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 1-9 of G. Hodges et al., App. No. 18/550,336 (Jun. 8, 2021) are pending. Claims 2, 3, 7, and 9 are rejected. Claims 1, 4-6 and 8 are in condition for allowance subject to the specification objections.
Objections to the Specification
The specification is objected to on the grounds that, in every instance, the structures of 2-chloroacroleins, 2-chloropropenols and chloroacetyl chloride are incorrectly depicted throughout the specification where the intended chloro group is incorrectly drawn as a methyl group.
For example, compounds 3 and 4 are incorrectly depicted with a methyl group at claim 1, formula (III) variable R3 as follows:
PNG
media_image1.png
200
400
media_image1.png
Greyscale
Specification at page 5, Scheme 1(a).
Here, it is clear from the specification that compounds 3 and 4 should be drawn where the above formula (III) R3 methyl group is, per claim 1 hydrogen or halogen, for example chloro as depicted by the Examiner below:
PNG
media_image2.png
200
400
media_image2.png
Greyscale
The specification clearly indicates to one of skill that the subject R3 methyl group is incorrectly drawn. See e.g., specification at page 16 (“Scheme 7 Scheme 7: Oxidation of 2-chloropropenol to 2-chloroacrolein”). See also, specification working examples at pages 8-16 (all employing 2-chloroacrolein, where no working example employs incorrectly drawn compounds 3 or 4). As additional evidence, as seen from specification, Scheme 1(a), the final product (i.e., (S)-NAA) does not contain the methyl group that would result from of condensation of formula 5 with incorrectly drawn formula 4 followed by loss of H2O and HCl. Specification at page 5, Scheme 1(a).
It is likely that the incorrectly drawn 2-chloroacroleins and 2-chloropropenols (such as, compounds 3 and 4) resulted from a copy and paste error.
Correction of all such structures throughout the specification is required. For example, even page 1 incorrectly omits the chloro group in the depicted scheme (that is each of chloroacetyl chloride; S-MOC; and rac-metolachlor are all incorrectly drawn — methyl versus chloro).
Rejections 35 U.S.C. 112(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.
Pursuant to 35 U.S.C. 112, the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). The meaning of every term used in a claim should be apparent from the prior art or from the specification and drawings at the time the application is filed. Claim language may not be ambiguous, vague, incoherent, opaque, or otherwise unclear in describing and defining the claimed invention. MPEP § 2173.05(a).
Indefinite Structure Claim 3
Claim 3 is rejected pursuant to 35 U.S.C. 112, as indefinite because reaction of the claim 3 compound of formula (III):
PNG
media_image3.png
200
400
media_image3.png
Greyscale
is not taught by the specification as giving the product of formula (I), per base claim 1.
As seen from specification, Scheme 1(a), the final product (i.e., (S)-NAA):
PNG
media_image4.png
200
400
media_image4.png
Greyscale
does not contain the methyl group that would result from of condensation of the claim 3 compound, followed by loss of H2O and HCl. Specification at page 5, Scheme 1(a). Claim 3 is unclear because it is in conflict with the specification and also because the synthetic method of claim 3 requires the chemically unfavored elimination of a methyl group to form a double bond (where the specification contains no guidance or teachings respecting such methyl group elimination).
As noted in the specification objection above, it appears that the subject claim 3 structure is incorrectly drawn and a chloro group was intended at variable R3. Thus, simply amending to change the above methyl to chloro would obviate this rejection.
Indefinite Structure Claim 2
Claim 2 is rejected pursuant to 35 U.S.C. 112, as indefinite because the attachment of R1 and R2 in formula (III) is unclear. Claim 2 recites:
2. The method of claim 1, wherein R3 is Cl or Br; and
R1 and R2 are each independently dimethoxy, diethoxy, ethylene glycol, or
R1 and R2 together are =O.
First, the plain meaning of “independently” in the context of claim 2 is that each of R1 and R2 are separate groups rather than the case where R1 and R2 are a single group joined to form a ring, such as the cyclic acetals of -OCH2CH2O- or -OCH2CH2CH2O- (ethylene glycol and propylene glycol) as per claim 1.
