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 preliminary amendment, filed Dec. 14, 2022. As filed, claims 16-30 are pending.
Priority
This application filed 12/14/2022 is a National Stage entry of PCT/EP2021/066048 , International Filing Date: 06/15/2021 claims foreign priority to 20180528.0, filed 06/17/2020.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) filed on 12/27/2022, 01/13/20233, 6/17/2025 have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
Claim Objections
1.Claims 16, 17, 19, 22, 23 are objected for reciting improper Markush language: the recitation in claims for definition of variables of Markush formula (I) should be changed to “selected from the group consisting of”. See MPEP 803.02. “A Markush-type claim recites alternatives in a format such as "selected from the group consisting of A, B and C."
2. Claim 29 recites the “use” language. The objected claim is not viewed as “use” claim, but proper transition wording should be present.
Appropriate correction is required.
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 28 is 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.
Regarding claim 28, the phrase "preferably" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Claim Rejections - 35 USC § 102
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 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)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(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.
Claims 16, 18, and 20 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by SU 1728218, April 1992, by Vasilevich et al. (the ‘218 publication”; cited by Applicants in IDS).
The ‘218 publication teach the croconate dipiperizine compound (abstract, experimental) shown below as displayed in Registry data base:
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The compound of the prior art corresponds to compound of claimed Formula I wherein R1 and R5 are each H (instant claim 18); R2 and R6 are each H, R3 and R4 together with the nitrogen to which they are bonded form a 6-membered saturated heterocyclic ring; R7 and R8 together with the nitrogen to which they are bonded form a 6-membered saturated heterocyclic ring (instant claim 16); R 1 and R5 are the same;
R2 to R4 are the same; and R6 to R8 are the same (instant claim 20).
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.
1. Claims 16-26 are rejected under 35 U.S.C. 103 as being unpatentable over Georgopoulos et al. Journal of Molecular Structure 1108 (2016) 542-551 (cited in the PTO-892 attached herewith) and further in view of Berge et al., J. Pharm. Sci. 1977, Vol. 66 1-18 (cited in the PTO-892 attached herewith).
The article by Georgopoulos teaches croconate dianion (C5O5 2-) salts amine stabilized with tetraalkylammonium ions and supramolecular studies of the intermolecular interactions resulting from the association of different chemical entities which give rise to compounds with a wide range of catalytic, magnetic, optic, biological, microporous and electronic applications (abstract, introduction pages 542).
The compound 3 [N(C2H5)4]2(C5O5)$5H2O disclosed by Georgopoulos on Fig 4 and experimental, comprising two tetraethylammonium cationic blocks electrostatically interacting with only one croconate dianion- shown below as displayed din Registry Data base, is structurally similar to the claimed compounds of formula I:
IT 1865761-94-9P
RL: PRP (Properties); SPN (Synthetic preparation); PREP (Preparation)
(crystal structure; IR, Raman and structural investigation of oxocarbon
salts with tetraalkylammonium ions)
RN 1865761-94-9 CAPLUS
CN Ethanaminium, N,N,N-triethyl-, salt with
4,5-dihydroxy-4-cyclopentene-1,2,3-trione(2-), hydrate (2:1:5) (CA INDEX
NAME)
CM 1
CRN 15110-70-0
CMF C5 O5
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CM 2
CRN 66-40-0
CMF C8 H20 N
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Regarding instant claim 26 the article discloses in water (the pharmaceutically acceptable composition).
The difference between the teaching of the prior art and instant claims is that the prior art teaches a tetraethylammonium salt of croconic acid, instead of the croconic acid amine salts of formula I as claimed.
However, salt formation of a drug is a widely recognized and routinely used solution available for resolving ordinary stability, bioavailability, and manufacturing problems arising in pharmacologic compounds as stated in the article by Berge:
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The article by Berge discuss that for the pharmaceutical salts preparation, the salt forming agents are selected on a practical basis that involves cost of materials, ease of crystallization, percent yield as well as stability, hygroscopicity (page 1, col. 2), toxicity (page 3 and page 15) and solubility (page 7), formulation effects and bioavailability (page 11); higher acid salts such as caproic acid which showed increased diffusion from similar emulsions since these salts are soluble in both water and oil are discussed on page 11.
