DETAILED ACTION
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 .
Status of Claims
Claims 1 – 13, 16, 18 – 21 and 24 – 27 are pending.
Clams 14, 15, 17, 22 and 23 have been canceled.
Claims 1, 3 –10, 12, 13, 16, 18 – 21 and 24 – 27 are rejected.
Claims 2 and 11 are objected.
Specification
The use of the term “Raney Ni”, which is a trade name or a mark used in commerce, has been noted in this application on pages 8 and 10. The term should be accompanied by the generic terminology; furthermore the term should be capitalized wherever it appears or, where appropriate, include a proper symbol indicating use in commerce such as ™, SM , or ® following the term.
Although the use of trade names and marks used in commerce (i.e., trademarks, service marks, certification marks, and collective marks) are permissible in patent applications, the proprietary nature of the marks should be respected and every effort made to prevent their use in any manner which might adversely affect their validity as commercial marks.
Claim Rejections - 35 USC § 112
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.
Claim 24 rejected under 35 U.S.C. 112(b), as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, regards as the invention.
Claim 24 contains the trademark/trade name “Raney Ni”. Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe a type of catalyst and, accordingly, the identification/description is indefinite.
Claim Rejections - 35 USC § 112
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.
Claims 6 and 7 are 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. Claim 6 fails to reference a preceding claim and fails to further limit the previously set forth claim. 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 7 is rejected for being dependent on a rejected base claim.
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.
Claims 1, 3 –10, 12, 13, 16, 18, 19, 21 and 24 – 27 are rejected under 35 U.S.C. 112(a), because the specification, while being enabling for the process for manufacturing an aniline 2, wherein PG denotes an amino protective group Boc (t-butoxycarbonyl) and the process is comprised of reacting nitroarene 1 with hydrogen, wherein the PG in nitroarene is Boc in the presence of a transition catalyst and in an aprotic solvent of tert-butyl methyl ether (TBME); does not reasonably provide enablement for the process for manufacturing an aniline 2, wherein PG in aniline 2 and nitroarene is an amino protective group selected from benzyl, 4-methoxybenzyl, benzhydrvl. Fmoc (fluorenylmethoxycarbonyl). Cbz (benzyloxycarbonyl), Moz (p-methoxybenzyl carbonyl), Troc (2,2,2-trichloroethoxycarbonyl). Teoc (2-(Trimethylsilyl)ethoxycarbonyl), Adoc (adamantoxycarbonyl), formyl, acetyl, and cyclobutoxycarbonyl, and the process is comprised of reacting nitroarene 1 with hydrogen, in the presence of a transition catalyst and in any aprotic solvent. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention commensurate in scope with these claims.
The test for enablement is whether one skilled in the art could make and use the claimed invention from the disclosures in the specification coupled with information known in the art without undue experimentation (United States v. Telectronice, 8, USPQ2D 1217 (Fed. Cir, 1988). Whether undue experimentation is needed is not based upon a single factor but rather in a conclusion reached by weighing many factors. The factors to be considered in determining whether a disclosure meets the enablement requirements of 35 U.S.C. 112, first paragraph, have been described in In re Wands, 858 F.2d 731, 8 USPQ2d 1400 (Fed. Cir., 1988). The court in Wands states, “Enablement is not precluded by the necessity for some experimentation, such as routine screening. However, experimentation needed to practice the invention must not be undue experimentation. The key word is ‘undue’, not ‘experimentation’” (Wands, 8 USPQ2sd 1404). Clearly, enablement of a claimed invention cannot be predicated on the basis of quantity of experimentation required to make or use the invention. “Whether undue experimentation is needed is not a single, simple factual determination, but rather is a conclusion reached by weighing many factual considerations” (Wands, 8 USPQ2d 1404). Among these factors are: (1) the nature of the invention; (2) the breadth of the claims; (3) the state of the prior art; (4) the predictability or unpredictability of the art; (5) the relative skill of those in the art; (6) the amount of direction or guidance presented; (7) the presence or absence of working examples; and (8) the quantity of experimentation necessary.
