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 .
Request for continued examination
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 6/10/2026 has been entered.
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 Claims 23-28, 30, 32, 35, 37, 39, 40, 42, 44, and 46 are withdrawn from consideration as pertaining to non-elected invention.
Claims 1, 3, 4, 6, 7, 10-15, 17, 18, and 20 are examined herein.
A complete response to this Office Action should include cancellation of non-elected subject matter or other appropriate action.
Claim Objections
Claim 4 is objected to because of the following informalities: the recitation in claim 4: ” 95% or more, 96% or more, 97% or more, 98 % or more, 99.0% or more,99.1 % or more, 99.2% or more, 99.3% or more, 99.4% or more, 99.5% or more, 99.6% or more,
99.7% or more, 99.8% or more, or 99.9% or more, and wherein the bioderived 1,3-BG has a chemical purity of 99.0% or more, 99.1 % or more, 99.2% or more, 99.3% or more, 99.4% or more, 99.5% or more, 99.6% or more, 99.7% or more, 99.8% or more, or 99.9% or more” should be revised to recite for instance: “ 99.5 % or more” instead of alternative purity as listed to address potential indefiniteness issues.
Appropriate correction is required.
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, Feb. 13, 2003 by Yamamoto et al. (cited by Applicants in IDS).
Instant claims are drawn to a composition comprising bioderived 1,3-butylene glycol (1,3-BG), wherein the composition comprises detectable levels of one or more compounds selected from the group consisting of 3-hydroxy-butanal, 4-hydroxy-2-butanone, 4-(3-hydroxybutoxy )butan-2-one, 4-(( 4-hydroxybutan-2-yl)oxy )-butan-2-one, 1,2-propanediol, 1,3-propanediol and 2,3-butanediol,wherein the bioderived 1,3-BG has a chemical purity of 95% or more, wherein both levels of methyl-vinyl-ketone and crotonaldehyde in the composition are less than 1 ppm, and wherein the bioderived 1,3-BG does not have a characteristic off-odor.
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 a bioderived 1,3-butylene glycol (1,3-BG) and 4-hydroxy-2-butanone (instant claims 1, 3, 4, 6, 7).
Regarding the limitation of claims 1, 3, 15, 18, 20 of bioderived 1,3-BG composition versus the petro-BD, the prior art teaches 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 comprising the 1,3-BG (1,3-butanediol) in high percent.
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 (1,3-butanediol) with 4-hydroxy-2-butanone impurity.
Regarding instant claim 10 the ‘153 publication teaches that the 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 as required by claims 3, 4, 7, 11-15, 17, 18, 20, the ‘153 teaches 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 instant 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. The 1,3-butanediol was in the (R) conformation with an enantiomer excess of 99% ee or more [0213]. Further, the 1,3-butanediol was quantified by gas chromatography to determine the yield relative to the, 4-hydroxy-2-butanone. The conditions for gas chromatography are listed on [0214] of the cited prior art.
It is noted that products of identical chemical composition cannot have mutually exclusive properties. A chemical composition and its properties are inseparable. Therefore, since the prior art teaches the composition comprising compounds 1,3-butylene glycol and 4-hydroxy-2-butanone of identical chemical structure, the properties of the 1,3-butanediol such as the GC-MS retention; UV absorbance; mass spectrometry; odor would necessarily be 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 discusses 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]. Furthermore, on [0213]-[0214] the prior art teaches that 1,3-butanediol produced was in the (R) conformation with an enantiomer excess of
99% ee or more, in 95% yield. 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.
In view of 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).”
Furthermore, in view of 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 discloses that the bioderived 1,3-butanediol could 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.
Response to Remarks:
Applicants argue that” The goal of Yamamoto is that of high yield
and high optical purity production of 1,3-BG, using this enzyme and consuming 4-HB as a starting material. As such, Yamamoto is directed to conversion and reduction of 4-HB, not retention in a composition and it does not describe a finished or isolated composition where 4-HB is retained at defined or controlled levels in a finished composition” (Remarks page 8).
As noted before, the MPEP 2144.04 states:” 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).
In the instant case, the prior art by Yamamoto specifically teaches bioderived (R) -1,3-butanediol or 1,3-butylene glycol and further purification by various techniques to give a high purity product suitable for industrial applications.
In reviewing the instant disclosure, the preparative examples shows methods of purification by distillation of bioderived 1,3-BD and analysis of resulting compositions.
There are no examples or data of the instant disclosure showing criticality of instantly claimed detectable levels of one or more compounds selected from the group consisting of 3-hydroxy-butanal, 4-hydroxy-2-butanone, 4-(3-hydroxybutoxy )butan-2-one, 4-(( 4-hydroxybutan-2-yl)oxy )-butan-2-one, 1,2-propanediol, 1,3-propanediol and 2,3-butanediol in the composition comprising 1,3-BD of 95% purity or more and the same compound 1m3-BD as disclosed in the prior art.
Furthermore, only in those cases where the purified product is as a result of the purification so different in properties and uses as to be in effect a new compound has such a purified product been considered patentable. The instant case does not come under this exception. In re Volwiler, 46 USPQ 137 (CCPA 1940).
The Applicant has not shown evidence of substantially improved and unexpected results between the instantly claimed composition and the prior art compound.
Please note that if Applicant intends to rely on unexpected or unforeseen results, attention is invited to MPEP 716.02. Absent clear, convincing, side-by-side data demonstrating unobviousness vis-a-vis the prior art commensurate with the scope of protection sought and showing that the claimed process and process disclosed by prior art are distinct, the claims are considered prima facie obvious.
Regarding Applicants arguments that “Yamamoto is also silent as to methyl vinyl ketone, crotonaldehyde, and off-odor” ( Remarks page 9), the limitation of insta claims “wherein both levels of methyl-vinyl-ketone and crotonaldehyde in the composition are less than 1 ppm” read on zero, or absence of the such components. The limitation “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 (1,3-butanediol).
See also MPEP 2112: WHEN THE STRUCTURE RECITED IN THE REFERENCE IS SUBSTANTIALLY IDENTICAL TO THAT OF THE CLAIMS, CLAIMED PROPERTIES OR FUNCTIONS ARE PRESUMED TO BE INHERENT:” Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977)
Conclusion
In view of the rejections to the pending claims set forth above, no claim is allowed.
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
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