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
Applicant’s preliminary amendment of 14 March 2025, in which claims 1-70 have been cancelled, and new claims 71-84 have been added, is acknowledged.
Claims 71-84 are pending in the instant application.
Claims 71-84 are examined herein.
Priority
This application is a Continuation of U.S. Patent Application 18/095,498, filed on 10 January 2023, now abandoned, which claims the benefit of U.S. Provisional Patent Application Number 63/298,192, filed on 10 January 2022.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 24 December 2024 is acknowledged and considered.
Objection to the Specification
The Specification is objected due to a minor typographical error on page 3, [0006], the text “1-palmitoy-2-loleoyl” should read 1-palmitoyl-2-oleyl.
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 73 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 pre-AIA the applicant regards as the invention.
Claim 73 is drawn to a pharmaceutical composition of claim 71, wherein at least 51% of the dextro rotatory isomer is at the sn-2 position of the terminal glycerol moiety.
Yet, claim 71 is drawn to a pharmaceutical composition consisting of
at least 80% of 1- palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1’-rac-glycerol)
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(alternative name POPG), where the glycerol moiety in the phosphatidylglycerol is racemic.
As such, there is insufficient antecedent basis for the limitation “at least 51% of the dextro rotatory isomer at the sn-2 position of the terminal glycerol moiety” of claim 73, in claim 71.
Appropriate clarification of the claim language is required.
Claims 82, 83 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 pre-AIA the applicant regards as the invention.
Claim 82 depends on claim 71, and recites that the composition contains 49.0 - 51.0 mol % palmitic acid; yet claim 71 recites no more than 1% of palmitic acid in the composition. As such, there is insufficient antecedent basis for the limitation “the composition contains 49.0 - 51.0 mol % palmitic acid” of claim 82, in claim 71.
Similarly, claim 83 depends on claim 71, and recites that the composition contains 49.0 - 51.0 mol % oleic acid; yet claim 71 recites no more than 1% of oleic acid in the composition. As such, there is insufficient antecedent basis for the limitation “the composition contains 49.0 - 51.0 mol % oleic acid” of claim 83, in claim 71.
Appropriate clarification of the claim language is required.
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 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 71-72, 74-81 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Numata et al. (PNAS 2010, 107 (1), 320-325, cited in IDS).
Numata (PNAS 2010, 107 (1), 320-325) teaches a pharmaceutical composition comprising POPG (page 320, last paragraph)
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as a liposome (page 324, left column, third paragraph).
Numata is silent regarding the presence of 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) in the composition, which satisfies the limitation no more than 20% of 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) in instant claim 71.
Numata is silent regarding the presence of 1,2-dihexadecanoyl-sn-glycero-3-phospho- (1'racglycerol) in the composition, which satisfies the limitation in instant claims 71, 75.
Numata is silent regarding the presence of 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3- phospho-(1'racglycerol) in the composition, which satisfies the limitation in instant claims 71, 76.
Numata is silent regarding the presence of 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine (P-Lyso-PC) in the composition, which satisfies the limitation in instant claims 71, 77.
Numata is silent regarding the presence of 1-oleoyl-2-hydroxy-sn-glycero-3-phospho-(1'-rac- glycerol) in the composition, which satisfies the limitation in instant claims 71, 78.
Numata is silent regarding the presence of 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC) in the composition, which satisfies the limitation in instant claims 71, 79.
Numata is silent regarding the presence of free fatty acids in the composition, as in instant claim 80, and is silent regarding impurities, as in instant claim 81.
The compound POPG is racemic (1:1 sn-1’ and sn-3’) with respect to the po-lar end glycerol moiety.
