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 .
Request for Continued Examination (RCE)
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 1/27/26 has been entered.
Priority
This application is a 371 of PCT/US21/29526 04/28/2021
PCT/US21/29526 has PRO 63/020,888 05/06/2020.
Claim Status
Claims 1-21, 23-30, 32, 34, 36-74 are pending.
Claim rejections not reiterated are withdwrawn.
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 for establishing a background for determining obviousness under 35 U.S.C. 103 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.
Claims 1-8, 13, 18-21, 23-30, 32, 34, 36-62, 65, 72-74 are rejected under 35 U.S.C. 103 as being unpatentable over Brown et al. (US20160068545) in view of Brubaker et al. (Org. Lett. 2007, 9, 18, 3523–3525), Harrington et al. (US20180289720, publ. 2018-10-11), and Carreira (Comprehensive Chirality, 2012, Ed. Carreira, Elsevier Science, 5648 pages. TOC and chapters 3.9 and 3.25 provided - 62 pages).
Regarding claim 1, Brown (equivalent to the ‘061 patent described in the instant specification) teaches the stereoselective synthesis of the same compound (E) with R1 as CH3 ([0202]-[0203]):
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where the aldehyde reactant corresponds to claim 1 compound D, (1R,2S)-2-morpholino-1-phenylpropan-1-ol is equivalent to claim 1 compound C, and divinylzinc which was prepared by the Brubaker process of admixing CH2=CH-MgBr and ZnCl2 at 23C (“Divinylzinc solution (605 mL, 182 mmol; prepared according to Brubaker, J. D.; Myers, A. G. Org. Lett. 2007, 9, 3523-3525” – Brubaker pages S2-S4:
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at 23C in ethyl ether and THF) corresponding to claim 1’s
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wherein X1 is MgCl, zinc chloride corresponding to claim 1’s Zn(X3)2 wherein X3 is Cl, and ethyl ether / THF corresponding to the organic solvent. Brown teaches solvent of toluene and amounts of D (107 mmol); C-equivalent (182 mmol); divinylzinc (182 mmol). The ratios taught by Brown are equivalent (amounts used from Brubaker not disclosed) to D:
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of 1:1.7; D:Zn(X3)2 of 1:1.7; D:C of 1:1.7. Brown also teaches the reaction was maintained at minus 5C before quenching.
Thus, the reaction differs from the instant claim 1 by the chiral ligand (auxiliary), particular ratios and temperature.
Harrington teaches Example 18 ([0700]), including step 8 ([0708]) which starts with the same aldehyde reactant as Brown to prepare the vinyl alcohol product. Harrington teaches in step 8 the use of “(-)-cinchonidine” corresponding to claim 1’s Compound C wherein R2 is H; vinylmagnesium chloride corresponding to claim 1’s
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wherein X1 is MgCl; zinc chloride corresponding to claim 1’s Zn(X3)2 wherein X3 is Cl; and PhMe/THF corresponding to the organic solvent. Harrington teaches D ([0707]: 97 mmol) : CH2=CHX1 ([0708]: 329 mmol) ratio of 1:3.4; D ([0707]: 97 mmol) :Zn(X3)2 ([0708]: 155 mmol) ratio of 1.6; and D ([0707]: 97 mmol) : C ([0708]: 19.34 mmol) ratio of 1:0.2. Harrington teaches the reaction was warmed to 0C.
Brubaker also teaches the same transformation (addition of vinyl to aldehyde) using two alternative reactions with first one being stereoselective using divinylzinc, scheme 2:
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and the second alternative prep producing racemic mixture from vinylMgBr (p. S5):
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. As stated above, Brubaker teaches the process of admixing CH2=CH-MgBr and ZnCl2 at 23C to prepare the divinylzinc reagent (p. S2-S4:
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at 23C in ethyl ether and THF).
Carreira is a reference work on organic synthesis of chiral compounds and teaches the use of chiral auxiliaries (ligands) such as cinchona alkaloids to control the stereochemistry in a variety of reactions and varied ratios of reagents including stoichiometric (p. 227: “These reactions are stoichiometric in alkaloid, which is used to control the asymmetric induction of the desired reaction.”). Carreira reviews the use of chiral auxiliaries when performing addition reactions to carbonyl compounds including the use of vinylzinc reagents (p. 781-786). Carreira teaches the successful use of zinc reagents in addition reactions across a range of temperatures including room temperature and 23C (p. 781-786). Carreira teaches enantioselective reactions using cinchonine as a chiral auxiliary (p. 223-243, 793) as well as (1R,2S)-2-morpholino-1-phenylpropan-1-ol (p. 790 “Ligand 26”).
