Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
This office action is in reply to the application filed with amended claims on 28 July 2023. Claims 1-17, 22-26, 31-33, 38-39, 43, 47, 49, 51-52, 56, 60, and 62 are amended. Claims 18-21, 27-30, 34-37, 40-42, 44-46, 48, 50, 53-55, 57-59, and 61 are canceled. Claims, referring to compound formula (I) and related structures 1-16, referring to fillers, disintegrants, lubricants, surfactants, or fillers 17, 22-26, preparation comprising inhibitor and filler (etc.) 31-33, 38-39, 43, 47, 49, 51-52, 56, and 60, and referring to a method for treating a disease 62 are pending.
Priority
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in parent Application No. 18/263,434, filed on 28 July 2023. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 28 July 2023 and 08 February 2024 was filed after the mailing date of the application on 28 July 2023. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
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.
Claims 1-17, 22-26, 31, and 62 are rejected under 35 U.S.C. 103 as being unpatentable over Mao et al. ((1,2,4)triazolo(1,5-a)pyridine compound as JAK inhibitor and application thereof, AU2019326647B2, 2020) in view of Rowe et al. (Handbook of pharmaceutical excipients, 6th edition, Pharmaceutical Press, 2009).
Mao discloses a [1,2,4]triazolo[1,5-a]pyridine Markush structure with several exemplifications and described as a JAK inhibitor with the implication of treating JAK1 or TYK2 related diseases utilizing a compound represented by the illustrated Markush formula I or a pharmaceutically acceptable salt of that compound.
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This is further expanded upon where Mao specifies that the substitution pattern includes: E1 and E2 are independently selected from single bond, -CH2 or –(CH2)2-; L1 is selected from single bond, -(CH2)g-, -C(=O)- or -C(=O)-(CH2)h-; m is 1 or 2; n is 1 or 2; g is 1, 2 or 3; h is 1, 2 or 3; RI is selected from H, CN, Cl-6 alkyl group or 3~6-membered cycloalkyl group, wherein the above Cl- 6 alkyl group and 3~6-membered cycloalkyl group are optionally substituted by 1, 2 or 3 Ra; R2 is selected from H, F, Cl, Br, I or Cl-3 alkyl groups, wherein the above Cl-3 alkyl group is optionally substituted by 1, 2 or 3 Rb; R3, R4 and R5 are independently selected from H, F, Cl, Br, I or Cl-3 alkyl group, wherein the above Cl-3 alkyl group is optionally substituted by 1, 2 or 3 Rc; R6, R7 and R8 are independently selected from H, F, Cl, Br, I or Cl-3 alkyl group, wherein the above Cl-3 alkyl group is optionally substituted by 1, 2 or 3 Rd; Each Ra is independently selected from H, F, Cl, Br, I, CN or Cl-3 alkyl group, wherein the above Cl-3 alkyl group is optionally substituted by 1, 2 or 3 R; Each Rb is independently selected from F, Cl, Br or I; Each Rc is independently selected from F, Cl, Br or I; Each Rd is independently selected from F, Cl, Br or I; Each R is independently selected from F, Cl, Br or I ; the isomers are selected from geometrical isomers, stereoisomers or tautomers, in comparison to claim 1.
Mao further specifies that in some embodiments of the present application, each of the above Ra is independently selected from H, F, Cl, Br, I or CN, and other variables are as defined in the present application, in comparison to claim 2.
Mao further specifies that in some embodiments of the present application, the above Ri is selected from H, CN, C1.3 alkyl group or 3~5-membered cycloalkyl group, in which the C1.3 and 3~5-membered cycloalkyl group are optionally substituted by one, two or three Ra, and other variables are as defined in the present application, in comparison to claim 3.
Mao further specifies that in some embodiments of the present application, the above Ri is selected from H, CN, CH3,
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,
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, in which CH3,
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are optionally substituted by one, two or three Ra, and other variables are as defined in the present application, in comparison to claim 4.
Mao further specifies that in some embodiments of the present application, the above Ri is selected from H, CN, CF3, CHF2,
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, in comparison to claim 5.
Mao further specifies that in some embodiments of the present application, the above R2 is selected from H, F, Cl, Br or I, and other variables are as defined in the present application, in comparison to claim 6.
Mao further specifies that in some embodiments of the present application, the above R3, R4 and Rs are independently selected from H, F, Cl, Br or I, and other variables are as defined in the present application, in comparison to claim 7.
