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 .
Information Disclosure Statement
The information disclosure statement (IDS) submitted on Jan. 6, 2026 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Status
Claims 1-13, 16-18, 20, 24-27, 29-30, 32, 34, 40-41, 43, 45, and 52-53 are pending.
Applicant’s election without traverse of Group I, claims 1-13, 16-18, 20, 24-27, 29-30, 32 and 34, in the reply filed on Jan. 6, 2025 acknowledged.1
Claims 1-13, 16-18, 20, 24-27, 29-30, 32 and 34 are currently active and subject to examination. Claims 40-41, 43, 45, and 52-53 are withdrawn.
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.”
Claim 3 is 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 3 recites the limitation "the compound of formula… (K-1)" in line 2. There is insufficient antecedent basis for this limitation in the claim.
Claim Rejections – 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
“(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.”
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
“Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.”
Claim 10 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 10 does not further limit the method of claim 1 because it merely recites the natural consequence of the contacting (the mixture is formed in situ). Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claim(s) 1, 3-5, 7, 10-13, 16-18, 20, 24-27, 29-30, 32 and 34 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kincaid & Duncton (WO2018/213810 A1) (of record, cited in the last office action) in view of Nishikawa et al. (Organic Letters, Vol. 20, Issue 11, May 23, 2018, 3367-3371, Supporting Information (SI), p. S1-S124) and Barbion et al. (US 10,722,520 B2).
Claim 1 recites:
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Kincaid teaches a process for preparing a compound of formula (I) comprising contacting a compound of formula (K) with a compound of formula (II):
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Kincaid, Specification, p. 96.
Kincaid teaches that protecting groups can be used to protect an oxygen atom to prevent its further reaction for other purposes, and include trimethylsilyl (Kincaid, Specification, para. [0042]).
While Kincaid does not specifically teach contacting the compound of formula (K) with a first base and a silyating agent in a first solvent to form a first mixture comprising an O-silyl protected compound of formula (K), one of ordinary skill in the art would have a reasonable expectation of success to perform these steps to make an O-silyl protected compound of formula (K) because it is common practice in the art to use O-silyl protection during optimization of chemical reactions to increase reaction efficiency and avoid the creation of unwanted by products.
For example, Nishikawa teaches that a similar reaction can be carried out with the O-silyl protected form of an aminoalcohol which was first contacted with a base (triethylamine) and the silyating agent (chlorotrimethylsilane) in a first solvent to form an O-silyl protected aminoalcohol which is then reacted with an acetyl chloride compound:
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Nishikawa, SI, p. S6.
For example, Barbion teaches that a similar reaction can be carried out with the O-silyl protected form of aminooxyethanol which was first contacted with a base (N,N-dimethyl-4-aminopyridine: DMAP) and the silyating agent (tert-Butyldiphenylchlorosilane: TBDPSCI) in a first solvent to form an O-silyl protected aminooxyethanol which is then reacted with an carboxylic acid compound:
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Barbion, Specification, col. 129.
Therefore, claim 1 was prima facie obvious at the time of filing.
Claim 3 is directed towards the process of claim 1, wherein, prior to contacting with the silylating agent, the compound of formula (K) or (K-1) is first contacted with the first base in a first solvent. As shown in the rejection of claim 1, one of ordinary skill in the art would have a reasonable expectation of success to perform the reaction wherein prior to contacting with the silylating agent, the compound of formula (K) or (K-1) is first contacted with the first base in a first solvent, because it is commonly known in the art to contact compounds like formula (K) with a first base in a first solvent prior to contacting with the silylating agent. For example, see the teachings of Nishikawa. Therefore, claim 3 was prima facie obvious at the time of filing.
Claim 4 is directed towards the process of claim 1, wherein the silylating agent is timethylsilyl chloride. As shown in the rejection of claim 1, one of ordinary skill in the art would have a reasonable expectation of success to use timethylsilyl chloride (also known as: chlorotrimethylsilane) as the silylating agent because this silylating agent is commonly known in the art. For example, see the teachings of Nishikawa. Therefore, claim 4 was prima facie obvious at the time of filing.