One of ordinary skill in the art in organic synthesis following the teaching of Brown for the synthesis of compound (E) would have considered the teaching of Brubaker (cited by Brown and teaching two alternative syntheses), Harrington (teaching an alternative synthesis of the same compound and using (-)-cinchonidine), and the well-known techniques known to those of ordinary skill in the art taught by Carreira and used the alternative chiral auxiliary of cinchonidine. One of ordinary skill in the art would have had a reasonable expectation of success because the same chiral auxiliary was successfully used in an alternative reaction of Harrington and was known to be interchangeable as taught by Carreira. One of ordinary skill in the art would have also considered optimization of the ratio of reactants and temperature of reaction as these elements are taught by the art to be varied across a range and are routinely optimized by those of ordinary skill in the art to maximize yield of the reactions. Thus, claim 1 is prima facie obvious.
Regarding claims 2-4, 7-8, and 13, Brown teaches R1 is methyl and X1 is MgBr while Harrington teaches R2 is H, and X1 is MgCl. One of ordinary skill in the art would have readily selected from among these known equivalent alternatives with a reasonable expectation of success and arrived at the claimed invention.
Regarding claims 5-6, although Harrington teaches the use of the chiral agent “(-)-cinchonidine” corresponding to Compound C when R2 is H, Harrington does not teach R2 is methoxy.
However, Carreira teaches that chinchona alkaloids are a well-known class of chiral auxiliaries used to control the stereochemistry of products, including that cinchonidine and quinine are useful for the same purpose as per Figure 1 (p. 223-228):
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.
Thus, one of ordinary skill in the art would have reasonably considered utilizing quinine in place of Harrington’s cinchonidine and arrived at the claimed invention with a reasonable expectation of success.
Regarding claim 18, Brown teaches purging with argon ([0202]).
Regarding claims 19-20, Brown teaches preparing divinylzinc in diethyl ether as per Brubaker.
Regarding claim 21, Brown does not specifically teach acetonitrile as a solvent in the particular reaction, but does teach the solvent in related reactions ([0194]-[0195]) as does Harrington ([0706]).
Regarding claim 23-26, Brown teaches admixing the chiral ligand divinylzinc and adding compound D to form E, while Harrington teaches admixing “(-)-cinchonidine” with zinc chloride, and adding vinylmagnesium chloride in THF at -13C. One of ordinary skill in the art would consider rearranging steps to improve the process and increase yield.
Regarding claim 27, Harrington teaches the temperature of the vinylmagnesium chloride as -13C, but not -10C.
Regarding claim 28, Harrington teaches warming temperature of the reaction to 0C, but not 10C, while Brubaker teaches warming to 23C.
Regarding claims 29 and 30, Brown and Harrington teaches the compound D is in PhMe, not acetonitrile. However, these references teach the use of MeCN in related reactions.
Regarding claim 32, Harrington teaches D ([0707]: 97 mmol) : CH2=CHX1 ([0708]: 329 mmol) ratio of 1:3.4.
Regarding claims 34, D ([0707]: 97 mmol) :Zn(X3)2 ([0708]: 155 mmol) ratio of 1.6.
Regarding claims 36, D ([0707]: 97 mmol) : C ([0708]: 19.34 mmol) ratio of 1:0.2.
Regarding claim 37-52, Harrington teaches Step 7 ([0707]):
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Regarding claim 53-56, 58, 60-62, and 65, Brown teaches Step 21 ([0205]) corresponding to the same hydrolyzying step, Harrington teaches admixing compound E and LiOH (~97mmol:387mmol) in water; in MeOH (claim 58); room temperature (claim 60); the product is formed as a Li+ salt (claims 61-62, 65).
Regarding claim 57, Brown teaches the ratio of 1:2 ([0205]: 9.52:19.05) and Harrington teaches including admixing compound E and LiOH (~97mmol:387mmol) in water, but does not teach the ratio of E:OH is 1:3.
