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 .
Status of the Claims
Claims 1-5 are pending. Claims 1-5 are rejected.
Priority
This application claims foreign priority under 35 U.S.C. 119(a-d) to IN 2022/21038870, filed 07/06/2022. Receipt is acknowledged of papers submitted under 35 U.S.C. 119(a)-(d), which papers have been placed of record in the file.
Specification
The specification is objected to for numerous illegible structures. For instance, the following structures/schemes should be replaced with higher resolution images for legibility: Formula V on page 2, line 1 and page 4, line 1; compound (III) on page 5, line 6; scheme 1 on page 6, lines 14-15; the scheme on page 8, line 1; the scheme on page 8, line 14; the scheme on page 9, line 7; scheme 2 on page 9, line 19; scheme 3 on page 10, line 18; the scheme on page 10, line 26 (particularly the placement of the addition sign); and the scheme on page 11, line 4.
Claim Objections
Claims 1-3 are objected to because of the following informalities:
Claim 1 is objected to for numerous illegible structures. Specifically, compounds (1) and KSM-1 in page 1, line 8; compounds (3) and (5) in page 1, line 12 (particularly the placement of the addition sign next to compound (3)); compounds (6) and KSM-II in page 1, line 18; the scheme in page 2, line 1; the scheme in page 2, line 9; and the scheme in page 2, line 15.
Claim 1, line 2: delete “which”
Claim 1, line 6: insert a hyphen in the name: “(1H-1,2,4-triazol-1-yl)”
Claim 1, step d), line 1: insert a hyphen in the name: “(1H-1,2,4-triazol-1-yl)”
Claim 2 is objected to for being written in improper Markush format. Delete the first “and” in line 6. See MPEP § 2173.05(h).
Claim 3 should be amended to only one sentence such that the entire claim “begins with a capital letter and ends with a period” with no other periods in the claim. See MPEP § 608.01(m).
Appropriate correction is required.
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.
Claims 1-5 are rejected under 35 U.S.C. 112(b) being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 1 contains a compound name that may not be adequately understood by a person having ordinary skill in the art. The name, located first in step e), lines 4-6 and second in step f) lines 1-3, is “1-I[N-Methyl-N-2-(t-butoxycarbonylisopropylamino-methyl)phenyl] carbamoyloxyethyl-1-{(2R,3R)-2-(2,5-difluoropheny)-2-hydroxy-3-14-(4-cyano-phenyl)thiazol-2-y1butyl]- IH-|1,2,4) triazol-4-ium chloride (IV)”. Applicant may overcome the rejection by amending the name to a proper IUPAC name.
Dependent claims 2-5 are rejected as indefinite for the same reason since they do not correct the indefiniteness issue of their parent claims.
Claim 1 contains the trade names Diaion SA10A and Diaion PA308. Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe an anion exchange resin and, accordingly, the identification/description is indefinite.
Dependent claims 2-5 are rejected as indefinite for the same reason since they do not correct the indefiniteness issue of their parent claims.
Claim 2 recites the “process as claimed in claim 1, wherein the suitable solvent used in step a) to step f)…”, however claim 1 does not recite the use of a “suitable solvent” in steps e) or f). Therefore, there is insufficient antecedent basis for this limitation in the claim. Applicant may overcome the rejection by amending “step f)” in line 1 to “step d)”.
Regarding claim 3, the phrases “and the like” and “preferably” renders the claim indefinite because the claim includes elements not actually disclosed, thereby rendering the scope of the claim unascertainable. See MPEP § 2173.05(d). Applicant may overcome the rejection by deleting “and the like, preferably” and the remaining text thereafter.
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 5 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 5 recites limitations wherein the iodide salt of claim 1 may be potassium iodate or sodium iodate. However, a person having ordinary skill in the art would not be of the understanding that an “iodate” salt is a type of “iodide”. Thus, claim 5 does not properly limit claim 1 when attempting to include potassium iodate and sodium iodate as iodide salts.
Applicant may overcome the rejection by deleting the limitations potassium iodate and sodium iodate.
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 1-5 are rejected under 35 U.S.C. 103 as being unpatentable over Cui et al. in CN 110551064 A, published December 10, 2019 in view of An et al. in US 2023/0075632 A1, which was filed December 21, 2020 in US Application 17/789,095.
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Cui et al. teach a method of preparing isavuconazonium sulfate including the following six steps (see pages 2 and 3):
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.
In step (1) wherein compound C1 is synthesized, Cui et al. teach that DMAP and EDC are used in the reaction (see last line of page 28) and that the solvents are tetrahydrofuran (THF) and dichloromethane (DCM), see page 29, seventh paragraph. DMAP and EDC are the commonly known organic base 4,4-dimethylaminopyridine and coupling agent 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.
