DETAILED ACTION
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 .
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.
This office action is a response to applicant’s communication submitted February 16, 2024, wherein claims 14, 16, 21 was preliminarily amended, and claims 19 and 22-43 were canceled. This application is a 371 of PCT/US2022/075218 filed 08/19/2022 and claims benefit of US provisional application 63/234,806 filed 08/19/2021.
Claims 1-18 and 20-21 are pending in this application.
Claim Interpretation
Claims 14-15 are product by process claims. The Examiner notes that, "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process" In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (See MPEP 2113 (I)).
Drawings
The drawings are objected to because the graph in figure 2 appears to be missing data points. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Rejections - 35 USC § 112 (b)
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 8 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.
Claim 8 recites the limitation "cyclodextrin-modified compound". There is insufficient antecedent basis for this limitation in the claim. Previous claims used the phrase "cyclodextrin-modified agent”.
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)(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 1-4, 8, 11-12, 14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Franco (Polymers, 2021, published January 13, 2021, IDS filed February 16, 2024).
Regarding claims 1-4, 8, 11-12, 14: Franco teaches rutin (RUT)–beta-cyclodextrin (beta-CD) inclusion complexes are prepared by Supercritical AntiSolvent (SAS) precipitation (abstract). The dissolution tests reveal a significant improvement in the release rate of RUT from inclusion complexes (abstract). Franco teaches increased bioavailability is a consequence of RUT dissolution rate (pg. 1, para. 3). The method comprises beta-cyclodextrin and rutin solubilized in DMSO (i.e. solvent), and experiments were performed at a temperature of 40 C and 9, 12, 15 Mpa (pg. 3, paras. 3-4, pg. 5, para. 3, table 1). Franco teaches the rutin-beta-cyclodextrin complex had a higher dissolution rate than rutin alone (pg. 11, para. 2). Wherein the rutin-beta-cyclodextrin complex has increased dissolution rate, it consequently has higher bioavailability when compared to rutin alone, absent evidence to the contrary. Franco teaches the molar ratio of cyclodextrin:rutin was 2:1 (pg. 5, table 1). Franco teaches dissolution of the complex in PBS (i.e. solution in water, a pharmaceutically acceptable carrier, pg. 11, last para.).
Claims 1-2 and 12-13, are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Sumarno (AIP Conf. Proc., 2017, cited on PTO-892).
Regarding claims 1-2 and 12-13: Sumarno teaches ketoprofen is poorly soluble drug of which solubility can be enhanced by form complexation with B-cyclodextrin (abstract). Sumarno teaches the preparation of a ketoprofen complex comprising adding supercritical carbon dioxide to a physical mixture of ketoprofen and B-cyclodextrin in water at a temperature of 50 degrees C at pressure of 150-200 bar through 2 hours (pg. 080010-2, para. 3). Wherein the complex has increased solubility, it consequently has higher bioavailability when compared to ketoprofen alone, absent evidence to the contrary.
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Antle (US 2020/0157252, IDS filed February 16, 2024).
Regarding claim 1: Antle teaches a process and equipment assembly for reacting a substituent precursor with a cyclodextrin starting material to provide a raw product comprising a cyclodextrin derivative and 1 % or less of an initial amount of the substituent precursor is provided (abstract). The starting material can be B-cyclodextrin (pg. 9, para. 0112). A substituent precursor refers to a compound, reagent, moiety, or substance capably of reacting with an -OH group present on a cyclodextrin (i.e. an agent, pg. 5, para. 0072). Process parameters can be altered as needed either dependently or independently to provide a cyclodextrin derivative possessing the desired properties , such as a target degree of substitution or primary regioisomeric substitution pattern (pg. 9, para. 0114). In example 1, Antle teaches a method of preparing a modified cyclodextrin comprising, Portions of the alkaline cyclodextrin-containing aqueous milieu were contacted in-line with portions of substituent precursor to form a flowing feedstock in a conduit, wherein the molar ratio of substituent precursor to cyclodextrin starting material was in the range of about 1:1 to about 15:1; Portions of the flowing feedstock were conducted (pumped) through a flow-through reactor having an internal reactor temperature within the range of about 40° C. to about 200° C for a residence time ranging from about 0.5 sec to about 2 hours and at a pressure of about 10 psi to about 200 psi to form a raw product comprising a derivatized cyclodextrin in an aqueous liquid medium (pg. 24, para. 0258).
Claim Rejections - 35 USC § 103
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.
Claims 1, 9-14, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Antle (US 2020/0157252, IDS filed February 16, 2024).
