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 .
Status of Claims
The amendments to the claims filed April 29, 2026 are acknowledged and entered. Claims 1-2 and 6-23 are pending.
Examiner notes that the instant claims are marked with serial no. 18/061,235 (see header space; pictured below). This number appears to correspond to an unrelated US application. This serial number confuses the record and should be deleted from the claims.
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Priority
This application is a 371 of PCT/EP2022/069142, filed July 8, 2022, which claims priority of GB2111203.2, filed August 3, 2021.
Information Disclosure Statement
Acknowledgement is made of the Information Disclosure Statement filed on March 22, 2024. All references have been considered except where marked with a strikethrough.
Specification
The specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any of the errors of which applicant may become aware of in the specification.
Election/Restriction
Applicant’s election of Group 1 (claims 1-2 and 6-14) in the reply filed on April 29, 2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)). Therefore this restriction is considered proper and thus made FINAL. Claims 15-23 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Applicant’s election with traverse of species corresponding to 2-butyl-3, 4-dimethyl-5-phenyl-1,3,2-oxazaborolidine (pictured below for convenience) in the reply April 29, 2026 is acknowledged.
The traversal is on the ground(s) the examination of various identified species would not be unduly burdensome and substantive examination should proceed on oxazaborolidines as broadly claimed. These arguments are not persuasive for the reason that the claims do not require that the oxazaborolidine have any particular structure. The term oxazaborolidine embraces an indefinite number of structurally distinct compounds that would require separate searches. The species election requirement is still deemed proper and is therefore made FINAL.
Elected Species
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The guidelines in MPEP § 803.02 provide that upon examination if prior art is found for the elected species, the examination will be limited to the elected species.
The elected species was found in the prior art and the search was limited to the elected species
Claim 14 (in full) and claims 1-2 and 6-13 (all in part, other than the elected species) are additionally withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species.
Claim Objections
Claim 2 is objected to because of the following informalities:
Claim 2 is objected to for reciting ethanolamine twice (see lines 1-2 “amino alcohol is selected from…ethanolamine, ethanolamine…”. . It appears that ethanolamine is duplicated in the claim. It is suggested one recitation of ethanolamine be deleted.
Claim Rejections - 35 USC § 112a
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-2 and 6-13 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
The claims require and “oxazaborolidine”. The claims do not require that the oxazaborolidine possess any particular conserved structure, or other distinguishing feature. Therefore, the skilled artisan would not recognize that Applicants were in possession of the invention as broadly claimed at the time the application was filed. The full breadth of the claims fails to meet the written description provision of 35 U.S.C. §112, first paragraph.
To satisfy the written-description requirement, the specification must describe every element of the claimed invention in sufficient detail so that one of ordinary skill in the art would recognize that the inventor possessed the claimed invention at the time of filing. Vas-Cath, 935 F.3d at 1563; see also Lockwood v. American Airlines, Inc., 107 F.3d 1565, 1572 [41 USPQ2d 1961] (Fed. Cir. 1997) (patent specification must describe an invention and do so in sufficient detail that one skilled in the art can clearly conclude that “the inventor invented the claimed invention”); In re Gosteli, 872 F.2d 1008, 1012 [10 USPQ2d 1614] (Fed. Cir. 1989) (“the description must clearly allow persons of ordinary skill in the art to recognize that [the inventor] invented what is claimed”). Thus, an applicant complies with the written-description requirement “by describing the invention, with all its claimed limitations, not that which makes it obvious,” and by using “such descriptive means as words, structures, figures, diagrams, formulas, etc., that set forth the claimed invention.” Lockwood, 107 F.3d at 1572.
According to the MPEP §2163 I. A. “the issue of a lack of adequate written description may arise even for an original claim when an aspect of the claimed invention has not been described with sufficient particularity such that one skilled in the art would recognize that the applicant had possession of the claimed invention. The claimed invention as a whole may not be adequately described if the claims require an essential or critical feature which is not adequately described in the specification and which is not conventional in the art or known to one of ordinary skill in the art.” The MPEP states in §2163 II 3 ii) “The written description requirement for a claimed genus may be satisfied through sufficient description of a representative number of species by actual reduction to practice (see i)(A), above), reduction to drawings (see i)(B), above), or by disclosure of relevant, identifying characteristics, i.e., structure or other physical and/or chemical properties, by functional characteristics coupled with a known or disclosed correlation between function and structure, or by a combination of such identifying characteristics, sufficient to show the applicant was in possession of the claimed genus (see i)(C), above). See Eli Lilly, 119 F.3d at 1568, 43 USPQ2d at 1406.”
