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 44-48 of A. Doppiu et al., US 18/268,996 (Feb. 15, 2022) are pending and under examination. Claims 45-47 are rejected. Claims 44 and 48 are in condition for allowance.
Withdrawal Claim Rejections 35 U.S.C. 112(a) – Written Description
Rejection of claim 44 under 35 U.S.C. 112(a) as failing to comply with the written description requirement is withdrawn in view of Applicant’s amendments.
Withdrawal Claim Rejections - 35 USC § 102 (AIA )
Rejection of claim 46 under 35 U.S.C. 102(a)(1) as being anticipated by P. Elmes et al., 333 Annals of the New York Academy of Sciences, 225-228 (1980) (“Elmes”) is withdrawn in view of Applicant’s amendments.
Rejection of claim 46 under 35 U.S.C. 102(a)(1) as being anticipated by C. Lindsay et al., 19 Inorganic Chemistry, 3503-3508 (1980) (“Lindsay”) is withdrawn in view of Applicant’s amendments.
Maintained Claim Rejections - 35 USC § 102 (AIA )
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.
§ 102(a)(1)/(2) Rejection over T. Colacot et al., US 8,772,520 (2014) (“Colacot”)
Rejection of claim 45 under 35 U.S.C. 102(a)(1)/(2) as being anticipated by T. Colacot et al., US 8,772,520 (2014) (“Colacot”) is maintained.
Claim 45 is claimed entirely using product by process language. Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. MPEP § 2113(I). The patentability of a product does not depend on its method of production. MPEP § 2113(I). If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process. MPEP § 2113(I) (citing In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985)).
In Example 4, Colacot teaches reaction of Pd(COD)Br2 with PtBu3 in methanol to give the claimed compound Pd(PtBu3)2 in 95% yield. Colacot at col. 16, lines 15-34 (Example 4). Colacot’s Pd(PtBu3)2 meets the claim 45 product limitations of [PdZAZB] (I), where “a phosphine ligand is PtBu3 . . . ”.
Claim 45 is anticipated because the claim 45 product-by-process limitations cannot distinguish under 35 U.S.C. 102(a)(1)/(2).
Applicant’s Argument
Applicant argues that claim 45 has been amended as follows:
Claim 45 . . . is prepared from Pd-VS and a phosphine ligand selected from an of PtBu3 . . .”
This argument is not persuasive because as noted above claim 45 is anticipated because the claim 45 product-by-process limitations cannot distinguish under 35 U.S.C. 102(a)(1)/(2).
Applicant further argues that the claims are amended by removing 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-bis(diphenylphosphino)propane (dppp), and [Pd(PtBu3)2] as choices from the compound and ligand lists in the various claims.
This argument is not persuasive because, in fact, tri-tertbutylphosphine (PtBu3) has not been removed from claim 45 by amendment.
§ 102(a)(1) Rejection over J. Krause et al., 121 Journal of the American Chemical Society, 9807-9823 (1999) (“Krause”)
Claims 45 and 47 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by J. Krause et al., 121 Journal of the American Chemical Society, 9807-9823 (1999) (“Krause”).
As noted above, claim 45 is claimed using product by process language (i.e., “obtained by the method according to claim 44”).
In a first step, Krause teaches the synthesis of complex 36 as follows:
PNG
media_image1.png
200
400
media_image1.png
Greyscale
Krause at page 9822, col. 2. Krause discloses the following details regarding the transformation of complex 36 into claimed compound Pd(PtBu3)2 [PdZAZB] (I).
The synthesis of the tBu3P complexes 16, 27, and 36 is furthermore complicated by thermal instability and, hence, needs to be carried out at low temperatures (<-30 °C) as described in the Experimental Section.
At 20 °C solid 16 decomposes very quickly and 27 in the course of a day, whereas 36 (>100 °C dec) is stable for a long time. In solution, these complexes undergo ligand redistribution reactions to afford the very stable Pd(PtBu3)2 together with (decomposing) 5 or 6 or (stable) 7 (eq 3). For 16 this ligand redistribution starts already at -30
PNG
media_image2.png
200
400
media_image2.png
Greyscale
°C (and is fast at 20 °C), and for 27 and 36 it starts slowly at about 0 °C. This reaction cannot be completely suppressed in the synthesis of highly soluble 16 and 27, which therefore contain about 10% of Pd(PtBu3)2 as a byproduct.