Regarding claims 1 and 9-13: Even if assuming for the sake of argument that Antle does not teach an “agent” as instantly claimed, claim 1, as well as claims 9-14 and 16 would have been obvious over Antle. Antle teaches a process and equipment assembly for reacting a substituent precursor with a cyclodextrin starting material to provide a raw product comprising a cyclodextrin derivative and 1 % or less of an initial amount of the substituent precursor is provided (abstract). The starting material can be B-cyclodextrin (pg. 9, para. 0112). A substituent precursor refers to a compound, reagent, moiety, or substance capably of reacting with an -OH group present on a cyclodextrin (i.e. an agent, pg. 5, para. 0072). Process parameters can be altered as needed either dependently or independently to provide a cyclodextrin derivative possessing the desired properties , such as a target degree of substitution or primary regioisomeric substitution pattern (pg. 9, para. 0114). In example 1, Antle teaches a method of preparing a modified cyclodextrin comprising, Portions of the alkaline cyclodextrin-containing aqueous milieu were contacted in-line with portions of substituent precursor to form a flowing feedstock in a conduit, wherein the molar ratio of substituent precursor to cyclodextrin starting material was in the range of about 1:1 to about 15:1; Portions of the flowing feedstock were conducted (pumped) through a flow-through reactor having an internal reactor temperature within the range of about 40° C. to about 200° C for a residence time ranging from about 0.5 sec to about 2 hours and at a pressure of about 10 psi to about 200 psi to form a raw product comprising a derivatized cyclodextrin in an aqueous liquid medium (pg. 24, para. 0258). The liquid medium can be water (pgs. 7-8, para. 0103). Although Antle does not specify the exact conditions (temperature range from 20 to about 300 C, 15 PSI to about 200 PSI, time in a range of 0.1 hours to about 1 hour, or cyclodextrin:agent molar ratio) as recited by instant claims 9-11, In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists (See MPEP 2144.05 (I)). Thus, the method of claims 1 and 9-13 are encompassed by Antle.
Regarding claims 14 and 16: Antle further teaches in some embodiments, a composition further comprises a pharmaceutically acceptable excipient (pg. 19, para. 0218). Antle teaches the excipient can be a carrier (pg. 20, para. 0219). Antle further teaches the cyclodextrin derivative can be combined with active agents having biological activity (pg. 19, para. 0217). Antle further teaches the active agent can be present in an effective amount when administered to a subject (i.e. a method of administering, pg. 19, para. 0214).
Claims 16 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Franco (Polymers, 2021, IDS filed February 16, 2024) as applied to claims 1-4, 8, 11-12, 14 above.
Regarding claim 16: As discussed above, Franco teaches the pharmaceutical composition of claim 14. Franco does not explicitly teach a method of administering the composition for the treatment of diabetes in a patient.
However, Franco teaches rutin is a flavonoid that is known in the art to possess antioxidant, anti-inflammatory, antiviral, antidiabetic, and anticancer activities (pg. 1, para. 1).
Taken together it would have been prima facie obvious to administer the composition of Franco to a subject with diabetes as is suggested by Franco. A person of ordinary skill in the art would have had the motivation to do so with reasonable expectation of success in order to treat the diabetic subject as rutin is known in the art to have antidiabetic properties.
Claims 7 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Franco (Polymers, 2021, IDS filed February 16, 2024) as applied to claims 1-4, 8, 11-12, 14, 16, 20 above in view of Krishna (Can. J. Physiol. Pharmacol., 2005, cited on PTO-892).
Regarding claim 7: As discussed above, Franco teaches the method of claim 3. Franco does not teach wherein the cyclodextrin-modified agent is BCD-quercetin.
However, Krishna teaches β-cyclodextrin complexes with quercetin and rutin are known therapeutics in diabetic rat models (abstract, pg. 345, col. 1, para. 1).
Taken together it would have been prima facie obvious to modify the method of Franco such that rutin is replaced with quercetin as taught by Krishna. A person of ordinary skill in the art would have had the motivation to do so with reasonable expectation of success as both rutin and quercetin are capable of forming complexes with cyclodextrins for treating diabetes, and it is prima facie obvious to substitute equivalents known for the same purpose.
Regarding claim 15: As discussed above, Franco teaches the method of claim 3. Franco does not teach wherein the composition is formulated for oral administration.
However, Krishna teaches cyclodextrin complexes with quercetin and rutin are known therapeutics in diabetic rat models (abstract, pg. 345, col. 1, para. 1). Krishna teaches oral administration of said complexes (pg. 345, col. 1, para. 2).
Taken together it would have been prima facie obvious to administer the composition of Franco to a subject orally as suggested by Krishna. A person of ordinary skill in the art would have had the motivation to do so with reasonable expectation of success as this is a known route of administration in the art of administering rutin-cyclodextrin complexes.