The issue is that the structural meaning of “independently dimethoxy, diethoxy, ethylene glycol” in the context of claim 2 is unclear. For example, under a plain meaning interpretation, a compound of claim 2 formula (III), where R1 is dimethoxy and R2 is ethylene glycol is the following:
PNG
media_image5.png
200
400
media_image5.png
Greyscale
MPEP § 2111.01(III). However, an alternate reasonable interpretation of dimethoxy and ethylene glycol as R1 and R2 alternatives are the following compounds
PNG
media_image6.png
200
400
media_image6.png
Greyscale
This interpretation is reasonable because it follows statutory requirement (§112(d)) that dependent claim 2 falls within the scope of its base claim. This interpretation is also more consistent with the specification than the above plain meaning interpretation. See specification at page 24 (Scheme 15).
Since claim 2 is subject to multiple structural interpretations, it is unclear to one of skill which structures of formula (III) meet the limitations of claim 2. MPEP § 2173.
This rejection can be overcome, for example, by amending claim 2 as follows.
2. The method of claim 1, wherein R3 is Cl or Br; and
R1 and R2 are each independently methoxy or ethoxy, or R1 and R2 together are -OCH2CH2O-,
R1 and R2 together are =O.
Claim Objections
Claim 7 is objected to on the grounds that it recites “of any of claim 1”, where the words “of any” should be deleted by amendment since claim 7 is dependent upon only a single claim.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), 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.
§ 112(d) Rejection of Claim 2
Claim 2 is rejected under 35 U.S.C. 112(d) 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 for the following reasons.
As discussed in the § 112(b) rejection above, under one interpretation, a compound of claim 2 formula (III), where R1 is dimethoxy and R2 is ethylene glycol is the following:
PNG
media_image5.png
200
400
media_image5.png
Greyscale
However, this compound falls outside the scope of claim 1 and claim 2 therefore fails to further limit the subject matter of claim 1 upon which it depends.
§ 112(d) Rejection of Claim 3
Claim 3 is rejected under 35 U.S.C. 112(d) 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 for the following reasons.
Claim 3 recites that “wherein the compound of formula (III) is
”
PNG
media_image7.png
200
400
media_image7.png
Greyscale
However, the above compound of formula (III) has a methyl group at claim 1 variable R3. Claim 1 does not permit variable R3 to be methyl. As such, the scope of claim 3 falls outside the scope of claim 1 and claim 3 fails to further limit the subject matter of claim 1 upon which it depends.
As noted in the specification objection above, it appears that the subject claim 3 structure is incorrectly drawn and a chloro group was intended at variable R3. Thus, simply amending to change the above methyl to chloro would obviate this rejection.
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 J. Li et al., US 2014/0018548 (2014) (“Li”)
Claims 7 is rejected under 35 U.S.C. 102(a)(1)/(2) as being anticipated by J. Li et al., US 2014/0018548 (2014) (“Li).
In working Example 12, Li teaches synthesis of (S)-2-chloro-N-(2’-Ethyl-6'-methylphenyl)-N-(2-methoxyl-1-methylethyl)acetamide (i.e., (S)-metolachlor) by reaction of (S)-N-(2-ethyl-6-methylphenyl)-N-(1-methoxylmethyl)ethylamine with chloroacetyl chloride, which is summarized by the Examiner as follows:
PNG
media_image8.png
200
400
media_image8.png
Greyscale
Li working Example 12 meets each and every limitation of claim 7. It is true that Li does not teach “where the compound of formula (I) was produced by the method of any of claim 1”. However, this is not a patentable distinction. Claim 7 is clearly claimed using “product by process language “nested” within a method claim:
Claim 7 . . . where the compound of formula (I) was produced by the method of any of claim 1 . . .
While the scope of a product-by-process claim for infringement purposes is limited by the process, when determining patentability, the claim is considered only in view of the resulting product. MPEP § 2113(I); see also, Amgen Inc. v. F. Hoffman-La Roche Ltd., 580 F.3d 1340, 1370 n.14 (Fed. Cir. 2009). Thus, 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). Here, the product-by-process limitation is nested within a method claim; however, this does not change the analysis. Biogen MA Inc. v. EMD Serono, Inc., 976 F.3d 1326, 1334 (Fed. Cir. 2020) (“[t]he nesting of the product-by-process limitation within a method . . . claim does not change the proper construction of the product-by-process limitation itself . . . [a]n old method of administration of an old product made by a new process is not novel and cannot be patented”); see also non-binding, non-precedential board opinions in Ex parte Wohaibi, Appeal No. 2024-004112, 17/750,212 (PTAB 2025) and Ex parte Yang, Appeal No. 2025-000566, 17/587,166 (PTAB 2025) discussing and applying Biogen MA Inc. v. EMD Serono, Inc..
