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 .
Claims 41 and 94-110 are currently pending. Claim 41 is independent.
Priority
Applicant claims priority benefit as follows:
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.
Election/Restrictions
Applicant’s election without traverse of Group IV, claim 41 and new claims 94-110, in the reply filed on 09/30/2025 is acknowledged. Applicant’s election of species of compound of formula (I)
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and of starting material being an amidine, is also acknowledged. The elected species reads on claims 41, 94-98, 101-102 and 105
All claims drawn to a nonelected inventions have been canceled.
Examination
Examination will begin with the elected species. In accordance with MPEP 803.02, the Markush claim will be examined fully with respect to the elected species and further to the extent necessary to determine patentability. Note that where a claim reads on multiple species, only one species needs to be taught or suggested by the prior art in order for the claim to be anticipated or rendered obvious. If on examination the elected species is found to be anticipated or rendered obvious by prior art, the Markush claim and claims to the elected species will be rejected, and claims to the nonelected species will be held withdrawn from further consideration. Should applicant, in response to a rejection of a Markush claim, overcome the rejection by amending the Markush claim to exclude the species anticipated or rendered obvious by the prior art, the amended Markush claim will be examined again. The examination will be extended to the extent necessary to determine patentability of the Markush claim. It should be noted that the prior art search will not be extended unnecessarily to cover all non-elected species.
Pursuant to MPEP 803.02, the elected species of amidine starting material and product of formula
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were searched and found unpatentable over the art as detailed below. Therefore, examination was stopped and art has been applied against the claims.
Claims 99-100, 103-104, 106-107 and 109-110 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 09/30/2025.
The entire scope of claims 41, 94-98, 101-102, 105 and 108 has not yet been examined in accordance with Markush search practice.
Specification Objection-abstract
Applicant is reminded of the proper content of an abstract of the disclosure.
With regard particularly to chemical patents, for compounds or compositions, the general nature of the compound or composition should be given as well as the use thereof, e.g., The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics. Exemplification of a species could be illustrative of members of the class. For processes, the reactions, reagents and process conditions should be stated, generally illustrated by a single example, unless variations are necessary. See MPEP § 608.01(b), Section B.
The abstract of the disclosure is objected to because it fails to exemplify any members or formulae illustrative of the elected invention. Correction is required. See MPEP § 608.01(b).
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph 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 the first paragraph of pre-AIA 35 U.S.C. 112:
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 41, 94-98, 101-102, 105 and 108 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 lack of written description rejection.
Vas-Cath Inc. V. Mahurkar, 19 USPQ2d 1111, states that Applicant must convey with reasonable clarity to those skilled in the art that, as of the filing date sought, he or she was in possession of the invention. The courts have stated:
“To fulfill the written description requirement, a patent specification must describe an invention and do so in sufficient detail that one skilled in the art can clearly conclude that "the inventor invented the claimed invention." Lockwood v. American Airlines, Inc., 107 F.3d 1565, 1572, 41 USPQ2d 1961, 1966 (1997); In re Gosteli, 872 F.2d 1008, 1012, 10 USPQ2d 1614, 1618 (Fed. Cir. 1989) (" [T]he description must clearly allow persons of ordinary skill in the art to recognize that [the inventor] invented what is claimed."). Thus, an applicant complies with the written description requirement "by describing the invention, with all its claimed limitations, not that which makes it obvious," and by using "such descriptive means as words, structures, figures, diagrams, formulas, etc., that set forth the claimed invention." Lockwood, 107 F.3d at 1572, 41 USPQ2d at 1966.” Regents of the University of California v. Eli Lilly & Co., 43 USPQ2d 1398.
To provide adequate written description and evidence of possession of a claimed genus, the specification must provide sufficient distinguishing characteristics of the genus. The factors to be considered include disclosure of complete or partial structure, physical and/or chemical properties, functional characteristics, structure/function correlation, methods of making the claimed product, or any combination thereof. A description of a genus may be achieved by means of a recitation of a representative number of species falling within the scope of the genus or of a recitation of structural features common to the members of the genus, which features constitute a substantial portion of the genus.
“The examples and description should be of sufficient scope as to justify the scope of the claims”. See MPEP § 608.01(p). If a representative number of adequately described species are not disclosed for a genus, the claim to that genus must be rejected as lacking adequate written description under 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, para. 1 (MPEP 2163).
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The species described in the specification are not a representative sample of the claimed genus. The specification doesn’t have support for compounds of formula (I) wherein
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represents a single bond, as the specification does not describe any species falling within this subgenus and how to make them. Further, it is clear that there is no description of such subgenus since a single bond would leave an open valence on the nitrogen atom. These compounds cannot exist.
In addition, the current claims recite that the starting material comprises any amidine. According to the IUPAC goldbook, the term “amidine” includes sulfinamidines (RS(=NR)NR) and phosphinamidines (R2P(=N)NR2). However, the specification has no description for how to make the compounds of formula
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(I) from sulfinamidines or phosphinamidines. Thus, the specification does not have support, and applicant was not in possession of the full scope of the claimed any “starting material comprising an amidine molecule”, reacting it simply with CS2 and converting into a compound of formula (I).
