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 6-28 of J. Edson et al., US 19/365,332 (Oct. 22, 2025) are pending. Claims 6-15 and 22-28, to non-elected inventions of Groups (II) and (VI) are withdrawn from consideration pursuant to 37 CFR 1.142(b). Claims 16-21 are under examination on the merits. Claims 16, 17, and 21 are rejected. Claims 18-20 are objectionable.
Election/Restrictions
Applicant elected Group (III), claims 16-21 drawn to a hydrocarbyl tin compound represented by the formula R'R"(R"'O)CSnL3, with traverse, in the Reply to Restriction Requirement filed on January 27, 2026. Groups (I), claims 1-5 drawn to a compound represented by the formula RSn(C≡CSiR’3)3, are cancelled by Applicant. Claims 6-15 and 22-28, to non-elected inventions of Groups (II) and (VI), are withdrawn from consideration pursuant to 37 CFR 1.142(b). The restriction/election requirement is made FINAL.
Applicant’s Traversal
Applicant argues that the MPEP supports the idea that the claims at issue have the character collectively of a Markush group. Reply at page 6 (citing MPEP § 803.02(II)).
Applicant’s argument is not persuasive because the criteria for a proper requirement for restriction is whether the inventions are independent or distinct as claimed. MPEP § 803. Here, inventions (I)-(IV) are independent or distinct, each from the other because although they are related as film forming precursors, they are still directed to distinct products. The related inventions are distinct if: (1) the inventions as claimed are either not capable of use together or can have a materially different design, mode of operation, function, or effect; (2) the inventions do not overlap in scope, i.e., are mutually exclusive; and (3) the inventions as claimed are not obvious variants. See MPEP § 806.05(j). In the instant case, the inventions as claimed are directed to completely different compounds and therefore have a materially different design, mode of operation, function, or effect. Furthermore, the inventions as claimed do not encompass overlapping subject matter and there is nothing of record to show them to be obvious variants.
Applicant further argues that an election of species, rather than restriction between inventions, should be imposed because ff the examination of the elected species points to patentability of the other species, then there would be no significant additional burden to expand the examination at that point to include the additional species.
This argument is not persuasive for the following reasons. As set forth above, the proper test for restriction is distinctness between inventions. For the reasons in given in the Restriction (Dec. 01, 2025) and restated above, the inventions are distinct and restriction is proper. Further, there is a particularly onerous search burden with respect to the claims at issue because the meaning of certain claims terms is unclear (see § 112(b) rejection below) leading to complicated analysis and searching. For example, since these Groups are directed to different compounds (and particularly where the “hydrolysable ligand” is unclear and structurally undefined), searching requires generating different search queries in electronic searching using CAS STNext software. Further electronic/hand searching is required respecting terms, such as “hydrolysable” other databases, such as textbooks/libraries, Google and Google Scholar.
Claim Objections
Claims 18-20 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
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).
(I) Structurally Unclear Chemical Group “Ox(OH)3-x”
Claims 16, 17, and 21 are rejected pursuant to 35 U.S.C. 112(b), as indefinite because the chemical structural meaning of the claim 16 recitation of “L is . . . Ox(OH)3-x, 0<x<3” is unclear in the context of claim 16 and in view of the specification:
Claim 16 . . . L is LH, where LH is a hydrolysable ligand, or Ox(OH)3-x, 0<x<3.
Under a plain meaning interpretation of claim 16’s “R'R"(R"'O)CSnL3 . . . L is . . . Ox(OH)3-x, 0<x<3”, by setting x to a value of 1, one of skill arrives at the following generic formula:
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Based on the valencies of oxygen and tin, it is unclear to one of skill how compounds within this genus are formed or can even exist. Not only are six highly reactive peroxide bonds required, but also three highly reactive, trivalent oxonium ions. Oxonium ions are generally known in the art as highly reactive intermediates. G. Olah et al., 104 Journal of the American Chemical Society, 2373-2376 (1982); S. Cerero et al., 120 The Journal of Physical Chemistry A, 7045-7050 (2016).