Krause at page 9812, col. 2 to 9813, col. 1 (emphasis added).
In eq. 3, Krause’s Pd(PtBu3)2 meets the claim 45 product limitations of [PdZAZB] (I), where “a phosphine ligand is PtBu3 . . . ”.
The above Krause process meets the process limitations of base claim 44 where Krause compound 36 is, per claim 44:
Claim 44 . . . 1,2-divinyl-1,1,3,3-tetramethyldisiloxanepalladium (Pd-VS) . . .
See Specification at page 159, line 25. And Krause’s PtBu3 also meets base claim 44’s limitation of phosphine ligands ZA and ZB. Accordingly, each and every limitation of claim 45 is met by Krause and is therefore anticipated.
Respecting claim 47, as discussed above, Krause teaches the following formation of Pd(PtBu3)2 as a side reaction from decomposition of silicon compound 36.
PNG
media_image2.png
200
400
media_image2.png
Greyscale
Krause at page 9812, col. 2 to 9813, col. 1. With respect to compound 36, Krause’s above eq. 3 is drawn by the Examiner as follows:
PNG
media_image3.png
200
400
media_image3.png
Greyscale
Krause’s so formed preparation comprises Pd(PtBu3)2, which meets the limitations of claim 47 [PdZAZB] (I), where “ZA and ZB are independently selected from . . tri-tertbutylphosphine (PtBu3) . . . ” and Krause’s compound 7 meets the claim 47 limitation of “an organosilicon compound”.
Accordingly, Krause eq 3 teaches each and every limitation of claim 47:
Claim 47 A preparation containing
i. a compound according to general formula [PdZAZB] (I), wherein and ZA and ZB are independently selected from the group consisting of tri-tertbutylphosphine (PtBu3) . . . [i.e., Pd(PtBu3)2] and
ii. an organosilicon compound [i.e., compound 7] 1.
Applicant’s Argument
Applicant argues that the claims are amended by removing 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-bis(diphenylphosphino)propane (dppp), and [Pd(PtBu3)2] as choices from the compound and ligand lists in the various claims.
This argument is not persuasive because, in fact, tri-tertbutylphosphine (PtBu3) has not been removed from claims 45 or 47 by amendment.
New 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.
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 AIA 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.
Claim 46 is rejected under AIA 35 U.S.C. 103 as being unpatentable over P. Mampuys et al., 7 ACS Catalysis, 5549-5556 (2017) (“Mampuys”) alone or Mampuys in further view of J. Pan et al., CN 101693725 A (2010) (“Pan”).
P. Mampuys et al., 7 ACS Catalysis, 5549-5556 (2017) (“Mampuys”)
Mampuys discloses that Pd(OAc)2/BuP(Ad)2 is useful as a catalyst to obtain heterocycles 3, which are key intermediates for the synthesis of biologically active N3-substituted quinazolin-4(3H)-ones and N1,N3-disubstituted quinazoline-2,4(1H,3H)-diones (Scheme 2). Mampuys at Abstract; Id. at page 5550, cols. 1-2 (citing Scheme 2); Id. at page 552 (Scheme 6).
Mampuys teaches the following synthesis of intermediate 3g using BuP(Ad)2 as a catalyst.
PNG
media_image4.png
200
400
media_image4.png
Greyscale
Mampuys at page 5552 (Scheme 6).
Mampuys teaches that compound 3g is a useful intermediate to obtain APIs Alfuzosin, Doxazosin, and Proazosin. Mampuys at page 5552 (Scheme 6).
Mampuys teaches that the active catalyst, formed from Pd(OAc)2/BuP(Ad)2 in situ, is Pd0-L, which would have the following structure.
Structure of Mampuys Pd0-L or Pd(BuP(Ad)2)2 (RN 1006871-91-5)
PNG
media_image5.png
200
400
media_image5.png
Greyscale
Mampuys at page 5553 (Scheme 7); see also, CAS Abstract and Indexing of from P. Mampuys et al., 7 ACS Catalysis, 5549-5556 (2017).
