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 .
Election/Restrictions
Applicant's election with traverse of Group I, claims 41-49 and 53-55, drawn to a compound having the structure of Formula VI and a pharmaceutical compositing comprising the compound; and a compound 48 having the structure of:
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as the elected compound species of Formula VI in the reply filed on December 1, 2025 is acknowledged. The traversal is on the ground(s) that (i) the cited prior art does not teach the X’ moiety of Formula VI and Formula XII, which should be considered as part of the technical feature share between the groups of inventions. Applicant further argues (ii) the product and the method of use clearly related to each other and there is minimal search burden between Group I and II, and Group II and IV. The first argument is found persuasive; however, technical feature shared among the group of species still lack unity of invention in view of the prior art rejections set forth below. The second argument with respect to search burden is not found persuasive, because search burden is not a requirement for unity of invention. In fact, search burden is one of the standards for U.S. restriction practice.
Claims 50-52 and 56-70 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on December 1, 2025.
Claim 47 is withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected species, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on December 1, 2025.
Please note applicant indicated that claims 41-49 and 53-61 encompass the elected compound species of Formula VI; However, the examiner determined claim 47 is drawn to a compound species non-elected.
Expansion of Election of Species Requirement
A reasonable and comprehensive search of the elected species conducted by the Examiner determined that the prior art at the time of the present invention was such that it did not anticipate or render obvious the elected species:
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. In light of this discovery, the search is expanded to the subject matter of the subgenus of the elected species, i.e., the compound of Formula VI having the structure of:
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,
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,
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, and
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, such that it does not encompass the full scope of the claims.
Status of the Claims
Claims 41-70 are pending. Claims 47, 50-53 and 56-70 are withdrawn.
Claims 41-46, 48-49 and 53-55 are under examination in accordance with the elected compound species along with the expanded compound species sets forth in the Expansion of Election of Species Requirement section above.
Priority
The instant application 18/266,936 filed on June 13, 2023 is a 371 of PCT/CN2022/074975 filed
on January 29, 2022, which claims priority to, and the benefits of U.S. Provisional Application No.
63/144,322 filed on February 1, 2021.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on June 13, 2023 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 § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 41-46, 48-49 and 53-55 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding to claim 41, where applicant acts as his or her own lexicographer to specifically define a term of a claim contrary to its ordinary meaning, the written description must clearly redefine the claim term and set forth the uncommon definition so as to put one reasonably skilled in the art on notice that the applicant intended to so redefine that claim term. Process Control Corp. v. HydReclaim Corp., 190 F.3d 1350, 1357, 52 USPQ2d 1029, 1033 (Fed. Cir. 1999). In the present case, the term “C3-C30 polycycloalkyl” is used by the claim to mean “non-aromatic polycyclic ring containing 3-30 carbon atoms in the ring structure,” while the accepted meaning for polycyclic is “having two or more rings in the molecule”, and cycloalkyl is “any univalent radical (as cyclohexyl) formed by removal of one hydrogen atom from a cycloalkane” according to Merriam-Webster Dictionary. In other words, based on the general accepted meaning of polycycloalkyl, a 3-carbon-member polycyclic ring does not exist because the minimum number of carbon atoms required to form a single closed, saturated ring is three, thus, cannot form a polycyclic ring. Accordingly, the term is indefinite because the specification does not clearly redefine the term. Claims 42-46, 48-49 and 53-55 are rejected based on their dependency on a rejected base claim.
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:
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.
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 41-44, 48 and 53-55 are rejected under 35 U.S.C. 103 as being unpatentable over Amewu et al. (US 2013/0023551 A1), in view of Patani et al. (Chem. Rev., 1996. Vol. 96, 8: 3147-3176).
