Prosecution Insights
Last updated: April 19, 2026
Application No. 18/246,982

STABILIZED ALKYL NITRITE COMPOSITIONS

Final Rejection §103
Filed
Mar 28, 2023
Examiner
SONG, JIANFENG
Art Unit
1613
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Emergent Product Development Gaithersburg Inc.
OA Round
2 (Final)
56%
Grant Probability
Moderate
3-4
OA Rounds
2y 8m
To Grant
90%
With Interview

Examiner Intelligence

Grants 56% of resolved cases
56%
Career Allow Rate
468 granted / 834 resolved
-3.9% vs TC avg
Strong +33% interview lift
Without
With
+33.4%
Interview Lift
resolved cases with interview
Typical timeline
2y 8m
Avg Prosecution
77 currently pending
Career history
911
Total Applications
across all art units

Statute-Specific Performance

§101
0.7%
-39.3% vs TC avg
§103
48.2%
+8.2% vs TC avg
§102
8.2%
-31.8% vs TC avg
§112
18.1%
-21.9% vs TC avg
Black line = Tech Center average estimate • Based on career data from 834 resolved cases

Office Action

§103
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 . Withdrawn Rejections: Applicant's amendments and arguments filed on 12/19/2025 are acknowledged and have been fully considered. The Examiner has re-weighed all the evidence of record. Any rejection and/or objection not specifically addressed below is herein withdrawn. The following rejections and/or objections are either reiterated or newly applied. They constitute the complete set of rejections and/or objections presently being applied to the instant application. The application is examined in view of isoamyl nitrite as special alkyl nitrite and Vitamin K1 as special compound of formula I. Claims 1-11, 13-17, 26-28, 30-31 and 33 read on the elected species and are under examination. Claims 1-11, 13-17, 26-28, 30-31 and 33 are pending and under examination. 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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. Claims 1-11, 13-17, 26-28, 30-31 and 33 are rejected under 35 U.S.C. 103 as being unpatentable over Zhang et al. (US20190282536) in view of Dreher (US20140309173). Determination of the scope and content of the prior art (MPEP 2141.01) Zhang et al. teaches use of a nitric oxide releasing agent in preparing a medicament, wherein the medicament is used for preventing or treating EGFR inhibition associated epithelial diseases in a subject. The present application further provides a pharmaceutical composition or a kit comprising EGFR inhibitor and nitric oxide releasing agent (abstract). In some embodiments, the epithelial cell comprises skin epithelial cell, oral epithelial cell, stomach epithelial cell and/or small intestine epithelial cell ([0014]). In some embodiments, the nitric oxide releasing agent comprises organic molecule, wherein organic molecule comprises nitroglycerin, isosorbide mononitrate, butanediol mononitrate, pentaerythritol tetranitrate, isosorbide dinitrate, trolnitrate, nicorandil, nitro dihydroxyl methyl butanol, 5-amino-3-(4-morpholinyl)-1,2,3-oxadiazole, isoamyl nitrite ([0021]). In some embodiments, the drug is prepared for topical administration. In some embodiments. In some embodiments, the concentration of the nitric oxide releasing agent in the drug is from about 0.0001% (w/w) to about 50% (w/w). In some embodiments, the medicament is prepared as an ointment ([0029-0031]. In some embodiments, the EGFR-inhibition associated epithelial cell diseases may be classified into skin epithelial cell diseases (e.g., rash, acne, rosacea, atopic dermatitis, contact dermatitis, seborrheic dermatitis, lupus, scleroderma, pemphigus, pigmentation, black spot, leukoderma, urticaria, tinea corporis, the skin pruritus, alopecia, hair changes, erythema, paronychia and schizonychia, xerosis cuits, hypersensitivity and psoriasis) ([0117]). n some embodiments, the epithelial cell diseases may be skin epithelial cell diseases. In some embodiments, the skin epithelial cell diseases may be rash and pruritus ([0118]). The composition may comprises additional therapeutic agents. In some embodiments, the one or more additional therapeutic agents may be a medicament for treating epithelial diseases ([0165]). Medicaments for treating epithelial diseases may comprise anti-inflammatory agents, analgesics, local anesthetics, antihistamines, preservatives, immuosuppressors, antihemorrhagic agents and/or a mixture thereof ([0166]). Antihemorrhagic agents may comprise thrombin, vitamin Kl, protamine sulfate, aminocaproic acid, tranexamic acid, carbazochrome, sodium carbazochrome sulfonate, rutin and/or hesperidin ([0172]). In some embodiments, the medicament or the nitric oxide releasing agent of the present application may be used for topically oral administration ([0183]). The nitric oxide releasing agent as described in the present application may be administered in a manner well known in the art, e.g., by injection (e.g., subcutaneous, intraperitoneal, intraarticular, intraarterial, intrathecal, intrasternal, intrathecal, intralesional, intracranial, intramuscular, intracutaneous and intravenous injection or infusion) or non-injection (e.g., oral, nasal, sublingual, vaginal, rectal, or topical administration). The nitric oxide releasing agent as disclosed in the present application may be administered in a form of the pharmaceutical composition or kit of the present application ([0158]). Dreher teaches compositions of the invention to treat, alleviate, and/or ameliorate a symptom, condition, disorder, or disease of the skin or mucosa, wherein the symptom, condition, disorder, or disease is associated with changes in extracellular matrix components (abstract). Compositions