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 .
Non-Final Rejection
The Status of Claims:
Claims 1-26 are pending.
Claims 1-26 are rejected.
DETAILED ACTION
1. Claims 1-26 are under consideration in this Office Action.
Priority
2. It is noted that this application is a 371 of PCT/EP2022/057479 03/22/2022, which has a foreign priority document, EPO EP21165202.9 03/26/21.
Drawings
3. None.
IDS
4. The IDS filed on 9/21/23 are reviewed by the examiner.
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.
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 1-26 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.
In claims 1, 8, 12-14,25-26 the term “ derivative” the terms” sulfoxide derivative”,” transition metal derivative, “ a derivative thereof ”, “ an iron derivative”,’ a titanium derivative”, “ sulfoxide derivatives “ are recited. These expressions can be vague and indefinite because the claims doe not explain what is meant by the tern “ derivative(s)”. The examiner recommends to replace it with the definitive term.in the claims.
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 1-11, 15-26 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for molybdenum, zirconium, iron, manganese or titanium, does not reasonably provide enablement for any enantiomerically enriched chiral catalyst or a transition metal generally. The specification does not enable any skilled process chemist or pilot-plant operator to make the invention commensurate in scope with these claims. “The factors to be considered [in making an enablement rejection] have been summarized as the quantity of experimentation necessary, the amount of direction or guidance presented, the presence or absence of working examples, the nature of the invention, the state of the prior art, the relative skill of those in that art, the predictability or unpredictability of the art and the breadth of the claims”, In re Rainer, 146 USPQ 218 (1965); In re Colianni, 195 USPQ 150, Ex parte Formal, 230 USPQ 546. The three issues here are the lack of guidance in the specification, the limited working examples, and the unpredictability of the catalytic arts.
a) Determining if a sulfite of formula (II) would react under any conditions, it would require an oxidation process with a variety of any enantiomerically enriched chiral catalysts or a transition metal generally to produce a 2-(phenylimino)-1,3-thiazolidin-4-one sulfoxide derivative[[s]] of formula (I) , a small quantity of experimentation. b) The direction concerning the various " enantiomerically enriched chiral catalysts or a transition metal generally " is found in lines 20-28, page 8. c) There are 24 working examples of using only iron (III) acetyacetonate catalyst as for representing the " enantiomerically enriched chiral catalyst or a transition metal generally ", pages 15-24. d) The nature of the invention is chemical synthesis to make the 2-(phenylimino)-1,3-thiazolidin-4-one sulfoxide derivative of formula (I). This requires chemical catalysis.
f) The artisan using Applicants' invention to prepare the claimed compounds would be a process chemist or pilot plant operator with a BS degree in chemistry and several years of experience. As suggested by Applicants in the parent application, he would know how to use " iron (III) acetyacetonate with oxidation reactions but be unaware of any other catalyst to use.
g) Chemical reactions are well-known to be unpredictable, In re Marzocchi, 169 USPQ 367, In re Fisher, 166 USPQ 18. Additionally, catalytic processes, such as are present here, are inherently unpredictable. The U.S. District Court District of Connecticut held in MOBIL OIL CORPORATION v. W.R. GRACE & COMPANY, 180 USPQ 418 that “there is an inherent mystery surrounding the unpredictability of the performance of catalysts; a mystery which is generally recognized and acknowledged by chemists in the cracking art. This is one more reason why the presumption of patent validity "should not be disregarded especially in a case of this sort where the intricate questions of [bio]chemistry involved are peculiarly within the particular competence of the experts of the Patent Office.” Merck & Co. v. Olin Mathieson Chemical Corp., 253 F.2d 156, 164, 116 USPQ 484, 490 (4th Cir. 1958)". "The catalytic action can not be forecast by its chemical composition, for such action is not understood and is not known except by actual test, Corona Cord Tire Co. v. Dovan Chemical Corp., 276 U.S. 358, 368-369 (1928). Also see, Application of Grant, 304 F.2d 676, 679, 134 USPQ 248, 250-251 (CCPA 1962); Rich Products Corp. v. Mitchell Foods, Inc., 357 F.2d 176, 181, 148 USPQ 522, 525-526 (2d Cir. 1966), cert. denied 385 U.S. 821, 151 USPQ 757 (1966); Ling-Temco-Vought, Inc. v. Kollsman Instrument Corp., 372 F.2d 263, 268, 152 USPQ 446, 450-451 (2d Cir. 1967); Georgia-Pacific Corp. v. United States Plywood Corp., 258 F.2d 124, 132-133, 118 USPQ 122, 128-129."
h) The breadth of the claims includes the presently unknown list of catalysts embraced by limitation " an enantiomerically enriched chiral catalyst generally ". Thus, the breadth of the claims is moderate.