Amewu et al. teaches a compound 27g, N-(2-Diethylamino-ethyl)-2-(7,8,15,16-tetraoxa-dispiro[5.2.5.2]-hexadec-3-yl)-acetamide, having the structure of:
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(see e.g., [0185]) is an exemplary compound of formula (I) useful for the treatment of malaria and/or cancer (see e.g., [0002]). Amewu et al. further teaches a pharmaceutical composition comprising a therapeutically effective amount of the compound of the invention and, preferably, a pharmaceutically acceptable vehicle (see e.g., [0079]). Amewu et al. further teaches a pharmaceutical composition for the treatment of a cancer comprising the compound and a pharmaceutically acceptable excipient (see e.g., [0056]). Amewu et al. further teaches compound having the formula (I)
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, wherein ring A represents a substituted or unsubstituted monocyclic or multicyclic ring (see e.g., [0008]). Amewu et al. further teaches when any of the foregoing substituents are designated as being optionally substituted, the substituent groups which are optionally present may be any one or more of those customarily employed in the development of pharmaceutical compounds and/or the modification of such compounds to influence their structure/activity, stability, bioavailability or other property; specific examples of such substituents include, inter alia, alkyl (see e.g., [0069]).
Amewu et al. does not teach the compound having the structure of Formula VI.
Patani et al. teaches bioisosterism represents one approach used by the medicinal chemist for
the rational modification of lead compounds into safer and more clinically effective agents (see e.g.,
“introduction” section on p. 3147). Patani et al. further teaches a group of bioisosteres elicit similar
biological activity, and have been classified as either classical or nonclassical, wherein the classical
bioisosteres are a series of replacements defined by Grimm’s Hydride Displacement Law and
Erlenmeyer’s definition of isosteres (see e.g., p. 3148-3149). Patani et al. further teaches classical bioisosteres includes divalent isosteres that can be classified into two subgroups, including those divalent isosteres where substitution of a different atom results in the alternation of two single bonds such as in the series: C-C-C, C-NH-C, C-O-C, and C-S-C (see e.g., p. 3155, left column, “B. Divalent Isosteres” section, 1st paragraph). Patani et al. further teaches the divalent replacements involving two singles bonds shown below:
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, and teaches that the use of an oxygen atom as a bioisotereic linker, which has a marginally smaller bond angle and much greater electronegativity, results in an analogue with increased potency (see e.g., p. 3156, right column, 1st paragraph; Figure 24; Table 20).
In the instant case, the difference between the compound 27g of Amewu et al. and the claimed compound of Formula VI is that the prior art compound contains methylene group (-CH2-) proceeding the amide group rather than an oxygen atom shown below (see shaded):
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.
It would have been prima facie obvious to one of ordinary skill in the art at the time the application was filed to select the compound 27g of Amewu et al., and then modify said compound by replacing the -CH2- in between the cyclohexyl ring and the amide group with an oxygen atom based on the classical bioisosteres taught by Patani et al. to arrive at the claimed invention. One would have been motivated to do so, because Patani et al. teaches -CH2- and -O- are divalent isosteres that can be interchanged in medicinal chemistry to arrive compound with similar properties. One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that the compound 27g of Amewu et al. modified in accordance with the divalent isosteres taught by Patani et al. would have successfully demonstrate similar activity against cancer or malaria; and therefore, said modified compound at a therapeutically effective amount can successfully be incorporated with a pharmaceutically acceptable excipient to arrive at a pharmaceutical composition without any appreciable loss of activity. Please note the modified compound 27g of Amewu et al. in view of Patani et al. sets forth above is a compound having the structure of Formula VI
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, wherein A’ is
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; a is 1; Z’ is hydrogen; X’ is O; R5 is hydrogen; R8 is
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(substituted alkyl, wherein the substituents are independently an amino; and
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, wherein i is 2; R18 is hydrogen; R19 and R20 are independently a unsubstituted alkyl); and a compound having the structure of Formula VIII
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, wherein a is 1; a’ is 1; Z’ is hydrogen; X’ is O; R5 is hydrogen; R8 is
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(substituted alkyl, wherein the substituents are independently an amino); e is 0.
