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
2. Claims 1 – 10 are pending in this application. Applicant’s preliminary amendment, submitted August 5, 2024, is entered, wherein claims 7 – 8 and 10 are amended and claim 11 is canceled.
Claims 1 – 10 are examined on the merits herein.
Priority
3. This application is a national stage application of PCT/IB2022/050566, filed January 22, 2022, which claims benefit of foreign priority document IN202121003052, filed January 22, 2021.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 07/21/2023 was filed in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Objections
Claims 1 – 2 and 5 – 6 are objected to because of the following informalities:
Claim 1, line 7, “-(CH2)3NH2” should read “-(CH2)3NH2”.
Claims 1 – 2, lines 7 – 8, “S03” should read “SO3”.
Claims 1 – 2, line 9, “NHCOCH3” should read “NHCOCH3”.
Claims 1 – 2 and 5 – 6, lines 9 and 4, respectively, “SO3” should read “SO3”.
Claim 1, line 9, “PO42-“ should read “PO42-“.
Claims 5 – 6, line 6, “OSO3” should read “OSO3”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 7 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 7 depends from claim 1, which claim 7 does not further limit the subject matter of the claim. Claim 1 requires R1 to be –(CH2)3NH2, corresponding to a 3-aminopropyl substituent. However, claim 7 recites species having an “ethoxy-2-aminoethyoxyl”, corresponding to the R1 substituent recited in claims 3 – 4. These species do not include the R1 substituent required by claim 1 and therefore are not species within the scope of claim 1. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements. Claim 7 is given its broadest reasonable interpretation. Therefore, claim 7 is interpreted as encompassing the specifically recited compounds in the claim, including the compounds corresponding to the subject matter of claim 3 having the ethyoxy-2-aminoethyoxy substituent.
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.
Claims 1 – 2 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Tiruchinapally et al. (Chemistry – a European Journal, 2011, Vol. 17, Issue 36, page 10106 – 10112, Reference included with PTO-892).
a. Tiruchinapally et al. teach compound 39 (page 10110):
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Tiruchinapally et al. teach compound 39, which corresponds to the claimed compound recited in claims 1 – 2, wherein R1 is –(CH2)3NH2; R4 and R4a are H; R5 is NHCOCH3; R6 at the second sugar ring is H; and R6 at the fourth sugar ring is SO3.
For these reasons, Tiruchinapally et al. anticipates claims 1 – 2.
Claims 3 – 4 and 7 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shanthamurthy et al. (European Journal of Organic Chemistry, 2019, Vol. 2019, Issue 18, page 2950 – 2953, Reference included with PTO-892) as evidenced by Sano et al. (Chemistry – an Asian Journal, 2019, Vol. 14, Issue 11, page 1965 – 1969, Reference included with PTO-892).
b. Shanthamurthy et al. teach compounds I-1, I-2, and I-3 (page 2952, Scheme 4):
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wherein R is
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and n is 0, 1, and 2, respectively. Shanthamurthy et al. teach that these compounds have undergone global deprotection to yield oligo-iduronic acids (page 2953, Left Col., para. 1), wherein the global deprotection is performed in Pd(OH)2 in MeOH. As evidenced by Sano et al., Pd(OH)2 in alcohol will convert azide to amine (page 1967, Scheme 1):
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Therefore,
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will yield
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after global deprotection.
Shanthamurthy et al. teach compound I-2, which corresponds to the claimed compound, namely ethoxy-2-aminoethyoxy-O-(α-L-idopyranosyl Uronic Acid- α(1[Wingdings font/0xE0]4))- α-L-idopyranosyl Uronic Acid, recited in claims 3 – 4 and 7, wherein R1 is
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; R2 is COOH; R3 and R4 are H; R5 is OH; and n is 1.
For these reasons, Shanthamurthy et al. anticipates the claimed invention.
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 (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 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:
i. Determining the scope and contents of the prior art.
ii. Ascertaining the differences between the prior art and the claims at issue.
iii. Resolving the level of ordinary skill in the pertinent art.
iv. Considering objective evidence present in the application indicating obviousness or
nonobviousness.
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.
