--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 .
Applicant’s response dated September 25, 2026 is acknowledged.
Priority
This application is a continuation of 16/765,627 filed on 05/20/2020, which is a 371 of
PCT/EP2018/082178 filed on 11/22/2018, and claims foreign priority in GB 1719464.8 filed on
11/23/2017.
Claim Status
Claims 1-30 are pending and examined. Claims 1-6, 8, 9, 11, 14-19, 22, 26, and 28-30 were amended.
Withdrawn Claim Rejections -35 USC§ 112(b)
Rejections of claims 2-6, 8, 9, 11, 14-19, 22, and 28-30 are withdrawn because rejections were obviated with claim amendments.
Withdrawn Claim Rejections - 35 USC § 102
Rejection of claim 26 as being anticipated by Mylius (Justus Liebigs Analen Der Chemie, Volume 587, Published January 7, 1954, pages 1-15 – English language translation appended thereto - of record in IDS dated 06/01/2023) is withdrawn because the claim was amended to require a eutectic mixture of paeonol and apocynin, which are not taught by Mylius.
Maintained Claim Rejections - 35 USC § 103
Modified as Necessitated by Amendment
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.
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.
Claims 1-9, 11, 23-25, 28, and 29 are rejected under 35 USC 103 as being obvious over
Larkins et al. (GB2424833 A, published 11/10/2006 – of record in IDS dated 06/01/2023) in
view of Gullapalli et al. (International Journal of Pharmaceutics 496 (2015) 219-239 - of record
in IDS dated 06/01/2023).
The claims encompass a liquid formulation comprising active compounds 2-hydroxy-4-
methoxyacetophenone (paeonol) or isomer thereof and 4-hydroxy-3-methoxyacetophenone (apocynin) or isomer thereof wherein the ratio by weight of paeonol or isomer thereof to apocynin or isomer thereof is from 3 :2 to 9: 1; and at least one excipient wherein the ratio by
weight of total active compounds to the at least one excipient is from 2:3 to 19: 1.
Larkins teaches compositions comprising apocynin and paeonol and methods of using to
treat inflammatory disease (Abstract). A preferred composition comprises apocynin and paeonol
in a weight ratio between about 1 to 100 and about 100 to 1, and preferably between about 1 :2 to
1: 10 (page 7 lines 3-8). The composition further comprises pharmaceutically conventional
carriers, diluents, flavorings, emulsifiers, and stabilizers (page 8 lines 16-19). A daily dose of the
composition may be provided as a single capsule, tablet, or other solid or liquid form known to the skilled artisan (page 12 lines 7-9). The composition is preferably administered orally (page 13 lines 11-14).
Larkins does not teach at least one excipient as required by the claims and a weight ratio
of the total active compounds to the at least one excipient.
Gullapalli teaches that polyethylene glycols (PEGs) are frequently employed as vehicles
in oral and parenteral dosage forms (abstract). Gullapalli teaches that PEGs are commercially
available in molecular weight grades from 200 to 10,000,000 g/mol. PEGs of molecular weight
200-600 are clear liquids and those of 1000 and above exist as semi-crystalline solids at room
temperature (see page 220, Introduction section).
The teachings of Larkins and Gullapalli are related to carriers for oral dosage forms and it
would have been obvious to have combined their teachings because they are in the same field of
endeavor. It would have been prima facie obvious to a person of ordinary skill in the art before
the effective filing date of the claimed invention to have formed a liquid formulation for oral
administration, the formulation comprising a conventional carrier, and a combination of paeonol
and apocynin in a weight ratio from 100:1 to 1:100 and preferably from 1:2 to 1:10, with a
reasonable expectation of success because Larkins teaches a formulation comprising a
combination of paeonol and apocynin in a weight ratio from 100: 1 to 1: 100 and preferably from
1 :2 to 1: 10, and a pharmaceutically conventional carrier, wherein the formulation is a liquid
formulation and suitable for oral administration. Larkins does not teach suitable carriers for
making a liquid formulation. It would have been obvious to the skilled artisan to have looked to
Gullapalli because Gullapalli teaches that PEGs are ideal drug delivery vehicles because of their
ability to be miscible with aqueous fluids in all proportions and dissolve many poorly water soluble compounds (page 220, section 2). Gullapalli teaches commercially available PEGs
include PEGs having molecular weight grades from 200 to 10,000,000 g/mol. PEGs of molecular
weight 200-600 are clear liquids and those of 1000 and above exist as semi-crystalline solids at
room temperature (see page 220, Introduction section). Thus, it would have been obvious to one
of ordinary skill in the art to have selected PEG 400 and utilized it to make the liquid formulation
in Larkins, with a reasonable expectation of success because PEG-400 was known as a clear
liquid suitable for solubilizing poorly water-soluble compounds and the purpose of Larkins was
to form a liquid formulation. The selection of a known material suitable for its intended purpose
supports obviousness.
