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
The instant application is a 371 National Stage Entry of PCT/EP2023/053410 filed on February 13, 2023 which claims priority to foreign application No. EP22156688.8 filed on February 15, 2022.
Status of Claims
Acknowledgement is made of original (1-2, 8-10, 19, 21), amended (3-7, 11-13, 15, 17-18, 20, 24-25), and cancelled (14, 16, 22-23, 26) claims filed on August 13, 2024. Claims 1-13, 15, 17-21, 24-25 are pending in instant application.
Information Disclosure Statement
The information disclosure statement filed on January 16, 2025 has been considered.
Claim Objections
Claim 25 objected to because of the following informalities:
Claim 25 recites “Cbz is carboxybenzyl/benzyloxycarbonyl”. The “/” appears to be a stand-in for “also known as”. For clarity purposes, it is recommended the claim simply read “Cbz is benzyloxycarbonyl”.
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.
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 1-13, 15, 17-21, 24-25 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.
Regarding claims 1-7, 15, 18-21, 25, and compounds A and C and claims 8-13, 17, 24 and compound D, in claims 1 and 8 the line-angle structures for compounds A, C, and D lack hydrogens or substituents on the relevant nitrogen atoms, appearing incomplete and differing from the structures in the specification (see instant spec. at p. 2 and 5). Accordingly, an artisan would not understand if they are generic formula or fully defined species, and if they are a fully defined species, what is attached to the nitrogens (e.g. hydrogen, alkyl, etc)? The dependent claims do not fully resolve this issue of indefiniteness and are included in instant rejection. For the purposes of applying art, compound A is understood to have an NH2 (as shown in claim 25),
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also known as CAS# 1249636-58-5, compound C is understood to have two NHs (see instant spec. at p. 2),
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also known as CAS# 2260969-36-4, and compound D is understood to have an NH2 (as shown in claim 24),
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also known as CAS# 63089-56-5.
Further regarding claim 10, the phrase "such as" (stated twice) renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Further regarding claim 15, the claim references “compound (D)” but no structure is given in the claim or in the claim from which it depends (claim 1). Accordingly, an artisan would not understand what compound (D) is. For the purposes of applying art, compound D is understood to be
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, also known as CAS# 63089-56-5 (see instant spec. at p. 5).
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) 8-10 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by WO 01/19390 A1 to Littman et. al.1
Regarding claim 8, Littman teaches a method of making 4-isocyanato-1,2,3,5,6,7-hexahydro-s-indacene, also known as CAS# 210827-31-9 reading on instant compound B, from 1,2,3,5,6,7-hexahydro-s-indacen-4-amine, also known as CAS# 63089-56-5 and reading on instant compound D (see Littman at pp. 84-85, Example 145).
Instant
Claim 8
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Example 145
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Regarding claims 9-10, Littman teaches converting CAS# 63089-56-5 with phosgene (compare with instant claim 9), triethylamine (reads on a base and tertiary amine, compare with instant claims 9-10), in tetrahydrofuran and toluene (reading on solvents, compare with instant claims 9-10) (see Littman at pp. 84-85).
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) 11-12 are rejected under 35 U.S.C. 103 as being unpatentable over Littman as applied to claims 8-10 above and in further view of Hoffman et. al.2
Regarding a solvent, Littman teaches tetrahydrofuran or toluene may be used as the solvent to make 1,2,3,5,6,7-hexahydro-5-indacen-4ylamine derivatives (see Littman at p. 82 lines 21-26 Example 138).
The prior art differs from the instant claims as follows: while Littman teaches a method of making CAS# 210827-31-9 from CAS# 63089-56-5 with triethylamine, Littman does not specify an alternative base.
However,
Regarding claims 11-12 and trimethylamine, Hoffman teaches trimethylamine, triethylamine, tri-n-butylamine, N,N-dimethylcyclohexylamine, N,N-diethylaniline, pyridine, and quinoline are tertiary amines known to be used with phosgene in the synthesis of isonitriles (see Hoffman at p. 11 “A. The Phosgene Method”).Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Regarding a base, per MPEP § 2144.07, a prima facie case of obviousness exists for the selection of a known material based on its suitability for its intended use. Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). It would have been obvious to one skilled in the art to substitute a known base (e.g. trimethylamine as taught by Hoffman) in a known method (e.g. triethylamine and phosgene in formation of CAS# 210827-31-9 as taught by Littman) because the prior art teaches bases compatible with a known reagent of the known reaction (e.g. trimethylamine and triethylamine are compatible bases with phosgene).
Regarding solvent, the prior art teaches a reaction comprising toluene and THF (as taught by Littman). It would have been obvious to an artisan to optimize the reaction by eliminating the need for a second solvent by attempting a reaction with just THF or just toluene with a reasonable expectation of success since the prior art teaches both are compatible as a mixture or alone for the reaction step (as taught by Littman).
Furthermore, it is well-within the ordinary skill in art to substitute one known base for another for the same purpose as taught by the prior art.
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Claim(s) 11-13 are rejected under 35 U.S.C. 103 as being unpatentable over Littman as applied to claims 8-10 above and in further view of Navarro et. al.3
Regarding a solvent, Littman teaches tetrahydrofuran or toluene may be used as the solvent to make 1,2,3,5,6,7-hexahydro-5-indacen-4ylamine derivatives (see Littman at p. 82 lines 21-26 Example 138).
The prior art differs from the instant claims as follows: while Littman teaches a method of making CAS# 210827-31-9 from CAS# 63089-56-5 with triethylamine, Littman does not specify an alternative base or toluene as the only solvent.
