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 .
Priority
This application, filed on February 28, 2024, is a National Stage entry from International Application No. PCT/EP2022/073855, August 26, 2022, which claims priority under 35 U.S.C. 119 or 365 to the benefit of European Application No. EP21193759, filed on August 30, 2021. The certified copy of the foreign application has been received.
Response to Unity of Invention
Pursuant to the Remarks, filed on July 13, 2026, Applicant elects with traverse Group I encompassing claims 1-12.
Applicant asserts at least Groups I and III are considered a product and a process specially adapted for the manufacture of said product, and thus at least Groups I and III have unity of invention. This argument is unpersuasive because the compound of formula I is disclosed in WO2016023787, so formula I does not rise to the level of a special technical feature as required for unity. According to the PCT International Search and Preliminary Examination Guidelines: “Where a claim defines a product in terms of the process by which the product is made, the claim as a whole is directed to a product. Such a claim lacks novelty if a prior art product, even if made by an undisclosed process, appears to be inherently the same as, or indistinguishable from, the claimed invention.” (5.26). Thus, Group I will be examined on the merits and the restriction is final.
Status of Claims
Pursuant to the Remarks, filed on July 13, 2026, Applicant elects with traverse Group I encompassing claims 1-12.
Claims 1-14 are pending. Claims 1-12 are examined. Claims 13 and 14 are withdrawn.
Information Disclosure Statement
The information disclosure statement (IDS), filed on February 28, 2024, has been acknowledged and considered.
Specification Objections
Applicant is reminded of the proper language and format for an abstract of the disclosure.
The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, "The disclosure concerns," "The disclosure defined by this invention," "The disclosure describes," etc. In addition, the form and legal phraseology often used in patent claims, such as "means" and "said," should be avoided.
In the instant case, the abstract recites "said" in the 4th line, which is legal phraseology.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(a)
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 and 3-12 are rejected under 35 U.S.C. § 112(a) as failing to comply with the written description requirement. The claims contain subject matter that was not described in the Specification in such a way as to reasonably convey to one of ordinary skill in the art that Applicant, at the time the application was filed, had possession of the claimed invention.
In Ariad Pharm., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1351 (Fed. Cir. 2010) (en banc), the Federal Circuit stated “the hallmark of written description is disclosure.” A specification adequately describes an invention when it “reasonably conveys to those skilled in the art the inventor had possession of the claimed subject matter as of the filing date.” Id. “A ‘mere wish or plan’ for obtaining the claimed invention is not adequate written description.” Centocor Ortho Biotech, Inc. v. Abbott Labs., 636 F.3d 1341, 1348 (Fed. Cir. 2011). What is required to meet the written description requirement “varies with the nature and scope of the invention at issue, and with the scientific and technologic knowledge already in existence.” Capon v. Eshhar, 418 F.3d 1349, 1357 (Fed. Cir. 2005). In Ariad, the Federal Circuit explained what is required to
meet the written description requirement:
This inquiry, as we have long held, is a question of fact. Ralston Purina, 772 F.2d at 575. Thus, we have recognized that determining whether a patent complies with the written description requirement will necessarily vary depending on the context. Capon v. Eshhar, 418 F.3d 1349, 1357–58 (Fed. Cir. 2005). Specifically, the level of detail required to satisfy the written description requirement varies depending on the nature and scope of the claims and on the complexity and predictability of the relevant technology. Id. For generic claims, we have set forth a number of factors for evaluating the adequacy of the disclosure, including “the existing knowledge in the particular field, the extent and content of the prior art, the maturity of the science or technology, [and] the predictability of the aspect at issue.” Id. at 1359.
Further, the written description of a genus, such as a chemical genus, “requires a precise structure, formula, [or] chemical name” of the claimed subject matter sufficient to distinguish it from other materials. Regents of the Univ. of Cal. v. Eli Lilly & Co., 199 F.3d 1559, 1568 (Fed. Cir. 1997). The Federal Circuit commented on that case in the Ariad decision:
We held that a sufficient description of a genus instead requires the disclosure of either a representative number of species falling within the scope of the genus or structural features common to the members of the genus so that one of skill in the art can “visualize or recognize” the members of the genus. Id. At 1568-69. We explained that an adequate written description requires a precise definition, such as by structure, formula, chemical name, physical properties, or other properties, of species falling within the genus sufficient to distinguish the genus from other materials. Id. at 1568 (quoting Fiers v. Revel, 984 F.2d 1164, 1171 (Fed.Cir.1993)). We have also held that functional claim language can meet the written description requirement when the art has established a correlation between structure and function. See Enzo, 323 F.3d at 964 (quoting 66 Fed.Reg. 1099 (Jan. 5, 2001)). But merely drawing a fence around the outer limits of a purported genus is not an adequate substitute for describing a variety of materials constituting the genus and showing that one has invented a genus and not just a species.
