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
Claims 1-16 are pending in the application. Claims 1, 2, 4 and 5 are rejected. Claims 3 and 6-16 are withdrawn from further consideration.
Election/Restrictions
Applicant’s election without traverse of the species TC84-110 to prosecute the invention of Group I, claims 1-5, in the reply filed on February 26th, 2026 is acknowledged.
As per MPEP 803.02, the examiner will determine whether the entire scope of the claims is patentable. Applicants' elected species appears allowable. Therefore, according to MPEP 803.02: should the elected species be found allowable, the examination of the Markush-type claim will be extended. If the examination is extended and a non-elected species found not allowable, the Markush-type claim shall be rejected and claims to the nonelected invention held withdrawn from further consideration. The examination of the Markush-type claims has been extended to include species: 10-acetyl-2-(trifluoromethyl)-phenothiazine, 10-[2-(1-methyl-2-piperidinyl)ethyl]-10H-phenothiazine, 10-(31-dimethylamino-11-propyl)-3-methyl-phenthiazine, and 3-(2,3-dimethyl-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine, which are not allowable.
As a non-elected species has been found not allowable, the Markush-type claims have been rejected and claims to the nonelected invention held withdrawn from further consideration. Claims 1, 2, 4 and 5 embrace the elected species and are therefore under examination. Claims 1, 2, 4 and 5 have been examined to the extent that they are readable on the elected embodiment and the above identified nonelected species. Since the nonelected species has been found not allowable, subject matter not embraced by the elected embodiment or the above identified nonelected species is therefore withdrawn from further consideration.
Claims 3 and 6-16 are withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to a non-elected species or invention.
Information Disclosure Statement
The Examiner has considered the Information Disclosure Statement(s) filed on December 9th, 2024.
Claim Rejections - 35 USC § 112(b)
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.
Claim 4 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 applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 4 is rejected because it refers to chemical labels as set forth in the specification in, for instance, Table 1 beginning on page 41 of the instant specification. A claim should particularly point out and distinctly claim the subject matter which the applicant regards as his invention and, under modern claim practice, stand alone to define the invention. MPEP 2173.05(s) states “Where possible, claims are to be complete in themselves. Incorporation by reference to a specific figure or table “is permitted only in exceptional circumstances where there is no practical way to define the invention in words and where it is more concise to incorporate by reference than duplicating a drawing or table into the claim. Incorporation by reference is a necessity doctrine, not for applicant’s convenience.” Ex parte Fressola, 27 USPQ2d 1608, 1609 (Bd. Pat. App. & Inter. 1993)”. In this situation, the compound labeling system is only found in Applicant’s disclosure but the compounds could otherwise be readily recited in the claim by either structure or standard chemical naming conventions, e.g. as in instant claim 5.
Claim Rejections - 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.
Claim(s) 1 and 4 is/are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by U.S. Patent No. 2,997,468 by Schwartz.
The prior art teaches 10-acetyl-2-(trifluoromethyl)-phenothiazine in Example 13 in column 4, which has the following structure:
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The compound is embraced by claim 1 where X is S, one of R1 and R4 is CF3 and the other is hydrogen, R2 and R3 are hydrogen, Q is CO and R5 is C1 alkyl. The compound is further instantly disclosed as Compound ID No. TC84-32 and is recited in instant claim 4.
Claim(s) 1 and 2 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shapiro et al. Journal of the American Pharmaceutical Association 1957, XLVI, pages 333-336.
The prior art teaches 10-[2-(1-methyl-2-piperidinyl)ethyl]-10H-phenothiazine having the following structure (page 333):
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The compound is embraced by Formula I where X is S, R1-R4 are hydrogen, Q is CH2 and R5 is substituted C1 alkyl. The compound is further embraced by Formula 2 of claim 2 where X is S, R1-R4 are hydrogen, Q is CH2, n is 1 and R6 is CH3.
Claim(s) 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by GB 724217 A.
The prior art teaches compounds having the following general backbone having a substituent at the 1- or 3-position:
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As an example, the prior art teaches 10-(31-dimethylamino-11-propyl)-3-methyl-phenthiazine on page 3 (Example 1), which has the following structure:
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The compound is embraced by Formula I where X is S, one of R1 and R4 is CH3 and the other is hydrogen, R2 and R3 are hydrogen, Q is CH2 and R5 is substituted C1alkylaminoC2alkyl.
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, 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.
Claim(s) 1, 4 and 5 is/are rejected under 35 U.S.C. 103 as being unpatentable over GB 724217 A.
