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 1-16 are pending.
Claims 12-14 are rejected.
Claims 1-11 and 15-16 are allowable.
DETAILED ACTION
1. Claims 1-16 are under consideration in this Office Action.
Priority
2. It is noted that this application is is a 371 of PCT/CN2023/094661 05/17/2023, which has a foreign priority document, CHINA CN202210552617.9 05/19/2022.
Drawings
3. The drawings field on 11/13/2024 are accepted by the examiner.
IDS
4. The IDS filed on 11/13/24 & 12/17/25 have 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 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 12-14 are rejected under 35 U.S.C. 103 as being unpatentable over Owen et al (WO 2021/250648 A1)) .
Applicants claim the following claims:
12 (Currently amended). A method for treating the new coronavirus in a subject in need thereof, comprising administering the crystal form A of compound of formula (I) of claim 1 to the subject.
13 (New). A method for treating the new coronavirus in a subject in need thereof, comprising administering the crystal form B of compound of formula (I) of claim 6 to the subject.
14 (New). A method for treating the new coronavirus in a subject in need thereof, comprising administering the pharmaceutical composition of claim 11 to the subject.
Determination of the scope and content of the prior art
Owen et al discloses a compound of (1R,2S,5S)-N-{(1 S)-1-Cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}-6,6-dimethyl-3-[3-methyl-N-(trifluoroacetyl)-L-valyl]-3-azabicyclo[3.1.0]hexane-2- carboxamide , which is used in the method of treating a coronavirus infection in a patient by administering the compound in the followings:
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(see page 42, lines 4-10; page 314, claim 5)
19. A method of treating a coronavirus infection in a patient, the method comprising administering a therapeutically effective amount of a compound according to any one of claims 5 to 14 to a patient in need thereof.
(see page 315, claim 19)
Furthermore, it describes (1R ,2S,5S)-N-{( 1 S)-1-Cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}-6,6-dimethyl-3-[3-methyl-N-(trifluoroacetyl)-l-valyl]-3-azabicyclo[3.1.O]hexane-2-carboxamide (13), Solid Form 1 (see page 1
36, lines 1-4) and the method of collection of the powder X-ray diffraction data is described in Alternate Synthesis of Example 13, methyl tert-butyl ether solvate, Step 8.
In addition, table C shows selected powder X-ray diffraction peaks for 13, Solid Form 1 (see pages 136-137).
Moreover, the compound of Formula I, I' and I" including hydrates, solvates, isomers, crystalline and non-crystalline forms, isomorphs, polymorphs, and metabolites thereof (see page 53, lines 15-16).
In the case of SARS-CoV-2 inhibitor compounds, prodrugs, salts, or solvates that are solids, it is understood by those skilled in the art that the compound, prodrugs, salts, and solvates used in the method of the invention, may exist in different polymorph or crystal forms, all of which are intended to be within the scope of the present invention and specified formulas(see page 62, lines 20-24)
Also, the compounds may be administered by any suitable route, preferably in the form of a pharmaceutical composition as in claim 14 (partially) adapted to such a route, and in a dose effective for the treatment intended. (see page 66, lines 4-6) The active compounds and compositions, for example, may be administered orally, rectally, parenterally, or topically.
The instant invention, however, differs from the prior art in that the claimed crystal forms A and B of compound of formula(I) and a pharmaceutical composition containing the crystal form B of formula(I) are unspecified in the prior art.
Ascertainment of the difference between the prior art and the claims
1. The difference between the current application and the applied Owen et al art is that the applied Owen et al art does not expressly teach the claimed crystal forms A and B of compound of formula(I) and a pharmaceutical composition containing the crystal form B of formula(I).
Resolving the level of ordinary skill in the pertinent art.
Regarding the Claims 12-14 with respect to the lack of disclosing the crystal forms A and B of compound of formula(I) and a pharmaceutical composition containing the crystal form B of formula(I), the prior art does recognize that the compound of Formula I, I' and I" can exist and include crystalline and polymorphs (see page 53, lines 15-16). This means that the prior art compound, (1R,2S,5S)-N-{( 1 S)-1-Cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}-6,6-dimethyl-3-[3-methyl-N-(trifluoroacetyl)-l-valyl]-3-azabicyclo[3.1.O]hexane-2-carboxamide (13), can have different polymorphic forms besides Solid Form 1 (see pages 136-137). The relationship between the claimed crystal forms A and B of compound of formula(I) and the prior art crystalline Form 1 is that each has different crystalline structures with respect to the molecules being packed together in distinct geometric arrangements or conformations even though they have the exact same chemical compound. Also, it teaches that the compounds may be administered by any suitable route, preferably in the form of a pharmaceutical
composition (see page 66, lines 4-6), which may imply that the pharmaceutical composition can contain the crystal form B of formula(I).
So, if the skilled artisan in the art had desired to form the crystal forms A and B of compound of formula(I) and /or a pharmaceutical composition containing the crystal form B of formula(I) as an alternative crystalline Form 1 of the prior art compound to be used for the method of treating a new coronavirus infection in a patient, it would have been obvious to the skilled artisan in the art to be motivated to investigate the various polymorphic forms including crystal forms A and B of the prior art compound by a routine experimentation. This is because the skilled artisan in the art would expect to find the crystal forms A and B of the prior art compound, which is within the purview of the skilled artisan in the art.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Owen et al expressly discloses the method of treating a coronavirus infection in a patient by administering the compound of (1R,2S,5S)-N-{(1 S)-1-Cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl}-6,6-dimethyl-3-[3-methyl-N-(trifluoroacetyl)-L-valyl]-3-azabicyclo[3.1.0]hexane-2- carboxamide or its polymorphic form of solid form 1 having powder X-ray diffraction peaks. This compound is the same compound as the claimed compound in spite of the lack of the same x-ray powder diffraction characteristic peaks as the claimed crystal form A and B.
Although Owen et al does not teach the claimed crystal forms A and B of compound of formula(I) and a pharmaceutical composition containing the crystal form B of formula(I) to be used for the method of treating a coronavirus infection in a patient, Owen et al does mention that various crystal forms or polymorphic forms for the prior art compound can exist, which does include the crystal forms A and B of compound of formula(I).
So, if the skilled artisan in the art had desired to form the crystal forms A and B of compound of formula(I) and a pharmaceutical composition containing the crystal form B of formula(I) as an alternative crystalline Form 1 of the prior art compound to be used for the method of treating a new coronavirus infection in a patient, 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 investigate the various polymorphic forms including crystal forms A and B of the prior art compound by a routine experimentation. This is because the skilled artisan in the art would expect to find the crystal forms A and B of the prior art compound, which is within the purview of the skilled artisan in the art.
Conclusion
Claims 12-14 are rejected.
Claims 1-11 and 15-16 are allowable.
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 8/27/2026
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