Mao further specifies that in some embodiments of the present application, the above Re, R7 and Rs are independently selected from H, F, Cl, Br or I, and other variables are as defined in the present application, in comparison to claim 8.
Mao further specifies that in some embodiments of the present application, the above Li is selected from single bond, -CH2-, -(012)2-, -C(=O)- or -C(=O)-(CH2)-, and other variables are as defined in the present application, in comparison to claim 9.
Mao further specifies that in some embodiments of the present application, the above structure unit
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is selected from
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or
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or
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, in comparison to claim 10.
Mao further specifies that in some embodiments of the present application, the above structure unit
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is selected from
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,
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, in comparison to claim 11.
Mao further specifies that in some embodiments of the present application , the above structure unit
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is selected from
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in comparison to claim 12.
Mao further specifies that in some embodiments of the present application, the above compound of formula (I), isomers thereof, or pharmaceutically acceptable salts thereof, are selected from
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, in comparison to claim 13.
Mao further specifies that in some embodiments of the present application, the above compounds of formula (I), isomers thereof, or pharmaceutically acceptable salts thereof, are selected from
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, in comparison to claim 14.
Mao also provides the following compounds as examples:
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, in comparison to claim 15.
Mao also provides the following compounds as examples:
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, in comparison to claim 16.
Mao also discloses exploration of in vivo efficacy study in collagen-induced arthritis in mice as an exploration into rheumatoid arthritis. Rheumatoid arthritis is described a type of multiple autoimmune diseases with a global incidence rate of 1%, leading to inflammation, damage, and malformation of arthrosis, and systemic inflammation reactions. In the collagen-induced mice arthritis model, type II collagen was used to induce arthritis in DBA/1 mice via tail injections. The regimen was conducted over 28 days, dexamethasone was used as a reference drug, with dosing done at 0.3 mg/kg and 15 mg/kg, with experimental cohorts dosed BID for 14 days. The mice were evaluated via clinical scores with certain experimental compounds at 15 mg/kg demonstratively reducing collagen-induced arthritis in a statistically significant number of the experimental population.
Mao does not, however, teach an oral preparation comprising the JAK inhibitors of a compound of formula I and a pharmaceutical excipient.
This deficiency is rectified by Rowe who extensively covers many topics within the field of drug formulation, including, but not limited to, typical properties of select excipients, incompatibilities, safety, related substances, along with numerous other examples in the categories of fillers, disintegrants, adhesives, lubricants, and surfactants, such as microcrystalline cellulose for fillers, carboxymethyl starch sodium for disintegrants, methyl cellulose for adhesives, magnesium stearate for lubricants, and sodium dodecyl sulfate for surfactants. As such, it would have been prima facie obvious, to a person of ordinary skill in the art, to explore well known and documented excipients to develop an oral preparation involving a pharmaceutical composition appropriate for a compound that inhibits JAK utilizing well established literature that is exemplified by Rowe.
Claim 32 is rejected under 35 U.S.C. 103 as being unpatentable over Mao et al. ((1,2,4)triazolo(1,5-a)pyridine compound as JAK inhibitor and application thereof, AU2019326647B2, 2020) and Rowe et al. (Handbook of pharmaceutical excipients, 6th edition, Pharmaceutical Press, 2009) as applied to claims 1-17, 22-26, and 31 above, and further in view of A. Beelen & J. C. Strum (G1T38 superior dosage regimes, US 2020/0405721 A1, 2020).
Mao teaches triazolopyridines as JAK inhibitors while Rowe teaches excipients and application thereof.
They, however, do not teach the JAK inhibitor consisting of 1% to 50%, 5% to 40%, 6% to 30%, 8% to 25%, 10%, 15%, or 20% of the total weight of the oral inhibitor composition.
Beelen & Strum rectifies this deficiency by teaching that pharmaceutical compositions can be formulated for oral administration and can contain any amount of active compound that achieves the desired result, e.g. between 0.1% and 99% weight % of the compounds and usually at least about 5 wt. % though some embodiments contain at least about 10%, 15%, 25%, 25 wt. % to about 50 wt. % or from about 5 wt. % to about 75 wt. % of the active compound (para. 135). A prima facie case of obviousness necessarily exists when the prior art range overlaps or touches a claimed range, such as in the instant rejection. MPEP § 2144.05. As such, it would have been prima facie obvious, to a person of ordinary skill in the art, to consider utilizing the JAK inhibitor of interest in the preferred 10%, 15%, 20 wt. % composition to achieve a therapeutically effective outcome.