The formulation in claim 1 is obvious over Larkins modified with Gullapalli because the
formulation is a liquid formulation comprising PEG-400 as the pharmaceutically conventional
carrier, and a combination of paeonol and apocynin in the range of ratios by weight from 2: 1 to
10: 1. The claimed range of weight ratios of paeonol to apocyanin (from 3 :2 to 9: 1) is obvious
because it overlaps with the preferred prior art range of from about 2: 1 to 10: 1. A range of from
3 :2 to 9: 1 is equivalent to a range of from 60:40 to 90: 10. A range of from about 2: 1 to about
10: 1 is equivalent to a range of from about 67:33 to about 91 :9. The claimed range of weight
ratios of paeonol to apocynin is obvious because it overlaps with the prior art range, and it has
been held that in the case where the claimed ranges overlap or lie inside ranges disclosed by the
prior art a prima facie case of obviousness exists.
Regarding weight ratio ranges of total active compounds to the at least one excipient in
claims 2, 8, 11, 28, and 29, Larkins does not teach the weight ratio of total active compounds to
excipients in a liquid formulation. It would have been obvious to the skilled artisan to determine
a concentration range of PEG-400 that is sufficient to form a liquid formulation of paeonol and
apocynin. One of ordinary skill in the art would have arrived at the concentration range through
routine experimentation. The claimed range of weight ratios is obvious because it is at least close
enough to the prior art range of weight ratios that a person skilled in the art would have expected
them to have the same properties. Both present claims and the prior art require a liquid
formulation comprising PEG-400 as the carrier, and a combination of apocynin and paeonol as
active agents. There would have been a reasonable expectation of success in arriving at the
claimed invention, including claimed weight ratios of active agents to excipient, through routine
experimentation. The specification was reviewed and there is no evidence that the claimed
combination of elements and their respective weight ratios are critical. Determining optimal
concentrations is routine experimentation and is readily practiced by one of ordinary skill.
Regarding claims 3-6, PEG-400 meets the claimed limitations.
Regarding claim 7, the preferred range of paeonol to apocynin is from about 2: 1 to about
10: 1, which is equivalent to a range of from about 67:33 to about 91 :9. The claimed range of
weight ratios of paeonol to apocynin is obvious because it overlaps with the prior art range.
Regarding claim 9, the prior art formulation contains the same elements as claimed
formulation and it would have been reasonable to the skilled artisan to conclude that the prior art
composition has the same properties as claimed composition when placed under identical
conditions, including being stable at room temperature.
Regarding claims 23 and 24, prior art formulation contains the same components as
claimed and it would have been suitable for treatment of inflammatory disease and
neurodegenerative disease.
Regarding claim 25, it would have been obvious to have used the formulation to treat an
inflammatory disease comprising administering the composition to a patient in need thereof, with
a reasonable expectation of success because Larkins teaches that the compositions are suitable
for the treatment of inflammatory diseases (page 9 lines 5-12), where the composition is
administered to a subject (page 11 lines 5-15).
Claims 1-5, 7-9, 11, 23-25, 28, and 29 are rejected under 35 U.S.C. 103 as being
unpatentable over Larkins (US 8,841,348 B2, Published September 23, 2014).
The claims encompass a liquid formulation as described by the claims.