The specification does not provide any example species (prophetic or otherwise). The most relevant portion of the specification regarding the structural meaning of “L is . . . Ox(OH)3-x, 0<x<3” teaches that:
The compositions synthesized herein can be effective precursors for forming the alkyl tin oxo-hydroxo compositions that are advantageous for high resolution patterning, for example in extreme ultraviolet (EUV), ultraviolet (UV), electron-beam lithography. The alkyl tin precursor compositions comprise a group that can be hydrolyzed with water or other suitable reagent under appropriate conditions to form the monohydrocarbyl tin oxo-hydroxo patterning compositions, which, when fully hydrolyzed, can be represented by the formula RSnO(1.5-(x/2))(OH)x where 0 <x [Symbol font/0xA3]3.
. . .
With respect to the precursors with hydrolysable ligands, representative hydrolysis and condensation reactions that can transform the compositions with hydrolysable Sn-X groups are indicated in the following reactions:
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If the hydrolysis product HL is sufficiently volatile, in situ hydrolysis can be performed with water vapor during the substrate coating process, but the hydrolysis reaction can also be performed in solution to form the alkyl tin oxo-hydroxo compositions.
Specification at page 6, line 13 - page 7, line 4.
While the above specification excerpt teaches the hydrolysis product of RL3 [Symbol font/0xAE] RSnOx/2OH3-x, this product does not appear to correspond to simply setting variable L in the claim 16 formula R'R"(R"'O)CSnL3 as “Ox(OH)3-x, 0<x<3”. In sum, the structural meaning of “R'R"(R"'O)CSnL3 . . . L is . . . Ox(OH)3-x, 0<x<3” is unclear to one of skill in the art. Significantly, the specification guidance does not appear to correspond to the claim language at issue; that is, it is not clear to one of skill that above cited specification portion even corresponds to the claim 16 limitation of “R'R"(R"'O)CSnL3 . . . L is . . . Ox(OH)3-x, 0<x<3”.
Dependent claims 17 and 21 do not cure the issue.
(II) Unclear Structure-Function Limitation “hydrolysable ligand”
Claims 16, 17, and 21 are rejected under 35 U.S.C. 112(b) as indefinite because the claim 1 recitation of “hydrolysable ligand” is unclear:
16. A hydrocarbyl tin compound represented by the formula R'R"(R"'O)CSnL3
where R', R" and R"' are independently H or hydrocarbyl groups having from 1 to 15 carbon atoms and optional unsaturated carbon-carbon bonds, optional aromatic groups and optional hetero atoms, and
L is LH, where LH is a hydrolysable ligand, or Ox(OH)3-x, 0<x<3.
in the context of claim 16 is unclear in view of the teachings of the specification. The term “hydrolysable” is a functional limitation. MPEP § 2173.05(g). The specification does not provide a succinct structural definition of “hydrolysable ligand”. The first step is interpretation of this term. MPEP § 2173.01.
(i) Plain Meaning of “hydrolysable ligand”
The plain meaning of “hydrolysable ligand” in the claim 16 context of Sn-L3, is a L group that functions to be cleaved from the tin atom in an aqueous environment under the particular aqueous conditions. See e.g., Hawley's Condensed Chemical Dictionary, page 736 (16th ed., 2016, R.J. Larrañaga ed.); IUPAC, Compendium of Chemical Terminology, Gold Book, "hydrolysis", pages 698 (2014).
(ii) Specification Discussion and Purpose of “hydrolysable ligand”
The only disclosed examples of hydrolysable ligands are “L corresponding to hydrolysable ligands, such as alkoxide (hydrocarbyl oxide), acetylide or amide moieties”. See e.g., specification at page 7, lines 16-17; Id. at page 4, lines 16-17; Id. at page 4, lines 27-30; Id. at page 5, lines 21-24. That is, the tin bond in a Sn-NR’2, Sn-≡CR’ or Sn-O-R. However, this still leaves open the question as to what other groups are hydrolysable.