Claim Rejections - 35 USC § 103
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
5. Claims 1-26 are rejected under 35 U.S.C. 103 as being unpatentable over Koehler et al (US 2014/0315898 A1) in view of Antons et al (US 2013/0172573 A1) and Blumbergs et al (US 3,235,584).
Determination of the scope and content of the prior art
Koehler et al discloses a preparation of 2-( { 2-Fluoro-4-methyl-5-[ (2,2,2-trifluoroethyl)sulfinyl]phenyl }imino )-3-(2,2,2-trifluoroet
hyl)-l ,3-thiazolidin-4-one from 2-( { 2-fluoro-4-methyl-5-[ (2,2,2-trifluoroethyl)sulfanyl]phenyl }imino )-3-(2,2,2-trifluoroethyl)-l ,3-thiazolidin-4-one
in the following steps:
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as in claims 25-26 (partially). At 0-4 ° C., 136 g (0.32 mmol) of 2-( { 2-fluoro-4-methyl-5-[ (2,2,2-trifluoroethyl)sulfanyl]phenyl }imino )-3-(2,2,2-trifluoroethyl)-l ,3-thiazolidin-4-one are initially charged in 3 ml of dichloromethane as in claim 21, 84 mg (0.32 mmol) of meta-chloroperbenzoic acid (70%) as in claims 17, 20, 23 are added and the reaction mixture is stirred at room temperature for another 2 h. A 33% strength sodium thiosulfate solution (peroxide test carried out) and a saturated sodium bicarbonate solution are then added, and the mixture is extracted twice with dichloromethane. The combined organic phases are washed with a saturated sodium carbonate solution, dried over sodium sulfate and filtered, and the solvent is removed under reduced pressure. The residue comprises 136 mg (100% pure, 96% of theory) of the title compound as in claims 1-7 as a lightly colored oil which, over time, crystallizes to give a white solid. (see page 54, pargraphs#0578-0579)
Furthermore, the oxidation of compounds of the formula (Ia) to compounds of the formula (lb) can be performed using an oxidizing agent in a suitable solvent and diluent. Suitable oxidizing agents are, for example, dilute nitric acid, hydrogen peroxide and peroxycarboxylic acids such as meta-chloroperbenzoic acid as in claim 18 (partially). Suitable solvents are inert organic solvents, typically acetonitrile and halogenated solvents such as dichloromethane, chloroform or dichloroethane as in claim 21 .
In addition, a large number of different methods are suitable for generating enantiomerically enriched sulfoxides, as described by A. R. Maguire in ARKIVOC, 2011 (i), 1-110 or by WO2011/006646: metal-catalyzed asymmetric oxidations of thioethers, for example with titanium and vanadium as the most frequently employed catalyst sources, in the form of Ti(O-Pr4) and VO( acac )2, together with a chiral ligand as in claim 8 and an oxidizing agent such as tert-butyl hydroperoxide (TBHP), 2-phenylpropan-2-yl hydroperoxide (CHP) or hydrogen peroxide as in claim ; non-metal-catalyzed asymmetric oxidations employing chiral oxidizing agents or chiral catalysts; electrochemical or biological asymmetric oxidations and also kinetic resolution of sulfoxides and nucleophilic shift (according to Andersen's method) (see page 13, paragraphs#0153-0154).
The current invention, however, differs from the prior art in that the use of the claimed enantiomerically enriched chiral catalyst, the enantiomeric ratio is 50.5:49.5 to 100:0 (R):(S) or (S):(R) enantiomer, the ligand being the compound of formula (III) and the additive being an alkali metal salt of the organic acid in a specific amount in mol% based on the sulfide of formula (II) and the chiral metal-ligand complex in a specific amount in mol% based on the sulfide of formula (II) are unexemplified in the prior art.