The teachings of Larkins are related to compositions comprising apocynin and paeonol
(Abstract). A preferred composition comprises apocynin and paeonol in a ratio by weight
between about 1 :2 to 1: 10 (paragraph bridging columns 2-3). The compositions are suitable for
oral administration and are formed by methods known in the art. For example, compositions are
prepared using pharmaceutically acceptable carriers, and may be in the form of a liquid. The
compositions may be formed as a soft capsule, where the composition is dissolved in an
appropriate liquid such as polyethylene glycol (column 4 lines 23-44).
It would have been prima facie obvious to a person of ordinary skill in the art before the
effective filing date of the claimed invention to have formed a liquid formulation for oral
administration, the formulation comprising polyethylene glycol as a carrier, and a combination of
paeonol and apocynin in a weight ratio from 1 :2 to 1: 10, with a reasonable expectation of
success because Larkins teaches a formulation comprising a combination of paeonol and
apocynin in a preferred weight ratio from 1 :2 to 1: 10, and a carrier selected from polyethylene
glycol, wherein the formulation is a liquid formulation and suitable for oral administration.
The formulation in claim 1 is obvious over Larkins because the formulation is a liquid
formulation comprising polyethylene glycol carrier, and a combination of paeonol and apocynin
in the range of ratios by weight from 2: 1 to 10: 1. The claimed range of weight ratios of paeonol
to apocyanin (from 3 :2 to 9: 1) is obvious because it overlaps with the preferred prior art range of from about 2: 1 to 10: 1. A range of from 3 :2 to 9: 1 is equivalent to a range of from 60:40 to
90: 10. A range of from about 2:1 to about 10:1 is equivalent to a range of from about 67:33 to
about 91: 9. The claimed range of weight ratios of paeonol to apocynin is obvious because it
overlaps with the prior art range, and it has been held that in the case where the claimed ranges
overlap or lie inside ranges disclosed by the prior art a prima facie case of obviousness exists.
Regarding weight ratio ranges of total active compounds to the at least one excipient in
claims 2, 8, 11, 28, and 29, Larkins does not teach the weight ratio of total active compounds to
excipients in a liquid formulation. It would have been obvious to the skilled artisan to determine
a concentration range of polyethylene glycol that is sufficient to form a liquid formulation of
paeonol and apocynin dissolved in PEG. One of ordinary skill in the art would have arrived at
the concentration range through routine experimentation. The claimed range of weight ratios is
obvious because it is at least close enough to the prior art range of weight ratios that a person
skilled in the art would have expected them to have the same properties. Both present claims and
the prior art require a liquid formulation comprising polyethylene glycol as the carrier, and a
combination of apocynin and paeonol as active agents. There would have been a reasonable
expectation of success in arriving at the claimed invention, including claimed weight ratios of
active agents to excipient, through routine experimentation. The specification was reviewed and
there is no evidence that the claimed combination of elements and their respective weight ratios
are critical. Determining optimal concentrations is routine experimentation and is readily
practiced by one of ordinary skill.
Regarding claims 3-5, polyethylene glycol meets the claimed limitations.
Regarding claim 7, the preferred range of paeonol to apocynin is from about 2: 1 to about
10: 1, which is equivalent to a range of from about 67:33 to about 91 :9. The claimed range of
weight ratios of paeonol to apocynin is obvious because it overlaps with the prior art range.
Regarding claim 9, the prior art formulation contains the same components as claimed
formulation and it would have been reasonable to the skilled artisan to conclude that the prior art
composition has the same properties as claimed composition when placed under identical
conditions, including being stable at room temperature.
Regarding claims 23 and 24, prior art formulation contains the same components as
claimed and it would have been suitable for treatment of inflammatory disease and
neurodegenerative disease.
Regarding claim 25, it would have been obvious to have used the formulation to treat an
inflammatory disease comprising administering the composition to a patient in need thereof, with
a reasonable expectation of success because Larkins teaches that the compositions are suitable
for the treatment of inflammatory diseases ( column 5 lines 1-3), where the composition is
administered to a subject (column 5 lines 25-35).
Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over Larkins as applied to
claims 1-5, 7-9, 11, 23-25, 28, and 29 above, and further in view of Gullapalli.
The claim is drawn to a composition of claim 1 wherein the at least one excipient is
polyethylene glycol 400.
The teachings of Larkins are relied upon as summarized above. Larkins does not
specifically teach PEG-400.
