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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 2026 January 6 of claim 1-17 has been entered.
The 35 U.S.C. 102(a)(2) and 103 rejections are overcome because the filed arguments show common ownership not later than the earliest effective filing date of the examined application.
Priority
Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216. Consequently the effective filing date of the examined application remains 2021 February 26 due to no certified translations of the two Korean priority documents being filed.
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Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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) 1-4, 7, 9, 10, and 12 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by KIM (WO 2020/045941, published 2020 March 5; equivalent US PGPub.20220064155, published 2022 March 3). US PGPub 20220064155 is employed as translation of WO 2020/045941becasue the documents are in the same family. Kim describes the synthetic conversion of compound 1-3 to compound 1-6 (WO 2020045941: page 22, line 1 to page 24, line 14; US 20220064155, page 9, paragraph [0176] to page 10, paragraph [0184]). Steps 1-4 through 1-6 (column 18, line 4 to column 19, line 45) anticipate the three steps of the specified claims for the following reasons: Kim describes a process of preparing compound 1-6 (page 21, line 13 to 25, line 6). Steps 1-4 through 1-6 of the process anticipate the specified claims above for the following reasons: intermediate 1-3 is the same compound as examined [chemical formula 1-1]; step 1-4 is performed with palladium acetate and cesium carbonate in which the ratio of intermediate 1-3 and 5-methyl-2-amine-thiazole is 1:1; in step 1-5, the reaction uses trifluoroacetic acid and the product is crystallized using ethyl acetate; and in step 1-6, the ratio of the intermediate to acrolyl chloride is 1:1, sodium bicarbonate is used as a base, and the reaction temperature is 0-10°C. Although the second reagent of step 1-4 is not drawn, it is presumed to be the same compound as [chemical formula 1-3) because the same product is formed.
Claim(s) 1-4, 7, 9, 10, and 12 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by KIM (KR 10-2019-0104641, published 2020 March 6; English translation of the same). Kim describes the synthetic conversion of compound 1-3 to compound 1-6 (page 136-35, paragraph [0242] to page 136-39, paragraph [0257]). Steps 1-4 through 1-6 anticipate the three steps of the specified claims for the following reasons: Kim describes a process of preparing compound 1-6. Steps 1-4 through 1-6 of the process anticipate the specified claims above for the following reasons: intermediate 1-3 is the same compound as examined [chemical formula 1-1]; step 1-4 is performed with palladium acetate and cesium carbonate in which the ratio of intermediate 1-3 and 5-methyl-2-amine-thiazole is 1:1; in step 1-5, the reaction uses trifluoroacetic acid and the product is crystallized using ethyl acetate; and in step 1-6, the ratio of the intermediate to acrolyl chloride is 1:1, sodium bicarbonate is used as a base, and the reaction temperature is 0-10°C. Although the second reagent of step 1-4 is not drawn, it is presumed to be the same compound as [chemical formula 1-3) because the same product is formed.
Claim(s) 1-4, 7, 9, 10, and 12 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by KIM (KR 10-2018-0100359, published 2020 March 6 or 2020 February 27; English translation of the same). Kim describes the synthetic conversion of compound 1-3 to compound 1-6 (page 101-29, paragraph [0164] to page 101-32, paragraph [0180]). Steps 1-4 through 1-anticipate the three steps of the specified claims for the following reasons: Kim describes a process of preparing compound 1-6. Steps 1-4 through 1-6 of the process anticipate the specified claims above for the following reasons: intermediate 1-3 is the same compound as examined [chemical formula 1-1]; step 1-4 is performed with palladium acetate and cesium carbonate in which the ratio of intermediate 1-3 and 5-methyl-2-amine-thiazole is 1:1; in step 1-5, the reaction uses trifluoroacetic acid and the product is crystallized using ethyl acetate; and in step 1-6, the ratio of the intermediate to acrolyl chloride is 1:1, sodium bicarbonate is used as a base, and the reaction temperature is 0-10°C. Although the second reagent of step 1-4 is not drawn, it is presumed to be the same compound as [chemical formula 1-3) because the same product is formed.
Although no official publication date of this document could be found internally, it is believed to be 2020 March 6 or 2020 February 27 due to the information below. Field (21) is Kim KR 10-201900104641. Field (30) is the presently cited document, filed 2018 August 27. Based on the idea that Korean applications are laid open at 18 months or earlier from time of filing, the publication date of KR 10-2018-0100359 is 2020 March 6 or 2020 February 27.