Claim 5 is directed towards the process of claim 1, wherein the first base is a tertiary amine. As shown in the rejection of claim 1, one of ordinary skill in the art would have a reasonable expectation of success to use a tertiary amine as the first base because tertiary amines are commonly used in these reactions. For example, see Nishikawa teaching triethylamine and Barbion teaches DMAP. Therefore, claim 5 was prima facie obvious at the time of filing.
Claim 7 is directed towards the process of claim 1, wherein the first solvent comprises tetrahydrofuran (THF).
As shown in the rejection of claim 1, Kincaid and Nishikawa teach that the solvent is DCM.
One of ordinary skill in the art would have a reasonable expectation of success to use THF as the first solvent because it is a common organic solvent that is also compatible for the reaction to form the compound of formula (I).
For example, Kincaid teaches that the compound of formula (K) can also be contacted with THF prior to the reaction with the compound of formula (II):
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Kincaid, Specification, p. 86.
Therefore, claim 7 was prima facie obvious at the time of filing.
Claim 10 is directed towards the process of claim 1, wherein the first mixture is formed in situ. As shown in the rejection 1, one of ordinary skill in the art would have a reasonable expectation of success to carry out the reaction in situ because Nishikawa teaches that these reactions are formed in situ. This is just a natural consequence of the contacting. The mixture will be formed in the vessel in which the reagents are contacted. Therefore, claim 10 was prima facie obvious at the time of filing.
Claims 11 and 12 are directed towards the process of claim 1, wherein the second mixture further comprises a second solvent selected from THF. As shown in the rejection of claim 7, one of ordinary skill in the art would have a reasonable expectation of success to use THF as the second solvent because Kincaid teaches that the reaction can be carried out in THF. Therefore, claims 11-12 were prima facie obvious at the time of filing.
Claim 13 is directed towards the process of claim 1, wherein the second mixture is a slurry comprising a HCl salt of formula (II). One of ordinary skill in the art would have a reasonable expectation of success to use a slurry comprising a HCl salt of formula (II) because Kincaid teaches that the second mixture can be a slurry comprising a HCl salt of formula (K):
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Kincaid, Specification, p. 73.
Therefore, claim 13 was prima facie obvious at the time of filing.
Claim 16 recites:
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Kincaid teaches this reaction:
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Kincaid, Specification, p. 85.
Therefore, claim 16 was prima facie obvious at the time of filing.
Claim 17 is directed towards the method of claim 16, wherein the first chlorinating agent is thionyl chloride. As shown in the rejection of claim 16, Kincaid teaches thionyl chloride. Therefore, claim 17 was prima facie obvious at the time of filing.
Claim 18 is directed towards the process of claim 16, wherein the first chlorinating agent is present in an excess amount of at least 5 equivalents relative to the compound of formula (III). As shown in the rejection of claim 16, Kincaid teaches an excess amount of 10 equivalents. Therefore, claim 18 was prima facie obvious at the time of filing.
Claim 20 is directed towards the process of claim 16, wherein hydrogen chloride is present in an amount of from about 5 to about 6 equivalents to the compound of formula (III). As shown in the rejection of claim 16, Kincaid teaches that the compound of formula (III) is treated with a 4N solution of hydrogen chloride in 1,4-dioxane (14 mL, 5.35 mmol) which corresponds to an amount from about 5 to about 6 equivalents to the compound of formula (III). Therefore, claim 20 was prima facie obvious at the time of filing.
Claim 24 recites:
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Kincaid teaches this reaction:
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Kincaid, Specification, p. 94-95.
Therefore, claim 24 was prima facie obvious at the time of filing.
Claims 25-30, 32 and 34 read on the reaction as shown in the rejection of claim 24 (Kincaid, Specification, p. 94-95) and were therefore also prima facie obvious at the time of filing.
Claim(s) 1, 3-13, 16-18, 20, 24-27, 29-30, 32 and 34 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kincaid & Duncton (WO2018/213810 A1) (of record, cited in the last office action) in view of Nishikawa et al. (Organic Letters, Vol. 20, Issue 11, May 23, 2018, 3367-3371, Supporting Information (SI), p. S1-S124) and Barbion et al. (US 10,722,520 B2), as applied to claims 1, 3-5, 7, 10-13, 16-18, 20, 24-27, 29-30, 32 and 34 above, and further in view of Bedell et al. (US 7,115,632 B1).