The specification teaches that a first purpose of the hydrolysable ligand is “the synthesis of organotin trialkoxides (triorganooxides) from either the triamides or the triacetylides through substitution of the hydrolysable ligands or to oxo/hydroxo compounds through hydrolysis of the ligands”. Specification at page 4, lines 27-30; Id. at page 8, lines 11-13. This can be summarized as the following reaction:
C-SnL3 + alcohol (R0-OH) or water [Symbol font/0xAE] C-Sn(OR0)3 or C-Sn(OH)3
The specification teaches that a second purpose of the hydrolysable and non-hydrolysable (in C-SnL3 compounds) is that the non-hydrolysable C-Sn bond is radiation sensitive and is also stable during the water-vapor-hydrolysis mediated substrate coating as described further in 10,228,618 to Meyers. Here, the hydrolysable group is cleaved during hydrolysis-mediated substrate coating leaving a radiation-sensitive coating of R-SnO(1.5-(x/2))(OH)x on the substrate that can subsequently be patterned by treating certain areas with UV or EUV radiation (by cleaving the R-Sn bond) and removing either the treated or untreated areas with solvent development to form a photoresist as taught in 10,228,618 (col. 4).
With respect to the precursors with hydrolysable ligands, representative hydrolysis and condensation reactions that can transform the compositions with hydrolysable Sn-X groups are indicated in the following reactions:
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If the hydrolysis product HL is sufficiently volatile, in situ hydrolysis can be performed with water vapor during the substrate coating process, but the hydrolysis reaction can also be performed in solution to form the alkyl tin oxo-hydroxo compositions. These processing options are described further in [10,228,618 to Meyers].
The overall synthesis process for forming the radiation patternable coatings involves formation of the desired R-Sn (C-Sn) bonds with three hydrolysable ligands, with the potential for exchanging the hydrolysable ligands under suitable circumstances while maintaining the R ligand. R forms an carbon-tin bond wherein the carbon bound to the tin is sp3 or sp2 hybridized, and R can comprise heteroatoms, which are not carbon or hydrogen. As noted above, for convenience as well as consistency in the art, R can be interchangeably referred to as an alkyl ligand, organo ligand or hydrocarbyl ligand.
Specification at page 6, line 27- page 7, line 13; In another relevant section, the specification teaches the following:
The compositions synthesized herein can be effective precursors for forming the alkyl tin oxo-hydroxo compositions that are advantageous for high resolution patterning, for example in extreme ultraviolet (EUV), ultraviolet (UV), electron-beam lithography. The alkyl tin precursor compositions comprise a group that can be hydrolyzed with water or other suitable reagent under appropriate conditions to form the monohydrocarbyl tin oxo-hydroxo patterning compositions, which, when fully hydrolyzed, can be represented by the formula RSnO(1.5-(x/2))(OH)x where 0 <x[Symbol font/0xA3]3. It can be convenient to perform the hydrolysis to form the oxo-hydroxo compositions in situ, such as during deposition and/or following initial coating formation. While the triamides and triacetylides described herein can be used under hydrolyzing conditions for forming radiation sensitive coatings for patterning, it can be desirable to form further intermediate hydrocarbyl tin trialkoxides (trihydrocarbyl oxides) for forming the coatings. Processing to form the hydrocarbyl tin trialkoxides are described herein. The various precursor compounds with hydrolysable ligands generally carry forward the R-ligand to tin through the process and are synthesized with this perspective.
Specification at page 6, lines 13-19. These specification portions indicate that the meaning of “hydrolysable ligand” depends upon the hydrolysis reagent (e.g., water or an alcohol) and upon the particular hydrolysis conditions.
(iii) Broadest Reasonable Interpretation of “hydrolysable ligand”
While the specification discusses the purpose of the “hydrolysable ligand”, notably under undefined hydrolysis conditions, still particular embodiments appearing in the written description may not be read into a claim when the claim language is broader than the embodiment. MPEP § 2111.01(II).