Regarding the limitation of “further comprising a second active agent” in claim 54, and the limitation of “wherein the second active agent is an anticancer agent” in claim 55, it would have been prima facie obvious to a person of ordinary skill in the art at the time the application was filed to combine the pharmaceutical composition of Amewu et al. and Patani et al. sets forth above with the compound 27g taught by Amewu et al. to arrive at the claimed invention. One would have been motivated to do so, because compound 27g of Amewu et al. is taught to be useful for the same purpose (the treatment of cancer or malaria). One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that by combining compounds that are useful separately for the same purpose (the treatment of cancer or malaria) would expected to be similarly useful when used together. See In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980).
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the time the application was filed, absent factual evidence to the contrary.
Claims 41-46, 48 and 53-55 are rejected under 35 U.S.C. 103 as being unpatentable over Amewu et al. (US 2013/0023551 A1), in view of Patani et al. (Chem. Rev., 1996. Vol. 96, 8: 3147-3176) as applied to claims 41-44, 48 and 53-55 above, and further in view of Renslo et al. (US 10,662,215 B2).
The teachings of Amewu et al. and Patani et al. are sets forth above and applied as before.
Amewu et al. and Patani et al. does not teach the limitations of R10 as claimed in claims 45-46.
Renslo et al. teaches exemplary compound of formula (Ia) includes compound of Example 23 having the structure of:
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(see e.g., Table 1, Example 23).
Renslo et al. further teaches compounds of formula (Ia):
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are compounds of formula (I) useful for treating a disease, including cancer and malaria (see e.g., Col. 106, line 11-49; Col. 111, line 10-13, 18-19 and 24-25), wherein Ring A is a substituted or unsubstituted cycloalkylene or substituted or unsubstituted heterocycloalkylene (see e.g., Col 64, line 14-35). Renslo et al. further teaches in some embodiments, L1 is a bond (see e.g., Col. 65, line 60-61). Renslo et al. further teaches in some embodiments, R1 is unsubstituted C1-C4 alkyl (see e.g., Col. 72, line 51-52). Renslo et al. further teaches the term “alkyl” means a straight or branched non-cyclic carbon chain, or combination thereof; and examples of saturated hydrocarbon radicals include groups, such as t-butyl (see e.g., Col. 5, line 9-18).
Regarding the limitations recited in claims 45-46, the difference between the modified compound 27g of Amewu et al. in view of Patani et al. sets forth above and the claimed compound is that the ring A (cyclohexane) of said modified compound is unsubstituted. It would have been prima facie to one of ordinary skill in the art at the time the application was filed to further modify the modified compound 27g of Amewu et al. in view of Patani et al. by substituting the ring A (cyclohexane) with t-butyl as the unsubstituted C1-C4 alkyl. One would have been motivated to do so, because Amewu et al. teaches the ring A of formula (I) can be substituted with a list of substituents, including alkyl; and Renslo et al. teaches the compounds of formula (Ia) with close structural similarities, and further teaches the ring A of formula (Ia) can be substituted with an unsubstituted C1-C4 alkyl, such as t-butyl to arrive at a compound useful for the same purpose of treating cancer or malaria. One of ordinary skill in the art would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonbly expected that the ring A (cyclohexane) of the modified compound 27g of Amewu et al. in view of Patani et al. substitued with a t-butyl as the alkyl would have sucessfully arrive at a compound that is similiarly useful for the treatment of cancer or malaria.
Claims 41-44, and 53-55 are rejected under 35 U.S.C. 103 as being unpatentable over Amewu et al. (US 2013/0023551 A1), in view of Patani et al. (Chem. Rev., 1996. Vol. 96, 8: 3147-3176).
Amewu et al. teaches a compound 27h, 1-Morpholin-4-yl-2-(7,8,15,16-tetraoxa-dispiro[5.2.
