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 .
This is a Final Office Action.
Election/Restrictions
Applicant's election without traverse of Group (II) in the reply filed on December 10, 2025 is acknowledged. Group (II), drawn to a process of making compounds of formula IA’, embraced by claims 48, 49, 54, 55, 59, 65, 66, 69, 71-73, 75, 77, 79, 81-83, 85, 86 and 96 was elected by Applicant.
Applicant elected the following species:
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and claims 48, 49, 54, 55, 59, 65, 66, 69, 71-73, 75, 77, 79, 81-83, 85, 86 and 96 read on said species. However, claim 96 is an additional step further into the synthesis and is withdrawn based on the species election but will be rejoined upon allowable subject matter found in claim 48.
Claims 48, 49, 54, 55, 59, 65, 66, 69, 71-73, 75, 77, 79, 81-83, 85, 86 and 96 are pending and claims 48, 49, 54, 55, 59, 65, 66, 69, 71-73, 75, 77, 79, 81-83, 85 and 86 are under consideration. Claim 96 is withdrawn based on the species election.
Claim Objections
The objection to claim 72 because of the term “tetrafluoroforate” is withdrawn based on the amendments.
The objection to claims 77 and 86 because of the “K3PO4” and “HSiCL2” is withdrawn based on the amendments.
The objection to claim 86 because of the phrase “selected from” is withdrawn based on the amendments.
Claims 55 and 59 are objected to because of the following informalities: the term “Formula” should be added prior to the terms ID and ID’ in said claims. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The rejection of claim 48 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for the phrase, “the sp2 hybridized carbon atom” is withdrawn based on the amendments.
The rejection of claim 72 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for the copper (I) is withdrawn based on the amendments.
The rejection of claim 79 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for Formula BII is withdrawn based on the amendments.
The rejection of claims 48, 49, 54, 55, 59, 65, 66, 75, 77, 79, 81-83, 85 and 86 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement, is withdrawn based on the amendments.
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 48, 66 and 69 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 pre-AIA the applicant regards as the invention.
Regarding claim 48, the Formula IA’ is vague. On page 2, the variables R2a are not defined. Moreover, the Formula IA’ on page 3 is different than the one on page 2.
The following is a quotation of the fourth paragraph of 35 U.S.C. 112:
Subject to the [fifth paragraph of 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 66 is rejected under 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 66 no longer limits claim 48 based on the amendments. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim 69 is rejected under 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 69 does not further limit claim 48 based on the amendments. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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 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.
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.
This application currently names joint inventors. In considering patentability of the claims under 35 U.S.C. 103(a), the examiner presumes that the subject matter of the various claims was commonly owned at the time any inventions covered therein were made absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and invention dates of each claim that was not commonly owned at the time a later invention was made in order for the examiner to consider the applicability of 35 U.S.C. 103(c) and potential 35 U.S.C. 102(e), (f) or (g) prior art under 35 U.S.C. 103(a).
Claims 48, 49, 54, 55, 59, 65, 66, 69, 71-73, 75, 77, 79, 81-83, 85 and 86 are rejected under AIA 35 U.S.C. 103(a) as being unpatentable over Tomita et al. (Chem. Asian. J., 2006, 1-2, 161-166, cited on the IDS) in view of Javdani et al. (US 4482751, cited on the IDS), van Kalkeren et al. (Chem. Eur. J. 2011, 17, 11290–11295).
The present application claims a method of making compound (IA’) by reacting an aldehyde compound of formula ((IIA) with an alkenyl boron compound, e.g., (4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane) and a catalyst in presence of a base and an optional solvent, wherein the catalyst is prepared from a copper (I) or (II) salt (CuF2) and a phosphine compound, e.g., ((R)-DTBM-SEGPHOS), wherein the phosphine is at least two equivalents of a monophosphine or at least one equivalent of a diphosphine with respect to the copper I salt or is at least four equivalents of a monophosphine or at least two equivalents of a disphosphine with respect to the copper II salt.