Regarding claim 59, Brown and Harrington teaches the solvent is methanol, but not ethanol.
Regarding claim 72, Brown and Harrington teach the use of an inert atmosphere of argon in air sensitive reactions, but not in the particular reaction step as in the claim.
Regarding claims 73-74, Brown teaches Example 4 ([0310]) which is the same compound as A1 and Harrington teaches General method 1 ([0629]) which forms the following compound:
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, in the process of producing the final compound of example 18 (Harrington claim 42 – same as instant A2), such that one of ordinary skill in the art would have following Harrington’s teaching of methods to make the same compound via the overall synthetic process and arrive at the claimed invention.
In each of the above claims, Brown and Harrington teaches similar reaction conditions that differ from the claims in a manner that one of ordinary skill in the art would consider part of routine optimization, such as solvent selection, temperature of reaction, inert atmosphere, and ratio of reactants all of which are typically optimized to increase yield and reduce side reactions. Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. “[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); MPEP 2144.05.
Claims 9-12, 14-17 are rejected under 35 U.S.C. 103 as being unpatentable over Brown et al. (US20160068545) in view of Brubaker et al. (Org. Lett. 2007, 9, 18, 3523–3525), Harrington et al. (US20180289720, publ. 2018-10-11), and Carreira (Comprehensive Chirality, 2012, Ed. Carreira, Elsevier Science, 5648 pages. TOC and chapters 3.9 and 3.25 provided - 62 pages) as applied to claims 1-8, 13, 18-21, 23-30, 32, 34, 36-62, 65, 72-74 above and further in view of Braun et al. ("2.12 Selected Diastereoselective Reactions: Additions of Achiral Carbanions to Chiral Aldehydes and Ketones," in Comprehensive Chirality, Editor: Carreira and Yamamoto; Elsevier, 2012, Pages 346-369.) and Silverman et al. (Handbook of Grignard Reagents, CRC Press, 1996, Chapters 1-4 and 17, 117 pages).
Regarding claims 9-12, although Brown teaches X1 is MgBr and Harrington teaches the use of vinylmagnesium chloride corresponding to claim 1’s
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wherein X1 is MgCl, the references do not teach Li (claim 9), CuLi (claim 10), InI (claim 11), or ZnBr (claim 12). Regarding claims 14-17, Harrington teaches ZnCl2, but does not teach other anions.
However, Braun and Silverman teach a variety of well-known organometallic reagents for addition to a carbonyl to form an alcohol product including MgBr, Li, CuLi, ZnBr, indium (Braun; Silverman p. 67) as well as ZnBr2. One or ordinary skill in the art routinely uses such well-known organometallic reagents interchangeably to optimize yield and stereochemistry. In addition, one of ordinary skill in the art would have an expectation that the Cl, Br, and I would behave similarly when interchanged due to their belonging to the art-recognized family of halogens. Thus, one of ordinary skill in the art would have reasonably considered utilizing MgBr, Li, CuLi, ZnBr, indium in place of Brown or Harrington’s X1 and arrived at the claimed invention with a reasonable expectation of success.
Claims 63-64 and 66-71 are rejected under 35 U.S.C. 103 as being unpatentable over Brown et al. (US20160068545) in view of Brubaker et al. (Org. Lett. 2007, 9, 18, 3523–3525), Harrington et al. (US20180289720, publ. 2018-10-11), and Carreira (Comprehensive Chirality, 2012, Ed. Carreira, Elsevier Science, 5648 pages. TOC and chapters 3.9 and 3.25 provided - 62 pages) as applied to claims 1-8, 13, 18-21, 23-30, 32, 34, 36-62, 65, 72-74 above and further in view of Juaristi et al. (Tetrahedron: Asymmetry 9 (1998) 715–740).
Regarding claims 63-64 and 66-71, Brown ([0205]) and Harrington teaches the formation of the same free acid of Compound F (instant claim 53), but does not teach the formation of a salt with the cation of claim 64. However, Juaristi teaches use of alpha- phenethylamine as a chiral resolution agent (p. 729-736), which is a well-known technique in the art that has been successfully applied to separate chiral compounds. Harrington’s compound is a comparable compound to those of Juaristi’s such that a salt resolution technique would be expected to achieve the same result. Thus, the application of the same technique is obvious, including finding the optimal workable range of molar ratios to ensure salt formation. MPEP 2143.
