issue is whether the properties differ to such an extent that the difference is really unexpected. In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).”
And further MPEP 2144.04:” Factors to be considered in determining whether a purified form of an old product is obvious over the prior art include whether the claimed chemical compound or composition has the same utility as closely related materials in the prior art, and whether the prior art suggests the particular form or structure of the claimed material or suitable methods of obtaining that form or structure. In re Cofer, 354 F.2d 664, 148 USPQ 268 (CCPA 1966) (Claims to the free-flowing crystalline form of a compound were held unobvious over references disclosing the viscous liquid form of the same compound because the prior art of record did not suggest the claimed compound in crystalline form or how to obtain such crystals.). However, in the case of product-by-process claims, if a first prior art process is improved to enhance the purity of the product produced by the process, and if the purified product has no structural or functional difference from the products produced by other prior art processes, then the improvement in the first process that improves the purity of the product does not give rise to patentability. See Purdue Pharma v. Epic Pharma, 811 F.3d 1345, 117 USPQ2d 1733 (Fed. Cir. 2016)”
In the instant case, the prior art by ‘153 publication specifically teach that the bioderived 1,3-butanediol can be further purified by various techniques to give a high purity product suitable for industrial applications.
The rationale to support a conclusion that the claim would have been obvious is that all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results to one of ordinary skill in the art. KSR, 550 U.S. at ___, 82 USPQ2d at 1395.
Therefore, the claimed invention as a whole is prima facie obvious over the teachings of the prior art.
Conclusion
In view of the rejections to the pending claims set forth above, no claim is allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to:
Ana Muresan
(571) 270-7587 (phone)
(571)270-8587 (fax)
Ana.Muresan@uspto.gov
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692