Differences between Mampuys and Claim 46
Mampuys compound Pd(BuP(Ad)2)2 (RN 1006871-91-5) differs from claim 46 compounds [Pd(P(1-Ad)2tBu)2], [Pd(P(1-Ad)2iPr)2], and [Pd(P(1-Ad)tBu2)(P(1-Ad)iPr2)] in n-butyl (Mampuys) versus t-butyl or isopropyl (claim 46). For example, claim 46 compound [Pd(P(1-Ad)2tBu)2] has the following structure
PNG
media_image6.png
200
400
media_image6.png
Greyscale
J. Pan et al., CN 101693725 A (2010) (“Pan”)
J. Pan et al., CN 101693725 A (2010) (“Pan”) teaches that Pd(PtBu3)2, is an emerging third-generation palladium organocatalyst, that exhibits excellent performance in various coupling reactions and is therefore, this catalyst plays an extremely important role in basic chemical industry and pharmaceutical chemical industry. Pan at page 6 of 8, last paragraph.
Obviousness Rationale
Obviousness of a claimed compound can be shown where there is initial motivation to select a prior art compound and thereafter still further motivation to make the specific structural modifications thereto so as to arrive at a claimed compound. See MPEP § 2143(B) (discussing “lead compound cases” in Examples 9-11 with respect to pharmaceutical applications).2 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. MPEP § 2144.09(II).
Claim 46 is obvious because one of ordinary skill apprised by Mampuys that Pd(BuP(Ad)2)2 (RN 1006871-91-5) is a useful Pd-coupling catalyst is motivated to prepare isomers and next-adjacent homologs with respect to the two n-butyl groups thereby arriving at each and every limitation of claim 46, with a reasonable expectation that such compounds would be useful Pd-coupling catalysts. MPEP § 2144.09(II). For example, one of ordinary skill is motivated to prepare any of the claim 46 compounds [Pd(P(1-Ad)2tBu)2], [Pd(P(1-Ad)2iPr)2], and [Pd(P(1-Ad)tBu2)(P(1-Ad)iPr2)]) by simple substitution of Mampuys’s n-butyl group with either of t-butyl or isopropyl so as to arrive at the instantly claimed Pd compounds. One of ordinary skill is particularly motivated by Pan, which teaches that Pd(PtBu3)2, (having a t-butyl groups) is an emerging third-generation palladium organocatalyst, that exhibits excellent performance in various coupling reactions and therefore this catalyst plays an extremely important role in basic chemical industry and pharmaceutical chemical industry. Pan at page 6 of 8, last paragraph.
Subject Matter Free of the Art of Record
Claims 44 and 48 are free of the art of record. Independent claim 44 requires the preparation of a compound of general formula [PdZAZB] (I) as a limitation because its synthesis is the thrust of the specification. Specification at page 9, [0024]. In general, a preamble limits the invention if it recites essential structure or steps, or if it is necessary to give life, meaning, and vitality to the claim. MPEP § 2111.02 (citing Catalina Mktg. Int’l, Inc. v. Coolsavings.com, Inc., 289 F.3d 801, 808 (Fed. Cir. 2002)).
The closest art of record to claim 44 is J. Krause et al., 121 Journal of the American Chemical Society, 9807-9823 (1999) (“Krause”). Krause teaches the synthesis of claimed compound Pd(PtBu3)2 from compound 36 as follows. In a first step, Krause teaches the synthesis of complex 36 as follows:
PNG
media_image1.png
200
400
media_image1.png
Greyscale
Krause at page 9822, col. 2. Krause teaches that above reaction was performed in ether as the solvent. Id. Krause further teaches that in solution, complex 36 undergoes a ligand redistribution reaction (per eq 3) to afford the very stable Pd(PtBu3)2.
Krause discloses the following details regarding the transformation of complex 36 into claimed compound Pd(PtBu3)2:
The synthesis of the tBu3P complexes 16, 27, and 36 is furthermore complicated by thermal instability and, hence, needs to be carried out at low temperatures (<-30 °C) as described in the Experimental Section.
At 20 °C solid 16 decomposes very quickly and 27 in the course of a day, whereas 36 (>100 °C dec) is stable for a long time. In solution, these complexes undergo ligand redistribution reactions to afford the very stable Pd(PtBu3)2 together with (decomposing) 5 or 6 or (stable) 7 (eq 3). For 16 this ligand redistribution starts already at -30
PNG
media_image2.png
200
400
media_image2.png
Greyscale
°C (and is fast at 20 °C), and for 27 and 36 it starts slowly at about 0 °C. This reaction cannot be completely suppressed in the synthesis of highly soluble 16 and 27, which therefore contain about 10% of Pd(PtBu3)2 as a byproduct.