Claim 33 is rejected under 35 U.S.C. 103 as being unpatentable over Mao et al. ((1,2,4)triazolo(1,5-a)pyridine compound as JAK inhibitor and application thereof, AU2019326647B2, 2020) and Rowe et al. (Handbook of pharmaceutical excipients, 6th edition, Pharmaceutical Press, 2009) as applied to claims 1-17, 22-26, and 31 above, and further in view of Roslan et al. (Comparison of various fillers on the physical properties of compounded tablets, J. Pharma. Neg. Results 2022, 13, 7).
Mao teaches triazolopyridines as JAK inhibitors while Rowe teaches excipients and application thereof.
They, however, do not teach the use of one or more fillers selected from at least one of microcrystalline cellulose, lactose pre-gelatinized starch, and anhydrous dicalcium phosphate, the content of microcrystalline cellulose or lactose being 0% to 78.5%, 10% to 70%, 20% to 60%, 30% to 50%, 31.75%, 37.25%, 39.25%, 41.75%, 42.25% or 43.75 wt. % of the composition, and the content of pre-gelatinized starch, and anhydrous dicalcium phosphate being 0% to 78.5%, 10% to 70%, 20% to 60^, 30% to 50%, and 39.25 wt. % of the composition.
Roslan addresses this by teaching that fillers are pharmaceutical ingredients that are not pharmaceutically active but essential in tablet preparation, consisting of heterogeneous groups of substances intended to generate the necessary amount when the drug dosage itself is sufficient to generate the required bulk and that the range of fillers in a pharmaceutical formulation may differ from 5% to 80%. A prima facie case of obviousness necessarily exists when the prior art range overlaps or touches a claimed range, such as in the instant rejection. MPEP § 2144.05. As such, it would have been prima facie obvious, to a person of ordinary skill in the art, to consider the use of fillers, including microcrystalline cellulose, lactose pre-gelatinized starch, and anhydrous dicalcium phosphate, in the development of an oral formulation appropriate for administering a potential JAK inhibitor.
Claim 38 is rejected under 35 U.S.C. 103 as being unpatentable over Mao et al. ((1,2,4)triazolo(1,5-a)pyridine compound as JAK inhibitor and application thereof, AU2019326647B2, 2020) and Rowe et al. (Handbook of pharmaceutical excipients, 6th edition, Pharmaceutical Press, 2009) as applied to claims 1-17, 22-26, and 31 above, and further in view of Meggle (Meggle Technical brochure MicroceLac100, Meggle, 2019).
Mao teaches triazolopyridines as JAK inhibitors while Rowe teaches excipients and application thereof.
They, however, do not teach the use of a filling agent that is a mixture of lactose and microcrystalline cellulose, with a weight ratio of 0:1, 5:3, 3:1, 1:1, 1:0 for lactose and microcrystalline cellulose.
Meggle overcomes this by teaching MicroceLac100, co-processed lactose and microcrystalline cellulose designed for direct compression, comprising 75% lactose and 25% microcrystalline cellulose, for the optimal synergistic functional performance, such as increased compactibility and powder flow, that creates a monoparticulate system with two compaction mechanisms, brittle fracture and plastic deformation, giving the desirable properties for direct compression while maintaining their individual chemical identities. A prima facie case of obviousness necessarily exists when the prior art range overlaps or touches a claimed range, such as in the instant rejection. MPEP § 2144.05. As such, it would have been prima facie obvious, to a person of ordinary skill in the art, to consider the use of a combination of lactose and microcrystalline cellulose as fillers for an oral administration composition due to the advertised relevant and superior properties by Meggle.
Claims 39 and 43 are rejected under 35 U.S.C. 103 as being unpatentable over Mao et al. ((1,2,4)triazolo(1,5-a)pyridine compound as JAK inhibitor and application thereof, AU2019326647B2, 2020) and Rowe et al. (Handbook of pharmaceutical excipients, 6th edition, Pharmaceutical Press, 2009) as applied to claims 1-17, 22-26, and 31 above, and further in view of PharmaState Academy (Excipients used in tablets, https://pharmastate.academy/excipients-used-in-tablets/, 2017).