With respect to claim 72, 74, it is pointed that the ability to antagonize toll-like receptors 1, 2, 3, 6, 7, 8, 10, and optical rotation are properties of the compound/composition and are inseparable from the compound/composition. Therefore, if the prior art teaches the compound composition or renders the compound/composition obvious, then the properties are also taught or rendered obvious by the prior art. In re Spada, 911 F.2d 705, 709, 15 USPQ 1655, 1658 (Fed. Cir. 1990.) See MPEP 2112.01. The burden is shifted to Applicant to show that the prior art product does not possess or render obvious the same properties as the instantly claimed product.
As such, claims 71-72, 74-81 are anticipated by Numata.
Claims 71-72, 74-81 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Naoya et al. (JP 2000281688, published 10 October 2000, cited in IDS).
Naoya et al. (JP 2000281688) teaches [0014] a composition containing 99.5 wt% of purified 1-palmitoyl-2-oleoyl-3-phosphatidylglycerol (2 chiral centers, 2 pairs of diastereoisomers) ammonium salts, 0.1 wt % of 1-palmitoyl-2-oleoyl-3-phosphatidylcholine, 0.2 wt % of lyso forms, and 0.2 wt % of free fatty acids.
The composition does not contain 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) (because the first step in the synthesis is an enzymatic (Lecitase) hydrolysis of dipalmitoylphosphatidylcholine to give monopalmitoylphosphatidylcholine, which is then esterified with oleic anhydride to give 1-palmitoyl-2-oleoyl-3-phosphatidylcholine), which satisfies the limitation no more than 20% of 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) in instant claim 71.
Naoya is silent regarding the presence of 1,2-dihexadecanoyl-sn-glycero-3-phospho- (1'racglycerol) in the composition, which satisfies the limitation in instant claims 71, 75.
Naoya is silent regarding the presence of 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3- phospho-(1'racglycerol) in the composition, which satisfies the limitation in instant claims 71, 76.
Naoya teaches 0.2 wt % of lyso forms, which contain 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine (P-Lyso-PC), as in instant claims 71, 77.
Naoya does not teach 1-oleoyl-2-hydroxy-sn-glycero-3-phospho-(1'-rac- glycerol) in the composition, which satisfies the limitation in instant claims 71, 78.
Naoya teaches 0.1 wt % of 1-palmitoyl-2-oleoyl-3-phosphatidylcholine (alternative name 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC)) in the composition, which satisfies the limitation in instant claims 71, 79.
Naoya teaches 0.2 wt % of free fatty acids in the composition, as in instant claim 80.
Naoya teaches that the composition contains 99.5 wt% of purified 1-palmitoyl-2-oleoyl-3-phosphatidylglycerol, thus the amount of impurities is 0.5% wt., which satisfies the limitation in instant claim 81.
The compound 1-palmitoyl-2-oleoyl-3-phosphatidylglycerol has two 2 chiral centers (2 pairs of diastereoisomers) and is racemic (1:1 sn-1’ and sn-3’) with respect to the po-lar end glycerol moiety.
With respect to claim 72, 74, it is pointed that the ability to antagonize toll-like receptors 1, 2, 3, 6, 7, 8, 10, and optical rotation are properties of the compound/composition and are inseparable from the compound/composition. Therefore, if the prior art teaches the compound composition or renders the compound/composition obvious, then the properties are also taught or rendered obvious by the prior art. In re Spada, 911 F.2d 705, 709, 15 USPQ 1655, 1658 (Fed. Cir. 1990.) See MPEP 2112.01. The burden is shifted to Applicant to show that the prior art product does not possess or render obvious the same properties as the instantly claimed product.
As such, a composition of instant claims 71-72, 74-81 is anticipated by Naoya.
Claims 71-81 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Virtanen et al. (EP 0319136, published 7 June 1989, cited in IDS).
This rejection interprets claim 71 as being drawn to a composition which contains enantiomerically enriched 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidyl-sn-1’-glycerol (at least 51% dextrorotatory isomer, as in claim 73).
Virtanen teaches a pharmaceutical composition which is a liposome comprising 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidyl-sn-1’-glycerol (column 6, lines 19-20).