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
The prior art teaches compounds having the following general backbone having a substituent at the 1- or 3-position:
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As an example, the prior art teaches 10-(31-dimethylamino-11-propyl)-3-methyl-phenthiazine on page 3 (Example 1), which has the following structure:
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The compound is embraced by Formula I where X is S, one of R1 and R4 is CH3 and the other is hydrogen, R2 and R3 are hydrogen, Q is CH2 and R5 is substituted C1alkylaminoC2alkyl.
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
The prior art anticipates instant claim 1 where anticipation is the epitome of obviousness. Instant claims 1, 4 and 5 further encompass compound 3-(2,3-dimethyl-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine (TC84-124), which differs from the prior art structure based on replacement of hydrogen with methyl.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2142-2143)
“Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds. For example, a prior art compound may suggest its
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homologs because
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homologs
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often have similar properties and therefore chemists of ordinary skill would ordinarily contemplate making them to try to obtain compounds with improved properties.” In re Deuel 34 USPQ2d 1210 at 1214. Furthermore MPEP 2144.09 (II) states: “Compounds which are […] homologs (…) 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).”
The issue of patentability over the replacement of alkyl groups for hydrogen has arisen many times. For instance, the replacement of a methylene group with a dialkyl-substituted methylene group was determined to be prima facie obvious on the ground that “one skilled in the art would have been, prima facie, motivated to make the claimed compounds in the expectation that they, too, would possess antimicrobial activity." (In re Wood 199 USPQ 137) See also In re Doebel 174 USPQ 158 (where replacement of methyl for hydrogen on an amino nitrogen was considered prima facie obvious – at page 159); In re Druey 138 USPQ 39 (where replacement of methyl for hydrogen on a known compound was considered prima face obvious based on the homologous and close structural relationship to the known compound – at page 41); In re Lohr 137 USPQ 548 (where the replacement of a methyl group for a hydrogen on two positions of a tetrahydropyran ring on a known compound was not considered a patentable modification given the close structural relationship to the known compounds - at page 550); Ex parte Bluestone 135 USPQ 199 (where fungicidal compounds differing by hydrogen versus methyl on the nitrogen of a thiazolidine-2-thione ring were considered homologs and were not found to be patentable over each other without a showing of unexpected results – at page 200); Ex parte Weston 121 USPQ 429 (where the replacement of methyl for hydrogen on the nitrogen of a piperazine ring was not found to be a patentable modification); Ex parte Fauque 121 USPQ 425 (where di(methyl-furyl)-methane was considered a higher homolog of difuryl-methane and unpatentable without a showing of unexpected results - at page 426).
The motivation to make a substitution of an alkyl group for hydrogen stems from the fact that a person having ordinary skill in the art would expect that the compounds would have the same utility as the compounds taught by the prior art. In the interest of generating additional compounds that have the same utility as the compounds taught by the prior, a person having ordinary skill in the art would seek to make additional compounds that are most closely related to compounds specifically taught by the prior art that have already been demonstrated to have the desired utility. As discussed above, the replacement of hydrogen for an alkyl group falls under the well-established doctrine of homology, which assumes that homologous compounds are likely to have similar properties. Therefore, the instantly claimed compound, which differs by hydrogen/alkyl, over a compound of prior art is unpatentable absent a showing of unexpected results. MPEP 2144.09 (VII) states “A prima facie case of obviousness based on structural similarity is rebuttable by proof that the claimed compounds possess unexpectedly advantageous or superior properties. In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963).” In the instant case, Applicant has not established unexpected properties between the instantly claimed compound and the closest prior art homolog. In the instant case, a person having ordinary skill in the art at the time the invention was made would have been motivated to synthesize the instantly claimed homolog with the reasonable expectation that it would have the same utility as the closest structurally related compound taught by the prior and with the motivation of obtaining additional useful compounds.
Furthermore, the prior art compares a compound having a methoxy substituent at the 2-position on page 3 (left column, lines 11-21) relative to the 3-position. At least in the interest of fleshing out the biological activity profile of the core structure, a person having ordinary skill in the art would have been motivated to prepare the instantly claimed compound to determine whether the changes observed are due specifically to the methoxy substituent.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MATTHEW P COUGHLIN whose telephone number is (571)270-1311. The examiner can normally be reached Monday - Friday, 10 am - 6 pm EST.
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/MATTHEW P COUGHLIN/Primary Examiner, Art Unit 1626