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 the Claims
Claims 1-13 are pending.
Priority
Applicant’s claim for benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, or 365(c) is acknowledged. This application is a national stage entry of and claims priority to Application Serial No. PCT/CN2022/131867, filed 11/15/2022; and further claims priority to FOR application number CN202111361147.X, filed 11/17/2021.
Information Disclosure Statement
All references from IDS(s) received on 5/10/2024 and 3/22/2025 have been considered unless marked with a strikethrough.
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 4, 6-10, and 13 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 4 recites the broad recitation “the inorganic alkali is selected from the group consisting of potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, sodium hydride and calcium hydride,” and “preferably sodium hydroxide or potassium hydroxide;” which is the narrower statement of the range/limitation. Along the same line, claim 4 also recites “the organic alkali is selected from the group consisting of lithium tert-butoxide, potassium tert-butoxide, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide and pyridine” followed by “preferably lithium tert-butoxide, sodium methoxide or sodium ethoxide.” Claim 6 recites “the organic solvent is one of ethers, haloalkanes, aromatic hydrocarbons, amides, esters and C3-C6 ketones, or any combination thereof,” followed by “preferably one of tetrahydrofuran, 2-methyltetrahydrofuran, dichloromethane, toluene, N,N-dimethyformamide, ethyl acetate, acetone and methyl isobutyl ketone, or any combination thereof.” Claim 7 recites “the molar ratio of the intermediate I to the intermediate II is 0.5: 1 to 2: 1,” followed by “preferably 0.97: 1 to 1.5: 1.” Claim 8 recites “the molar ratio of the alkali to the intermediate I is 1: 1 to 4: 1,” followed by “preferably 1: 1 to 3: 1.” Claim 9 recites “a temperature of the reaction is -100C to 50°C,” followed by “preferably 04C to 50°C.” Claim 10 recites “a duration of the reaction is 1 h to 12 h,” followed by “preferably 2 h to 5 h.” Claim 13 recites “the organic solvent is acetone or dichloromethane,” followed by “preferably acetone,” 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 Rejections - 35 USC § 103
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 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
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.
Claims 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over Rao, D. et al. (WO2013046211A1; cited in IDS filed 05/10/2024; “Rao”).
Rao teaches a process for preparing 5-chloro-n-({(5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl) phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophene-carboxamide (aka rivaroxaban) through the same intermediates (Claim 1) used in instant claim 1 in the presence of a base (Line 25, Claim 1) and in an organic solvent (Claim 7). See Example 7 of Rao.
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(Rao, Claim 1, R1= -C(O)-OR4, where R4 can be a substituted or unsubstituted phenyl, as required by instant claims 1-2)
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(Rao, Claim 1, R2 and R3 can be H and W can be a halogen, as required by instant claim 1).
The instant claims require a phenyl-based carbamate for formula I. Although Rao teaches a phenyl as a possibility in the R1 position, it would have to be chosen from a list of possible R1 substituents. Therefore, Rao fails to teach an anticipatory embodiment but does teach the limitations of the instant claims.
Rao teaches the base can be lithium tert-butoxide (Claim 2), as required by instant claims 3-5.
Rao teaches the reaction takes place in an organic solvent, such as DCM (Claim 7), as required by instant claims 6 and 13.
Rao teaches many variations of synthetic methods and equivalents but one example is in Example 7 where instant intermediate II is in 1.28 equivalents to intermediate I. The alkali was added in 2.45 equivalents to intermediate I. These fall within the molar ratio limitations of instant claims 7-8.
Rao teaches the process can be performed at a temperature from 0C to the boiling point of the solvents used from anywhere between 30 minutes and 24 hours, as required by instant claims 9-10.
Rao teaches the work-up process can be as the resultant mixture poured into water and the org. layer was separated. The aq. layer was extracted with dichloromethane (100 ml) and the combined org. extract was washed with dil. HCl (50 ml) followed by water (2x 50 ml) and concentrated to get crude compound. Concentrated is used interchangeably in Rao with concentrated in vacuo. Rao teaches many variations of work-up methods. This teaches the limitations of instant claims 11-13.
The Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385,
1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper "functional approach" to the determination of obviousness as laid down in Graham.
Examples of rationales that may support a conclusion of obviousness include:
Combining prior art elements according to known methods to yield predictable results;
Simple substitution of one known element for another to obtain predictable results;
Use of known technique to improve similar devices (methods, or products) in the same way;
Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
"Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
Applying KSR example rationale (B), it would have been prima facie obvious to extract the methods taught by Rao and substitute -Ph for -CH2Ph in the R1 position of Formula III because the genus teaches that a Ph would also perform the leaving group function and structurally similar compounds are expected to have similar properties.. Therefore, claims 1-13 would be obvious to a person skilled in the art at the time.
Conclusion
Claims 1-13 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to NICOLA MARIA BAUER whose telephone number is (703)756-1269. The examiner can normally be reached Monday-Friday 7:30-5 EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clint Brooks can be reached at (571) 270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/N.M.B./Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
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