However,
Regarding claims 11-12 and trimethylamine, Navarro teaches N,N-diisopropylethylamine and triethylamine are both suitable tertiary amines for phosgenating reactions to form isocyanates from free amines (see Navarro at p. 5142 Scheme 1 “phosgenation” step and p. 5142 Table 1).
Regarding claims 12-13 and toluene, recall Littman teaches a solvent mixture of tetrahydrofuran and toluene (see Littman at pp. 84-85, Example 145).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Regarding a base, per MPEP § 2144.07, a prima facie case of obviousness exists for the selection of a known material based on its suitability for its intended use. Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). It would have been obvious to one skilled in the art to substitute a known base (e.g. N,N-diisopropylethylamine, as taught by Navarro) in a known method (e.g. triethylamine and phosgene in formation of CAS# 210827-31-9 as taught by Littman) because the prior art teaches bases compatible with a known reagent of the known reaction (e.g. N,N-diisopropylethylamine and triethylamine are compatible bases with phosgene).
Regarding solvent, the prior art teaches a reaction comprising toluene and THF (as taught by Littman). It would have been obvious to an artisan to optimize the reaction by eliminating the need for a second solvent by attempting a reaction with just THF or just toluene with a reasonable expectation of success since the prior art teaches both are compatible as a mixture or alone for the reaction step (as taught by Littman).
Furthermore, it is well-within the ordinary skill in art to i) substitute one known base for another for the same purpose as taught by the prior art or ii) modify a known reaction by eliminating a variable.
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Claim(s) 17 is rejected under 35 U.S.C. 103 as being unpatentable over Littman as applied to claims 8-10 above and in further view of Perlmutter et. al.4
The prior art differs from the instant claims as follows: while Littman teaches a method of making CAS# 210827-31-9 from CAS# 63089-56-5, Littman does not specify a continuous mode.
However,
Regarding a continuous mode, Perlmutter teaches “[t]he benefits of continuous versus batch chemical processes are well established - including higher product throughput and yield, lower space requirements and capital investment, faster product changeover, more consistent quality, and the ability to safely run reactions at more extreme conditions” (see Perlmutter at “Session Description”).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Per MPEP § 2143(I)(D), a prima facie case of obviousness exists for applying a known technique to a known method or product ready for improvement to yield predictable results. It would have been obvious to one of ordinary skill in the art to improve upon a known synthesis (as taught by Littman) with a known technique for improvement (as taught by Perlmutter) with a reasonable expectation of success because the prior art teaches continuous processing results in higher product yield and more consistent quality (as taught by Perlmutter).
Furthermore, it is well-within the ordinary skill in art to modify a known method with a known technique as taught by the prior art.
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Claim 24 is rejected under 35 U.S.C. 103 as being unpatentable over Littman as applied to claims 8-10 above and in view of WO 2020/079207 A1 to Schwizer et. al.5
Littman teaches syntheses of instant compound IX as shown in instant claim 24 (see Littman at p. Preparation PP).
Instant Claim 24
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Preparation PP
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Littman also teaches making instant compound X (CAS# 14927-64-1) from instant compound IX (CAS# 39105-39-0) (see Littman at p. Preparation QQ), but making instant D (CAS# 63089-56-5) from a different starting material (see Littman at p. Preparation VV).
Instant Claim 24
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Preparation QQ
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Preparation VV
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The prior art differs from the instant claims as follows: while Littman teaches a method of making instant compound IX (CAS# 39105-39-0), Littman does not specify wherein the method continues on to instant D (CAS# 63089-56-5) from instant X (CAS# 14927-64-1).
However,
Schwizer teaches making instant compound D (CAS# 63089-56-5) from instant compound X, as shown in instant claim 24 (CAS# 14927-64-1) (see Schwizer at p. 10).
Instant Claim 24
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Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Per MPEP § 2143(I)(D), a prima facie case of obviousness exists for applying a known technique to a known method or product ready for improvement to yield predictable results.
It would have been obvious to one skilled in the art to modify Littman’s syntheses of compounds X and D by substituting Schwizer’s synthesis of instant D for Littman’s synthesis of D with a reasonable expectation of success because it would streamline Littman’s synthesis to D from IX.
Furthermore, it is well-within the ordinary skill in art to modify one known synthesis with another known synthesis.
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Conclusion
Claim 25 is objected to.
Claims 1-13, 15, 17-21, 24-25 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SOPHIA J REILLY whose telephone number is (703)756-5669. The examiner can normally be reached 9:00 am - 5:00 pm EST M-F.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, KORTNEY KLINKEL can be reached at 571-270-5239. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/S.R./Examiner, Art Unit 1627
/JENNIFER A BERRIOS/ Primary Examiner, Art Unit 1613
1 Published March 22, 2001. Hereinafter Littman.
2 Hoffman et. al. Isonitrile Syntheses. In Isonitrile Chemistry; Ugi, I. Ed. Vol 20, Academic Press, 1971. Select Pages. Hereinafter Hoffman.
3 Navarro et. al. "General approach to prepare polymers bearing pendant isocyanate groups" Polym. Chem. 2020, 11, 5140. DOI: 10.1039/d0py00989j. Hereinafter Navarro.
4 Perlmutter et. al. "Transitioning from Batch to Continuous Processes" AIChE 2017 Process Development Symposium, June 7, 2017. Hyatt Regency Toronto, Canada. Hereinafter Perlmutter.
5 Published April 23, 2020 hereinafter Schwizer.
Prosecution Insights