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 .
This is the first action on the merits.
Claims 1-15, 18 and 19 are pending and claims 1-9, 18 and 19 are under examination. Claims 10-15 are withdrawn based on the unity of invention.
Election/Restrictions
Applicant's election without traverse of Group I in the reply filed on October 30, 2025 is acknowledged. Group I, drawn to a process for preparing trenbolone acetate, embraced by claims 1-9, 18 and 19 was elected by Applicant. Applicant has not pointed to any errors in the Examiner’s analysis of the different inventions. The requirement is still deemed proper and is therefore made FINAL.
Claim Objections
Claim 19 is objected to because of the following informalities: the phrase, “the steps are carried out one-pot.” should be replaced with “the previous step is carried out in one-pot.” Appropriate correction is required.
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 3, 4, 7, 8, 18 and 19 is 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 pre-AIA the applicant regards as the invention.
Claims 3, 7 and 8 lack antecedent basis for the phrase “the particle size distribution in the range.”
To overcome the rejection, the phrase may be amended to “of a particle size distribution.”
In claim 4, the phrase, “in the range” lacks antecedent basis in two places.
To overcome the rejection, the phrase may be amended to “in a range.”
In claim 8, the phrase, “the obtained Trenbolone Acetate of formula (I) having” lacks antecedent basis.
To overcome the rejection, the phrase may be amended to “the Trenbolone Acetate of formula (I) obtained has.”
Claim 18 lacks antecedent basis regarding the phrase “the previous step,” see line 2.
To overcome the rejection, the phrase may be amended to “a step.”
Claim 19 is drawn to the process of claim 18 carried out in one-pot, which is vague. Since there is only one step in claim 18, the process would be in one-pot. Thus, said claim is vague.
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 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.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103(a) which forms the basis for all obviousness rejections set forth in this Office action:
(a) A patent may not be obtained though the invention is not identically disclosed or described as set forth in section 102 of this title, if the differences between the subject matter sought to be patented and the prior art are such that the subject matter as a whole would have been obvious at the time the invention was made to a person having ordinary skill in the art to which said subject matter pertains. Patentability shall not be negatived 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(a) 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 under 35 U.S.C. 103(a), the examiner presumes that the subject matter of the various claims was commonly owned at the time any inventions covered therein were made absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and invention dates of each claim that was not commonly owned at the time a later invention was made in order for the examiner to consider the applicability of 35 U.S.C. 103(c) and potential 35 U.S.C. 102(e), (f) or (g) prior art under 35 U.S.C. 103(a).
Claims 1-9, 18 and 19 are rejected under AIA 35 U.S.C. 103(a) as being unpatentable over Roussel UCLAF (GB 1035683, cited on the IDS) in view of Hardwood et al. ((Experimental Organic Chemistry, Standard and Microscale, 2nd Edition, 1998, pp. 131-143), and Johnson et al. (WO 2007106768, cited on the IDS).
The present application claims a process of making trenbolone acetate comprising crystallizing trenbolone acetate with a C2-C5 alkyl alcohol (see claim 2 for isopropanol) or a mixture thereof. Claim 3 introduces a seeding step for the crystallization to obtain a particular crystal shape and size as noted in the dependent claims.
The ‘683 patent teaches a crystallization of trenbolone acetate utilizing isopropyl ether and hexane, see Example 3, page 7, left-hand column, lines 66-67. The reference further teaches that the compound is soluble in alcohol, see page 7, left-hand column, line 74. The ‘683 patent does not prepare trenbolone acetate in an C2-C5 alkyl alcohol or a mixture thereof.
Crystallizations are considered routine and conventional for isolating and/or purifying organic compounds as these techniques are taught in organic classes and textbooks, see the Hardwood reference, that provides guidance for determining solvents (including anti-solvents), temperatures, seeding, etc. Accordingly, this type of modification would have been well within the purview of the skilled artisan, unless there is evidence to the contrary.
Johnson et al. teach, “[A] process, for the production of crystalline particles of an active organic compound The process includes the steps of generating a micro-seed by a wet-milling process and subjecting the micro-seed to a crystallization process. The resulting crystalline particles have a mean particle size of less than about 100 μm. The present invention also provides for a pharmaceutical composition which includes the crystalline particles produced by the method described herein and a pharmaceutically acceptable carrier.,” see abstract. The further teaches, “In an effort to control the morphologic properties of the final product, it is a trend in One particle engineering to use seed particles of the product to provide a template for crystal growth during crystallization. Seeding can help control the particle size, crystal form, and chemical purity by limiting the supersaturation,” see page 3, paragraph [0007]. The reference teaches the seeding technique in claim 3 to obtain the claimed particle sizes.
Claim 9 is drawn to a specific crystal structure of irregular hexagon plates. The ‘683 patent is silent on the type of crystal produced during the crystallization. However, following the procedure in the Johnson publication, a person skilled in art would inherently obtain the specific crystal structure as claimed.
The ‘683 patent teaches the step found in claim 18 that converts the OH-steroid to the acetyl ester steroid of trenbolone acetate and the reaction is done in one-pot (see claim 19), see Example 3, page 7, left-hand column, lines 66-67.
Therefore, the claimed process is found obvious over the ‘683 patent that teaches the crystallization of trenbolone acetate from isopropyl ether and hexane. The reference further teaches trenbolone acetate is soluble in alcohols, which may replace the isopropyl ether solvent for the crystallization while utilizing the teachings of Hardwood and Johnson to seed the crystallization and further obtain a particular size and form of crystal.
To overcome the rejection, unexpected results, commensurate in scope with the claims, may be submitted.
Claims 1-9, 18 and 19 are rejected under AIA 35 U.S.C. 103(a) as being unpatentable over Roussel UCLAF (GB 1035683, cited on the IDS) in view of Hardwood et al. ((Experimental Organic Chemistry, Standard and Microscale, 2nd Edition, 1998, pp. 131-143), Johnson et al. (WO 2007106768, cited on the IDS) and Borodi et al. (Journal of Molecular Structure, 2020, 1-9, cited on the IDS).
The previous 103 rejection is incorporated here.
Borodi et al. teach a crystal structure of trenbolone acetate with the same crystal x-ray spectrum as currently disclosed. The reference does not teach a process of how the trenbolone acetate was synthesized. While the x-ray diffraction pattern is not an indicator of the particle size, the reference does provide support that the same crystal structure was previously made.
Therefore, the claimed process is found obvious over the ‘683 patent that teaches trenbolone acetate is soluble in alcohols, which may replace the isopropyl ether solvent for the crystallization while utilizing the teachings of Hardwood and Johnson to seed the crystallization and further obtain a particular size and form of crystal.
To overcome the rejection, unexpected results, commensurate in scope with the claims, may be submitted.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SUSANNA MOORE whose telephone number is (571)272-9046. The examiner can normally be reached Monday - Friday, 10:00 am to 7:00 pm.
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/SUSANNA MOORE/Primary Examiner, Art Unit 1624