The factors outlined in the above Federal Circuit cases are analyzed with respect to the claimed invention in turn below.
(A) The nature and scope of the claim invention in view of the specification: the claimed invention relates generally to the chemical art and more specifically to a process of preparing a compound of formula I by reacting a compound of formula II with hydroxylamine or its salt, a base, a chiral catalyst, and an organic solvent, wherein the base
is an anion exchange resin. The claimed phrase “anion exchange resin” encompasses a great range of commercially available exchangers.
The Specification provides one working example and a comparative example with all the same reagents except, base 1 is an anion exchange resin (solid form), and base 2 is sodium hydroxide 10% aqueous solution. There are no other anion exchange resins described.
(B) The extent and content of the prior art: The process of preparing compounds using ion-exchange resins as catalysts in organic synthesis is described in Gelbard et al., Ind. Eng. Chem. Res. 2005, 44, 8468-8498 (“Gelbard”) and Luqman et al., Ion Exchange Technology II: Applications, January 2012, Edition: 1, Publisher: Springer, UK (“Luqman”). Luqman states: “A great range of commercially available exchangers is available today, having their characteristics clearly described.” (p. 7, 1.2.4 Commercially Available Exchangers). Table 1.4 lists the names of commercially available anion exchangers compiled from the manufacturer’s booklets. Gelbard similarly teaches, by way of Table A1, commercially available anion exchange resins, specifically used for organic synthesis reactions (Abstract). Gelbard teaches, for example, an aldol reaction with the Rexyn 201 (HO-) resin to form α-hydroxyphosphonates (p. 8473, 1st col.) and a hydrolysis reaction with Anberlyst A-26 (HO-) resin to dibenzoylate glycosides and disaccharides to give free saccharides (p. 8479, 2nd col.).
Accordingly, while the prior art describes anion exchange resins used in organic synthesis reactions, it teaches different anion exchange resins are utilized for specific types of reactions.
(C) The maturity of the science or technology: while use of anion exchange resins as strong base resins exist for organic synthesis, different anion exchange resins are employed for different types of chemical reactions. As such, the science relevant to the claimed invention is mature insofar as the prior art has identified the advantages of using certain types of anion exchange resins for certain types of synthetic reactions.
(D) The predictability of the aspect at issue: the chemical art is generally recognized as unpredictable. The art requires each reaction be assessed by the yield of the product produced and the enantioselectivity achieved. The more unpredictable an area is the more specific disclosure is necessary to satisfy the statutory requirement.
When the above factors and evidence discussed therein are considered as a whole, the specification does not adequately describe a representative number of species to support the claimed genera of “anion exchange resins.” Accordingly, the Specification does not reasonably convey to those skilled in the art that the Applicant had possession of the claimed subject matter as of the filing date.
Examiner recommends amending claim 1 to include the type of anion exchange resin supported by the specification (i.e., claim 2). Claims 3-12 do not resolve the issue associated with claim 1 and are therefore rejected by virtue of their dependency.
Claim Rejections - 35 USC § 112(b)
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 5-6 and 8-10 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c),(d). In the present instance, claims 5-6 and 8-10 recite broad recitations: claims 5-6 and 9-10 recite a broad range [broadest range within the claim] of molar equivalents, followed by at least one narrow range and claim 8 recites a broad ratio of organic solvent:water, followed by a narrow range. The claims are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Appropriate correction is required.
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 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over WO2016023787 Cite No. 1 of Foreign Patent Documents in IDS filed February 28, 2024 (“Smejkal”) in view of Gelbard et al., Ind. Eng. Chem. Res. 2005, 44, 8468-8498 (“Gelbard”).
Smejkal teaches a procedure to prepare isomers of compound XXV, from compound XXIV,
PNG
media_image1.png
172
282
media_image1.png
Greyscale
. Compound XXIV was dissolved in dichloromethane, the mixture was further charged with a chiral catalyst, 10M sodium hydroxide solution, water, and 50% aqueous hydroxylamine, and at reacted -20°C for 20h (p.10). The chiral catalysts taught were XVII,
PNG
media_image2.png
292
359
media_image2.png
Greyscale
, and XIX,
PNG
media_image3.png
257
343
media_image3.png
Greyscale
(pp. 8 and 11; Table 1).
Smeljak does not teach using an anion exchange resin as the base.