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Tomita et al. teach a method of making various compounds similar to compound (IA’) by reacting various aldehyde compounds (not of formula (IIA)) with an alkenyl boron compound (4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane) and a catalyst in presence of a base (TBAT) and an optional solvent (DMF or toluene), wherein the catalyst is prepared from a copper (I) or (II) salt (10 mol % CuF2) and a phosphine (20 mol % (R)-DTBM-SEGPHOS), see below and page 163.
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The difference between the claimed process and the Tomita is the starting aldehyde compound IIA: 1) a cyclohexyl or cyclopropyl ring (see compounds 10 and 12 in Table 1 above) versus Applicant’s cyclobutyl ring; and 2) an unsubstituted cyclohexyl or cyclopropyl ring versus Applicant’s C(O)alkyl substituent.
1) The MPEP 2144.09 states “Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
2) The use of analogous reactants in a known process is prima facie obvious. In re Durden, 226 USPQ 359 (1985). Once the general reaction has been shown to be old, the burden is on Applicants to present reasons or authority for believing that a group on the starting material would take part in or affect the basic reaction and thus alter the nature of the product or the operability of the process. In looking at the instant claimed process as a whole, as stated in In re Ochiai, 37 USPQ 2d 1127 (1995), the claimed process would have been suggested to one skilled in the art.
Tomita does not teach 1) the specific bases found in claim 77; nor 2) the recovery of the phoshine compound.
Substituting one base for another and one solvent for another is routine and conventional in an organic chemistry lab. Therefore, the replacement would be obvious since the bases and solvents are alternatively useable, unless there is evidence to the contrary. However, the specification does not indicate such evidence.
Javdani et al. teaches the recovery of a phosphine compound with an oxidizing agent, hydrogen peroxide, see column 3, lines 5-12. The van Kalkeren reference teaches the in situ phosphine oxide reduction, see the title, see also Table 2 on page 11294. Therefore, the recovery of the phosphine compound is obvious, unless there is evidence to the contrary, although there is nothing in the specification that indicates so.
Thus, the claimed process is rendered obvious as outlined in the rejection by Tomita et al. in view of Javdani et al. and van Kalkeren et al.
Applicant traverses by stating, “A cyclobutyl ring is not a homolog nor a positional isomer of a cyclohexyl ring-they differ by two carbon atoms in ring size and cyclobutane has a ring strain that cyclohexane does not. Furthermore, the acyloxymethyl substituent on the cyclobutyl ring adds structural and electronic complexity not present in any of Tomita's substrates. None of the chemical compounds disclosed in Tomita have a chemical group which could be interpreted as a "homolog" of the currently claimed acyloxymethyl substituent.”
This is not persuasive. A cyclopropyl, cyclobutyl and cyclohexyl are homologous ring systems, that differ in the number of CH2 groups in the ring.
Applicant further states, “Further, Tomita's own data demonstrates significant substrate-dependent limitations. For example, the cyclohexanecarboxaldehyde (entry 10) vinylation product was obtained in only 42% yield with significant homo-aldol byproduct formation (35%). See Tomita at 164. Tomita explicitly acknowledges that "reactions of linear aliphatic aldehydes are still difficult" (entry 13) and that "[t]he remaining limitations of this reaction are its inapplicability to linear aliphatic aldehydes." Id. at 164, 165. This substrate sensitivity undermines the assertion that substituting one aldehyde for another would be possible with a reasonable expectation of success.”
This is also not persuasive. There is no such limitation based on yield or byproduct formation in claim 48. Moreover, there is more than one entry for the cyclohexyl ring, see entry 11, which has a 94% yield and 98% ee. Furthermore, the cyclopropyl entry has an 87% yield and 92% ee.
Although the reference may recognize the reactions of linear aliphatic aldehydes as difficult, the reference provides the guidance necessary to achieve high yielding and ee as noted.
Thus, the rejection is maintained.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SUSANNA MOORE whose telephone number is (571)272-9046. The examiner can normally be reached Monday - Friday, 10:00 am to 7:00 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey Murray, can be reached on 571-272-9023. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SUSANNA MOORE/Primary Examiner, Art Unit 1624
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