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 .
DETAILED ACTION
This Office action is responsive to Applicant's Response to Election/Restriction, filed February 24, 2026. As filed, claims 1-11 are pending in the instant application.
Priority
This application filed 05/16/2023 is a National Stage entry of PCT/JP2021/047078 , International Filing Date: 12/20/2021 claims foreign priority to 2020-214115, filed 12/23/2020.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
Election/Restrictions
Applicant's election with traverse of dinoprostone as the single species of the compound of Formula (1), as supported by the present application at, for example, specification paragraph 0003. Dinoprostone is a compound of Formula (1), wherein P1 is a hydrogen atom, P2 is a hydrogen atom, is a double bond, R1 is a pentyl group (i.e., a linear C1-6 alkyl group), A is a 2-hexenylene group, R2 is a hydroxy group, and the double bond of the "A" group is in the Z configuration; Species (b) - (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5- phenylpentyl]cyclopentyl]hepto-5-enoic acid (i.e., (Z)-IFL-FA) as the single species of the compound of Formula (2), as supported by the present application at, for example, Example 1. (Z)-IFL-FA is a compound of Formula (2), wherein P1 is a hydrogen atom, P2 is a hydrogen atom, ~ is a single bond, R1 is a 2-phenylethyl group (i.e., a linear C1-6 alkyl group substituted with a phenyl group), A is a 2-hexenylene group, R2 is a hydroxy group, and the double bond of the "A" group is in the Z configuration; Species (c)- as mentioned above, the geometric configuration of the olefin in the "A" group of each of the elected species for the compound of Formula (1) and the compound of Formula (2) is the Z configuration (i.e., a cis olefin). and species d) a silica gel modified with a, as supported by the present application at, for example, specification paragraph 0017 in the reply filed on 02/24/2026 is acknowledged.
The traversal is on the ground(s) that compounds of Formula (1) and Formula (2) do share a common structure and do belong to a recognized class of chemical; each of the claimed compounds of Formula (1) and Formula (2) contain a cyclopentanol substituted with a C3-10 alkenylene group. Applicant has unexpectedly discovered that the claimed method is particularly well-suited for separating E/Z (cis/trans) geometric isomers of the compound represented by Formula (1) or Formula (2). Thus, the claimed compounds of Formula (1) and Formula (2) share a cyclopentanol substituted with a C3-10 alkenylene group having E/Z ( cis/trans) geometric isomers, which are exploited to achieve separation.
Applicants’ argument has been carefully considered and found persuasive.
The species election requirement therefore withdrawn.
Claims 1-11 will be examined on the merits herein.
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 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 of this title, 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.
Claims 1-11 are rejected under 35 U.S.C. 103 as being unpatentable over Wu et al Yaoxue Tongbao (1980), 15(12), 37 (cited by Applicants in IDS) and further in view of Sykora et al. J Sep Sci 2019;42:89–129 (cited in PTO-892 attached herewith).
The prior art by Wu discloses purification of biosynthetic product PGE2 Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z:, 13E, 15S) - RN 363-24-6 Z isomer of structure shown below, by a column containing AgNO3-treated silica gel stationary phase by using EtOAc-HOAc-petroleum ether-H2O (200:22.5:125:5) and EtOAc-HOAc-isooctane-H2O (200:22.5:140:5) as solvent systems.
The compound of the prior art corresponds to claimed formula (2) in which P1, P2 are each hydrogen ( instant claims 1, 4, 7, 8), A is a 2-hexenylene group
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(instant claim 2), R1 is
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(instant claim 3, 6) and R2 is hydroxy group.
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The differences between the teaching of the prior art and the claims at issue is that the prior art teaches AgNO3-treated silica gel stationary phase for separation of the geometrical isomers while instant claims require acid modified silica with a carboxy group.
However, using acid modified silica gel for separation of isomers is known in the prior art.
The review article by Sykora teaches chromatographic stationary phases including sulfo or carboxy modified silica for separation of mixtures including isomer separation and discuss that such stationary phase possessing distinct selectivity than currently available commercial columns (abstract; Table 1 on page 91-96; instant claims 5, 9-11).
It would have been obvious to one of ordinary skill in the art at the time of the invention to separate the isomers of prostaglandins by modified silica as stationary phases as discussed by Wu and to utilize acid modified silica as stationary phase as taught by Sykora, because the prior art teaches that alternative modified silica gel stationary exhibit enhanced selectivity in the separation of isomers.
In conclusion, the prior art as a whole as taught by Wu and Sykora teach the elements of the claimed method for separating isomers of prostaglandins, that the invention would be prima facie obvious to one of ordinary skill. Therefore, before the effective filing date of the claimed invention based on the teachings of the cited prior art, one of ordinary skill in the art would have an expectation of success in arriving at the claimed invention.
"Exemplary rationales that may support a conclusion of obviousness include: (A) Combining prior art elements according to known methods to yield predictable results ". See MPEP § 2143 .
Consequently, absent a showing of unexpected results, the instant claims are obvious over the prior art.
Conclusion
Claims 1-11 are rejected.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANA MURESAN whose telephone number is (571)-270-7587. The examiner can normally be reached on Monday through Friday, 8:30 am to 5:30 pm EST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett 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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/ANA Z MURESAN/Primary Examiner, Art Unit 1692
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