Here, there is no apparent difference between Li’s (S)-N-(2-ethyl-6-methylphenyl)-N-(1-methoxylmethyl)ethylamine and the compound of formula (I) depicted in claim 7 that was prepared by the method of claim 1. As such, Li meets each and every patentable limitation of claim 7.
§ 102(a)(1)/(2) Rejection over R. Bader et al., US 5,430,188 (1995) (“Bader”)
Claims 9 is rejected under 35 U.S.C. 102(a)(1)/(2) as being anticipated by R. Bader et al., US 5,430,188 (1995) (“Bader”). In Example 2, Bader teaches synthesis of 2-ethyl-6-methyl-N-(1'-methoxy-2'-propyl)-N-chloracetanilide by rection of 2-ethyl-6-methyl-N-(1'-methoxy-2'-propyl)-aniline with chloracetylchloride, which is summarized by the Examiner as follows:
PNG
media_image9.png
200
400
media_image9.png
Greyscale
Bader at col. 5, lines 49-65 (Example 2).
Claim 9 is clearly claimed using nested product by process language:
Claim 9 . . . where the compound of formula (IV) was produced by the
method of claim 8 . . .
Here, there is no apparent difference between Bader’s 2-ethyl-6-methyl-N-(1'-methoxy-2'-propyl)-aniline and the compound of formula (IV) depicted in claim 9 that is prepared by the method of claim 8. As such, Bader meets each and every patentable limitation of claim 9 for the same reasons discussed above for claim 7.
Non-Statutory Double Patenting Rejections
The non-statutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A non-statutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
Provisional Non-Statutory Double Patenting Rejection over R. Hodges, US 18/551,880 (2022), published as US 2024/0190813 (2024)
Claims 1-9 are provisionally rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claims 1 and 2 of R. Hodges, US 18/551,880 (2022), published as US 2024/0190813 (2024). The instant and conflicting claims have the same patent term filing date. However, the rejection is provisional because the conflicting claims have not been patented.
Conflicting claims 1 and 2 respectively claim the following compounds (I) and (Ia):
PNG
media_image10.png
200
400
media_image10.png
Greyscale
(I) (Ia)
These compounds are reactants of instant independent method claims 1 and 8 (i.e., instant formulae (II) and (V)). The conflicting specification teaches the present technology is useful in production of chemicals known as starting materials for herbicides the S-Metolachlor (S-MOC) and metolachlor. See US 2024/0190813 (2024) at page 1, [0002]. The conflicting specification further teaches that compounds (I) and (1a) are useful to produce (S)-NAA (claim 1 formula (I)) according to the same method as instantly claimed.
PNG
media_image11.png
200
400
media_image11.png
Greyscale
US 2024/0190813 (2024) at page 1, [0004].
Those portions of the specification which provide support for the conflicting claims may be examined and considered when addressing the issue of whether a claim in the application defines an obvious variation of an invention claimed in the reference patent or application. MPEP § 804(II)(B)(1) (citing In re Vogel, 422 F.2d 438, 441-42, 164 USPQ 619, 622 (CCPA 1970)). The court in Vogel recognized ‘that it is most difficult, if not meaningless, to try to say what is or is not an obvious variation of a claim,’ but that one can judge whether or not the invention claimed in an application is an obvious variation of an embodiment disclosed in the patent or application which provides support for the claim. MPEP § 804(II)(B)(1). In this regard, it is also proper to look at the disclosed utility in the reference disclosure to determine the overall question of obviousness in a nonstatutory double patenting context. MPEP § 804(II)(B)(1) (citing AbbVie Inc. v. Kennedy Institute of Rheumatology Trust, 764 F.3d 1366, 112 USPQ2d 1001 (Fed. Cir. 2014); Sun Pharm. Indus., Ltd. v. Eli Lilly & Co., 611 F.3d 1381, 95 USPQ2d 1797 (Fed. Cir. 2010); Pfizer, Inc. v. Teva Pharm. USA, Inc., 518 F.3d 1353, 86 USPQ2d 1001 (Fed. Cir. 2008); Geneva Pharmaceuticals Inc. v. GlaxoSmithKline PLC, 349 F3d 1373, 1385-86, 68 USPQ2d 1865, 1875 (Fed. Cir. 2003)).