Claims 3 and 5 are rejected under 35 U.S.C. 103 as being unpatentable over Shanthamurthy et al. (European Journal of Organic Chemistry, 2019, Vol. 2019, Issue 18, page 2950 – 2953, Reference included with PTO-892) as evidenced by Sano et al. (Chemistry – an Asian Journal, 2019, Vol. 14, Issue 11, page 1965 – 1969, Reference included with PTO-892) in view of Hammond et al. (FEBS Open Bio, 2013, Vol. 3, Issue 1, page 346 – 351, Reference included with PTO-892) and Tiruchinapally et al. (Chemistry – a European Journal, 2011, Vol. 17, Issue 36, page 10106 – 10112, Reference included with PTO-892).
c. Shanthamurthy et al. teach that L-iduronic acid (IdoA) plays a pivotal role in glycosaminoglycan (GAG) protein interactions, and that oligo-iduronic acid (Oligo-IdoA) are ideal and straightforward heparin mimetics useful for correlating IdoA structure and function and fine-tuning carbohydrate -protein interactions (Abstract). Shanthamurthy et al. teach three oligo-IdoA compounds I-1, I-2, and I-3 (page 2952, Scheme 4):
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,
wherein R is
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and n is 0, 1, and 2, respectively. Shanthamurthy et al. teach that these compounds have undergone global deprotection to yield oligo-iduronic acids (page 2953, Left Col., para. 1), wherein the global deprotection is performed in Pd(OH)2 in MeOH. According to Sano et al., Pd(OH)2 in alcohol will convert azide to amine (page 1967, Scheme 1):
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Therefore,
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will yield
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after global deprotection. Shanthamurthy et al. teach compounds I-2 and I-3, which corresponds to the claimed compound, namely ethoxy-2-aminoethyoxy-O-(α-L-idopyranosyl Uronic Acid- α(1[Wingdings font/0xE0]4))- α-L-idopyranosyl Uronic Acid, recited in claims 3 – 4 and 7, wherein R1 is
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; R2 is COOH; R3 and R4 are H; R5 is OH; and n is 1 or 2.
However, Shanthamurthy et al. do not teach the heparin sulfate with R1 = cholestenol, R3 = SO3; and R5 = OSO3.
Hammond et al. disclose the structure of PG545 (page 347, Fig. 1):
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PG545 is a tetrasaccharide heparan sulfate (HS) mimetic, which exhibits inhibitory activity toward HS-degrading enzyme heparanase, and is a clinical anti-cancer candidate. Hammond et al. explicitly state that the cholestanol aglycon of PG545 significantly increases the affinity for heparanase and also modifies the inhibition mode (Abstract).
Tiruchinapally et al. teach that biological functions can be critically dependent on sulfation patterns and backbone sequences (page 10106, Left Col., para. 1).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to substitute
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as taught by Shanthamurthy et al. with the cholestanol aglycon at the R position of compound I-2 or I-3 in view of Hammond et al. because Shanthamurthy et al. teach that IdoA plays a pivotal role in GAG-protein interactions and that oligo-IdoA are heparin mimetics useful for correlating IdoA structure and function and fine-tuning carbohydrate-protein interactions and Hammond et al. teach that the cholestanol aglycon significantly increases the affinity for heparanase and modifies the inhibition mode. Thus, Shanthamurthy et al. provide an oligo-IdoA heparin-mimetic scaffold relevant to GAG/protein binding and Hammond et al. provide the heparanase-specific motivation by teaching that PG545 is a sulfated tetrasaccharide heparin sulfate mimetic that inhibits the HS-degrading enzyme heparanase, and that the cholestanol aglycon significantly increases affinity for heparanase and modifies the inhibition mode. Because heparanase is an HS/GAG-interacting enzyme and Hammond et al. teach that a cholestanol aglycon improves heparanase affinity of sulfated oligosaccharides HS mimetics, one of ordinary skill in the art would have been motivated to substitute
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as taught by Shanthamurthy et al. with the cholestanol aglycon at the R position of compound I-2 or I-3 in view of Hammond et al. to obtain a heparan sulfate mimetic expected to interact with or inhibit heparanase. Therefore, one of ordinary skill in the art would have had a reasonable expectation of success to substitute
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as taught by Shanthamurthy et al. with the cholestanol aglycon at the R position of compound I-2 or I-3 in view of Hammond et al. because both Shanthamurthy et al. and Hammond et al. teach compounds with similar scaffold and it is known in the art that the incorporation of cholestanol aglycon will improve the properties of the compounds, Shanthamurthy et al. demonstrate that defined oligo-IdoA heparin-mimetic scaffolds may be prepared, and Hammond et al. demonstrate that sulfated oligosaccharide HS mimetics bearing a cholestanol aglycon bind or inhibit heparanase with increased affinity. Thus, applying the known heparanase-binding design feature of Hammond et al. to the oligo-IdoA heparin-mimetic scaffold of Shanthamurthy et al. would have been expected to provide a compound having heparanase-related HS-mimetic activity.