Gullapalli teaches that polyethylene glycols (PEGs) are frequently employed as vehicles
in oral and parenteral dosage forms (abstract). Gullapalli teaches that PEGs are commercially
available in molecular weight grades from 200 to 10,000,000 g/mol. PEGs of molecular weight
200-600 are clear liquids and those of 1000 and above exist as semi-crystalline solids at room
temperature (see page 220, Introduction section).
The teachings of Larkins and Gullapalli are related to carriers for oral dosage forms and it
would have been obvious to have combined their teachings because they are in the same field of
endeavor. Larkins does not teach specific PEGs suitable for making liquid formulations. It would
have been prima facie obvious to a person skilled in the art to have selected PEG-400 because it
was known from Gullapalli that PEG 200-600 is a clear liquid that is suitable for making liquid
formulations of compositions intended for oral administration. Combining prior art elements
according to known methods to obtain predictable results supports obviousness and the selection
of a known material suitable for its intended purpose supports obviousness.
Maintained Double Patenting Rejections
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 7, 9, 10, 12, 13, 19-24, 26, and 27 are rejected on the ground of nonstatutory
double patenting as being unpatentable over claims 1-4 of U.S. Patent No. 11,701,325 B2.
Although the claims at issue are not identical, they are not patentably distinct from each other
because patented claims are dawn to liquid formulations comprising a eutectic mixture of
paeonol or isomer thereof and apocynin or isomer thereof, and an excipient, which renders the
compositions in claims 1, 7, 10, 12, 13, 19, 20, 21, 26, and 27 obvious. Regarding the ratio range
in claim 7, the ratio is a eutectic ratio of the two compounds as evidenced by instant claim 21.
Claims 9 and 22 are obvious because patented composition contains the same components as
instantly claimed composition and it would have been obvious to expect the patented
composition to have the same properties as claimed composition when placed under identical
conditions. Claims 23 and 24 are obvious because patented composition would have been
suitable for treating inflammatory disease and neurodegenerative disease because patented
composition has the same components as instantly claimed composition.
Claims 2-6, 8, 11, 14-18, 25, and 28-30 are rejected on the ground of nonstatutory double
patenting as being unpatentable over claims 1-4 of U.S. Patent No. 11,701,325 B2 as applied to
claims 1, 7, 9, 10, 12, 13, 19, 19-24, 26, and 27 above, and further in view of Larkins et al.
(GB2424833 A, published 11/10/2006 - ofrecord in IDS dated 06/01/2023) in view of
Gullapalli et al. (International Journal of Pharmaceutics 496 (2015) 219-239 – of record in IDS
dated 06/01/2023).
The teachings of patented claims, Larkins, and Gullapelli are relied upon as summarized
above.
It would have been prima facie obvious to a person of ordinary skill in the art before the
effective filing date of the claimed invention to have formed the liquid formulation in patented
claims using PEG-400 because Larkins teaches a liquid formulation comprising a mixture of
apocynin and paeonol and an excipient, useful for treating inflammatory conditions by
administering orally to a subject in need; and it was known from Gullapelli that PEG-400 is a
commercially available liquid excipient suitable for making liquid oral formulations. Limitations
in claims 2-6 and 14-17 are met with PEG-400.
Regarding weight ratio ranges of total active compounds to the at least one excipient in
claims 2, 8, 11, 18, 28, 29, and 30, patented claims and Larkins do not teach the weight ratio of
total active compounds to excipients in a liquid formulation. It would have been obvious to the
skilled artisan to determine a concentration range of PEG-400 that is sufficient to form a liquid
formulation of paeonol and apocynin dissolved in PEG-400. One of ordinary skill in the art
would have arrived at the claimed range of ratios through routine experimentation. The claimed
range of weight ratios is obvious because it is at least close enough to the prior art range of
weight ratios that a person skilled in the art would have expected them to have the same
properties. Both present claims and patented claims modified by Larkins and Gullapelli require a
liquid formulation comprising polyethylene glycol as the carrier, and a combination of apocynin
and paeonol as active agents. There would have been a reasonable expectation of success in
arriving at the claimed invention, including claimed weight ratios of active agents to excipient,
through routine experimentation. The specification was reviewed and there is no evidence that
the claimed combination of elements and their respective weight ratios are critical. Determining
optimal concentrations is routine experimentation and is readily practiced by one of ordinary
skill.