Virtanen teaches that 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidyl-sn-1’-glycerol (1’-POPG) (column 4, lines 37-38) is commercially available from KSV-Chemicals Oy, Helsinki, Finland (column 4, lines 39-42).
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidyl-sn-1’-glycerol (stereochemistry shown below)
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, satisfies the limitation in claim 73 enantiomeric enrichment with at least 51% of the dextro rotatory isomer at the sn-2 position of the terminal glycerol moiety.
Virtanen teaches (column 2, lines 28-40) that phosphatidyl glycerol commonly used for the preparation of liposomes has, besides at the sn-2--carbon atom of the glycerol structure, also an L, D-configuration in the polar end glycerol moiety. Virtanen teaches that phosphatidyl glycerol is conventionally prepared from lecithin by so called trans-phosphatidylation using phospholipase D-enzyme; as a result of the trans-phospatidylation reaction, a product is formed which is racemic with respect to the po-lar end glycerol moiety: the phosphatidyl glycerol mixture obtained for use in the preparation of liposomes namely contains both the 1′- and the 3′-form.
Virtanen teaches (column 2, last paragraph) that the 1′- and 3′-isomers differ from each other substantially in their physicochemical proper-ties. A liposome made from the 3′-isomer binds, due to its stereochemical structure, Na⁺-ions to its surface much mo-re tightly than the 1′-isomer, thus neutralizing the nega-tive charge on the liposome surface. As a consequence of this a liposomal dispersion containing the 3′-isomer is substantially more crystalline in the presence of Na⁺-ions than a corresponding dispersion made from the 1′-isomer, thus leading to the formation of undesirable agglomeration and the fusion of liposomes in a dispersion. It has thus been shown that a liposome dis-persion made from the 3′-isomer of a typical phosphatidyl glycerol has a storage stability of only a few days, that of a 1:1-mixture of the 1′- and 3′-isomer of a few weeks, and finally that of the plain 1′-isomer of several months (column 3, first paragraph).
Virtanen teaches (column 3, line 24) that only the 1’-isomer exists in nature.
Virtanen teaches (column 3, lines 27-33) that even if the liposomes were to contain a mixtu-re, in which the phosphatidyl glycerol was formed to a ma-jor part by the 1′-isomer, and only to a minor part by the 3′-isomer, which is consistent with the limitation in claim 73 enantiomeric enrichment with at least 51% of the dextro rotatory isomer at the sn-2 position of the terminal glycerol moiety, the 3′-isomer, due to its slower metabolism, might accumulate in the organism, which may prove detrimental.
Virtanen teaches (column 3, lines 34-42) that the invention concerns a liposo-me, the wall material of which consists of a specific iso-mer of phosphatidyl glycerol, namely the sn-3--phosphatidyl-sn-1′-glycerol isomer, and a process for the preparation of the novel liposome, which process is characterized in that an sn-3-phosphatidyl-sn-1′-glycerol-isomer is dispersed in an aqueous medium, and liposomes thus formed are collected.
Virtanen is silent regarding the presence of 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) in the composition, which satisfies the limitation no more than 20% of 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) in instant claim 71.
Virtanen is silent regarding the presence of 1,2-dihexadecanoyl-sn-glycero-3-phospho- (1'racglycerol) in the composition, which satisfies the limitation in instant claim 71.
Virtanen is silent regarding the presence of 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3- phospho-(1'racglycerol) in the composition, which satisfies the limitation in instant claims 71, 76.
Virtanen is silent regarding the presence of 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine (P-Lyso-PC) in the composition, which satisfies the limitation in instant claims 71, 77.
Virtanen is silent regarding the presence of 1-oleoyl-2-hydroxy-sn-glycero-3-phospho-(1'-rac- glycerol) in the composition, which satisfies the limitation in instant claims 71, 78.
Virtanen is silent regarding the presence of 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC) in the composition, which satisfies the limitation in instant claims 71, 79.
Virtanen is silent regarding the presence of free fatty acids in the composition, as in instant claim 80, and is silent regarding impurities, as in instant claim 81.