5.2]hexadec-3-yl)-ethanone, having the structure of:
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(see e.g., [0395]) and compound 29l having the structure of
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(see e.g., [0221]) are exemplary compounds of formula (I) useful for the treatment of malaria and/or cancer (see e.g., [0002]). Amewu et al. further teaches a pharmaceutical composition comprising a therapeutically effective amount of the compound of the invention and, preferably, a pharmaceutically acceptable vehicle (see e.g., [0079]). Amewu et al. further teaches a pharmaceutical composition for the treatment of a cancer comprising the compound and a pharmaceutically acceptable excipient (see e.g., [0056]). Amewu et al. further teaches compound having the formula (I)
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, wherein ring A represents a substituted or unsubstituted monocyclic or multicyclic ring; wherein Y is, inter alia, -C(O)NR1R2, where R1 and R2 are linked so as to form part of a substituted or unsubstituted heterocyclic ring (see e.g., [0008]-[0009]). Amewu et al. further teaches when any of the foregoing substituents are designated as being optionally substituted, the substituent groups which are optionally present may be any one or more of those customarily employed in the development of pharmaceutical compounds and/or the modification of such compounds to influence their structure/activity, stability, bioavailability or other property; specific examples of such substituents include, inter alia, alkyl (see e.g., [0069]).
Amewu et al. does not teach the compound having the structure of Formula VI.
Patani et al. teaches bioisosterism represents one approach used by the medicinal chemist for
the rational modification of lead compounds into safer and more clinically effective agents (see e.g.,
“introduction” section on p. 3147). Patani et al. further teaches a group of bioisosteres elicit similar
biological activity, and have been classified as either classical or nonclassical, wherein the classical
bioisosteres are a series of replacements defined by Grimm’s Hydride Displacement Law and
Erlenmeyer’s definition of isosteres (see e.g., p. 3148-3149). Patani et al. further teaches classical bioisosteres includes divalent isosteres that can be classified into two subgroups, including those divalent isosteres where substitution of a different atom results in the alternation of two single bonds such as in the series: C-C-C, C-NH-C, C-O-C, and C-S-C (see e.g., p. 3155, left column, “B. Divalent Isosteres” section, 1st paragraph). Patani et al. further teaches the divalent replacements involving two singles bonds shown below:
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, and teaches that the use of an oxygen atom as a bioisotereic linker, which has a marginally smaller bond angle and much greater electronegativity, results in an analogue with increased potency (see e.g., p. 3156, right column, 1st paragraph; Figure 24; Table 20).
In the instant case, the difference between the compound 27h of Amewu et al. and the claimed compound of Formula VI is that the prior art compound contains methylene group (-CH2-) proceeding the amide group rather than an oxygen atom shown below (see shaded):
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. It would have been prima facie obvious to one of ordinary skill in the art at the time the application was filed to select the compound 27h of Amewu et al., and then modify said compound by replacing the -CH2- in between the cyclohexyl ring and the amide group with an oxygen atom based on the classical bioisosteres taught by Patani et al. to arrive at the claimed invention. One would have been motivated to do so, because Patani et al. teaches -CH2- and -O- are divalent isosteres that can be interchanged in medicinal chemistry to arrive compound with similar properties. One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that the compound 27h of Amewu et al. modified in accordance with the divalent isosteres taught by Patani et al. would have successfully demonstrate similar activity against cancer or malaria; and therefore, said modified compound at a therapeutically effective amount can successfully be incorporated with a pharmaceutically acceptable excipient to arrive at a pharmaceutical composition without any appreciable loss of activity. Please note the modified compound 27h of Amewu et al. in view of Patani et al. sets forth above is a compound having the structure of Formula VI
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, wherein A’ is
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; a is 1; Z’ is hydrogen; X’ is O; R5 and R8 are taken together with the nitrogen to form
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; and a compound having the structure of Formula VIII
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, wherein a is 1; a’ is 1; Z’ is hydrogen; X’ is O; R5 and R8 are taken together with the nitrogen to form
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; e is 0.