Response to Applicant Remarks - 35 USC § 103
Applicant argues that there was no teaching, suggestion, or motivation for making any modification to the reaction conditions, including the temperature range of 10-35C. This argument is not persuasive because Brown and Harrington teach a close range and Brubaker and Carreira teaches a wide range of temperatures that one of ordinary skill in the art would have considered given the success shown in similar reactions.
Applicant argues that Ager teaches away from the claimed invention due to “other chiral ligands are better suited”. This argument is not persuasive because this quote expresses a preference and would not be considered a clear teaching away from the ligand, particularly because of the success shown with the ligand in related contexts. As per MPEP 2145: “the prior art’s mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed….” In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004). See also UCB, Inc. v. Actavis Labs, UT, Inc., 65 F.4th 679, 692, 2023 USPQ2d 448 (Fed. Cir. 2023) (“a reference does not teach away if it merely expresses a general preference for an alternative invention but does not criticize, discredit or otherwise discourage investigation into the invention claimed.”) (internal quotations omitted) (quoting DePuy Spine, Inc. v. Medtronic Sofamor Danek, Inc., 567 F.3d 1314, 1327 (Fed. Cir. 2009)).
Harrington and Brown does teach using synthetic “methods known to those skilled in the art” as described in the numerous publications cited and incorporated by reference and which are well-known to those of ordinary skill in the art. In addition, the references teach “the compounds of this invention can be synthesized, and various modifications to these methods can be made and will be suggested to one skilled in the art” (Brown [0590]; Harrington [0626]). For example, Harrington also suggests ranges of reaction conditions ([0627]) which one of ordinary skill in the art would have considered part of routine experimentation. In addition, the solvent selection, temperature of reaction, inert atmosphere, and ratio of reactants are all modification which are typically made by one of ordinary skill in the art to increase yield and reduce side reactions. Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. “[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); MPEP 2144.05.
An improvement in the art would have been obvious if “it is likely the product not of innovation but of ordinary skill and common sense.” KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 421 (2007). Finding workable or optimal ranges is generally understood as within the capabilities of the ordinary artisan. See Pfizer Inc. v. Apotex Inc., 82 USPQ2d 1321 (Fed. Cir. 2007) (discovery of an optimum value of a variable in a known process is usually obvious.). The idea that optimizing an ordinary variable does not by itself constitute a patentable advance was also stated in In re Geisler, 43 USPQ2d 1362: “…“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). Only if the “results of optimizing a variable” are “unexpectedly good” can a patent be obtained for the claimed critical range. In re Antonie, 559 F.2d 618, 620, 195 USPQ 6, 8 (CCPA 1977); see also In re Dillon , 919 F.2d 688, 692, 16 USPQ2d 1897, 1901 (Fed.Cir. 1990) (in banc).” Note MPEP §2144.05(II)(A) on this issue. Likewise, optimization of a range or other variable within the claims flows from the “normal desire of scientists or artisans to improve upon what is already generally known.” In re Peterson, 65 USPQ2d 1379, 1382. See also In re Boesch, 617 F.2d 272, 276 (C.C.P.A. 1980): “[D]iscovery of an optimum value of a result effective variable in a known process is ordinarily within the skill of the art.”; In re Esterhoy, 440 F.2d 1386, 1389 (C.C.P.A. 1971): “The conditions recited in the claims appear to us to be only optimum and easily ascertained by routine experimentation.”; In re Swentzel, 219 F.2d 216, 219 (C.C.P.A. 1955): “the determination of that desired size under the present circumstances involves nothing more than routine experimentation and exercise of the judgment of one skilled in the art.”; In re Swain, 156 F.2d 246, 247-48 (C.C.P.A. 1946): “In the absence of a proper showing of an unexpected and superior result over the disclosure of the prior art, no invention is involved in a result obtained by experimentation.” See also In re Kulling, 14 USPQ2d 1056 and In re Malagari, 182 USPQ 549, 553.
