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 .
In view of amendments to claims, pending claims 1-20 are examined together.
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) 1 and 2 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yu, CN108484426.
Yu teaches at page 1/3 teach
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X = aromatic, Phenylene
‘ammonium salt’
The presence of base
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and acid
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together is anticipated to make
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by acid-base reaction!
Claim Rejections - 35 USC § 103/102
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.
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.
Claim(s) 1-20 is/are rejected under 35 U.S.C. 102(a)(1)) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Sheng JACS Au (2021), 1(4), 501-507 (April 7 2021) in view of Lancien, Chem.Cat. Chem (2021), 13(1), 247-259.
Sheng teaches Calcium Phosphide for Reductive Amination of Carbonyl Compounds. At page 504 and 505 Schemes 1-3 in Sheng provides multiple examples of the fantastic chemistry which includes the Reaction Conditions (process parameters). The Reaction Conditions of Sheng include the possibilities of the limitations (process parameters such as solvent) of the instant claims 1-3, 5-20.
The difference is the presence of
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(as in the instant formulae). More specifically, Sheng teaches that the X of the instant formulae with a variety of substituents, present in the starting material (and in the product) are unaffected by the Reaction Conditions of solvent, temperature (as limited by the instant dependent claims). The Examples include the instant furan as in claim 4, see Scheme 1 three furan compounds.
Thus the substituents on X of the formulae play a spectator role with respect to Calcium Phosphide and the said Reaction Conditions.
Sheng is silent with respect to
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as substituent. At page 503, column B, Sheng teaches that ‘.various functional groups, such as halogen, methoxy, amide, and boronic ester moieties, were tolerant under these reaction conditions, providing the corresponding primary amines in excellent yields’.
Since substituent do not participate in the desired reaction, as exemplified by Sheng, one of skill in the art would have reasonable expectation of success in arriving at the limitations of instant claim 4, by starting with known starting material Formula (1-1) to make known product (2-1) using the chemistry of Sheng. For motivation see Lancien. According to Lancien, making the valuable 2-1 is a challenge, see page 248, column A second full paragraph.
Accordingly, the claims do not recite an unobvious distinction over the prior art. Further, a reference is relevant not only for what it expressly teaches, but also for what it would have conveyed to one of ordinary skill in the art. See In re Opprecht, 12 USPQ2d 1235, 1236 (Fed. Cir. 1989); In re Bode, 193 USPQ 12 (CCPA 1976). In light of the foregoing discussion, the Examiner finds that the claimed subject matter as a whole would have been obvious to one of ordinary skill in the art at the time the invention was made, in view of the cited references and the knowledge generally available in the art. Accordingly, the claims are rejected under 35 U.S.C. § 103.
Prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Afanasyev, Reductive Amination in the Synthesis of Pharmaceuticals, Chem.Rev.2019,119,11857−11911.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to NIZAL S CHANDRAKUMAR whose telephone number is (571)272-6202. The examiner can normally be reached M-F 8-5 EST.
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/NIZAL S CHANDRAKUMAR/Primary Examiner, Art Unit 1625
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