Gelbrand teaches various reactions where a strong base resin is utilized: for example in 1) the synthesis of benzylideneacetone from acetone and benzaldehyde in a NaOH solution with a microporous tributylamine aminated strong base anion exchange resin, 2) the formation of α-hydroxyphosphonates from aldehydes giving yields up to 90% in the presence of Rexyn 201 (HO-) (p. 8473, 1st col.), 3) debenzoylating glycosides and disaccharides in the presence of Aberlyst A-26 (HO-) (p. 8479, 2nd col.), 4) formation of arylmethylenemalononitriles with yields up to 98% catalyzed by a strong base anion exchange resin in water, and 5) hydrolysis of alkylene oxides to form their respective alkylene glycols in the presence of a strong base exchange resin in the absence of CO2 (p. 8486, 1st col.).
Smeljak and Gelbrand are considered analogous art because they are in the same field of applying strong bases to improve the yield of the desired compound. Therefore, it would have been prima facie obvious to a person having ordinary skill in the art (PHOSITA), before the effective filing date of the claimed invention, to combine the teachings of the prior art elements to arrive at the process instantly claimed. It would have been prima facie obvious to prepare a compound XXV, by reacting compound XXIV, with hydroxylamine, a chiral catalyst, a base, and an organic solvent at temperatures of -20°C, based on the teachings of Smeljak, and substitute the base for a strong base anion exchange resin, based on the teachings of Gelbrand, because they are known equivalents utilized for the same purpose (MPEP §2144.06(II)). Furthermore, Gelbrand states, “the thermal stability of anion-exchange resins, especially when used in their (HO-) form, was improved by using resins with nonbenzylic quaternary ammonium groups such as 4-ammoniobutyl and pyrrolidinium.” (p. 8490, 2nd col.). It would have been prima facie obvious to a PHOSITA to substitute sodium hydroxide solution, for a strong base resin in its HO- form, because Smeljak implicitly teaches that the reaction is temperature sensitive by carrying it out at -20°C, and Gelbrand provides the motivation to use an anion-exchange resin, especially in its HO- form, because it is thermally stable. Accordingly, claims 1-3 are prima facie obvious.
Regarding claim 4, Gelbrand teaches the Ambersep 900/910 anion exchange resin as one of the strong base resin of choice for organic synthesis reactions, which has a styrene-dicinylbenzene matrix, evidenced by the MilliporeSigma product page (CAS:9017-79-2).
Regarding claim 5, Smeljak teaches the preferable base to carry out the reaction is sodium hydroxide, and is in the amount between 0.05 to 1.0 equivalents (p. 6, ll. 19-22).
Regarding claim 6, Smeljak teaches the organic solvent to be dichloromethane (DCM) at 4mL of volume. The density and molecular weight of DCM is 1.33
g
m
L
and 84.93
g
m
o
l
, respectively. Thus, the mass of DCM, based on the reaction conditions of Smeljak, is
4
m
L
x
1.33
g
m
L
=
5.32
g
. The mmol amount is
5.32
g
x
1
84.93
g
m
o
l
x
1000
=
62.6
m
m
o
l
.
This amount relative to the starting compound XXIV is
62.6
m
m
o
l
D
C
M
0.32
m
m
o
l
X
X
I
V
=
196
molar equivalents, which overlaps with the range instantly claimed (MPEP §2144.05(I)).
Regarding claims 7-8, Smeljak teaches water is present in a volume of 0.054mL. The ratio of DCM to water is thus 4:0.054 = 74.1 molar equivalents, overlapping with the range instantly claimed (MPEP §2144.05(I)).
Regarding claim 9, Smeljak teaches 0.64 mmol of 50% aqueous hydroxylamine was present in the reaction, which is 0.64:0.32=2 molar equivalents, overlapping with the range instant claim (MPEP §2144.05(I)).
Regarding claim 10, Smeljak teaches 0.06 mmol of chiral catalyst was present in the reaction, which is 0.06:0.32=0.1875 molar equivalents, overlapping with the range instantly claimed (MPEP §2144.05(I)).
Regarding claim 11, Smeljak teaches the reaction mixture was analyzed by chiral HPLC. It would have been prima facie obvious to a PHOSITA to isolate solid anion exchange resin from the reaction mixture, as a solid cannot be analyzed by HPLC.
Regarding claim 12, Smeljak teaches, in the last 4 entries of Table 1, the presence of the (5S,4R) isomer in a yield ranging from 90-94%, along with the (5S,4S), (5R,4S), and (5R,5R) isomers present in the mixture.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SAHIL CHANDER AGGARWAL whose telephone number is (571)272-7755. The examiner can normally be reached 7am-5pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Adam C Milligan can be reached at (571) 270-7674. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SAHIL CHANDER AGGARWAL/Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623
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