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Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103(a) which forms the basis for all obviousness rejections set forth in this Office action:
(a) A patent may not be obtained though the invention is not identically disclosed or described as set forth in section 102 of this title, if the differences between the subject matter sought to be patented and the prior art are such that the subject matter as a whole would have been obvious at the time the invention was made to a person having ordinary skill in the art to which said subject matter pertains. Patentability shall not be negatived by the manner in which the invention was made.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 103(a) 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.
Note that the list of rationales provided is not intended to be an all-inclusive list. Other rationales to support a conclusion of obviousness may be relied upon by Office personnel.
Claim 6 is rejected under 35 U.S.C. 103(a) as being unpatentable over KIM (WO 2020/045941, published 2020 March 5; equivalent US PGPub.20220064155, published 2022 March 3)..
Determining the scope and contents of the prior art
US PGPub 20220064155 is employed as translation of WO 2020/045941 because the documents are in the same family. Kim describes the synthetic conversion of compound 1-3 to compound 1-6 (WO 2020045941: page 22, line 1 to page 24, line 14; US 20220064155, page 9, paragraph [0176] to page 10, paragraph [0184]). Steps 1-4 through 1-6 (column 18, line 4 to column 19, line 45) anticipate the three steps of the specified claims for the following reasons: Kim describes a process of preparing compound 1-6 (page 21, line 13 to 25, line 6). Steps 1-4 through 1-6 of the process anticipate the specified claims above for the following reasons: intermediate 1-3 is the same compound as examined [chemical formula 1-1]; step 1-4 is performed with palladium acetate and cesium carbonate in which the ratio of intermediate 1-3 and 5-methyl-2-amine-thiazole is 1:1; in step 1-5, the reaction uses trifluoroacetic acid and the product is crystallized using ethyl acetate; and in step 1-6, the ratio of the intermediate to acrolyl chloride is 1:1, sodium bicarbonate is used as a base, and the reaction temperature is 0-10°C. Although the second reagent of step 1-4 is not drawn, it is presumed to be the same compound as [chemical formula 1-3) because the same product is formed.
Step 21-4 (WO 2020045941: page 43, lines 7-19; US 20220064155: page 18, paragraph [0264] to page 19, paragraph [0265]) describes that 6N HCl can be used to deprotect a Boc protected nitrogen.
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Ascertaining the differences between the prior art and the claims at issue
In the preparation of [chemical formula 1-4] in claim 6, hydrochloric acid is used.
Resolving the level of ordinary skill in the pertinent art
Those of relative skill in the art are those with level of skill of the authors of the references cited to support the examiner’s position (MD’s, PhD’s, or those with advanced degrees and the requisite experience in preparation of compounds of the elected group).
Considering objective evidence present in the application indicating obviousness or nonobviousness
Based on the combined teachings of Kim, there is a reasonable expectation of success that replacing HCl with F3C-C(O)-OH will facilitate the deprotection reaction to proceed to completion. The usage of both of these reagents suggest they are considered alternative methods of deprotecting a protect amine.
A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the foregoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103(a). From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Exemplary rationales that may support a conclusion of obviousness include:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
(E) “Obvious to try” – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
(F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
Claim 6 is rejected under 35 U.S.C. 103(a) as being unpatentable over KIM (KR 10-2019-0104641, published 2020 March 6; English translation of the same).
Determining the scope and contents of the prior art
Kim describes the synthetic conversion of compound 1-3 to compound 1-6 (page 136-35, paragraph [0242] to page 136-39, paragraph [0257]). Steps 1-4 through 1-6 (column 18, line 4 to column 19, line 45) anticipate the three steps of the specified claims for the following reasons: Kim describes a process of preparing compound 1-6 (page 21, line 13 to 25, line 6). Steps 1-4 through 1-6 of the process anticipate the specified claims above for the following reasons: intermediate 1-3 is the same compound as examined [chemical formula 1-1]; step 1-4 is performed with palladium acetate and cesium carbonate in which the ratio of intermediate 1-3 and 5-methyl-2-amine-thiazole is 1:1; in step 1-5, the reaction uses trifluoroacetic acid and the product is crystallized using ethyl acetate; and in step 1-6, the ratio of the intermediate to acrolyl chloride is 1:1, sodium bicarbonate is used as a base, and the reaction temperature is 0-10°C. Although the second reagent of step 1-4 is not drawn, it is presumed to be the same compound as [chemical formula 1-3) because the same product is formed. Step 21-4 (pages 136-63 to 136-64, paragraph [0403]) describes that 6N HCl can be used to deprotect a Boc protected nitrogen.