Therefore, a person having ordinary skill in the art before the effective filing date of the claimed invention would have viewed various capric acid salt forms of spermidine as prima facie obvious in view of the free base of the compound. The optimization of a pharmaceutical salt of a compound is routine in the pharmaceutical art and unpatentable absent unexpected results. The courts have established that the routine variation of a pharmaceutical salt does not represent a patentable modification absent a showing of unexpected results. Pfizer, Inc. v. Apotex, Inc., 480 F.3d 1348, 82 USPQ2d 1321 (Fed. Cir. 2007). See also MPEP 2143.
In 2007, the Supreme Court clarified that standard for obviousness in KSR International Co. v. Teleflex Inc., USPQ2d, 1385, 1398; 127 SCt 1727; 167 Led2d 705; 550 US 398 (2007) (stating: “When there is a design need or market pressure to solve a problem and there are a finite number of identified, predictable solutions, a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. . . . If this leads to the anticipated success, it is likely the product not of innovation but of ordinary skill and common sense. In that instance the fact that a combination was obvious to try might show that it was obvious under § 103.”)
In this case, the use of organic amine salts, such as arginine, piperazine and formulations of a drug were known options within the technical grasp of one of ordinary skill in the art before the effective filing date. Success in the use of such arginine, piperazine salts of croconic acid would have been expected to work as taught in the prior art with the reasonably expectation that additional pharmaceutically useful amine salts of croconate dianion would be obtained.
Therefore, the claimed invention as a whole is prima facie obvious over the teachings of the prior art.
2.Claims 16-30 are rejected under 35 U.S.C. 103 as being unpatentable over Georgopoulos et al. Journal of Molecular Structure 1108 (2016) 542-551 (cited in the PTO-892 attached herewith) and further in view of Berge et al., J. Pharm. Sci. 1977, Vol. 66 1-18 (cited in the PTO-892 attached herewith) as applied to claims 16-26 above and further in view of US 8,454,940 B2, 2013 by Wagner et al. (cited by Applicants in IDS).
The teachings of the prior art by Georgopoulos and Berge regarding claims 1-26 are discussed above. Regarding instant claims 27-30, pertaining to composition further comprising at least one additional UV filter, this is limitation discussed in the ’940 patent. The ‘940 patent teaches stabilizing composition comprising:
(a) an effective stabilizing amount of at least one merocyanine derivative having an absorption maximum of 350 to 400 nm, and (b) at least one UV filter selected from benzotriazole derivatives; and optionally ( c) at least one excited state quencher;
for the protection of body care and household products against the deleterious effects of light, heat and oxygen (abstract, claims).
Therefore, the prior art relied upon, and knowledge generally available in the art before the effective filing date provide the suggestion that would have motivated the skilled artisan to photostabilize compositions containing amine salts of croconic acid by addition of an additional UV filter, and have reasonable expectation of success.
Regarding recitation of use of compounds and compositions in body-care product or household cleaning and treating agents, or to protect skin against UV radiations- this represents a property that is an inherent property of the compounds (compositions), and there is no evidence stating that the compounds according to the prior art, would not produce the same effect when utilized in such applications. The discovery of a previously
unappreciated property of a prior art composition, or of a scientific explanation for the
prior art's functioning, does not render the old composition patentably new to the
discoverer. Atlas Powder Co. v. lreco Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943,
1947 (Fed. Cir. 1999), see MPEP 2112. Thus, the claiming of an unknown property
inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977).
In conclusion, one skilled in the art would have found the claimed compound and compositions thereof prima facie obvious because the prior art specifically teach both amine salts of croconic acid compounds of photochemical properties as well as stabilizing compositions by addition of UV filter as required by instant claims. The motivation to make the claimed compounds and compositions derives from the expectation that structurally similar compounds/compositions would possess similar activity (i.e. stabilized composition comprising a light stabilizer to protect ingredients against photolytic degradation ).
Therefore, absent a showing of unexpected results, the instant invention would have been obvious.
Conclusion
Claims 16-30 are rejected.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to:
Ana Muresan
(571) 270-7587 (phone)
(571)270-8587 (fax)
Ana.Muresan@uspto.gov
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692