Krause at page 9812, col. 2 to 9813, col. 1 (emphasis added). The above Krause process meets the limitations of claim 44 where Krause compound 3 is, per claim 44:
Claim 44 . . . 1,2-divinyl-1,1,3,3-tetramethyldisiloxanepalladium (Pd-VS) . . .
See Specification at page 159, line 25. And Krause’s PtBu3 meets the claim 44 limitation of phosphine ligands ZA and ZB.
However, Krause differs from claim 44 in that Krause does teach step B:
Claim 44 . . . B. reacting the palladium compound and the monophosphine ligand and/or the bisphosphine ligand from step A in a non-ethereal solvent Sc . . .
because Krause performs the reaction in ether.
Claim 44 is not obvious over Krause because one of ordinary skill is not motivated to replace Krause’s ether solvent with (per claim 44) a non-ether solvent for the following reasons. Frist, one of ordinary skill is not motivated to initially and specifically select compound 36 (for example, from among Krause compounds 16, 27, and 36) for further development and second to optimize its conversion to Pd(PtBu3)2, for example, by solvent optimization and temperature. MPEP § 2144.05(II). One of ordinary skill is not so motivated because Krause does not provide any details of the redistribution reaction of compound 36 to form Pd(PtBu3)2 (for example yields and temperature); rather Krause notes its presence as a side product and that it decomposes slowly at -30 °C to Pd(PtBu3)2.
It is noted here that the Written Opinion of the International Searching Authority, PCT/EP2021/085873 (Aug. 1, 2022), cites J. Pan et al., CN 101693725 A (2010) (Ref D1, “Pan”) and T. Colacot et al., US 8,772,520 (2014) (Ref D2, “Colacot”).
J. Pan et al., CN 101693725 A (2010) (“Pan”) teaches that Pd(PtBu3)2, is an emerging third-generation palladium organocatalyst, that exhibits excellent performance in various coupling reactions and is therefore, this catalyst plays an extremely important role in basic chemical industry and pharmaceutical chemical industry. Pan at page 6 of 8, last paragraph. In Example 1, Pan teaches synthesis of Pd(PtBu3)2 in 70% yield by reacting tris(dibenzylideneacetone) dipalladium (0) (abbreviated Pd2(DBA3) chloroform adduct, with PtBu3 in anhydrous N,N-dimethylformamide. Pan at page 6 of 8 (Example 1).
Where Pd2(DBA3) has the following structure:
PNG
media_image7.png
200
400
media_image7.png
Greyscale
(CAS RN 51364-51-3).
Pan differs from claim 44 in that it does not teach the reactant:
Claim 44 . . . 1,2-divinyl-1,1,3,3-tetramethyldisiloxanepalladium (Pd-VS) . . .
Claim 44 is not obvious over Pan because the art of record does not motivate one of ordinary skill to employ the claim 44 “1,2-divinyl-1,1,3,3-tetramethyldisiloxanepalladium (Pd-VS)” as a reagent on Pan’s Example 1.
In Example 4, T. Colacot et al., US 8,772,520 (2014) (“Colacot”) teaches reaction of Pd(COD)Br2 with PtBu3 in methanol to give Pd(PtBu3)2 in 95% yield. Colacot at col. 16, lines 15-34 (Example 4). Colacot differs from claim 44 in the same way as Pan (above). Claim 44 is not obvious over Colacot because the art of record does not motivate one of ordinary skill to employ the claim 44 silicon-containing “1,2-divinyl-1,1,3,3-tetramethyldisiloxanepalladium (Pd-VS)” as a reagent on Colacot’s Example 4.
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 ALEXANDER R PAGANO whose telephone number is (571)270-3764. The examiner can normally be reached 8:00 AM through 5:00 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, Scarlett Goon can be reached at 571-270-5241. 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.
ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 See specification definition of “organosilicon compound”. Specification at page 10 line 27 – page 11, line 5, [0025].
2 The MPEP warns against applying the lead compound analysis rigidly in view of the flexible approach stated in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) see also, MPEP § 2143(B), Example 11 (citing Altana Pharma AG v. Teva Pharm. USA, Inc., 566 F.3d 999, 91 USPQ2d 1018 (Fed. Cir. 2009) a ‘restrictive view of the lead compound test would present a rigid test similar to the teaching-suggestion-motivation test that the Supreme Court explicitly rejected in KSR’).
Prosecution Insights