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 1-20 are pending.
Claims 1-7, and 9-20 are rejected.
Claims 8 and 14 are objected
DETAILED ACTION
1. Claims 1-20 are under consideration in this Office Action.
Priority
2. It is noted that this application is a 371 of PCT/EP2023/060257 04/20/2023 which has a foreign priority document, UNITED KINGDOM GB2206290.5 04/29/2022.
Drawings
3. None.
IDS
4. The IDS filed on 10/25/2024 has been reviewed by the examiner.
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 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.
Claim Objections
Claims 8 and 14 are objected to because of the following informalities:
In claim 14, the phrase” claim 1, any of the preceding claims” is recited. This expression is improper because the claim 14 becomes a multiply dependent claim.
Appropriate correction is required.
Claim 8 is 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.
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.
Claim 3, 5,11, 17 and 19 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c).
In the present instance, claim 3 recites the broad recitation” selected from methylsulfonyl, chlorine and/or bromine”, and the claim also recites “ preferably chlorine”, which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
claim 5 recites the broad recitation “selected from butanol, pentanol, or 2-methoxyethanol,”, and the claim also recites “preferably butanol”, which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
claim 11 recites the broad recitation “the ratio of base to co-base is from 10:1 to 1:2,”, and the claim also recites “preferably from 5:1 to 1:1 ”, which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
claim 17 recites the broad recitation” comprising a solvent distillation step”, and the claim also recites “ preferably only one solvent distillation step”, which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
The examiner recommends to put the narrowed limitations to their dependent claims.
In claim 5, the phrase “selected from butanol, pentanol, or 2-methoxyethanol” is recited. This expression is improper because the Markush expression would require to put “and “ instead of “or “ at the end of the claim.
In claim 19, the phrase “preparing pinoxaden comprising a process as defined in claim 1” is recited . This expression can be are vague and indefinite because the claim does not specify how the compound of formula (I) is converted into pinoxaden in steps along with any reagents and solvent system at any reaction conditions.
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)(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.
5. Claim 20 is rejected under 35 U.S.C. 102(a)(2) as being anticipated clearly by Kotelko et al (PL 123646).
Kotelko et al discloses the following compound:
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, wherein R denotes a methyl.
(see example 2, col 1, line 17-line 18). This is identical with the claim.
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.
6. Claims 1-7, 9-18 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Faber et al (WO 2006/045587A1).
Determination of the scope and content of the prior art
Faber et al discloses a process for the preparation of a (1,4,5]-oxadiazepine derivative, which comprises reacting a 4,5-diacyl-[1,4,5]-oxadiazepine with a base in a polar solvent and at elevated temperature.
Example 5: Preparation of 4,5-diacetyl-[1,4,5]-oxadiazepine as in claim 20
A mixture consisting of 792 g of dimethyl sulfoxide, 140 g of N,N'-diacetylhydrazine (content 99.5%), 33 g of potassium carbonate, 142 g of potassium hydroxide (content 95%) as in claims 9-13 and 6.6 g of tetramethylammonium chloride is prepared at from 80 to 85°C and evacuated to from 20 to 40 mbar. Under that vacuum and at the same temperature, 258 g of 2,2'-dichlorodiethyl ether as in claims 1-4 are added dropwise in the course of 2 hours and the reaction mixture is then maintained under those conditions for 3 hours. During the dropwise addition and the maintenance period, the water formed under the reaction conditions is removed by distillation as in claim 15 and 17(partially). After cooling to from 20 to 25°C, inorganic salt is filtered off as in claim 16, the filtrate is concentrated by evaporation and the residue is crystallised from 1-pentanol as in claim 18 . 125.6 g of 4,5-diacetyl-[1,4,5]-oxadiazepine having a content of 93% are obtained, which corresponds to a yield of 52.3%.
The 4,5-diacyl-[1,4,5]-oxadiazepines of formula I used as starting materials are known and the yield of such starting materials can be improved in the case of the reaction of N,N'-diacylated hydrazine with, for example, 2,2'dichlorodiethyl ether, by using hydroxides of alkali metals and alkaline earth metals as the base and by carrying out the reaction with the addition of a phase transfer catalyst, such as, for example, TBACI (tetrabutylammonium chloride), as in claims 6-7, TBABr (tetrabutylammonium bromide), TMACI (tetramethylammonium chloride) or TMABr (tetrabutylammonium bromide) or benzyltriethylammonium chloride, benzyl-triethylammonium bromide or Aliquat, and/or by continuously distilling off the water formed during the reaction from the reaction mixture (see page 2 ,lines 1-10).