According to the MPEP §2163.02 Standard for Determining Compliance With the Written Description Requirement,
“The courts have described the essential question to be addressed in a description requirement issue in a variety of ways. An objective standard for determining compliance with the written description requirement is, “does the description clearly allow persons of ordinary skill in the art to recognize that he or she invented what is claimed". In re Gosteli, 872 F.2d 1008, 1012, 10 USPQ2d 1614, 1618 (Fed. Cir. 1989). Under Vas-Cath, Inc. v. Mahurkar, 935 F.2d 1555, 1563-64, 19 USPQ2d 1111, 1117 (Fed. Cir. 1991), to satisfy the written description requirement, an applicant must convey with reasonable clarity to those skilled in the art that, as of the filing date sought, he or she was in possession of the invention, and that the invention, in that context, is whatever is now claimed. The test for sufficiency of support in a parent application is whether the disclosure of the application relied upon “reasonably conveys to the artisan that the inventor had possession at that time of the later claimed subject matter". Ralston Purina Co. v. Far-Mar-Co., Inc., 772 F.2d 1570, 1575, 227 USPQ 177, 179 (Fed. Cir. 1985) (quoting In re Kaslow, 707 F.2d 1366, 1375, 217 USPQ 1089, 1096 (Fed. Cir. 1983)).”
Applicants are reminded of what the U.S. Court of Appeals Federal Circuit wrote in University of California v. Eli Lilly and Co. 43 USPQ2d 1398, "In claims involving chemical materials, generic formulae usually indicate with specificity what the generic claims encompass. One skilled in the art can distinguish such a formula from others and can identify many of the species that the claims encompass. Accordingly, such a formula is normally an adequate description of the claimed genus." "A definition by function, as we have previously indicated, does not suffice to define the genus because it is only an indication of what the gene does, rather than what it is.” See Fiers, 984 F.2d at 1169-71, 25 USPQ2d at 1605-06 (discussing Amgen). "It is only a definition of a useful result rather than a definition of what achieves that result." "The description requirement of the patent statute requires a description of an invention, not an indication of a result that one might achieve if one made that invention. See In re Wilder, 736 F.2d 1516, 1521, 222 USPQ 369, 372-73 (Fed. Cir. 1984) (affirming rejection because the specification does "little more than outlin[e] goals appellants hope the claimed invention achieves and the problems the invention will hopefully ameliorate.")".
Applicant is reminded that Vas-Cath makes clear that the written description provision of 35 U.S.C. §112 is severable from its enablement provision.
Applicant may overcome this rejection by amending the claims to include a chemical structure representing an oxazaborolidine of the claims. Applicant could, for instance, incorporate the structure of formula (I) which is set forth in claim 20.
Claim Rejections - 35 USC § 102
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.
Claim(s) 1-2 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Jabbour et al. (WO2005/021559 A2) (hereinafter “Jabbour”).
Jabbour teaches a process for producing an oxazaborolidine corresponding to 2-butyl-3, 4-dimethyl-5-phenyl-1,3,2-oxazaborolidine (page 16, compound BNO5; pictured below for convenience), the process comprising
reacting an amino alcohol with a boronic acid with the azeotropic removal of water to provide a mixture of the starting materials and an oxazaborolidine end product (see page 26, scheme 1, reaction of (-) ephedrine and an appropriate boronic acid with the azeotropic removal of water; see page 39, yield of BN05 is 72%; A reaction yield of 72% means that the reaction did not go to completion and there was starting material remaining); and
Isolating the product by distillation in high yield (see page 39). Jabbour teaches the compound was distilled (a common purification technique) with a reported yield. This is understood to mean they isolated only the product. Jabbour therefore meets the claim limitation of at least 75% purity.
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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.
Claim(s) 1 and 9-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Jabbour et al. (WO2005/021559 A2) (hereinafter “Jabbour”) in view of Ortiz-Marciales et al. (US 7,109,345 B1).
Jabbour teaches a process for producing an oxazaborolidine which was discussed in the above rejection of claims 1-2 under 35 USC § 102 and is incorporated herein by reference. Jabbour teaches the product is isolated by distillation (see page 39) which necessarily requires removal of any organic solvent from step (a). Jabbour additionally teaches the compound can be mixed with dichloromethane prior to isolation (page 27, second paragraph from bottom of page).
Jabbour is silent wherein the distillation is a vacuum distillation and the required distillation conditions. However, Ortiz-Marciales teaches 2-butyl-3, 4-dimethyl-5-phenyl-1,3,2-oxazaborolidine, which is the same oxazaborolidine disclosed in Jabbour, is obtained with high purity by vacuum distillation carried out at 0.7 mbar and 84⁰C (see Figure 4d; col 6, lines 35-40, oxazaborolidines have been obtained…with high purity (98%) as clear oils after vacuum distillation; Table 1, compound 4d, distillation occurred at 0.55 mmHg (~0.7 mbar) and 84 ⁰C).
