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 .
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) 30- 32, 34-35, 37, and 43 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Leitch, Eur. J. Inorg. Chem. 2009, 2691-2701.
Leitch teaches group 4 metals, titanium and zirconium, chelated with amidate ligands (abstract). Leitch teaches
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where Ar is 2,6-dimethylphenyl (Scheme 2, pg. 2696). This meets claimed formulas I(a) and II(a) when M is titanium, R1 is N(R2)2, R2 is a C3 alkyl, y is 2, x is 2, a is 1, R5 is 2,6-dimethylphenyl (a substituted aryl), R6 and R7 are C3 alkyl groups.
This meets claims 30, 31, 32, 34, 35, 37, and 43.
Claim(s) 30-32, 34, 37, 41-43 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ivanov (US 2012/0045589).
Ivanov teaches the compound
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(¶31). This meets claimed formulas I(a) and II(a) when M is titanium, R1 is N(R2)2, R2 is a C1 alkyl, y is 2, x is 2, a is 1, R5 is t-butyl (a C4 alkyl), R6 and R7 are t-butyl (a C4 alkyl).
This meets claims 30, 31, 32, 34, 37, 41-43.
Claim(s) 30-31, 34, 37-38 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Pothiraja, Chem. Commun., 2009, 1978-1980.
Pothiraja teaches
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(Scheme 1). This meets claimed formulas I(a) and II(a) when M is hafnium, y is 0, x is 4, a is 1, R5 is iPr (a C3 alkyl), R6 is Me and R7 is Et (C1 and C2 alkyl groups).
Claim(s) 30, 32-34, 37, 41-42 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Leitch, J. Am. Chem. Soc. 2009, 131, 18246-18247.
Leitch teaches the compound
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(pg. 18246). This meets claimed formulas I(a) and II(a) when M is zirconium, R1 is N(R2)2, R2 is a C1 alkyl, y is 2, x is 1, a is 2, R5 is a C5 alkylene, R6 and R7 are iPr (a C3 alkyl).
Claim(s) 30-36 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Leitch, Organometallics, 2010, 29, 5162-5172.
Leitch teaches the compounds
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(Scheme 1) and
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(pg. 5165).
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meets claimed formulas I(a) and II(a) when M is zirconium, R1 is CH2Ph (an alkylene aryl), y is 2, x is 2, a is 1, R5 is a diisopropylphenyl group, R6 and R7 are bonded together to form a heterocycle.
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meets claimed formulas I(a) and II(a) when M is zirconium, R1 is CH2Ph (an alkylene aryl), y is 2, x is 1, a is 2, R5 is a C5 alkylene, R6 and R7 are iPr (a C3 alkyl).
Allowable Subject Matter
Claim 1 is allowed.
Claim 39-40 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.
Claim 1 recites a method of hydroaminoalkylation in the presence of the catalyst of formula (I).
Claims 39-40 recite the compound of claim 30 where R6 and R7 are a C1-6 alkyl and C1-4alkyene-aryl (claim 39) and where R6 and R7 are methyl and -CH(CH3)-phenyl.
Relevant prior art includes Bahena, J. Am. Chem. Soc. 2020, 142, 20566-20571; Leitch, Eur. J. Inorg. Chem. 2009, 2691-2701; Ivanov (US 2012/0045589); Pothiraja, Chem. Commun., 2009, 1978-1980; Leitch, J. Am. Chem. Soc. 2009, 131, 18246-18247; Leitch, Organometallics, 2010, 29, 5162-5172; Bielefeld, Angew. Chem. Int. Ed. 2017, 56, 15155-15158; Kubiak, Angew. Chem. Int. Ed., 2009, 48, 1153-1156; and Koperniku, J. Am. Chem. Soc., 2019, 141, 18944-18948.
Bahena teaches the hydroaminoalkylation of alkynes using a zirconium catalyst and a
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ligand (abstract, pg. 20566). Behena teaches the hydroaminoalkylation of alkynes. An alkyne falls outside the scope of an olefin, which is a carbon carbon double bond.
Bielefeld teaches hydroaminoalkylation using a titanium catalyst. Bielfefeld falls outside the scope of the instant claims because Bielefeld fails to use the claimed catalyst ligand.
Kubiak teaches hydroaminoalkylation using a titanium catalyst. Kubiak falls outside the scope of the instant claims because Kubiak fails to use the claimed catalyst ligand.
Koperniku teaches hydroaminoalkylation using a tantalum, titanium, or zirconium catalyst. Koperniku falls outside the scope of the instant claims because Koperniku fails to use the claimed catalyst ligand.
The above references fail to teach a catalyst having an ureate group having two different substituents on the nitrogen where one is an alkyl group and the other is an alkylene-aryl group as required by claims 39-40.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT C BOYLE whose telephone number is (571)270-7347. The examiner can normally be reached Monday-Thursday, 10am-4pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Arrie (Lanee) Reuther can be reached at (571)270-7026. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ROBERT C BOYLE/Primary Examiner, Art Unit 1764 (