Furthermore, the reaction is carried out in polar solvents, preferably in water or alcohols that preferably have a boiling point above 100°C, such as, for example, n-butanol, n-pentanol, as in claims 1 and 4-5 cyclohexanol, phenol, benzyl alcohol and especially glycol, diethylene glycol,glycerol and C1-C4alkoxy-C1-C4alcohols, such as methoxyisopropanol and ethoxyethanol, and also DMSO [(CH3)2 SO], sulfolane [(CH2)4SO2], NMP [(CH2)sCONCH3], DMA[CH3CON(CH3)2] or DMF [HCON(CH3)2] or mixtures thereof, with preference being given to NMP, DMSO and, especially, water (see page 2 , line 27 to page 3 , line 2).
Example 7: Preparation of [1,4,5]-oxadiazepine
A mixture of 18.6 g of 4,5-diacetyl-[1,4,5]-oxadiazepine (100%), 0.54 g of tetramethylammonium chloride and 100 g of sulfolane is heated to Ti=120-125°C. as in claim 14 In the course of 30 min., 4.0 g of potassium hydroxide (95%) are added and the reaction mixture is maintained at that temperature. 0.50 g of water is then added. After a further addition of 8.0 g of potassium hydroxide (95%) over a period of two hours, the reaction mixture is maintained at constant temperature for a further three hours. The reaction mixture is then cooled to room temperature and filtered, and the residue is subsequently washed with sulfolane. The sulfolane filtrate obtained (weight 214.9 g) has a content of 1.74%, which corresponds to a yield of 3. 7 4 g/100% or 38.1 % of theory. (see page 7, example 7).
The instant invention, however, differs from the prior art in that the claimed reaction being carried out at least one of the solvent reflux temperature or from 110 to 125 °C is unspecified in the prior art.
Ascertainment of the difference between the prior art and the claims
The difference between the instant application and the applied Faber et all art is that the Faber et al does not expressly teach that the claimed reaction is carried out at least one of the solvent reflux temperature or from 110 to 125 °C
Resolving the level of ordinary skill in the pertinent art.
Regarding the Claim 14 with respect to the lack of disclosing that the claimed reaction is carried out at least one of the solvent reflux temperature or from 110 to 125 °C, the prior art does mention indirectly that in the preparation of [1,4,5]-oxadiazepine, the reaction can take place in the temperature range from 120 to 125°C (see page 7, example 7). Also, the reaction is carried out in polar solvents, preferably in water or alcohols that preferably have a boiling point above 100°C(see page 2, lines 27-28).
From these teachings, it seems reasonable for the skilled artisan in the art to carry out the preparation of 4,5-diacetyl-[1,4,5]-oxadiazepine in the alcoholic solvent at a high reaction temperature at least above 100°C .
Therefore, it would have been obvious to the skilled artisan in the art to be motivated to increase the reaction temperature to 1100C when the alcoholic solvent is applied as an alternative. This is because the skilled artisan in the art would expect such a manipulation to be within the purview of the skilled artisan in the art.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Faber et al expressly discloses the process for the preparation of the 4,5-diacyl-[1,4,5]-oxadiazepine by reacting N,N'-diacetylhydrazine with 2,2'-dichlorodiethyl ether
In the presence of potassium carbonate and potassium hydroxide and tetramethylammonium chloride as a phase transfer catalyst.
Although the prior art does not exemplify the use of the alcoholic solvent at a high reaction temperature, the prior art does give at least guidance that alcohols preferably have a boiling point above 100°C.
So, if the skilled artisan in the art had desired to carry out the preparation of the 4,5-diacyl-[1,4,5]-oxadiazepine in the alcoholic solvent as an alternative, it would have been obvious to the skilled artisan in the art before the effective filing date of the claimed invention to be motivated to increase the reaction temperature to 1100C by a routine experimentation. This is because the skilled artisan in the art would expect such a manipulation to be successful and feasible as guidance shown in the prior art.
Conclusion
Claims 1-7 and 9-20 are rejected.
Claims 8 and 14 are objected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAYLOR V OH whose telephone number is (571)272-0689. The examiner can normally be reached 8:00-5:00.
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/TAYLOR V OH/Primary Examiner, Art Unit 1625 8/8/2026
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