US 18/551,880 specification’s disclosed utility and specification portions that provide support for compounds (I) and (Ia) teach that their only use is as reactants to produce (S)-NAA or racemic NAA (which in turn can be converted to (S)-metolachlor or racemic metolachlor) according the same method claimed in instant claims 1 and 8. Here, properly considering the conflicting specification’s disclosed utility, instant method claims 1-9 are patentably indistinct from (an obvious variation of) conflicting claims 1 and 2 because instant claims 1-9 recite a method directed to the only disclosed use for the compounds of conflicting claims 1 and 2.
As noted in Sun Pharm. Indus., Ltd. v. Eli Lilly & Co, the holding of Geneva and Pfizer, that a ‘claim to a method of using a composition is not patentably distinct from an earlier claim to the identical composition in a patent disclosing the identical use,’ extends to any and all such uses disclosed in the specification of the earlier patent; indeed, both cases recognized,
[i]t would shock one's sense of justice if an inventor could receive a patent upon a composition of matter, setting out at length in the specification the useful purposes of such composition, . . . and then prevent the public from making any beneficial use of such product by securing patents upon each of the uses to which it may be adapted.
Sun Pharm. Indus. v. Eli Lilly & Co., 611 F.3d 1381, 1387 (citations omitted).
The Examiner notes that Sun, Geneva and Pfizer involved the specific factual framework of claimed method of using a pharmaceutical compound/composition versus a conflicting claim to the compound itself. However, the legal concept is applicable here (in non-pharmaceutical context) where the examined claims are directed to the only disclosed method of using the conflicting claim’s composition of matter.
Terminal Disclaimer
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Subject Matter Free of the Art of Record
Subject to the § 112 and double patenting rejections, claims 1-6 and 8 are free of the art of record.
It is first noted that claim 1 draws only one the (S)-enantiomer of formula (I) but does not specify a particular optical purity. The specification teaches that the (S)-enantiomer of metolachlor (i.e., (S)-metolachlor) is approximately twenty times more active than the (R)-enantiomer. Specification at page 1, lines 2-3. The specification further teaches that starting from enantiomerically pure formula (II) (i.e., chiral (S)-1-methoxy-2-propylamine (99% e.e.), analysis of the chiral reaction showed only one enantiomer, corresponding to (S)-imine of formula (I). Specification at page 22. In view of claim 1’s drawing of only a single enantiomer in the more preferred (S)-configuration, the broadest reasonable interpretation of claim 1, consistent with the specification, is that claim 1 requires use of the (S) enantiomer of formula (II) in some enantiomeric excess over the racemic mixture. MPEP § 2111. Thus, for example, one of skill practicing claim 1 with racemic formula (II) would not infringe claim 1. One the other hand, one of skill practicing claim 1 with formula (II) enriched in the (S)-enantiomer would infringe claim 1.
The closest art of record is T. Neves et al., WO 2016/153374 (2016) (“Neves”). Neves teaches the following synthesis of (S)-metolachlor, where instantly claimed formula (I) (also referred to in the art as (S)-NAA) is prepared in a first condensation of methoxyacetone with the aniline, followed by asymmetric hydrogenation.
PNG
media_image12.png
200
400
media_image12.png
Greyscale
Neves at page 1, lines 15-20. Neves differs from claims 1 and 8 in the identity of reactants used to prepare NAA. That is, Neves does not teach the claim 1 cyclo-condensation of formula (II) with formula (III) or the corresponding claim 8 racemic version.
The closest prior art to the instant claim 1 cyclo-condensation of formula (II) with formula (III) (and the corresponding claim 8 racemic version) is N. De Kimpe, Acetone cyclohexylamine, in e-EROS Encyclopedia of Reagents for Organic Synthesis, 1-4 (2001) (“De Kimpe”).
De Kimpe teaches that direct condensation of excess acetone N-isopropylimine with methyl vinyl ketone is a suitable method for the synthesis of 3-methyl-2-cyclohexenone via subsequent Michael addition, intramolecular aldol condensation, and hydrolysis (eq 21).
PNG
media_image13.png
200
400
media_image13.png
Greyscale
De Kimpe at page 3, col. 1 (citing eq. 21). However, motivation to combine De Kimpe with Bader and/or Li is lacking and the direct combination still fails to teach the claim 1 reaction. In fact, claim 1 formula (II) (and its claim 8 racemic version) appears to be novel. As such, independent claims 1 and 8 (and their dependents) are not obvious in view of the above cited art.
Conclusion
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