Antons et al teaches a catalytic process for preparing 3-triazolyl sulphoxide derivatives in enantiomerically pure or enantiomerically enriched form in the following:
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Compounds of the formula (I) form by the process according to the invention, according to the preparation conditions, in an enantiomer ratio of 50.5:49.5 to 99.5:0.5 ( + ): (-)-enantiomer or (-):(+ )-enantiomer as in claims 2, 25-26 (partially) .
The enantiomeric purity can, if necessary, be increased by different processes. Such processes are known to those skilled in the art and include especially preferential crystallization from an organic solvent or a mixture of organic solvent with water as in claim 22 (see page 2 , paragraphs#0024-0026).
The oxidizing agents which can be used for this reaction are not subject to any particular stipulations. It is possible to use oxidizing agents which are capable of oxidizing corresponding sulphur compounds to sulphoxide compounds. Suitable oxidizing agents for preparing the sulphoxides are, for example, inorganic peroxides, for example hydrogen peroxide, or organic peroxides, for example alkyl hydroperoxides and arylalkyl hydroperoxides. The preferred oxidizing agent is hydrogen peroxide as in claim 24. The molar ratio of oxidizing agent to the sulphide is in the range from 0.9:1 to 4:1, preferably between 1.2:1 and 2.5: l as in claim 23.
The chiral metal-ligand complex is prepared from a chiral ligand and a transition metal compound. Transition metal derivatives are preferably vanadium derivatives, molybdenum derivatives, zirconium derivatives, iron derivatives, manganese derivatives and titanium derivatives as in claims 12-14, very preferably vanadium derivatives. These derivatives can be used, for example, in the form of the transition metal(IV) halides, transition metal(IV) alkoxides or transition metal(IV) acetylacetonates as in claims 15.
The chiral ligand is a chiral compound which is capable, for example, reacting with the vanadium derivatives. Such compounds are preferably selected from chiral alcohols. Preferred chiral ligands likewise include Schiff bases of the formulae (III)
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as in claims 9-11 (see page 3, paragraphs#0035-0038)
In addition, the amount of the chiral metal-ligand complex used, compared to the sulphide, is in the range from 0.001 to 10 mo!%, preferably from 0.1 to 5 mo!%, most preferably 1 to 4 mo!% as in the claim 16. A higher use of chiral metal-ligand complex is possible but economically unviable (see page 3 , a paragraph#0040).
Furthermore, Blumbergs et al describes that the sodium salt of peroxybenzoic acid and the sodium salt of chloro substituted peroxybenzoic acid are known as oxidizing agents in the followings:
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As in claims 18-19 (see col. 1, lines 25-50).
Ascertainment of the difference between the prior art and the claims
The difference between the instant application and the applied Koehler et al art is that the applied Koehler et al art does not expressly teach the use of the claimed enantiomerically enriched chiral catalyst, the enantiomeric ratio is 50.5:49.5 to 100:0 (R):(S) or (S):(R) enantiomer, the ligand being the compound of formula (III) and the additive being an alkali metal salt of the organic acid in a specific amount in mol% based on the sulfide of formula (II) and the chiral metal-ligand complex in a specific amount in mol% based on the sulfide of formula (II). The deficiencies of Koehler et al are partially cured by Antons et al.
The difference between the instant application and the applied Antons et al art is that the applied Antons et al art does not expressly teach the preparation of `2-( { 2-Fluoro-4-methyl-5-[ (2,2,2-trifluoroethyl)sulfinyl]phenyl }imino )-3-`(2,2,2-trifluoroethyl)-l ,3-thiazolidin-4-one from 2-( { 2-fluoro-4-methyl-5-[ `(2,2,2-trifluoroethyl)sulfanyl]phenyl }imino )-3-(2,2,2-trifluoroethyl)-l ,3-`thiazolidin-4-one and the additive being an alkali metal salt of the organic acid `in a specific amount in mol% based on the sulfide of formula (II). The `deficiencies of Antons et al are partially cured by Koehler et al.