In step (2) wherein compound C2 is synthesized, Cui et al. teach that the reaction is performed with 1-chloroethylchloroformate in the presence of an alkali metal carbonate (see first paragraph of page 29) and the prior art further provides sodium carbonate, potassium carbonate, and lithium carbonate as examples of alkali metal carbonates (see first paragraph of page 31). Cui et al. also teach that DCM is used as a solvent in synthesis of C2, see page 35, line 6.
In step (3) wherein compound A3 is synthesized, Cui et al. teach that triethylamine is used in the reaction with a solvent of ethanol, see second to last paragraph of page 34.
In step (4) wherein compound A4 is synthesized from A3 and C2, Cui et al. teach that sodium bromide is used in the reaction with a solvent of acetonitrile, see Example 3 “Synthesis of A4” section in the middle of page 35.
In step (5) wherein compound A5 is synthesized, Cui et al. teach that HCl is used in the reaction with the ester solvent ethyl acetate, see last paragraph of page 35.
Lastly, in step (6) wherein the final compound A6 is prepared, Cui et al. teach that the final product is obtained through ion exchange reaction, see paragraph 5, page 29.
An et al. teach the synthesis of the instantly claimed step d) using sodium iodide as a reactant:
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, see bottom of page 1.
Ascertaining the differences between the prior art and the claims at issue. (See MPEP § 2141.02)
Cui et al. teach the use of a bromide salt in step 4, whereas the present invention claims use of an iodide salt in the comparable present step d).
Considering objective evidence present in the application indicating obviousness or nonobviousness. (See MPEP § 2142-2144)
Five of the six steps for synthesizing isavuconazonium sulfate taught by Cui et al. are identical to the synthesis in the instant claims wherein
step (1) of Cui is instant step b);
step (2) of Cui is instant step c);
step (3) of Cui is instant step a);
step (5) of Cui is instant step e); and
step (6) of Cui is instant step f).
Regarding step (4), which is nearly identical to instant step d), Cui discusses the problem of a difficult to remove impurity obtained when sodium iodide or potassium iodide is used as a reagent, requiring column chromatography as a purification method which results in lower reaction yields. See page 27, second paragraph. Note that this synthesis corresponds to the preparation of the iodide salt (III) of instant claim 1 in step d).
An et al. describe the synthesis of the same reaction intermediate (presently claimed compound (III) of step d)):
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, see bottom of page 1. They also identify the same problem discussed by Cui et al. wherein the above reaction produces poor purity and low reaction yields due to the need to purify via column chromatography on page 2:
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An et al. solve this problem by employing a synthetic strategy that purifies the intermediate with washing, without requiring a column chromatography purification. See page 14, paragraphs [0157]-[0158]:
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. This process results in a yield of 93.7% and purity of 95.6%.
A person having ordinary skill in the art would be motivated to incorporate the reaction using sodium iodide and purification process presented by An et al. in the overall synthesis of isavuconazonium sulfate because it results in a higher reaction yield than using sodium bromide and the purification process presented by Cui et al. (yield = 89.2%, see page 35, Example 3, “Synthesis of A4” section.)
Therefore, claim 1 is obvious in view of the prior art.
Regarding claim 2, Cui et al. teach the use of DCM as a solvent in steps (1) and (2), which correspond to instantly claimed steps b) and c). Additionally, Cui et al. teach the use of:
ethanol as a solvent in the step (3), which corresponds to instantly claimed step a); and
acetonitrile as a solvent in step (4), which corresponds to instantly claimed step d).
Regarding claim 3, Cui et al. teach the use of:
DMAP in step (1), which corresponds to instantly claimed step b);
alkali metal carbonate with specific examples sodium carbonate, potassium carbonate, and lithium carbonate in step (2), which corresponds to instantly claimed step c); and
triethylamine in step (3), which corresponds to instantly claimed step a).
Regarding claim 4, Cui et al. teach the use of coupling reagent EDC in step (1), which corresponds to instantly claimed step b).
Regarding claim 5, An et al. teach the use of sodium iodide in the reaction that corresponds with instantly claimed step d).
Therefore, claims 2-5 are obvious in view of the prior art.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jalisa H. Ferguson whose telephone number is (703)756-1489. The examiner can normally be reached Monday - Friday 9:00am - 5:00pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Joseph McKane can be reached on (571) 272-0699. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/J.H.F./Examiner, Art Unit 1626
/JOSEPH K MCKANE/Supervisory Patent Examiner, Art Unit 1626