With respect to claim 72, 74, it is pointed that the ability to antagonize toll-like receptors 1, 2, 3, 6, 7, 8, 10, and optical rotation are properties of the compound/composition and are inseparable from the compound/composition. Therefore, if the prior art teaches the compound composition or renders the compound/composition obvious, then the properties are also taught or rendered obvious by the prior art. In re Spada, 911 F.2d 705, 709, 15 USPQ 1655, 1658 (Fed. Cir. 1990.) See MPEP 2112.01. The burden is shifted to Applicant to show that the prior art product does not possess or render obvious the same properties as the instantly claimed product.
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.
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.
Claim 73, 84 are rejected under 35 U.S.C. 103 as obvious over Numata et al. (PNAS 2010, 107 (1), 320-325, cited in IDS), as applied to claim 71 above, in view of Itabashi (J. Lipid Nutr. 2012, 21 (1), 27-34, cited in IDS).
Numata (PNAS 2010, 107 (1), 320-325) teaches a pharmaceutical composition comprising POPG (page 320, last paragraph)
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as a liposome (page 324, left column, third paragraph).
Numata is silent regarding the presence of 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) in the composition, which satisfies the limitation no more than 20% of 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) in instant claim 71.
Numata is silent regarding the presence of 1,2-dihexadecanoyl-sn-glycero-3-phospho- (1'racglycerol) in the composition, which satisfies the limitation in instant claims 71, 75.
Numata is silent regarding the presence of 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3- phospho-(1'racglycerol) in the composition, which satisfies the limitation in instant claims 71, 76.
Numata is silent regarding the presence of 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine (P-Lyso-PC) in the composition, which satisfies the limitation in instant claims 71, 77.
Numata is silent regarding the presence of 1-oleoyl-2-hydroxy-sn-glycero-3-phospho-(1'-rac- glycerol) in the composition, which satisfies the limitation in instant claims 71, 78.
Numata is silent regarding the presence of 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC) in the composition, which satisfies the limitation in instant claims 71, 79.
Numata is silent regarding the presence of free fatty acids in the composition, as in instant claim 80, and is silent regarding impurities, as in instant claim 81.
The compound POPG is racemic (1:1 sn-1’ and sn-3’) with respect to the po-lar end glycerol moiety.
Numata does not teach that POPG is enantiomerically enriched with at least 51% of the dextro rotatory isomer at the sn-2 position of the terminal glycerol moiety, as in instant claim 73.
Itabashi (J. Lipid Nutr. 2012, 21 (1), 27-34) teaches chiral HPLC separation of 1,2-diacyl-sn-glycero-3-phospho-1’-sn-glycerol (Fig. 1 (J), also Fig. 2 (D) HPLC separation of 1,2-diacyl-sn-glycero-3-phospho-1’-sn-glycerol (R,S) and its diastereomer (R,R)).
It would have been obvious to combine the teachings of Numata and Itabashi to arrive at the instant invention.
The person of ordinary skill in the art would have separated the two diasteroisomers of POPG, namely natural 1-palmitoyl-2-oleyl-sn-glycero-3-phospho-1’-sn-glycerol (R,S, configuration L,D) and its diastereomer 1-palmitoyl-2-oleyl-sn-glycero-3-phospho-3’-sn-glycerol (R,R, configuration L, L), using the HPLC chiral chromatographic method taught by Itabashi, with the expectation that such chromatographic chiral separation results in pure 1-palmitoyl-2-oleyl-sn-glycero-3-phospho-1’-sn-glycerol, or in a diastereoisomeric mixture enriched in 1-palmitoyl-2-oleyl-sn-glycero-3-phospho-1’-sn-glycerol.
Regarding claim 84, it would have been obvious to formulated said liposome as powder for oral inhalation, because Numata teaches that said compound POPG is effective to treat respiratory virus infections.