The difference between the prior art and the instant claims is that the instant claims require vacuum distillation at least 100 ⁰C. However, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant application to purify the oxazaborolidine of Jabbour by vacuum distillation under the claimed conditions because it was already known that this oxazaborolidine could be distilled by vacuum distillation at 0.55 mmHg (~0.7 bar) and 84 ⁰C. It would have been routine to vary the temperature of distillation as a matter of optimizing the purification of the product. Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[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." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (Claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%.) See MPEP 2144.05.
One would have been motivated because Ortiz-Marciales taught that vacuum distillation resulted in an oxazaborolidine in high purity. One would have varied the temperature of distillation as a matter of finding the optimal distillation conditions.
One would have had a reasonable expectation of success because the oxazaborolidine disclosed by Jabbour was known to have been purified by vacuum distillation.
Claim(s) 1, 9 and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Jabbour et al. (WO2005/021559 A2) (hereinafter “Jabbour”) and Ortiz-Marciales et al. (US 7,109,345 B1) as applied to claim 1 and 9 above, and further in view of Graeve et al. (J Chemical Education 1964, Vol 41, No. 5) (hereinafter “Graeve”).
The teachings of Jabbour and Ortiz-Marciales were discussed above an are incorporated herein by reference. Jabbour and Ortiz-Marciales are silent regarding Kugelrohr vacuum distillation; however Graeve teaches Kugelrohr distillation is a simple vacuum distillation technique (column 1, Kugelrohr distillation apparatus). Graeve teaches distillations performed with a Kugelrohr apparatus are generally nearly quantitative, can be completed within 15-30 minutes, and high vacuum may be applied when dealing with sensitive compounds (column 2, final paragraph).
The difference between the prior art and the instant claims is that the instant claims require Kugelrohr vacuum distillation. However, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant application to modify the prior art references with a Kugelrohr distillation apparatus because Kugelrohr vacuum distillation was known to be simple and have beneficial effects (e.g. distillations are nearly quantitative and completed within 15-30 minutes).
One would have been motivated as a matter of purifying the greatest amount of product from the reaction in the least amount of time.
One would have had a reasonable expectation of success because Kugelrohr vacuum distillation was a known technique that could have been readily adapted to the method of Jabbour and Ortiz-Marciales.
Claim(s) 1 and 6-8 are rejected under 35 U.S.C. 103 as being unpatentable over Jabbour et al. (WO2005/021559 A2) (hereinafter “Jabbour”) in view of Desantis et al. (US5,866,719)(hereinafter “Desantis”).
Jabbour teaches a process for producing an oxazaborolidine which was discussed in the above rejection of claims 1-2 under 35 USC § 102 and is incorporated herein by reference. Jabbour is silent regarding wherein purification step (b) comprises dissolving a bicarboxylic acid in water and mixing this solution with the product of step (a) to precipitate out the starting material as a salt and produce an oxazaborolidine product filtrate. However, Desantis teaches a process for purifying an aminoalcohol wherein the aminoalcohol is mixed with oxalic acid and the resulting oxalate salt is crystallized (i.e. precipitated) from solution (Title, col 1, lines 65-67, col 2, lines 1-10). Desantis teaches the method comprises precipitation at temperatures ranging from -5 to 30 ⁰C, according to the solvent used (col 3, lines 20-25). Desantis teaches precipitation occurs in water (col 3, lines 15-20). Precipitation at an elevated temperature would involve wherein oxalic acid is heated. As a whole, Desantis teaches a method for isolating an aminoalcohol as an oxalate salt by precipitation.
The difference between the prior art and the instant claims is that the claims require removal (precipitation) of the starting material (an aminoalcohol) as a salt by combining the reaction mixture of step (a) with a bicarboxylic acid (oxalic acid), and optionally heating oxalic acid (bicarboxylic acid) to at least 40 ⁰C. However, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant application to remove the aminoalcohol starting material of Jabbour by precipitation with oxalic acid because at the time it was known that an aminoalcohol could be isolated from solution as a crystalline oxalate salt. A person of ordinary skill in the art would easily have recognized that the method of Desantis could be used as a means for isolating by precipitation and removing unwanted (unreacted) aminoalcohol starting material from the process disclosed by Jabbour. Moreover, it would have been routine to vary the temperature as a matter of optimizing precipitation and therefore removal of the starting material as the oxalate salt.
One would have been motivated as a matter of removing excess starting material from the reaction of Jabbour in order to facilitate purification of the oxazaborolidine product.
One would have had a reasonable expectation of success because at the time it was known that an aminoalcohol could be removed from solution by precipitation an oxalate salt.
Conclusion
No claim is allowed.
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May 29, 2026
/KEVIN S MARTIN/Examiner, Art Unit 1624
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