according to the present invention were also studied for the treatment of other conditions, disorders and diseases where extracellular matrix components are altered including atopic dermatitis, eczema, scars and keloids, atrophie blanche, vulvar lichen sclerosus, epidermolysis bullosa, Ehlers-Danlos syndromes, and the Marfan syndrome ([0428]). The compositions of the present invention may contain one or more vitamins such as Vitamin K from about 0.0001% to about 25% or 0.001% to about 10% by weight ([0212]). In addition, the compositions according to the present invention may also be applied by topical, by injection, implantation, or subcutaneous placement ([0309-0310]). Ascertainment of the difference between the prior art and the claims (MPEP 2141.02) The difference between the instant application and Zhang et al. is that Zhang et al. do not expressly teach amount of Vitamin K1. This deficiency in Zhang et al. is cured by the teachings of Dreher. Finding of prima facie obviousness Rational and Motivation (MPEP 2142-2143) It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the invention of Zhang et al., as suggested by Dreher, and produce the instant invention. One of ordinary skill in the art would have been motivated to optimize and have the amount of Vitamin K1 from about 0.1% to about 20% (about 3% to about 18% or 10%) because this optimization under prior art condition or through routing experimentation. MPEP 2144.05. Under guidance from Dreher teaching about 0.001% to about 10% of vitamin K in a composition for treating skin disease, it is obvious for one of ordinary skill in the art to have the amount of Vitamin K1 from about 0.1% to about 20% (about 3% to about 18% or 10%) and produce instant claimed invention with reasonable expectation of success. Prior art teaches a composition comprising nitric oxide releasing agent isoamyl nitrite and epithelial diseases treating active Vitamin K1 at about 0.1% to about 20% (about 3% to about 18% or 10%). Regarding the limitation of wherein the composition comprising the alkyl nitrile has a purity after storage at 40C for six months, ranging from about 90% to about 95%, as measured by gas chromatography”, this is regarded as inherency of prior art composition. Since prior art teaches the same or substantially same composition, this same or substantially same composition is expected to have the same properties. MPEP 2112, "[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977). There is no requirement that a person of ordinary skill in the art would have recognized the inherent disclosure at the relevant time, but only that the subject matter is in fact inherent in the prior art reference. Schering Corp. v. Geneva Pharm. Inc., 339 F.3d 1373, 1377, 67 USPQ2d 1664, 1668 (Fed. Cir. 2003). Regarding claim 16, it is within skill of one artisan in the art to store the composition comprising unstable substance such as alkyl nitrile in ampule under inert gas. Regarding claim 33, since prior art composition is suitable for injection, it is suitable for autoinjector. In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, as evidenced by the references, especially in the absence of evidence to the contrary. Claims 1-11, 13-17, 26-28, 30-31 are rejected under 35 U.S.C. 103 as being unpatentable over Friedman et al. (US20050271596) in view of Dreher (US20140309173). Determination of the scope and content of the prior art (MPEP 2141.01) Friedman et al. teaches a foamable composition including: a vasoactive agent; at least one organic carrier selected from the group consisting of a hydrophobic organic carrier, an organic polar solvent, an emollient and mixtures thereof (abstract; claim 31 and 39). The composition further comprises additional therapeutic agent such as Vitamin K (claim 34). The composition is useful for treating skin disease such as dermatose, a dermatitis (claim 39). Example of vasoactive agent includes amyl nitrite, butyl nitrite and isobutyl nitrite ([0058]). Dreher teaches compositions of the invention to treat, alleviate, and/or ameliorate a symptom, condition, disorder, or disease of the skin or mucosa, wherein the symptom, condition, disorder, or disease is associated with changes in extracellular matrix components (abstract). Compositions according to the present invention were also studied for the treatment of other conditions, disorders and diseases where extracellular matrix components are altered including atopic dermatitis, eczema, scars and keloids, atrophie blanche, vulvar lichen sclerosus, epidermolysis bullosa, Ehlers-Danlos syndromes, and the Marfan syndrome ([0428]). The compositions of the present invention may contain one or more vitamins such as Vitamin K from about 0.0001% to about 25% or 0.001% to about 10% by weight ([0212]). In addition, the compositions according to the present invention may also be applied by topical, by injection, implantation, or subcutaneous placement ([0309-0310]). Ascertainment of the difference between the prior art and the claims (MPEP 2141.02) The difference between the instant application and Friedman et al. is that Friedman et al. do not expressly teach amount of Vitamin K1. This deficiency in Friedman et al. is cured by the teachings of Dreher. Finding of prima facie obviousness Rational and Motivation (MPEP 2142-2143) It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the invention of Friedman et al., as suggested by Dreher, and produce the instant invention. Friedman et al. teaches a composition comprising amyl nitrile and vitamin K. Since Vitamin K1 is one of only three major Vitamin K, it is obvious to