As such, claims 73, 84 are rejected as prima facie obvious.
Claim 73 is rejected under 35 U.S.C. 103 as obvious over Naoya et al. (JP 2000281688, published 10 October 2000, cited in IDS), as applied to claim 71 above, in view of Itabashi (J. Lipid Nutr. 2012, 21 (1), 27-34, cited in IDS).
Naoya et al. (JP 2000281688) teaches [0014] a composition containing 99.5 wt% of purified 1-palmitoyl-2-oleoyl-3-phosphatidylglycerol (2 chiral centers, 2 pairs of diastereoisomers) ammonium salts, 0.1 wt % of 1-palmitoyl-2-oleoyl-3-phosphatidylcholine, 0.2 wt % of lyso forms, and 0.2 wt % of free fatty acids.
The composition does not contain 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) (because the first step in the synthesis is an enzymatic (Lecitase) hydrolysis of dipalmitoylphosphatidylcholine to give monopalmitoylphosphatidylcholine, which is then esterified with oleic anhydride to give 1-palmitoyl-2-oleoyl-3-phosphatidylcholine), which satisfies the limitation no more than 20% of 1-oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-rac-glycerol) in instant claim 71.
Naoya is silent regarding the presence of 1,2-dihexadecanoyl-sn-glycero-3-phospho- (1'racglycerol) in the composition, which satisfies the limitation in instant claims 71, 75.
Naoya is silent regarding the presence of 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3- phospho-(1'racglycerol) in the composition, which satisfies the limitation in instant claims 71, 76.
Naoya teaches 0.2 wt % of lyso forms, which contain 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine (P-Lyso-PC), as in instant claims 71, 77.
Naoya does not teach 1-oleoyl-2-hydroxy-sn-glycero-3-phospho-(1'-rac- glycerol) in the composition, which satisfies the limitation in instant claims 71, 78.
Naoya teaches 0.1 wt % of 1-palmitoyl-2-oleoyl-3-phosphatidylcholine (alternative name 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC)) in the composition, which satisfies the limitation in instant claims 71, 79.
Naoya teaches 0.2 wt % of free fatty acids in the composition, as in instant claim 80.
Naoya teaches that the composition contains 99.5 wt% of purified 1-palmitoyl-2-oleoyl-3-phosphatidylglycerol, thus the amount of impurities is 0.5% wt., which satisfies the limitation in instant claim 81.
The compound 1-palmitoyl-2-oleoyl-3-phosphatidylglycerol has two 2 chiral centers (2 pairs of diastereoisomers) and is racemic (1:1 sn-1’ and sn-3’) with respect to the po-lar end glycerol moiety.
Naoya does not teach does not teach 1-palmitoyl -2-oleyl -sn-3-phosphatidylglycerol enantiomerically enriched with at least 51% of the dextro rotatory isomer at the sn-2 position of the terminal glycerol moiety, as in instant claim 73.
Itabashi (J. Lipid Nutr. 2012, 21 (1), 27-34) teaches chiral HPLC separation of 1,2-diacyl-sn-glycero-3-phospho-1’-sn-glycerol (Fig. 1 (J), also Fig. 2 (D) HPLC separation of 1,2-diacyl-sn-glycero-3-phospho-1’-sn-glycerol (R,S) and its diastereomer (R,R)).
It would have been obvious to combine the teachings of Naoya and Itabashi to arrive at the instant invention.
The person of ordinary skill in the art would have separated the four enantiomers of 1-palmitoyl-2-oleoyl-3-phosphatidylglycerol using the HPLC chiral chromatographic method taught by Itabashi, with the expectation that such chromatographic chiral separation results in pure 1-palmitoyl-2-oleyl-sn-glycero-3-phospho-1’-sn-glycerol (natural, (R,S), configuration L,D).
As such, claim 73 is rejected as prima facie obvious.
Conclusion
Claims 71-84 are rejected.
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/IRINA NEAGU/Primary Examiner, Art Unit 1629
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