The broadest reasonable interpretation of the claim 16 term “hydrolysable ligand”, consistent with the specification, is a tin ligand “L”, in the claimed formula R'R"(R"'O)CSnL3, where the Sn-L bond is cleaved upon treatment of the claimed R'R"(R"'O)CSnL3 with water and/or an alcohol under conditions of time, temperature, and, optionally, the presence of reagents/reactants in addition to the water or alcohol.
(iv) The Term “hydrolysable ligand” Is unclear in the Context of Claim 16 and in view of the Specification
Per the MPEP, examiners should consider the following factors when examining claims that contain functional language to determine whether the language is ambiguous: (1) whether there is a clear cut indication of the scope of the subject matter covered by the claim; (2) whether the language sets forth well-defined boundaries of the invention or only states a problem solved or a result obtained; and (3) whether one of ordinary skill in the art would know from the claim terms what structure or steps are encompassed by the claim. MPEP § 2173.05(g).
The rejection under 35 U.S.C. 112(b) is appropriate because the claimed functional language “hydrolysable ligand”, given its broadest reasonable interpretation, is such that the language leaves room for ambiguity and the boundaries are not clear and precise. MPEP § 2173.05(g). This is at least because neither claim 16 nor the specification defines the particular conditions of temperature, or other reaction components that may or may not be present in the hydrolysis reaction mixture in addition to the hydrolysis reagent.
Here one of skill does not know which groups are incapable of performing the cited claim 16 function, and are thus intended by Applicant to be excluded from claim 16. For example, the specification appears to teach that the groups hydrocarbylC(R*)2-Sn and hydrocarbylC(R*)=Sn are not hydrolysable.1 Specification at page 5, lines 12-17. Yet the art teaches that such hydrocarbyl groups are hydrolysable under strong acid conditions. For example, R. Ingham, Organotin Compounds, 60 Chemical reviews, 459-539 (1960) teaches that in tin compounds of the formula R4Sn (table 2) in which the R groups are all the same (alkyl or aryl), cleavage of the carbon-tin bond occurs readily with strong aqueous acids. Ingham at page 462, col. 1. In another Example, R. Alexander et al., 30 Tetrahedron, 899-904 (1974) (“Alexander”) teaches that PhCH2SnMe3 and Me4Sn are cleaved by aqueous methanolic perchloric acid resulting in methane evolution. Alexander at Abstract.
Further, a particular group may be cleaved from tin under one set of hydrolysis conditions but not under another set of conditions. Here, rather than setting forth well-defined boundaries of the invention, the claim 16 language at issue merely states a problem solved or a result obtained. MPEP § 2173.05(g). A particular claim 16 “hydrolysable ligand” could be alternatively interpreted as either not meeting or meeting the claimed functional limitation depending upon the chosen hydrolysis conditions. As such, contrary to 35 U.S.C. 112(b), claim 16 does not provide clear warning to others as to which “hydrolysable ligand” constitute infringement of the cited functional language. MPEP 2173.02(II).
Dependent claims 17 and 21 do not cure the issue.
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) Rejection over B. Martín-Matute et al., 7 Chemistry a European Journal, 2341-2348 (2001) (“Martín-Matute”)
Claims 16 and 21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by B. Martín-Matute et al., 7 Chemistry a European Journal, 2341-2348 (2001) (“Martín-Matute”). Martín-Matute discloses compounds that fall within the claim 16 genus.
The Examiner depicts the instant claim 16 formula as follows for comparison to the prior art structure:
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Martín-Matute discloses the following three tin compounds 3a, 3b, and 3c, which are mapped to the claim 16 formula as follows.
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Martín-Matute at page 2345, col. 2. In each of prior art compounds one of the -CH2-O(C6H4)-R groups meets the claim 16 structural portion R’R”(R’”O)C-Sn (as labelled above) and the other three groups meet the claim 16 limitation of L3 where “L is LH, where LH is a hydrolysable ligand”.