have vitamin K1 in the composition because of limited choice. One of ordinary skill in the art would have been motivated to optimize and have the amount of Vitamin K1 from about 0.1% to about 20% (about 3% to about 18% or 10%) because this optimization under prior art condition or through routing experimentation. MPEP 2144.05. Under guidance from Dreher teaching about 0.001% to about 10% of vitamin K in a composition for treating skin disease, it is obvious for one of ordinary skill in the art to have the amount of Vitamin K1 from about 0.1% to about 20% (about 3% to about 18% or 10%) and produce instant claimed invention with reasonable expectation of success. One of ordinary skill in the art would have been motivated to replace isoamyl nitrite for amyl nitrite in the composition because isoamyl nitrite is positional isomer of amyl nitrite. MPEP 2144.09, A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). Therefore, it is obvious to replace isoamyl nitrite for amyl nitrite in the composition and produce instant claimed invention with reasonable expectation of success. Thus, it is obvious to have a composition comprising nitric oxide releasing agent isoamyl nitrite and epithelial diseases treating active Vitamin K1 at about 0.1% to about 20% (about 3% to about 18% or 10%). Regarding the limitation of wherein the composition comprising the alkyl nitrile has a purity after storage at 40C for six months, ranging from about 90% to about 95%, as measured by gas chromatography”, this is regarded as inherency of prior art composition. Since prior art teaches the same or substantially same composition, this same or substantially same composition is expected to have the same properties. MPEP 2112, "[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977). There is no requirement that a person of ordinary skill in the art would have recognized the inherent disclosure at the relevant time, but only that the subject matter is in fact inherent in the prior art reference. Schering Corp. v. Geneva Pharm. Inc., 339 F.3d 1373, 1377, 67 USPQ2d 1664, 1668 (Fed. Cir. 2003). Regarding claim 16, it is within skill of one artisan in the art to store the composition comprising unstable substance such as alkyl nitrile in ampule under inert gas. In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, as evidenced by the references, especially in the absence of evidence to the contrary. Response to Argument: Applicants argued that there is no teaching to select vitamin K1 and there is no teaching vitamin K1 as stabilizing agent. In response to this argument: this is not persuasive. Prior art teaches vitamin K1 among other active agents, each active agent including vitamin K1 is obvious no matter how many other active agents are recited because the recitation of other active agents does not make any particular active agent including vitamin K1 less obvious. Regarding there is no teaching vitamin K1 as stabilizing agent, it is agued that "[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977). There is no requirement that a person of ordinary skill in the art would have recognized the inherent disclosure at the relevant time, but only that the subject matter is in fact inherent in the prior art reference. Schering Corp. v. Geneva Pharm. Inc., 339 F.3d 1373, 1377, 67 USPQ2d 1664, 1668 (Fed. Cir. 2003). Therefore, the 103 rejection is still proper. Applicants argue about results from example 1. In response to this argument: this is not persuasive. It appears that applicants only has good stability after 6M for 10% of vitamin K1, and this data is not sufficient to overcome the 103 rejection at least for the following reasons. Firstly, applicants failed to compare with closest prior art, for example, composition comprising other active such as rutin (different from Vitamin K1). Secondly, the results are not commensurate with scope of claimed invention that having broad range of vitamin K1 (1-20%). Furthermore, applicants only have data for vitamin K1, and not data for other compound of formula I. Therefore, the 103 rejection is still proper. MPEP 2141 III states: “The proper analysis is whether the claimed invention would have been obvious to one of ordinary skill in the art after consideration of all the facts.” Respectfully, after weighing all the evidence, the Examiner has reached a determination that the instant claims are not patentable in view of the preponderance of evidence and consideration of all the facts which is more convincing than the evidence which has been offered in opposition to it. Conclusion No claim is allowed. THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a). 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. Any inquiry concerning this communication or earlier communications from the examiner should be directed to JIANFENG SONG. Ph.D. whose telephone number is (571)270-1978. The examiner can normally be reached M-F 8-5. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Brian-Yong Kwon can be reached at (571)272-0581. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /JIANFENG SONG/Primary Examiner, Art Unit 1613
Read full office action

Prosecution Timeline

Mar 28, 2023
Application Filed
Sep 30, 2025
Non-Final Rejection — §103
Dec 19, 2025
Response Filed
Feb 18, 2026
Final Rejection — §103 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

3-4
Expected OA Rounds
56%
Grant Probability
90%
With Interview (+33.4%)
2y 8m
Median Time to Grant
Moderate
PTA Risk
Based on 834 resolved cases by this examiner. Grant probability derived from career allow rate.

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