Regarding claim 25, it would have been obvious to have used the patented formulation as
modified by Larkins and Gullapelli to treat an inflammatory disease comprising administering
the composition to a patient in need thereof, with a reasonable expectation of success because
Larkins teaches that the compositions are suitable for the treatment of inflammatory diseases,
where the composition is administered to a subject.
Response to Arguments
Applicant’s arguments submitted in the remarks dated September 25, 2026 were fully considered but are not persuasive for the following reasons.
Double patenting rejections are maintained because applicant’s arguments are not persuasive. The additional elements recited in instant claims would have been obvious to add to the compositions of patented claims in view of the secondary references as described in the office action.
Argument’s against Larkins ‘833 are not persuasive because the references is not limited by the exemplified composition. Larkins ‘833 teaches liquid formulations and the skilled artisan would have been capable of selecting appropriate excipients to make a liquid formulation. One of skill would not be motivated away from adding a liquid excipient to make a liquid formulation because Larkins ‘833 expressly teaches that the active agents may be formulated into a liquid formulation.
Arguments related to unexpected results are not persuasive because the claims are not commensurate in scope with examples 1-3 which contain 3.5 parts by wt. paeonol and 1 part by wt. apocynin, which provides a eutectic mixture. The claims are broader because they encompass isomers of these compounds and the applicant did not show that eutectic mixtures of all of the claimed combinations of compounds would be formed when in a 3.5:1 weight ratio as claimed. The claims do not recite PEG 400, which is required by the exemplified compositions. The exemplified compositions are each made from three specific chemical compounds in specific amounts, whereas the claims do not recite any amounts and only some claims require at least one excipient comprising PEG 400. Applicant stated that the inventive liquid formulation possesses a high concentration of active compounds, however instant claims do not limit the concentration of active agents in the formulation. The applicant did not show with data that the asserted stability would have occurred over the entire breadth of the claims. It is not clear why the applicant concluded that forming a stable liquid at room temperature is considered unexpected in view of the record. It is also not clear what property or characteristic of the compositions in examples 1-3 make the compositions “a stable liquid at room temperature”, and the skilled artisan could not determine if compositions of the prior art would possess those characteristics. Applicant has not provided any comparative results, comparison to the closes prior art, nor data showing that concentration of active compounds is critical. The applicant has not met the requirements set forth in MPEP 716.02 that applicant has to meet in order to overcome an obviousness rejection with secondary considerations.
Arguments against Gullapalli are not persuasive because Larkins ‘833 is not deficient for reasons described above.
The declaration was not considered because it was not prepared for the instant application. All references in the declaration are made to claims in application 16/765,627, which have a different scope than instant claims. The data presented in the declaration is for a eutectic mixture of paeonol and apocynin in PEG-400, whereas the presently claimed compositions are broader and the declaration does not present any evidence to suggest that the asserted unexpected result would have occurred for every claimed combination of components and in any amount.
Applicant’s arguments against Larkins ‘348 are unpersuasive for the same reasons as provided above.
Arguments against the rejection of claim 11 are not persuasive because arguments are based on limitations that are not claimed. Instant claims do not limit the concentration of active agents, thus “an improved formulation with high concentration of paeonol and apocynin in a small volume” is not a claimed limitation. The claims only recite weight ratios of active agents to each other and weight ratios of active agents to the excipient. The claims use the transitional phrase “comprising” and do not limit any of the recited components by concentration in the formulation, which means that the recited components can be present in any concentration. Both Larkins references teach formulating the active agent in a liquid formulation and that teaching is sufficient to motivate the skilled artisan to make a liquid formulation comprising the two active agents. The skilled artisan would have been capable of combining the two active agents with suitable excipients, such as PEG-400, in order to formulate a liquid composition comprising the two active agents with a reasonable expectation of success. The specification was reviewed and there is no evidence that the claimed weight ratio ranges are critical.
Conclusion
No claims are allowed.
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/ALMA PIPIC/Primary Examiner, Art Unit 1617