Regarding claim 5, the selection of substituents R3 and R5 represents sulfation of available hydroxyl positions on oligo-iduronic acid scaffold of Shanthamurthy et al. Tiruchinapally et al. recognize that heparin/heparan sulfate biological activity depends on sulfation pattern and backbone sequence. Therefore, a person of ordinary skill in the art would have been motivated to prepare sulfated analogs of the oligo-iduronic acid scaffold of Shanthamurthy et al. bearing a cholestanol aglycon, and to routinely optimize the sulfation pattern at available hydroxyl positions to improve heparanase/HS-mimetic activity. Selecting R3 = SO3 and R5 = OSO3, while leaving R4 = H represents selection of a sulfation pattern from a finite set of known sulfate or H options at available hydroxyl positions.
Claims 3 and 6 are rejected under 35 U.S.C. 103 as being unpatentable over Modhiran et al. (Antiviral Research, 2019, Vol. 168, page 121 – 127, Reference included with PTO-892) in view of Tiruchinapally et al. (Chemistry – a European Journal, 2011, Vol. 17, Issue 36, page 10106 – 10112, Reference included with PTO-892).
d. Modhiran et al. teach non-sulfated precursor, cholestanyl β-maltotetraoside as well as PG454, which is a fully sulfated tetrasaccharide with a cholestanol aglycon (page 122, Fig. 1):
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However, Modhiran et al. do not teach the heparin sulfate with R3 = SO3 and R5 = OSO3.
Tiruchinapally et al. teach that biological functions can be critically dependent on sulfation patterns and backbone sequences (page 10106, Left Col., para. 1).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to select substituents R3 = SO3 and R5 = OSO3, while leaving R4 = H because Modhiran et al. teach both a non-sulfated cholestanyl β-maltotetraoside precursor and PG545, a fully sulfated tetrasaccharide having a cholestanol aglycon. Thus, Modhiran et al. teach that the available hydroxyl positions of the cholestanol-containing tetrasaccharide scaffold may be present either as hydroxyl groups or as sulfate ester groups. Tiruchinapally et al. further teach that the biological functions of heparin/heparan sulfate are critically dependent on sulfation patterns and backbone sequences. Therefore, a person of ordinary skill in the art would have recognized the sulfation pattern at the available hydroxyl positions as a result effective variable and would have been motivated to modify compound 2 disclosed by Modhiran et al. to partially sulfated analogs. One would have performed routine experimentation to discover the best sulfation pattern for improving heparanase/HS-mimetic activity. Moreover, Selecting R3 = SO3 and R5 = OSO3, while leaving R4 = H represents selection of a sulfation pattern from a finite set of known sulfate or H options at available hydroxyl positions. One of ordinary skill in the art would have had a reasonable expectation of success to select substituents R3 = SO3 and R5 = OSO3, while leaving R4 = H because Modhiran et al. teach the same cholestenol-containing tetrasaccharide scaffold in both non-sulfated form and fully sulfated form, demonstrating that the available hydroxyl positions on the scaffold are amenable to sulfation and Tiruchinapally et al. each that heparin/heparan sulfate biological activity depends on sulfation pattern and backbone sequence.
Claims 8 – 9 are rejected under 35 U.S.C. 103 as being unpatentable over Tiruchinapally et al. (Chemistry – a European Journal, 2011, Vol. 17, Issue 36, page 10106 – 10112, Reference included with PTO-892) in view of Ajani et al. (WO03/049721A1).
e. Tiruchinapally et al. teach compound 39 (page 10110):
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Tiruchinapally et al. teach compound 39, which corresponds to the claimed compound recited in claims 1, wherein R1 is –(CH2)3NH2; R4 and R4a are H; R5 is NHCOCH3; R6 at the second sugar ring is H; and R6 at the fourth sugar ring is SO3. Tiruchinapally et al. further teach that heparin and heparan sulfates play important roles in many biological events, such as pathogen infection, blood coagulation, and tumor metastasis. Their biological functions can be critically dependent on the sulfation patterns and backbone sequences. This has led to intense current interests in preparing heparin and heparan sulfate oligosaccharides with defined sulfation and backbone structures to decipher their structure-activity relationships (page 10106, Left Col., para. 1).
However, Tiruchinapally et al. do not teach a pharmaceutical composition comprising a compound of claim 1 and one or more pharmaceutically acceptable excipients, wherein the composition is in the form of tablets.