While all of these factors are considered, a sufficient amount for a prima facie case is discussed below.
(1) The nature of the invention: The nature of the claims 1, 3 –10, 12, 13, 16, 18, 19, 21 and 24 - 26 are drawn to the process for manufacturing an aniline 2, wherein PG in aniline 2 and nitroarene 1 is an amino protective group selected from benzyl, 4-methoxybenzyl, benzhydrvl. Fmoc (fluorenylmethoxycarbonyl). Cbz (benzyloxycarbonyl), Moz (p-methoxybenzyl carbonyl), Troc (2,2,2-trichloroethoxycarbonyl). Teoc (2-(Trimethylsilyl)ethoxycarbonyl), Adoc (adamantoxycarbonyl), formyl, acetyl, and cyclobutoxycarbonyl, and the process is comprised of reacting nitroarene 1 with hydrogen, in the presence of a transition catalyst and in any aprotic solvent.
The nature of claim 27 is drawn to for manufacturing an aniline 2, wherein PG in aniline 2 in hydrogen or BOC and in nitroarene 1, the PG denotes any amino protective group, wherein the process comprises reacting hydrogen with nitroarene 1 in the presence of a transition catalyst and in tert-butyl methyl ether (TBME).
(2) the breadth of the claims:
The invention in the claim 1 and dependent claims is that the amino protective group is benzyl, 4-methoxybenzyl, benzhydrvl. Fmoc (fluorenylmethoxycarbonyl). Cbz (benzyloxycarbonyl), Moz (p-methoxybenzyl carbonyl), Troc (2,2,2-trichloroethoxycarbonyl). Teoc (2-(Trimethylsilyl)ethoxycarbonyl), Adoc (adamantoxycarbonyl), formyl, acetyl, and cyclobutoxycarbonyl; and the aprotic solvent can be any known aprotic solvent.
The invention of claim 27 is that the amino protective group, PG, for the nitroarene 1 can be any known amino protective group.
(3) The state of the prior art: the state of the prior art is found in the teachings of teaching of Arrowsmith et al. (EP 0307121), Trussardi et al. (WO2015/086495) and Galley et al. (WO2017/157873).
Arrowsmith discloses preparation 14 on page 20:
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Trussardi discloses the preparation of aniline 2 where PG denotes H or an amino protective group (Boc).
Example 8.1 on page 25 – 26.
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8.2 on page 16
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Example 9.1 on pages 26 – 27
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Galley et al. discloses the process for preparing compound (IV) from the corresponding Boc protecting group of claim 21 and wherein the solvent is aprotic. (Example 1, step b).
(4)The predictability or unpredictability of the art: Chemistry is unpredictable. In reMarzocchi, 439 F2d 220, 169 USPQ 367 para. 3. However, the "predictability or lack thereof” in the art refers to the ability of one skilled in the art to extrapolate the disclosed or know results to the claimed invention. If one skilled in the art can readily anticipate the effect of a change within the subject matter to which the claimed invention pertains, then there is predictability in the art. MPEP 2164.03.
Arrowsmith discloses the use of aprotic solvent ethyl acetate in Preparation 14 in combination with 5%Pd/C catalyst during hydrogenation under similar reaction conditions and with similar molecules. In order to obtain the final powder form, a solvent swap was made to the use of ether, another aprotic solvent. As such, it is highly likely that the claimed process performed with the aprotic solvents other than TBME and the nitroarene 1 having amino protective groups being selected from benzyl, 4-methoxybenzyl, benzhydrvl. Fmoc (fluorenylmethoxycarbonyl). Cbz (benzyloxycarbonyl), Moz (p-methoxybenzyl carbonyl), Troc (2,2,2-trichloroethoxycarbonyl). Teoc (2-(Trimethylsilyl)ethoxycarbonyl), Adoc (adamantoxycarbonyl), formyl, acetyl, and cyclobutoxycarbonyl; will probably require different solvents for crystallization in high yield and purity.