3.The difference between the instant application and the applied Blumbergs et al art is that the applied Blumbergs et al art does not expressly teach the preparation of 2-( { 2-Fluoro-4-methyl-5-[ (2,2,2-trifluoroethyl)sulfinyl]phenyl }imino )-3-(2,2,2-trifluoroethyl)-l ,3-thiazolidin-4-one from 2-( { 2-fluoro-4-methyl-5-[ (2,2,2-trifluoroethyl)sulfanyl]phenyl }imino )-3-(2,2,2-trifluoroethyl)-l ,3-thiazolidin-4-one the use of the claimed enantiomerically enriched chiral catalyst, the enantiomeric ratio is 50.5:49.5 to 100:0 (R):(S) or (S):(R) enantiomer, the ligand being the compound of formula (III) and the additive being an alkali metal salt of the organic acid in a specific amount in mol% based on the sulfide of formula (II) and the chiral metal-ligand complex in a specific amount in mol% based on the sulfide of formula (II). The deficiencies of Blumbergs et al are cured by Koehler et al and Antons et al.
Resolving the level of ordinary skill in the pertinent art.
Regarding Claim 1, with respect to the lack of exemplifying the use of the claimed enantiomerically enriched chiral catalyst, Koehler et al does mention generally the methods for generating enantiomerically enriched sulfoxides; for example, the application metal-catalyzed asymmetric oxidations of thioethers with titanium (see page 13, a pargraph#0154); also, Antons et al does teach an example of an enantiomer ratio for using an iron-chiral ligand catalyst (Fe(acac))system for the oxidation process (see page 5, table 2).
Therefore, regardless of showing the transition metal-chiral ligand catalyst system as an example for the claimed preparation in the prior art, it would have been obvious to the skilled artisan in the art to be motivated to incorporate Antons’ iron-chiral ligand catalyst into the Koehler et al preparation in order to generating the claimed enantiomerically enriched sulfoxide. This is because the skilled artisan in the art would expect such combined preparations to be feasible and successful as guidance shown in the prior art.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Koehler et al expressly teaches the preparation of 2-( { 2-Fluoro-4-methyl-5-[ (2,2,2-trifluoroethyl)sulfinyl]phenyl }imino )-3-(2,2,2-trifluoroethyl)-l ,3-thiazolidin-4-one from the starting material, 2-( { 2-fluoro-4-methyl-5-[ (2,2,2-trifluoroethyl)sulfanyl]phenyl }imino )-3-(2,2,2-trifluoroethyl)-l ,3-thiazolidin-4-one in the presence of meta-chloroperbenzoic acid as an oxidant and dichloromethane, whereas Antons et al does teach the catalytic process for preparing sulphoxide derivatives in enantiomerically pure or enantiomerically enriched form in the presence of chiral transition metal(IV) acetylacetonates-ligand complex catalyst. Furthermore, Blumbergs et al describes that either the sodium salt of peroxybenzoic acid or the sodium salt of chloro substituted peroxybenzoic acid can be used as the oxidizing agent.
Koehler et al and Antons et al and Blumbergs et al are closely related to one and another with respect to the preparation process vs. chiral metal -ligand complex catalyst for the enantiomerically enriched form vs. the oxidizing agent.
So, if the skilled artisan in the art had desired to form enantiomerically pure or enantiomerically enriched form of 2-( { 2-Fluoro-4-methyl-5-[ (2,2,2-trifluoroethyl)sulfinyl]phenyl }imino )-3-(2,2,2-trifluoroethyl)-l ,3-thiazolidin-4-one, it would have been obvious to the skilled artisan in the art to be motivated to incorporate Antons’ iron-chiral ligand catalyst in combination of Blumbergs’ sodium salt of peroxybenzoic acid as an alternative into the Koehler et al preparation in order to generating the claimed enantiomerically enriched sulfoxide. This is because the skilled artisan in the art would expect such combined preparations to be feasible and successful as guidance shown in the prior art.
Conclusion
Claims 1-26 are rejected.
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/TAYLOR V OH/Primary Examiner, Art Unit 1625 2/28/2026