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 .
Status of the Claims
Claims 21-24 and 26-40 are pending. Claims 31-40 are withdrawn as being directed to a nonelected invention. Acknowledgment is made of the amendment of claims 21, 23, 26, and 33 and the cancellation of claim 25 in the reply filed 03/05/2026.
Election/Restriction Requirement
Applicant elected without traverse Group I, claims 21-24 and 26-30, in the reply filed 10/17/2025. Applicant elected the species naltrexone decanoate as the ester of naltrexone, decanoyl chloride as the acylating agent, triethyl amine as the organic base, DCM as the organic solvent, and oxalic acid as the acid. Examination will be limited to the above listed embodiments and any embodiments discovered in the prior art search.
Claims 31-40 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 10/17/2025.
Withdrawn Rejections
Applicant’s amendment to the claims, filed 03/05/2026, overcomes the rejection of claims 21, 23, and 25-30 under 35 U.S.C. 102(a)(1) as being anticipated by, and claims 22 and 24 under 35 U.S.C. 103 as being unpatentable over, Lu (CN 1050130 C). Lu does not teach or suggest that the reactions can be performed in 20-30 minutes at 0-5 ºC. The rejection of claims 21-30 has been withdrawn.
Applicant’s amendment to the claims, filed 03/05/2026, overcomes the rejection of claims 21-23, and 25-30 under 35 U.S.C. 102(a)(1) as being anticipated by, and claim 24 under 35 U.S.C. 103 as being unpatentable over, Tusche et al. (US 20190308989 A1). Tusche et al. does not teach or suggest that the reactions can be performed in 20-30 minutes at 0-5 ºC. The rejection of claims 21-30 has been withdrawn.
Maintained Objections
Claim Objections
Claim 23 is objected to because of the following informalities:
Claim 23 reads “…the group consisting of a non-polar organic solvent…; a polar organic solvent…”. This should be corrected to read either “…the group consisting of a non-polar organic solvent…; and a polar organic solvent…” or “…the group consisting of a non-polar organic solvent…; or a polar organic solvent…” (emphasis added).
Appropriate correction is required.
New Rejections
Necessitated by Claim Amendment
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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 21-24 and 26-30 are rejected under 35 U.S.C. 103 as being unpatentable over Romanov (RU 2215742 C1), cited by Applicant in the IDS, English translation provided.
Romanov teaches, on page 3 of the English translation, a method of synthesizing an ester of naltrexone, wherein the ester comprises saturated or unsaturated C2-18 alkyl. The reactions are taught to be run in toluene, methylene chloride, THF, or 1,2-dimethoxyethane, and carried out in presence of an acid acceptor such as an alkali metal carbonate or bicarbonate, or a tertiary amine such as pyrrolidinopyridine, 4-dimethylaminopyridine, or triethylamine. It is taught on pages 5-6 that the acylating agent is reacted with N-substituted 14-hydroxymorphinans at 0 ºC. In Example 1, the reaction of tridecanoic acid chloride and naloxone hydrochloride is run for 2 hours in methylene chloride. Romanov teaches, on page 5 of the English translation, that the compounds are stable in air during storage and were obtained in a short time with yields of 97.6-98.5%.
Example 3, in Tables 1 and 2, teaches the reaction of naltrexone with heptanoyl chloride in methylene chloride, with the base sodium bicarbonate, to produce naltrexone heptanoate. Example 8, in Tables 1 and 2, teaches the reaction of naltrexone with decanoyl chloride in 1,2-dichloroethane, with the base sodium carbonate, to produce naltrexone decanoate.
Romanov fails to teach that the reaction time is 20-30 minutes rather than 2 hours as shown in the examples. Romanov fails to teach that the reaction is carried out in cyclopentyl methyl ether as in instant claim 24.
However, MPEP 2144.05 II states: "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) …It is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions."). See also KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 416, 82 USPQ2d 1385, 1395 (2007). Additionally, MPEP 2144.06 II, which discusses substituting equivalents known for the same purpose, states: “An express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982).”
Therefore, changing the reaction time of a known reaction, where all other conditions are taught to be the same in the prior art, would be considered routine optimization. Additionally, substituting one solvent for another in a known reaction, in order to carry out the same reaction as taught in the prior art, would be prima facie obvious to one of ordinary skill in the art.
It is routine optimization to determine the best solvent and reaction time for carrying out a reaction, and one of ordinary skill in the art would have a reasonable expectation of success in testing different solvents and reaction times.
Conclusion
Claims 21-24 and 26-30 are rejected.
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.
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/R.M.S./Examiner, Art Unit 1624
/JEFFREY H MURRAY/Supervisory Patent Examiner, Art Unit 1624
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