Similarly, it is highly likely that in a process as discloses in claim 27 wherein PG or nitroarene 1 denotes any amino protective group, there will be a requirement to use a different solvent for crystallization of the end product in high yield and purity.
(5) The relative skill of those in the art: One of ordinary skill is a practicing organic chemist.
(6) The amount of direction or guidance presented and (7) the presence or absence of working examples:
The specification has provided guidance for preparing aniline 2 in a TBME solvent with a trace amount of water in Example 1. Also, provided guidance for preparing aniline 2 in a dry solvent of TBME. In both reactions the only protective agent was Boc.
However, the specification does not provide guidance for the hydrogenation reaction wherein the product aniline 2 has a PG the is hydrogen or amino protective groups; such as, is benzyl, 4-methoxybenzyl, benzhydrvl. Fmoc (fluorenylmethoxycarbonyl). Cbz (benzyloxycarbonyl), Moz (p-methoxybenzyl carbonyl), Troc (2,2,2-trichloroethoxycarbonyl). Teoc (2-(Trimethylsilyl)ethoxycarbonyl), Adoc (adamantoxycarbonyl), formyl, acetyl, and cyclobutoxycarbonyl, from a reaction of nitroarene 1 with hydrogen in any aprotic solvent and the PG of nitroarene 1 is benzyl, 4-methoxybenzyl, benzhydrvl. Fmoc (fluorenylmethoxycarbonyl). Cbz (benzyloxycarbonyl), Moz (p-methoxybenzyl carbonyl), Troc (2,2,2-trichloroethoxycarbonyl). Teoc (2-(Trimethylsilyl)ethoxycarbonyl), Adoc (adamantoxycarbonyl), formyl, acetyl, and cyclobutoxycarbonyl.
Additionally, the is no guidance for he process of claim 27 wherein aniline 2 is obtained with PG denoted as hydrogen or Boc, and the hydrogenation reaction with nitroarene 1 having a PG of any amino protective group, and in TBME.
(8) The quantity of experimentation necessary:
Considering the state of the art as discussed by the references above, particularly with regards to prior art teaching for preparing aniline 2 and the high unpredictability in the art as evidenced therein, and the lack of guidance provided in the specification, one of ordinary skill in the art would be burdened with undue experimentation to practice the invention commensurate in the scope of the claims.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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) 20 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Trussardi et al. (WO2015/086495).
Rejected claim is to aniline 2, wherein PG denotes Boc (t-butoxycarbonyl), benzyl, 4-methoxybenzyl, benzhydrvl. Fmoc (fluorenylmethoxycarbonyl). Cbz (benzyloxycarbonyl), Moz (p-methoxybenzyl carbonyl), Troc (2,2,2-trichloroethoxycarbonyl). Teoc (2-(Trimethylsilyl)ethoxycarbonyl), Adoc (adamantoxycarbonyl), formyl, acetyl, and cyclobutoxycarbonyl.
Trussardi discloses
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, wherein R1 denotes hydrogen or an amino protecting group. In Trussardi the term "amino protecting group" refers to an acid or Lewis acid sensitive substituent conventionally used to hinder the reactivity of the amino group. Suitable acid or Lewis acid sensitive amino protecting groups are described in Green T., "Protective Groups in Organic Synthesis", 4th Ed. by Wiley Interscience, 2007, Chapter 7, 696 ff.. Suitable amino protecting groups for PG can therefore be selected from Boc (t-butoxycarbonyl), benzyl, 4-methoxybenzyl, benzhydryl, Fmoc (fluorenylmethoxycarbonyl), Cbz (benzyloxycarbonyl), Moz (p-
methoxybenzyl carbonyl), Troc (2,2,2-trichloroethoxycarbonyl), Teoc (2-
(Trimethylsilyl)ethoxycarbonyl), Adoc (adamantoxycarbonyl), formyl, acetyl or
cyclobutoxycarbonyl. More particularly Boc or benzyl is used. (pp. 1, 1st para. & pp. ln 15 – 23). Examples of the compounds are found in Examples 8.1, 8.2 and 9.1.
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,
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.