Here, the group:
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reads on “hydrolysable group” LH, per its interpretation above, to function within the claim 16 formula R'R"(R"'O)CSnL3, such that the Sn-L bond is cleaved upon treatment of the claimed R'R"(R"'O)CSnL3 with water and/or an alcohol under conditions of time, temperature, and, optionally, the presence of reagents/reactants in addition to the water or alcohol. For example, for example, R. Ingham, Organotin Compounds, 60 Chemical reviews, 459-539 (1960) teaches that in tin compounds of the formula R4Sn (table 2) in which the R groups are all the same (alkyl or aryl), cleavage of the carbon-tin bond occurs readily with strong aqueous acids. Ingham at page 462, col. 1. Here, particularly in the case of the electron withdrawing group -NO2 for compound 3c, the above group as a whole, bonded to tin, is expected by one of skill to be readily susceptible to hydrolysis.
Respecting claim 21, Martín-Matute teaches that compound 3c was prepared from 0.78 mmol starting iodostannane in 4 ml of DMF which is “an aprotic organic solvent” to give a 64% yield. Martín-Matute at page 2345, col. 2, last paragraph. As such Martín-Matute discloses a solution comprising 4 ml of DMF and about 0.5 mmols of 3c. This calculates to 0.0005(mols)/.004(L) = 0.125 M, which falls within and anticipates the claimed range of “about 0.005 to about 1.4 M”.
§ 102(a)(1) Rejection over J. Bartolin et al., 25 Organometallics, 4738-4740 (2006) (“Bartolin”)
Claim 16 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by J. Bartolin et al., 25 Organometallics, 4738-4740 (2006) (“Bartolin”). Bartolin discloses the following compound 2a [(Me3Si)2N]2SnI[CH2OC(CH3)3]. Bartolin at page S1, second paragraph.
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Here, the iodo and two -N(SiMe3)2 groups correspond to the claim 16 LH “hydrolysable groups” and the - CH2OC(CH3)3 group corresponds to the claim 16 R'R"(R"'O)C portion, where R’ and R” are H.
§ 102(a)(1) Rejection over CAS Abstract, U. Schoellkopf et al., 5 Journal of Organometallic Chemistry, 300 (1966) (“Schoellkopf-ABS”)
Claims 16 and 17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CAS Abstract Indexed Compounds, U. Schoellkopf et al., 5 Journal of Organometallic Chemistry, 300 (1966) (“Schoellkopf-ABS”).2
Schoellkopf-ABS discloses the following compound:
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In the above compound, one of the -CH2-O-CH3 meets the claim 16 structural portion R’R”(R’”O)C-Sn (as labelled above) and the other three -CH2-O-CH3 groups meet the claim 16 limitation of L3 where “L is LH, where LH is a hydrolysable ligand”. Here, the group -CH2-O-CH3, reads on “hydrolysable group” LH, per its interpretation above, to function within the claim 16 formula R'R"(R"'O)CSnL3, such that the Sn-L bond is cleaved upon treatment of the claimed R'R"(R"'O)CSnL3 with water and/or an alcohol under conditions of time, temperature, and, optionally, the presence of reagents/reactants in addition to the water or alcohol. For example, for example, R. Ingham, Organotin Compounds, 60 Chemical reviews, 459-539 (1960) teaches that in tin compounds of the formula R4Sn (table 2) in which the R groups are all the same (alkyl or aryl), cleavage of the carbon-tin bond occurs readily with strong aqueous acids. Ingham at page 462, col. 1. Here, particularly in the case of the electron withdrawing group -O-CH3, the above group as a whole, bonded to tin, is expected by one of skill to be readily susceptible to hydrolysis.
The claim 17 limitations of “wherein R' and R" are H, and R"' is CH3” are clearly met.
Claim Rejections 35 U.S.C. 112(a) – Written Description
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.
For an originally filed claim, 35 U.S.C. 112(a) requires that the specification shall contain a written description of the invention demonstrate that the inventor was in possession of the invention that is claimed.3 MPEP § 2163(I); MPEP § 2163(II)(A)(3)(a). Possession may be shown by disclosure of drawings or structural chemical formulas that show that the invention was complete. MPEP § 2163(I).
