DETAILED ACTION
Pending Claims
Claims 1-15 are pending.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
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 .
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim Objections
Claims 8 and 11-14 are objected to because of the following informalities:
In claim 8, “the the formula (X)” should be replaced with: the formula (X).
In claim 11, the claim should conclude with a period. Claims 12-14 are objected to because they are dependent from claim 11.
In claim 12, “1:1’000” should be replaced with: 1:1,000.
Appropriate correction is required.
Claim Rejections - 35 USC § 112, 2nd paragraph (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.
Claims 2, 3, 5, 7, 8, and 12 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance:
claim 2 recites the broad recitation “wherein R11 is a C1-15-alkyl or a fluorinated C1-15-alkyl or a C7-15-cycloalkyl or a C7-15 -aralkyl group”, and the claim also recites “preferably a methyl or a benzyl group” which is the narrower statement of the range/limitation.
claim 3 recites the broad recitation “wherein n=0 or 1 or 2”, and the claim also recites “preferably 2” which is the narrower statement of the range/limitation.
claim 5 recites the broad recitation “the molar ratio is in the range of between 3 and 1”, and the claim also recites “preferably between 2.5 and 1.1” and “more preferably between 2.0 and 1.2” which are the narrower statements of the range/limitation.
claim 7 recites the broad recitation “a solvent which is a hydrocarbon”, and the claim also recites “preferably toluene, or a C5-10 alkane”, “most preferred hexane or heptane” which are the narrower statements of the range/limitation.
claim 8 recites the broad recitation “a solvent which is an organic carbonate”, and the claim also recites “preferably a carbonate of the the formula (X)” which is the narrower statement of the range/limitation.
claim 12 recites the broad recitation “an molar ratio of between 1:1'000 to 1:5”, and the claim also recites “particularly 1:100 to 1:10” which is the narrower statement of the range/limitation.
The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
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.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Kobayashi et al. (JP 53-149979 A) in view of Schudel et al. (“On the Chemistry of Vitamin E, part 5”) and Hoffmann La Roche (GB-1,323,852-A).
Regarding claim 15, the claimed invention is drawn to the compound of formula (I-A):
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586
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wherein R’ represents a phenol protecting group and the wavy line represents a carbon-carbon bond linked to the carbon-carbon double bond which is either in the Z or in the E-configuration. Kobayashi et al. (with reference to Schudel et al.) disclose a previously known intermediate compound of the following formula:
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184
544
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(see section 4).
This then undergoes further reaction to form a final polycyclic compound of the following formulas:
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186
534
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and
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526
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(see section 5).
The intermediate compound of Kobayashi et al. (and Schudel et al.) is formed by the following reaction:
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178
550
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(see section 4).
This intermediate compound of Kobayashi et al. (and Schudel et al.) differs from the claimed compound in that it has an unprotected OH group instead of the OR’ on the phenolic/aromatic ring.
Hoffmann La Roche discloses a similar final compound of the following formula:
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334
1044
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,
in which Y represents one of the groups
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118
446
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n stands for zero, 1, 2 or 3, X represents a hydrogen atom or an alkanoyl or aroyl group R1, R2 and R3 each represent a hydrogen atom or a methyl group (see claim 1). This is derived from an intermediate, which is formed by reacting:
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370
716
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with
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924
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,
where Z represents a halogen atom or a hydroxyl group which may be etherified by an alcohol or esterified with an acid (see claim 1). This reaction obviously embraces the reaction disclosed by Kobayashi et al. (and Schudel et al.). In addition, the teachings of Hoffmann La Roche demonstrate that an unprotected OH group and the instantly claimed protected group, OR’, on the phenolic/aromatic reactant are equally suitable for this type of reaction. In light of this, it has been found that combining or substituting equivalents known for the same purposed is prima facie obvious – see MPEP 2144.06. Furthermore, the obvious substitution of the unprotected phenolic/aromatic reactant with a protected phenolic/aromatic reactant in the reaction of Kobayashi et al. (and Schudel et al.) would have obviously arrived at the instantly claimed compound.
Therefore, the instantly claimed compound would have been obviously envisaged by the skilled artisan (before the effective filing date of the claimed invention) in view of the teachings of Kobayashi et al., Schudel et al. and Hoffmann La Roche because: (a) Kobayashi et al. (and Schudel et al.) disclose a similar compound (and reaction for making) having an unprotected OH group instead of the OR’ on the phenolic/aromatic ring; (b) Hoffmann La Roche disclose a reaction that obviously embraces the reaction disclosed by Kobayashi et al. (and Schudel et al.); (c) the teachings of Hoffmann La Roche demonstrate that an unprotected OH group and the instantly claimed protected group, OR’, on the phenolic/aromatic reactant are equally suitable for this type of reaction; (d) it has been found that combining or substituting equivalents known for the same purposed is prima facie obvious; and (e) the obvious substitution of the unprotected phenolic/aromatic reactant with a protected phenolic/aromatic reactant in the reaction of Kobayashi et al. (and Schudel et al.) would have obviously arrived at the instantly claimed compound.