Ajani et al. teach pharmaceutical compositions for the oral administration of heparin or derivatives thereof (Title). Ajani et al. disclose that controlled-release formulations containing heparin or low molecular weight derivatives thereof have now been found to be administered through the oral route (page 2, line 28; page 3, lines 1 - 2). the controlled-release composition include excipients (page 3, line 17). Example of oral solid form is tablets (page 6, lines 22 - 23).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to formulate compound 39, a heparan sulfate derivative, as taught by Tiruchinapally et al. with one or more pharmaceutically acceptable excipients in view of Ajani et al. to obtain a pharmaceutical composition suitable for administration because Ajani et al. teach a pharmaceutical formulation of heparin or low molecular weight derivatives thereof. One would have been motivated to formulate compound 39, a heparan sulfate derivative, as taught by Tiruchinapally et al. with one or more pharmaceutically acceptable excipients in view of Ajani et al. to obtain a pharmaceutical composition suitable for administration because Ajani et al. teach that heparin and derivatives thereof may be formulated with excipients for oral administration and compound 39 is a structurally related derivatives of heparin. One of ordinary skill in the art would have had a reasonable expectation of success to formulate compound 39, a heparan sulfate derivative, as taught by Tiruchinapally et al. with one or more pharmaceutically acceptable excipients in view of Ajani et al. to obtain a pharmaceutical composition suitable for administration because Ajani et al. demonstrate that heparin derivatives may be formulated with excipients into oral pharmaceutical dosage forms.
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Tiruchinapally et al. (Chemistry – a European Journal, 2011, Vol. 17, Issue 36, page 10106 – 10112, Reference included with PTO-892) in view of Johnstone et al. (Journal of Medicinal Chemistry, 2010, Vol. 53, Issue 4, page 1686 – 1699, Reference included with PTO-892).
f. Tiruchinapally et al. teach compound 39 (page 10110):
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Tiruchinapally et al. teach compound 39, which corresponds to the claimed compound recited in claims 1 – 2, wherein R1 is –(CH2)3NH2; R4 and R4a are H; R5 is NHCOCH3; R6 at the second sugar ring is H; and R6 at the fourth sugar ring is SO3. Tiruchinapally et al. further teach that heparin and heparan sulfates play important roles in many biological events, such as pathogen infection, blood coagulation, and tumor metastasis. Their biological functions can be critically dependent on the sulfation patterns and backbone sequences. This has led to intense current interests in preparing heparin and heparan sulfate oligosaccharides with defined sulfation and backbone structures to decipher their structure-activity relationships (page 10106, Left Col., para. 1).
However, Tiruchinapally et al. do not explicitly teach a method of treating cancer comprising administering a therapeutically effective amount of the compound of claim 1 to a subject in need thereof.
Johnstone et al. teach heparan sulfate (HS) mimetics that are polysulfated penta- and tetrasaccharide glycosides (Abstract). These HS mimetics are evaluated for their antiangiogenic activity in a series of in vitro and ex vivo assays. In general, the compounds exhibit superior activity to the phase III HS mimetic 1 in cell-based assays indicative of angiogenesis, and importantly, tetrasaccharides, which are likely to be cheaper to manufacture than pentasaccharides. Moreover, compounds 4 and 5:
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show potent antitumor activity in vivo in a mouse melanoma model. The data support the continued development of HS mimetics of this type as antiangiogenic, anticancer agents (page 1691, Right Col., para. 1).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to administer a therapeutically effective amount of compound 39 as taught by Tiruchinapally et al. for treating cancer because Tiruchinapally et al. teach compound 39, a defined heparin/heparan sulfate oligosaccharide derivative and further teach that heparin and heparan sulfates play important roles in biological events including tumor metastasis, and that their biological functions depend on sulfation patterns and backbone sequences and Johnstone et al. teach that sulfated oligosaccharide glycosides functioning as heparan sulfate mimetics, including tetrasaccharide glycoside, exhibit antiangiogenic activity and that compounds 4 and 5 show potent antitumor activity in vivo in a mouse melanoma model. Johnstone et al. teach HS mimetics contain α(1[Wingdings font/0xE0]3)/α(1[Wingdings font/0xE0]2) glycosidic linkages and Johnstone et al. do not teach the identical linkage pattern of compound 39. However, Johnstone et al. are not relied upon for teaching the specific claimed compound structure and Tiruchinapally et al. teach the claimed compound. Johnstone et al. are relied upon for the teaching the sulfated oligosaccharide HS mimetics, including tetrasaccharide glycosides, are useful as anticancer agents. Thus, a person of ordinary skill in the art would have been motivated to use the defined sulfated heparan sulfate oligosaccharide compound 39 of Tiruchinapally et al. as an anticancer agent. A person of ordinary skill in the art would have had a reasonable expectation of success because compound 39 of Tiruchinapally et al. and HS mimetics of Johnstone et al. are sulfated oligosaccharide glycosides designed to mimic heparan sulfate biological activity. Johnstone et al. demonstrate that sulfated oligosaccharide HS mimetics, including tetrasaccharide glycosides, exhibit antitumor activity in vivo, while Tiruchinapally et al. teach that defined sulfation and backbone structures are important for heparin/heparan sulfate biological function.
Conclusion
No claim is found to be allowable.
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/H.Y.L./Examiner, Art Unit 1693
/SCARLETT Y GOON/Supervisory Patent Examiner
Art Unit 1693
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