The written description requirement for a claimed chemical genus may be satisfied through sufficient description of a representative number of species by actual reduction to practice, reduction to drawings, or by disclosure of relevant, identifying characteristics, i.e., structure or other physical and/or chemical properties, by functional characteristics coupled with a known or disclosed correlation between function and structure, or by a combination of such identifying characteristics, sufficient to show the inventor was in possession of the claimed genus. MPEP § 2163(II)(A)(3)(a)(ii).
A "representative number of species" means that the species which are adequately described are representative of the entire genus. MPEP § 2163(II)(A)(3)(a)(ii). Thus, when there is substantial variation within the genus, one must describe a sufficient variety of species to reflect the variation within the genus. MPEP § 2163(II)(A)(3)(a)(ii) (citing AbbVie Deutschland GmbH & Co., KG v. Janssen Biotech, Inc., 759 F.3d 1285, 1300, 111 USPQ2d 1780, 1790 (Fed. Cir. 2014).
Disclosure of function and minimal structure may be sufficient when there is a well-established correlation between structure and function. MPEP § 2163(II)(A)(3)(a)(i). In contrast, without such a correlation, the capability to recognize or understand the structure from the mere recitation of function and minimal structure is highly unlikely. MPEP § 2163(II)(A)(3)(a)(i) (citing Eli Lilly, 119 F.3d at 1568, 43 USPQ2d at 1406). Accordingly, a “sufficient description . . . requires the disclosure of either a representative number of species falling within the scope of the genus or structural features common to the members of the genus so that one of skill in the art can ‘visualize or recognize’ the members of the genus.” Ariad Pharm., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1349 (Fed. Cir. 2010).
The § 112(a) rejection
Claims 16, 17 and 21 are rejected under 35 U.S.C. 112(a) as failing to comply with the written description requirement with respect to the recitation of “hydrolysable ligand” in base claim 16:
16. A hydrocarbyl tin compound represented by the formula R'R"(R"'O)CSnL3
where R', R" and R"' are independently H or hydrocarbyl groups having from 1 to 15 carbon atoms and optional unsaturated carbon-carbon bonds, optional aromatic groups and optional hetero atoms, and
L is LH, where LH is a hydrolysable ligand, or Ox(OH)3-x, 0<x<3.
because the application as filed does not disclose either sufficient species of “hydrolysable ligands” nor is there a well-established structure-function correlation between formula claimed formula R'R"(R"'O)CSnL3, (where L is LH, where LH is a hydrolysable ligand) and the function of acting as a “hydrolysable ligand” such that one of skill in the art can recognize that Applicant was in possession of the full scope of claimed compounds of the formula R'R"(R"'O)CSnLH3.
Claim Breadth
Claim breath is relevant to the instant § 112(a) written description rejection. The written description must lead a person of ordinary skill in the art to understand that the inventor possessed the entire scope of the claimed invention. MPEP § 2163(II)(A)(3)(a)(ii) (citing Juno Therapeutics, Inc. v. Kite Pharma, Inc., 10 F.4th 1330, 1337, 2021 USPQ2d 893 (Fed. Cir. 2021)).
Per Claim Interpretation above, the broadest reasonable interpretation of the claim 16 term “hydrolysable ligand”, consistent with the specification, is a tin ligand “L”, in the claimed formula R'R"(R"'O)CSnL3, where the Sn-L bond is cleaved upon treatment of the claimed R'R"(R"'O)CSnL3 with water and/or an alcohol under conditions of time, temperature, and, optionally, the presence of reagents/reactants in addition to the water or alcohol.
Here, the term “hydrolysable ligand” is conceptually broad because it is structurally undefined by claim 16 (i.e., defined entirely by its function”), where the hydrolysis conditions are also undefined by either claim 16 or the specification.
Guidance in the Specification and Art
It is first noted that what is conventional or well known to one of ordinary skill in the art need not be disclosed in detail. MPEP § (II)(A)(3)(a). Thus, the state of and predictability in the art is a relevant consideration in determining compliance with § 112(a), written description. MPEP § (II)(A)(3)(a) (citing Capon v. Eshhar, 418 F.3d 1349, 1357, 76 USPQ2d 1078, 1085 (Fed. Cir. 2005) ("The ‘written description’ requirement must be applied in the context of the particular invention and the state of the knowledge…. As each field evolves, the balance also evolves between what is known and what is added by each inventive contribution”).