Claims 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Kobayashi et al. (JP 53-149979 A) in view of Schudel et al. (“On the Chemistry of Vitamin E, part 5”), Hoffmann La Roche (GB-1,323,852-A) and Bonrath et al. (US 2006/0052618 A1).
Regarding claims 1-4, the combined teachings of {Kobayashi et al., Schudel et al. & Hoffmann La Roche} are as set forth above and incorporated herein to obviously satisfy the limitations of dependent claims (2-4). Kobayashi et al., Schudel et al. and Hoffmann La Roche disclose the use of an iron-based catalyst. Accordingly, they fail to disclose (1-4) the use of an acidic catalyst being: either Gd(OTf)3 or Tm(OTf)3 or Al(OTf)3 or Y(OTf)3 or Fe(OTf)2 or camphorsulfonic acid or BiCl3, wherein OTf represents trifluoromethanesulfonate.
Bonrath et al. et al. disclose a reaction similar to those described in Kobayashi et al., Schudel et al. and Hoffmann La Roche (see paragraphs 0006-0014; see also paragraphs 0038-0039). They present triflate catalysts, including Gd(OTf)3, Tm(OTf)3 and Y(OTf)3, as alternative catalysts for this type of reaction (see paragraphs 0011-0014; see also paragraph 0005).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use the instantly claimed acid catalyst in the process resulting from the combined teachings of {Kobayashi et al., Schudel et al. & Hoffmann La Roche} because: (a) Kobayashi et al., Schudel et al. and Hoffmann La Roche disclose the use of an iron-based catalyst; (b) Bonrath et al. et al. disclose a reaction similar to those described in Kobayashi et al., Schudel et al. and Hoffmann La Roche, and (c) Bonrath et al. present triflate catalysts, including Gd(OTf)3, Tm(OTf)3 and Y(OTf)3, as alternative catalysts for this type of reaction.
Regarding claims 5-10, the combined teachings of {Kobayashi et al., Schudel et al., Hoffmann La Roche & Bonrath et al.} are as set forth above and incorporated herein. The supporting teachings of Bonrath et al. further demonstrate that:
the molar ratio of claim (5) is recognized in the art as a suitable reactant ratio for this type of reaction (see paragraph 0026);
the molar ratio of claim (6) is recognized in the art as a suitable reactant/catalyst ratio for this type of reaction (see paragraph 0027);
the solvent(s) of claims (7-9) is/are recognized in the art as a suitable reaction medium for this type of reaction (see paragraphs 0019-0025); and
the temperature range of claim (10) is recognized in the art as a suitable reaction temperature for this type of reaction (see paragraph 0031).
Regarding claim 11, the combined teachings of {Kobayashi et al., Schudel et al., Hoffmann La Roche & Bonrath et al.} are as set forth above and incorporated herein. The primary teachings of Kobayashi et al. (see sections 4-5) and Schudel et al. (see page 2518) further demonstrate that instantly claimed steps c) and d) (step b) being optional) are recognized in the art as suitable steps for achieving their final polycyclic compounds.
Regarding claim 12, the combined teachings of {Kobayashi et al., Schudel et al., Hoffmann La Roche & Bonrath et al.} are as set forth above and incorporated herein. The primary teachings of Kobayashi et al. and Schudel et al. fail to explicitly disclose: (12) wherein the basic catalyst in step d) is present in a molar ratio to the compound of the formula (V) of between 1:1,000 to 1:5. However, the skilled artisan would have recognized catalyst content as a result effective variable because catalysts are typically provided in amounts to initiate reactions, as well as regulate reaction rate. In light of this, it has been found that, “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation,” – In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955); and “A particular parameter must first be recognized as a result-effective variable, i.e., a variable which achieves a recognized result, before the determination of the optimum or workable ranges of said variable might be characterized as routine experimentation,” –In re Boesch, 617 F.2d 272, 205 USPQ 215 (CCPA 1980).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to provide the instantly claimed amount of basic catalyst in the method resulting from the combined teachings of {Kobayashi et al., Schudel et al., Hoffmann La Roche & Bonrath et al.} because: (a) the skilled artisan would have recognized catalyst content as a result effective variable because catalysts are typically provided in amounts to initiate reactions, as well as regulate reaction rate; (b) it has been found that, “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation;” and (c) it has been found that “A particular parameter must first be recognized as a result-effective variable, i.e., a variable which achieves a recognized result, before the determination of the optimum or workable ranges of said variable might be characterized as routine experimentation.”
Allowable Subject Matter
Claims 13 and 14 would be allowable if rewritten to overcome the objection set forth in this Office action and to include 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: the combined teachings of {Kobayashi et al., Schudel et al., Hoffmann La Roche & Bonrath et al.} fair to reasonably teach or suggest the instantly claimed process involving (13) partial hydrogenation of the compound of formula (VI) and (14) full hydrogenation of the compound of formula (VI).
International Search Report
The international search report cited three X-references. All three references have been considered, and the US-equivalent of one has been applied as prior art.
Communication
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MICHAEL J FEELY whose telephone number is (571)272-1086. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MICHAEL J FEELY/Primary Examiner, Art Unit 1766
June 10, 2026
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