Mao teaches triazolopyridines as JAK inhibitors while Rowe teaches excipients and application thereof.
They do not, however, teach the use of one or more disintegrants selected from a group consisting of cross-linked carboxymethyl cellulose sodium, carboxymethyl starch sodium, cross-linked povidone and dry starch, where cross-linked carboxymethyl cellulose sodium is 2%-16%, 4%, 8%, or 12% of the total weight of the composition, and the content of sodium carboxymethyl starch or cross-linked polyvinylketone is 2% to 16%, or 8% of the total weight of the composition. Additionally, they do not teach one or more adhesives selected from a group including hypromellose, carboxymethyl cellulose, hydroxpropyl cellulose povidone, methyl cellulose, and ethyl cellulose, the content of Hypromellose, hydroxypropyl cellulose, or povidone is 0.1% to 5%, 1% to 4%, 2% to 3%, or 1.5% of the total weight of the composition.
PharmaState Academy rectifies this by teaching that the use of disintegrants, excipients that are incorporated into the formulation of tablets or capsules to promote their disintegration when they come into contact with liquid or fluid matter, including cross-linked carboxymethyl cellulose and polyplasonde (cross-linked povidone) being 10% to 20 wt. % and 2 wt.%, respectively. Cellulose is described as highly hydrophilic and water-soluble compounds with controllable cross-linking, capable of rapid swelling and wicking, whereas cross-linked povidone is described as swelling very little, water insoluble and spongy. Both ingredients are described as super disintegrants, designed to have greater effectiveness at low concentrations when compared to other traditional disintegrants. PharmaState Academy also teaches that binders and adhesives are materials added in wet or dry form to form granules or cohesive compacts for directly compressed tablets, with examples including cellulose derivatives such as methyl cellulose, hydroxy propyl cellulose, hydroxy propyl cellulose, gelatin, glucose, povidone (2%) or starch paste. A prima facie case of obviousness necessarily exists when the prior art range overlaps or touches a claimed range, such as in the instant rejection. MPEP § 2144.05. As such, it would have been prima facie obvious, to a person of ordinary skill in the art, to consider the use cross-linked carboxymethyl cellulose, cross-linked povidone within the prescribed weight ranges as described by references in the field of excipients and the described adhesives above, such as povidone, to achieve the desired performance characteristics as described by the literature within the field of excipients, for the development of an oral composition appropriate for the delivery of JAK inhibitors in oral administration.
Claim 47 is rejected under 35 U.S.C. 103 as being unpatentable over Mao et al. ((1,2,4)triazolo(1,5-a)pyridine compound as JAK inhibitor and application thereof, AU2019326647B2, 2020) and Rowe et al. (Handbook of pharmaceutical excipients, 6th edition, Pharmaceutical Press, 2009) as applied to claims 1-17, 22-26, and 31 above, and further in view of PharmaExcipients (Lubricants – Pharmaceutical Excipients, https://www.pharmaexcipients.com/lubricants/, 2023).
Mao teaches triazolopyridines as JAK inhibitors while Rowe teaches excipients and application thereof.
They do not, however, teach the use of one or more lubricants selected from magnesium stearate, micropowder silica gel, talcum powder, hydrogenated vegetable oil, polyethylene glycol, and sodium dodecyl sulfate, where the content of the lubricant is 0.1% to 5%, 0.5% to 3%, or 1% of the total weight of the composition.
PharmaExcipients overcomes this absence by teaching that lubricant excipients are substances added to formulations to aid in the tableting process and to improve flow of powders during manufacturing, reducing friction and preventing the sticking of the tablet material. This is further expanded to include factors such as compatibility on the active ingredient, stability and bioavailability, effect on physical properties, and compatibility with equipment and the manufacturing process. Several commonly used lubricants were listed including the optimal concentration in solid dosage forms including sodium stearate (0.25% to 2%) and talc (1% to 5%). A prima facie case of obviousness necessarily exists when the prior art range overlaps or touches a claimed range, such as in the instant rejection. MPEP § 2144.05. As such, it would have been prima facie obvious, to a person of ordinary skill in the art, to consider the use the described lubricants above, such as sodium stearate, to achieve the desired performance characteristics as described by the literature within the field of excipients, for the development of an oral composition appropriate for the delivery of JAK inhibitors in oral administration.