The rejection of claims 1, 3-5, 7, 10-13, 16-18, 20, 24-27, 29-30, 32 and 34 above as obvious over Kincaid in view of Nishikawa and Barbion is incorporated herein by reference.
Claim 6 is directed towards the process of claim 5, wherein the tertiary amine is 4-methylmorpholine. As shown in the rejection of claim 5, while Nishikawa teaches the tertiary amine triethylamine and Barbion teaches the tertiary amine DMAP, one of ordinary skill in the art would have a reasonable expectation of success to substitute triethylamine with 4-methylmorpholine because these are recognized in the art as common equivalent bases in chemical reactions.
For example, Bedell teaches that suitable tertiary amines include triethylamine and 4-methylmorpholine (N-methylmorpholine):
In the case where an intermediate is a carboxylic acid, standard coupling reactions well known in the art can be used to form the compounds of this invention including protected intermediates. For example, the acid can be converted into an acid chloride, mixed anhydride or activated ester and reacted with an alcohol, amine, hydroxylamine or a protected hydroxylamine in the presence of base to form the amide, ester, hydroxamic acid, protected hydroxamic acid. This is the same product as discussed above. Bases are discussed above and include N-methyl-morpholine, triethylamine and the like.
Bedell, col. 245, lines 21-31.
Therefore, claim 6 was prima facie obvious at the time of filing.
Claim 8 is directed towards the process of claim 6, wherein a precipitate comprising a p-toluenesulfonic acid salt of 4-methylmorpholine is filtered prior to contacting the silylating agent. One of ordinary skill in the art would have a reasonable expectation of success to filter the solution prior to contacting with the silylating agent because the filtering of solutions to remove solids common practice in the art. For example, Kincaid teaches that intermediates are filtered prior to use in further chemical reactions (e.g. Kincaid, Specification, para. [0244], [0248]).
Therefore, claim 8 was prima facie obvious at the time of filing.
Claim 9 recites:
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Kincaid teaches a process for preparing the compound of formula (I) wherein the compound of formula (K) is present in an amount from about 1.1 to about 1.5 equivalents to the compound of formula (II) (1.61/1.07=1.50) :
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Kincaid, Specification, p. 85.
While Kincaid does not teach TMSCI, one of ordinary skill in the art would have a reasonable expectation of success to add TMSCI in an amount of 1.2 to about 2 equivalents relative to the compound of formula (II) because such amounts are generally known in the art.
For example, as shown in the rejection of claim 1 Nishikawa teaches that the reactants are present in an amount of about 15 mmol and the TMSCI is present in an amount of 16.5 mmol (16.5/15 = 1.1). The amount 1.1 is so similar to 1.2 to about 2 that one of ordinary skill in the art would expect similar results to be achieved by using this amount in this reaction.
As shown in the rejection of claim 1, Nishikawa teaches that the base triethylamine is present in an amount of about 2.5 equivalents (37.5/15) relative to the reactants. One of ordinary skill in the art would have a reasonable expectation of success to use about 3 to 5 equivalents of 4-methylmorpholine because 4-methylmorpholine is a common tertiary amine base that is used as an alternative for the tertiary amine triethylamine and because 2.5 equivalents is so similar to about 3 to 5 equivalents that one of ordinary skill would expect that similar results could be achieved using this amount in the reaction. For example, see the teachings of Bedell above in the rejection of claim 6 and the MPEP discussion of similar amounts and proportions:
Similarly, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 783, 227 USPQ 773, 779 (Fed. Cir. 1985) (Court held as proper a rejection of a claim directed to an alloy of "having 0.8% nickel, 0.3% molybdenum, up to 0.1% iron, balance titanium" as obvious over a reference disclosing alloys of 0.75% nickel, 0.25% molybdenum, balance titanium and 0.94% nickel, 0.31% molybdenum, balance titanium. "The proportions are so close that prima facie one skilled in the art would have expected them to have the same properties."). See also Warner-Jenkinson Co., Inc. v. Hilton Davis Chemical Co., 520 U.S. 17, 41 USPQ2d 1865 (1997) (under the doctrine of equivalents, a purification process using a pH of 5.0 could infringe