In addition, the reaction step that recites “converting” the dithiocarbamate compound to a compound of formula (I) covers any type or number of steps and conditions (including chemical and biochemical reactions). Even though the specification discloses examples of some of the reaction conditions, there is evidence in this application and in the art that some of the claimed reactions do not work. As evidence, paragraph [0288] shows that the reaction in claim 41 will not give the claimed product when the starting material amidine is formamidine or trifluoroacetamidine. Compounds prepared from these two starting amidines are being claimed in claim 102, however, they could not be prepared. The specification does not support their preparation as disclosed in the examined claims.
Also, the use of methyl bromoacetate (alkyl halide) in the claimed reaction did not give the product of formula (I). See Figure 6. Further, cyclic amidines do not produce the claimed product of formula (I), and there is no support in this application that would show that applicants made the cyclic amidine reactions work. See the reference Ang et al. (Eur. J. Org. Chem. 2015, 7334-7343).
In accordance with MPEP 2173.05 (g):
“Unlimited functional claim limitations that extend to all means or methods of resolving a problem may not be adequately supported by the written description or may not be commensurate in scope with the enabling disclosure, both of which are required by 35 U.S.C. 112(a) and pre-AIA 35 U.S.C. 112, first paragraph. In re Hyatt, 708 F.2d 712, 714, 218 USPQ 195, 197 (Fed. Cir. 1983); Ariad, 598 F.3d at 1340, 94 USPQ2d at 1167. For instance, a single means claim covering every conceivable means for achieving the stated result was held to be invalid under 35 U.S.C. 112, first paragraph because the court recognized that the specification, which disclosed only those means known to the inventor, was not commensurate in scope with the claim.”
A similar issue arises in these claims. Claims 41, 94-98, 101-102, 105 and 108 cover every conceivable means for achieving the stated result. However, the specification discloses only those means known to the inventor, which is not commensurate in scope with the claims.
Accordingly, it is deemed that the specification does not describe in sufficient detail the genus of compounds in the claims and how to use them and does not reasonably convey to one skilled in the relevant art that the inventor(s), at the time the application was filed, had possession of the entire scope of the claimed invention.
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 41, 94-98, 101-102, 105 and 108 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 applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 41 recites reacting “a starting material comprising an amidine … molecule”. A “starting material comprising an amidine molecule” is ambiguous. The artisan wouldn’t know what amidine molecules are and are not encompassed by the scope of the claims that would provide a compound of formula (I), since clearly not all kinds of amidines could give the claimed product of formula (I)
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. “Amidines” encompasses sulfinamidines (RS(=NR)NR) and phosphinamidines (R2P(=N)NR2), as discussed before. Thus, the scope of the amidine structures encompassed by the claimed process is unclear.
In claim 41, the compound of formula (I) contains a dashed bond from C to N
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. If the bond from C to N is a single bond, this makes the claim ambiguous because a nitrogen with only two substituents has an open valence and cannot exist.
Claims 41, 94-98, 101-102, 105 and 108 are ambiguous because these do not particularly point out and distinctly claim the subject matter which the applicant regards as his invention. Claim 41 recites reacting a starting material comprising an amidine with carbon disulfide to form a dithiocarbamate compound, and converting the dithiocarbamate to a compound of formula (I). Due to the components of the claimed reaction, the dithiocarbamate compound would have a similar structure to the following:
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. The claims require converting the dithiocarbamate compound into a compound of formula (I)
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. However, it is unclear where does Z-R2 come from, and how does a sulfur atom from the dithiocarbamate become replaced by an oxygen atom in variable X. The claims do not put forward the process steps and reagent/conditions for “converting” the dithiocarbamate to a compound of formula (I) in which X-Z-R2 is as claimed. In the instant case (1) there is no clear cut indication of the scope of the subject matter covered by the claims; (2) the claim language does not set forth well-defined boundaries of the invention and only states a result obtained; and (3) one of ordinary skill in the art would not know from the claim terms what structure or steps are encompassed by the claims. Moreover, since there are a large number of ways of going from one chemical structure to another, not all of which work, once cannot be sure which steps and conditions are encompassed; the true claim scope is unclear.
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.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 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 105 is rejected under 35 U.S.C. 112(d) or pre-AIA 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 105 recites
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; it does not disclose that this is unsubstituted or particularly substituted. Claim 105 depends of claim 41, and claim 41 requires that
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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 Rejections - 35 USC § 102
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.
Claim(s) 41, 94, 96-98, 101 and 108 are rejected under 35 U.S.C. 102(a)(1) as being clearly anticipated by Park et al. (Synthesis 2009, No. 6, pp 0913-0920).
