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
Status of the Claims
Claims 1-14 currently pending. Claims 1-14 are rejected.
Information Disclosure Statement
The Examiner has considered the Information Disclosure Statement(s) filed on 01/21/2026.
Response to Amendment/Arguments
The amendment filed 01/20/2026 is compliant with the requirements of 37 CFR 1.121(c), accordingly the amendment has been entered. Applicant’s arguments have been fully considered and are addressed below:
Objection to the Claims
The objection of the claim 7 for informalities has been overcome by the amendment correcting said informalities. The objection has been withdrawn.
35 USC § 112 Rejections
The rejection of claims 6, 8 and 12-14 under 35 USC 112 has been overcome by the amendments to said claims. The rejection has been withdrawn.
35 USC § 102 Rejection
Applicant's arguments regarding the rejection of claims 1-14 under 35 USC 102 for being anticipated by Gutcher et al. in WO 2018/146010 A1 have been fully considered but they are not persuasive.
Applicant argues that the prior art from Gutcher discloses undeuterated compounds that would be considered a genus and that “[an] invitation to investigate is not an inherent disclosure”, citing Metabolite Labs., Inc. v. Lab. Corp. of Am. Holdings, 370 F.3d 1354, 1367, 71 U.S.P.Q.2d 1081, 1091 (Fed. Cir. 2004), as the prior art reference merely invites further experimentation to find the species. Applicant also argues that the prior art does not identify a definite and limited class of deuterated analogs that would allow a person having ordinary skill in the art to “at once envisage each member of this limited class”, citing In re Petering, 301 F.2d at 681.
The instant case differs from the cited case law in that deuterium is inherently present in naturally occurring hydrogen. Though the prior art from Gutcher is silent regarding the presence of deuterium at at least one of the sites on the species, it is clear that a person having ordinary skill in the art would know that a non-zero percentage of hydrogen is in fact deuterium and that the prior art compound would inherently contain a deuterated hydrogen in either the R1 or R3 position as defined in the instant claims.
Applicant also argues that many patents have been granted claiming deuterated compounds despite the existence of non-deuterated versions in the literature, citing US Patent 8,524,733. There could be any number of reasons for patentability of deuterated compounds over their non-deuterated analogs. In the specific patent ‘733, for example, the independent claim 1 is drawn to a compound “wherein each position represented as D has deuterium enrichment of no less than about 90%”, far exceeding the natural abundance expected for deuterium as hydrogen:
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.
The rejection is maintained.
35 USC § 103 Rejection
Applicant's arguments regarding the rejection of claims 1-6 and 9-11 under 35 USC 103 for being obvious over Gutcher et al. in WO 2018/146010 A1 have been fully considered and are considered persuasive given unexpectedly superior results of the presently disclosed deuterated compounds. The rejection has been withdrawn.
Maintained Claim Rejection - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-14 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Gutcher et al. in WO 2018/146010 A1, published August 16, 2018.
Gutcher et al. teach Example 17,
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(see pg. 156, line 17), which is embraced by instant formula (I) of claim 1,
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, wherein:
R1 is a hydroxyl-substituted C3 alkyl (see instant claim 3);
R2, R5, R6, R8, R9 and R10 are each H;
R3 is C1 alkyl (see instant claim 5);
R7 is Cl (see instant claim 4); and
X is CR4 wherein R4 is H (see instant claim 2).
Example 17 from Gutcher et al. also anticipates the structures shown in claim 7, including the bottom 8 structures on page 6 and all structures on pages 7 and 8. The structure of the prior art differs in that the instant claims include a proviso that at least one of R1 and R3 is deuterium or substituted with a deuterium atom. However, deuterium has a non-zero natural abundance wherein “hydrogen” would embrace “deuterium.” This also applies to instant claim 6 wherein R13 and R14 are each independently deuterium.
Applicant is advised that numerous compounds are embraced by formula (I) of the instant claims noted above including, for instance, Examples 16-67 (pg. 155-194), 202 (p. 287), 204 (p. 288), 206 (p. 289), 210-211 (p. 290), 214-215 (p. 291-292), 218-219 (p. 293), 223 (p. 295), 227-228 (p. 296-297), 231 (p. 298), 236 (p. 300), 238-239 (p. 301) 245 (p. 303), 248 (p. 305), 256 (p. 308), 261 (p. 310), 262 (p. 310), 264 (p. 311), 267 (p. 312), 270 (p. 313), 272 (p. 313), 278 (p. 316), 289 (p. 320), 305-311 (p. 326-328), 315-317 (p. 330-331), 320 (p. 332), 324 (p. 335), and 335-336 (p. 340-341).
The prior art therefore anticipates instant claims 1-7.
Regarding claims 8 and 12-14, drawn to a method for preparing the compound, Gutcher et al. teach a method of preparing Example 17 wherein:
Intermediate 8, which has the structure
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(see page 66), and 4-hydrazino-1-methyl-1H-pyrazole dihydrochloride react in the presence of sodium acetate to form intermediate 9 which has the following structure:
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. See page 67, lines 1-15.
Intermediate 9 is dehydrogenated in the presence of copper dichloride to form intermediate 10, which has the following structure:
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. See page 67, lines 20 through page 68, line 4.
Intermediate 10 is hydrolyzed in the presence of lithium hydroxide to form intermediate 11, which has the following structure:
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. See page 68, lines 9-19.
Intermediate 11 and (2S)-2-aminopropan-1-ol react to form the final compound. See page 156, lines 14-19.
These synthetic steps of the prior art are identical to those of claim 8 as well as those of claim 12 wherein the first base is sodium acetate, claim 13 wherein the copper salt is CuCl2, and claim 14 wherein the second base is LiOH. Therefore, the prior art anticipates claim 8 and 12-14.
Regarding claim 9 drawn to a pharmaceutical composition comprising a compound of general formula (I) and a pharmaceutically acceptable carrier, Gutcher et al. state that the prior art compounds may be used “conventionally together with one or more pharmaceutically suitable excipient(s)”. See page 57, lines 27-29. Further, Example 17 referenced above was used in an in vivo assay measuring the efficacy of compositions comprising Example 17 and a PD-1/L-1 axis antagonist wherein the compound was dissolved in the carrier ethanol/solutol/water (10/40/50) before administration. See page 362, lines 6-30. Thus, claim 9 is anticipated by the prior art.
Regarding claims 10 and 11 drawn to a method for preventing and/or treating an AhR-mediated disease comprising administering either a compound of general formula (I) (per claim 10) or a pharmaceutical composition of claim 9 (per claim 11), the in vivo assay measuring the efficacy of compositions comprising Example 17 and a PD-1/L-1 axis antagonist anticipates the claims. Gutcher et al. teach that the claimed compound/composition was able to reduce the tumor size in mice that had been inoculated with B16F10-OVA mouse melanoma cells. See page 362, lines 6-30. Thus, claims 10-11 are anticipated by the prior art.
Conclusion
Claims 1-14 are rejected.
Applicant’s amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 extension fee 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 date of this final action.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jalisa H. Ferguson whose telephone number is (703)756-1489. The examiner can normally be reached Monday - Friday 9:00am - 5:00pm.
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/J.H.F./Examiner, Art Unit 1626
/KAMAL A SAEED/Primary Examiner, Art Unit 1626
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