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 .
DETAILED ACTION
Claims 1-20 of D. Jacoby, et al., US 18/711,332 (05/17/2024) are pending and are under examination on merits. Claims 1, 9-11, 14-15, 17 and 19-20 are rejected, claims 2-8, 12-13, 16 and 18 are objected to.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Rejections - 35 USC § 112
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.
Claim 17 is rejected under 35 U.S.C. 112(b) as being indefinite because the claim recites the limitation "R" . There is insufficient antecedent basis for this limitation in the claim because the instant claim 1 does not recite the term of “R”. Herein, it is interpreted as “R1 is a hydrogen atom, a phenyl group or a C1-3 alkyl group” for purpose of compact prosecution.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1, 9-11, 17 and 19-20 are rejected under 35 U.S.C. 102 (a)(1) as being anticipated by W-Y. Lee, et al. 12.1 Bulletin of the Korean chemical society 31-35 (1991)(“Lee”)1 evidenced with the ThermoFisher and the ChemSrc.
Lee teaches a method for preparation of ethyl 2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxylate (10) by reacting of ethyl 2,6,6,-trimethyl-4-acetoxy-2-cyclohexene-1 carboxylate (9) with DBU. Lee at page 34, left col. the last second paragraph, β-Safranate (10), line 1-9.
The Lee method can be schematic summarized as indicated below.
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700
1801
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Lee at page 32, right col. Scheme 3. 9 to 10
The Lee compound 10 and the Lee compound 9 maps the formula (I) and the formula (II) in claim 1 respectively as:
n is 1,
each of R1, R4 and R5 is methyl that is a C1 alkyl,
each of R2 and R3 is hydrogen atom,
X is COOR6, wherein, R6 is ethyl that is a C2 alkyl, and
R7 is methyl that is a C1 alkyl.
The evidence from the ChemSrc indicates that the boiling point of ethyl 2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxylate is 246.8ºC (See ChemSrc at page 1, boiling point), and the evidence from the ThermoFisher indicates that the boiling point of DBU is 261ºC (See ThermoFisher at page 4/9,9. Physical and chemical properties, boiling point).
Thus, the Lee method meets each and every limitation of claim 1, 9-11, 17 and 19-20,therefore, claims 1, 9-11, 17 and 19-20 are anticipated.
Claims 14-15 are rejected under 35 U.S.C. 102 (a)(1)(a)(2) as being anticipated by T. Granier, et al, WO2008151455A12.
Granier teaches a compound ethyl 7-methylspiro[4 .5]deca-6 ,8-diene-6-carboxylate, and a compound of ethyl 9-acetoxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate, which has a chemical structure respectively as indicated below. Granier at page 49, paragraph 2. b).ethyl 7-methylspiro[4 .5]deca-6 ,8-diene-6-carboxylate.
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498
1658
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The Granier compound ethyl 9-acetoxy-7-methylspiro[4.5]dec-7-ene-6-carboxylate maps the formula (II”) in claim 14 as:
each of R1 and R7 is methyl that is a C1 alkyl,
each of R2 and R3 is hydrogen atom,
R4 and R5 are taken together with the atom to which they are attached to form a C5 cycloalkyl group, and
X is COOR6, wherein, R6 is ethyl that is a C2 alkyl.
Which meets each and every limitation of claim 14, therefore, claim 14 is anticipated.
The Granier compound ethyl 7-methylspiro[4 .5]deca-6 ,8-diene-6-carboxylate maps the formula (I”) in claim 15 as:
R1 is methyl that is a C1 alkyl,
each of R2 and R3 is hydrogen atom,
R4 and R5 are taken together with the atom to which they are attached to form a C5 cycloalkyl group, and
X is COOR6, wherein, R6 is ethyl that is a C2 alkyl.
Which meets each and every limitation of claim 15, therefore, claim 15 is anticipated.
Allowable Subject Matter
Claims 2-8, 12-13, 16 and 18 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.
As detail discussed in the 102 rejection above that Lee teaches a method meeting each and every limitation of claim 1.
The Lee method differs from claims 2-8, 16 and 18 in that the base used in the Lee method is DBU rather than the claimed metal salts.
The Lee method differs from claim 12 in that Lee does not teach to continuously remove of the product (10) during the reaction process.
The Lee method differs from claim 13 in that Lee does not teach to conduct the reaction in the presence of at least one aprotic dipolar solvent.
Claim 2-8, 16 and 18 are not obvious because one ordinary skill is not motivated to further modify the Lee method by replacing DBU with a claimed metal carboxylate, metal bicarbonate or metal carbonate. Motivation lacks because Lee teaches that the DBU used in the preparation of ethyl 2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxylate (10) cannot be taken place by other base such as t-BuOk, Et3N, 2,6-lutidine. Lee at page 33, left col., paragraph 2, line 11-13. Therefore, there is no a reasonable expectation of success to replace DBU used in the Lee method with a metal salt. A reasonable expectation of success is require for an obviousness rejection. MPEP2143.02
Claims 12-13 are not obvious because neither Lee nor Lee in view a second art to provide a guidance to motivate one ordinary skill in the art to further modify the Lee method by add at least one aprotic dipolar solvent to the reaction mixture or continuously remove of the product (10) during the reaction process.
Conclusion
Claims 1, 9-11, 14-15, 17 and 19-20 are rejected, claims 2-8, 12-13, 16 and 18 are objected to.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 cited by Applicant in the IDS form filed on 09/03/2026
2 cited by Applicant in the IDS form filed on 09/03/2026
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