Moreover, In re Huang, 40 USPQ2d 1685, 1688 states that even if the “modification results in great improvement and utility over the prior art, it may still not be patentable if the modification was within the capabilities of one skilled in the art, unless the claimed ranges “produce a new and unexpected result which is different in kind and not merely in degree from the results of the prior art.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (C.C.P.A. 1955); see In re Woodruff, 919 F.2d 1575, 1578, 16 USPQ2d 1934, 1936-37 (Fed.Cir. 1990).” Note similar language in In re Waymouth and Koury, 182 USPQ 290 (“a difference in kind, rather than in degree.”).
In this case the prior art teaches similar solvents, temperature of reaction, inert atmosphere, and ratio of reactants that are within a scope that one of ordinary skill in the art would consider in routine optimization such that a prima facie case of obviousness has been established and Applicant has not shown unexpected results or criticality of the claim elements.
New Double Patenting
Claims 1-30, 32, 34, 36-74 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 20 of U.S. Patent No. 10300075. Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of the patent are to the some compound of instant claim 74 and one of ordinary skill in the art interpreting and construing the claims of the patent would need to look to the same part of the specification (Harrington et al., US20180289720, shares the same specification) and as detailed in the above 103 rejections over the cited references and incorporated herein would find the instant claims obvious.
Claims 1-30, 32, 34, 36-74 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 and 2 of U.S. Patent No. 12091425 in view of references cited in the 35 USC 103 rejections supra. Although the claims at issue are not identical, they are not patentably distinct from each other because in the course of synthesizing the compound of patent claim 20, one of ordinary skill in the art interpreting and construing the claims of the patent would need to look to the specification of Harrington (Example 18, steps 12-13) and find the same compound and as detailed in the above 102 and 103 rejections over the cited references and incorporated herein would find the instant claims obvious.
Claims 1-30, 32, 34, 36-74 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 38 of U.S. Patent No. 10821115 in view of references cited in the 35 USC 103 rejections supra. Although the claims at issue are not identical, they are not patentably distinct from each other because in the course of synthesizing the compound of patent claim 38 ([1956]) which is the same as that of instant claim 74, one of ordinary skill in the art would need to look to the specification of Harrington (Example 18) and find the same compound and as detailed in the above 103 rejections over the cited references and incorporated herein would find the instant claims obvious.
Claims 1-30, 32, 34, 36-74 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 38 of U.S. Patent No. 10632128 in view of references cited in the 35 USC 103 rejections supra. Although the claims at issue are not identical, they are not patentably distinct from each other because in the course of synthesizing the compound of patent claim 38 ([1795]) which is the same as that of instant claim 74, one of ordinary skill in the art would need to look to the specification of Harrington (Example 18) and find the same compound and as detailed in the above 103 rejections over the cited references and incorporated herein would find the instant claims obvious.
Claims 1-30, 32, 34, 36-74 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 27 of U.S. Patent No. 10500213 in view of references cited in the 35 USC 103 rejections supra. Although the claims at issue are not identical, they are not patentably distinct from each other because in the course of synthesizing the compound of patent claim 38 ([1910]) which is the same as that of instant claim 74, one of ordinary skill in the art would need to look to the specification of Harrington (Example 18) and find the same compound and as detailed in the above 103 rejections over the cited references and incorporated herein would find the instant claims obvious.
Claims 1-30, 32, 34, 36-74 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 20 of U.S. Patent No. 10300075 in view of references cited in the 35 USC 103 rejections supra. Although the claims at issue are not identical, they are not patentably distinct from each other because in the course of synthesizing the compound of patent claim 20 ([1986]) which is the same as that of instant claim 74, one of ordinary skill in the art would need to look to the specification of Harrington (Example 18) and find the same compound and as detailed in the above 103 rejections over the cited references and incorporated herein would find the instant claims obvious.
Claims 1-30, 32, 34, 36-74 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 2 of U.S. Patent No. 9562061 in view of references cited in the 35 USC 103 rejections supra. Although the claims at issue are not identical, they are not patentably distinct from each other because in the course of synthesizing the compound of patent claim 2 which is the same as that of instant claim 73, one of ordinary skill in the art would need to look to the specification of Harrington (Example 18) and find the same compound and as detailed in the above 103 rejections over the cited references and incorporated herein would find the instant claims obvious.
Response to Applicant Remarks – Double Patenting
Applicant references the above argument and are not persuasive for the same reasons above. Thus, the rejections are maintained.
Conclusion
No claim allowed.
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/ROBERT H HAVLIN/Primary Patent Examiner, Art Unit 1626