The only disclosed examples of hydrolysable ligands are “L corresponding to hydrolysable ligands, such as alkoxide (hydrocarbyl oxide), acetylide or amide moieties”. See e.g., specification at page 7, lines 16-17; Id. at page 4, lines 16-17; Id. at page 4, lines 27-30; Id. at page 5, lines 21-24. That is, the tin bond in a Sn-NR’2, Sn-≡CR’, Sn-O-R. However, this still leaves open the question as to what other groups are hydrolysable. The specification and the art also teach that unsubstituted alkyl and aryl groups bonded to tin are relatively stable to reaction with water alone.
As used herein, and as generally consistent with usage in this field, "monoalkyl" can be used interchangeably with "monoorgano" or "monohydrocarbyl"4 with "alkyl" ligands suggesting bonding to the tin with carbon to form a bond that is generally not hydrolysable through contact with water, which would involve sp3 or sp2 hybridized carbon, while the "alkyl" group can have internal unsaturated bonds and hetero-atoms, i.e., distinct from carbon and hydrogen, that are not involved in bonding with the tin.
Specification at page 5, lines 12-17 (emphasis added). Similarly, R. Ingham, Organotin Compounds, 60 Chemical reviews, 459-539 (1960) teaches that R4Sn (table 2) in which the R groups are all the same (alkyl or aryl) are generally stable to water alone. Ingham at page 462, col. 1.5
However, beyond such simple alkyl and aryl-tin bonds, searches conducted did not reveal an art-known, structure-function correlation between tin-ligand bonds and hydrolysis. Nor is any such relationship disclosed in the specification.
In sum, neither the specification, art cited by Applicant, nor art identified in searches teaches a strong or well-established correlation between tin-ligand bonds predictable of species throughout the vast breadth of claimed R'R"(R"'O)CSnLH3 that, such that one of skill in the art can ‘visualize or recognize’ the members of the claimed genus that perform the claimed function. Ariad Pharm., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1349 (Fed. Cir. 2010).
Claims 16, 17 and 21 Lack an Adequate Written Description
Claims 16, 17 and 21 lack adequate written description support because the application as filed does not disclose either sufficient species of “hydrolysable groups” nor is there a well-established, structure-function correlation between formula claimed formula R'R"(R"'O)CSnL3, (where L is LH, where LH is a hydrolysable ligand) and the function of acting as a “hydrolysable ligand” such that one of skill in the art can recognize that Applicant was in possession of the full scope of claimed compounds of the formula R'R"(R"'O)CSnLH3.
Here, Applicant is not in possession of the full claim scope because neither the specification nor the art of record provides sufficient guidance allowing one of skill to correctly choose LH, particularly where LH has no associated structure in claims. The only disclosed examples of hydrolysable ligands are “L corresponding to hydrolysable ligands, such as alkoxide (hydrocarbyl oxide), acetylide or amide moieties”. See e.g., specification at page 7, lines 16-17; Id. at page 4, lines 16-17; Id. at page 4, lines 27-30; Id. at page 5, lines 21-24. These three species are clearly not representative of the full genus of LH where LH has no associated structure in claims. A "representative number of species" means that the species which are adequately described are representative of the entire genus. MPEP § 2163(II)(A)(3)(a)(ii); see also, Idenix Pharms. LLC v. Gilead Scis. Inc., 941 F.3d 1149, 1164 (Fed. Cir. 2019) (“[a]s a result, a POSA is deprived of any meaningful guidance into what compounds beyond the examples and formulas, if any, would provide the same result”). Here the disclosed species are clearly not representative of the claimed genus and LH is recited in the subject claims with no associated structure. As stated above, the written description requirement may also be satisfied through disclosure of function and minimal structure when there is a well-established correlation between structure and function. MPEP § 2163(II)(A)(3)(a)(i). In contrast, without such a correlation, the capability to recognize or understand the structure from the mere recitation of function and minimal structure is highly unlikely. MPEP § 2163(II)(A)(3)(a)(i) (citing Eli Lilly, 119 F.3d at 1568, 43 USPQ2d at 1406).