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Ascertaining the differences between the prior art and the claims at issue
In the preparation of [chemical formula 1-4] in claim 6, hydrochloric acid is used.
Resolving the level of ordinary skill in the pertinent art
Those of relative skill in the art are those with level of skill of the authors of the references cited to support the examiner’s position (MD’s, PhD’s, or those with advanced degrees and the requisite experience in preparation of compounds of the elected group).
Considering objective evidence present in the application indicating obviousness or nonobviousness
Based on the combined teachings of Kim, there is a reasonable expectation of success that replacing HCl with F3C-C(O)-OH will facilitate the deprotection reaction to proceed to completion. The usage of both of these reagents suggest they are considered alternative methods of deprotecting a protect amine.
A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the foregoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103(a). From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Claim 6 is rejected under 35 U.S.C. 103(a) as being unpatentable over KIM (KR 10-2018-0100359, published 2020 March 6 or 2020 February 27; English translation of the same).
Determining the scope and contents of the prior art
Kim describes the synthetic conversion of compound 1-3 to compound 1-6 (page 101-29, paragraph [0164] to page 101-32, paragraph [0180]). Steps 1-4 through 1-anticipate the three steps of the specified claims for the following reasons: Kim describes a process of preparing compound 1-6. Steps 1-4 through 1-6 of the process anticipate the specified claims above for the following reasons: intermediate 1-3 is the same compound as examined [chemical formula 1-1]; step 1-4 is performed with palladium acetate and cesium carbonate in which the ratio of intermediate 1-3 and 5-methyl-2-amine-thiazole is 1:1; in step 1-5, the reaction uses trifluoroacetic acid and the product is crystallized using ethyl acetate; and in step 1-6, the ratio of the intermediate to acrolyl chloride is 1:1, sodium bicarbonate is used as a base, and the reaction temperature is 0-10°C. Although the second reagent of step 1-4 is not drawn, it is presumed to be the same compound as [chemical formula 1-3) because the same product is formed.
Step 21-4 (page 101-56, paragraphs [0321]-[[0323]) describes that 6N HCl can be used to deprotect a Boc protected nitrogen.
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Although no official publication date of this document could be found internally, it is believed to be 2020 March 6 or 2020 February 27 due to the information below. Field (21) is Kim KR 10-201900104641. Field (30) is the presently cited document, filed 2018 August 27. Based on the idea that Korean applications are laid open at 18 months or earlier from time of filing, the publication date of KR 10-2018-0100359 is 2020 March 6 or 2020 February 27.
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Ascertaining the differences between the prior art and the claims at issue
In the preparation of [chemical formula 1-4] in claim 6, hydrochloric acid is used.
Resolving the level of ordinary skill in the pertinent art
Those of relative skill in the art are those with level of skill of the authors of the references cited to support the examiner’s position (MD’s, PhD’s, or those with advanced degrees and the requisite experience in preparation of compounds of the elected group).
Considering objective evidence present in the application indicating obviousness or nonobviousness
Based on the combined teachings of Kim, there is a reasonable expectation of success that replacing HCl with F3C-C(O)-OH will facilitate the deprotection reaction to proceed to completion. The usage of both of these reagents suggest they are considered alternative methods of deprotecting a protect amine.
A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the foregoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103(a). From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Response to Arguments
These rejections are made because the effective filing date remains 2021 February 26 due to the absence of certified translations of the Korean priority documents (see priority section). The 35 U.S.C. 102(b)(2)(c) exception does not apply against 35 U.S.C. 102(a)(1) prior art.
In each Kim rejection, the inventive entity contains four inventors that are not part of the examined inventive entity: Yeon Im Lee, Youn Jung Yoon, Keuk-Chan Bang, and Jaehyun Jung. Applicants have not shown that the four different inventors did not contribute to the examined invention.
Allowable Subject Matter
Claims 1-4, 6, 7, 9, 10, and 12 are not allowed.
Claims 5, 8, 11, and 13-17 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: KIM (WO 2020/045941, published 2020 March 5; equivalent US PGPub.20220064155, published 2022 March 3) does not describe or suggest the conditions recited in the steps 2 and 3 of the specified claims.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to NOBLE E JARRELL whose telephone number is (571)272-9077. The examiner can normally be reached 9:00 AM to 5:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Fereydoun Sajjadi can be reached at 571-272-3311. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/NOBLE E JARRELL/Primary Examiner, Art Unit 1699