Claim 49 is rejected under 35 U.S.C. 103 as being unpatentable over Mao et al. ((1,2,4)triazolo(1,5-a)pyridine compound as JAK inhibitor and application thereof, AU2019326647B2, 2020) and Rowe et al. (Handbook of pharmaceutical excipients, 6th edition, Pharmaceutical Press, 2009) as applied to claims 1-17, 22-26, and 31 above, and further in view of European Medicines Agency (Sodium laurilsulfate used as an excipient, EMA/CHMP/606830/2017, 2017).
Mao teaches triazolopyridines as JAK inhibitors while Rowe teaches excipients and application thereof.
They do not, however, teach the use of sodium dodecyl sulfate as a surfactant, the content being 0.1% to 5%, 1% to 3%, or 2% of the total weight.
European Medicines Agency addresses this deficiency by teaching that sodium laurilsulfate (sodium dodecyl sulfate) is an alkaline, anionic surfactant with a number of uses including as an emulsifying agent, modified-release agent, penetration enhancer, solubilizing agent, lubricant, and as a surfactant. In medicinal products, sodium laurilsulfate , has several listed uses along with associated concentrations including tablet lubricant (0.5% to 2 wt. %) and dissolution/wetting agent in solid oral dosage forms (0.2% to 1.5 wt. %). It is generally regarded as a safe excipient and included in the FDA inactive ingredients data base. A prima facie case of obviousness necessarily exists when the prior art range overlaps or touches a claimed range, such as in the instant rejection. MPEP § 2144.05. As such, it would have been prima facie obvious, to a person of ordinary skill in the art, to consider the of sodium dodecyl sulfate as a surfactant, to achieve the desired performance characteristics as described by the literature within the field of excipients, for the development of an oral composition appropriate for the delivery of JAK inhibitors in oral administration.
Claim 60 is rejected under 35 U.S.C. 103 as being unpatentable over Mao et al. ((1,2,4)triazolo(1,5-a)pyridine compound as JAK inhibitor and application thereof, AU2019326647B2, 2020) and Rowe et al. (Handbook of pharmaceutical excipients, 6th edition, Pharmaceutical Press, 2009) as applied to claims 1-17, 22-26, and 31 above, and further in view of Shi et al. (Pharmaceutical application of multivariate modelling techniques: a review on the manufacturing of tablets, RSC Adv. 2021, 11, 8323).
Mao teaches triazolopyridines as JAK inhibitors while Rowe teaches excipients and application thereof.
They do not, however, teach a preparation method selected from wet granulation, dry granulation process, and powder direct pressing process, and where the filler, disintegrant, adhesive, lubricant, or surfactant is added internally or externally.
Shi rectifies this by teaching an overviewed and nuanced look into continuous tablet manufacturing, exploring the multiple unit operation including mixing of excipients and active pharmaceutical ingredients, granulation and tableting, and applying a mathematical model to improve product quality and enhancing product and process understanding. Shi applies multivariate modeling techniques in tablet manufacturing to more thoroughly understand the three pathways, direction compaction, dry granulation, and wet granulation, to actively monitor the different processes, and quantify the model prediction against empirical parameters such as tablet quality. They utilize several techniques including transmission near infrared spectroscopy and Raman spectroscopy to study the manufacturing processes. As such, it would be prima facie obvious, to a person of ordinary skill in the art, to incorporate these different aspects of tablet manufacturing, including the use of listed categories of excipients, and the various operations including the blending process, granulation, and tablet compaction, to be able to produce a formulated JAK inhibitor tablet, for the development of an oral composition appropriate for the delivery in oral administration.
Allowable Subject Matter
Claims 51-52 and 56 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. The following is a statement of reasons for the indication of allowable subject matter: the crystal form of structure II as illustrated below, recited in claim 51, specified as forms A, B, C, D, were not taught in the prior art in a 100% embodiment.
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Claim 52, disclosing the XRPD characteristic peaks of crystal forms A, B, C, D of structure II, were not taught in the prior art in a 100% embodiment.
Claim 56, disclosing the XRPD diagrams of crystal forms A, B, C, D, of structure II, were not taught in the prior art in a 100% embodiment.
Conclusion
Claims 1-17, 22-26, 31-33, 38-39, 43, 47, 49, 60, and 62 are rejected under 35 U.S.C. 103. Claims 51-52 and 56 are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Allen Chao whose telephone number is (571)272-7001. The examiner can normally be reached Monday - Friday 0700-1300.
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/ALLEN CHAO/Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622