Subject Matter Free of the Art of Record
Claims 18-20 are free of the art of record. These claims are directed the following Markush groups and species.
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The closest prior art of record is S. Meyers et al., US 10,228,618 (2019) (“Meyers”). Meyers teaches that compounds of the formula RnSnX4-n, where n=1 or 2, or a mixture thereof, in which R is a hydrocarbyl group with 1-31 carbon atoms, and X is a ligand with a hydrolysable M-X bond. Meyers at col. 2, lines 6-23.
Meyers teaches that in the disclosed compounds RnSnX4-n, the hydrolysable “X” group is cleaved during hydrolysis-mediated substrate coating leaving a radiation-sensitive coating of R-SnO(1.5-(x/2))(OH)x (R-Sn is a radiation sensitive bond) on the substrate that can subsequently be patterned by treating certain areas with UV or EUV radiation (by cleaving the R-Sn bond) and removing either the treated or untreated areas with solvent development to form a photoresist as taught in Meyers at col. 4, lines 15-47.
The closest species taught by Meyers are tBuSn(NMe2)3 and Sn(O-tBu)4.
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Meyers at col. 18, Table 1. Meyers compounds differ in that they lack the instantly claimed R’R”(R”’O)C- group.
In the chemical arts obviousness rational based on structural modification is stated as motivation to select a known compound and also motivation to structurally modify the selected compound in a particular way to achieve a claimed compound. MPEP § 2143(I)(B) (see for example, MPEP § 2143(I)(B) Example 9, citing Eisai Co. Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 87 USPQ2d 1452 (Fed. Cir. 2008). 6
Here, one of ordinary skill is not motivated by Meyers or Meyers in view of secondary art to structurally modify either of Meyers’ compounds tBuSn(NMe2)3 or Sn(O-tBu)4 by replacing the t-Bu or t-Bu-O group with a R’R”(R”’O)C- group so as to arrive at a claimed compound.
Conclusion
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 The Examiner designates R* as alkyl, alkenyl, aryl or some other group that prevents the cleavage of Sn-carbon bond under the particular hydrolysis conditions.
2 A copy of the underlying reference, U. Schoellkopf et al., 5 Journal of Organometallic Chemistry, 300 (1966), has been ordered.
3 While there is a presumption that an adequate written description of the claimed invention is present in the specification as filed, a question as to whether a specification provides an adequate written description may arise in the context of an original claim. MPEP § 2163.03 (V) (citing In re Wertheim, 541 F.2d 257, 262, 191 USPQ 90, 96 (CCPA 1976)). An original claim may lack written description support when (1) the claim defines the invention in functional language specifying a desired result but the disclosure fails to sufficiently identify how the function is performed or the result is achieved or (2) a broad genus claim is presented but the disclosure only describes a narrow species with no evidence that the genus is contemplated. MPEP § 2163.03 (V) (citing Ariad Pharms., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1349-50 (Fed. Cir. 2010) ("[e]ven if a claim is supported by the specification, the language of the specification, to the extent possible, must describe the claimed invention so that one skilled in the art can recognize what is claimed”).
4 See, IUPAC, Compendium of Chemical Terminology, Gold Book, "hydrocarbyl", pages 694-695 (2014).
5 However, Ingham also teaches that in tin compounds of the formula R4Sn (table 2) in which the R groups are all the same (alkyl or aryl), cleavage of the carbon-tin bond occurs readily with strong aqueous acids. Ingham at page 462, col. 1. In another Example, R. Alexander et al., 30 Tetrahedron, 899-904 (1974) (“Alexander”) teaches that PhCH2SnMe3 and Me4Sn are cleaved by aqueous methanolic perchloric acid resulting in methane evolution. Alexander at Abstract.
6 In the chemical arts, a "lead compound" obviousness analysis is often applied; the “lead compound” analysis requiring 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). However, 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’).