a patented purification process requiring a pH of 6.0-9.0); 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%); In re Scherl, 156 F.2d 72, 74-75, 70 USPQ 204, 205-206 (CCPA 1946) (prior art showed an angle in a groove of up to 90° and an applicant claimed an angle of no less than 120°); In re Becket, 88 F.2d 684 (CCPA 1937) ("Where the component elements of alloys are the same, and where they approach so closely the same range of quantities as is here the case, it seems that there ought to be some noticeable difference in the qualities of the respective alloys."); In re Dreyfus, 73 F.2d 931, 934, 24 USPQ 52, 55 (CCPA 1934)(the prior art, which taught about 0.7:1 of alkali to water, renders unpatentable a claim that increased the proportion to at least 1:1 because there was no showing that the claimed proportions were critical); In re Lilienfeld, 67 F.2d 920, 924, 20 USPQ 53, 57 (CCPA 1933)(the prior art teaching an alkali cellulose containing minimal amounts of water, found by the Examiner to be in the 5-8% range, the claims sought to be patented were to an alkali cellulose with varying higher ranges of water (e.g., "not substantially less than 13%," "not substantially below 17%," and "between about 13[%] and 20%"); K-Swiss Inc. v. Glide N Lock GmbH, 567 Fed. App'x 906 (Fed. Cir. 2014)(reversing the Board's decision, in an appeal of an inter partes reexamination proceeding, that certain claims were not prima facie obvious due to non-overlapping ranges); In re Brandt, 886 F.3d 1171, 1177, 126 USPQ2d 1079, 1082 (Fed. Cir. 2018)(the court found a prima facie case of obviousness had been made in a predictable art wherein the claimed range of "less than 6 pounds per cubic feet" and the prior art range of "between 6 lbs./ft3 and 25 lbs./ft3" were so mathematically close that the difference between the claimed ranges was virtually negligible absent any showing of unexpected results or criticality.).
MPEP § 2144.05.
Therefore, claim 9 was prima facie obvious at the time of filing.
Claim(s) 1-5, 7, 10-13, 16-18, 20, 24-27, 29-30, 32 and 34 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kincaid & Duncton (WO2018/213810 A1) (of record, cited in the last office action) in view of Nishikawa et al. (Organic Letters, Vol. 20, Issue 11, May 23, 2018, 3367-3371, Supporting Information (SI), p. S1-S124) and Barbion et al. (US 10,722,520 B2), as applied to claims 1, 3-5, 7, 10-13, 16-18, 20, 24-27, 29-30, 32 and 34 above, and further in view of “2-Aminooxyethanol;4-methylbenzenesulfonic acid” (PubChem CID 21428455, SCHEMBL4202810, first published May 12, 2007, p. 1-9) (herein PubChem) (entry of record, IDS 03/04/2024, cite no. 9).
The rejection of claims 1, 3-5, 7, 10-13, 16-18, 20, 24-27, 29-30, 32 and 34 above as obvious over Kincaid in view of Nishikawa and Barbion is incorporated herein by reference.
Claim 2 is directed towards the process of claim 1, wherein the compound of formula (K) is a p-toluenesulfonic acid salt thereof represented by formula (K-1):
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While Kincaid does not teach the p-toluenesulfonic acid of the compound of formula (K) (the compound of formula (K-1)), one of ordinary skill in the art would have a reasonable expectation of success to employ the p-toluenesulfonic acid salt of the compound of formula (K) because it is commonly known solid form of the compound of formula (K).
For example, PubChem teaches the p-toluenesulfonic acid of the compound of formula (K) (the compound of formula (K-1)):
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PubChem, p. 2;
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PubChem, p. 1.
Therefore, claim 2 was prima facie obvious at the time of filing.
Given the above teachings, the invention as a whole was prima facie obvious at the time of filing.
Conclusion
No claim is found to be allowable.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to HEATHER DAHLIN whose telephone number is (571)270-0436. The examiner can normally be reached 9-5.
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/HEATHER DAHLIN/Examiner, Art Unit 1629
1 Applicant is reminded that upon the cancelation of claims to a non-elected invention, the inventorship must be corrected in compliance with 37 CFR 1.48(a) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. A request to correct inventorship under 37 CFR 1.48(a) must be accompanied by an application data sheet in accordance with 37 CFR 1.76 that identifies each inventor by his or her legal name and by the processing fee required under 37 CFR 1.17(i).