Regarding the limitation of “further comprising a second active agent” in claim 54, and the limitation of “wherein the second active agent is an anticancer agent” in claim 55, it would have been prima facie obvious to a person of ordinary skill in the art at the time the application was filed to combine the pharmaceutical composition of Amewu et al. and Patani et al. sets forth above with the compound 27h taught by Amewu et al. to arrive at the claimed invention. One would have been motivated to do so, because compound 27h of Amewu et al. is taught to be useful for the same purpose (the treatment of cancer or malaria). One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that by combining compounds that are useful separately for the same purpose (the treatment of cancer or malaria) would expected to be similarly useful when used together. See In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980).
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the time the application was filed, absent factual evidence to the contrary.
Claims 41-44, 49, and 53-55 are rejected under 35 U.S.C. 103 as being unpatentable over Amewu et al. (US 2013/0023551 A1), in view of Patani et al. (Chem. Rev., 1996. Vol. 96, 8: 3147-3176) as applied to claims 41-44, and 53-55 above, and further in view of Renslo et al. (US 10,662,215 B2).
The teachings of Amewu et al. and Patani et al. are sets forth above and applied as before.
Amewu et al. and Patani et al. does not teach the compound as recited in claim 49.
Renslo et al. teaches exemplary compound of formula (Ia) includes compound of Example 23 having the structure of:
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(see e.g., Table 1, Example 23).
Renslo et al. further teaches compounds of formula (Ia):
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are compounds of formula (I) useful for treating a disease, including cancer and malaria (see e.g., Col. 106, line 11-49; Col. 111, line 10-13, 18-19 and 24-25), wherein Ring A is a substituted or unsubstituted cycloalkylene or substituted or unsubstituted heterocycloalkylene (see e.g., Col 64, line 14-35). Renslo et al. further teaches in some embodiments, L1 is a bond (see e.g., Col. 65, line 60-61). Renslo et al. further teaches in some embodiments, R1 is unsubstituted C1-C4 alkyl (see e.g., Col. 72, line 51-52). Renslo et al. further teaches the term “alkyl” means a straight or branched non-cyclic carbon chain, or combination thereof; and examples of saturated hydrocarbon radicals include groups, such as t-butyl (see e.g., Col. 5, line 9-18).
Regarding the limitation recited in claim 49, the difference between the modified compound 27 of Amewu et al. in view of Patani et al. sets forth above and the expanded compound species instantly claimed is that the ring A (cyclohexane) of said modified compound is unsubstituted, and said modified compound contains the morpholine ring rather than a piperazine ring shown below (see shaded):
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. It would have been prima facie to one of ordinary skill in the art at the time the application was filed to further modify the modified compound 27h of Amewu et al. in view of Patani et al. sets forth above by substituting the ring A (cyclohexane) with t-butyl as the unsubstituted C1-C4 alkyl; and then substituting the morpholine ring with a piperazine ring at the Y moiety of Formula I taught by Amewu et al. One would have been motivated to do so, because Amewu et al. teaches the ring A of formula (I) can be substituted with a list of substituents, including alkyl, and further teaches R1 and R2 together can form a heterocyclic ring that is substituted or unsubstituted by exemplifying compounds having the structure of:
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and
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; and Renslo et al. teaches the compounds of formula (Ia) with close structural similarities, and further teaches the ring A of formula (Ia) can be substituted with an unsubstituted C1-C4 alkyl, such as t-butyl to arrive at a compound useful for the same purpose of treating cancer or malaria. One of ordinary skill in the art would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonbly expected that the modified compound 27h of Amewu et al. in view of Patani et al. substitued with a t-butyl as the alkyl at the Ring A (cyclohexane), and then replacing the morpholine ring with a piperazine as the unsubstituted heterocyclic ring would have sucessfully arrive at a compound that is similiarly useful for the treatment of cancer or malaria.
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the time the application was filed, absent factual evidence to the contrary.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Chihyi Lee whose telephone number is (571)270-0663. The examiner can normally be reached Monday - Friday 8:30 am - 5:00 pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy L. Clark can be reached at (571) 272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/CHIHYI LEE/Examiner, Art Unit 1628 /JEAN P CORNET/Primary Examiner, Art Unit 1628