Applicant is reminded that claim 20 is claimed in a Product-by-Process format. MPEP §2113 reads, “Product-by-process claims are not limited to the manipulations of the recited steps, only the structure implied by the steps.”
It is well settled that the presence of process limitations in product claims, which product does not otherwise patentably distinguish over the prior art, cannot impart patentability to that product. The addition of a method step in a product claim, which product is not otherwise patentably distinguish over the prior art, cannot impart patentability to that old product." SmithKline Beecham Corp. v. Apotex Corp., 439 F.3d 1312, 1318 (Fed. Cir. 2006) (quoting In re Stephens, 345 F.2d1020, 1023 (CCPA 1965).
The PTO takes the following position with respect to Product- by-Process claims, As stated in ln re Thorpe, 777 F.2d 695, 697, 698,227 USPQ 964, 966 (Fed. Cir. 1985): Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.
In Examination, “the structure implied by the process steps should be considered when assessing the patentability of product-by-process claims over the prior art, especially where the product can only be defined by the process steps by which the product is made, or where the manufacturing process steps would be expected to impart distinctive structural characteristics to the final product. See, e.g., In re Garnero, 412 F.2d 276, 279, 162 USPQ 221,223 (CCPA 1979). "The Patent Office bears a lesser burden of proof in making out a case of prima facie obviousness for product-by-process claims because of their peculiar nature" than when a product is claimed in the conventional fashion. In re Fessmann, 489 F.2d 742, 744, 180 USPQ 324, 326 (CCPA 1974). Additionally, once the Examiner establishes that a product, recited in terms of its process of making, is prima facie unpatentable due to anticipation, Appellants bear the burden of proving "that the prior art products do not necessarily or inherently possess the characteristics of his claimed product." Id. at 698 (quoting In re Fitzgerald, 619 F.2d 67, 70 (CCPA 1980); In re Best, 562 F.2d 1252, 1255 (CCPA 1977)).
Accordingly, applicant's claim is considered a product claim, and the process steps do not have any weight, if the product is known over prior art. In this case the product or composition is known from Trussardi et al. Therefore, the claim is anticipated by the prior art.
Claim Rejections - 35 USC § 102
Claim(s) 20 is rejected under 35 U.S.C. 102(a)(1)& (a)(20 as being anticipated by Dyckman et al. (WO2019/126113).
Rejected claim is to aniline 2, wherein PG denotes Boc (t-butoxycarbonyl).
Dyckman discloses the below compound on page 146 line 24.
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Applicant is reminded that claim 20 is claimed in a Product-by-Process format. MPEP §2113 reads, “Product-by-process claims are not limited to the manipulations of the recited steps, only the structure implied by the steps.”
It is well settled that the presence of process limitations in product claims, which product does not otherwise patentably distinguish over the prior art, cannot impart patentability to that product. The addition of a method step in a product claim, which product is not otherwise patentably distinguish over the prior art, cannot impart patentability to that old product." SmithKline Beecham Corp. v. Apotex Corp., 439 F.3d 1312, 1318 (Fed. Cir. 2006) (quoting In re Stephens, 345 F.2d1020, 1023 (CCPA 1965).
Accordingly, applicant's claim is considered a product claim, and the process steps do not have any weight, if the product is known over prior art. In this case the product or composition is known from Dyckman et al. Therefore, the claim is anticipated by the prior art.
Allowable Subject Matter
Claims 2 and 11 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.
The following is a statement of reasons for the indication of allowable subject matter: In a hydrogenation process wherein the protective group on nitroarene 1 is Boc and the reaction solvent is tert-butyl methyl ether, aniline 2 with a PG of Boc is obtained with good yield and purity. In the process of Applicant’s examples, crystallization can be carried out without complete removal of the TBME aprotic solvent. This differs from the prior arts which require a solvent swap (removal of reaction solvent) before crystallization.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to YATE' K. CUTLIFF whose telephone number is (571)272-9067. The examiner can normally be reached Monday-Friday (8:30 - 5:30).
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 Y. 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.
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/YATE' K CUTLIFF/Primary Examiner, Art Unit 1692
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