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 the first action on the merits.
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 has not pointed to any errors in the Examiner’s analysis of the classification of the different inventions. The requirement is still deemed proper and is therefore made FINAL.
Applicant elected the following species:
PNG
media_image1.png
190
466
media_image1.png
Greyscale
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 However, claim 96 is an additional step further into the synthesis and is withdrawn based on the species election but will be rejoined upon allowable subject matter found in claim 48.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 1-3, 5, 6, 8, 10, 11, 15, 16, 20, 21, 25, 31, 32, 35, 37-39, 41, 44, 46, 48, 49, 54, 55, 59, 65, 66, 69, 71-73, 75, 77, 79, 81-83, 85-89, 93 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 Claim 96 is withdrawn based on the species election and claims 1-3, 5, 6, 8, 10, 11, 15, 16, 20, 21, 25, 31, 32, 35, 37-39, 41, 44, 46, 88, 89 and 93 are withdrawn from consideration as drawn to nonelected subject matter.
Claim Objections
Claim 72 is objected to because of the following informalities: the term “tetrafluoroforate” is misspelled and should be replaced with “tetrafluoroborate” in said claim. Appropriate correction is required.
Claims 77 and 86 are objected to because of the following informalities: the “K3PO4” and “HSiCL2” listed separately as a second option (ii) is redundant. The claim states, “selected from” with an “or” between the last two groups. Appropriate correction is required.
Claim 86 is objected to because of the following informalities: the phrase “selected from” is repeated in the claim. Appropriate correction is required.
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.
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, 72 and 79 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.
In claim 48, the phrase, “the sp2 hybridized carbon atom” is vague, see page 10 line 1. Said phrase lacks antecedent basis. To overcome the rejection, the term “the” may be replaced with “an” in said phrase.
Regarding claim 72, the copper (I) is vague since the valency is not complete. Should these salts be copper (II)?
With regards to claim 79, the compound of Formula BII is vague. Formula BII is not found in the examined claims. To overcome the rejection, the “BII” should be replaced with “IIA” in said claim.
The following is a quotation of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), first paragraph:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same and shall set forth the best mode contemplated by the inventor of carrying out his invention.
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. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for pre-AIA the inventor(s), at the time the application was filed, had possession of the claimed invention.
This is a written description rejection.
The analysis for adequate written description considers the following:
(a) Actual reduction to practice;
(b) Disclosure of drawings or structural chemical formulas;
(c) Sufficient relevant identifying characteristics, such as (i) complete/partial structure, (ii) physical and/or chemical properties, and (iii) functional characteristics when coupled with known or disclosed correlation with structure; and
(d) Representative number of samples.
A lack of adequate written description issue arises if the knowledge and level of skill in the art would not permit one skilled in the art to immediately envisage the product claimed from the disclosed process. See, e.g., Fujikawa v. Wattanasin, 93 F.3d 1559, 1571,39 USPQ2d 1895, 1905 (Fed. Cir. 1996) (a "laundry list" disclosure of every possible moiety does not constitute a written description of every species in a genus because it would not "reasonably lead" those skilled in the art to any particular species); In re Ruschig, 379 F.2d 990, 995, 154 USPQ 118, 123 (CCPA 1967).
An applicant may also show that an invention is complete by disclosure of sufficiently detailed, relevant identifying characteristics which provide evidence that applicant was in possession of the claimed invention, i.e., complete or partial structure, other physical and/or chemical properties, functional characteristics when coupled with a known or disclosed correlation between function and structure, or some combination of such characteristics.
In particular, the specification as original filed fails to provide sufficient written description for the terms “an alkenyl boron compound,” “copper I salt or a copper II salt” and a “phosphine” on the basis that the application has not demonstrated possession of the scope of said terms. The mere fact that Applicant may have discovered an enantioselective alkenylation of aldehydes with specific alkenyl boron compounds, copper I salts or copper II salts and a phosphine compound, is not sufficient to claim the entire genus.
The written description requirement for a claimed genus may be satisfied through sufficient description of a representative number of species by actual reduction to practice, reduction to drawings, or by disclosure of relevant, identifying characteristics, i.e., structure or other physical and/or chemical properties, by functional characteristics coupled with a known or disclosed correlation between function and structure, or by a combination of such identifying characteristics, sufficient to show the applicant was in possession of the claimed genus. See Eli Lilly, 119 F.3d at 1568, 43 USPQ2d at 1406.
A "representative number of species" means that the species which are adequately described are representative of the entire genus. Thus, when there is substantial variation within the genus, one must describe a sufficient variety of species to reflect the variation within the genus. The disclosure of only one species encompassed within a genus adequately describes a claim directed to that genus only if the disclosure "indicates that the patentee has invented species sufficient to constitute the gen[us]."
Thus, said claims are rejected under 35 USC 112(a) (Written Description).
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 (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 ((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.
PNG
media_image2.png
159
341
media_image2.png
Greyscale
PNG
media_image3.png
142
248
media_image3.png
Greyscale
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.
PNG
media_image4.png
166
771
media_image4.png
Greyscale
PNG
media_image5.png
748
768
media_image5.png
Greyscale
The difference between the claimed process and the Tomita is the starting aldehyde compound IIA: 1) a cyclohexyl ring (see compound 10 in Table 1 above) versus Applicant’s cyclobutyl ring; and 2) an unsubstituted cyclohexyl ring versus Applicant’s methylalkoxy 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.
Conclusion
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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
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.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/SUSANNA MOORE/Primary Examiner, Art Unit 1624