Claims 5-6 are rejected under 35 U.S.C. 103 as being unpatentable over Franco (Polymers, 2021, IDS filed February 16, 2024) and Krishna (Can. J. Physiol. Pharmacol., 2005, cited on PTO-892) as applied to claims 1-4, 7-8, 11-12, 14-16, and 20 above in view of Chidambaram (Advanced Pharmaceutical Bulletin, 2014, cited on PTO-892) and Arya (J. Molecular Structure, 2021, cited on PTO-892).
Regarding claims 5-6: As discussed above, Franco teaches the method of claim 3. Franco and Krishna render obvious a method wherein quercetin is used in place of rutin.
They do not teach wherein the agent comprises quercetin and curcumin.
However, Chidambaram teaches curcumin a hydrophobic phenol that has medicinal benefits with diabetes (pg. 1, col. 1, para. 1). Chidambaram teaches curcumin and quercetin are compatible with each other and compatible with B-cyclodextrin (abstract, pg. 2, table 1). Arya teaches curcumin is known to complex with B-cyclodextrin for enhancing solubility (abstract).
Taken together it would have been prima facie obvious to modify the method of Franco and Krishna such that the agent comprises quercetin and curcumin as suggested by Chidambaram and Arya. A person of ordinary skill in the art would have had the motivation to do so with reasonable expectation of success as these compounds are compatible with each other and B-cyclodextrin, and curcumin is known to be complexed with B-cyclodextrin to enhance aqueous solubility, and has medicinal benefits with diabetes.
Claims 15 and 17-18 are rejected under 35 U.S.C. 103 as being unpatentable over Franco (Polymers, 2021, IDS filed February 16, 2024) as applied to claims 1-4, 8, 11-12, 14, 16, and 20 above in view of Lahey (US2004/0102386, cited on PTO-892).
Regarding claims 15 and 17-18: As discussed above, Franco teaches the method of claim 14 and 16. Franco teaches rutin is a flavonoid that is known in the art to possess antioxidant, anti-inflammatory, antiviral, antidiabetic, and anticancer activities (pg. 1, para. 1).
Franco does not teach wherein the composition is formulated for sublingual administration for the treatment of a viral infection.
However, Lahey teaches administration of a composition comprising rutin sublingually to treat type I diabetes (pg. 10, para. 0097). Lahey teaches in another embodiment that sublingual absorption is rapid (pg. 10, para. 0099).
Taken together it would have been prima facie obvious to administer the composition for the treatment of viral diseases of Franco to a subject sublingually as suggested by Lahey. A person of ordinary skill in the art would have had the motivation to do so with reasonable expectation of success as this is a known route of administration in the art of administering rutin containing compositions in order to impart rapid absorption to alleviate symptoms faster.
Claims 15 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Franco (Polymers, 2021, IDS filed February 16, 2024) as applied to claims 1-4, 8, 11-12, 14, 16, and 20 above in view of Ganeshpurkar (Saudi Pharmaceutical J, 2017, cited on PTO-892).
Regarding claims 15 and 21: As discussed above, Franco teaches the method of claim 16. Franco teaches rutin is a flavonoid that is known in the art to possess antioxidant, anti-inflammatory, antiviral, antidiabetic, and anticancer activities (pg. 1, para. 1). Franco teaches rutin is widely spread in cosmetics due to its action against hair follicles, and has benefits to the skin for the promotion of collagen synthesis, the sunscreen effect, and anti-fatigue activity (pg. 1, para. 1).
Franco does not teach wherein the composition is formulated for topical administration for the treatment at least one skin condition.
However, Ganeshpurkar teaches rutin is topically applied for the treatment of atopic dermatitis (pg. 156, col. 1, para. 2).
Taken together it would have been prima facie obvious to administer the composition of Franco to a subject topically for the treatment of atopic dermatitis as suggested by Ganeshpurkar. A person of ordinary skill in the art would have had the motivation to do so with reasonable expectation of success as this is a known route of administration in the art of administering rutin and rutin is known therapeutic for the skin condition atopic dermatitis.
Conclusion
No claims are allowed in this action.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure:
Li (CN 106606785, cited on PTO-892). The English language translation relied upon has been provided by the Examiner. Li teaches the preparation of a baicalin-hydroxypropyl-beta-cyclodextrin inclusion compound (English translation, abstract).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SAMUEL L GALSTER whose telephone number is (571)270-0933. The examiner can normally be reached Monday - Friday 8:00 AM - 5:00 PM.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Y 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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/SAMUEL L GALSTER/Examiner, Art Unit 1693
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