Park taught a process comprising providing the benzamidine of formula 1, reacting it with carbon disulfide in the presence of cesium carbonate base and benzyl chloride to form the dithiocarbamate compound 2, and converting the dithiocarbamate 2 by reaction with various reagents into a compound of formula (3):
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Park disclosed that various reagents that were tested in the conversion at step ii included DCC, SOCl2 and PCl5 (which are oxidizing agents). Therefore, the conversion was carried out in the presence of an oxidizing agent. See page 914 of Park et al.:
“Various methods were explored to promote the cyclization reaction of benzamidine dithiocarbamate 2. The methods focused on the incorporation of proper nitrogen leaving groups by reaction with various reagents (e.g., EDC·HCl, DCC, TMSCl, TsCl, Ph3P, SOCl2, PCl5, or diphenyl chlorophosphate) based on our previous research results.12 This effort showed that the best reaction conditions for transforming 2 to 5- benzylsulfanyl)-3- phenyl-1,2,4-thiadiazole (3) involve treatment with p-toluenesulfonyl chloride in the presence of triethylamine in 1,2-dichloroethane at 60 °C.”
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 indicating obviousness or nonobviousness.
Claim(s) 41, 94-98, 101-102, 105 and 108 are rejected under 35 U.S.C. 103 as being unpatentable over Park et al. (Synthesis 2009, No. 6, pp 0913-0920) in view of Parsons (GB 1356391) and Parsons (US Patent 3,770,754).
Park taught a process comprising providing the benzamidine of formula 1, reacting it with carbon disulfide in the presence of cesium carbonate base and benzyl chloride to form the dithiocarbamate compound 2, and converting the dithiocarbamate 2 by reaction with various reagents into a compound of formula (I) (3):
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Park disclosed that various reagents that were tested in the conversion at step ii included DCC, SOCl2 and PCl5 (which are oxidizing agents). Therefore, the conversion was carried out in the presence of an oxidizing agent. See page 914 of Park et al.:
“Various methods were explored to promote the cyclization reaction of benzamidine dithiocarbamate 2. The methods focused on the incorporation of proper nitrogen leaving groups by reaction with various reagents (e.g., EDC·HCl, DCC, TMSCl, TsCl, Ph3P, SOCl2, PCl5, or diphenyl chlorophosphate) based on our previous research results.12 This effort showed that the best reaction conditions for transforming 2 to 5- benzylsulfanyl)-3- phenyl-1,2,4-thiadiazole (3) involve treatment with p-toluenesulfonyl chloride in the presence of triethylamine in 1,2-dichloroethane at 60 °C.”
Parsons (GB 1356391) taught the use of compounds of formula
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,
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,
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,
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and others, in the preparation of their sulfonyl and sulfinyl analogues for use as nematicides.
Parsons (US 3,770,754) taught diazoles of formula
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in which X is sulfur, R1 is phenyl and R2 is alkyl, useful as nematicides and plant growth regulants. For example, compounds of the formula
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and
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were prepared. See Example 5.
Ascertainment of the difference between the prior art and the claims (MPEP §2141.02)
Park did not prepare the elected species of formula
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. The prior art uses analogous reactants.
Claim 95 differs in the base used; Park used cesium carbonate.
Finding of prima facie obviousness--rational and motivation (MPEP §2142-2413)
One of ordinary skill in the art is a chemist practitioner with the knowledge and skills of the authors of the references cited in this action. The elected species of formula
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was expected to have nematicidal activity and plant growth regulation activity, according to the genus of compounds taught by Parsons (US 3,770,754). Particularly, the artisan would have envisioned the elected species within the genus of compounds taught by Parsons in view of the compounds of formula
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and
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of Parsons. The elected species would have been obvious.
Products of formula (I) of the claims were known in the prior art, as well as the starting benzamidine, carbon disulfide, and alkyl halide reagents, such as 1-bromopropane, bromoethane, and propargylbromide. The elected species was an obvious compound. 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.
One of ordinary skill in the art wanting to prepare the compounds disclosed in Parsons above, including the elected species, would have been motivated to use the process of Park et al. with the known analogous alkyl bromide reactants (such as with 1-bromopropane) with the expectation of preparing 5-alkylthio-3-phenyl-1,2,4-thiadiazole products which have nematicidal activity. 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.
Regarding the base used in claim 95, potassium carbonate and sodium bicarbonate are alkali carbonate salts commonly used as base and are of the same family as the alkali base cesium carbonate of Park. Parsons (US 3,770,754) taught that the substitution of the 5-mercapto group with an alkyl group is also performed with potassium carbonate as base:
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The use of potassium carbonate or sodium bicarbonate as alkali carbonate base, instead of cesium carbonate, in the reaction of Park would have been obvious to one of ordinary skill.
Conclusion
Claims 41, 94-98, 101-102, 105 and 108 are rejected. No claim is allowable.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to VALERIE RODRIGUEZ-GARCIA whose telephone number is (571)270-5865. The examiner can normally be reached Monday-Friday 9:30am-4:30pm.
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, Clinton Brooks can be reached at 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/VALERIE RODRIGUEZ-GARCIA/Primary Examiner, Art Unit 1621